ES2265596T3 - Derivados de 1,2,3-triazol-amida como inhibidores de citocinas. - Google Patents
Derivados de 1,2,3-triazol-amida como inhibidores de citocinas. Download PDFInfo
- Publication number
- ES2265596T3 ES2265596T3 ES03789871T ES03789871T ES2265596T3 ES 2265596 T3 ES2265596 T3 ES 2265596T3 ES 03789871 T ES03789871 T ES 03789871T ES 03789871 T ES03789871 T ES 03789871T ES 2265596 T3 ES2265596 T3 ES 2265596T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- methyl
- tert
- butyl
- methanesulfonylamino
- 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.)
- Expired - Lifetime
Links
- 239000003112 inhibitor Substances 0.000 title description 9
- 239000002253 acid Substances 0.000 claims abstract description 156
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- -1 carbocycle Chemical group 0.000 claims abstract description 102
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 55
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002252 acyl group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 13
- 150000007513 acids Chemical class 0.000 claims abstract description 10
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 10
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 61
- 201000010099 disease Diseases 0.000 claims description 51
- XOZZYNPAVVPHRQ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(O)=O)=C1 XOZZYNPAVVPHRQ-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 230000002757 inflammatory effect Effects 0.000 claims description 12
- 208000014674 injury Diseases 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000001154 acute effect Effects 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 230000006378 damage Effects 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 230000001575 pathological effect Effects 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001540 azides Chemical class 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
- ZNBCIZKROAZBJE-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(O)=O)=C1 ZNBCIZKROAZBJE-UHFFFAOYSA-N 0.000 claims description 7
- VLHZHHLVRNKJKP-UHFFFAOYSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(O)=O)N=N2)N)=C1 VLHZHHLVRNKJKP-UHFFFAOYSA-N 0.000 claims description 7
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 7
- 208000027418 Wounds and injury Diseases 0.000 claims description 7
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 7
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 7
- 230000003902 lesion Effects 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000006386 Bone Resorption Diseases 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004069 aziridinyl group Chemical group 0.000 claims description 5
- 230000024279 bone resorption Effects 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 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 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims description 5
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- VGOUIDIUWDZAMQ-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(O)=O)=C1 VGOUIDIUWDZAMQ-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 201000009906 Meningitis Diseases 0.000 claims description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
- 239000003146 anticoagulant agent Substances 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
- AEPUKVYYZXYIJW-UHFFFAOYSA-N 1-[3-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]phenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=CC(N2N=NC(=C2)C(O)=O)=C1 AEPUKVYYZXYIJW-UHFFFAOYSA-N 0.000 claims description 3
- CKRXHRLGSWZPKI-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2,3-dimethylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC(C)=C(C)C(N2N=NC(=C2)C(O)=O)=C1 CKRXHRLGSWZPKI-UHFFFAOYSA-N 0.000 claims description 3
- SROJYDDZHUJIEF-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-3-fluoro-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC(F)=C(C)C(N2N=NC(=C2)C(O)=O)=C1 SROJYDDZHUJIEF-UHFFFAOYSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 206010048768 Dermatosis Diseases 0.000 claims description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 3
- 206010018366 Glomerulonephritis acute Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004276 dioxalanyl group Chemical group 0.000 claims description 3
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- 125000002541 furyl group Chemical group 0.000 claims description 3
- 210000003714 granulocyte Anatomy 0.000 claims description 3
- 238000001631 haemodialysis Methods 0.000 claims description 3
- 230000000322 hemodialysis Effects 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 3
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 3
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 230000002537 thrombolytic effect Effects 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- FAPKMWWBUNYNKN-UHFFFAOYSA-N 1-[5-[[3-(methanesulfonamido)-2-methoxy-5-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(F)(F)F)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(O)=O)=C1 FAPKMWWBUNYNKN-UHFFFAOYSA-N 0.000 claims description 2
- SOBXUYMZUBUAOG-UHFFFAOYSA-N 4-morpholin-4-ylsulfonylmorpholine Chemical compound C1COCCN1S(=O)(=O)N1CCOCC1 SOBXUYMZUBUAOG-UHFFFAOYSA-N 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
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- 239000003054 catalyst Substances 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- TYEWNBMWTXMGOC-UHFFFAOYSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-4-methyl-3-[4-(morpholine-4-carbonyl)triazol-1-yl]benzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N2CCOCC2)=C1 TYEWNBMWTXMGOC-UHFFFAOYSA-N 0.000 claims description 2
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- RCSSHZGQHHEHPZ-MRVPVSSYSA-N (1r)-n-methyl-1-phenylethanamine Chemical compound CN[C@H](C)C1=CC=CC=C1 RCSSHZGQHHEHPZ-MRVPVSSYSA-N 0.000 claims 3
- TWMNPSJTUSFPEC-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 TWMNPSJTUSFPEC-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- MYKHBWFULXPPPE-UHFFFAOYSA-N 1-[5-[(3-amino-5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=C(N)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 MYKHBWFULXPPPE-UHFFFAOYSA-N 0.000 claims 1
- FFDIGMODELFUPV-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2-morpholin-4-ylethyl)triazole-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCOCC2)=C1 FFDIGMODELFUPV-UHFFFAOYSA-N 0.000 claims 1
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- BSCPSIHMYYIRHZ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-fluorophenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(F)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 BSCPSIHMYYIRHZ-UHFFFAOYSA-N 0.000 claims 1
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
-
- 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
- A61P9/04—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
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43051902P | 2002-11-27 | 2002-11-27 | |
| US430519P | 2002-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2265596T3 true ES2265596T3 (es) | 2007-02-16 |
Family
ID=32469486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03789871T Expired - Lifetime ES2265596T3 (es) | 2002-11-27 | 2003-11-20 | Derivados de 1,2,3-triazol-amida como inhibidores de citocinas. |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7166628B2 (enExample) |
| EP (1) | EP1567507B1 (enExample) |
| JP (1) | JP4926402B2 (enExample) |
| AT (1) | ATE329909T1 (enExample) |
| AU (1) | AU2003294388A1 (enExample) |
| CA (1) | CA2507184C (enExample) |
| DE (1) | DE60306193T2 (enExample) |
| ES (1) | ES2265596T3 (enExample) |
| WO (1) | WO2004050642A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7591994B2 (en) * | 2002-12-13 | 2009-09-22 | Immunomedics, Inc. | Camptothecin-binding moiety conjugates |
| US7511042B2 (en) | 2003-12-03 | 2009-03-31 | Boehringer Ingelheim Pharmaceuticals, Inc. | Triazole compounds |
| US7485657B2 (en) | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| WO2006109846A1 (ja) * | 2005-04-06 | 2006-10-19 | Takeda Pharmaceutical Company Limited | トリアゾール誘導体およびその用途 |
| WO2006124283A1 (en) * | 2005-05-12 | 2006-11-23 | Boehringer Ingelheim International, Gmbh | Bis-amination of aryl halides |
| ES2353724T3 (es) * | 2005-07-25 | 2011-03-04 | F. Hoffmann-La Roche Ag | Derivados de triazol substitutidos y su uso como antagonistas del receptor neuroquinina 3. |
| PE20080401A1 (es) * | 2006-07-07 | 2008-06-23 | Boehringer Ingelheim Int | DERIVADOS DE HETEROARIL-FENIL SUSTITUIDOS COMO INHIBIDORES DE B-Raf-QUINASAS |
| 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. |
| CA2692379A1 (en) * | 2007-07-02 | 2009-01-08 | Boehringer Ingelheim International Gmbh | Antiproliferative compounds based on 5-membered heterocycles |
| TW201014860A (en) | 2008-09-08 | 2010-04-16 | Boehringer Ingelheim Int | New chemical compounds |
| EP2350052B1 (en) | 2008-09-29 | 2014-08-13 | Boehringer Ingelheim International GmbH | Antiproliferative compounds |
| EP2398797B1 (en) | 2009-02-17 | 2013-11-06 | Boehringer Ingelheim International GmbH | Pyrimido[5,4-d]pyrimidine derivatives for the inhibition of tyrosine kinases |
| JP2011057661A (ja) * | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| EP2552907B1 (en) | 2010-03-26 | 2014-10-22 | Boehringer Ingelheim International GmbH | Pyridyltriazoles |
| US9290507B2 (en) | 2010-03-26 | 2016-03-22 | Boehringer Ingelheim International Gmbh | B-RAF kinase inhibitors |
| 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 |
| EP2925746A1 (en) * | 2012-12-03 | 2015-10-07 | F. Hoffmann-La Roche AG | Substituted triazole and imidazole compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| US20010044445A1 (en) * | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| US7297708B2 (en) | 2001-09-06 | 2007-11-20 | Bristol-Myers Squibb Company | Heteroaromatic substituted cyclopropane as corticotropin releasing hormone ligands |
| CA2462289C (en) | 2001-10-04 | 2010-02-23 | Nicholas D. Cosford | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| EP1434579B1 (en) | 2001-10-09 | 2011-06-08 | Amgen Inc. | Imidazole derivatives as antiinflammatory agents |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| US7511042B2 (en) * | 2003-12-03 | 2009-03-31 | Boehringer Ingelheim Pharmaceuticals, Inc. | Triazole compounds |
| US7485657B2 (en) * | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
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2003
- 2003-11-20 AT AT03789871T patent/ATE329909T1/de active
- 2003-11-20 EP EP03789871A patent/EP1567507B1/en not_active Expired - Lifetime
- 2003-11-20 JP JP2004557232A patent/JP4926402B2/ja not_active Expired - Lifetime
- 2003-11-20 WO PCT/US2003/037104 patent/WO2004050642A1/en not_active Ceased
- 2003-11-20 DE DE60306193T patent/DE60306193T2/de not_active Expired - Lifetime
- 2003-11-20 ES ES03789871T patent/ES2265596T3/es not_active Expired - Lifetime
- 2003-11-20 CA CA2507184A patent/CA2507184C/en not_active Expired - Lifetime
- 2003-11-20 US US10/718,380 patent/US7166628B2/en not_active Expired - Lifetime
- 2003-11-20 AU AU2003294388A patent/AU2003294388A1/en not_active Abandoned
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2006
- 2006-09-07 US US11/470,849 patent/US7569568B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2507184A1 (en) | 2004-06-17 |
| DE60306193D1 (de) | 2006-07-27 |
| EP1567507A1 (en) | 2005-08-31 |
| JP2006514940A (ja) | 2006-05-18 |
| WO2004050642A1 (en) | 2004-06-17 |
| CA2507184C (en) | 2012-01-10 |
| US7569568B2 (en) | 2009-08-04 |
| US20040102492A1 (en) | 2004-05-27 |
| ATE329909T1 (de) | 2006-07-15 |
| US20070032492A1 (en) | 2007-02-08 |
| DE60306193T2 (de) | 2006-10-12 |
| AU2003294388A1 (en) | 2004-06-23 |
| JP4926402B2 (ja) | 2012-05-09 |
| EP1567507B1 (en) | 2006-06-14 |
| US7166628B2 (en) | 2007-01-23 |
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