JP2007513167A5 - - Google Patents
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- JP2007513167A5 JP2007513167A5 JP2006542732A JP2006542732A JP2007513167A5 JP 2007513167 A5 JP2007513167 A5 JP 2007513167A5 JP 2006542732 A JP2006542732 A JP 2006542732A JP 2006542732 A JP2006542732 A JP 2006542732A JP 2007513167 A5 JP2007513167 A5 JP 2007513167A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- phenyl
- dimethyl
- triazole
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 60
- -1 C 3-7 cycloalkyl thiol Chemical class 0.000 claims 35
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 15
- 150000002825 nitriles Chemical class 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000002252 acyl group Chemical group 0.000 claims 7
- 125000004423 acyloxy group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 150000001356 alkyl thiols Chemical class 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims 3
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000004069 aziridinyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- DCVWMMMKFZVEDP-UHFFFAOYSA-N 1-(cyclobutylmethyl)triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1CCC1 DCVWMMMKFZVEDP-UHFFFAOYSA-N 0.000 claims 1
- LGQOKSIJJVBBHV-UHFFFAOYSA-N 1-[5-[(2-tert-butyl-5-methoxypyridin-4-yl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=CN=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 LGQOKSIJJVBBHV-UHFFFAOYSA-N 0.000 claims 1
- SAQCEFZARHJTAX-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-1-methyl-2-oxopyridin-3-yl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC=2C(N(C)C=C(C=2)C(C)(C)C)=O)C=C1N1C=C(C(=O)NCC(C)(C)C)N=N1 SAQCEFZARHJTAX-UHFFFAOYSA-N 0.000 claims 1
- RSGXQEULSRUZKZ-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methoxy-3-pyrazol-1-ylphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(N2N=CC=C2)C(OC)=C1NC(=O)C(C=1)=CC=C(C)C=1N1C=C(C(=O)NCC(C)(C)C)N=N1 RSGXQEULSRUZKZ-UHFFFAOYSA-N 0.000 claims 1
- NJGXUFWFJFNVGH-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methoxypyridin-3-yl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=NC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 NJGXUFWFJFNVGH-UHFFFAOYSA-N 0.000 claims 1
- KWGJEROCYOZDII-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methylsulfanylphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound CSC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 KWGJEROCYOZDII-UHFFFAOYSA-N 0.000 claims 1
- VGXCTICIHPEERI-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methylsulfinylphenyl)carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound CC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(C)(C)C)S(C)=O)C=C1N1C=C(C(O)=O)N=N1 VGXCTICIHPEERI-UHFFFAOYSA-N 0.000 claims 1
- GSIORXXIIZNKPV-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methylsulfonylphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(C)(C)C)S(C)(=O)=O)C=C1N1C=C(C(=O)NCC(C)(C)C)N=N1 GSIORXXIIZNKPV-UHFFFAOYSA-N 0.000 claims 1
- KSZQHAXTJBVLDC-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-oxo-1h-pyridin-3-yl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC=2C(NC=C(C=2)C(C)(C)C)=O)C=C1N1C=C(C(=O)NCC(C)(C)C)N=N1 KSZQHAXTJBVLDC-UHFFFAOYSA-N 0.000 claims 1
- FIOBBPFFZJWLOR-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-3-carbamoyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(C(N)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 FIOBBPFFZJWLOR-UHFFFAOYSA-N 0.000 claims 1
