249289-10-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(1-Hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamide is used as a starting material for the preparation of FTY 720-phosphate enantiomers, which are immunosuppressants. These enantiomers play a significant role in the development of medications that help suppress the immune system, making them useful in treating various autoimmune diseases and preventing organ transplant rejection.
Additionally, the unlabelled version of N-(1,1-Bis(hydroxymethyl)-3-(4-octylphenyl)propyl)acetamide-d4 (B445610) is utilized in the synthesis process, further contributing to the development of immunosuppressive drugs.

Upstream product

• 111-64-8 n-octanoic acid chloride 
• 1674-37-9 n-octanophenone 
• 71-43-2 benzene 
• 1620230-21-8 N-[1,1-bis(hydroxymethyl)-3-(4-octylphenyl)allyl]acetamide 
• 1620230-20-7 N-[1,1-bis(hydroxymethyl)-3chloro-(4-octylphenyl)propyl]acetamide 
• 10541-56-7 4-n-octylacetophenone 
• 122-79-2 Phenyl acetate 
• 268557-49-9 2-(acetylamino)-2-[2-(4-octylphenyl)-2-oxo-ethyl]propanedioic acid diethyl ester 
• 2189-60-8 Octylbenzene 
• 64068-76-4 α-bromomethyl p(n-octyl)phenyl cetone 
• 162358-07-8 2-(4-octylphenyl)-1-iodoethane 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 103-45-7 acetic acid phenethyl ester 
• 162358-08-9 diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate 

Downstream Products

• 162358-09-0 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate 
• 836608-95-8 (R)-2-Methyl-4-[2-(4-octyl-phenyl)-ethyl]-4,5-dihydro-oxazole-4-carbaldehyde 
• 836608-88-9 (S)-[2-methyl-4-[2-(4-octylphenyl)ethyl]oxazoline-4-yl]methanol 
• 856571-72-7 Acetic acid (R)-2-methyl-4-[2-(4-octyl-phenyl)-ethyl]-4,5-dihydro-oxazol-4-ylmethyl ester 
• 402616-26-6 (S)-fingolimod phosphate 
• 1262962-14-0 fingolimod hydrobromide 
• 162359-55-9 fingolimod 

Relevant academic research and scientific papers

A PROCESS FOR THE PREPARATION OF 2-AMINO-1,3-PROPANE DIOL COMPOUNDS AND SALTS THEREOF

The present disclosure relates to processes for the preparation of 2-amino-1,3-propane diol compounds and their hydrochloride salts. Particularly, the present disclosure relates to processes for synthesizing 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol and its hydrochloride salt 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride respectively. The said process is safe, commercially feasible for large-scale synthesis and has improved efficacy along with many other advantages. The present disclosure also relates to the novel polymorphs of 2-amino-1,3-propane diol compound and its hydrochloride salt, where in 2-amino-1,3-propane diol compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol, and its hydrochloride salt is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride.

Synthesis and evaluation of fluorinated fingolimod (FTY720) analogues for sphingosine-1-phosphate receptor molecular imaging by positron emission tomography

Sphingosine-1-phosphate (S1P) is a lysophospholipid that evokes a variety of biological responses via stimulation of a set of cognate G-protein coupled receptors (GPCRs): S1P1-S1P5. S1P and its receptors (S1PRs) play important roles in the immune, cardiovascular, and central nervous systems and have also been implicated in carcinogenesis. Recently, the S1P analogue Fingolimod (FTY720) has been approved for the treatment of patients with relapsing multiple sclerosis. This work presents the synthesis of various fluorinated structural analogues of FTY720, their in vitro and in vivo biological testing, and their development and application as [18F]radiotracers for the study of S1PR biodistribution and imaging in mice using small-animal positron emission tomography (PET).

INTERMEDIATES AND PROCESS FOR THE PREPARATION OF HIGH PURITY FINGOLIMOD HYDROCHLORIDE

The present invention relates to a simple and commercially feasible preparation of Fingolimod hydrochloride with high purity of greater than 99.9%. The.present invention also provides novel intermediates for the preparation of Fingolimod Hydrochloride of Formula 1.

PREPARATION OF FINGOLIMOD AND ITS SALTS

The present application provide processes for the preparation of fingolimod and its pharmaceutically acceptable salts, process for the purification of fingolimod hydrochloride and process for the preparation of amorphous fingolimod hydrochloride.

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

PROCESS FOR PRODUCING FINGOLIMOD SALTS

The invention relates to a process for producing pharmaceutically acceptable salts of fingolimod (I), comprising the step of reacting N-[1,1-bis hydroxymethyl-3-(4-octyl phenyl)-propyl]-acylamide (II) with an acidic compound. Furthermore, the invention provides different pharmaceutically acceptable salts of fingolimod and a polymorphic form of fingolimod hydrochloride.

PROCESS FOR PRODUCING FINGOLIMOD SALTS

The invention relates to a process for producing pharmaceutically acceptable salts of fingolimod (I), comprising the step of reacting N-[1,1-bis hydroxymethyl-3-(4-octyl phenyl)-propyl]-acylamide (II) with an acidic compound. Furthermore, the invention provides different pharmaceutically acceptable salts of fingolimod and a polymorphic form of fingolimod hydrochloride.

ORALLY AVAILABLE SPHINGOSINE 1-PHOSPHATE RECEPTOR AGONISTS AND ANTAGONISTS

The present invention relates to S1P analogs that have activity as S1Preceptor modulating agents and the use of such compounds to treat diseases associated with inappropriate S1P receptor activity. The compounds have the general structure (I) wherein R11 is C5-C18 alkyl or C5-C18 alkenyl; Q is selected from the group consisting of C3-C6 optionally substituted cycloalkyl, C3-C6 optionally substituted heterocyclic, C3-C6 optionally substituted aryl C3-C6 optionally substituted heteroaryl and; R2 is selected from the group consisting of H, C1-C4 alkyl, (C1-C4 alkyl)OH and (C1-C4 alkyl)NH2; R23 is H or C1-C4 alkyl, and R15 is a phosphonate ester or a phosphate ester or a pharmaceutically acceptable salt or tautomer thereof.

Synthesis and immunosuppressive activity of 2-substituted 2- aminopropane-1,3-diols and 2-aminoethanols

A series of 2-substituted 2-aminopropane-1,3-diols was synthesized and evaluated for their lymphocyte-decreasing effect and immunosuppressive effect on rat skin allograft. A phenyl ring was introduced into the alkyl chain of the lead compound 3, which is an immunosuppressive agent structurally simplified from myriocin (1, ISP-I) via compound 2. The potency of the various compounds was dependent upon the position of the phenyl ring within the alkyl side chain. The most suitable length between the quaternary carbon atom and the phenyl ring was two carbon atoms. 2-Substituted 2-aminoethanols were successively synthesized and evaluated for their T-cell-decreasing effect and immunosuppressive effect using a popliteal lymph node gain assay in rats. The absolute configuration at the quaternary carbon affected the activity, and the (pro-S)-hydroxymethyl group of compound 6 was essential for potent immunosuppressive activity. Favorable substituents for the (pro-R)- hydroxymethyl group of 6 were hydroxyalkyl (hydroxyethyl and hydroxypropyl) or lower alkyl (methyl and ethyl) groups. 2-Amino-2-[2-(4- octylphenyl)ethyl]propane-1,3-diol hydrochloride (6, FTY720) was found to possess considerable activity and is expected to be useful as an immunosuppressive drug for organ transplantation.