CA2559917A1 - Compounds as ccri antagonists - Google Patents
Compounds as ccri antagonists Download PDFInfo
- Publication number
- CA2559917A1 CA2559917A1 CA002559917A CA2559917A CA2559917A1 CA 2559917 A1 CA2559917 A1 CA 2559917A1 CA 002559917 A CA002559917 A CA 002559917A CA 2559917 A CA2559917 A CA 2559917A CA 2559917 A1 CA2559917 A1 CA 2559917A1
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- phenyl
- compound
- oxo
- mmol
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 372
- 239000005557 antagonist Substances 0.000 title abstract description 4
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- -1 nitro, oxy Chemical group 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- PSDYQSWHANEKRV-UHFFFAOYSA-N [S]N Chemical compound [S]N PSDYQSWHANEKRV-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 7
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 7
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 282
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- 238000000746 purification Methods 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 27
- 239000012047 saturated solution Substances 0.000 description 25
- QIHACWKSBIJGCC-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(F)=CC=C1CN1CC(N2)COCC2C1 QIHACWKSBIJGCC-UHFFFAOYSA-N 0.000 description 20
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 13
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0409236.7A GB0409236D0 (en) | 2004-04-26 | 2004-04-26 | Organic compounds |
| GB0409236.7 | 2004-04-26 | ||
| PCT/EP2005/004422 WO2005103054A2 (en) | 2004-04-26 | 2005-04-25 | Bridged piperazine and piperidine derivatives as ccri antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2559917A1 true CA2559917A1 (en) | 2005-11-03 |
Family
ID=32344398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002559917A Abandoned CA2559917A1 (en) | 2004-04-26 | 2005-04-25 | Compounds as ccri antagonists |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20070196270A1 (https=) |
| EP (1) | EP1794164A2 (https=) |
| JP (1) | JP2007534678A (https=) |
| KR (2) | KR100845356B1 (https=) |
| CN (1) | CN101238131A (https=) |
| AR (1) | AR052397A1 (https=) |
| AU (1) | AU2005235724B2 (https=) |
| BR (1) | BRPI0510313A (https=) |
| CA (1) | CA2559917A1 (https=) |
| GB (1) | GB0409236D0 (https=) |
| MX (1) | MXPA06012380A (https=) |
| RU (1) | RU2383548C2 (https=) |
| TW (1) | TW200603805A (https=) |
| WO (1) | WO2005103054A2 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2712211T3 (es) | 2013-06-20 | 2019-05-09 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas |
| MX368059B (es) | 2013-07-18 | 2019-09-18 | Novartis Ag | Inhibidores de autotaxina que comprenden un núcleo de anillo heteroaromático de bencil-amida cíclica. |
| CN115286637B (zh) * | 2022-08-11 | 2024-03-22 | 成都金博汇康医药科技有限公司 | 三氮杂桥环化合物及其中间体化合物、制备方法和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6207665B1 (en) * | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
| US6818643B1 (en) * | 1999-12-08 | 2004-11-16 | Bristol-Myers Squibb Company | Neurotrophic bicyclic diamides |
| AU2001292160A1 (en) * | 2000-10-19 | 2002-04-29 | Pfizer Products Inc. | Bridged piperazine derivatives |
| UY27003A1 (es) * | 2000-11-06 | 2002-07-31 | Schering Ag | Productos radiofarmacéuticos para el diagnóstico de la enfermedad de alzheimer |
| JPWO2002100833A1 (ja) * | 2001-06-12 | 2004-09-24 | 住友製薬株式会社 | Ｒｈｏキナーゼ阻害剤 |
| AP2005003196A0 (en) * | 2002-07-18 | 2005-03-31 | Pfizer Prod Inc | Bicyclic piperidine derivatives as antagonists of the CCR1 chemokine receptor. |
| GB0224917D0 (en) * | 2002-10-25 | 2002-12-04 | Novartis Ag | Organic compounds |
-
2004
- 2004-04-26 GB GBGB0409236.7A patent/GB0409236D0/en not_active Ceased
-
2005
- 2005-04-25 CA CA002559917A patent/CA2559917A1/en not_active Abandoned
- 2005-04-25 WO PCT/EP2005/004422 patent/WO2005103054A2/en not_active Ceased
- 2005-04-25 CN CNA2005800132391A patent/CN101238131A/zh active Pending
- 2005-04-25 JP JP2007508868A patent/JP2007534678A/ja not_active Ceased
- 2005-04-25 KR KR1020067022181A patent/KR100845356B1/ko not_active Expired - Fee Related
- 2005-04-25 BR BRPI0510313-4A patent/BRPI0510313A/pt not_active IP Right Cessation
- 2005-04-25 EP EP05737794A patent/EP1794164A2/en not_active Withdrawn
- 2005-04-25 RU RU2006141702/04A patent/RU2383548C2/ru not_active IP Right Cessation
- 2005-04-25 AU AU2005235724A patent/AU2005235724B2/en not_active Ceased
- 2005-04-25 MX MXPA06012380A patent/MXPA06012380A/es not_active Application Discontinuation
- 2005-04-25 US US10/599,819 patent/US20070196270A1/en not_active Abandoned
- 2005-04-25 KR KR1020087002184A patent/KR20080015151A/ko not_active Ceased
- 2005-04-25 AR ARP050101623A patent/AR052397A1/es unknown
- 2005-04-25 TW TW094113108A patent/TW200603805A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080015151A (ko) | 2008-02-18 |
| US20070196270A1 (en) | 2007-08-23 |
| GB0409236D0 (en) | 2004-05-26 |
| CN101238131A (zh) | 2008-08-06 |
| KR20070014154A (ko) | 2007-01-31 |
| MXPA06012380A (es) | 2007-01-17 |
| WO2005103054A2 (en) | 2005-11-03 |
| RU2383548C2 (ru) | 2010-03-10 |
| EP1794164A2 (en) | 2007-06-13 |
| AR052397A1 (es) | 2007-03-21 |
| AU2005235724A1 (en) | 2005-11-03 |
| BRPI0510313A (pt) | 2007-10-16 |
| AU2005235724B2 (en) | 2008-10-30 |
| JP2007534678A (ja) | 2007-11-29 |
| RU2006141702A (ru) | 2008-06-10 |
| WO2005103054A3 (en) | 2007-02-08 |
| KR100845356B1 (ko) | 2008-07-09 |
| TW200603805A (en) | 2006-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |