Ripasudil hydrochloride anhydrous

Base Information

• Chemical Name: Ripasudil hydrochloride anhydrous
• CAS No.: 223644-02-8
• Molecular Formula: C₁₅H₁₈FN₃O₂S*ClH
• Molecular Weight: 359.852
• UNII: 3CZ0FF0XJO
• Wikidata: Q27257045
• Mol file: 223644-02-8.mol

Synonyms:Ripasudil hydrochloride anhydrous;223644-02-8;ripasudil hydrochloride;UNII-3CZ0FF0XJO;3CZ0FF0XJO;ripasudil HCl;1H-1,4-Diazepine, 1-((4-fluoro-5-isoquinolinyl)sulfonyl)hexahydro-2-methyl-, monohydrochloride, (2S)-;Isoquinoline, 4-fluoro-5-(((2S)-hexahydro-2-methyl-1H-1,4-diazepin-1-yl)sulfonyl)-, hydrochloride (1:1);(S)-4-Fluoro-5-((2-methyl-1,4-diazepan-1-yl)sulfonyl)isoquinoline hydrochloride;4-fluoro-5-[[(2S)-2-methyl-1,4-diazepan-1-yl]sulfonyl]isoquinoline;hydrochloride;SCHEMBL3081946;RIPASUDIL HYDROCHLORIDE [MI];Q27257045

Chemical Property of Ripasudil hydrochloride anhydrous

Chemical Property:

• Melting Point: 258-259 °C (decomp)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 359.0870539
• Heavy Atom Count: 23
• Complexity: 482

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CNCCCN1S(=O)(=O)C2=CC=CC3=CN=CC(=C32)F.Cl
• Isomeric SMILES: C[C@H]1CNCCCN1S(=O)(=O)C2=CC=CC3=CN=CC(=C32)F.Cl
• Uses: Ripasudil (Glanatec TM, Kowa Pharmaceutical), a close derivative of fasudil, is another Rho kinase inhibitor approved in Japan at the end of 2014 for the treatment of glaucoma and ocular hypertensionwhen other therapeutic agents are not effective or cannot be administered. Additionally, ripasudil has been tested in diabetic retinopathy clinical trials and shown to promote corneal endothelial cell proliferation, endothelium regeneration, and wound healing. Ripasudil Hydrochloride Dihydrate is a derivative of fasudil and a rho kinase inhibitor (1,2). It is used for the treatment of glaucoma and ocular hypertension.

Technology Process of Ripasudil hydrochloride anhydrous

There total 8 articles about Ripasudil hydrochloride anhydrous which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-fluoroisoquinoline-5-sulfonyl chloride hydrochloride (906820-08-4) + tert-butyl (S)-3-methyl-1,4-diazepane-1-carboxylate (194032-32-1) → 4-fluoro-5-[[(2S)-hexahydro-2-methyl-1H-1,4-diazepin-1-yl]sulfonyl]isoquinoline hydrochloride (223644-02-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;

Reference yield: 96.0%

(S)-tert-butyl 4-[(4-fluoroisoquinoline-5-yl)sulfonyl]-3-methyl-1,4-diazepane-1-carboxylate (1360538-86-8) → 4-fluoro-5-[[(2S)-hexahydro-2-methyl-1H-1,4-diazepin-1-yl]sulfonyl]isoquinoline hydrochloride (223644-02-8)

Guidance literature:

With hydrogenchloride; In ethyl acetate; for 2h; Inert atmosphere; Cooling with ice;

Reference yield: 73.0%

(S)-4-fluoro-N-[1-(3-hydroxypropylamino)propan-2-yl]isoquinoline-5-sulfonamide oxalate → 4-fluoro-5-[[(2S)-hexahydro-2-methyl-1H-1,4-diazepin-1-yl]sulfonyl]isoquinoline hydrochloride (223644-02-8)

Guidance literature:

(S)-4-fluoro-N-[1-(3-hydroxypropylamino)propan-2-yl]isoquinoline-5-sulfonamide oxalate; With potassium carbonate; In dichloromethane; water; at 20 ℃; for 1h; Inert atmosphere; Large scale reaction;

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 25 ℃; for 0.5h; Inert atmosphere; Large scale reaction;

With hydrogenchloride; In water; acetone; at 5 - 15 ℃; Inert atmosphere; Large scale reaction;

DOI:10.3987/COM-11-12230

upstream raw materials:

ripasudil

4--fluoroisoquinoline

(S)-(-)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide

4-fluoroisoquinoline sulfate

Downstream raw materials:

ripasudil

Refernces

• 1、 -. "Refinement method of (s)-4-[(4-fluoroisoquinolyl-5-yl)sulfonyl]-3-methyl-1,4-diazacycloheptane hydrochloride". Paragraph 0042-0061. . Retrieved 2017/12/02.
• 2、 -. "(S)-(-)-1-(4-FLUOROISOQUINOLIN-5-YL)SULFONYL-2-METHYL-1,4-HOMOPIPERAZINE HYDROCHLORIDE DIHYDRATE". Page/Page column 5; 7-8. . Retrieved 2010/11/08.