CA2462030A1 - 3-`hydroxy-(-4-trifluoromethylphenyl)-methyl-7-spirocyclobutyl-5,6,7,8-tetrahydroquinolin-5-ol derivatives and the use of the same as cholesterol ester transfer protein (cetp) inhibitors - Google Patents
3-`hydroxy-(-4-trifluoromethylphenyl)-methyl-7-spirocyclobutyl-5,6,7,8-tetrahydroquinolin-5-ol derivatives and the use of the same as cholesterol ester transfer protein (cetp) inhibitors Download PDFInfo
- Publication number
- CA2462030A1 CA2462030A1 CA002462030A CA2462030A CA2462030A1 CA 2462030 A1 CA2462030 A1 CA 2462030A1 CA 002462030 A CA002462030 A CA 002462030A CA 2462030 A CA2462030 A CA 2462030A CA 2462030 A1 CA2462030 A1 CA 2462030A1
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- CA
- Canada
- Prior art keywords
- compounds
- mmol
- spirocyclobutyl
- formula
- hydroxy
- 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
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- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
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- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
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- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 108010037401 tendamistate Proteins 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000000929 thyromimetic effect Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10148436A DE10148436A1 (de) | 2001-10-01 | 2001-10-01 | Tetrahydrochinoline |
| DE10148436.4 | 2001-10-01 | ||
| PCT/EP2002/010444 WO2003028727A1 (de) | 2001-10-01 | 2002-09-18 | 3-`hydroxy- (-4-trifluoromethylphenyl) -methyl!-7-spirocyclobutyl-5,6,7,8- tetrahydrochinolin-5-ol-derivate und ihre verwendung als cholesterin-ester-transfer-protein (cetp) - inhibitoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2462030A1 true CA2462030A1 (en) | 2003-04-10 |
Family
ID=7701007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002462030A Abandoned CA2462030A1 (en) | 2001-10-01 | 2002-09-18 | 3-`hydroxy-(-4-trifluoromethylphenyl)-methyl-7-spirocyclobutyl-5,6,7,8-tetrahydroquinolin-5-ol derivatives and the use of the same as cholesterol ester transfer protein (cetp) inhibitors |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20050043341A1 (https=) |
| EP (1) | EP1434581A1 (https=) |
| JP (1) | JP2005508341A (https=) |
| AR (1) | AR036583A1 (https=) |
| CA (1) | CA2462030A1 (https=) |
| DE (1) | DE10148436A1 (https=) |
| DO (1) | DOP2002000457A (https=) |
| GT (1) | GT200200195A (https=) |
| HN (1) | HN2002000278A (https=) |
| PE (1) | PE20030604A1 (https=) |
| UY (1) | UY27458A1 (https=) |
| WO (1) | WO2003028727A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005315770B2 (en) * | 2004-12-18 | 2011-12-08 | Bayer Schering Pharma Aktiengesellschaft | 4-cycloalkyl-substituted tetrahydrochinoline derivatives and use thereof as medicaments |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06003357A (es) * | 2003-09-26 | 2006-06-08 | Japan Tobacco Inc | Metodo para inhibir la produccion de lipoproteina remanente. |
| DE602004023100D1 (de) | 2003-10-08 | 2009-10-22 | Lilly Co Eli | Verbindungen und verfahren zur behandlung von dyslipidemie |
| JP2007530550A (ja) | 2004-03-26 | 2007-11-01 | 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および方法 |
| BRPI0519566A2 (pt) * | 2004-12-18 | 2009-01-27 | Bayer Healthcare Ag | derivados de (5s)-3-[(s)-fléor(4-trifluormetilfenil)metil]-5,6,7,8-tet raidroquinolin-5-ol e seu uso como inibidores de cetp |
| DE102006012548A1 (de) | 2006-03-18 | 2007-09-20 | Bayer Healthcare Ag | Substituierte Chromanol-Derivate und ihre Verwendung |
| CN101096363B (zh) * | 2006-06-27 | 2011-05-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 2,4,5-三取代噻唑类化合物、其制备方法、药物组合物及其制药用途 |
| US20080145498A1 (en) * | 2006-12-14 | 2008-06-19 | Kraft Foods Holdings, Inc. | Texture and shape control process for acidified food products |
| BRPI0909105A2 (pt) * | 2008-03-05 | 2015-08-25 | Boehringer Ingelheim Int | Derivados de piridina tricíclicos, composição farmacêutica e uso dos mesmos, bem como processos para preparar os ditos compostos e a dita composição farmacêutica |
| UY33229A (es) * | 2010-02-19 | 2011-09-30 | Boehringer Ingelheim Int | Derivados de piridina tricíclicos, medicamentos que contienen tales compuestos, su uso y proceso pa ra su preparación |
| CA2804924C (en) | 2010-07-09 | 2016-06-28 | Daiichi Sankyo Company, Limited | Substituted pyridine compound |
| EP2760868B1 (en) | 2011-08-17 | 2018-04-25 | Boehringer Ingelheim International GmbH | Furo[3,4-c]quinoline derivatives, medicaments containing such compounds, their use and process for their preparation |
| TWI570118B (zh) | 2012-01-06 | 2017-02-11 | 第一三共股份有限公司 | 經取代之吡啶化合物的酸加成鹽 |
| JP6742316B2 (ja) | 2014-09-09 | 2020-08-19 | ベーリンガー インゲルハイム インターナショナル トレイディング （シャンハイ） カンパニー リミテッド | スピロ［２．５］オクタン−５，７−ジオンおよびスピロ［３．５］ノナン−６，８−ジオンの調製のための新規なプロセス |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP970330B1 (en) * | 1996-07-08 | 2004-06-30 | Bayer Ag | Cycloalkano pyridines |
| MA24643A1 (fr) * | 1997-09-18 | 1999-04-01 | Bayer Ag | Tetrahydro-naphtalenes substitues et composes analogues |
| DE19741051A1 (de) * | 1997-09-18 | 1999-03-25 | Bayer Ag | Hetero-Tetrahydrochinoline |
| DE19741399A1 (de) * | 1997-09-19 | 1999-03-25 | Bayer Ag | Tetrahydrochinoline |
-
2001
- 2001-10-01 DE DE10148436A patent/DE10148436A1/de not_active Withdrawn
-
2002
- 2002-09-02 DO DO2002000457A patent/DOP2002000457A/es unknown
- 2002-09-18 JP JP2003532059A patent/JP2005508341A/ja active Pending
- 2002-09-18 US US10/491,465 patent/US20050043341A1/en not_active Abandoned
- 2002-09-18 CA CA002462030A patent/CA2462030A1/en not_active Abandoned
- 2002-09-18 WO PCT/EP2002/010444 patent/WO2003028727A1/de not_active Ceased
- 2002-09-18 EP EP02772317A patent/EP1434581A1/de not_active Withdrawn
- 2002-09-25 AR ARP020103608A patent/AR036583A1/es unknown
- 2002-09-27 GT GT200200195A patent/GT200200195A/es unknown
- 2002-09-27 UY UY27458A patent/UY27458A1/es not_active Application Discontinuation
- 2002-09-30 PE PE2002000962A patent/PE20030604A1/es not_active Application Discontinuation
- 2002-10-01 HN HN2002000278A patent/HN2002000278A/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005315770B2 (en) * | 2004-12-18 | 2011-12-08 | Bayer Schering Pharma Aktiengesellschaft | 4-cycloalkyl-substituted tetrahydrochinoline derivatives and use thereof as medicaments |
Also Published As
| Publication number | Publication date |
|---|---|
| GT200200195A (es) | 2003-08-22 |
| US20050043341A1 (en) | 2005-02-24 |
| WO2003028727A9 (de) | 2003-11-13 |
| DE10148436A1 (de) | 2003-04-17 |
| JP2005508341A (ja) | 2005-03-31 |
| WO2003028727A1 (de) | 2003-04-10 |
| DOP2002000457A (es) | 2003-04-15 |
| UY27458A1 (es) | 2003-04-30 |
| PE20030604A1 (es) | 2003-09-07 |
| AR036583A1 (es) | 2004-09-15 |
| HN2002000278A (es) | 2002-12-20 |
| EP1434581A1 (de) | 2004-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |