CA2392979A1 - Cristaux de 4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoleine - Google Patents
Cristaux de 4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoleine Download PDFInfo
- Publication number
- CA2392979A1 CA2392979A1 CA002392979A CA2392979A CA2392979A1 CA 2392979 A1 CA2392979 A1 CA 2392979A1 CA 002392979 A CA002392979 A CA 002392979A CA 2392979 A CA2392979 A CA 2392979A CA 2392979 A1 CA2392979 A1 CA 2392979A1
- Authority
- CA
- Canada
- Prior art keywords
- crystal
- trifluoromethyl
- formula
- rel
- dihydro
- 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.)
- Abandoned
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 100
- -1 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline Chemical class 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 78
- 241000124008 Mammalia Species 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims description 36
- 239000003937 drug carrier Substances 0.000 claims description 29
- 239000003085 diluting agent Substances 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 28
- 239000003981 vehicle Substances 0.000 claims description 26
- 201000001320 Atherosclerosis Diseases 0.000 claims description 21
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims description 18
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims description 18
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 17
- CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 claims description 17
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 12
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 11
- 208000008589 Obesity Diseases 0.000 claims description 11
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- 206010002383 Angina Pectoris Diseases 0.000 claims description 9
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- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 9
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- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims description 9
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- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
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- WGLUDAOFIMTWAM-WKOQGQMTSA-N ethanol;ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound CCO.COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WGLUDAOFIMTWAM-WKOQGQMTSA-N 0.000 claims description 5
- 238000009499 grossing Methods 0.000 claims description 4
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- 239000002243 precursor Substances 0.000 claims 3
- KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 2
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- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 abstract description 3
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 abstract description 3
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- 239000000243 solution Substances 0.000 description 17
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 239000000463 material Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
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- 239000003153 chemical reaction reagent Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
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- 239000011664 nicotinic acid Substances 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 4
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- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 3
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- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 3
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- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 3
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- AZFYCLSCZLWMBW-PWSUYJOCSA-N ethyl (2r,4s)-4-amino-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound FC(F)(F)C1=CC=C2N(C(=O)OCC)[C@H](CC)C[C@H](N)C2=C1 AZFYCLSCZLWMBW-PWSUYJOCSA-N 0.000 description 3
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- 239000012964 benzotriazole Substances 0.000 description 1
- YGBQZFPEMRCQRY-UHFFFAOYSA-N benzyl n-ethenylcarbamate Chemical compound C=CNC(=O)OCC1=CC=CC=C1 YGBQZFPEMRCQRY-UHFFFAOYSA-N 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 208000023589 ischemic disease Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16805199P | 1999-11-30 | 1999-11-30 | |
