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99011-02-6 Usage

Drug for treatment of Genital warts

Imiquimod is a kind of imidozoquinoline amine-class interleukin agonist developed by the 3M Pharmaceuticals Company (US), belonging to the drug for the treatment of genital warts. Upon being applied to the mice skin, it can induce the cytokinesis and produce α-interferon, tumor necrosis factor and many kinds of interleukins. Clinically it can be used as the immunomodulators in the treatment of adult genital and perianal warts with convenient application, well tolerance and unique mechanism of action which makes it be the first-choice drug for treatment of genital warts. In addition, there are reports that imiquimod can be used for treating viral skin diseases including common warts, flat warts, molluscum and herpes simplex virus. It can also be effective in treating basal cell carcinoma, Bowen's disease, Bowen papulosis, actinic keratosis, and skin tumors such as cutaneous T-cell tumor and Kaposi's sarcoma. It may also be effective in treating vitiligo and alopecia areata. Genital wart is the infective diseases of the human herpes virus (HPV) infection and is a major public health threat. Currently, the infection of the genital wart in the United States is the most common viral infective sexually transmitted diseases and one of the most common sexually transmitted diseases. The infections mostly occur in sexually active people, especially for people of 20 to 24 year-olds and women in pregnancy, and prone to happen at the warm and most mucosal sites of body. Application of immunosuppressive agents or infection with the patients of human immunodeficiency virus is prone to cause severe clinical signs of infection.

Clinical Study

In an unpublished report, 209 cases of patients of genital or perianal warts have been subjected to a double-blind trial with both this product and vehicles being used for three times per week for continuous 16 weeks. The results have shown that, 33 cases in 46 cases of women (72%), 21 cases in 63 cases of male(33%) get cured with the total wart cure rate being 50%, while only 11% (20% of women and 5% male) in the vehicles group get cured. There have been patients who get cured within treatment of only 4 weeks. The average healing time is twelve weeks for men and eight weeks for women. In the following 12 weeks, there were 39 cases in 54 cases that got no recurrence any more.

Mechanism of action

Different sources of media describe the Mechanism of action of 99011-02-6 differently. You can refer to the following data:
1. Imiquimod itself has no direct effect on the virus itself, but instead through stimulating the body for producing cytokines and stimulating immune response to eliminate the wart tissue and reduce the viral erosion. Both in vivo and in vitro studies have suggested that imiquimod can stimulate the mice, rats, rabbits, guinea pigs, monkeys and humans for producing cytokine. Racial cross cell culture tests have shown that the main responsive cells are monocytes/macrophages; cultured human peripheral mononuclear cells (PBMC) which can produce several subtypes of IFN-α, TNF-α, IL-1,6,6 , 10,12, MIP-1 and MCP-1; the human single cell THP-1 will respond only when being pre-subject to γ-IFN treatment and produce TNF-α, IL-1,6,8, but do not produce IFN-α; performing the same treatment on the fresh mice PBMC can generate the same cytokine as human PBMC; senescence macrophages and alveolar macrophages produce the same cytokines, the mouse RAW264.7 and J774 macrophages family can produce TNF-α and IL-6 without producing IFN-α. Through intracellular test, we can confirm that imiquimod can induce IFN-α and TNF-α. Through putting the human fibroblasts and keratinocytes with the mixture of imiquimod or poly-inosine: poly-cytidine for incubation of 24 hours, people has found that the mRNA of keratinocytes IL-6 and IL-8 (no TNF-α) had increased but only appropriate amount of IL-8 protein had been detected. At high concentration, the secretion of the fibroblasts IL-8 is similar with keratinocytes; The immune response of caused by the imiquimod-induced secretion of cytokines is similar with the DTH response; imiquimod can activate the anti-tumor activity and DTH response of the HPV E7 gene transfected tumor bearing mice; human and animal experiments have shown that imiquimod could increase the 2'5'-oligo-adenylate synthase which can induce the interferon for inducing the antiviral effect; interferons and other cytokines can activate NK cells to kill tumor cells and the virus-infected cells; both in vivo and in vitro tests have showed that the imiquimod can increase activity of NK and stimulate the proliferation and activation of mouse spleen B cells which is the direct effect rather than being mediated by cytokine; imiquimod does not directly enhance T-lymphocyte activity; but in vitro mitogenic response can stimulate T-cells for enhancing the production and proliferation of IL-2. In vivo experiments have demonstrated that it can enhance T cell activity; imiquimod can increase the generation of IL-2 of the HSV infected guinea pig, T cell proliferation and T cell activity to enhance the cell-mediated immune response. The above information is edited by the lookchem of Dai Xiongfeng.
2. Imiquimod (Aldara) is an imidazoquinolone amine that is an immune responsemodifier. Its exact mechanism is unknown in the topical treatment of HPV and molluscum contagiosum but may be related to the immunomodulating effect of the drug. It is also effective in the treatment of actinic keratoses and superficial basal cell carcinoma. It induces production of a variety of cytokines and can enhance cell-mediated cytolytic antiviral activity. It is a rapid and potent inducer of interferon-α, interleukin?1 α and β, interleukin 6, interleukin 8, tumor necrosis factor-α, granulocyte-macrophage colony-stimulating factor, and granulocyte colonystimulating factor. Systemic absorption is minimal. It is generally well tolerated. Adverse local reactions include erythema, erosion, excoriation, flaking, and edema of the treatment sites.

Usage and Dosage

It can be used for the treatment of adult external genital and perianal genital warts at 3 times per week. Just before sleep, first apply the product evenly in a thin layer on the surface of the wart and gently massage until the product is completely absorbed. The position of the medication should not be packeted and should be maintained for 6 to 10 hours, and then wash with a neutral soap and clean water for clearing the drugs in the administration site. Wash your hands before and after treatment. 250 mg of cream can be applied to 20cm2 of wart. Avoid excessive application of the drug. Patients should continue the treatment until the wart is completely cleared. Wart can be cleared within 2-4 week at the fastest speed and can be generally cleared within 8 to 12 weeks. The medication should be not more than 16 weeks. After the treatment, patients with mild erythema locally who does not have to be discontinued for drug; if the patients feel general malaise or get local skin reactions (edema, erosion, pain, etc.), the drug should be discontinued. Only when the reaction is alleviated can they continue the medication.

Side effects

1, the majority of patients get no adverse reactions during the treatment. After several times of treatment, the clinical adverse reactions are mostly mild, moderate local skin inflammation. For example, there may be local skin erythema, edema, erosion, ulcers, desquamation, burning, pain, itching and so on. 2, there is occasional transient fever and these symptoms can quickly recover after stopping the drugs. If the reactions are mild, you can continue for the treatment. However, the patients should discontinue the drug on time and should be subject to medical treatment if severe reactions happen. 3, According to the reports of foreign information, possible adverse reactions associated with imiquimod cream include discomfort in the medication site, wart site reactions (burning, pigmentation, inflammation, itching, pain, rash, sensitivity, ulcers, tingling and tenderness).Distal site reactions (bleeding, burning, itching, pain and tenderness), fatigue, fever, flu-like symptoms, headache, diarrhea, myalgia.

Precautions

1. No packets; wash away the drug after 6 to 10 hours of the drug administration. The patients should avoid using this product in partial breakage place. There have been reports of using drugs or laser for treatment of genital warts that lead to the emergence of damaged parts. In that case, we should continue the drugs until the wound get healed. 2. It should not be applied to the treatment of genital warts located at the eyes, mouth, nose, urethra, vagina, cervix and anal mucous membranes. 3. You should avoid sex during the treatment. For patients using condom, the patients should first clean the topical imiquimod because imiquimod can make condom be fragile. 4. For male patients with foreskin, during the treatment, the patients should reveal the foreskin every day and clean the application site. If the foreskin mucosa surface gets erosion, ulceration, edema and difficulty for turning up foreskin, you should immediately stop the treatment. 5. There have been no reports regarding the drug contraindications in pregnant and lactating women, but the patients should use with caution.

Uses

Different sources of media describe the Uses of 99011-02-6 differently. You can refer to the following data:
1. It can be used for anti-genital warts and as immunomodulators
2. raw material for Latamoxef, Cefminox, Ceftizoxime, Cefoxitin, Cefmetazole
3. An immune response modifier. It stimulates the production of interferon-a
4. Imiquimod is a caspase 3 activator which acts as an immunomodulator and displays antiviral and anti-tumor activity. It is a patient-applied cream used for the treatment of genital warts and basal cell carcinoma. It is also used to cure actinic keratosis on the face and scalp. It belongs to a group of drugs called immune response modifiers, which work by activating the immune system to fight abnormal skin growth.

Description

Aldara was launched in the US for the topical treatment of genital warts caused by human papillomavirus (HPV). It can be prepared in a six step approach beginning with the nucleophilic substitution of 4-chloro-3-nitroquinolone with isobutylamine or via a thermal electrocyclic ring closure of 1 - and 2-azahexatriene systems. Aldara has antiviral and antitumor properties, with the former activity arising from the induction of cytokines, in particular, INF-α. Aldara also induces TNF-γ, IL-1α, IL-1β, IL-1ra, IL-6, IL-8, IL-10, GM-CSF, G-CSF and MID-la formation 1-4 hr after stimuli. The exact cells responsible for the response have not been determined, however, it is not activating T lymphocytes, NK cells, B lymphocytes, or dendritic stem cells but monocytes (CD14+, CD36+, HLA-DR+, HLA-DQ±, CD19-, CD16- and CD23-) are partly responsible. The speculation is that Aldara may interact with a kinase modulating the transduction pathway leading to cytokine genes. There is no direct antiviral activity (induction of IFN does not follow true dose response) and it is not mutagenic. The hydroxylated metabolite also induces IFN-α.

Originator

3M Pharmaceuticals (US)

Indications

Imiquimod (Aldara) is a topical immune response modifier approved for the treatment of anogenital warts (condylomata acuminata). The exact mechanism of action is unknown; it has no direct antiviral activity in vitro. It is thought to work in vivo by inducing the production of tumor necrosis factor (TNF α ), interferons (IFN)α and γ , and other cytokines with antiviral activity. It may also be useful for treatment of other types of warts, molluscum contagiosum, and certain forms of skin cancer. Local irritant reactions related to the frequency of application are common.

Brand name

Aldara (3M Pharmaceuticals).

Pharmaceutical Applications

An imidazoquinoline used for the treatment of genital and perianal warts. While the mechanism of action is not precisely known, it is thought to induce interferon. It has no direct antiviral activity. The 5% cream applied three times a week for up to 16 weeks resulted in total wart clearance in 50% of patients, with a better response in women than in men. Local reactions are common and include erythema, erosion, excoriation and edema.

Biological Activity

Immunomodulator that displays antiviral and antitumor activity. Acts as a Toll-like receptor 7 (TLR-7) agonist; stimulates proinflammatory cytokine production and activates NF- κ B.

Biochem/physiol Actions

Imiquimod is a caspase 3 activator, which directly induces procaspase 3 cleavage to active caspase 3. Imiquimod induces apoptosis in vivo in basal cell carcinoma. Its anti-tumor activity is related to the induction of apoptosis. Imiquimod has anti-angiogenic, anti-inflammatory, anti-viral activities. Imiquimod also acts as an immune response modulator inducing the secretion of various cytokines and chemokines.

Veterinary Drugs and Treatments

An immune response modifier, imiquimod may be useful in the treatment of a variety of topical conditions in animals. It is labeled for use on humans as a treatment for genital or perianal warts, superficial basal cell carcinomas and actinic keratoses of the face and scalp. In dogs and cats, imiquimod potentially may be of benefit in treating feline herpes virus dermatitis, actinic keratosis, squamous cell carcinoma and Bowen’s disease, papillomas virus lesions, and localized solar dermatitis or solar carcinoma in situ. In horses, imiquimod has been anecdotally used with success in treating sarcoids. Imiquimod stimulates the patient’s own immune system to release a variety of cytokines including interferon-alpha and interleukin- 12. Imiquimod itself does not have in vitro activity against wart viruses, but stimulates monocytes and macrophages to release cytokines that induce a regression in viral protein production.

References

1) Hemmi?et al.?(2002),?Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway;?Nat. Immunol.?3?196 2) Stanley?et al.?(2002),?Imiquimod and the imidazoquinolones: mechanism of action and therapeutic potential;?Clin. Exp. Dermatol.?27?571 3) Schoen?et al.?(2006),?The small antitumoral immune response modifier imiquimod interacts with adenosine receptor signaling in a TLR7- and TLR8-independent fashion;?J.Invest.Dermatol.?126?1338 4) Kan?et al.?(2012),?Imiquimod Suppresses Propagation of Herpes Simplex Virus 1 by Upregulation of Cystatin A via the Adenosine Receptor A1?Pathway.; J. Virol.?86?10338 5) Urosevic?et al.?(2004),?Imiquimod Treatment Induces Expression of Opioid Growth Factor Receptor; Clin. Cancer Res.?10?4959 6) Zagon?et al.?(2008),?Imiquimod Upregulates the Opioid Growth Factor Receptor to Inhibit Cell Proliferation Independent of Immune Function.; Exp. Biol. Med.(Maywood)?233?968

Check Digit Verification of cas no

The CAS Registry Mumber 99011-02-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,9,0,1 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 99011-02:
(7*9)+(6*9)+(5*0)+(4*1)+(3*1)+(2*0)+(1*2)=126
126 % 10 = 6
So 99011-02-6 is a valid CAS Registry Number.
InChI:InChI=1/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)

99011-02-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (I0747)  Imiquimod  >98.0%(HPLC)(T)

  • 99011-02-6

  • 100mg

  • 490.00CNY

  • Detail
  • TCI America

  • (I0747)  Imiquimod  >98.0%(HPLC)(T)

  • 99011-02-6

  • 1g

  • 2,990.00CNY

  • Detail
  • USP

  • (1338313)  Imiquimod  United States Pharmacopeia (USP) Reference Standard

  • 99011-02-6

  • 1338313-200MG

  • 4,326.66CNY

  • Detail

99011-02-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name imiquimod

1.2 Other means of identification

Product number -
Other names Imiquimod

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:99011-02-6 SDS

99011-02-6Synthetic route

4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline
201030-96-8

4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Product distribution / selectivity; Heating / reflux;98%
Stage #1: 4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 20℃;
Stage #3: With ammonia In water at 20℃; Product distribution / selectivity;
98%
4-chloro-1H-imidazo[4,5-c]-quinoline
132206-92-9

4-chloro-1H-imidazo[4,5-c]-quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In dimethyl sulfoxide for 0.5h;
Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In dimethyl sulfoxide at 105℃; for 2h;
Stage #3: With hydrogenchloride In water; dimethyl sulfoxide pH=8; Product distribution / selectivity;
98%
N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide

N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ethylenediamine In water at 70 - 95℃; for 4h;91.8%
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide With hydrazine In water at 70℃;
Stage #2: With 2,4,4-trimethylpentan-1-ol In water at 94 - 95℃; for 5h;
Stage #3: In methanol; water at 60℃; for 0.25h; Heating / reflux;
63.3%
4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; water In methanol Product distribution / selectivity;90%
5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile
960254-02-8

