ES2254109T3 - Procedimiento para la preparacion del ester etilico del acido (-)-(2r,4s)-4-(3,5-bis-trifluorometilbencilamino)-2-etil-6-trifluorometil-3,4-dihidro-2h-quinolina-1-carboxilo. - Google Patents
Procedimiento para la preparacion del ester etilico del acido (-)-(2r,4s)-4-(3,5-bis-trifluorometilbencilamino)-2-etil-6-trifluorometil-3,4-dihidro-2h-quinolina-1-carboxilo.Info
- Publication number
- ES2254109T3 ES2254109T3 ES00310064T ES00310064T ES2254109T3 ES 2254109 T3 ES2254109 T3 ES 2254109T3 ES 00310064 T ES00310064 T ES 00310064T ES 00310064 T ES00310064 T ES 00310064T ES 2254109 T3 ES2254109 T3 ES 2254109T3
- Authority
- ES
- Spain
- Prior art keywords
- acid
- ethyl
- trifluoromethyl
- dihydro
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims abstract description 104
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 15
- -1 3, 5- bis-trifluoromethylbenzylamino Chemical group 0.000 claims abstract description 35
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims abstract description 7
- 125000004494 ethyl ester group Chemical group 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000725 suspension Substances 0.000 claims description 20
- JRBOFAXVGHMLMM-APWZRJJASA-N (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound COC(=O)N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(O)=O)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JRBOFAXVGHMLMM-APWZRJJASA-N 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- QOTDBJKZKHHPCY-UHFFFAOYSA-N 4-amino-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound FC(F)(F)C1=CC=C2N(C(O)=O)C(CC)CC(N)C2=C1 QOTDBJKZKHHPCY-UHFFFAOYSA-N 0.000 claims description 9
- VYLKEIFSWPITNN-WBVHZDCISA-N (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound N([C@H]1C[C@H](N(C2=CC=C(C=C21)C(F)(F)F)C(O)=O)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VYLKEIFSWPITNN-WBVHZDCISA-N 0.000 claims description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 8
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- 150000004682 monohydrates Chemical class 0.000 claims description 7
- HVOAACKKZXUIKP-UHFFFAOYSA-N n-[1-(benzotriazol-1-yl)propyl]-4-(trifluoromethyl)aniline Chemical compound N1=NC2=CC=CC=C2N1C(CC)NC1=CC=C(C(F)(F)F)C=C1 HVOAACKKZXUIKP-UHFFFAOYSA-N 0.000 claims description 7
- LDWLIXZSDPXYDR-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC(C=O)=CC(C(F)(F)F)=C1 LDWLIXZSDPXYDR-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 6
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- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- FOTRUJUPLHRVNU-QNBGGDODSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid;hydrate Chemical class O.C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 FOTRUJUPLHRVNU-QNBGGDODSA-N 0.000 claims description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
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- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16796799P | 1999-11-30 | 1999-11-30 | |
| US167967P | 1999-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2254109T3 true ES2254109T3 (es) | 2006-06-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00310064T Expired - Lifetime ES2254109T3 (es) | 1999-11-30 | 2000-11-13 | Procedimiento para la preparacion del ester etilico del acido (-)-(2r,4s)-4-(3,5-bis-trifluorometilbencilamino)-2-etil-6-trifluorometil-3,4-dihidro-2h-quinolina-1-carboxilo. |
Country Status (44)
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| HN2000000203A (es) * | 1999-11-30 | 2001-06-13 | Pfizer Prod Inc | Procedimiento para la obtencion de 1,2,3,4-tetrahidroquinolinas 4-carboxiamino-2- sustituidas. |
| WO2003053359A2 (en) | 2001-12-19 | 2003-07-03 | Atherogenics, Inc. | 1,3-bis-(substituted-phenyl)-2-propyn-1-ones and their use to treat disorders |
| HUP0500165A2 (en) * | 2001-12-19 | 2006-09-28 | Atherogenics Inc | Chalcone derivatives and their use to treat diseases |
| AU2003230916A1 (en) * | 2002-04-11 | 2003-10-27 | Roar Holding Llc | Ex vivo method for determination of cetp activity and efficacy of heart disease treatment |
| US20090181966A1 (en) * | 2002-10-04 | 2009-07-16 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| US7504508B2 (en) * | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| CN100363348C (zh) * | 2002-10-04 | 2008-01-23 | 千禧药品公司 | 治疗炎性疾病的前列腺素d2受体拮抗剂 |
| US7223870B2 (en) * | 2002-11-01 | 2007-05-29 | Pfizer Inc. | Methods for preparing N-arylated oxazolidinones via a copper catalyzed cross coupling reaction |
| WO2004056727A2 (en) * | 2002-12-19 | 2004-07-08 | Atherogenics, Inc. | Process of making chalcone derivatives |
| US20040132771A1 (en) * | 2002-12-20 | 2004-07-08 | Pfizer Inc | Compositions of choleseteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors |
| EP1961419B1 (en) | 2002-12-20 | 2010-03-24 | Pfizer Products Inc. | Dosage forms comprising a CETP inhibitor and an HMG-CoA reductase inhibitor |
| US20060100239A1 (en) * | 2003-03-04 | 2006-05-11 | Izuru Nagasaki | Method for producing optically active amines |
| KR20080008440A (ko) * | 2003-03-17 | 2008-01-23 | 니뽄 다바코 산교 가부시키가이샤 | Ｃｅｔｐ 억제제의 약제학적 조성물 |
| KR20050110017A (ko) * | 2003-03-17 | 2005-11-22 | 니뽄 다바코 산교 가부시키가이샤 | Ｓ-'２-(''１-(２-에틸부틸)시클로헥실!카르보닐!아미노)페닐!-２-메틸프로판티오에이트의 경구 생체이용율을증가시키는 방법 |
| TWI494102B (zh) * | 2003-05-02 | 2015-08-01 | Japan Tobacco Inc | 包含ｓ-〔２（〔〔１-（２-乙基丁基）環己基〕羰基〕胺基）苯基〕２-甲基丙烷硫酯及ｈｍｇ輔酶ａ還原酶抑制劑之組合 |
| PT1670768E (pt) * | 2003-10-08 | 2009-11-20 | Lilly Co Eli | Compostos e métodos para tratamento de dislipidemia |
| UA90269C2 (ru) * | 2004-04-02 | 2010-04-26 | Мицубиси Танабе Фарма Корпорейшн | Тетрагидрохинолиновые производные и способ их получения |
| EP1761521A1 (en) * | 2004-06-24 | 2007-03-14 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| DOP2005000123A (es) | 2004-07-02 | 2011-07-15 | Merck Sharp & Dohme | Inhibidores de cetp |
| WO2006033001A1 (en) * | 2004-09-23 | 2006-03-30 | Pfizer Products Inc. | Quinoline compounds |
| WO2006069162A1 (en) * | 2004-12-20 | 2006-06-29 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds and their pharmaceutical compositions |
| GT200600093A (es) * | 2005-02-24 | 2006-10-19 | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias | |
| UY30244A1 (es) | 2006-03-30 | 2007-11-30 | Tanabe Seiyaku Co | Un proceso para preparar derivados de tetrahidroquinolina |
| WO2008112166A2 (en) | 2007-03-09 | 2008-09-18 | Indigene Pharmaceuticals Inc. | Combination of metformin r-(+) lipoate and antihyperlipidemic agents for the treatment of diabetic hyperglycemia and diabetic complications |
| CN101429160B (zh) * | 2007-11-06 | 2011-10-19 | 上海药明康德新药开发有限公司 | 一种1-r-4-氨基-1,2,3,4-四氢喹啉的合成方法 |
| TWI450896B (zh) | 2009-06-30 | 2014-09-01 | Lilly Co Eli | 反式－４－〔〔（５ｓ）－５－〔〔〔３，５－雙（三氟甲基）苯基〕甲基〕（２－甲基－２ｈ－四唑－５－基）胺基〕－２，３，４，５－四氫－７，９－二甲基－１ｈ－１－苯并氮呯－１－基〕甲基〕－環己基羧酸 |
| IL317973A (en) | 2022-07-05 | 2025-02-01 | Newamsterdam Pharma B V | Salts of ovicetrapib and processes for their production and intermediates |
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| FR7870M (forum.php) * | 1968-11-08 | 1970-04-27 | ||
| US3971789A (en) | 1972-10-21 | 1976-07-27 | John Wyeth & Brother Limited | O-(4-Quinolylamino)benzamides |
| GB8432091D0 (en) | 1984-12-19 | 1985-01-30 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
| US4839368A (en) | 1986-05-02 | 1989-06-13 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives |
| GB8804444D0 (en) | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| US5231102A (en) | 1989-03-08 | 1993-07-27 | Merck Sharp & Dohme, Ltd. | Tetrahydroquinoline derivatives useful for neurodegenerative disorders |
| PT100905A (pt) * | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| US6197786B1 (en) | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
| US6140342A (en) | 1998-09-17 | 2000-10-31 | Pfizer Inc. | Oxy substituted 4-carboxyamino-2-methyl-1,2,3,4-tetrahydroquinolines |
| US6147089A (en) | 1998-09-17 | 2000-11-14 | Pfizer Inc. | Annulated 4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines |
| HN2000000203A (es) * | 1999-11-30 | 2001-06-13 | Pfizer Prod Inc | Procedimiento para la obtencion de 1,2,3,4-tetrahidroquinolinas 4-carboxiamino-2- sustituidas. |
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- 2000-09-27 PA PA20008503801A patent/PA8503801A1/es unknown
- 2000-09-29 OA OA1200000268A patent/OA11494A/en unknown
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- 2000-11-03 GT GT200000190A patent/GT200000190A/es unknown
- 2000-11-09 CO CO00085289A patent/CO5261552A1/es not_active Application Discontinuation
- 2000-11-13 AT AT00310064T patent/ATE315028T1/de not_active IP Right Cessation
- 2000-11-13 DE DE60025317T patent/DE60025317T2/de not_active Expired - Fee Related
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- 2000-11-22 HR HR20000804A patent/HRP20000804A2/hr not_active Application Discontinuation
- 2000-11-23 AU AU71789/00A patent/AU784694B2/en not_active Ceased
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- 2000-11-27 ZA ZA200006947A patent/ZA200006947B/xx unknown
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- 2000-11-28 SG SG200006869A patent/SG102603A1/en unknown
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- 2000-11-28 CA CA002327029A patent/CA2327029C/en not_active Expired - Fee Related
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2006
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