MEP53908A - Poboljšani postupak za pripremanje nevirapina - Google Patents
Poboljšani postupak za pripremanje nevirapinaInfo
- Publication number
- MEP53908A MEP53908A MEP-539/08A MEP53908A MEP53908A ME P53908 A MEP53908 A ME P53908A ME P53908 A MEP53908 A ME P53908A ME P53908 A MEP53908 A ME P53908A
- Authority
- ME
- Montenegro
- Prior art keywords
- cyclopropylamino
- bromine
- give
- pyridinecarbonitrile
- halo
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 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
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 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
Postupak za pripremanje nevirapina, koji sačinjavaju sledeći stupnjevi: (a) reakcija 2-halogeno-3-piridinkarbonitrila, formule (I), u kojoj X jeste, atom fluora, hlora, broma ili joda, prvenstveno hlora ili broma, sa ciklopropilaminom, radi dobijanja 2-(ciklopropilamino)-3- piridinkarbonitrila; (b) hidroliza 2-(ciklopropilamino)-3- piridinkarbonitrila, radi dobijanja 2-(ciklopropil-amino)-3-piridinkarboksilne kiseline; (c) izdvajanje 2-(ciklopropilamino)-3- piridinkarboksilne kiseline iz reakcione sredine; (d) tretiranje 2-(ciklopropilamino)-3- piridinkarboksilne kiseline sa nekim sredstvom za hlorovanje, radi dobijanja 2-(ciklopropilamino)-3- piridinkarbonil-hlorida; (e) reakcija 2-(ciklopropilamino)-3- piridinkarbonil-hlorida sa 2-halogeno-4-metil-3-piridaminom, formule (II), u kojoj X jeste, atom fluora, hlora, broma ili joda, prvenstveno hlora ili broma, radi dobijanja N-(2-halogeno-4-metil-3-piridinil)-2-(ciklopropilamino)-3-piridinkarboksamida, i (f) ciklizovanja N-(2-halogeno-4-metil-3-piridinil)-2-(ciklopropil-amino)-3-piridinkarboksamida, putem tretiranja sa nekom jakom bazom, radi dobijanja nevirapina. http://www.wipo.int/patentscope/search/en/docservice_fpimage/WOUS2003017376 false
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39269002P | 2002-06-28 | 2002-06-28 | |
| YUP-1102/04A RS50900B (sr) | 2002-06-28 | 2003-06-02 | Postupak za pripremanje nevirapina |
| PCT/US2003/017376 WO2004002988A1 (en) | 2002-06-28 | 2003-06-02 | Improved method of making nevirapine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MEP53908A true MEP53908A (bs) | 2011-05-10 |
Family
ID=30000920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-539/08A MEP53908A (bs) | 2002-06-28 | 2003-06-02 | Poboljšani postupak za pripremanje nevirapina |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6680383B1 (bs) |
| EP (1) | EP1519936B1 (bs) |
| JP (1) | JP4209388B2 (bs) |
| KR (1) | KR100981261B1 (bs) |
| CN (1) | CN1280293C (bs) |
| AR (1) | AR039771A1 (bs) |
| AT (1) | ATE382621T1 (bs) |
| AU (1) | AU2003237336B2 (bs) |
| BR (1) | BR0312071A (bs) |
| CA (2) | CA2708442C (bs) |
| DE (1) | DE60318444T2 (bs) |
| DK (1) | DK1519936T3 (bs) |
| EA (1) | EA007497B1 (bs) |
| EC (1) | ECSP045514A (bs) |
| ES (1) | ES2299709T3 (bs) |
| HR (1) | HRP20041214A2 (bs) |
| IL (1) | IL163977A0 (bs) |
| ME (1) | MEP53908A (bs) |
| MX (1) | MXPA04010405A (bs) |
| MY (1) | MY131847A (bs) |
| NO (1) | NO329109B1 (bs) |
| NZ (1) | NZ537803A (bs) |
| PE (1) | PE20040586A1 (bs) |
| PL (1) | PL371496A1 (bs) |
| RS (1) | RS50900B (bs) |
| TW (1) | TWI270548B (bs) |
| UA (1) | UA80140C2 (bs) |
| WO (1) | WO2004002988A1 (bs) |
| ZA (1) | ZA200407107B (bs) |
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 |
| BR112012014762A2 (pt) * | 2009-12-17 | 2016-03-29 | Univ Northwest | forma polimorfa de nevirapina e sua preparação |
| 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 DK DK03736801T patent/DK1519936T3/da active
- 2003-06-02 ES ES03736801T patent/ES2299709T3/es not_active Expired - Lifetime
- 2003-06-02 EA EA200401535A patent/EA007497B1/ru not_active IP Right Cessation
- 2003-06-02 ME MEP-539/08A patent/MEP53908A/bs unknown
- 2003-06-02 JP JP2004517609A patent/JP4209388B2/ja not_active Expired - Fee Related
- 2003-06-02 CA CA2708442A patent/CA2708442C/en not_active Expired - Fee Related
- 2003-06-02 BR BR0312071-6A patent/BR0312071A/pt not_active IP Right Cessation
- 2003-06-02 CN CNB038105896A patent/CN1280293C/zh not_active Expired - Fee Related
- 2003-06-02 RS YUP-1102/04A patent/RS50900B/sr unknown
- 2003-06-02 IL IL16397703A patent/IL163977A0/xx not_active IP Right Cessation
- 2003-06-02 DE DE60318444T patent/DE60318444T2/de not_active Expired - Lifetime
- 2003-06-02 WO PCT/US2003/017376 patent/WO2004002988A1/en not_active Ceased
- 2003-06-02 AT AT03736801T patent/ATE382621T1/de active
- 2003-06-02 PL PL03371496A patent/PL371496A1/xx not_active IP Right Cessation
- 2003-06-02 EP EP03736801A patent/EP1519936B1/en not_active Expired - Lifetime
- 2003-06-02 HR HR20041214A patent/HRP20041214A2/xx not_active Application Discontinuation
- 2003-06-02 KR KR1020047021296A patent/KR100981261B1/ko not_active Expired - Fee Related
- 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 MX MXPA04010405A patent/MXPA04010405A/es active IP Right Grant
- 2003-06-02 CA CA2480046A patent/CA2480046C/en not_active Expired - Fee Related
- 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 MY MYPI20032417A patent/MY131847A/en unknown
- 2003-06-27 TW TW092117662A patent/TWI270548B/zh not_active IP Right Cessation
-
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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