5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium amide In toluene at 20 - 100℃; for 2h;90%
4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: 4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate In methanol; water at 75℃; for 0.5h;
Stage #2: With ammonia In water
89.7%
With ammonia; water In methanol Product distribution / selectivity;89.7%
4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; water In methanol Product distribution / selectivity;88%
4-iodo-1-isobutyl-1H-imidazo-[4,5-c]-quinoline
896106-15-3

4-iodo-1-isobutyl-1H-imidazo-[4,5-c]-quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia In methanol at 150 - 155℃; Autoclave (ca. 20 kg pressure);86%
With ammonia In methanol at 150 - 155℃; under 14711.4 Torr; Product distribution / selectivity; Autoclave;86%
4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
99010-64-7

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia In dimethyl sulfoxide at 20 - 150℃; under 1875.19 - 3750.38 Torr; for 6 - 12h; Product distribution / selectivity;85.7%
With ammonia at 150℃; for 7h;82%
With ammonia; formamide at 145℃; for 20 - 25h; Product distribution / selectivity;78%
imiquimod hydrochloride

imiquimod hydrochloride

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: imiquimod hydrochloride With sodium hydrogensulfide; pyrographite In water at 85 - 90℃; for 0.333333h;
Stage #2: With ammonium hydroxide In water at 20 - 80℃; Purification / work up;
80.5%
With sodium hydroxide In water at 20℃; for 0.5h; Product distribution / selectivity;
1-Isobutyl-2-methylsulfanyl-1H-imidazo[4,5-c]quinolin-4-ylamine
177212-77-0

1-Isobutyl-2-methylsulfanyl-1H-imidazo[4,5-c]quinolin-4-ylamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 0.5h; Heating;80%
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide
99010-63-6

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; chloroformic acid ethyl ester In dichloromethane; water at 0 - 20℃; for 1h; Cooling with methanol-ice bath;76%
With ammonium hydroxide; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 0.25h;71%
Multi-step reaction with 2 steps
1: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
2: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: CH2Cl2 / 0.25 h / Heating
2: NaOMe / methanol / 2 h / Heating
View Scheme
4-bromo-1H-imidazo[4,5-c]quinoline

4-bromo-1H-imidazo[4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In ISOPROPYLAMIDE for 0.5h;
Stage #2: 4-bromo-1H-imidazo[4,5-c]quinoline In ISOPROPYLAMIDE at 140℃; for 2h; Product distribution / selectivity;
75.4%
N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine

N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With hydrogenchloride; zinc In ethanol; water at 20℃; for 1h; Product distribution / selectivity;70%
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-O-methyl-hydroxylamine With hydrogenchloride; zinc In ethanol; water at 20℃; for 1h;
Stage #2: With sodium hydroxide In ethanol; water for 0.5h; Product distribution / selectivity;
70%
1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine
1040136-68-2

1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine With sulfuric acid; water In dimethyl sulfoxide at 140℃; for 20h;
Stage #2: With sodium hydroxide; water In dimethyl sulfoxide at 20 - 60℃; for 2h; pH=10 - 11; Product distribution / selectivity;
70%
Stage #1: 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine In dimethyl sulfoxide at 140 - 150℃; for 9h;
Stage #2: With sodium hydroxide; water In dimethyl sulfoxide at 20 - 60℃; for 2h; pH=10 - 11; Product distribution / selectivity;
4-chloro-1H-imidazo[4,5-c]-quinoline
132206-92-9

4-chloro-1H-imidazo[4,5-c]-quinoline

A

1-isobutyl-1H-imidazo[4,5-c]quinoline-4-formamide

1-isobutyl-1H-imidazo[4,5-c]quinoline-4-formamide

B

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In ISOPROPYLAMIDE for 0.5h;
Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In ISOPROPYLAMIDE at 120℃; for 1h; Product distribution / selectivity;
A 54%
B 39%
N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
144660-62-8

N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Heating;
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
99010-24-9

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: peracetic acid / ethanol / 2.5 h / 60 °C
2: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
3: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 2 steps
1: peracetic acid / ethanol / 2.5 h / 60 °C
2: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: peracetic acid / ethanol / 2.5 h / 60 °C
2: CH2Cl2 / 0.25 h / Heating
3: NaOMe / methanol / 2 h / Heating
View Scheme
3-Amino-4-(2-methylpropylamino)-quinoline
99010-09-0

3-Amino-4-(2-methylpropylamino)-quinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1 h / Heating
2: peracetic acid / ethanol / 2.5 h / 60 °C
3: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
4: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 3 steps
1: 1 h / Heating
2: peracetic acid / ethanol / 2.5 h / 60 °C
3: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 1 h / Heating
2: peracetic acid / ethanol / 2.5 h / 60 °C
3: CH2Cl2 / 0.25 h / Heating
4: NaOMe / methanol / 2 h / Heating
View Scheme
N-(2-methylpropyl)-3-nitro-4-quinolinamine
99009-85-5

N-(2-methylpropyl)-3-nitro-4-quinolinamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
2: 1 h / Heating
3: peracetic acid / ethanol / 2.5 h / 60 °C
4: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
5: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 4 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
2: 1 h / Heating
3: peracetic acid / ethanol / 2.5 h / 60 °C
4: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
2: 1 h / Heating
3: peracetic acid / ethanol / 2.5 h / 60 °C
4: CH2Cl2 / 0.25 h / Heating
5: NaOMe / methanol / 2 h / Heating
View Scheme
2-chloro-N4-(2-methylpropyl)quinoline-3,4-diamine
133860-76-1

2-chloro-N4-(2-methylpropyl)quinoline-3,4-diamine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 61 percent / toluene / 1.5 h / Heating
2: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
2-chloro-N4-(2-methylpropyl)-3-nitroquinoline-4-amine
133860-75-0

2-chloro-N4-(2-methylpropyl)-3-nitroquinoline-4-amine

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr
2: 61 percent / toluene / 1.5 h / Heating
3: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
quinolin-4-ol
611-36-9

quinolin-4-ol

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C
2: SOCl2; DMF / CH2Cl2 / 3 h / Heating
3: Et3N / CH2Cl2 / 0.25 h / Heating
4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
5: 1 h / Heating
6: peracetic acid / ethanol / 2.5 h / 60 °C
7: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
8: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 7 steps
1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C
2: SOCl2; DMF / CH2Cl2 / 3 h / Heating
3: Et3N / CH2Cl2 / 0.25 h / Heating
4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
5: 1 h / Heating
6: peracetic acid / ethanol / 2.5 h / 60 °C
7: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: 81 percent / aq. HNO3 / propionic acid / 0.25 h / 125 °C
2: SOCl2; DMF / CH2Cl2 / 3 h / Heating
3: Et3N / CH2Cl2 / 0.25 h / Heating
4: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
5: 1 h / Heating
6: peracetic acid / ethanol / 2.5 h / 60 °C
7: CH2Cl2 / 0.25 h / Heating
8: NaOMe / methanol / 2 h / Heating
View Scheme
4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one
15151-57-2

4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: POCl3; Et3N / toluene / 4 h / 80 - 90 °C
2: 17.8 g / Et3N / CH2Cl2 / 0.5 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr
4: 61 percent / toluene / 1.5 h / Heating
5: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
3-nitro-quinolin-4-ol
50332-66-6

3-nitro-quinolin-4-ol

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: SOCl2; DMF / CH2Cl2 / 3 h / Heating
2: Et3N / CH2Cl2 / 0.25 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
4: 1 h / Heating
5: peracetic acid / ethanol / 2.5 h / 60 °C
6: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
7: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 6 steps
1: SOCl2; DMF / CH2Cl2 / 3 h / Heating
2: Et3N / CH2Cl2 / 0.25 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
4: 1 h / Heating
5: peracetic acid / ethanol / 2.5 h / 60 °C
6: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: SOCl2; DMF / CH2Cl2 / 3 h / Heating
2: Et3N / CH2Cl2 / 0.25 h / Heating
3: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
4: 1 h / Heating
5: peracetic acid / ethanol / 2.5 h / 60 °C
6: CH2Cl2 / 0.25 h / Heating
7: NaOMe / methanol / 2 h / Heating
View Scheme
4-chloro-3-nitroquinoline
39061-97-7

4-chloro-3-nitroquinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 0.25 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
3: 1 h / Heating
4: peracetic acid / ethanol / 2.5 h / 60 °C
5: 49 percent / POCl3 / CH2Cl2 / 0.25 h / Heating
6: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2 / 0.25 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
3: 1 h / Heating
4: peracetic acid / ethanol / 2.5 h / 60 °C
5: 71 percent / aq. NH3; tosyl chloride / CH2Cl2 / 0.25 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 0.25 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2740.88 Torr
3: 1 h / Heating
4: peracetic acid / ethanol / 2.5 h / 60 °C
5: CH2Cl2 / 0.25 h / Heating
6: NaOMe / methanol / 2 h / Heating
View Scheme
2,4-dichloro-3-nitroquinoline
132521-66-5

2,4-dichloro-3-nitroquinoline

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 17.8 g / Et3N / CH2Cl2 / 0.5 h / Heating
2: H2; MgSO4 / Pt/C / ethyl acetate / 2585.74 Torr
3: 61 percent / toluene / 1.5 h / Heating
4: 82 percent / methanolic NH3 / 7 h / 150 °C
View Scheme
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: PdCl2(PPh3)2, K2CO3, Et4N(1+)Cl(1-) / dimethylformamide / 2 h / 110 °C
2: 10percent aq. NaOH / dioxane / 12 h / Heating
3: Et3N, DPPA / benzene / 1 h / 50 °C
4: 1,2-dichloro-benzene / 1 h / Heating
5: 88 percent / POCl3 / 1 h / Heating
6: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C
7: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating
View Scheme
1-isobuty-1H-limidazole
16245-89-9

1-isobuty-1H-limidazole

imiqimod
99011-02-6

imiqimod

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT, 12 h
2: 83 percent / NBS / CCl4 / 1 h / Ambient temperature
3: 98 percent / Pd(PPh3)4, aq. Na2CO3 / toluene; ethanol / 4 h / 110 °C
4: 98 percent / NBS / CCl4 / 1 h
5: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 1 h, 2.) Et2O, hexane, RT, 12 h
6: 46 percent / Et3N, PPh3, CCl4 / acetonitrile / 1.) RT, 1 h, 2.) reflux, 3 h
7: 62 percent / 1,2-dichloro-benzene / 8 h / Heating
8: 41 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 4 h / Heating
9: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C
10: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating
View Scheme
maleic acid
110-16-7

maleic acid

imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

Conditions
ConditionsYield
In methanol; water at 74℃; Heating / reflux;91%
imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

Conditions
ConditionsYield
With maleic acid In methanol; water at 74℃; for 0.5h;91%
oxalic acid
144-62-7

oxalic acid

imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 160℃; for 0.5h;90%
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

imiqimod
99011-02-6

imiqimod

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 160℃; for 0.5h;89%
N-t-butyloxycarbonyl-N-methylglycine anhydride
70533-97-0

N-t-butyloxycarbonyl-N-methylglycine anhydride

imiqimod
99011-02-6

imiqimod

tert-butoxycarbonyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-sarcosine

tert-butoxycarbonyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-sarcosine

Conditions
ConditionsYield
With triethylamine for 8h; Reflux;87.5%
With triethylamine In ethyl acetate for 2h; Reflux;87.5%
imiqimod
99011-02-6

imiqimod

C14H14(2)H2N4

C14H14(2)H2N4

Conditions
ConditionsYield
With deuterium In N,N-dimethyl acetamide under 1500.15 Torr; for 24h; Glovebox; Heating;80%
imiqimod
99011-02-6

imiqimod

benzyl alcohol
100-51-6

benzyl alcohol

N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
415726-68-0

N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

Conditions
ConditionsYield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 140℃; for 18h; Sealed tube;72%
5-bromo-2,3-dihydrobenzo[b]furan
66826-78-6

5-bromo-2,3-dihydrobenzo[b]furan

imiqimod
99011-02-6

imiqimod

C22H22N4O

C22H22N4O

Conditions
ConditionsYield
With copper(l) iodide; N,N'-dibenzylethanediamide; potassium tert-butylate In tert-butyl alcohol at 100℃; for 24h; Molecular sieve; Schlenk technique; Inert atmosphere;43%
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
1188307-60-9

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

imiqimod
99011-02-6

imiqimod

C36H39N5O14

C36H39N5O14

Conditions
ConditionsYield
Stage #1: imiqimod With N-ethyl-N,N-diisopropylamine In ethyl acetate for 0.333333h; Microwave irradiation;
Stage #2: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate In ethyl acetate at 87℃; for 0.75h; Microwave irradiation;
40%
Stage #1: imiqimod With N-ethyl-N,N-diisopropylamine In ethyl acetate Microwave irradiation;
Stage #2: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitro-4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate In ethyl acetate at 87℃; for 0.75h; Microwave irradiation;
40%
imiqimod
99011-02-6

imiqimod

ethane-1,2-diyl bis(4-nitrophenyl carbonate)

ethane-1,2-diyl bis(4-nitrophenyl carbonate)

2-(4-nitrophenyl carbonate)ethyl (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)carbamate

2-(4-nitrophenyl carbonate)ethyl (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)carbamate

Conditions
ConditionsYield
In tetrahydrofuran at 90℃; under 750.075 Torr; for 0.833333h; Microwave irradiation; Sealed tube;39%
2-(2-nitrophenyl)propyl chloroformate
179691-31-7

2-(2-nitrophenyl)propyl chloroformate

imiqimod
99011-02-6

imiqimod

C24H25N5O4

C24H25N5O4

Conditions
ConditionsYield
In 1,4-dioxane at 10 - 50℃; for 6h;38%
C42H76N2O15

C42H76N2O15

imiqimod
99011-02-6

imiqimod

C56H90N6O14

C56H90N6O14

Conditions
ConditionsYield
With HATU In dichloromethane at 20℃;35%
imiqimod
99011-02-6

imiqimod

8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
723281-26-3

8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Conditions
ConditionsYield
With bromine; acetic acid at 20℃; for 18h;26%
Stage #1: imiqimod With bromine In acetic acid for 24h;
Stage #2: With sodium carbonate In water for 18h;
With N-Bromosuccinimide In chloroform at 20 - 50℃; for 1.83333h; Heating / reflux;

99011-02-6Relevant articles and documents

Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N -Oxides via N -(2-Pyridyl)pyridinium Salts

Xiong, Hui,Hoye, Adam T.

supporting information, p. 371 - 375 (2022/01/27)

A synthesis of 2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt

Imiquimod Production Process

-

Page/Page column 2; 4, (2008/12/07)

Provided is a process for producing highly pure 4-amino-1-isobutyl-1H-imidazo[4,5-c]quinoline (imiquimod), which includes reacting 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline with a non-gaseous amine precursor. Also provided are methods for isolating highly pure imiquimod. Further provided are intermediates useful in the production of imiquimod, methods for producing such intermediates, and methods for obtaining imiquimod from such intermediates.

Preparation of 1H-imidazo[4,5-c]quinolin-4-amines via 1H-imidazo[4, 5-c]quinolin-4-phtalimide intermediates

-

Page/Page column 6, (2008/06/13)

The present invention provides process for the preparation of 4-amino-1H-imidazo[4,5-c]quinolines comprising the step of reacting a 1H-imidazo[4,5-c]quinolin-4-phthalimide with an amine selected from the group consisting of: alkylamine, aralkylamine, alkyldiamine, and aralkyldiamine.

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