CA2308428A1 - Aromatic heterocyclic compounds as anti-inflammatory agents - Google Patents
Aromatic heterocyclic compounds as anti-inflammatory agents Download PDFInfo
- Publication number
- CA2308428A1 CA2308428A1 CA002308428A CA2308428A CA2308428A1 CA 2308428 A1 CA2308428 A1 CA 2308428A1 CA 002308428 A CA002308428 A CA 002308428A CA 2308428 A CA2308428 A CA 2308428A CA 2308428 A1 CA2308428 A1 CA 2308428A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- heteroaryl
- group
- phenyl
- fully halogenated
- 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
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 title abstract description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
- 239000002260 anti-inflammatory agent Substances 0.000 title description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 201000010099 disease Diseases 0.000 claims abstract description 30
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- 230000004054 inflammatory process Effects 0.000 claims abstract description 11
- 206010061218 Inflammation Diseases 0.000 claims abstract description 10
- 230000001575 pathological effect Effects 0.000 claims abstract description 7
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 6
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 5
- -1 cyclopentanyl Chemical group 0.000 claims description 310
- 125000000217 alkyl group Chemical group 0.000 claims description 261
- 125000001072 heteroaryl group Chemical group 0.000 claims description 228
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 148
- 125000001624 naphthyl group Chemical group 0.000 claims description 116
- 125000003342 alkenyl group Chemical group 0.000 claims description 92
- 125000004076 pyridyl group Chemical group 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 49
- 125000003282 alkyl amino group Chemical group 0.000 claims description 48
- 125000001544 thienyl group Chemical group 0.000 claims description 48
- 125000001475 halogen functional group Chemical group 0.000 claims description 40
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- 125000003118 aryl group Chemical group 0.000 claims description 32
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 29
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- 238000006243 chemical reaction Methods 0.000 claims description 17
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 16
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- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 10
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6410297P | 1997-11-03 | 1997-11-03 | |
| US60/064,102 | 1997-11-03 | ||
| PCT/US1998/022907 WO1999023091A1 (en) | 1997-11-03 | 1998-10-29 | Aromatic heterocyclic compounds as anti-inflammatory agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2308428A1 true CA2308428A1 (en) | 1999-05-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002308428A Abandoned CA2308428A1 (en) | 1997-11-03 | 1998-10-29 | Aromatic heterocyclic compounds as anti-inflammatory agents |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US6080763A (enExample) |
| EP (1) | EP1028953A1 (enExample) |
| JP (1) | JP2001521934A (enExample) |
| AU (1) | AU1367599A (enExample) |
| CA (1) | CA2308428A1 (enExample) |
| WO (1) | WO1999023091A1 (enExample) |
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| US20070244120A1 (en) * | 2000-08-18 | 2007-10-18 | Jacques Dumas | Inhibition of raf kinase using substituted heterocyclic ureas |
| US20080300281A1 (en) * | 1997-12-22 | 2008-12-04 | Jacques Dumas | Inhibition of p38 Kinase Activity Using Aryl and Heteroaryl Substituted Heterocyclic Ureas |
| US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| DK1043995T3 (da) * | 1997-12-22 | 2007-03-05 | Bayer Pharmaceuticals Corp | Inhibering af p38 kinaseaktivitet ved anvendelse af aryl- og heteroaryl-substituerede, heterocykliske urinstoffer |
| ES2155045T3 (es) * | 1997-12-22 | 2007-02-01 | Bayer Pharmaceuticals Corp. | Inhibicion de la quinasa raf utilizando ureas heterociclicas sustituidas con arilo y heteroarilo. |
| MXPA00006233A (es) * | 1997-12-22 | 2002-09-18 | Bayer Ag | Inhibicion de la actividad de la cinasa p38 utilizando ureas heterociclicas sustituidas. |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| AU3387999A (en) * | 1998-04-08 | 1999-10-25 | Abbott Laboratories | Pyrazole inhibitors of cytokine production |
| US20080269265A1 (en) * | 1998-12-22 | 2008-10-30 | Scott Miller | Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas |
| US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
| EP1140840B1 (en) | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7351834B1 (en) | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| EP1158985B1 (en) | 1999-01-13 | 2011-12-28 | Bayer HealthCare LLC | OMEGA-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| HUP0202248A3 (en) * | 1999-03-12 | 2006-06-28 | Boehringer Ingelheim Pharma | Compounds useful as anti-inflammatory agents |
| EP1690854A1 (en) * | 1999-03-12 | 2006-08-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic urea and related compounds useful as anti-inflammatory agents |
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- 1998-10-29 EP EP98957405A patent/EP1028953A1/en not_active Withdrawn
- 1998-10-29 WO PCT/US1998/022907 patent/WO1999023091A1/en not_active Ceased
- 1998-10-29 JP JP2000518962A patent/JP2001521934A/ja active Pending
- 1998-10-29 US US09/181,743 patent/US6080763A/en not_active Expired - Lifetime
- 1998-10-29 AU AU13675/99A patent/AU1367599A/en not_active Abandoned
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1999
- 1999-12-14 US US09/461,446 patent/US6228881B1/en not_active Expired - Lifetime
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2001
- 2001-03-14 US US09/808,084 patent/US6432995B2/en not_active Expired - Lifetime
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| EP1028953A1 (en) | 2000-08-23 |
| JP2001521934A (ja) | 2001-11-13 |
| AU1367599A (en) | 1999-05-24 |
| US6228881B1 (en) | 2001-05-08 |
| WO1999023091A1 (en) | 1999-05-14 |
| US20010039290A1 (en) | 2001-11-08 |
| US6080763A (en) | 2000-06-27 |
| US6432995B2 (en) | 2002-08-13 |
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