141845-82-1

Basic information

• Product Name: Ciclesonide
• Synonyms: Ciclesonide;(R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate;Alvesco;Omnaris;Pregna-1,4-diene-3,20-dione, 16,17-(((R)-cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha)-;Pregna-1,4-diene-3,20-dione, 16,17-((cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha(R))-;Rpr 251526;Unii-S59502J185
• CAS NO: 141845-82-1
• Molecular Formula: C32H45O7
• Molecular Weight: 540.69
• Mol File: 141845-82-1.mol

Chemical Properties

• Boiling Point: 665°C at 760 mmHg
• Flash Point: 210°C
• Appearance: White crystalline powder
• Density: 1.23g/cm³
• Vapor Pressure: 1.61E-20mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: Ciclesonide(CAS DataBase Reference)
• NIST Chemistry Reference: Ciclesonide(141845-82-1)
• EPA Substance Registry System: Ciclesonide(141845-82-1)

Safety Data

• Hazardous Substances Data: 141845-82-1(Hazardous Substances Data)

Usage

Asthma medication

Ciclesonide is a new inhaled glucocorticoid drug for treating asthma,it belongs to adrenocorticotropic hormone drugs, similar drugs also include beclomethasone dipropionate, budesonide, fluticasone propionate, the product is administrated in a non-active form ,it can be activated by endogenous esterases in the airway on the spot , it becomes into an active ingredient when it reaches the target organ-the lung; once it is activated, it shows a high topical anti-inflammatory activity. Ciclesonide is successfully developed by the pharmaceutical company Altana, it was listed in January 2005 for the first time in the UK, it is currently available in Germany, Ireland, it is used for the treatment of adults with all levels of persistent severe asthma, one administration per day , a dose of 160μg or 80μg. For patients with severe asthma attack facing the risk of asthma, if the condition can not be controlled and strong anti-inflammatory drugs are required , the dose of this product be increased to 160μg. In clinical trail phase III of severe patients with persistent asthma, ciclesonide has new release and distribution properties,it can reduce the local and systemic adverse reactions, and it can maintain high anti-asthma activity, it can significantly low the need on oral corticosteroids (OCS) in patients to maintain or improve effects of asthma control. Accordingly, it is an appropriate OCS saving therapy.

Side Effects

Ciclesonide becomes effective faster than budesonide,its systemic side effects are lower than the fluticasone propionate and budesonide, even though the highest doses of 160μg is used, plasma glucocorticoid inhibition is also higher than other corticosteroids inhalants (if high plasma corticosterone hormone levels are high ,the systemic side effects is high). Local side effects comparison table is as follows: Side effects of this product fluticasone propionate budesonide Dysphonia (hoarseness) 1.6% 4% 1%-8%-6% Sore throat 1.9% 10%-14% 5%-10% Thrush 0.2%-5% 2% 2%-4% The above information is edited by the lookchem of Tian Ye.

Uses

Treatment of asthma as prophylactic therapy in adults and adolescents.

InChI:InChI=1/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29+,30-,31-,32+/m0/s1

Upstream product

• 79-30-1 isobutyryl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 97-72-3 2-Methylpropionic anhydride 
• 91160-89-3 9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 77017-20-0 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 13951-70-7 desonide 
• 204444-44-0 16α,17-[(R,S)-cyclohexylmethylenedioxy]-11β,21-dihydroxypregna-1,4-dien-3,20-dione 
• 1451396-66-9 21-bromo-16α,17-[(R)-cyclohexylmethylenedioxy]-11β-hydroxypregna-1,4-dien-3,20-dione 
• 60154-69-0 tetrabutylammonium 2-methylpropionate 
• 61659-31-2 Tetramethylammonium Isobutyrate 
• 25179-23-1 lithium dimethylacetate 
• 19455-20-0 potassium isobutyrate 
• 996-30-5 isobutyric acid sodium salt 

Downstream Products

• 204444-45-1 ciclesonide 

Relevant articles and documents

Preparation method of ciclesonide

The invention discloses a preparation method of ciclesonide. The preparation method comprises the following steps: aldolization reaction, primary purification, hydrolysis reaction, esterification reaction and secondary purification. Aldolization reaction:

Ciclesonide preparation method

The invention discloses a ciclesonide preparation method, and belongs to the technical field of pharmacy, wherein 16[alpha]-hydroxyprednisolone-21-acetate (the previous-step intermediate of 16[alpha]-hydroxyprednisolone) is used as a starting raw material

Preparation method of ciclesonide

The invention provides a new synthetic route for preparation of ciclesonide. The method comprises the steps that used raw materials are cheaper and available, the reaction raw materials are protectedafter hydroxylation, selective oxidation of a five-membered ring double bond is then performed, then, a six-membered ring double bond bromination is conducted, bromine atom is removed by reduction, acarbonyl group and a hydroxyl protecting group are removed, then, an oxidized dihydroxyl group is protected, the six-membered ring double bond is then epoxidized and reacts with cyclohexanecarboxaldehyde and isobutyryl chloride in turn to obtain a ciclesonide product. A reaction process is easy to operate, yield is higher in each step, purity of the obtained product is also higher, generation of by-products is effectively avoided, production cost is reduced, and the new synthetic route for the preparation of the ciclesonide is advantageous to industrial production.

Pregnane derivatives 16, 17 - acetal (ketone) preparation method

Disclosed is a method for preparing a pregnane derivative 16,17-acetal (ketal) compound shown in the general formula I, the method comprising the step of reacting a compound of a general formula II with a compound of a general formula III or a general formula IV in the presence of boron trifluoride, wherein the dotted line between site 1 and site 2 denotes a saturated or unsaturated bond; R is hydroxyl, halogen or -OCOR7, wherein R7 is a C1-C12 linear chain or branched alkyl, a C3-C10 cycloalkyl, a C2-C8 alkenyl or a C2-C8 alkynyl; R1 and R2 are each hydrogen, a C1-C12 linear chain or branched alkyl, a C3-C10 cycloalkyl, a C2-C8 alkenyl or a C2-C8 alkynyl, or R1, R2 and the carbon to which they are connected form a C3-C10 cycloalkyl together, with the provision that R1 and R2 are not hydrogen simultaneously; R3 is hydrogen or -OCOR8, wherein R8 is a C1-C12 linear chain or branched alkyl, or a C3-C10 cycloalkyl; R4 is hydrogen, fluorine or chlorine; R5 is hydrogen, fluorine, chlorine or methyl; and R6 is a C1-C12 linear chain or branched alkyl. Compared with current processes, the method causes little pollution to the environment, has relatively mild reaction conditions, ease of control, reduced energy consumption and low production costs.

NOVEL PROCESS FOR PREPARATION OF GLUCOCORTICOID STEROIDS

The present invention discloses a process for the preparation of 16, 17-acetals of pregnane derivatives having formula (I) wherein each substituent is independently selected from; R1 is H or CH3; R2 is C1-C6 linear or branched alkyl, alkynyl group or cycloalkyl group; aryl or heteroaryl group; or R1 and R2 combine to form saturated, unsaturated C3-C6 cyclic or heterocyclic ring; R3 and R4 are same or different and each independently represents H or halogen; R5 is -OH or –OCOR wherein R represents H or C1-C6 linear, branched or cyclic alkyl group that may be substituted.

NOVEL METHOD FOR MANUFACTURING OF CICLESONIDE

The invention relates to a process for preparing ciclesonide in epimerically pure form, a corticosteroid of formula 1: Ciclesonide is used for the treatment of respiratory complaints.

NOVEL METHOD FOR MANUFACTURING OF CICLESONIDE

The invention relates to a process for preparing the corticosteroid ciclesonide, used for the treatment of respiratory complaints, in epimerically pure form of formula 1:

Crystalline Ciclesonide Methanol Solvate Form C

The present invention relates to crystalline ciclesonide methanol solvate Form C, processes for its preparation, its use in the synthesis of crystalline ciclesonide Form A and its use in medicine.

PROCESSES FOR THE PREPARATION OF CICLESONIDE AND ITS CRYSTAL MODIFICATION

Improved processes for the synthesis of ciclesonide, chemically termed as [11β,16α(R)]-16,17-[(cyclohexylmethylene)bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione and its crystal modification.

PROCESS FOR THE PREPARATION OF PREGNANE DERIVATIVES

A stereoselective and enrichment process for the preparation of ciclesonide is described.