AR077469A2 - Proceso para preparar la forma 1 de efavirenz cristalino - Google Patents
Proceso para preparar la forma 1 de efavirenz cristalinoInfo
- Publication number
- AR077469A2 AR077469A2 ARP100102491A ARP100102491A AR077469A2 AR 077469 A2 AR077469 A2 AR 077469A2 AR P100102491 A ARP100102491 A AR P100102491A AR P100102491 A ARP100102491 A AR P100102491A AR 077469 A2 AR077469 A2 AR 077469A2
- Authority
- AR
- Argentina
- Prior art keywords
- thf
- efavirenz
- crystalline
- concentration
- heptane solution
- Prior art date
Links
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 title abstract 10
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 title abstract 10
- 229960003804 efavirenz Drugs 0.000 title abstract 10
- 238000000034 method Methods 0.000 title abstract 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 12
- 238000004519 manufacturing process Methods 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- 238000000113 differential scanning calorimetry Methods 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 238000001757 thermogravimetry curve Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Un proceso para preparar forma 1 de Efavirenz cristalino, donde el proceso comprende: 1) cristalizar la forma 4 de Efavirenz cristalino a partir de una solucion de THF/heptano donde la solucion de THF/heptano presenta una concentracion de aproximadamente 5% de THF y se reduce a una concentracion de alrededor de 1% de THF y 2) calentar la forma 4 de Efavirenz cristalino a una temperatura de aproximadamente 80°C a aproximadamente 100°C. Reivindicacion 2: Un proceso para preparar la forma 1 de Efavirenz cristalino, caracterizado porque presenta un patron de difraccion de partículas por rayos X que comprende cuatro o más valores seleccionados del grupo formado por: 6,0 +- 0,2; 6,3 +- 0,2; 10,3 +- 0,2; 10,8 +- 0,2; 14,1 +- 0,2; 16,8 +- 0,2; 20,0 +- 0,2; 20,5 +- 0,2; 21,1 +- 0,2; y 24,8 +- 0,2, donde el proceso comprende: 1) cristalizar la forma 4 de Efavirenz cristalino a partir de una solucion de THF/heptano donde la solucion de THF/heptano presenta una concentracion de aproximadamente 5% de THF y se reduce a una concentracion de alrededor de 1% de THF y 2) calentar la forma 4 de Efavirenz cristalino a una temperatura de aproximadamente 80°C a aproximadamente 100°C. Reivindicacion 3: Un proceso para preparar la forma 1 de Efavirenz cristalino, caracterizado porque presenta un termograma de calorimetría diferencial de barrido que presenta un pico en aproximadamente 138sC a 140°C, donde el proceso comprende: 1) cristalizar la forma 4 de Efavirenz cristalino a partir de una solucion de THF/heptano donde la solucion de THF/heptano presenta una concentracion de aproximadamente 5% de THF y se reduce a una concentracion de alrededor de 1% de THF y 2) calentar la forma 4 de Efavirenz cristalino a una temperatura de aproximadamente 80°C a aproximadamente 100°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8898198P | 1998-06-11 | 1998-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR077469A2 true AR077469A2 (es) | 2011-08-31 |
Family
ID=22214647
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP990102809A AR018670A1 (es) | 1998-06-11 | 1999-06-11 | Compuesto cristalino (s)-6-cloro-4-ciclopropiletinil-4-trifluormetil-1,4-dihidro-2h-3,1-benzoxacin-2-ona (efavirenz) en sus formas 1 a 5 y composicion farmaceutica que lo contiene |
| ARP100102490A AR077407A2 (es) | 1998-06-11 | 2010-07-08 | Forma 5 de efavirenz cristalino, proceso para obtenerla y metodos de uso |
| ARP100102491A AR077469A2 (es) | 1998-06-11 | 2010-07-08 | Proceso para preparar la forma 1 de efavirenz cristalino |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP990102809A AR018670A1 (es) | 1998-06-11 | 1999-06-11 | Compuesto cristalino (s)-6-cloro-4-ciclopropiletinil-4-trifluormetil-1,4-dihidro-2h-3,1-benzoxacin-2-ona (efavirenz) en sus formas 1 a 5 y composicion farmaceutica que lo contiene |
| ARP100102490A AR077407A2 (es) | 1998-06-11 | 2010-07-08 | Forma 5 de efavirenz cristalino, proceso para obtenerla y metodos de uso |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1086087A1 (es) |
| JP (1) | JP2002517487A (es) |
| CN (1) | CN1307568A (es) |
| AR (3) | AR018670A1 (es) |
| AU (1) | AU758114C (es) |
| BR (1) | BR9911523A (es) |
| CA (1) | CA2333550A1 (es) |
| EE (1) | EE05547B1 (es) |
| HR (1) | HRP990182A2 (es) |
| HU (1) | HUP0103819A3 (es) |
| IL (1) | IL139793A (es) |
| MY (1) | MY126450A (es) |
| NO (1) | NO20006255L (es) |
| NZ (1) | NZ507713A (es) |
| PL (1) | PL198504B1 (es) |
| SG (3) | SG111981A1 (es) |
| SK (1) | SK18182000A3 (es) |
| TW (1) | TWI235152B (es) |
| UA (1) | UA74324C2 (es) |
| WO (1) | WO1999064405A1 (es) |
| ZA (1) | ZA200006173B (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5965729A (en) | 1997-02-05 | 1999-10-12 | Merck & Co., Inc. | Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent |
| US20060235008A1 (en) | 2004-08-19 | 2006-10-19 | Hetero Drugs Limited | Novel polymorphs of efavirenz |
| US7205402B2 (en) * | 2004-09-02 | 2007-04-17 | Bristol-Myers Squibb Company | Synthesis of a benzoxazinone |
| WO2008108630A1 (en) * | 2007-03-02 | 2008-09-12 | Ultimorphix Technologies B.V. | Polymorphic forms of efavirenz |
| WO2009011567A1 (en) * | 2007-07-16 | 2009-01-22 | Ultimorphix Technologies B.V. | Crystalline forms of efavirenz |
| US8222273B2 (en) * | 2008-02-04 | 2012-07-17 | Pfizer Limited | Polymorphic form of a [1,2,4]triazole[4,3-A] pyridine derivative inflammatory diseases |
| US8383811B2 (en) | 2008-12-22 | 2013-02-26 | Hetero Research Foundation | Process for preparing efavirenz polymorph |
| DE102009041443A1 (de) | 2009-09-16 | 2011-03-31 | Archimica Gmbh | Salze des 6-Chlor-4-(cyclopropylethinyl)-1,4-dihydro-4-(trifluormethyl)-2H-3,1-benzoxazin-2-ons und deren Synthese, Aufreinigung und Anwendung als Vorstufen für Efavirenz |
| EP2471783A1 (en) | 2010-12-23 | 2012-07-04 | Esteve Química, S.A. | Novel polymorphic form of efavirenz |
| CN103508973B (zh) * | 2012-06-25 | 2016-04-27 | 上海迪赛诺药业有限公司 | 制备依非韦伦i型结晶的方法 |
| CN102924398B (zh) * | 2012-11-22 | 2015-11-18 | 安徽贝克生物制药有限公司 | 用于除去依非韦伦对应异构体的方法 |
| CA2898145C (en) * | 2013-01-23 | 2021-08-31 | Alienor Farma | Increased dosage of efavirenz for the treatment of cancer |
| CN105037175B (zh) * | 2014-07-18 | 2017-02-22 | 盐城迪赛诺制药有限公司 | 一种用于提高依非韦伦中间体光学纯度的方法 |
| CN105001101B (zh) * | 2015-05-28 | 2017-11-28 | 乐平市瑞盛制药有限公司 | 一种4‑氯‑2‑三氟乙酰基苯胺水合物盐酸盐的合成方法 |
| CN108947855B (zh) * | 2018-08-10 | 2021-10-22 | 江苏沙星化工有限公司 | 一种依非韦伦关键中间体的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL106507A (en) * | 1992-08-07 | 1997-11-20 | Merck & Co Inc | Pharmaceutical compositions containing benzoxazinones and some novel compounds of this type |
| AU1694295A (en) * | 1994-01-28 | 1995-08-15 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
| US5633405A (en) * | 1995-05-25 | 1997-05-27 | Merck & Co., Inc. | Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxanzin-2-one |
| AU3736197A (en) * | 1996-07-26 | 1998-02-20 | Du Pont Pharmaceuticals Company | A practical synthesis of benzoxazinones useful as hiv reverse transcripta se inhibitors |
| WO1998014436A1 (en) * | 1996-10-02 | 1998-04-09 | Dupont Pharmaceuticals Company | 4,4-disubstituted-1,4-dihydro-2h-3,1-benzoxazin-2-ones useful as hiv reverse transcriptase inhibitors and intermediates and processes for making the same |
| KR100573192B1 (ko) * | 1997-02-05 | 2006-04-24 | 머크 앤드 캄파니 인코포레이티드 | 역-용매를 사용한 역전사효소 억제제의 결정화 방법 및 당해 역전사효소 억제제의 결정형 |
-
1999
- 1999-06-08 HR HR60/088,981A patent/HRP990182A2/hr not_active Application Discontinuation
- 1999-06-10 NZ NZ507713A patent/NZ507713A/en not_active IP Right Cessation
- 1999-06-10 CN CN99807219A patent/CN1307568A/zh active Pending
- 1999-06-10 SG SG200207221A patent/SG111981A1/en unknown
- 1999-06-10 SG SG200207220A patent/SG111980A1/en unknown
- 1999-06-10 PL PL345221A patent/PL198504B1/pl unknown
- 1999-06-10 UA UA2000127048A patent/UA74324C2/uk unknown
- 1999-06-10 JP JP2000553414A patent/JP2002517487A/ja active Pending
- 1999-06-10 BR BR9911523-9A patent/BR9911523A/pt not_active Application Discontinuation
- 1999-06-10 HU HU0103819A patent/HUP0103819A3/hu unknown
- 1999-06-10 AU AU44364/99A patent/AU758114C/en not_active Expired
- 1999-06-10 WO PCT/US1999/013199 patent/WO1999064405A1/en not_active Ceased
- 1999-06-10 CA CA002333550A patent/CA2333550A1/en not_active Abandoned
- 1999-06-10 IL IL139793A patent/IL139793A/en not_active IP Right Cessation
- 1999-06-10 SK SK1818-2000A patent/SK18182000A3/sk unknown
- 1999-06-10 EE EEP200000743A patent/EE05547B1/xx unknown
- 1999-06-10 MY MYPI99002384A patent/MY126450A/en unknown
- 1999-06-10 EP EP99927468A patent/EP1086087A1/en not_active Withdrawn
- 1999-06-10 SG SG200207226-2A patent/SG134977A1/en unknown
- 1999-06-11 AR ARP990102809A patent/AR018670A1/es not_active Application Discontinuation
- 1999-07-03 TW TW088109817A patent/TWI235152B/zh not_active IP Right Cessation
-
2000
- 2000-10-31 ZA ZA200006173A patent/ZA200006173B/xx unknown
- 2000-12-08 NO NO20006255A patent/NO20006255L/no not_active Application Discontinuation
-
2010
- 2010-07-08 AR ARP100102490A patent/AR077407A2/es not_active Application Discontinuation
- 2010-07-08 AR ARP100102491A patent/AR077469A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL345221A1 (en) | 2001-12-03 |
| BR9911523A (pt) | 2001-09-18 |
| PL198504B1 (pl) | 2008-06-30 |
| AU758114C (en) | 2003-10-30 |
| NO20006255D0 (no) | 2000-12-08 |
| UA74324C2 (uk) | 2005-12-15 |
| AR077407A2 (es) | 2011-08-24 |
| NZ507713A (en) | 2003-08-29 |
| SG134977A1 (en) | 2007-09-28 |
| SG111981A1 (en) | 2005-06-29 |
| AU758114B2 (en) | 2003-03-13 |
| MY126450A (en) | 2006-10-31 |
| HRP990182A2 (en) | 2000-02-29 |
| CA2333550A1 (en) | 1999-12-16 |
| IL139793A0 (en) | 2002-02-10 |
| IL139793A (en) | 2006-10-31 |
| HUP0103819A2 (hu) | 2002-02-28 |
| ZA200006173B (en) | 2001-10-31 |
| AU4436499A (en) | 1999-12-30 |
| TWI235152B (en) | 2005-07-01 |
| CN1307568A (zh) | 2001-08-08 |
| EE200000743A (et) | 2002-10-15 |
| AR018670A1 (es) | 2001-11-28 |
| JP2002517487A (ja) | 2002-06-18 |
| SG111980A1 (en) | 2005-06-29 |
| EE05547B1 (et) | 2012-06-15 |
| WO1999064405A1 (en) | 1999-12-16 |
| NO20006255L (no) | 2001-02-12 |
| SK18182000A3 (sk) | 2001-08-06 |
| EP1086087A1 (en) | 2001-03-28 |
| HUP0103819A3 (en) | 2003-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |