AR039169A1 - Metodos para preparar 2-(7-cloro-1,8-naftiridin-2-il)-3-(5-metil-2-oxohexil)-1-isoindolinona - Google Patents
Metodos para preparar 2-(7-cloro-1,8-naftiridin-2-il)-3-(5-metil-2-oxohexil)-1-isoindolinonaInfo
- Publication number
- AR039169A1 AR039169A1 ARP030101080A ARP030101080A AR039169A1 AR 039169 A1 AR039169 A1 AR 039169A1 AR P030101080 A ARP030101080 A AR P030101080A AR P030101080 A ARP030101080 A AR P030101080A AR 039169 A1 AR039169 A1 AR 039169A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- methyl
- reacting
- isoindolinone
- oxohexil
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- -1 5-methyl-2-oxohexyl Chemical class 0.000 abstract 3
- PYTNPSPLGMPZKM-UHFFFAOYSA-N 1-hydroxy-3h-indol-2-one Chemical compound C1=CC=C2N(O)C(=O)CC2=C1 PYTNPSPLGMPZKM-UHFFFAOYSA-N 0.000 abstract 2
- NSPQTGOJGZXAJM-UHFFFAOYSA-N 7-amino-1h-1,8-naphthyridin-2-one Chemical compound C1=CC(=O)NC2=NC(N)=CC=C21 NSPQTGOJGZXAJM-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- HIUPRQPBWVEQJJ-UHFFFAOYSA-N pagoclone Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CC=C4C3=O)CC(=O)CCC(C)C)=CC=C21 HIUPRQPBWVEQJJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 abstract 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 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
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Reivindicación 1: Un método para preparar 2-(7-cloro-1,8-naftiridin-2-il)-3-(5-metil-2-oxohexil)-1-isoindolinona racémica, caracterizado porque el método comprende estos pasos: a) hacer reaccionar 2,6-diaminopiridina con ácido málico y ácido sulfúrico para formar la sal del ácido sulfúrico y 2-amino-7-hidroxi-1,8-naftiridina; b) hacer reaccionar la sal del ácido sulfúrico y 2-amino-7-hidroxi-1,8-naftiridina con un reactivo de ftaloilo en un disolvente para formar la ftalimidilnaftiridina de la fórmula (1); c) hacer reaccionar la ftalimidilnaftiridina de fórmula (1) con un agente de cloración para formar el cloruro de fórmula (2); d) hacer reaccionar el cloruro de fórmula (2) con un agente reductor para formar la hidroxiindolinona de fórmula (3); y e) hacer reaccionar la hidroxiindolinona de fórmula (3) con un derivado de 5-metil-2-oxohexilo para formar la 2-(7-cloro-1,8-naftiridin-2-il)-3-(5-metil-2-oxohexil)-1-isoindolinona racémica.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36860902P | 2002-03-29 | 2002-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR039169A1 true AR039169A1 (es) | 2005-02-09 |
Family
ID=28675512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030101080A AR039169A1 (es) | 2002-03-29 | 2003-03-27 | Metodos para preparar 2-(7-cloro-1,8-naftiridin-2-il)-3-(5-metil-2-oxohexil)-1-isoindolinona |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US6949653B2 (es) |
| EP (1) | EP1490363B1 (es) |
| JP (1) | JP4471664B2 (es) |
| AR (1) | AR039169A1 (es) |
| AT (1) | ATE316530T1 (es) |
| AU (1) | AU2003212585B2 (es) |
| CA (1) | CA2480776C (es) |
| CY (1) | CY1105785T1 (es) |
| DE (1) | DE60303363T2 (es) |
| DK (1) | DK1490363T3 (es) |
| ES (1) | ES2256723T3 (es) |
| IL (2) | IL164377A0 (es) |
| NZ (1) | NZ535685A (es) |
| PT (1) | PT1490363E (es) |
| RU (1) | RU2318823C2 (es) |
| TW (1) | TWI237639B (es) |
| WO (1) | WO2003082870A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1490363T3 (da) * | 2002-03-29 | 2006-05-15 | Indevus Pharmaceuticals Inc | Fremgangsmåder til fremstilling af 2-7-chlor-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxo-hexyl)1-isoindolinon |
| CN109988164B (zh) * | 2017-12-31 | 2021-12-07 | 中国医学科学院药物研究所 | 盐酸小檗碱与苹果酸共晶物及制备方法和其组合物与用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR208414A1 (es) | 1974-11-07 | 1976-12-27 | Rhone Poulenc Ind | Procedimiento para obtener nuevos derivados de la((acil-4piperazinil-1)carboniloxi-5 pirrolinona-2) |
| FR2607503B1 (fr) | 1986-12-02 | 1989-02-24 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5532228A (en) * | 1990-02-06 | 1996-07-02 | Schering Aktiengesellschaft | Side-chain homologous vitamin D derivatives, process for their production, pharmaceutical preparations containing these derivatives and their use as pharmaceutical agents |
| FR2678934B1 (fr) | 1991-07-12 | 1995-01-13 | Rhone Poulenc Rorer Sa | Procede de preparation de l'isomere dextrogyre d'un derive de l'isoindolinone. |
| FR2678932B1 (fr) | 1991-07-12 | 1993-09-24 | Rhone Poulenc Rorer Sa | Procede de preparation des isomeres optiques d'un derive de l'amino-2 naphtyridine. |
| FR2678933B1 (fr) | 1991-07-12 | 1993-09-24 | Rhone Poulenc Rorer Sa | Procede de preparation des isomeres optiques d'un derive de l'amino-2 naphtyridine. |
| FR2681068B1 (fr) | 1991-09-09 | 1993-11-19 | Rhone Poulenc Rorer Sa | Procede de preparation de l'isomere dextrogyre d'un derive de l'isoindolinone. |
| FR2684673B1 (fr) | 1991-12-04 | 1994-01-21 | Rhone Poulenc Rorer Sa | Procede de preparation d'un derive de l'amino-2 naphtyridine racemique. |
| FR2685330B1 (fr) | 1991-12-20 | 1994-02-04 | Rhone Poulenc Rorer Sa | Procede de preparation des enantiomeres d'un derive de l'isoindolinone. |
| FR2687154B1 (fr) | 1992-02-07 | 1995-05-12 | Rhone Poulenc Rorer Sa | Nouveau derive de l'isoindolinone, sa preparation et les compositions pharmaceutiques qui le contiennent. |
| FR2695389B1 (fr) | 1992-09-08 | 1994-11-04 | Rhone Poulenc Rorer Sa | Nouveau dérivé de l'isoindolinone, sa préparation et les compositions pharmaceutiques qui le contiennent. |
| US5498716A (en) | 1994-01-12 | 1996-03-12 | Rhone-Poulenc Rorer S.A. | 2-amino naphthyridine derivative, its preparation and its use |
| DK1490363T3 (da) * | 2002-03-29 | 2006-05-15 | Indevus Pharmaceuticals Inc | Fremgangsmåder til fremstilling af 2-7-chlor-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxo-hexyl)1-isoindolinon |
-
2003
- 2003-03-17 DK DK03708410T patent/DK1490363T3/da active
- 2003-03-17 PT PT03708410T patent/PT1490363E/pt unknown
- 2003-03-17 EP EP03708410A patent/EP1490363B1/en not_active Expired - Lifetime
- 2003-03-17 DE DE60303363T patent/DE60303363T2/de not_active Expired - Lifetime
- 2003-03-17 AU AU2003212585A patent/AU2003212585B2/en not_active Ceased
- 2003-03-17 RU RU2004131835/04A patent/RU2318823C2/ru not_active IP Right Cessation
- 2003-03-17 NZ NZ535685A patent/NZ535685A/en not_active IP Right Cessation
- 2003-03-17 IL IL16437703A patent/IL164377A0/xx unknown
- 2003-03-17 WO PCT/IB2003/001141 patent/WO2003082870A1/en active IP Right Grant
- 2003-03-17 JP JP2003580335A patent/JP4471664B2/ja not_active Expired - Fee Related
- 2003-03-17 ES ES03708410T patent/ES2256723T3/es not_active Expired - Lifetime
- 2003-03-17 CA CA2480776A patent/CA2480776C/en not_active Expired - Fee Related
- 2003-03-17 AT AT03708410T patent/ATE316530T1/de active
- 2003-03-24 TW TW092106529A patent/TWI237639B/zh not_active IP Right Cessation
- 2003-03-27 AR ARP030101080A patent/AR039169A1/es not_active Application Discontinuation
- 2003-03-27 US US10/400,780 patent/US6949653B2/en not_active Expired - Lifetime
-
2004
- 2004-10-03 IL IL164377A patent/IL164377A/en not_active IP Right Cessation
-
2005
- 2005-08-18 US US11/206,144 patent/US7057047B2/en not_active Expired - Lifetime
-
2006
- 2006-04-13 CY CY20061100511T patent/CY1105785T1/el unknown
- 2006-04-27 US US11/411,952 patent/US7304158B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL164377A (en) | 2011-07-31 |
| EP1490363A1 (en) | 2004-12-29 |
| WO2003082870A1 (en) | 2003-10-09 |
| ATE316530T1 (de) | 2006-02-15 |
| DE60303363T2 (de) | 2006-10-12 |
| US20060194830A1 (en) | 2006-08-31 |
| TW200305406A (en) | 2003-11-01 |
| US7304158B2 (en) | 2007-12-04 |
| AU2003212585B2 (en) | 2009-02-26 |
| CA2480776C (en) | 2010-11-23 |
| JP4471664B2 (ja) | 2010-06-02 |
| US20030191315A1 (en) | 2003-10-09 |
| US6949653B2 (en) | 2005-09-27 |
| RU2004131835A (ru) | 2005-07-10 |
| EP1490363B1 (en) | 2006-01-25 |
| DK1490363T3 (da) | 2006-05-15 |
| IL164377A0 (en) | 2005-12-18 |
| AU2003212585A1 (en) | 2003-10-13 |
| DE60303363D1 (de) | 2006-04-13 |
| RU2318823C2 (ru) | 2008-03-10 |
| NZ535685A (en) | 2007-04-27 |
| ES2256723T3 (es) | 2006-07-16 |
| CY1105785T1 (el) | 2011-02-02 |
| PT1490363E (pt) | 2006-06-30 |
| TWI237639B (en) | 2005-08-11 |
| US7057047B2 (en) | 2006-06-06 |
| CA2480776A1 (en) | 2003-10-09 |
| US20050288322A1 (en) | 2005-12-29 |
| JP2005528369A (ja) | 2005-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed, e.g., due to non-payment of fee |