AR052870A1 - Sintesis de analogos de himbacina - Google Patents
Sintesis de analogos de himbacinaInfo
- Publication number
- AR052870A1 AR052870A1 ARP060100125A ARP060100125A AR052870A1 AR 052870 A1 AR052870 A1 AR 052870A1 AR P060100125 A ARP060100125 A AR P060100125A AR P060100125 A ARP060100125 A AR P060100125A AR 052870 A1 AR052870 A1 AR 052870A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- alkyl
- defined above
- group
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000003856 thrombin receptor antagonist Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- C07D307/885—3,3-Diphenylphthalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
La presente se refiere a un proceso mejorado para preparar análogos de himbacina. Los compuestos son utiles como antagonistas de los receptores de trombina. El proceso mejorado puede permitir al menos una purificacion mediante cristalizacion, escalabilidad o rendimiento de proceso mejorado del enantiomero deseado más sencillo. También se describen intermediarios del proceso. Reivindicacion 1: Un proceso para preparar el compuesto de formula (1), donde R1 y R2 cada uno es independientemente seleccionado del grupo formado por alquilo, cicloalquilo, arilo y heteroarilo; y R8 se selecciona del grupo formado por halogeno, -CF3, alquilo C1-6, alcoxi C1-6, y -COOR9, donde R9 se selecciona del grupo formado por H, alquilo C1-6, fenilo y bencilo, comprendiendo dicho proceso: a) reducir un compuesto de formula (2), donde R2 es como se definio anteriormente, y R3 es H, alquilo, cicloalquilo, arilo, arilalquilo o heteroarilo; R4 y R5 cada uno se selecciona independientemente del grupo formado por H, alquilo, cicloalquilo, arilo, arilalquilo, y heteroarilo; o, R4 y R5, junto con el átomo de carbono al cual están unidos, forman un anillo de 5 a 7 miembros con entre 0-3 heteroátomos como miembros del anillo, para formar la formula (3), seguido por hidrolisis de formula (3) para dar un compuesto de formula (4), donde R2 es como se definio anteriormente; b) aminacion del compuesto de formula (4) para proporcionar el compuesto de formula (5), donde R2 es como se definio anteriormente, y R6 y R7 cada uno se selecciona independientemente del grupo formado por H, alquilo, cicloalquilo, arilo, y heteroarilo; c) convertir el compuesto de formula (5) en el compuesto (6); donde R1 y R2 son como se definieron anteriormente; d) convertir el compuesto de formula (6) en el compuesto de formula (7), donde R1 y R2 son como se definieron anteriormente; y e) convertir el compuesto de formula (7) en el compuesto de formula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64393205P | 2005-01-14 | 2005-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR052870A1 true AR052870A1 (es) | 2007-04-11 |
Family
ID=36228637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060100125A AR052870A1 (es) | 2005-01-14 | 2006-01-12 | Sintesis de analogos de himbacina |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1853592B1 (es) |
| JP (2) | JP4681617B2 (es) |
| CN (1) | CN101137647A (es) |
| AR (1) | AR052870A1 (es) |
| AT (1) | ATE500249T1 (es) |
| CA (1) | CA2594741A1 (es) |
| DE (1) | DE602006020414D1 (es) |
| ES (1) | ES2360721T3 (es) |
| MX (1) | MX2007008631A (es) |
| PT (1) | PT1853592E (es) |
| SG (1) | SG158885A1 (es) |
| WO (1) | WO2006076564A1 (es) |
| ZA (1) | ZA200705792B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE458726T1 (de) * | 2005-01-14 | 2010-03-15 | Schering Corp | Exo- und diastereoselektive synthese von himbacin-analoga |
| EP2558465B1 (de) | 2010-04-16 | 2014-12-17 | Sanofi | Trizyklische pyridyl-vinyl-pyrrole als par1-inhibitoren |
| PL2558462T3 (pl) | 2010-04-16 | 2015-03-31 | Sanofi Sa | Pirydylo-winylo-pirazolo-chinoliny jako inhibitory PAR1 |
| WO2015013083A1 (en) * | 2013-07-22 | 2015-01-29 | Merck Sharp & Dohme Corp. | Co-crystal of the par-1 receptor antagonist vorapaxar and aspirin |
| CN105330689B (zh) * | 2014-08-08 | 2018-08-17 | 博瑞生物医药（苏州）股份有限公司 | 制备Himbacine类似物中间体的制备方法 |
| CN105985303B (zh) * | 2015-02-13 | 2020-08-14 | 上海彩迩文生化科技有限公司 | 抗凝血剂的制备方法、中间体及其制备方法 |
| CN106478608A (zh) * | 2015-09-01 | 2017-03-08 | 博瑞生物医药（苏州）股份有限公司 | 沃拉帕沙的硫酸盐的结晶多晶型物 |
| CN105348241B (zh) * | 2015-12-11 | 2017-09-05 | 南京华威医药科技开发有限公司 | 一种硫酸沃拉帕沙中间体的合成方法 |
| ITUB20160876A1 (it) | 2016-02-19 | 2017-08-19 | Dambrosio Enzo Maria | Combinazione di un agente antiallergico con un antagonista muscarinico e/o un agonista dopaminergico per l'uso in prevenzione/ arresto di miopia assiale nell’uomo |
| CN107129477A (zh) * | 2016-02-26 | 2017-09-05 | 上海星泰医药科技有限公司 | ((1R,3aR,4aR,6R,8aR,9S,9aR)-9-甲酰基-1-甲基-3-氧杂十二氢萘[2,3-c]-6-呋喃基)羧酸乙酯的制备方法 |
| CN106749138B (zh) * | 2016-12-07 | 2019-08-16 | 扬子江药业集团四川海蓉药业有限公司 | 一种硫酸沃拉帕沙中间体醛的制备方法 |
| CN107955014B (zh) * | 2017-11-10 | 2019-06-28 | 南阳师范学院 | 萘并呋喃酮类化合物及制备与在制备抗肿瘤药物中的应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6063847A (en) * | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
| WO1999026943A1 (en) * | 1997-11-25 | 1999-06-03 | Schering Corporation | Thrombin receptor antagonists |
| US7235567B2 (en) * | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
| AR036832A1 (es) * | 2001-10-18 | 2004-10-06 | Schering Corp | Compuestos derivados de himbacina, agonistas receptores de trombina, composiciones farmaceuticas y el uso de dichos compuestos para la preparacion de medicamentos |
| PT1495018E (pt) * | 2002-04-16 | 2008-02-19 | Schering Corp | Antagonistas tricíclicos de receptores de trombina |
| ATE458726T1 (de) * | 2005-01-14 | 2010-03-15 | Schering Corp | Exo- und diastereoselektive synthese von himbacin-analoga |
-
2006
- 2006-01-12 AT AT06718299T patent/ATE500249T1/de active
- 2006-01-12 DE DE602006020414T patent/DE602006020414D1/de not_active Expired - Lifetime
- 2006-01-12 CA CA002594741A patent/CA2594741A1/en not_active Abandoned
- 2006-01-12 SG SG201000275-6A patent/SG158885A1/en unknown
- 2006-01-12 CN CNA2006800080207A patent/CN101137647A/zh active Pending
- 2006-01-12 AR ARP060100125A patent/AR052870A1/es not_active Application Discontinuation
- 2006-01-12 WO PCT/US2006/001208 patent/WO2006076564A1/en not_active Ceased
- 2006-01-12 ES ES06718299T patent/ES2360721T3/es not_active Expired - Lifetime
- 2006-01-12 JP JP2007551396A patent/JP4681617B2/ja not_active Expired - Fee Related
- 2006-01-12 MX MX2007008631A patent/MX2007008631A/es active IP Right Grant
- 2006-01-12 PT PT06718299T patent/PT1853592E/pt unknown
- 2006-01-12 EP EP06718299A patent/EP1853592B1/en not_active Expired - Lifetime
-
2007
- 2007-07-13 ZA ZA200705792A patent/ZA200705792B/xx unknown
-
2010
- 2010-12-09 JP JP2010275168A patent/JP2011046751A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008526981A (ja) | 2008-07-24 |
| WO2006076564A1 (en) | 2006-07-20 |
| SG158885A1 (en) | 2010-02-26 |
| ATE500249T1 (de) | 2011-03-15 |
| EP1853592A1 (en) | 2007-11-14 |
| CN101137647A (zh) | 2008-03-05 |
| DE602006020414D1 (en) | 2011-04-14 |
| ZA200705792B (en) | 2008-08-27 |
| PT1853592E (pt) | 2011-05-10 |
| EP1853592B1 (en) | 2011-03-02 |
| MX2007008631A (es) | 2007-09-12 |
| ES2360721T3 (es) | 2011-06-08 |
| JP2011046751A (ja) | 2011-03-10 |
| JP4681617B2 (ja) | 2011-05-11 |
| CA2594741A1 (en) | 2006-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |