JP2002500619A - 置換ビフェニルイソオキサゾールスルホンアミド - Google Patents
置換ビフェニルイソオキサゾールスルホンアミドInfo
- Publication number
- JP2002500619A JP2002500619A JP52962097A JP52962097A JP2002500619A JP 2002500619 A JP2002500619 A JP 2002500619A JP 52962097 A JP52962097 A JP 52962097A JP 52962097 A JP52962097 A JP 52962097A JP 2002500619 A JP2002500619 A JP 2002500619A
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- oxazolyl
- isoxazolyl
- biphenyl
- methyl
- 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.)
- Ceased
Links
- KFJGHVOVYDCDOS-UHFFFAOYSA-N 1,1'-biphenyl;1,2-oxazole-3-sulfonamide Chemical class NS(=O)(=O)C=1C=CON=1.C1=CC=CC=C1C1=CC=CC=C1 KFJGHVOVYDCDOS-UHFFFAOYSA-N 0.000 title description 2
- -1 cycloalkenylalkyl Chemical group 0.000 claims abstract description 631
- 150000001875 compounds Chemical class 0.000 claims abstract description 283
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 83
- 125000003118 aryl group Chemical group 0.000 claims abstract description 59
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 20
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 18
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 17
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 102000002045 Endothelin Human genes 0.000 claims abstract description 10
- 108050009340 Endothelin Proteins 0.000 claims abstract description 10
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001721 carbon Chemical group 0.000 claims abstract description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 372
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 217
- 235000010290 biphenyl Nutrition 0.000 claims description 186
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 179
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 144
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 135
- 229940124530 sulfonamide Drugs 0.000 claims description 99
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 96
- SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 70
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 41
- 238000011282 treatment Methods 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 206010020772 Hypertension Diseases 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 16
- 125000004470 heterocyclooxy group Chemical group 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 102000005862 Angiotensin II Human genes 0.000 claims description 11
- 101800000733 Angiotensin-2 Proteins 0.000 claims description 11
- 229950006323 angiotensin ii Drugs 0.000 claims description 11
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 230000001434 glomerular Effects 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 206010019280 Heart failures Diseases 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 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
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 7
- 102000003729 Neprilysin Human genes 0.000 claims description 7
- 108090000028 Neprilysin Proteins 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000005541 ACE inhibitor Substances 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 6
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 6
- 108090000783 Renin Proteins 0.000 claims description 6
- 102100028255 Renin Human genes 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000002934 diuretic Substances 0.000 claims description 6
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
- 239000002461 renin inhibitor Substances 0.000 claims description 6
- 229940086526 renin-inhibitors Drugs 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims description 6
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 6
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims description 5
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000037487 Endotoxemia Diseases 0.000 claims description 5
- 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims description 5
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 5
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims description 5
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 201000008312 primary pulmonary hypertension Diseases 0.000 claims description 5
- 210000002536 stromal cell Anatomy 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- UZHZLWTWVKBXPA-UHFFFAOYSA-N N-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-2,2,2-trifluoroethanamine Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CNCC(F)(F)F UZHZLWTWVKBXPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 229940097217 cardiac glycoside Drugs 0.000 claims description 4
- 239000002368 cardiac glycoside Substances 0.000 claims description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 229930002534 steroid glycoside Natural products 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- USGSDZWGPOECAK-UHFFFAOYSA-N 2-[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]acetonitrile Chemical compound C(#N)CC1=C(C=CC(=C1)C1OC=CN1C1=C(C(=NO1)C)C)C1=CC=CC=C1 USGSDZWGPOECAK-UHFFFAOYSA-N 0.000 claims description 2
- GDBZBQLHCRXFFB-UHFFFAOYSA-N 2-phenylbenzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 GDBZBQLHCRXFFB-UHFFFAOYSA-N 0.000 claims description 2
- QUGYWVIGHQDGMZ-UHFFFAOYSA-N 3,4-dimethyl-5-[2-[3-(2-methylpropoxymethyl)-4-phenylphenyl]-2h-1,3-oxazol-3-yl]-1,2-oxazole Chemical compound CC(C)COCC1=CC(C2N(C=CO2)C2=C(C(C)=NO2)C)=CC=C1C1=CC=CC=C1 QUGYWVIGHQDGMZ-UHFFFAOYSA-N 0.000 claims description 2
- IOHFJLOGXVKAOM-UHFFFAOYSA-N 3,4-dimethyl-5-[2-[[5-(1,3-oxazol-2-yl)-2-phenylphenyl]methyl]-2H-1,3-oxazol-3-yl]-1,2-oxazole Chemical compound CC1=NOC(=C1C)N1C(OC=C1)CC1=C(C=CC(=C1)C=1OC=CN=1)C1=CC=CC=C1 IOHFJLOGXVKAOM-UHFFFAOYSA-N 0.000 claims description 2
- DCZPLENFARJCSV-UHFFFAOYSA-N 5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-N-methyl-2-phenylbenzamide Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)C(=O)NC DCZPLENFARJCSV-UHFFFAOYSA-N 0.000 claims description 2
- FAEOJFPPFANZGN-UHFFFAOYSA-N N-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-2,2,2-trifluoro-N-methylethanamine Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CN(CC(F)(F)F)C FAEOJFPPFANZGN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- KTPXYCOGWGATSP-UHFFFAOYSA-N n-cyclopropyl-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-2,2-dimethylpropanamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C(=CC(=CC=2)C=2OC=CN=2)CN(C2CC2)C(=O)C(C)(C)C)=C1C KTPXYCOGWGATSP-UHFFFAOYSA-N 0.000 claims description 2
- XPPNYNZMOQSBAA-UHFFFAOYSA-N n-cyclopropyl-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-2-methylpropanamide Chemical compound C1CC1N(C(=O)C(C)C)CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C XPPNYNZMOQSBAA-UHFFFAOYSA-N 0.000 claims description 2
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims 8
- 229940097420 Diuretic Drugs 0.000 claims 4
- 230000001882 diuretic effect Effects 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- CGMLTIBIMVAHSF-UHFFFAOYSA-N 1-[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]-4-phenylbutan-2-ol Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CC(CCC1=CC=CC=C1)O CGMLTIBIMVAHSF-UHFFFAOYSA-N 0.000 claims 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 229940047583 cetamide Drugs 0.000 claims 2
- 229930182470 glycoside Natural products 0.000 claims 2
- 150000002338 glycosides Chemical class 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 1
- ZSCNMSFOUJFSCQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-n-methyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=NN(C=2C=CC(Cl)=CC=2)C(C(F)(F)F)=C1C(=O)N(C)CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C ZSCNMSFOUJFSCQ-UHFFFAOYSA-N 0.000 claims 1
- OFYXRJHKRXHKCX-UHFFFAOYSA-N 1-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-3,3-dimethylpyrrolidin-2-one Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CN1C(C(CC1)(C)C)=O OFYXRJHKRXHKCX-UHFFFAOYSA-N 0.000 claims 1
- BIZFDQKCQAXRQW-UHFFFAOYSA-N 1-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-3-methylimidazolidin-2-one Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CN1C(N(CC1)C)=O BIZFDQKCQAXRQW-UHFFFAOYSA-N 0.000 claims 1
- AWFLDWWBOUNTND-UHFFFAOYSA-N 1-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-3-phenylimidazolidin-2-one Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CN1C(N(CC1)C1=CC=CC=C1)=O AWFLDWWBOUNTND-UHFFFAOYSA-N 0.000 claims 1
- IRYDDXBAIDRZEC-UHFFFAOYSA-N 1-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-3-propan-2-ylimidazolidin-2-one Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CN1C(N(CC1)C(C)C)=O IRYDDXBAIDRZEC-UHFFFAOYSA-N 0.000 claims 1
- HHZYOLBTDGDDOB-UHFFFAOYSA-N 1-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound CC1=NOC(=C1C)N1C(OC=C1)C1=CC(=C(C=C1)C1=CC=CC=C1)CN1C(CC(C1)(C)C)=O HHZYOLBTDGDDOB-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- INELUNPYSRUKLL-UHFFFAOYSA-N 1-tert-butyl-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-n-methyl-3-phenyl-2h-triazole-4-carboxamide Chemical compound C=1N(C(C)(C)C)NN(C=2C=CC=CC=2)C=1C(=O)N(C)CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C INELUNPYSRUKLL-UHFFFAOYSA-N 0.000 claims 1
- ZMIONMXXVCNVLO-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1OCC(=O)N(C)CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C ZMIONMXXVCNVLO-UHFFFAOYSA-N 0.000 claims 1
- WSCXPXIEEVKUFP-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-n-methylacetamide Chemical compound C=1C=CC=C(Cl)C=1CC(=O)N(C)CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C WSCXPXIEEVKUFP-UHFFFAOYSA-N 0.000 claims 1
- UGAPUOHUPJYDLC-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-n-methylacetamide Chemical compound C=1C=C(Cl)C=CC=1CC(=O)N(C)CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C UGAPUOHUPJYDLC-UHFFFAOYSA-N 0.000 claims 1
- HBGGXQHRNBXKQJ-UHFFFAOYSA-N 2-[2-[(4-acetylpiperazin-1-yl)methyl]-4-(1,3-oxazol-2-yl)phenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1CC1=CC(C=2OC=CN=2)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 HBGGXQHRNBXKQJ-UHFFFAOYSA-N 0.000 claims 1
- RXTCYASLCWVLGQ-UHFFFAOYSA-N 2-[[5-[3-(3,4-dimethyl-1,2-oxazol-5-yl)-2H-1,3-oxazol-2-yl]-2-phenylphenyl]methyl]isoindole-1,3-dione Chemical compound O=C1N(C(C2=CC=CC=C12)=O)CC1=C(C=CC(=C1)C1OC=CN1C1=C(C(=NO1)C)C)C1=CC=CC=C1 RXTCYASLCWVLGQ-UHFFFAOYSA-N 0.000 claims 1
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- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
Classifications
-
- 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
- C07D231/12—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
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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
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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
- A61P9/10—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
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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
- A61P9/12—Antihypertensives
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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
- C07D231/38—Nitrogen atoms
- C07D231/42—Benzene-sulfonamido pyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60397596A | 1996-02-20 | 1996-02-20 | |
| US08/603,975 | 1996-02-20 | ||
| US75471596A | 1996-11-21 | 1996-11-21 | |
| US08/754,715 | 1996-11-21 | ||
| US08/799,616 | 1997-02-13 | ||
| US08/799,616 US5846990A (en) | 1995-07-24 | 1997-02-13 | Substituted biphenyl isoxazole sulfonamides |
| PCT/US1997/003956 WO1997029748A1 (en) | 1996-02-20 | 1997-02-20 | Substituted biphenyl isoxazole sulfonamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002500619A true JP2002500619A (ja) | 2002-01-08 |
| JP2002500619A5 JP2002500619A5 (https=) | 2004-11-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP52962097A Ceased JP2002500619A (ja) | 1996-02-20 | 1997-02-20 | 置換ビフェニルイソオキサゾールスルホンアミド |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5846990A (https=) |
| EP (1) | EP0921800B1 (https=) |
| JP (1) | JP2002500619A (https=) |
| AT (1) | ATE264324T1 (https=) |
| AU (1) | AU720458B2 (https=) |
| CA (1) | CA2240043A1 (https=) |
| DE (1) | DE69728673T2 (https=) |
| ES (1) | ES2219762T3 (https=) |
| WO (1) | WO1997029748A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008509113A (ja) * | 2004-08-05 | 2008-03-27 | サノフイ−アベンテイス | N‐(1h‐インドリル)‐1h‐インドール‐2‐カルボキサミド誘導体、それらの調製法およびそれらの治療学的使用 |
| JP2008526820A (ja) * | 2005-01-07 | 2008-07-24 | サノフイ−アベンテイス | N−(ヘテロアリール)−1h−インドール−2−カルボキサミド誘導体及びバニロイドtrpv1受容体リガンドとしてのその使用 |
| JP2024523576A (ja) * | 2021-07-09 | 2024-06-28 | ヴィコール ファルマ アーベー | 新規の選択的アンジオテンシンii化合物 |
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| US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| JPH09124620A (ja) | 1995-10-11 | 1997-05-13 | Bristol Myers Squibb Co | 置換ビフェニルスルホンアミドエンドセリン拮抗剤 |
| EP0904077A4 (en) * | 1996-02-20 | 1999-12-22 | Bristol Myers Squibb Co | PROCESSES FOR THE PRODUCTION OF BIPHENYL ISOXAZOLE SULFAMIDES |
| TW536540B (en) * | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| AP9901643A0 (en) | 1997-04-28 | 1999-10-02 | Texas Biotechnology Corp | Sulfonamides for treatment of endothelin-mediated disorders. |
| AU742506B2 (en) * | 1997-10-17 | 2002-01-03 | Eurogene Limited | The use of inhibitors of the renin-angiotensin system |
| DE19813354A1 (de) * | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| US6638937B2 (en) | 1998-07-06 | 2003-10-28 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| WO2000001389A1 (en) * | 1998-07-06 | 2000-01-13 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
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| IL144708A0 (en) * | 1999-03-19 | 2002-06-30 | Bristol Myers Squibb Co | Methods for the preparation of biphenyl isoxazole sulfonamide derivatives |
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| WO1993023404A1 (en) * | 1992-05-19 | 1993-11-25 | Immunopharmaceutics, Inc. | Compounds that modulate endothelin activity |
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-
1997
- 1997-02-13 US US08/799,616 patent/US5846990A/en not_active Expired - Lifetime
- 1997-02-20 DE DE69728673T patent/DE69728673T2/de not_active Expired - Fee Related
- 1997-02-20 EP EP97915055A patent/EP0921800B1/en not_active Expired - Lifetime
- 1997-02-20 WO PCT/US1997/003956 patent/WO1997029748A1/en not_active Ceased
- 1997-02-20 ES ES97915055T patent/ES2219762T3/es not_active Expired - Lifetime
- 1997-02-20 JP JP52962097A patent/JP2002500619A/ja not_active Ceased
- 1997-02-20 AT AT97915055T patent/ATE264324T1/de not_active IP Right Cessation
- 1997-02-20 CA CA002240043A patent/CA2240043A1/en not_active Abandoned
- 1997-02-20 AU AU22098/97A patent/AU720458B2/en not_active Ceased
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008509113A (ja) * | 2004-08-05 | 2008-03-27 | サノフイ−アベンテイス | N‐(1h‐インドリル)‐1h‐インドール‐2‐カルボキサミド誘導体、それらの調製法およびそれらの治療学的使用 |
| JP2008526820A (ja) * | 2005-01-07 | 2008-07-24 | サノフイ−アベンテイス | N−(ヘテロアリール)−1h−インドール−2−カルボキサミド誘導体及びバニロイドtrpv1受容体リガンドとしてのその使用 |
| JP2024523576A (ja) * | 2021-07-09 | 2024-06-28 | ヴィコール ファルマ アーベー | 新規の選択的アンジオテンシンii化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0921800B1 (en) | 2004-04-14 |
| AU720458B2 (en) | 2000-06-01 |
| ATE264324T1 (de) | 2004-04-15 |
| WO1997029748A1 (en) | 1997-08-21 |
| ES2219762T3 (es) | 2004-12-01 |
| EP0921800A4 (en) | 2000-12-06 |
| DE69728673T2 (de) | 2005-03-31 |
| DE69728673D1 (de) | 2004-05-19 |
| EP0921800A1 (en) | 1999-06-16 |
| US5846990A (en) | 1998-12-08 |
| AU2209897A (en) | 1997-09-02 |
| CA2240043A1 (en) | 1997-08-21 |
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