PE20090956A1 - PROCESO PARA LA OBTENCION DE DERIVADOS DE PIRIDO [2,1-a] - ISOQUINOLINA - Google Patents
PROCESO PARA LA OBTENCION DE DERIVADOS DE PIRIDO [2,1-a] - ISOQUINOLINAInfo
- Publication number
- PE20090956A1 PE20090956A1 PE2008001448A PE2008001448A PE20090956A1 PE 20090956 A1 PE20090956 A1 PE 20090956A1 PE 2008001448 A PE2008001448 A PE 2008001448A PE 2008001448 A PE2008001448 A PE 2008001448A PE 20090956 A1 PE20090956 A1 PE 20090956A1
- Authority
- PE
- Peru
- Prior art keywords
- formula
- methanosulphonyl
- pyrid
- isoquinoline
- mesilate
- Prior art date
Links
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229950002475 mesilate Drugs 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- CLNNBQDAAGDAHI-UHFFFAOYSA-N 6-chloro-1h-pyridin-2-one Chemical compound OC1=CC=CC(Cl)=N1 CLNNBQDAAGDAHI-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
REFERIDA A UN PROCEDIMIENTO PARA LA OBTENCION DE UN DERIVADO DE PIRIDO[2,1-a]ISOQUINOLINA DE FORMULA (I) QUE CONSISTE EN LA DESPROTECCION DE UN DERIVADO DE ISOQUINOLINA PROTEGIDO EN N DE FORMULA (II) CON ACIDO CLORHIDRICO, EN UN DISOLVENTE TAL COMO ACETONA, ACETONITRILO, TETRAHIDROFURANO O MEZCLAS DE LOS MISMOS, Y AGUA MEZCLADA CON ACETONA O TETRAHIDROFURANO, DONDE EL COMPUESTO DE FORMULA (II) SE OBTIENE MEDIANTE LA CONDENSACION DE UNA AMINA DE FORMULA (III) CON UNA FLUORLACTONA DE FORMULA (IV) EN PRESENCIA DE 6-CLOROPIRIDIN-2-OL COMO CATALIZADOR PARA FORMAR UNA BUTIRAMIDA DE FORMULA (V) QUE REACCIONA CON CLORURO DE METANOSULFONILO O ANHIDRIDO DE METANOSULFONILO PARA FORMAR UN MESILATO DE FORMULA (VI) CERRANDO EL ANILLO DEL MESILATO. R1, R2 Y R3 SON H, HALOGENO, ALQUILO, ALCOXI, ENTRE OTROS; R4 ES UN GRUPO AMINA PROTECTOR; Ms ES METANOSULFONILO. UN COMPUESTO DE FORMULA (I) PREPARADO CON DICHO PROCEDIMIENTO ES EL 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)-A(S)-FLUORMETIL-PIRROLIDIN-2-ONA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07115302 | 2007-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20090956A1 true PE20090956A1 (es) | 2009-07-13 |
Family
ID=39884345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2008001448A PE20090956A1 (es) | 2007-08-30 | 2008-08-27 | PROCESO PARA LA OBTENCION DE DERIVADOS DE PIRIDO [2,1-a] - ISOQUINOLINA |
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 |
| 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 |
| 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 |
| 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | 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 |
|---|---|---|---|---|
| AU2004251830B8 (en) * | 2003-06-20 | 2009-11-26 | F. Hoffmann-La Roche Ag | Pyrido[2, 1-A]-isoquinoline derivatives as DPP-IV inhibitors |
| CN101180282B (zh) * | 2005-05-24 | 2011-09-21 | 霍夫曼-拉罗奇有限公司 | （s）-4-氟甲基-二氢-呋喃-2-酮的制备 |
| 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 EP EP08787335A patent/EP2188286B1/en not_active Not-in-force
- 2008-08-20 AT AT08787335T patent/ATE554088T1/de active
- 2008-08-20 CN CN2008801047667A patent/CN101790531B/zh not_active Expired - Fee Related
- 2008-08-20 WO PCT/EP2008/060865 patent/WO2009027276A1/en not_active Ceased
- 2008-08-20 ES ES08787335T patent/ES2382716T3/es active Active
- 2008-08-20 JP JP2010522318A patent/JP5220860B2/ja not_active Expired - Fee Related
- 2008-08-27 PE PE2008001448A patent/PE20090956A1/es not_active Application Discontinuation
- 2008-08-28 CL CL2008002532A patent/CL2008002532A1/es unknown
- 2008-08-28 AR ARP080103744A patent/AR068351A1/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 |
|---|---|
| AR068351A1 (es) | 2009-11-11 |
| US20120232273A1 (en) | 2012-09-13 |
| US20140046066A1 (en) | 2014-02-13 |
| JP5220860B2 (ja) | 2013-06-26 |
| TW200914450A (en) | 2009-04-01 |
| CN101790531B (zh) | 2013-06-19 |
| CN101790531A (zh) | 2010-07-28 |
| WO2009027276A1 (en) | 2009-03-05 |
| ES2382716T3 (es) | 2012-06-12 |
| ATE554088T1 (de) | 2012-05-15 |
| CL2008002532A1 (es) | 2009-08-21 |
| JP2010536916A (ja) | 2010-12-02 |
| CA2696898A1 (en) | 2009-03-05 |
| EP2188286A1 (en) | 2010-05-26 |
| US20140350257A1 (en) | 2014-11-27 |
| US20150336951A1 (en) | 2015-11-26 |
| EP2188286B1 (en) | 2012-04-18 |
| US20090105480A1 (en) | 2009-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |