LT4854B - Bifenilsulfonamidai kaip dvigubi angiotenzino ir endotelino receptorių antagonistai - Google Patents

Info

Publication number

LT4854B

LT4854B LT2000123A LT2000123A LT4854B LT 4854 B LT4854 B LT 4854B LT 2000123 A LT2000123 A LT 2000123A LT 2000123 A LT2000123 A LT 2000123A LT 4854 B LT4854 B LT 4854B

Authority

LT

Lithuania

Prior art keywords

methyl

dimethyl

biphenyl

isoxazolyl

oxo

Prior art date

1998-07-06

Links

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• Global Dossier
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• SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 title claims abstract description 70
• 102000015427 Angiotensins Human genes 0.000 title description 3
• 102000010180 Endothelin receptor Human genes 0.000 title description 3
• 108050001739 Endothelin receptor Proteins 0.000 title description 3
• 230000009977 dual effect Effects 0.000 title description 3
• 108010064733 Angiotensins Proteins 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 361
• 238000000034 method Methods 0.000 claims abstract description 58
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 206010020772 Hypertension Diseases 0.000 claims abstract description 8
• 201000010099 disease Diseases 0.000 claims abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• -1 1-oxopentyl Chemical group 0.000 claims description 753
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 620
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 258
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 246
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 234
• 229940124530 sulfonamide Drugs 0.000 claims description 173
• 235000010290 biphenyl Nutrition 0.000 claims description 125
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 239000001257 hydrogen Substances 0.000 claims description 67
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 65
• 239000002904 solvent Substances 0.000 claims description 57
• 150000002431 hydrogen Chemical class 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 239000000460 chlorine Substances 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 31
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• 239000004305 biphenyl Substances 0.000 claims description 21
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
• 229950006323 angiotensin ii Drugs 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 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 description 13
• 150000002148 esters Chemical class 0.000 claims description 13
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 11
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
• 102000005862 Angiotensin II Human genes 0.000 claims description 10
• 101800000733 Angiotensin-2 Proteins 0.000 claims description 10
• 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 description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 10
• 108050009340 Endothelin Proteins 0.000 claims description 9
• 102000002045 Endothelin Human genes 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• 230000001419 dependent effect Effects 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 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 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 7
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 238000006268 reductive amination reaction Methods 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
• 238000006751 Mitsunobu reaction Methods 0.000 claims description 5
• 230000010933 acylation Effects 0.000 claims description 5
• 238000005917 acylation reaction Methods 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
• 239000004327 boric acid Substances 0.000 claims description 5
• 230000027326 copulation Effects 0.000 claims description 5
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
• UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 4
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 206010019280 Heart failures Diseases 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 230000003213 activating effect Effects 0.000 claims description 3
• 230000001434 glomerular Effects 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
• SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• IDSDOGBFMPQENQ-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-formylphenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound O=C1N(CC=2C=C(C=O)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 IDSDOGBFMPQENQ-UHFFFAOYSA-N 0.000 claims description 2
• JTHQDJJYVYFEPX-UHFFFAOYSA-N 2-butyl-3-[[3-[[(3,4-dimethyl-1,2-oxazol-5-yl)-methylamino]methyl]-4-phenylphenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)CN(C1=C(C(=NO1)C)C)C)=O)CCCC2 JTHQDJJYVYFEPX-UHFFFAOYSA-N 0.000 claims description 2
• NKDJIJPGIVVJCN-UHFFFAOYSA-N 2-methylpropyl n-methylcarbamate Chemical compound CNC(=O)OCC(C)C NKDJIJPGIVVJCN-UHFFFAOYSA-N 0.000 claims description 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 201000001320 Atherosclerosis Diseases 0.000 claims description 2
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
• 208000037487 Endotoxemia Diseases 0.000 claims description 2
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 2
• 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims description 2
• 206010057671 Female sexual dysfunction Diseases 0.000 claims description 2
• 208000032843 Hemorrhage Diseases 0.000 claims description 2
• 208000019695 Migraine disease Diseases 0.000 claims description 2
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 2
• 108090000783 Renin Proteins 0.000 claims description 2
• 102100028255 Renin Human genes 0.000 claims description 2
• 230000001154 acute effect Effects 0.000 claims description 2
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 150000001450 anions Chemical class 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 208000006673 asthma Diseases 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 230000010261 cell growth Effects 0.000 claims description 2
• 201000001881 impotence Diseases 0.000 claims description 2
• 206010027599 migraine Diseases 0.000 claims description 2
• KXMBIKHULBVOSD-UHFFFAOYSA-N n-(4,5-dimethyl-1,2-oxazol-3-yl)-2-phenylbenzenesulfonamide Chemical compound CC1=C(C)ON=C1NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 KXMBIKHULBVOSD-UHFFFAOYSA-N 0.000 claims description 2
• 125000002524 organometallic group Chemical group 0.000 claims description 2
• 201000008312 primary pulmonary hypertension Diseases 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 208000037803 restenosis Diseases 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 10
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 3
• 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
• FFGKOKNUUYZYHF-UHFFFAOYSA-N 2-(4,5-dimethyl-1,2-oxazol-3-yl)-6-phenylbenzenesulfonamide Chemical compound CC1=C(C)ON=C1C1=CC=CC(C=2C=CC=CC=2)=C1S(N)(=O)=O FFGKOKNUUYZYHF-UHFFFAOYSA-N 0.000 claims 2
• GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims 2
• ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
• PMXDMWBBJJQEHD-UHFFFAOYSA-N 5-[3-methoxy-2,6-dimethyl-4-[[4-phenyl-3-(3,3,3-trifluoropropyl)phenyl]methoxy]-2H-pyridin-1-yl]-3,4-dimethyl-1,2-oxazole Chemical compound CC1=NOC(=C1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)CCC(F)(F)F)OC)C PMXDMWBBJJQEHD-UHFFFAOYSA-N 0.000 claims 2
• 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 2
• WNAFVJVEADYQAI-UHFFFAOYSA-N methyl 2-phenylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC=C1 WNAFVJVEADYQAI-UHFFFAOYSA-N 0.000 claims 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
• XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 claims 1
• LQVYLAPNXWMAQJ-UHFFFAOYSA-N 1-(3,4-dimethyl-1,2-oxazol-5-yl)-2,4-dimethyl-8-[(4-phenylphenyl)methyl]-5,6-dihydro-2H-pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=NOC(=C1C)N1C(N=C(C2=C1N(C(CC2)=O)CC2=CC=C(C=C2)C2=CC=CC=C2)C)C LQVYLAPNXWMAQJ-UHFFFAOYSA-N 0.000 claims 1
• INNGCXAJNSFBRR-UHFFFAOYSA-N 1-(4,5-dimethyl-1,2-oxazol-3-yl)-2,4-dimethyl-8-[(4-phenylphenyl)methyl]-5,6-dihydro-2H-pyrido[2,3-d]pyrimidin-7-one Chemical compound CC=1C(=NOC1C)N1C(N=C(C2=C1N(C(CC2)=O)CC2=CC=C(C=C2)C2=CC=CC=C2)C)C INNGCXAJNSFBRR-UHFFFAOYSA-N 0.000 claims 1
• NTEGHZGDMDXLHQ-UHFFFAOYSA-N 1-[[5-[[1-(4,5-dimethyl-1,2-oxazol-3-yl)-2-ethyl-5,7-dimethyl-2H-imidazo[4,5-b]pyridin-3-yl]methyl]-2-phenylphenyl]methyl]-3,3-dimethylpyrrolidin-2-one Chemical compound CC=1C(=NOC=1C)N1C(N(C2=NC(=CC(=C21)C)C)CC1=CC(=C(C=C1)C1=CC=CC=C1)CN1C(C(CC1)(C)C)=O)CC NTEGHZGDMDXLHQ-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
• JTUWRWHZYZMOJF-UHFFFAOYSA-N 2-(1-methylcyclopentyl)acetamide Chemical compound NC(=O)CC1(C)CCCC1 JTUWRWHZYZMOJF-UHFFFAOYSA-N 0.000 claims 1
• WLPDLZHYIZNBKB-UHFFFAOYSA-N 2-(3,4-dimethyl-1,2-oxazol-5-yl)-6-phenylbenzenesulfonamide Chemical compound CC1=NOC(C=2C(=C(C=3C=CC=CC=3)C=CC=2)S(N)(=O)=O)=C1C WLPDLZHYIZNBKB-UHFFFAOYSA-N 0.000 claims 1
• JQZDFAVENCRGSQ-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-(hydroxymethyl)phenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O=C1N(CC=2C=C(CO)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(CCCC)=NC21CCCC2 JQZDFAVENCRGSQ-UHFFFAOYSA-N 0.000 claims 1
• RWCUTWAIVHPLHO-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-(pyrazol-1-ylmethyl)phenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound O=C1N(CC=2C=C(CN3N=CC=C3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 RWCUTWAIVHPLHO-UHFFFAOYSA-N 0.000 claims 1
• SOCXXLMIWNNNRI-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-formylphenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O=C1N(CC=2C=C(C=O)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(CCCC)=NC21CCCC2 SOCXXLMIWNNNRI-UHFFFAOYSA-N 0.000 claims 1
• JMCQGPBILKTSCM-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenyl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)-N-methylbenzenesulfonamide Chemical compound CN(S(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2(C1=O)CCCC2)CCCC)C2=C(C(=NO2)C)C JMCQGPBILKTSCM-UHFFFAOYSA-N 0.000 claims 1
• KSGKOKPBZBHCDZ-UHFFFAOYSA-N 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenyl]-N-(4,5-dimethyl-1,2-oxazol-3-yl)-N-methylbenzenesulfonamide Chemical compound CN(S(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)CN1C(=NC2(C1=O)CCCC2)CCCC)C2=NOC(=C2C)C KSGKOKPBZBHCDZ-UHFFFAOYSA-N 0.000 claims 1
• HDRDIUYQWRKIFA-UHFFFAOYSA-N 2-[4-[(5-acetyl-4-chloro-2-propylimidazol-1-yl)methyl]phenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CCCC1=NC(Cl)=C(C(C)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 HDRDIUYQWRKIFA-UHFFFAOYSA-N 0.000 claims 1
• MYLVIZOINRBDHQ-UHFFFAOYSA-N 2-[4-[(5-acetyl-4-chloro-2-propylimidazol-1-yl)methyl]phenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound CCCC1=NC(Cl)=C(C(C)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 MYLVIZOINRBDHQ-UHFFFAOYSA-N 0.000 claims 1
• JVENKMCALAPJPX-UHFFFAOYSA-N 2-[5-[[1-(3,4-dimethyl-1,2-oxazol-5-yl)-2-ethyl-5,7-dimethyl-2H-imidazo[4,5-b]pyridin-3-yl]methyl]-2-phenylphenyl]acetonitrile Chemical compound C(#N)CC1=C(C=CC(=C1)CN1C(N(C=2C1=NC(=CC=2C)C)C1=C(C(=NO1)C)C)CC)C1=CC=CC=C1 JVENKMCALAPJPX-UHFFFAOYSA-N 0.000 claims 1
• ZBTYPUFFEQGRMY-UHFFFAOYSA-N 2-[5-[[1-(3,4-dimethyl-1,2-oxazol-5-yl)-3-methoxy-2,6-dimethyl-2H-pyridin-4-yl]oxymethyl]-2-phenylphenyl]propan-2-ol Chemical compound CC1=NOC(=C1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)C(C)(C)O)OC)C ZBTYPUFFEQGRMY-UHFFFAOYSA-N 0.000 claims 1
• SHPBODZKPBFUEI-UHFFFAOYSA-N 2-[5-[[1-(4,5-dimethyl-1,2-oxazol-3-yl)-3-methoxy-2,6-dimethyl-2H-pyridin-4-yl]oxymethyl]-2-phenylphenyl]propan-2-ol Chemical compound CC=1C(=NOC1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)C(C)(C)O)OC)C SHPBODZKPBFUEI-UHFFFAOYSA-N 0.000 claims 1
• UAWDIKMZFDCXTF-UHFFFAOYSA-N 2-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]-n-methylpyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NC)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C UAWDIKMZFDCXTF-UHFFFAOYSA-N 0.000 claims 1
• HHFRYVABFZFNOV-UHFFFAOYSA-N 2-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C HHFRYVABFZFNOV-UHFFFAOYSA-N 0.000 claims 1
• IKCHHLCRTPLOAT-UHFFFAOYSA-N 2-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]-n-methylpyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NC)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C IKCHHLCRTPLOAT-UHFFFAOYSA-N 0.000 claims 1
• OKCRUZOIERYSRO-UHFFFAOYSA-N 2-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl-propylamino]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1N(CCC)CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C OKCRUZOIERYSRO-UHFFFAOYSA-N 0.000 claims 1
• OPDPLJAIXFEIKZ-UHFFFAOYSA-N 2-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]methyl-(3,4-dimethyl-1,2-oxazol-5-yl)amino]acetaldehyde Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)CN(C1=C(C(=NO1)C)C)CC=O)=O)CCCC2 OPDPLJAIXFEIKZ-UHFFFAOYSA-N 0.000 claims 1
• IROKFJFUWCAYLW-UHFFFAOYSA-N 2-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]methyl-(4,5-dimethyl-1,2-oxazol-3-yl)amino]acetaldehyde Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)CN(C1=NOC(=C1C)C)CC=O)=O)CCCC2 IROKFJFUWCAYLW-UHFFFAOYSA-N 0.000 claims 1
• IWHLYJNLJPFIFN-UHFFFAOYSA-N 2-butyl-3-[[3-[[(3,4-dimethyl-1,2-oxazol-5-yl)-(2,2,2-trifluoroethyl)amino]methyl]-4-phenylphenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)CN(C1=C(C(=NO1)C)C)CC(F)(F)F)=O)CCCC2 IWHLYJNLJPFIFN-UHFFFAOYSA-N 0.000 claims 1
• SUDPNOJFFCDVJT-UHFFFAOYSA-N 2-butyl-3-[[3-[[(4,5-dimethyl-1,2-oxazol-3-yl)-methylamino]methyl]-4-phenylphenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)CN(C1=NOC(=C1C)C)C)=O)CCCC2 SUDPNOJFFCDVJT-UHFFFAOYSA-N 0.000 claims 1
• KSOOVOZETWHNBV-UHFFFAOYSA-N 2-butyl-5-chloro-3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]imidazole-4-carboxamide Chemical compound CCCCC1=NC(Cl)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 KSOOVOZETWHNBV-UHFFFAOYSA-N 0.000 claims 1
• KDCJTASHQAOLLN-UHFFFAOYSA-N 2-butyl-5-chloro-3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]imidazole-4-carboxamide Chemical compound CCCCC1=NC(Cl)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 KDCJTASHQAOLLN-UHFFFAOYSA-N 0.000 claims 1
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims 1
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
• PBNBNOYWIKWPBX-UHFFFAOYSA-N 2-phenylethyl 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylate Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)S(=O)(=O)NC=3C(=C(C)ON=3)C)C(CC)=NC2=CC=CC=1C(=O)OCCC1=CC=CC=C1 PBNBNOYWIKWPBX-UHFFFAOYSA-N 0.000 claims 1
• AKUSZFPCJFNRSZ-UHFFFAOYSA-N 3,4-dimethyl-1,2-oxazole Chemical compound CC1=CON=C1C AKUSZFPCJFNRSZ-UHFFFAOYSA-N 0.000 claims 1
• CEHAQIOELBVSCR-UHFFFAOYSA-N 3,4-dimethyl-5-[2-methyl-4-[(4-phenylphenyl)methoxy]-2H-quinolin-1-yl]-1,2-oxazole Chemical compound CC1=NOC(=C1C)N1C(C=C(C2=CC=CC=C12)OCC1=CC=C(C=C1)C1=CC=CC=C1)C CEHAQIOELBVSCR-UHFFFAOYSA-N 0.000 claims 1
• KVPZXQZKQUXLKE-UHFFFAOYSA-N 3,4-dimethyl-5-[4-[(4-phenylphenyl)methoxy]-2-propyl-2H-quinolin-1-yl]-1,2-oxazole Chemical compound CC1=NOC(=C1C)N1C(C=C(C2=CC=CC=C12)OCC1=CC=C(C=C1)C1=CC=CC=C1)CCC KVPZXQZKQUXLKE-UHFFFAOYSA-N 0.000 claims 1
• AGWCMIQTYZUVLM-UHFFFAOYSA-N 3-[2-butyl-3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-4-oxoquinazolin-6-yl]-1-methyl-1-propan-2-ylurea Chemical compound CCCCC1=NC2=CC=C(NC(=O)N(C)C(C)C)C=C2C(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C AGWCMIQTYZUVLM-UHFFFAOYSA-N 0.000 claims 1
• KNRLDEZBDRYBOY-UHFFFAOYSA-N 3-[2-ethyl-4-[(4-phenylphenyl)methoxy]-5,6,7,8-tetrahydro-2H-quinolin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C=C(C=2CCCCC1=2)OCC1=CC=C(C=C1)C1=CC=CC=C1)CC KNRLDEZBDRYBOY-UHFFFAOYSA-N 0.000 claims 1
• ISUWDVHBPPIKIS-UHFFFAOYSA-N 3-[2-ethyl-4-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]-2H-quinolin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC1C)N1C(C=C(C2=CC=CC=C12)OCC1=CC(=C(C=C1)C1=CC=CC=C1)C(F)(F)F)CC ISUWDVHBPPIKIS-UHFFFAOYSA-N 0.000 claims 1
• MOKHUNQEFBLVKR-UHFFFAOYSA-N 3-[3-methoxy-2,6-dimethyl-4-[(4-phenyl-3-propylphenyl)methoxy]-2H-pyridin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)CCC)OC)C MOKHUNQEFBLVKR-UHFFFAOYSA-N 0.000 claims 1
• HHJXGXXJHXBGTG-UHFFFAOYSA-N 3-[3-methoxy-2,6-dimethyl-4-[[4-phenyl-3-(3,3,3-trifluoropropyl)phenyl]methoxy]-2H-pyridin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)CCC(F)(F)F)OC)C HHJXGXXJHXBGTG-UHFFFAOYSA-N 0.000 claims 1
• JVTJSIMEDPAXKE-UHFFFAOYSA-N 3-[3-methoxy-4-[[3-(methoxymethyl)-4-phenylphenyl]methoxy]-2,6-dimethyl-2H-pyridin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)COC)OC)C JVTJSIMEDPAXKE-UHFFFAOYSA-N 0.000 claims 1
• IDCPAIGWLYSMAX-UHFFFAOYSA-N 3-[4-[(3-chloro-4-phenylphenyl)methoxy]-2-ethyl-2H-quinolin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound ClC1=C(C=CC(=C1)COC1=CC(N(C2=CC=CC=C12)C1=NOC(=C1C)C)CC)C1=CC=CC=C1 IDCPAIGWLYSMAX-UHFFFAOYSA-N 0.000 claims 1
• PWFBTXUZUGJVFX-UHFFFAOYSA-N 3-[4-[(3-chloro-4-phenylphenyl)methoxy]-2-ethyl-5,6,7,8-tetrahydro-2H-quinolin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound ClC1=C(C=CC(=C1)COC1=CC(N(C=2CCCCC1=2)C1=NOC(=C1C)C)CC)C1=CC=CC=C1 PWFBTXUZUGJVFX-UHFFFAOYSA-N 0.000 claims 1
• WTAMEJYBMZGEKT-UHFFFAOYSA-N 3-[4-[[3-(2,2-dimethylpropyl)-4-phenylphenyl]methoxy]-3-methoxy-2,6-dimethyl-2H-pyridin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)CC(C)(C)C)OC)C WTAMEJYBMZGEKT-UHFFFAOYSA-N 0.000 claims 1
• QALPQQGHEQFTOP-UHFFFAOYSA-N 3-[4-[[3-(2-ethoxyethyl)-4-phenylphenyl]methoxy]-3-methoxy-2,6-dimethyl-2H-pyridin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)CCOCC)OC)C QALPQQGHEQFTOP-UHFFFAOYSA-N 0.000 claims 1
• STFNCRWRGPQYQK-UHFFFAOYSA-N 3-[4-[[3-(2-fluoroethoxymethyl)-4-phenylphenyl]methoxy]-3-methoxy-2,6-dimethyl-2H-pyridin-1-yl]-4,5-dimethyl-1,2-oxazole Chemical compound CC=1C(=NOC=1C)N1C(C(=C(C=C1C)OCC1=CC(=C(C=C1)C1=CC=CC=C1)COCCF)OC)C STFNCRWRGPQYQK-UHFFFAOYSA-N 0.000 claims 1
• JGWYBBRQGZMTJS-UHFFFAOYSA-N 3-[[3-chloro-4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-5-ethyl-2-propylimidazole-4-carboxamide Chemical compound CCCC1=NC(CC)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(Cl)=C1 JGWYBBRQGZMTJS-UHFFFAOYSA-N 0.000 claims 1
• VMZDKIVJWMIZAL-UHFFFAOYSA-N 3-[[3-chloro-4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-5-ethyl-2-propylimidazole-4-carboxylic acid Chemical compound CCCC1=NC(CC)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(Cl)=C1 VMZDKIVJWMIZAL-UHFFFAOYSA-N 0.000 claims 1
• KVFKSZQFFSBGPR-UHFFFAOYSA-N 3-[[3-chloro-4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-5-ethyl-2-propylimidazole-4-carboxamide Chemical compound CCCC1=NC(CC)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(Cl)=C1 KVFKSZQFFSBGPR-UHFFFAOYSA-N 0.000 claims 1
• YQDSKWYFRXAEPO-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-3-[(3,3-dimethyl-2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]-2-ethoxy-n,n-dimethylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)N(C)C)=C2N1CC(C=1)=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=1CN1CCC(C)(C)C1=O YQDSKWYFRXAEPO-UHFFFAOYSA-N 0.000 claims 1
• IRVHJOVDMOTMPB-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxy-n,n-dimethylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)N(C)C)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C IRVHJOVDMOTMPB-UHFFFAOYSA-N 0.000 claims 1
• SIBGIUZFLOMKLO-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxy-n-methylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)NC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C SIBGIUZFLOMKLO-UHFFFAOYSA-N 0.000 claims 1
• SUHBSPVLBJRWOI-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylic acid Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C SUHBSPVLBJRWOI-UHFFFAOYSA-N 0.000 claims 1
• BPVMZOLHJDJXOV-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethyl-5-methylimidazole-4-carboxamide Chemical compound CCC1=NC(C)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 BPVMZOLHJDJXOV-UHFFFAOYSA-N 0.000 claims 1
• YQIIUFKHFLXJES-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylic acid Chemical compound CCC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C YQIIUFKHFLXJES-UHFFFAOYSA-N 0.000 claims 1
• HXVNENCEVFFGED-UHFFFAOYSA-N 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-5-ethyl-n-methyl-2-propylimidazole-4-carboxamide Chemical compound CCCC1=NC(CC)=C(C(=O)NC)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 HXVNENCEVFFGED-UHFFFAOYSA-N 0.000 claims 1
• CDSMAUKOUJCSSX-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-3-[(3,3-dimethyl-2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]-2-ethoxy-n,n-dimethylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)N(C)C)=C2N1CC(C=1)=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=1CN1CCC(C)(C)C1=O CDSMAUKOUJCSSX-UHFFFAOYSA-N 0.000 claims 1
• ZFWODATUNKDEJV-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-3-[(3,3-dimethyl-2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]-2-ethoxy-n-methylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)NC)=C2N1CC(C=1)=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=1CN1CCC(C)(C)C1=O ZFWODATUNKDEJV-UHFFFAOYSA-N 0.000 claims 1
• NNLJVCWOIUNIEI-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-3-[(3,3-dimethyl-2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylic acid Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=1)=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=1CN1CCC(C)(C)C1=O NNLJVCWOIUNIEI-UHFFFAOYSA-N 0.000 claims 1
• INTIKAQRZCDRBI-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxy-n,n-dimethylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)N(C)C)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C INTIKAQRZCDRBI-UHFFFAOYSA-N 0.000 claims 1
• QUEAZQAMFQPIOI-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxy-n-methylbenzimidazole-4-carboxamide Chemical compound CCOC1=NC2=CC=CC(C(=O)NC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C QUEAZQAMFQPIOI-UHFFFAOYSA-N 0.000 claims 1
• JTOQEOXWMOFAFU-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylic acid Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C JTOQEOXWMOFAFU-UHFFFAOYSA-N 0.000 claims 1
• RMIAFUMCUXHLQX-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethyl-5-methylimidazole-4-carboxamide Chemical compound CCC1=NC(C)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 RMIAFUMCUXHLQX-UHFFFAOYSA-N 0.000 claims 1
• KFAWBGWQMXOFHN-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylic acid Chemical compound CCC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C KFAWBGWQMXOFHN-UHFFFAOYSA-N 0.000 claims 1
• SLTTWKOOKFICRX-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-5-ethyl-2-propylimidazole-4-carboxamide Chemical compound CCCC1=NC(CC)=C(C(N)=O)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 SLTTWKOOKFICRX-UHFFFAOYSA-N 0.000 claims 1
• FJHLEDWXOJMMQH-UHFFFAOYSA-N 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-5-ethyl-n-methyl-2-propylimidazole-4-carboxamide Chemical compound CCCC1=NC(CC)=C(C(=O)NC)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 FJHLEDWXOJMMQH-UHFFFAOYSA-N 0.000 claims 1
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
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• 206010057672 Male sexual dysfunction Diseases 0.000 claims 1
• VNWXOVYRTYKMKA-UHFFFAOYSA-N N-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)ethanesulfonamide Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)N(C1=C(C(=NO1)C)C)S(=O)(=O)CC)=O)CCCC2 VNWXOVYRTYKMKA-UHFFFAOYSA-N 0.000 claims 1
• OFKUGKQTTIREGD-UHFFFAOYSA-N N-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)methanesulfonamide Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)N(C1=C(C(=NO1)C)C)S(=O)(=O)C)=O)CCCC2 OFKUGKQTTIREGD-UHFFFAOYSA-N 0.000 claims 1
• FMCVUYFRFPPGFT-UHFFFAOYSA-N N-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]-N-(4,5-dimethyl-1,2-oxazol-3-yl)ethanesulfonamide Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)N(C1=NOC(=C1C)C)S(=O)(=O)CC)=O)CCCC2 FMCVUYFRFPPGFT-UHFFFAOYSA-N 0.000 claims 1
• UHRYPBNNMKOPCA-UHFFFAOYSA-N N-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]-N-(4,5-dimethyl-1,2-oxazol-3-yl)methanesulfonamide Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)N(C1=NOC(=C1C)C)S(=O)(=O)C)=O)CCCC2 UHRYPBNNMKOPCA-UHFFFAOYSA-N 0.000 claims 1
• IPZNSHHAIWLDRR-UHFFFAOYSA-N N-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-phenylphenyl]-N-(4,5-dimethyl-1,2-oxazol-3-yl)propane-1-sulfonamide Chemical compound C(CCC)C1=NC2(C(N1CC1=CC(=C(C=C1)C1=CC=CC=C1)N(C1=NOC(=C1C)C)S(=O)(=O)CCC)=O)CCCC2 IPZNSHHAIWLDRR-UHFFFAOYSA-N 0.000 claims 1
• BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 claims 1
• 208000033626 Renal failure acute Diseases 0.000 claims 1
• 201000011040 acute kidney failure Diseases 0.000 claims 1
• 208000012998 acute renal failure Diseases 0.000 claims 1
• 125000003342 alkenyl group Chemical group 0.000 claims 1
• WOSHOXJMVPZFTG-UHFFFAOYSA-N benzyl 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylate Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)S(=O)(=O)NC3=C(C(C)=NO3)C)C(CC)=NC2=CC=CC=1C(=O)OCC1=CC=CC=C1 WOSHOXJMVPZFTG-UHFFFAOYSA-N 0.000 claims 1
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
• 208000020832 chronic kidney disease Diseases 0.000 claims 1
• 208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
• BFGSVQSGLQJDPT-UHFFFAOYSA-N ethyl 2-(2-phenylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C1=CC=CC=C1 BFGSVQSGLQJDPT-UHFFFAOYSA-N 0.000 claims 1
• AIYQIAGNVJJMAN-UHFFFAOYSA-N ethyl 2-[2-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-5-[(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]acetate Chemical compound CCOC(=O)CC1=CC(CN2C3=NC(C)=CC(C)=C3N=C2CC)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C AIYQIAGNVJJMAN-UHFFFAOYSA-N 0.000 claims 1
• 210000003904 glomerular cell Anatomy 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 claims 1
• 208000028867 ischemia Diseases 0.000 claims 1
• 210000003292 kidney cell Anatomy 0.000 claims 1
• 210000003584 mesangial cell Anatomy 0.000 claims 1
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
• UFZXANGVAOFGJL-UHFFFAOYSA-N methyl 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-3-[(3,3-dimethyl-2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylate Chemical compound CCOC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=1)=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=1CN1CCC(C)(C)C1=O UFZXANGVAOFGJL-UHFFFAOYSA-N 0.000 claims 1
• GVWNBDVESBUDMO-UHFFFAOYSA-N methyl 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylate Chemical compound CCOC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C GVWNBDVESBUDMO-UHFFFAOYSA-N 0.000 claims 1
• ISWGXOAQVXWQGY-UHFFFAOYSA-N methyl 3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylate Chemical compound CCC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC=1ON=C(C)C=1C ISWGXOAQVXWQGY-UHFFFAOYSA-N 0.000 claims 1
• YTXNGJLRWDQOBM-UHFFFAOYSA-N methyl 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-3-[(3,3-dimethyl-2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylate Chemical compound CCOC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=1)=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=1CN1CCC(C)(C)C1=O YTXNGJLRWDQOBM-UHFFFAOYSA-N 0.000 claims 1
• XZMWDKAPFHAOTO-UHFFFAOYSA-N methyl 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethoxybenzimidazole-4-carboxylate Chemical compound CCOC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C XZMWDKAPFHAOTO-UHFFFAOYSA-N 0.000 claims 1
• RMZNWYKHMAIJSL-UHFFFAOYSA-N methyl 3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-ethylbenzimidazole-4-carboxylate Chemical compound CCC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C RMZNWYKHMAIJSL-UHFFFAOYSA-N 0.000 claims 1
• XLCKUSNCRBAKDZ-UHFFFAOYSA-N methyl 5-chloro-3-[[4-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-2-propylimidazole-4-carboxylate Chemical compound CCCC1=NC(Cl)=C(C(=O)OC)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C=C1 XLCKUSNCRBAKDZ-UHFFFAOYSA-N 0.000 claims 1
• ZEKHOXWSBSVRSS-UHFFFAOYSA-N methyl 5-chloro-3-[[4-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]methyl]-2-propylimidazole-4-carboxylate Chemical compound CCCC1=NC(Cl)=C(C(=O)OC)N1CC1=CC=C(C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C=C1 ZEKHOXWSBSVRSS-UHFFFAOYSA-N 0.000 claims 1
• UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims 1
• DFOWPVLWLVJSIR-UHFFFAOYSA-N n-(4,5-dimethyl-1,2-oxazol-3-yl)-2-[2-(1-hydroxyethyl)-4-[(4-oxo-2-propyl-5,6,7,8-tetrahydrocyclohepta[d]imidazol-3-yl)methyl]phenyl]benzenesulfonamide Chemical compound CCCC1=NC=2CCCCC(=O)C=2N1CC(C=C1C(C)O)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=NOC(C)=C1C DFOWPVLWLVJSIR-UHFFFAOYSA-N 0.000 claims 1
• QPRHBARTFAYHFY-UHFFFAOYSA-N n-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]-2-phenylacetamide Chemical compound O=C1N(CC=2C=C(NC(=O)CC=3C=CC=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(CCCC)=NC21CCCC2 QPRHBARTFAYHFY-UHFFFAOYSA-N 0.000 claims 1
• PPDFOWBKEJXMLG-UHFFFAOYSA-N n-[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(4,5-dimethyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]phenyl]-3,3-dimethylbutanamide Chemical compound O=C1N(CC=2C=C(NC(=O)CC(C)(C)C)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC=2C(=C(C)ON=2)C)C(CCCC)=NC21CCCC2 PPDFOWBKEJXMLG-UHFFFAOYSA-N 0.000 claims 1
• JJLFKYFLDMZIMO-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-3-chloro-n-methylbenzamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)C=3C=C(Cl)C=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 JJLFKYFLDMZIMO-UHFFFAOYSA-N 0.000 claims 1
• GDKQYWQJLZOPOA-UHFFFAOYSA-N n-[[5-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]methyl]-4-fluoro-n-methylbenzamide Chemical compound O=C1N(CC=2C=C(CN(C)C(=O)C=3C=CC(F)=CC=3)C(=CC=2)C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)C(CCCC)=NC21CCCC2 GDKQYWQJLZOPOA-UHFFFAOYSA-N 0.000 claims 1
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