AR080375A1 - Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 7-sulfonamida - Google Patents
Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 7-sulfonamidaInfo
- Publication number
- AR080375A1 AR080375A1 ARP110100673A ARP110100673A AR080375A1 AR 080375 A1 AR080375 A1 AR 080375A1 AR P110100673 A ARP110100673 A AR P110100673A AR P110100673 A ARP110100673 A AR P110100673A AR 080375 A1 AR080375 A1 AR 080375A1
- Authority
- AR
- Argentina
- Prior art keywords
- tetrahydroisoquinoline
- cyclohexylmethyl
- salt
- sulfonamide
- methylpyrrolidin
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 10
- UGVNTBVUSAJEOL-UHFFFAOYSA-N 2-(cyclohexylmethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1CC1CCCCC1 UGVNTBVUSAJEOL-UHFFFAOYSA-N 0.000 abstract 3
- KZNIWHNWWKFZKM-QFIPXVFZSA-N 2-(cyclohexylmethyl)-n-[2-[(2s)-1-methylpyrrolidin-2-yl]ethyl]-3,4-dihydro-1h-isoquinoline-7-sulfonamide Chemical compound CN1CCC[C@H]1CCNS(=O)(=O)C1=CC=C(CCN(CC2CCCCC2)C2)C2=C1 KZNIWHNWWKFZKM-QFIPXVFZSA-N 0.000 abstract 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 abstract 2
- YSNXWNDFMSZZKQ-UHFFFAOYSA-N 2-(cyclohexylmethyl)-3,4-dihydro-1h-isoquinoline-7-sulfonyl chloride Chemical compound C1C2=CC(S(=O)(=O)Cl)=CC=C2CCN1CC1CCCCC1 YSNXWNDFMSZZKQ-UHFFFAOYSA-N 0.000 abstract 2
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- PNHGJPJOMCXSKN-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanamine Chemical compound CN1CCCC1CCN PNHGJPJOMCXSKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
- A61P5/20—Drugs for disorders of the endocrine system of the parathyroid hormones for decreasing, blocking or antagonising the activity of PTH
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicacion 1: Un procedimiento para preparar 2-(ciclohexilmetil)-N-{2-[(2S)-1-metilpirrolidin-2-il]etil}-1,2,3,4-tetrahidroisoquinolina-7-sulfonamida, o una sal farmacéuticamente aceptable de la misma o un solvato o hidrato de una sal farmacéuticamente aceptable que comprende: a) la aminacion reductora de 1,2,3,4-tetrahidroisoquinolina, o una de sus sales, con ciclohexanocarboxaldehído para dar 2-ciclohexilmetil-1,2,3,4-tetrahidroisoquinolina, o una de sus sales; b) hacer reaccionar 2-ciclohexilmetil-1,2,3.4-tetrahidroisoquinolina, o una de sus sales, con un exceso de ácido clorosulfonico para dar la sal HX del cloruro de 2-ciclohexilmetil-1,2,3,4-tetrahidroisoquinolina-7-sulfonilo, y opcionalmente recristalizar la sal HX del cloruro de 2-ciclohexilmetil-1,2,3,4-tetrahidroisoquinolina-7-sulfonilo; c) acoplar la sal HX del cloruro de 2-ciclohexilmetil-1,2,3,4-tetrahidroisoquinolina-7-sulfonilo con (-)-2-(2-aminoetil)-1-metilpirrolidina para formar 2-(ciclohexilmetil)-N-{2-[(2S)-1-metilpirrolidin-2-il]etil}-1,2,3,4-tetrahidroisoquinolina-7-sulfonamida; d) hacer reaccionar opcionalmente 2-(ciclohexilmetil)-N-{2-[(2S)-1-metilpirrolidin-2-il]etil}-1,2,3,4-tetrahidroisoquinolina-7-sulfonamida con una cantidad estequiométrica o un exceso de un ácido formador de sal en un disolvente para formar una sal o un hidrato o solvato de la misma; y e) recristalizar opcionalmente el producto de la etapa d).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31106910P | 2010-03-05 | 2010-03-05 | |
| FR1059750 | 2010-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR080375A1 true AR080375A1 (es) | 2012-04-04 |
Family
ID=44012569
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110100673A AR080375A1 (es) | 2010-03-05 | 2011-03-03 | Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 7-sulfonamida |
| ARP110100672A AR080374A1 (es) | 2010-03-05 | 2011-03-03 | Procedimiento para la preparcion de 2-(ciclohexilmetil)-n-(2-((2s)-1-metilpirrolidin-2-il) etil)- 1,2,3,4-tetrahidroisoquinolin-7- sulfonamida |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110100672A AR080374A1 (es) | 2010-03-05 | 2011-03-03 | Procedimiento para la preparcion de 2-(ciclohexilmetil)-n-(2-((2s)-1-metilpirrolidin-2-il) etil)- 1,2,3,4-tetrahidroisoquinolin-7- sulfonamida |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US8748615B2 (es) |
| EP (2) | EP2556064B1 (es) |
| JP (2) | JP2013521308A (es) |
| KR (2) | KR101783679B1 (es) |
| CN (2) | CN103221394A (es) |
| AR (2) | AR080375A1 (es) |
| AU (2) | AU2011223560A1 (es) |
| BR (2) | BR112012022356A2 (es) |
| CA (2) | CA2787427C (es) |
| CL (2) | CL2012002452A1 (es) |
| CO (2) | CO6630129A2 (es) |
| CR (1) | CR20120467A (es) |
| DO (1) | DOP2012000228A (es) |
| EC (1) | ECSP12012207A (es) |
| GT (1) | GT201200228A (es) |
| IL (2) | IL221341A (es) |
| MA (2) | MA34142B1 (es) |
| MX (2) | MX2012009413A (es) |
| NZ (2) | NZ602009A (es) |
| PE (1) | PE20130007A1 (es) |
| PH (2) | PH12012501499A1 (es) |
| RU (2) | RU2012142310A (es) |
| SG (2) | SG182576A1 (es) |
| TN (1) | TN2012000361A1 (es) |
| TW (2) | TW201144285A (es) |
| UY (2) | UY33263A (es) |
| WO (2) | WO2011109680A2 (es) |
| ZA (1) | ZA201205311B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR080375A1 (es) | 2010-03-05 | 2012-04-04 | Sanofi Aventis | Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 7-sulfonamida |
| CN102816101A (zh) * | 2012-08-21 | 2012-12-12 | 江苏恒祥化工有限责任公司 | 一种(s)-n-甲基-2氯乙基吡咯烷的合成方法 |
| CN105764510A (zh) * | 2013-09-09 | 2016-07-13 | 赛诺菲 | H3受体拮抗剂与胆碱酶抑制剂组合用于阿尔茨海默氏病治疗中的用途 |
| US10590136B2 (en) * | 2017-10-04 | 2020-03-17 | Celgene Corporation | Processes for the preparation of cis-4-[2-{[(3S,4R)-3-fluorooxan-4-yl]amino}-8-(2,4,6-trichloroanilino)-9H-purin-9-yl]-1-methylcyclohexane-1-carboxamide |
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| DE102005015040A1 (de) | 2005-03-31 | 2006-10-05 | Sanofi-Aventis Deutschland Gmbh | Substituierte Tetrahydroisochinoline als MMP-Inhibitoren, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikament |
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| US7786137B2 (en) | 2005-05-10 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Bicyclic derivatives as modulators of ion channels |
| EP1911747A1 (en) | 2006-10-11 | 2008-04-16 | Laboratorios del Dr. Esteve S.A. | Sulfonamide substituted pyrazoline compounds, their preparation and use as CB1 modulators |
| JP5443975B2 (ja) | 2007-04-27 | 2014-03-19 | 富山化学工業株式会社 | 新規なスルホンアミド誘導体またはその塩 |
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| US20100305173A1 (en) | 2009-04-30 | 2010-12-02 | Concert Pharmaceuticals, Inc. | Hydroxyethylamino sulfonamide derivatives |
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