| US60/168,051 | 1999-11-30 | ||
| PCT/IB2000/001650 WO2001040190A1 (fr) | 1999-11-30 | 2000-11-14 | Cristaux de 4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoleine utilises en tant qu'inhibiteurs de cetp |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2392979A1 true CA2392979A1 (fr) | 2001-06-07 |
Family
ID=22609901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002392979A Abandoned CA2392979A1 (fr) | 1999-11-30 | 2000-11-14 | Cristaux de 4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoleine |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP1246804A1 (fr) |
| JP (1) | JP2003515592A (fr) |
| KR (1) | KR20020058057A (fr) |
| CN (1) | CN1402711A (fr) |
| AP (1) | AP2002002531A0 (fr) |
| AU (1) | AU1048801A (fr) |
| BG (1) | BG106854A (fr) |
| BR (1) | BR0015836A (fr) |
| CA (1) | CA2392979A1 (fr) |
| CO (1) | CO5271716A1 (fr) |
| EA (1) | EA200200510A1 (fr) |
| EC (1) | ECSP003792A (fr) |
| EE (1) | EE200200277A (fr) |
| GT (1) | GT200000199A (fr) |
| HU (1) | HUP0203521A2 (fr) |
| IL (1) | IL149097A0 (fr) |
| IS (1) | IS6338A (fr) |
| MA (1) | MA26845A1 (fr) |
| MX (1) | MXPA02005354A (fr) |
| NO (1) | NO20022558L (fr) |
| OA (1) | OA12099A (fr) |
| PA (1) | PA8506301A1 (fr) |
| PE (1) | PE20010904A1 (fr) |
| PL (1) | PL355892A1 (fr) |
| TN (1) | TNSN00231A1 (fr) |
| TR (1) | TR200201446T2 (fr) |
| UY (1) | UY26454A1 (fr) |
| WO (1) | WO2001040190A1 (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115279B2 (en) | 2000-08-03 | 2006-10-03 | Curatolo William J | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
| OA12619A (en) | 2001-06-21 | 2006-06-12 | Pfizer Prod Inc | Self-emulsifying formulations of cholesteryl estertransfer protein inhibitors. |
| GT200200170A (es) | 2001-09-28 | 2003-05-23 | Preparacion de inhibidor de cetp anhidro | |
| DE60320940D1 (de) | 2002-02-01 | 2008-06-26 | Pfizer Prod Inc | Pharmazeutische zusammensetzungen amorpher dispersionen von wirkstoffen und lipophiler mikrophasenbildender materialien |
| EP1920766B1 (fr) * | 2002-02-01 | 2017-08-23 | Bend Research, Inc | Compositions pharmaceutiques de dispersions amorphes de médicaments et matériaux formant des microphases lipophiles |
| WO2003063822A2 (fr) * | 2002-02-01 | 2003-08-07 | Pfizer Products Inc. | Procede de fabrication de dispersions medicamenteuses amorphes solides homogenes sechees par pulverisation au moyen d'un appareil de sechage par pulverisation modifie |
| BR0306208A (pt) | 2002-08-30 | 2004-10-13 | Japan Tobacco Inc | Compostos de dibenzilamina e seu uso farmacêutico |
| JP2006508077A (ja) | 2002-10-04 | 2006-03-09 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 炎症疾患を治療するためのｐｇｄ２レセプタアンタゴニスト |
| US7504508B2 (en) | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| US20040132771A1 (en) * | 2002-12-20 | 2004-07-08 | Pfizer Inc | Compositions of choleseteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors |
| CA2508840A1 (fr) | 2002-12-20 | 2004-07-08 | Pfizer Products Inc. | Formes posologiques comprenant un inhibiteur de cetp et un inhibiteur de hmg-coa reductase |
| MXPA05010456A (es) * | 2003-03-28 | 2006-03-21 | Pfizer Prod Inc | Compuestos de quinolina y quinoxalina. |
| BRPI0413277A (pt) | 2003-08-04 | 2006-10-10 | Pfizer Prod Inc | composições farmacêuticas de adsorvatos de medicamentos amorfos e materiais que formam microfases lipofìlicas |
| MXPA06003927A (es) | 2003-10-08 | 2008-02-07 | Lilly Co Eli | Compuestos y metodos para tratar dislipidemia. |
| JP4922924B2 (ja) * | 2004-04-13 | 2012-04-25 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｃｅｔｐ阻害薬 |
| JP2008504266A (ja) * | 2004-06-24 | 2008-02-14 | イーライ リリー アンド カンパニー | 異脂肪血症を治療するための化合物及び方法 |
| US20070149567A1 (en) * | 2004-09-23 | 2007-06-28 | Pfizer Inc | Quinoline compounds |
| WO2006033001A1 (fr) * | 2004-09-23 | 2006-03-30 | Pfizer Products Inc. | Composes de quinoline |
| CA2598133A1 (fr) | 2005-02-24 | 2006-08-31 | Millennium Pharmaceuticals, Inc. | Antagonistes de recepteur de pgd2 pour le traitement des maladies inflammatoires |
| WO2006098394A1 (fr) * | 2005-03-14 | 2006-09-21 | Japan Tobacco Inc. | Méthode pour inhiber l’absorption de lipides et l’inhibiteur de l'absorption de lipides |
| US7737155B2 (en) | 2005-05-17 | 2010-06-15 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
| EP2134169A2 (fr) | 2007-03-09 | 2009-12-23 | Indigene Pharmaceuticals Inc. | Combinaison de metformine r-(+) lipoate et d'agents antihyperlipidémiques pour le traitement de l'hyperglycémie diabétique et de complications diabétiques |
| US20110245209A1 (en) | 2008-12-16 | 2011-10-06 | Schering Corporation | Pyridopyrimidine derivatives and methods of use thereof |
| US20110243940A1 (en) | 2008-12-16 | 2011-10-06 | Schering Corporation | Bicyclic pyranone derivatives and methods of use thereof |
| AR077208A1 (es) | 2009-06-30 | 2011-08-10 | Lilly Co Eli | Derivados del acido trans-4-[[(5s)-5-[[[3,5-bis(trifluorometil) fenil] metil] (2-metil-2h-tetrazol-5-il) amino) -2,3,4,5-tetrahidro-7,9-dimetil-1h-1-benzazepin-1-il) metil)-ciclohexancarboxilico y sus formas cristalinas, composiciones farmaceuticas que los comprenden, su uso para preparar un medicam |
| CN106559998B (zh) | 2014-07-30 | 2022-01-25 | 豪夫迈·罗氏有限公司 | 预测对hdl升高剂或hdl模拟剂疗法的应答性的遗传标记 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231102A (en) * | 1989-03-08 | 1993-07-27 | Merck Sharp & Dohme, Ltd. | Tetrahydroquinoline derivatives useful for neurodegenerative disorders |
| AU5731098A (en) * | 1997-02-03 | 1998-08-25 | American Home Products Corporation | 2-substituted-1-acyl-1,2-dihydroquinoline derivatives to increase hdl-cholesterol level |
| US6197786B1 (en) * | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
-
2000
- 2000-11-09 CO CO00085285A patent/CO5271716A1/es unknown
- 2000-11-13 PA PA20008506301A patent/PA8506301A1/es unknown
- 2000-11-14 AU AU10488/01A patent/AU1048801A/en not_active Abandoned
- 2000-11-14 PL PL00355892A patent/PL355892A1/xx not_active Application Discontinuation
- 2000-11-14 TR TR2002/01446T patent/TR200201446T2/xx unknown
- 2000-11-14 KR KR1020027006914A patent/KR20020058057A/ko not_active Application Discontinuation
- 2000-11-14 EA EA200200510A patent/EA200200510A1/ru unknown
- 2000-11-14 IL IL14909700A patent/IL149097A0/xx unknown
- 2000-11-14 BR BR0015836-4A patent/BR0015836A/pt not_active IP Right Cessation
- 2000-11-14 HU HU0203521A patent/HUP0203521A2/hu unknown
- 2000-11-14 OA OA1200200158A patent/OA12099A/en unknown
- 2000-11-14 WO PCT/IB2000/001650 patent/WO2001040190A1/fr not_active Application Discontinuation
- 2000-11-14 EP EP00971662A patent/EP1246804A1/fr not_active Withdrawn
- 2000-11-14 AP APAP/P/2002/002531A patent/AP2002002531A0/en unknown
- 2000-11-14 CA CA002392979A patent/CA2392979A1/fr not_active Abandoned
- 2000-11-14 CN CN00816463A patent/CN1402711A/zh active Pending
- 2000-11-14 EE EEP200200277A patent/EE200200277A/xx unknown
- 2000-11-14 JP JP2001541875A patent/JP2003515592A/ja active Pending
- 2000-11-14 MX MXPA02005354A patent/MXPA02005354A/es unknown
- 2000-11-28 PE PE2000001267A patent/PE20010904A1/es not_active Application Discontinuation
- 2000-11-28 UY UY26454A patent/UY26454A1/es not_active Application Discontinuation
- 2000-11-29 GT GT200000199A patent/GT200000199A/es unknown
- 2000-11-29 EC EC2000003792A patent/ECSP003792A/es unknown
- 2000-11-29 TN TNTNSN00231A patent/TNSN00231A1/fr unknown
-
2002
- 2002-04-12 IS IS6338A patent/IS6338A/is unknown
- 2002-05-27 MA MA26653A patent/MA26845A1/fr unknown
- 2002-05-29 NO NO20022558A patent/NO20022558L/no not_active Application Discontinuation
- 2002-06-20 BG BG106854A patent/BG106854A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0015836A (pt) | 2002-08-06 |
| OA12099A (en) | 2006-05-04 |
| PE20010904A1 (es) | 2001-09-10 |
| TR200201446T2 (tr) | 2002-11-21 |
| IS6338A (is) | 2002-04-12 |
| BG106854A (bg) | 2002-12-29 |
| ECSP003792A (es) | 2002-04-23 |
| CN1402711A (zh) | 2003-03-12 |
| KR20020058057A (ko) | 2002-07-12 |
| IL149097A0 (en) | 2002-11-10 |
| GT200000199A (es) | 2002-05-23 |
| EP1246804A1 (fr) | 2002-10-09 |
| NO20022558D0 (no) | 2002-05-29 |
| MXPA02005354A (es) | 2002-12-11 |
| UY26454A1 (es) | 2001-07-31 |
| PA8506301A1 (es) | 2002-08-26 |
| CO5271716A1 (es) | 2003-04-30 |
| PL355892A1 (en) | 2004-05-31 |
| HUP0203521A2 (hu) | 2003-02-28 |
| MA26845A1 (fr) | 2004-12-20 |
| NO20022558L (no) | 2002-05-29 |
| WO2001040190A1 (fr) | 2001-06-07 |
| TNSN00231A1 (fr) | 2002-05-30 |
| JP2003515592A (ja) | 2003-05-07 |
| EE200200277A (et) | 2003-10-15 |
| AU1048801A (en) | 2001-06-12 |
| AP2002002531A0 (en) | 2002-06-30 |
| EA200200510A1 (ru) | 2002-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |