From Surf Wiki (app.surf) — the open knowledge base

Ramatroban

Chemical compound

Field	Value
IUPAC_name	3-((3R)-3-{[(4-fluorophenyl)sulfonyl]amino}-1,2,3,4-tetrahydro-9H-carbazol-9-yl)propanoic acid
image	Ramatroban.svg
image_class	skin-invert-image
tradename	Baynas
Drugs.com
routes_of_administration	Oral (tablets)
legal_status	Rx-only (JP)
CAS_number	116649-85-5
ATC_prefix	None
PubChem	123879
UNII_Ref
UNII	P1ALI72U6C
IUPHAR_ligand	1910
ChEMBL	361812
ChemSpiderID	110413
KEGG	D01128
C	21	H=21	F=1	N=2	O=4	S=1
smiles	C1CC2=C(CC1NS(=O)(=O)C3=CC=C(C=C3)F)C4=CC=CC=C4N2CCC(=O)O
StdInChI	1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1
StdInChIKey	LDXDSHIEDAPSSA-OAHLLOKOSA-N

| Drugs.com =

| elimination_half-life =

Ramatroban (INN; also known as BAY u3405) is a thromboxane receptor antagonist. It is also a DP2 receptor antagonist.

Ramatroban is indicated for the treatment of coronary artery disease. It has also been used for the treatment of asthma.

It has been suggested that ramatroban, by modulating DP2 receptor, can reverse viremia-associated proinflammatory and prothrombotic processes which are similar to those induced by SARS-Cov-2. Hence, ramatroban, that has been used for the treatment of allergic rhinitis in Japan for the past two decades with a well established safety profile, merits investigation as a novel immunotherapy for the treatment of COVID-19 disease, although no clinical trial has yet been conducted.

Ramatroban was developed by the German pharmaceutical company Bayer AG and is co-marketed in Japan by Bayer Yakuhin then marketed by Kyorin Pharmaceutical and Nippon Shinyaku Co., Ltd. under the trade name Baynas.

It is a tetrahydrocarbazolamine derivative and cyclized tryptamine.

Synthesis

The synthesis has been described: Cmp#4 Patent:

The starting material is called 1,4-cyclohexanedione monoethylene glycol ketal aka 1,4-Dioxaspiro[4.5]decan-8-one [4746-97-8]. The Borsche–Drechsel cyclization between (1) and Phenylhydrazine gives 5-Oxo-tetrahydrocarbazole ethylene ketal [54621-12-4] (2). Hydrolysis of the ketal protecting group gives 1,2,4,9-tetrahydrocarbazol-3-one [51145-61-0] (3). Reduction of the ketone with sodium borohydride gives 2,3,4,9-tetrahydro-1H-carbazol-3-ol [14384-34-0] (4). Acetylation by treatment with vinyl acetate [108-05-4] gives (3R)-3beta-Acetoxy-1,2,3,4-tetrahydro-9H-carbazole, PC59051734 (5a) & (3S)-1,2,3,4-Tetrahydro-9H-carbazole-3-ol, PC8142712 (5b). These can be separated at this stage into pure (S) for the next step. A Mitsunobu reaction in the presence of DPPA leads to an Azide with pure Walden inversion kinetics w/o racemization. The Staudinger reduction of the azide in situ gives (R)-3-Amino-1,2,3,4-tetrahydrocarbazole [874-937-6] [116650-33-0] (6).

References

"Ramatroban (compound)". National Center for Biotechnology Information.
(April 2003). "An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro". The Journal of Pharmacology and Experimental Therapeutics.
(September 2008). "A novel antagonist of prostaglandin D2 blocks the locomotion of eosinophils and basophils". European Journal of Clinical Investigation.
(December 1990). "Effects of the novel thromboxane antagonist Bay U 3405 on experimental coronary artery disease". Stroke.
(November 1996). "[Thromboxane A2 receptor antagonist in asthma therapy]". Nihon Rinsho. Japanese Journal of Clinical Medicine.
(September 2020). "Pharmaco-Immunomodulatory Therapy in COVID-19". Drugs.
(August 2012). "Synthesis of (R)-Ramatroban". Synfacts.
(May 2012). "Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases". The Journal of Organic Chemistry.
(December 1989). "Synthesis and absolute configuration of the new thromboxane antagonist (3R)-3-(4-fluorophenylsulfonamido)-1,2,3,4-tetrahydro-9-carbazolepropan oic acid and comparison with its enantiomer". Arzneimittel-Forschung.
(October 1957). "Formation of Dieckmann Reaction Products under Acyloin Conditions. Competition of the Two Reactions". The Journal of Organic Chemistry.
Horst Bohagen, et al. {{US patent. 5374647 (1994 to Bayer AG).

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

antiplatelet-drugs beta-amino-acids sulfonamides 4-fluorophenyl-compounds tetrahydrocarbazolamines

Want to explore this topic further?

Ask Mako anything about Ramatroban — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report