TW200410942A - Pyrazole derivatives - Google Patents
Pyrazole derivatives Download PDFInfo
- Publication number
- TW200410942A TW200410942A TW092133632A TW92133632A TW200410942A TW 200410942 A TW200410942 A TW 200410942A TW 092133632 A TW092133632 A TW 092133632A TW 92133632 A TW92133632 A TW 92133632A TW 200410942 A TW200410942 A TW 200410942A
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- Prior art keywords
- low
- compound
- nmr
- esi
- amine
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- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 286
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 141
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 82
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 286
- -1 carbamoyloxy Chemical group 0.000 claims description 160
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 79
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 59
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical group 0.000 claims description 38
- 150000001412 amines Chemical class 0.000 claims description 29
- 239000004202 carbamide Substances 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 19
- 208000002193 Pain Diseases 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- 230000036407 pain Effects 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 206010061218 Inflammation Diseases 0.000 claims description 13
- 239000002253 acid Chemical group 0.000 claims description 13
- 230000004054 inflammatory process Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 12
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical group NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 6
- 230000005856 abnormality Effects 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 239000000730 antalgic agent Substances 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 5
- 229940035676 analgesics Drugs 0.000 claims description 5
- 230000002496 gastric effect Effects 0.000 claims description 5
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 238000001356 surgical procedure Methods 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 208000027932 Collagen disease Diseases 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000008035 Back Pain Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 3
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 3
- 208000008930 Low Back Pain Diseases 0.000 claims description 3
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 201000002661 Spondylitis Diseases 0.000 claims description 3
- 208000027418 Wounds and injury Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 230000000552 rheumatic effect Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000008961 swelling Effects 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 2
- 206010034464 Periarthritis Diseases 0.000 claims description 2
- 208000038016 acute inflammation Diseases 0.000 claims description 2
- 230000006022 acute inflammation Effects 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 208000037976 chronic inflammation Diseases 0.000 claims description 2
- 230000006020 chronic inflammation Effects 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000009534 blood test Methods 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 469
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 376
- 238000005160 1H NMR spectroscopy Methods 0.000 description 249
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 185
- 239000000843 powder Substances 0.000 description 183
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 172
- 229910001868 water Inorganic materials 0.000 description 168
- 235000019439 ethyl acetate Nutrition 0.000 description 148
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 144
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 143
- 238000003756 stirring Methods 0.000 description 139
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 137
- 239000000243 solution Substances 0.000 description 131
- 101150041968 CDC13 gene Proteins 0.000 description 117
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 117
- 239000003921 oil Substances 0.000 description 114
- 235000019198 oils Nutrition 0.000 description 114
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 106
- 239000012044 organic layer Substances 0.000 description 104
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 86
- 235000019341 magnesium sulphate Nutrition 0.000 description 86
- 238000005481 NMR spectroscopy Methods 0.000 description 85
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 80
- 238000002844 melting Methods 0.000 description 80
- 230000008018 melting Effects 0.000 description 80
- 239000011734 sodium Substances 0.000 description 74
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 238000010898 silica gel chromatography Methods 0.000 description 62
- 230000002829 reductive effect Effects 0.000 description 60
- 239000012267 brine Substances 0.000 description 58
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 57
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 56
- 239000010410 layer Substances 0.000 description 56
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 238000001816 cooling Methods 0.000 description 41
- 238000002360 preparation method Methods 0.000 description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 38
- 239000007787 solid Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 33
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 28
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000000706 filtrate Substances 0.000 description 26
- 238000001914 filtration Methods 0.000 description 24
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 230000002401 inhibitory effect Effects 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
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- 238000012360 testing method Methods 0.000 description 15
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- 238000004440 column chromatography Methods 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 238000012746 preparative thin layer chromatography Methods 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 7
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- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 5
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- 238000002425 crystallisation Methods 0.000 description 5
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
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- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 5
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 description 1
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Classifications
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- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
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- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/24—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms having sulfone or sulfonic acid radicals in the molecule
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/10—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 linked by a carbon chain containing aromatic 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2002953019A AU2002953019A0 (en) | 2002-12-02 | 2002-12-02 | Azole derivatives |
| AU2002953602A AU2002953602A0 (en) | 2002-12-30 | 2002-12-30 | New compounds |
| AU2003902015A AU2003902015A0 (en) | 2003-04-29 | 2003-04-29 | Azole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200410942A true TW200410942A (en) | 2004-07-01 |
Family
ID=32474716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092133632A TW200410942A (en) | 2002-12-02 | 2003-12-01 | Pyrazole derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7183306B2 (enExample) |
| EP (1) | EP1567503B1 (enExample) |
| JP (1) | JP4419078B2 (enExample) |
| KR (1) | KR20050083761A (enExample) |
| AR (1) | AR042273A1 (enExample) |
| AT (1) | ATE538097T1 (enExample) |
| BR (1) | BR0316332A (enExample) |
| CA (1) | CA2505945A1 (enExample) |
| ES (1) | ES2379076T3 (enExample) |
| MX (1) | MXPA05005742A (enExample) |
| NO (1) | NO20053215L (enExample) |
| NZ (1) | NZ540515A (enExample) |
| PL (1) | PL377778A1 (enExample) |
| TW (1) | TW200410942A (enExample) |
| WO (1) | WO2004050632A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002055502A1 (en) * | 2001-01-02 | 2002-07-18 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine derivatives useful as cyclooxygenase inhibitor |
| BR0316332A (pt) | 2002-12-02 | 2005-09-27 | Astellas Pharma Inc | Composto pirazólico, composição farmacêutica e agente analgésico contendo o mesmo, processo para sua preparação e seu uso e pacote comercial |
| RU2332412C2 (ru) | 2003-02-07 | 2008-08-27 | Дайити Фармасьютикал Ко., Лтд. | Производные пиразола |
| US20050075323A1 (en) * | 2003-03-05 | 2005-04-07 | Pfizer Inc | Beta3 adrenergic receptor agonists and uses thereof |
| US20060079566A1 (en) * | 2003-10-03 | 2006-04-13 | Ching-Shih Chen | PDK-1/Akt signaling inhibitors |
| EP1718617B1 (en) * | 2004-02-20 | 2009-08-19 | AstraZeneca AB | 3-substituted 1,5-diphenylpyrazole derivatives useful as cb1 modulators |
| AU2005258397A1 (en) * | 2004-07-01 | 2006-01-12 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole derivatives |
| MX2007001566A (es) * | 2004-08-06 | 2007-04-16 | Daiichi Seiyaku Co | Agente antiplaqueta y procedimiento para producir el mismo. |
| EP2368881A1 (en) * | 2005-01-10 | 2011-09-28 | University of Connecticut | Heteropyrazole analogs acting on cannabinoid receptors |
| FR2882365B1 (fr) * | 2005-02-21 | 2007-09-07 | Sanofi Aventis Sa | Derives de 2-(1,5-diphenyl-1h-pyrazol-3-yl)-1,3,4-oxadiazole leur preparation et leur application en therapeutique |
| GB0514739D0 (en) * | 2005-07-19 | 2005-08-24 | Astrazeneca Ab | Therapeutic agents |
| GB0516661D0 (en) * | 2005-08-13 | 2005-09-21 | Astrazeneca Ab | Therapeutic agents |
| CN101454299A (zh) | 2006-03-27 | 2009-06-10 | 东丽株式会社 | 酰脲衍生物及其医药用途 |
| US20100069443A1 (en) * | 2006-09-07 | 2010-03-18 | National University Corporation Okayama University | Compound with benzamide skeleton having cyclooxygenase-1 (cox-1)-selective inhibitory activity |
| AU2007336068B2 (en) * | 2006-12-18 | 2013-05-02 | 7Tm Pharma A/S | Modulators of CB1 receptors |
| GB0702862D0 (en) * | 2007-02-14 | 2007-03-28 | Univ Aberdeen | Therapeutic compounds |
| WO2008105383A1 (ja) * | 2007-02-26 | 2008-09-04 | Toray Industries, Inc. | ピラゾール誘導体およびその医薬用途 |
| JPWO2008114859A1 (ja) * | 2007-03-22 | 2010-07-08 | アステラス製薬株式会社 | ピラゾール誘導体を含有する医薬組成物 |
| US8039502B2 (en) * | 2007-07-24 | 2011-10-18 | The Ohio State University Research Foundation | Anti-infective agents against intracellular pathogens |
| JP5704925B2 (ja) | 2008-02-08 | 2015-04-22 | ウェルズ ファーゴ バンク ナショナル アソシエイション | オリゴマー−カンナビノイドコンジュゲート |
| DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
| AU2009263384A1 (en) | 2008-06-25 | 2009-12-30 | Daiichi Sankyo Company, Limited | Carboxylic acid compound |
| JP5654994B2 (ja) * | 2008-10-02 | 2015-01-14 | カンブレックス カルルスクーガ アクチ ボラケットＣａｍｂｒｅｘ Ｋａｒｌｓｋｏｇａ Ａｂ | ジケトン及び薬剤を製造するための新しいプロセス |
| TWI435874B (zh) * | 2008-10-31 | 2014-05-01 | Toray Industries | 環己烷衍生物及其醫藥用途 |
| DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
| DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
| US20120108823A1 (en) | 2009-04-22 | 2012-05-03 | The Ohio State University Research Foundation | Anti-francisella agents |
| DE102009036604A1 (de) | 2009-07-30 | 2011-02-03 | Aicuris Gmbh & Co. Kg | Substituierte Bis-Arylpyrazolamide mit terminaler primärer Amidfunktionalisierung und ihre Verwendung |
| DE102011055815A1 (de) | 2011-11-29 | 2013-05-29 | Aicuris Gmbh & Co. Kg | Carboxamid-substituierte Heteroaryl-Pyrazole und ihre Verwendung |
| DE102012016908A1 (de) | 2012-08-17 | 2014-02-20 | Aicuris Gmbh & Co. Kg | Tris-(Hetero)Aryl-Pyrazole und ihre Verwendung |
| JP6931695B2 (ja) | 2016-04-29 | 2021-09-08 | エフジーエイチ バイオテック，インコーポレーテッド | 疾患の治療のための二置換ピラゾール化合物 |
| CN109563048B (zh) | 2016-08-15 | 2022-05-06 | 拜耳农作物科学股份公司 | 用于制备3-氨基-1-(2,6-二取代的苯基)吡唑的方法 |
| JP7071981B2 (ja) * | 2016-09-07 | 2022-05-19 | エフジーエイチ バイオテック，インコーポレーテッド | 疾患の治療のための二置換ピラゾール化合物 |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN115611790A (zh) * | 2022-10-31 | 2023-01-17 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一种甲硫基甲基苯基醚的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826868A (en) * | 1986-05-29 | 1989-05-02 | Ortho Pharmaceutical Corporation | 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use |
| US5164381A (en) * | 1986-05-29 | 1992-11-17 | Ortho Pharmaceutical Corporation | Pharmacologically active 1,5-diaryl-3-substituted pyrazoles and method for synthesizing the same |
| US5051518A (en) * | 1987-05-29 | 1991-09-24 | Ortho Pharmaceutical Corporation | Pharmacologically active 2- and 3-substituted (1',5'-diaryl-3-pyrazolyl)-N-hydroxypropanamides |
| PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| US5550147A (en) * | 1992-02-05 | 1996-08-27 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazole derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
| US5298521A (en) * | 1993-08-30 | 1994-03-29 | Ortho Pharmaceutical Corporation | 1,5-diphenyl-3-pyrazolylalkyl-N-hydroxydithiocaramates, compositions and use |
| JPH10509140A (ja) | 1994-11-08 | 1998-09-08 | エーザイ株式会社 | ピラゾール誘導体 |
| ES2136018B1 (es) | 1997-06-17 | 2000-07-01 | Menarini Lab | Compuestos inhibidores selectivos de la ciclooxigenasa-i y su utilizacion como analgesicos, antiinflamatorios y antiartriticos. |
| US6506747B1 (en) * | 1998-06-05 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
| WO2000018741A2 (en) | 1998-09-30 | 2000-04-06 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazole compounds as cox-2 inhibitors |
| WO2000066562A1 (en) | 1999-05-03 | 2000-11-09 | Dr. Reddy's Research Foundation | Pyrazoles having antiinflammatory activity |
| DK1104759T3 (da) * | 1999-12-03 | 2004-01-26 | Pfizer Prod Inc | Heteroarylphenylpyrazolforbindelser som antiinflammatoriske/analgetiske midler |
| JP2003531201A (ja) | 2000-04-25 | 2003-10-21 | ファルマシア・コーポレーション | 炎症を治療するための２−フルオロベンゼンスルホニル化合物 |
| WO2002055502A1 (en) | 2001-01-02 | 2002-07-18 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine derivatives useful as cyclooxygenase inhibitor |
| AUPR878201A0 (en) | 2001-11-09 | 2001-12-06 | Fujisawa Pharmaceutical Co., Ltd. | New compounds |
| US20030162824A1 (en) * | 2001-11-12 | 2003-08-28 | Krul Elaine S. | Methods of treating or preventing a cardiovascular condition using a cyclooxygenase-1 inhibitor |
| CN100351237C (zh) * | 2002-04-05 | 2007-11-28 | 卡地拉健康护理有限公司 | 杂环化合物及其制备方法和含该化合物的药物组合物以及其在医药中的用途 |
| BR0316332A (pt) | 2002-12-02 | 2005-09-27 | Astellas Pharma Inc | Composto pirazólico, composição farmacêutica e agente analgésico contendo o mesmo, processo para sua preparação e seu uso e pacote comercial |
| CN100421632C (zh) | 2005-02-01 | 2008-10-01 | 金磊 | 人工心脏瓣膜成形环 |
-
2003
- 2003-11-14 BR BR0316332-6A patent/BR0316332A/pt not_active IP Right Cessation
- 2003-11-14 WO PCT/JP2003/014489 patent/WO2004050632A1/en not_active Ceased
- 2003-11-14 JP JP2004570721A patent/JP4419078B2/ja not_active Expired - Fee Related
- 2003-11-14 PL PL377778A patent/PL377778A1/pl unknown
- 2003-11-14 ES ES03812289T patent/ES2379076T3/es not_active Expired - Lifetime
- 2003-11-14 MX MXPA05005742A patent/MXPA05005742A/es active IP Right Grant
- 2003-11-14 KR KR1020057006436A patent/KR20050083761A/ko not_active Abandoned
- 2003-11-14 CA CA002505945A patent/CA2505945A1/en not_active Abandoned
- 2003-11-14 US US10/706,999 patent/US7183306B2/en not_active Expired - Fee Related
- 2003-11-14 EP EP03812289A patent/EP1567503B1/en not_active Expired - Lifetime
- 2003-11-14 AT AT03812289T patent/ATE538097T1/de active
- 2003-11-14 NZ NZ540515A patent/NZ540515A/en unknown
- 2003-12-01 TW TW092133632A patent/TW200410942A/zh unknown
- 2003-12-02 AR ARP030104441A patent/AR042273A1/es unknown
-
2005
- 2005-06-30 NO NO20053215A patent/NO20053215L/no not_active Application Discontinuation
-
2006
- 2006-12-13 US US11/610,230 patent/US20070112037A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AR042273A1 (es) | 2005-06-15 |
| ATE538097T1 (de) | 2012-01-15 |
| JP2006514095A (ja) | 2006-04-27 |
| US20040116475A1 (en) | 2004-06-17 |
| WO2004050632A1 (en) | 2004-06-17 |
| US20070112037A1 (en) | 2007-05-17 |
| PL377778A1 (pl) | 2006-02-20 |
| US7183306B2 (en) | 2007-02-27 |
| HK1087102A1 (zh) | 2006-10-06 |
| BR0316332A (pt) | 2005-09-27 |
| NO20053215D0 (no) | 2005-06-30 |
| KR20050083761A (ko) | 2005-08-26 |
| NZ540515A (en) | 2008-01-31 |
| NO20053215L (no) | 2005-09-01 |
| JP4419078B2 (ja) | 2010-02-24 |
| EP1567503A1 (en) | 2005-08-31 |
| CA2505945A1 (en) | 2004-06-17 |
| MXPA05005742A (es) | 2005-08-16 |
| EP1567503B1 (en) | 2011-12-21 |
| ES2379076T3 (es) | 2012-04-20 |
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