AR068351A1 - Proceso para la obtencion de derivados de pirido (2,1-a) isoquinolina, formas cristalinas - Google Patents
Proceso para la obtencion de derivados de pirido (2,1-a) isoquinolina, formas cristalinasInfo
- Publication number
- AR068351A1 AR068351A1 ARP080103744A ARP080103744A AR068351A1 AR 068351 A1 AR068351 A1 AR 068351A1 AR P080103744 A ARP080103744 A AR P080103744A AR P080103744 A ARP080103744 A AR P080103744A AR 068351 A1 AR068351 A1 AR 068351A1
- Authority
- AR
- Argentina
- Prior art keywords
- pyrido
- isoquinolin
- fluoromethyl
- pyrrolidin
- dimethoxy
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Se refiere a dos formas cristalinas del diclorhidrato de la (2S,3S,11bS)-1-(2-amino-9, 10-dimetoxi-1, 3, 4, 6, 7, 11b-hexahidro-2H-pirido[2, 1-a]isoquinolin-3-il)-4(S)-fluormetil-pirrolidin-2-ona, que son la forma A y la forma B y a una forma amorfa de dicho compuesto. utiles para fabricar medicamentos para diabetes y/o trastornos de la tolerancia de glucosa. Reivindicacion 1: Proceso para la obtencion de un derivado de pirido-[2,1-a] isoquinolina de la formula 1 en la que R1, R2 y R3 son con independencia entre sí hidrogeno, halogeno, hidroxi, alquilo inferior, alcoxi interior o alquenilo inferior, dichos alquilo inferior, alcoxi inferior y alquenilo inferior pueden estar opcionalmente sustituidos por (alcoxi inferior) carbonilo, arilo o heterociclilo, y las sales farmacéuticamente. aceptables del mismo, que consiste en la desproteccion de un derivado de pirido[2,1-a]isoquinolina protegido sobre N de la formula 2 en la que R1, R2 y R3 tienen los significados definidos antes y R4 es un grupo protector de amina, con ácido clorhídrico, en un disolvente elegido entre el grupo formado por una cetona alifática, un nitrilo alifático, un éter cíclico o mezclas de los mismos, y agua mezclada con una cetona alifática, un nitrilo alifático, un éter cíclico o mezclas de los mismos. Reivindicacion 19: Una forma cristalina del diclorhidrato de la (2S,3S,11bS)-1-(2-amino-9,10-dimetoxi-1,3,4,6,7,11b-hexahi-dro-2H-pirido[2,1-a]isoquinolin-3-il)-4(S)-fluormetil-pirrolidin-2-ona caracterizada por un modelo de difraccion de rayos x del material en polvo obtenido por radiacion CUKalfa, que consta de los picos siguientes; 6,0 +- 0,2, 10,1 +- 0,2, 12,1 +- 0,2, 13,2 +- 0.2, 14,5 +- 0,2, 15,2 +- 0,2, 15,5 +- 0,2, 16,1 +- 0,2, 16,4 +- 0,2, 17,7 +- 0,2, 19,5 +- 0,2, 20,7 +- 0,2, 21,6 +- 0,2, 22,6 +- 0,2, 27,3 +- 0,2, 27,8 +- 0,2 y 30,2 +- 0,2 en (2-theta). Reivindicacion 20: Una forma cristalina del diclorhidrato de la (2S,3S,11bS)-1-(2-amino-9,10-dimetoxi-1,3,4,6,7,11b-hexahi-dro-2H-pirido[2,1-a]isoquinolin-3-il)-4(S)-fluormetil-pirrolidin-2-ona caracteriza por un espectro de absorcion IR que tiene los picos característicos expresados en cm-1 a aproximadamente: 3582 cm-1, 3440 cm-1, 3237 cm-1, 2726 cm-1, 2535 cm-1, 2477 cm-1, 1953 cm-1, 1681 cm-1, 1601 cm-1, 1575 cm-1, 1525 cm-1, 1491 cm-1, 1408 cm-1, 1308 cm-1, 1260 cm-1, 1225 cm-1, 1193 cm-1, 1145 cm-1, 1130 cm-1, 1096 cm-1, 1054 cm-1, 1000 cm-1, 967 cm-1, 946 cm-1, 879 cm-1 844 cm-1, 808 cm-1, 768 cm-1 y 654 cm-1. Reivindicacion 21: Una forma cristalina, solvato de DMF, del diclorhidrato de la (2S,3S,11bS)-1-(2-amino-9,10-dimetoxi-1,3,4,6, 7,11b-hexahidro-2H-pirido[2,1-a]isoquinolin-3-il)-4(S)-fluormetil-pirrolidin-2-ona caracterizada por un modelo de difraccion de rayos x del material en polvo con una radiacion CUKalfa que consta de los picos siguientes: 6,8 +- 0,2, 12,5 +- 0,2, 13,5 +- 0,2, 15,1 +- 0,2, 17,4 +- 0,2, 18,1 +- 0,2, 18,4 +- 0,2, 24,3 +- 0,2, 24,8 +- 0,2, 25,3 +- 0,2, 27,2 +- 0,2, 27,9 +- 0,2, 28,1 +- 0,2, 29,9 +- 0,2 y 30,7 +- 0,2 en (2-theta) Reivindicacion 22: Una forma cristalina, solvato de DMF, del di-clorhidrato de la (2S,3S,11bS)-1-(2-amino-9,10-dimetoxi-1,3,4,6,7,11b-hexahidro-2H-pirido[2, 1-a]isoquinolin-3-il)-4(S)-fluormetil-pirrolidin-2-ona caracterizada por un espectro de absorcion IR que tiene los siguientes picos característicos, expresados en cm-1 a aproximadamente: 3480 cm-1, 3376 cm-1, 2706 cm-1, 2682 cm-1, 2610 cm-1, 2574 cm-1, 2532 cm-1, 2381 cm-1, 1684 cm-1, 1659 cm-1, 1622 cm-1, 1574 cm-1, 1528 cm-1, 1487 cm-1, 1410 cm-1, 1383 cm-1, 1310 cm-1, 1267 cm-1, 1251 cm-1, 1229 cm-1, 1192 cm-1, 1135 cm-1, 1107 cm-1, 998 cm-1, 988 cm-1, 930 cm-1, 900 cm-1, 841 cm-1, 767 cm-1, 680 cm-1, y 667 cm-1. Reivindicacion 23: Forma amorfa del diclorhidrato de la (2S,3S,11bS)-1-(2-amino-9,10-dimetoxi-1,3,4,6,7,11b-hexahidro-2H-pirido-[2,1-a]isoquinolin-3-il)-4(S)-fluormetil-pirrolidin-2-ona caracterizada por un espectro de absorcion IR que tiene los siguientes picos característicos, expresados en cm-1 a aproximadamente: 3429 cm-1, 2507 cm-1, 1680 cm-1, 1612 cm-1, 1515 cm-1, 1310 cm-1, 1261 cm-1, 1246 cm-1, 1219 cm-1, 1127 cm-1, 994 cm-1, 964 cm-1, 945 cm-1, 888 cm-1, 860 cm-1, 842 cm-1, 767 cm-1, 685 cm-1 y 635 cm-1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07115302 | 2007-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR068351A1 true AR068351A1 (es) | 2009-11-11 |
Family
ID=39884345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080103744A AR068351A1 (es) | 2007-08-30 | 2008-08-28 | Proceso para la obtencion de derivados de pirido (2,1-a) isoquinolina, formas cristalinas |
Country Status (12)
| Country | Link |
|---|---|
| US (5) | US20090105480A1 (es) |
| EP (1) | EP2188286B1 (es) |
| JP (1) | JP5220860B2 (es) |
| CN (1) | CN101790531B (es) |
| AR (1) | AR068351A1 (es) |
| AT (1) | ATE554088T1 (es) |
| CA (1) | CA2696898A1 (es) |
| CL (1) | CL2008002532A1 (es) |
| ES (1) | ES2382716T3 (es) |
| PE (1) | PE20090956A1 (es) |
| TW (1) | TW200914450A (es) |
| WO (1) | WO2009027276A1 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| IN2015DN03795A (es) | 2012-10-24 | 2015-10-02 | Inserm Inst Nat De La Santé Et De La Rech Médicale | |
| US10426818B2 (en) | 2015-03-24 | 2019-10-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Method and pharmaceutical composition for use in the treatment of diabetes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1638970T3 (da) * | 2003-06-20 | 2011-01-03 | Hoffmann La Roche | Pyrid (2, 1-A)-isoquinolinderivater som DPP-IV-inhibitorer |
| CA2607927C (en) * | 2005-05-24 | 2014-12-30 | F. Hoffmann-La Roche Ag | Preparation of (s)-4-fluoromethyl-dihydro-furan-2-one |
| US7956201B2 (en) * | 2006-11-06 | 2011-06-07 | Hoffman-La Roche Inc. | Process for the preparation of (S)-4-fluoromethyl-dihydro-furan-2-one |
-
2008
- 2008-08-19 US US12/193,788 patent/US20090105480A1/en not_active Abandoned
- 2008-08-20 CA CA2696898A patent/CA2696898A1/en not_active Abandoned
- 2008-08-20 CN CN2008801047667A patent/CN101790531B/zh not_active Expired - Fee Related
- 2008-08-20 EP EP08787335A patent/EP2188286B1/en not_active Not-in-force
- 2008-08-20 WO PCT/EP2008/060865 patent/WO2009027276A1/en active Application Filing
- 2008-08-20 JP JP2010522318A patent/JP5220860B2/ja not_active Expired - Fee Related
- 2008-08-20 AT AT08787335T patent/ATE554088T1/de active
- 2008-08-20 ES ES08787335T patent/ES2382716T3/es active Active
- 2008-08-27 PE PE2008001448A patent/PE20090956A1/es not_active Application Discontinuation
- 2008-08-28 AR ARP080103744A patent/AR068351A1/es unknown
- 2008-08-28 CL CL2008002532A patent/CL2008002532A1/es unknown
- 2008-08-29 TW TW097133311A patent/TW200914450A/zh unknown
-
2012
- 2012-05-25 US US13/480,838 patent/US20120232273A1/en not_active Abandoned
-
2013
- 2013-09-13 US US13/969,817 patent/US20140046066A1/en not_active Abandoned
-
2014
- 2014-07-03 US US14/323,021 patent/US20140350257A1/en not_active Abandoned
-
2015
- 2015-05-01 US US14/702,035 patent/US20150336951A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090105480A1 (en) | 2009-04-23 |
| CN101790531A (zh) | 2010-07-28 |
| US20140350257A1 (en) | 2014-11-27 |
| EP2188286B1 (en) | 2012-04-18 |
| US20120232273A1 (en) | 2012-09-13 |
| EP2188286A1 (en) | 2010-05-26 |
| CA2696898A1 (en) | 2009-03-05 |
| PE20090956A1 (es) | 2009-07-13 |
| JP2010536916A (ja) | 2010-12-02 |
| US20140046066A1 (en) | 2014-02-13 |
| ES2382716T3 (es) | 2012-06-12 |
| JP5220860B2 (ja) | 2013-06-26 |
| TW200914450A (en) | 2009-04-01 |
| CN101790531B (zh) | 2013-06-19 |
| US20150336951A1 (en) | 2015-11-26 |
| CL2008002532A1 (es) | 2009-08-21 |
| WO2009027276A1 (en) | 2009-03-05 |
| ATE554088T1 (de) | 2012-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |