ECSP045514A - Método mejorado para preparar nevirapina - Google Patents
Método mejorado para preparar nevirapinaInfo
- Publication number
- ECSP045514A ECSP045514A EC2004005514A ECSP045514A ECSP045514A EC SP045514 A ECSP045514 A EC SP045514A EC 2004005514 A EC2004005514 A EC 2004005514A EC SP045514 A ECSP045514 A EC SP045514A EC SP045514 A ECSP045514 A EC SP045514A
- Authority
- EC
- Ecuador
- Prior art keywords
- cyclopropylamino
- halo
- bromine
- pyridinecarbonitrile
- methyl
- Prior art date
Links
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 title abstract 6
- 229960000689 nevirapine Drugs 0.000 title abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 6
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Chemical group 0.000 abstract 4
- QVDNJGOBMXAPSJ-UHFFFAOYSA-N 2-(cyclopropylazaniumyl)pyridine-3-carboxylate Chemical compound OC(=O)C1=CC=CN=C1NC1CC1 QVDNJGOBMXAPSJ-UHFFFAOYSA-N 0.000 abstract 3
- NQVWMXLKPISDFN-UHFFFAOYSA-N 2-(cyclopropylamino)pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1NC1CC1 NQVWMXLKPISDFN-UHFFFAOYSA-N 0.000 abstract 2
- FTBSSMUGIFVBDO-UHFFFAOYSA-N 2-(cyclopropylamino)pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1NC1CC1 FTBSSMUGIFVBDO-UHFFFAOYSA-N 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 229910052740 iodine Chemical group 0.000 abstract 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Un procedimiento para preparar nevirapina, que comprende las siguientes etapas:(a) hacer reaccionar un 2-halo-3-piridincarbonitrilo de la fórmula en donde X es un átomo de flúor, cloro, bromo o yodo, preferiblemente cloro o bromo, con ciclopropilamina para proporcionar 2-(ciclopropilamino)-3-piridincarbonitrilo;(b) hidrolizar el 2-(ciclopropilamino)-3-piridincarbonitrilo para proporcionar ácido 2-(ciclopropilamino)-3-piridina-carboxílico;(c) aislar el ácido 2-(ciclopropilamino)-3-piridina-carboxílico a partir del medio de reacción;(e) tratar el ácido 2-(ciclopropilamino)-3-piridina-carboxílico con un agente clorante para proporcionar cloruro de 2-(ciclopropilamino)-3-piridincarbonilo;(f) hacer reaccionar el cloruro de 2-(ciclopropilamino)-3-piridincarbonilo con una 2-halo-4-metil-3-piridinamina de la fórmula en donde X es un átomo de flúor, cloro, bromo o yodo, preferiblemente cloro o bromo, para producir una N-(2-halo-4-metil-3-piridinil)-2-(ciclopropilamino)-3-piridincarboxa-mida; y(g) ciclar la N-(2-halo-4-metil-3-piridinil)-2-(ciclopropilamino)-3-piridincarboxamida mediante tratamiento con una base fuerte, para proporcionar nevirapina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39269002P | 2002-06-28 | 2002-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ECSP045514A true ECSP045514A (es) | 2005-03-10 |
Family
ID=30000920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EC2004005514A ECSP045514A (es) | 2002-06-28 | 2004-12-27 | Método mejorado para preparar nevirapina |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6680383B1 (es) |
| EP (1) | EP1519936B1 (es) |
| JP (1) | JP4209388B2 (es) |
| KR (1) | KR100981261B1 (es) |
| CN (1) | CN1280293C (es) |
| AR (1) | AR039771A1 (es) |
| AT (1) | ATE382621T1 (es) |
| AU (1) | AU2003237336B2 (es) |
| BR (1) | BR0312071A (es) |
| CA (2) | CA2480046C (es) |
| DE (1) | DE60318444T2 (es) |
| DK (1) | DK1519936T3 (es) |
| EA (1) | EA007497B1 (es) |
| EC (1) | ECSP045514A (es) |
| ES (1) | ES2299709T3 (es) |
| HR (1) | HRP20041214A2 (es) |
| IL (1) | IL163977A0 (es) |
| ME (1) | MEP53908A (es) |
| MX (1) | MXPA04010405A (es) |
| MY (1) | MY131847A (es) |
| NO (1) | NO329109B1 (es) |
| NZ (1) | NZ537803A (es) |
| PE (1) | PE20040586A1 (es) |
| PL (1) | PL371496A1 (es) |
| RS (1) | RS50900B (es) |
| TW (1) | TWI270548B (es) |
| UA (1) | UA80140C2 (es) |
| WO (1) | WO2004002988A1 (es) |
| ZA (1) | ZA200407107B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007010352A1 (en) * | 2005-07-19 | 2007-01-25 | Emcure Pharmaceuticals Limited | An improved process for industrial manufacture of nevirapine |
| JP2007031391A (ja) * | 2005-07-29 | 2007-02-08 | Koei Chem Co Ltd | アルキルアミノピリジンカルボニトリルの製造方法 |
| CN102725293A (zh) * | 2009-12-17 | 2012-10-10 | 西北大学 | 奈韦拉平的多晶型形式及其制备 |
| CN102167699A (zh) * | 2011-03-17 | 2011-08-31 | 湖南博奥德生物医药技术开发有限公司 | 一种奈韦拉平制备方法 |
| WO2012168949A2 (en) * | 2011-06-06 | 2012-12-13 | Laurus Labs Private Limited | A process for preparation of nevirapine |
| CN102321015A (zh) * | 2011-06-30 | 2012-01-18 | 江苏德峰药业有限公司 | 一种抗艾滋病药物奈韦拉平关键中间体 2-(环丙胺基）-3-甲酸吡啶的制备方法 |
| WO2016118586A1 (en) * | 2015-01-20 | 2016-07-28 | Virginia Commonwealth University | Lowcost, high yield synthesis of nevirapine |
| CN116675640A (zh) * | 2023-06-02 | 2023-09-01 | 中科苏州药物研究院 | 一种奈伟拉平中间体2-（环丙基氨基）烟酸的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5366972A (en) | 1989-04-20 | 1994-11-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | 5,11-dihydro-6H-dipyrido(3,2-B:2',3'-E)(1,4)diazepines and their use in the prevention or treatment of HIV infection |
| DE4403311C1 (de) * | 1994-02-03 | 1995-04-20 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Nevirapine (11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4-diazepin]-6-on) |
-
2003
- 2003-02-06 UA UAA200500685A patent/UA80140C2/uk unknown
- 2003-06-02 WO PCT/US2003/017376 patent/WO2004002988A1/en not_active Ceased
- 2003-06-02 CA CA2480046A patent/CA2480046C/en not_active Expired - Fee Related
- 2003-06-02 CA CA2708442A patent/CA2708442C/en not_active Expired - Fee Related
- 2003-06-02 IL IL16397703A patent/IL163977A0/xx not_active IP Right Cessation
- 2003-06-02 PL PL03371496A patent/PL371496A1/xx not_active IP Right Cessation
- 2003-06-02 MX MXPA04010405A patent/MXPA04010405A/es active IP Right Grant
- 2003-06-02 ME MEP-539/08A patent/MEP53908A/xx unknown
- 2003-06-02 JP JP2004517609A patent/JP4209388B2/ja not_active Expired - Fee Related
- 2003-06-02 DE DE60318444T patent/DE60318444T2/de not_active Expired - Lifetime
- 2003-06-02 NZ NZ537803A patent/NZ537803A/en not_active IP Right Cessation
- 2003-06-02 AU AU2003237336A patent/AU2003237336B2/en not_active Ceased
- 2003-06-02 AT AT03736801T patent/ATE382621T1/de active
- 2003-06-02 HR HR20041214A patent/HRP20041214A2/xx not_active Application Discontinuation
- 2003-06-02 DK DK03736801T patent/DK1519936T3/da active
- 2003-06-02 EP EP03736801A patent/EP1519936B1/en not_active Expired - Lifetime
- 2003-06-02 BR BR0312071-6A patent/BR0312071A/pt not_active IP Right Cessation
- 2003-06-02 RS YUP-1102/04A patent/RS50900B/sr unknown
- 2003-06-02 KR KR1020047021296A patent/KR100981261B1/ko not_active Expired - Fee Related
- 2003-06-02 EA EA200401535A patent/EA007497B1/ru not_active IP Right Cessation
- 2003-06-02 CN CNB038105896A patent/CN1280293C/zh not_active Expired - Fee Related
- 2003-06-02 ES ES03736801T patent/ES2299709T3/es not_active Expired - Lifetime
- 2003-06-05 US US10/454,991 patent/US6680383B1/en not_active Expired - Lifetime
- 2003-06-26 PE PE2003000642A patent/PE20040586A1/es not_active Application Discontinuation
- 2003-06-27 AR ARP030102323A patent/AR039771A1/es unknown
- 2003-06-27 TW TW092117662A patent/TWI270548B/zh not_active IP Right Cessation
- 2003-06-27 MY MYPI20032417A patent/MY131847A/en unknown
-
2004
- 2004-09-06 ZA ZA200407107A patent/ZA200407107B/en unknown
- 2004-10-12 NO NO20044332A patent/NO329109B1/no not_active IP Right Cessation
- 2004-12-27 EC EC2004005514A patent/ECSP045514A/es unknown
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