- SSPIKCBYPAGKRR-UHFFFAOYSA-N 1-[5-[[3-(3-amino-3-oxopropyl)-5-tert-butyl-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=C(CCC(N)=O)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 SSPIKCBYPAGKRR-UHFFFAOYSA-N 0.000 claims 1
- RFWSGHZBHQMAFJ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-1-(2-morpholin-4-ylethyl)-2-oxopyridin-3-yl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC=2C(N(CCN3CCOCC3)C=C(C=2)C(C)(C)C)=O)C=C1N1C=C(C(=O)NCC(C)(C)C)N=N1 RFWSGHZBHQMAFJ-UHFFFAOYSA-N 0.000 claims 1
- BQBKNNHIWVXRCR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-2-methoxy-3-(2-morpholin-4-ylethyl)phenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)C=2C=C(C(C)=CC=2)N2N=NC(=C2)C(=O)NCC(C)(C)C)C(OC)=C1CCN1CCOCC1 BQBKNNHIWVXRCR-UHFFFAOYSA-N 0.000 claims 1
- APSUEIQBCWILAY-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-2-methoxy-3-(methylsulfamoyl)phenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound CNS(=O)(=O)C1=CC(C(C)(C)C)=CC(NC(=O)C=2C=C(C(C)=CC=2)N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1OC APSUEIQBCWILAY-UHFFFAOYSA-N 0.000 claims 1
- PLCWFZCQQHKRFJ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-2-methoxy-3-(morpholin-4-ylmethyl)phenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)C=2C=C(C(C)=CC=2)N2N=NC(=C2)C(=O)NCC(C)(C)C)C(OC)=C1CN1CCOCC1 PLCWFZCQQHKRFJ-UHFFFAOYSA-N 0.000 claims 1
- YPYQOMZLHIRWHU-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-2-methoxy-3-[(4-methylpiperazin-1-yl)methyl]phenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)C=2C=C(C(C)=CC=2)N2N=NC(=C2)C(=O)NCC(C)(C)C)C(OC)=C1CN1CCN(C)CC1 YPYQOMZLHIRWHU-UHFFFAOYSA-N 0.000 claims 1
- QRBOAKDZMJWRCI-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(1,3-dioxolan-2-yl)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(C2OCCO2)C(OC)=C1NC(=O)C(C=1)=CC=C(C)C=1N1C=C(C(=O)NCC(C)(C)C)N=N1 QRBOAKDZMJWRCI-UHFFFAOYSA-N 0.000 claims 1
- DSKIJPKYGXAVQV-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-[(dimethylamino)methyl]-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=C(CN(C)C)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 DSKIJPKYGXAVQV-UHFFFAOYSA-N 0.000 claims 1
- XUEFLLSBLVSWRO-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-[2-(dimethylamino)ethylcarbamoyl]-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(C(=O)NCCN(C)C)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 XUEFLLSBLVSWRO-UHFFFAOYSA-N 0.000 claims 1
- RFOQIONLNJRSRK-SANMLTNESA-N 1-[5-[[5-tert-butyl-3-[[(3s)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NC(=O)C=2C=C(C(C)=CC=2)N2N=NC(=C2)C(=O)NCC(C)(C)C)C(OC)=C1CN1CC[C@H](N(C)C)C1 RFOQIONLNJRSRK-SANMLTNESA-N 0.000 claims 1
- GALUQOJIYNVKSF-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-[[2-(dimethylamino)ethyl-methylamino]methyl]-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=C(CN(C)CCN(C)C)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 GALUQOJIYNVKSF-UHFFFAOYSA-N 0.000 claims 1
- SCNFJVBHQUHEIL-RUZDIDTESA-N 1-[5-[[5-tert-butyl-3-[[2-(dimethylamino)ethyl-methylamino]methyl]-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound COC1=C(CN(C)CCN(C)C)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 SCNFJVBHQUHEIL-RUZDIDTESA-N 0.000 claims 1
- GSSXLFACIJSBOM-UHFFFAOYSA-N 2h-pyran-2-ol Chemical compound OC1OC=CC=C1 GSSXLFACIJSBOM-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 208000004232 Enteritis Diseases 0.000 claims 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 206010048873 Traumatic arthritis Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 208000019664 bone resorption disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 238000007887 coronary angioplasty Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000004276 dioxalanyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 210000003714 granulocyte Anatomy 0.000 claims 1
- 238000001631 haemodialysis Methods 0.000 claims 1
- 230000000322 hemodialysis Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 230000001338 necrotic effect Effects 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000008816 organ damage Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 1
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000002537 thrombolytic effect Effects 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims 1
- 0 C*c(cc(*)cc1N2)c1OC(*)C2=O Chemical compound C*c(cc(*)cc1N2)c1OC(*)C2=O 0.000 description 14
- MTPGADABNGLNIY-UHFFFAOYSA-N CC(C)(C)c(cc1C)cc(-[n]2cncc2)c1OC Chemical compound CC(C)(C)c(cc1C)cc(-[n]2cncc2)c1OC MTPGADABNGLNIY-UHFFFAOYSA-N 0.000 description 1
- WELWBSZBTIZLJR-UHFFFAOYSA-N CC(C)(C)c(cc1C)cc(OC(O)=O)c1OC Chemical compound CC(C)(C)c(cc1C)cc(OC(O)=O)c1OC WELWBSZBTIZLJR-UHFFFAOYSA-N 0.000 description 1
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| US60/526,569 | 2003-12-03 | ||
| PCT/US2004/040306 WO2005056535A1 (en) | 2003-12-03 | 2004-12-01 | 1,2,3-triazole amide derivatives as inhibitors of cytokine production |
Publications (3)
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| JP2007513167A JP2007513167A (ja) | 2007-05-24 |
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| EP (1) | EP1692116B1 (https=) |
| JP (1) | JP4824576B2 (https=) |
| AT (1) | ATE501128T1 (https=) |
| CA (1) | CA2547410C (https=) |
| DE (1) | DE602004031759D1 (https=) |
| ES (1) | ES2360292T3 (https=) |
| WO (1) | WO2005056535A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE329909T1 (de) * | 2002-11-27 | 2006-07-15 | Boehringer Ingelheim Pharma | 1,2,3-triazolamid-derivate als cytokininhibitoren |
| US7485657B2 (en) * | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| US7531560B2 (en) * | 2004-11-10 | 2009-05-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| EP1867331A4 (en) * | 2005-04-06 | 2009-04-08 | Takeda Pharmaceutical | TRIAZOLE DERIVATIVE AND USE THEREOF |
| CN101228137B (zh) * | 2005-07-25 | 2010-09-29 | 弗·哈夫曼-拉罗切有限公司 | 被取代的三唑衍生物和它们作为神经激肽3受体拮抗剂的用途 |
| CN101501023A (zh) * | 2006-07-07 | 2009-08-05 | 贝林格尔.英格海姆国际有限公司 | 苯基取代的杂芳基衍生物及其作为抗肿瘤剂的用途 |
| CA2692379A1 (en) * | 2007-07-02 | 2009-01-08 | Boehringer Ingelheim International Gmbh | Antiproliferative compounds based on 5-membered heterocycles |
| CL2008001943A1 (es) * | 2007-07-02 | 2009-09-11 | Boehringer Ingelheim Int | Compuestos derivados de fenil-triazol, inhibidores de enzimas de señales especificas que participan del control de la proliferacion celular; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar cancer, infecciones, enfermedades inflamatorias y autoinmunes. |
| TW201014860A (en) | 2008-09-08 | 2010-04-16 | Boehringer Ingelheim Int | New chemical compounds |
| US8778929B2 (en) | 2008-09-29 | 2014-07-15 | Boehringer Ingelheim International Gmbh | Substituted heteroaryl inhibitors of B-RAF |
| EP2398797B1 (en) | 2009-02-17 | 2013-11-06 | Boehringer Ingelheim International GmbH | Pyrimido[5,4-d]pyrimidine derivatives for the inhibition of tyrosine kinases |
| WO2011117381A1 (en) | 2010-03-26 | 2011-09-29 | Boehringer Ingelheim International Gmbh | B-raf kinase inhibitors |
| WO2011117382A1 (en) | 2010-03-26 | 2011-09-29 | Boehringer Ingelheim International Gmbh | Pyridyltriazoles |
| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| US8889684B2 (en) | 2011-02-02 | 2014-11-18 | Boehringer Ingelheim International Gmbh | Azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| CN108715585A (zh) | 2018-04-23 | 2018-10-30 | 中国药科大学 | 苯基联三氮唑类mll1-wdr5蛋白-蛋白相互作用抑制剂 |
| JP2024016314A (ja) * | 2020-12-24 | 2024-02-07 | 小野薬品工業株式会社 | 一般式（ｉ－ａ）で示される化合物、その薬学的に許容される塩、またはそれらの水和物と免疫チェックポイント阻害薬および／またはｅｐ４受容体拮抗薬との組み合わせ |
| CN115403533B (zh) * | 2021-05-28 | 2023-08-25 | 永康市第一人民医院 | 一种1-苯乙烯基-1,2,3-三氮唑化合物及其制备方法和应用 |
| EP4493182A1 (en) * | 2022-03-14 | 2025-01-22 | Huyabio International, LLC | Phenyl triazole mll1-wdr5 protein-protein interaction inhibitor |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0051084A1 (en) | 1980-11-04 | 1982-05-12 | American Cyanamid Company | Substituted 1H-1,2,4-triazoles |
| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| FR2732967B1 (fr) | 1995-04-11 | 1997-07-04 | Sanofi Sa | 1-phenylpyrazole-3-carboxamides substitues, actifs sur la neurotensine, leur preparation, les compositions pharmaceutiques en contenant |
| RU2214398C2 (ru) | 1998-03-09 | 2003-10-20 | Такеда Кемикал Индастриз, Лтд. | Производное циклоалкена, способ его получения (варианты), фармацевтическая композиция, способ ингибирования, способ профилактики или лечения |
| WO1999051580A1 (en) | 1998-04-08 | 1999-10-14 | Abbott Laboratories | Pyrazole inhibitors of cytokine production |
| ATE254105T1 (de) | 1998-09-25 | 2003-11-15 | Astrazeneca Ab | Benzamid-derivate und ihre verwendung als cytokine inhibitoren |
| PT1123287E (pt) | 1998-10-23 | 2003-12-31 | Dow Agrosciences Llc | 1-(piridil substituido)-1,2,4-triazoles insecticidas |
| MY133845A (en) | 2000-03-10 | 2007-11-30 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| US6451820B1 (en) | 2000-03-23 | 2002-09-17 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenly)triazoles and their use as anti-inflammatory agents |
| US6498423B1 (en) | 2001-06-27 | 2002-12-24 | Welch Allyn, Inc. | Lamp thermal control by directed air flow |
| WO2003022820A1 (en) | 2001-09-06 | 2003-03-20 | Bristol-Myers Squibb Pharma Company. | Heteroaromatic substituted cyclopropane as corticotropin releasing hormone |
| US7132438B2 (en) | 2001-10-09 | 2006-11-07 | Amgen Inc. | Benzimidazole derivatives |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| ATE329909T1 (de) * | 2002-11-27 | 2006-07-15 | Boehringer Ingelheim Pharma | 1,2,3-triazolamid-derivate als cytokininhibitoren |
| EP2385041B1 (en) | 2003-05-01 | 2013-09-18 | Bristol-Myers Squibb Company | Pyrazole-amine compounds useful as kinase inhibitors |
-
2004
- 2004-12-01 AT AT04812750T patent/ATE501128T1/de active
- 2004-12-01 WO PCT/US2004/040306 patent/WO2005056535A1/en not_active Ceased
- 2004-12-01 US US11/002,022 patent/US7511042B2/en active Active
- 2004-12-01 DE DE602004031759T patent/DE602004031759D1/de not_active Expired - Lifetime
- 2004-12-01 CA CA2547410A patent/CA2547410C/en not_active Expired - Lifetime
- 2004-12-01 JP JP2006542732A patent/JP4824576B2/ja not_active Expired - Lifetime
- 2004-12-01 ES ES04812750T patent/ES2360292T3/es not_active Expired - Lifetime
- 2004-12-01 EP EP04812750A patent/EP1692116B1/en not_active Expired - Lifetime
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