JP2002514640A - p38キナーゼ阻害剤としての1,5−ジアリール置換ピラゾール類 - Google Patents
p38キナーゼ阻害剤としての1,5−ジアリール置換ピラゾール類Info
- Publication number
- JP2002514640A JP2002514640A JP2000548327A JP2000548327A JP2002514640A JP 2002514640 A JP2002514640 A JP 2002514640A JP 2000548327 A JP2000548327 A JP 2000548327A JP 2000548327 A JP2000548327 A JP 2000548327A JP 2002514640 A JP2002514640 A JP 2002514640A
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbyl
- hydride
- aryl
- compound
- group
- 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.)
- Withdrawn
Links
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title claims abstract description 55
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 title claims abstract description 55
- 150000003217 pyrazoles Chemical class 0.000 title description 17
- 229940043355 kinase inhibitor Drugs 0.000 title description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 202
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 38
- 230000000694 effects Effects 0.000 claims abstract description 24
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 247
- 150000004678 hydrides Chemical group 0.000 claims description 152
- 125000003118 aryl group Chemical group 0.000 claims description 142
- -1 hydroxy, mercapto, hydroxycarbonyl Chemical group 0.000 claims description 142
- 125000001424 substituent group Chemical group 0.000 claims description 131
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000001769 aryl amino group Chemical group 0.000 claims description 15
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 15
- 125000005110 aryl thio group Chemical group 0.000 claims description 15
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 15
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 15
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 15
- 125000004476 heterocycloamino group Chemical group 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- 125000004470 heterocyclooxy group Chemical group 0.000 claims description 13
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 12
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 7
- 150000001540 azides Chemical class 0.000 claims description 7
- 230000001575 pathological effect Effects 0.000 claims description 7
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 241001024304 Mino Species 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000003106 haloaryl group Chemical group 0.000 claims description 5
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000002944 cyanoaryl group Chemical group 0.000 claims description 3
- 125000003375 sulfoxide group Chemical group 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 4
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims 3
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 2
- 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 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 102100040247 Tumor necrosis factor Human genes 0.000 abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 22
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 abstract description 21
- 201000010099 disease Diseases 0.000 abstract description 17
- 230000001404 mediated effect Effects 0.000 abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 228
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 100
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
- 235000019439 ethyl acetate Nutrition 0.000 description 79
- 239000000243 solution Substances 0.000 description 69
- 239000000203 mixture Substances 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 238000002360 preparation method Methods 0.000 description 60
- 125000000217 alkyl group Chemical group 0.000 description 51
- 235000002639 sodium chloride Nutrition 0.000 description 51
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 50
- 235000019341 magnesium sulphate Nutrition 0.000 description 50
- 239000012267 brine Substances 0.000 description 49
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 49
- 238000000921 elemental analysis Methods 0.000 description 48
- 239000000047 product Substances 0.000 description 48
- 239000012044 organic layer Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
- 239000003921 oil Substances 0.000 description 40
- 235000019198 oils Nutrition 0.000 description 40
- 239000007787 solid Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 239000000706 filtrate Substances 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
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- 210000004027 cell Anatomy 0.000 description 29
- 238000010992 reflux Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
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- 229910002027 silica gel Inorganic materials 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 235000019441 ethanol Nutrition 0.000 description 22
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 150000002576 ketones Chemical class 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- 102000000589 Interleukin-1 Human genes 0.000 description 16
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003556 assay Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
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- 230000002829 reductive effect Effects 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 11
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- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
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- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
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- Dermatology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
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- Gastroenterology & Hepatology (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8549498P | 1998-05-14 | 1998-05-14 | |
US60/085,494 | 1998-05-14 | ||
PCT/US1999/007036 WO1999058523A1 (en) | 1998-05-14 | 1999-05-12 | 1,5-DIARYL SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2002514640A true JP2002514640A (ja) | 2002-05-21 |
Family
ID=22191985
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000548327A Withdrawn JP2002514640A (ja) | 1998-05-14 | 1999-05-12 | p38キナーゼ阻害剤としての1,5−ジアリール置換ピラゾール類 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1077971A1 (de) |
JP (1) | JP2002514640A (de) |
AU (1) | AU3859999A (de) |
CA (1) | CA2331878A1 (de) |
WO (1) | WO1999058523A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017503024A (ja) * | 2014-01-06 | 2017-01-26 | アルゴメディクス インコーポレイテッド | Trpa1モジュレーター |
Families Citing this family (48)
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US6979686B1 (en) | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
CA2294057A1 (en) * | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
US7301021B2 (en) | 1997-07-02 | 2007-11-27 | Smithkline Beecham Corporation | Substituted imidazole compounds |
AU765492B2 (en) * | 1998-12-25 | 2003-09-18 | Teikoku Hormone Mfg. Co., Ltd. | Aminopyrazole derivatives |
AU766079B2 (en) * | 1999-06-03 | 2003-10-09 | Teikoku Hormone Mfg. Co., Ltd. | Substituted pyrazole compounds |
US7122666B2 (en) | 1999-07-21 | 2006-10-17 | Sankyo Company, Limited | Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses |
US7053099B1 (en) | 1999-11-23 | 2006-05-30 | Smithkline Beecham Corporation | 3,4-dihydro-(1H)quinazolin-2-one compounds as CSBP/p38 kinase inhibitors |
US6569885B1 (en) | 1999-12-23 | 2003-05-27 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
US6403629B2 (en) * | 2000-05-02 | 2002-06-11 | J.B. Chemical And Pharmaceuticals Limited | Heterocyclic compounds for therapeutic use |
PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
JP2004515550A (ja) | 2000-12-15 | 2004-05-27 | グラクソ グループ リミテッド | 治療用化合物 |
US6919352B2 (en) | 2000-12-15 | 2005-07-19 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyridine and pyrimidine therapeutic compounds |
GB0102687D0 (en) * | 2001-02-02 | 2001-03-21 | Pharmacia & Upjohn Spa | Oxazolyl-pyrazole derivatives active as kinase inhibitors,process for their preparation and pharmaceutical compositions comprising them |
MY130778A (en) * | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
AU2002248531A1 (en) | 2001-03-08 | 2002-09-24 | Smithkline Beecham Corporation | Pyrazolopyriadine derivatives |
GB2373245A (en) * | 2001-03-12 | 2002-09-18 | Bayer Ag | Pyridinyl pyrazoles and their use for the treatment of COPD |
EP1372643A1 (de) | 2001-03-30 | 2004-01-02 | Smithkline Beecham Corporation | Pyrazolopyridine, verfahren zu ihrer herstellung und verwendung als therapeutika |
ATE332301T1 (de) | 2001-04-10 | 2006-07-15 | Smithkline Beecham Corp | Antivirale pyrazolopyridin verbindungen |
ES2242028T3 (es) | 2001-04-27 | 2005-11-01 | Smithkline Beecham Corporation | Derivados de pirazolo(1,5-a)piridina. |
US6878729B2 (en) | 2001-05-04 | 2005-04-12 | The Procter & Gamble Company | Medicinal uses of dihydropyrazoles |
CN1518550A (zh) | 2001-06-21 | 2004-08-04 | ʷ��˿�������ȳ�ķ����˾ | 用于预防和治疗疱疹病毒感染的咪唑并[1,2-a]吡啶衍生物 |
CN1281603C (zh) * | 2001-08-30 | 2006-10-25 | 霍夫曼-拉罗奇有限公司 | 作为抗炎药的氨基吡咯化合物 |
US7057049B2 (en) | 2001-09-25 | 2006-06-06 | Pharmacia Corporation | Process for making substituted pyrazoles |
CN1321644C (zh) | 2001-09-25 | 2007-06-20 | 法玛西雅公司 | 制备取代的吡唑的方法 |
EP1432712B1 (de) | 2001-10-05 | 2006-05-17 | SmithKline Beecham Corporation | Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion |
GB0124938D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0127929D0 (en) * | 2001-11-21 | 2002-01-16 | Celltech R&D Ltd | Chemical compounds |
AU2002357740A1 (en) | 2001-12-11 | 2003-06-23 | Smithkline Beecham Corporation | Pyrazolo-pyridine derivatives as antiherpes agents |
AU2002353147A1 (en) * | 2001-12-13 | 2003-06-30 | Abbott Laboratories | 3-(phenyl-alkoxy)-5-(phenyl)-pyridine derivatives and related compounds as kinase inhibitors for the treatment of cancer |
US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
EP1707205A2 (de) | 2002-07-09 | 2006-10-04 | Boehringer Ingelheim Pharma GmbH & Co. KG | Pharazeutische zusammensetzungen aus anticholinergica und p38 kinase hemmern zur behandlung von erkrankungen der atemwege |
ATE323702T1 (de) | 2002-08-06 | 2006-05-15 | Astrazeneca Ab | Kondensierte pyridine und pyrimidine mit tie2 (tek) aktivität |
WO2004033454A1 (en) | 2002-10-03 | 2004-04-22 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridine derivatives |
WO2004060346A2 (en) | 2002-12-30 | 2004-07-22 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
AU2004209495A1 (en) | 2003-02-07 | 2004-08-19 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole derivative |
ES2386784T3 (es) | 2003-05-01 | 2012-08-30 | Bristol-Myers Squibb Company | Compuestos de pirazol-amina útiles como inhibidores de quinasas |
GB0402518D0 (en) | 2004-02-05 | 2004-03-10 | Astrazeneca Ab | Therapeutic agents |
US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
GB0417910D0 (en) * | 2004-08-11 | 2004-09-15 | Novartis Ag | Organic compounds |
NZ552868A (en) | 2004-08-12 | 2009-07-31 | Pfizer | Triazolopyridinylsulfanyl derivatives as P38 MAP kinase inhibitors |
PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
EP1992344A1 (de) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 Alpha als therapeutisches Target für Erkrankungen, die mit einer FGFR3- Mutation assoziiert sind |
WO2012170931A2 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
SG11201811655SA (en) * | 2016-07-06 | 2019-01-30 | Algomedix Inc | Trpa1 antagonists for treatment of dry eye, ocular pain and inflammation |
US20230303562A1 (en) * | 2020-09-28 | 2023-09-28 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | Pyrazole compound and preparation method therefor and use thereof |
CA3209491A1 (en) | 2021-03-15 | 2022-09-22 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory disease |
CN114773262B (zh) * | 2022-05-19 | 2024-05-07 | 兄弟科技股份有限公司 | 2-氰基-4-吡啶羧酸甲酯的合成方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2833779A (en) * | 1956-10-29 | 1958-05-06 | American Cyanamid Co | Substituted pyrazoles |
US5434178A (en) * | 1993-11-30 | 1995-07-18 | G.D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
CA2294057A1 (en) * | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
-
1999
- 1999-05-12 EP EP99921363A patent/EP1077971A1/de not_active Withdrawn
- 1999-05-12 WO PCT/US1999/007036 patent/WO1999058523A1/en active Application Filing
- 1999-05-12 AU AU38599/99A patent/AU3859999A/en not_active Abandoned
- 1999-05-12 JP JP2000548327A patent/JP2002514640A/ja not_active Withdrawn
- 1999-05-12 CA CA002331878A patent/CA2331878A1/en not_active Abandoned
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017503024A (ja) * | 2014-01-06 | 2017-01-26 | アルゴメディクス インコーポレイテッド | Trpa1モジュレーター |
US10428049B2 (en) | 2014-01-06 | 2019-10-01 | Algomedix, Inc. | TRPA1 modulators |
Also Published As
Publication number | Publication date |
---|---|
WO1999058523A1 (en) | 1999-11-18 |
EP1077971A1 (de) | 2001-02-28 |
CA2331878A1 (en) | 1999-11-18 |
AU3859999A (en) | 1999-11-29 |
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