HRP20110874T1 - Derivati sulfonamida i njihova uporaba za modulaciju metaloproteinaza - Google Patents
Derivati sulfonamida i njihova uporaba za modulaciju metaloproteinaza Download PDFInfo
- Publication number
- HRP20110874T1 HRP20110874T1 HR20110874T HRP20110874T HRP20110874T1 HR P20110874 T1 HRP20110874 T1 HR P20110874T1 HR 20110874 T HR20110874 T HR 20110874T HR P20110874 T HRP20110874 T HR P20110874T HR P20110874 T1 HRP20110874 T1 HR P20110874T1
- Authority
- HR
- Croatia
- Prior art keywords
- dihydroisoquinolin
- hydroxyformamide
- sulfonyl
- ethyl
- methyl
- Prior art date
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- 102000005741 Metalloproteases Human genes 0.000 title claims 2
- 108010006035 Metalloproteases Proteins 0.000 title claims 2
- 229940124530 sulfonamide Drugs 0.000 title abstract 2
- 150000003456 sulfonamides Chemical class 0.000 title abstract 2
- 206010014561 Emphysema Diseases 0.000 claims abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract 2
- 201000011510 cancer Diseases 0.000 claims abstract 2
- 208000027866 inflammatory disease Diseases 0.000 claims abstract 2
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract 2
- 230000004770 neurodegeneration Effects 0.000 claims abstract 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract 2
- 238000011321 prophylaxis Methods 0.000 claims abstract 2
- 208000023504 respiratory system disease Diseases 0.000 claims abstract 2
- 238000011282 treatment Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- -1 2-Tetrahydrofuran-2-ylethyl Chemical group 0.000 claims 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 3
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- HBHNAXYODTZBIQ-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-pyridin-3-ylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1=CC=CN=C1 HBHNAXYODTZBIQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- XEUGJRJOQXSUJB-UHFFFAOYSA-N 2-[2-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[formyl(hydroxy)amino]ethyl]cyclopropane-1-carboxylic acid Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(N(O)C=O)C1CC1C(O)=O XEUGJRJOQXSUJB-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RKERBEVAOORCSE-UHFFFAOYSA-N ethyl 2-[2-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[formyl(hydroxy)amino]ethyl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(N(O)C=O)CS(=O)(=O)N1CC2=CC(OC)=C(OC)C=C2CC1 RKERBEVAOORCSE-UHFFFAOYSA-N 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- SCRHWSMCASGPDS-JKSUJKDBSA-N n-[(1r)-2-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[(2r)-oxolan-2-yl]ethyl]-n-hydroxyformamide Chemical compound C([C@@H]1[C@H](CS(=O)(=O)N2CC3=CC(Cl)=CC=C3CC2)N(C=O)O)CCO1 SCRHWSMCASGPDS-JKSUJKDBSA-N 0.000 claims 1
- RFNRGHOYNHMJKX-HUUCEWRRSA-N n-[(1s)-2-[(5-fluoro-1,3-dihydroisoindol-2-yl)sulfonyl]-1-[(2r)-oxolan-2-yl]ethyl]-n-hydroxyformamide Chemical compound C([C@@H]1[C@@H](CS(=O)(=O)N2CC3=CC(F)=CC=C3C2)N(C=O)O)CCO1 RFNRGHOYNHMJKX-HUUCEWRRSA-N 0.000 claims 1
- SCRHWSMCASGPDS-HZPDHXFCSA-N n-[(1s)-2-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[(2r)-oxolan-2-yl]ethyl]-n-hydroxyformamide Chemical compound C([C@@H]1[C@@H](CS(=O)(=O)N2CC3=CC(Cl)=CC=C3CC2)N(C=O)O)CCO1 SCRHWSMCASGPDS-HZPDHXFCSA-N 0.000 claims 1
- HGYLFYNRJRYCAB-ZIAGYGMSSA-N n-[(2s,3s)-1-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3,4-dihydroxybutan-2-yl]-n-hydroxyformamide Chemical compound C1CN(S(=O)(=O)C[C@H]([C@H](O)CO)N(O)C=O)CC2=C1C=C(OC)C(OC)=C2 HGYLFYNRJRYCAB-ZIAGYGMSSA-N 0.000 claims 1
- WKKUXZKHDXDAAV-UHFFFAOYSA-N n-[1-(1,3-dihydroisoindol-2-ylsulfonyl)-4-phenylbutan-2-yl]-n-hydroxyformamide Chemical compound C1C2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)CCC1=CC=CC=C1 WKKUXZKHDXDAAV-UHFFFAOYSA-N 0.000 claims 1
- HYWIFAAOAYGLMS-UHFFFAOYSA-N n-[1-(1,3-dihydroisoindol-2-ylsulfonyl)-4-phenylbutan-2-yl]hydroxylamine Chemical compound C1C2=CC=CC=C2CN1S(=O)(=O)CC(NO)CCC1=CC=CC=C1 HYWIFAAOAYGLMS-UHFFFAOYSA-N 0.000 claims 1
- VWCRYOUHTIBPLW-UHFFFAOYSA-N n-[1-(1-benzylpiperidin-4-yl)-2-[(7-fluoro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(F)C=C2CN1S(=O)(=O)CC(N(C=O)O)C(CC1)CCN1CC1=CC=CC=C1 VWCRYOUHTIBPLW-UHFFFAOYSA-N 0.000 claims 1
- CNTYVMZJXNMVKO-UHFFFAOYSA-N n-[1-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-3-methyl-3-morpholin-4-ylbutan-2-yl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(O)C=O)C(C)(C)N1CCOCC1 CNTYVMZJXNMVKO-UHFFFAOYSA-N 0.000 claims 1
- BOLQPSGSQMDRSK-UHFFFAOYSA-N n-[1-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-4-phenylbutan-2-yl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)CCC1=CC=CC=C1 BOLQPSGSQMDRSK-UHFFFAOYSA-N 0.000 claims 1
- SFGIQPJRUWTRGJ-UHFFFAOYSA-N n-[1-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-4-phenylbutan-2-yl]hydroxylamine Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(NO)CCC1=CC=CC=C1 SFGIQPJRUWTRGJ-UHFFFAOYSA-N 0.000 claims 1
- VSOUJKWGYDTUDL-UHFFFAOYSA-N n-[1-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)heptan-2-yl]-n-hydroxyformamide Chemical compound C1=CC=C2CN(S(=O)(=O)CC(CCCCC)N(O)C=O)CCC2=C1 VSOUJKWGYDTUDL-UHFFFAOYSA-N 0.000 claims 1
- ULJDHHLCQGDCJX-UHFFFAOYSA-N n-[1-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)heptan-2-yl]hydroxylamine Chemical compound C1=CC=C2CN(S(=O)(=O)CC(CCCCC)NO)CCC2=C1 ULJDHHLCQGDCJX-UHFFFAOYSA-N 0.000 claims 1
- AHSVBOKUQXCHCU-MUMRKEEXSA-N n-[1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(6-propan-2-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC(C(C)C)=CC=C2CN1S(=O)(=O)CC(N(O)C=O)[C@H]1COC(C)(C)O1 AHSVBOKUQXCHCU-MUMRKEEXSA-N 0.000 claims 1
- JIPISKQEGLKCDG-OEMAIJDKSA-N n-[1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[7-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1C(N(O)C=O)CS(=O)(=O)N1CC2=CC(C(F)(F)F)=CC=C2CC1 JIPISKQEGLKCDG-OEMAIJDKSA-N 0.000 claims 1
- FYIJVFINOXAXIP-UHFFFAOYSA-N n-[1-[(5-fluoro-1,3-dihydroisoindol-2-yl)sulfonyl]-4,4-dimethylpentan-2-yl]-n-hydroxyformamide Chemical compound C1=C(F)C=C2CN(S(=O)(=O)CC(CC(C)(C)C)N(O)C=O)CC2=C1 FYIJVFINOXAXIP-UHFFFAOYSA-N 0.000 claims 1
- MFQJEWCQJDZBPM-UHFFFAOYSA-N n-[1-[(6,7-dichloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-ethylpentan-2-yl]-n-hydroxyformamide Chemical compound ClC1=C(Cl)C=C2CN(S(=O)(=O)CC(C(CC)CC)N(O)C=O)CCC2=C1 MFQJEWCQJDZBPM-UHFFFAOYSA-N 0.000 claims 1
- IQZOSOGJPNQYLX-UHFFFAOYSA-N n-[1-[(6,7-dichloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-hydroxypropan-2-yl]-n-hydroxyformamide Chemical compound ClC1=C(Cl)C=C2CN(S(=O)(=O)CC(CO)N(O)C=O)CCC2=C1 IQZOSOGJPNQYLX-UHFFFAOYSA-N 0.000 claims 1
- AQKZBPQFLLITQC-UHFFFAOYSA-N n-[1-[(6,7-dichloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-methylbutan-2-yl]-n-hydroxyformamide Chemical compound ClC1=C(Cl)C=C2CN(S(=O)(=O)CC(C(C)C)N(O)C=O)CCC2=C1 AQKZBPQFLLITQC-UHFFFAOYSA-N 0.000 claims 1
- BRRDNIRMEVMACW-UHFFFAOYSA-N n-[1-[(6,7-dichloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4,4-dimethylpentan-2-yl]-n-hydroxyformamide Chemical compound ClC1=C(Cl)C=C2CN(S(=O)(=O)CC(CC(C)(C)C)N(O)C=O)CCC2=C1 BRRDNIRMEVMACW-UHFFFAOYSA-N 0.000 claims 1
- SOHXUFDSBROHSD-UHFFFAOYSA-N n-[1-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3,3-dimethylbutan-2-yl]-n-hydroxyformamide Chemical compound C1CN(S(=O)(=O)CC(N(O)C=O)C(C)(C)C)CC2=C1C=C(OC)C(OC)=C2 SOHXUFDSBROHSD-UHFFFAOYSA-N 0.000 claims 1
- KQDITKVURPGKML-UHFFFAOYSA-N n-[1-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-ethylpentan-2-yl]-n-hydroxyformamide Chemical compound COC1=C(OC)C=C2CN(S(=O)(=O)CC(C(CC)CC)N(O)C=O)CCC2=C1 KQDITKVURPGKML-UHFFFAOYSA-N 0.000 claims 1
- HJJCNHRDJSHQMJ-UHFFFAOYSA-N n-[1-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-phenylbutan-2-yl]-n-hydroxyformamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(N(O)C=O)CCC1=CC=CC=C1 HJJCNHRDJSHQMJ-UHFFFAOYSA-N 0.000 claims 1
- WSPYSMLXCOONNI-UHFFFAOYSA-N n-[1-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-phenylbutan-2-yl]hydroxylamine Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(NO)CCC1=CC=CC=C1 WSPYSMLXCOONNI-UHFFFAOYSA-N 0.000 claims 1
- GFHYYUKVCOWXPH-UHFFFAOYSA-N n-[1-[(7-bromo-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-2-methylpropan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Br)C=C2CN(S(=O)(=O)CC(C)(C)N(O)C=O)CCC2=C1 GFHYYUKVCOWXPH-UHFFFAOYSA-N 0.000 claims 1
- PAGJNWKELVWJRP-UHFFFAOYSA-N n-[1-[(7-bromo-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-ethylpentan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Br)C=C2CN(S(=O)(=O)CC(C(CC)CC)N(O)C=O)CCC2=C1 PAGJNWKELVWJRP-UHFFFAOYSA-N 0.000 claims 1
- PWNIOEINAFJMOR-UHFFFAOYSA-N n-[1-[(7-bromo-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-methylpentan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Br)C=C2CN(S(=O)(=O)CC(CC(C)C)N(O)C=O)CCC2=C1 PWNIOEINAFJMOR-UHFFFAOYSA-N 0.000 claims 1
- VHXPKZQWUWXJAP-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3,3-dimethylbutan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Cl)C=C2CN(S(=O)(=O)CC(C(C)(C)C)N(O)C=O)CCC2=C1 VHXPKZQWUWXJAP-UHFFFAOYSA-N 0.000 claims 1
- FTHKJKYWCYJWCN-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-phenoxypropan-2-yl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Cl)C=C2CN1S(=O)(=O)CC(N(C=O)O)COC1=CC=CC=C1 FTHKJKYWCYJWCN-UHFFFAOYSA-N 0.000 claims 1
- GPWFQKMYGGCEOS-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-phenylmethoxypropan-2-yl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Cl)C=C2CN1S(=O)(=O)CC(N(C=O)O)COCC1=CC=CC=C1 GPWFQKMYGGCEOS-UHFFFAOYSA-N 0.000 claims 1
- QTGFEWAPUUIHNU-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4,4-dimethylpentan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Cl)C=C2CN(S(=O)(=O)CC(CC(C)(C)C)N(O)C=O)CCC2=C1 QTGFEWAPUUIHNU-UHFFFAOYSA-N 0.000 claims 1
- FRAQVJJXBSUXEL-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-hydroxybutan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Cl)C=C2CN(S(=O)(=O)CC(CCO)N(O)C=O)CCC2=C1 FRAQVJJXBSUXEL-UHFFFAOYSA-N 0.000 claims 1
- BHJLXIWRTQQZJL-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-pyridin-3-ylbutan-2-yl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Cl)C=C2CN1S(=O)(=O)CC(N(C=O)O)CCC1=CC=CN=C1 BHJLXIWRTQQZJL-UHFFFAOYSA-N 0.000 claims 1
- BGLCHWSPVZAOGZ-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-5,5,5-trifluoropentan-2-yl]-n-hydroxyformamide Chemical compound C1=C(Cl)C=C2CN(S(=O)(=O)CC(CCC(F)(F)F)N(C=O)O)CCC2=C1 BGLCHWSPVZAOGZ-UHFFFAOYSA-N 0.000 claims 1
- MSBWGJMTZMWVHH-UHFFFAOYSA-N n-[1-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonylmethyl]cyclopentyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Cl)C=C2CN1S(=O)(=O)CC1(N(C=O)O)CCCC1 MSBWGJMTZMWVHH-UHFFFAOYSA-N 0.000 claims 1
- MLIMXAYZDCIEEX-UHFFFAOYSA-N n-[1-[(7-tert-butyl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-3-phenylmethoxypropan-2-yl]-n-hydroxyformamide Chemical compound C1C2=CC(C(C)(C)C)=CC=C2CCN1S(=O)(=O)CC(N(O)C=O)COCC1=CC=CC=C1 MLIMXAYZDCIEEX-UHFFFAOYSA-N 0.000 claims 1
- LSALXDGBOVCTTD-UHFFFAOYSA-N n-[1-[(7-tert-butyl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-methylsulfanylbutan-2-yl]-n-hydroxyformamide Chemical compound C1=C(C(C)(C)C)C=C2CN(S(=O)(=O)CC(CCSC)N(O)C=O)CCC2=C1 LSALXDGBOVCTTD-UHFFFAOYSA-N 0.000 claims 1
- PYYKCTRYCUZZSR-UHFFFAOYSA-N n-[1-[[7-(4-fluorophenyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]-3-methylbutan-2-yl]-n-hydroxyformamide Chemical compound C1=C2CN(S(=O)(=O)CC(C(C)C)N(O)C=O)CCC2=CC=C1C1=CC=C(F)C=C1 PYYKCTRYCUZZSR-UHFFFAOYSA-N 0.000 claims 1
- BOOLTMXVQGRMMK-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(5-fluoro-1,3-dihydroisoindol-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1C2=CC=C(F)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 BOOLTMXVQGRMMK-UHFFFAOYSA-N 0.000 claims 1
- MSSSOOPNNLEKJK-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(6,7-dichloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC(Cl)=C(Cl)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 MSSSOOPNNLEKJK-UHFFFAOYSA-N 0.000 claims 1
- FORHNNSQSCAWEW-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(N(O)C=O)C1CCCC1 FORHNNSQSCAWEW-UHFFFAOYSA-N 0.000 claims 1
- SDYGQINSBKWKNK-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(6-propan-2-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC(C(C)C)=CC=C2CN1S(=O)(=O)CC(N(O)C=O)C1CCCC1 SDYGQINSBKWKNK-UHFFFAOYSA-N 0.000 claims 1
- CCGKYFDPQAQFKK-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(7-fluoro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(F)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 CCGKYFDPQAQFKK-UHFFFAOYSA-N 0.000 claims 1
- CESHIZIFSAZNOP-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(7-phenyl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CCCC1C(N(C=O)O)CS(=O)(=O)N(CC1=C2)CCC1=CC=C2C1=CC=CC=C1 CESHIZIFSAZNOP-UHFFFAOYSA-N 0.000 claims 1
- QMWORSFEWOYTFH-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1C2=CC(OC(C)C)=CC=C2CCN1S(=O)(=O)CC(N(O)C=O)C1CCCC1 QMWORSFEWOYTFH-UHFFFAOYSA-N 0.000 claims 1
- KMIRRPJAIRUJPJ-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(7-pyridin-4-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CCCC1C(N(C=O)O)CS(=O)(=O)N(CC1=C2)CCC1=CC=C2C1=CC=NC=C1 KMIRRPJAIRUJPJ-UHFFFAOYSA-N 0.000 claims 1
- BREHTXDEACXXAK-UHFFFAOYSA-N n-[1-cyclopentyl-2-[(7-thiophen-3-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CCCC1C(N(C=O)O)CS(=O)(=O)N(CC1=C2)CCC1=CC=C2C=1C=CSC=1 BREHTXDEACXXAK-UHFFFAOYSA-N 0.000 claims 1
- OZEOLFHFQPYCRX-UHFFFAOYSA-N n-[1-cyclopentyl-2-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 OZEOLFHFQPYCRX-UHFFFAOYSA-N 0.000 claims 1
- REWWQCKKEGAVID-UHFFFAOYSA-N n-[1-cyclopentyl-2-[[7-(3-hydroxyphenyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CCCC1C(N(C=O)O)CS(=O)(=O)N(CC1=C2)CCC1=CC=C2C1=CC=CC(O)=C1 REWWQCKKEGAVID-UHFFFAOYSA-N 0.000 claims 1
- WJPPIUCUJYATOV-UHFFFAOYSA-N n-[1-cyclopentyl-2-[[7-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(C(F)(F)F)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 WJPPIUCUJYATOV-UHFFFAOYSA-N 0.000 claims 1
- IOVUNXAYQQUSGV-UHFFFAOYSA-N n-[1-cyclopropyl-2-(1,3-dihydroisoindol-2-ylsulfonyl)ethyl]-n-hydroxyformamide Chemical compound C1C2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1CC1 IOVUNXAYQQUSGV-UHFFFAOYSA-N 0.000 claims 1
- YOWIRQFKTLZIIS-UHFFFAOYSA-N n-[1-cyclopropyl-2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1CC1 YOWIRQFKTLZIIS-UHFFFAOYSA-N 0.000 claims 1
- GJHQBZTUOMBBNQ-UHFFFAOYSA-N n-[1-cyclopropyl-2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)ethyl]hydroxylamine Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(NO)C1CC1 GJHQBZTUOMBBNQ-UHFFFAOYSA-N 0.000 claims 1
- ZYCUEXDACSDMOL-UHFFFAOYSA-N n-[1-cyclopropyl-2-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(N(O)C=O)C1CC1 ZYCUEXDACSDMOL-UHFFFAOYSA-N 0.000 claims 1
- MOEVZCOHVVNXMI-UHFFFAOYSA-N n-[1-cyclopropyl-2-[(6-propan-2-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC(C(C)C)=CC=C2CN1S(=O)(=O)CC(N(O)C=O)C1CC1 MOEVZCOHVVNXMI-UHFFFAOYSA-N 0.000 claims 1
- KAKBRWMOTVHQHP-UHFFFAOYSA-N n-[1-cyclopropyl-2-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1CC1 KAKBRWMOTVHQHP-UHFFFAOYSA-N 0.000 claims 1
- XNWHEHIDCHAQJQ-UHFFFAOYSA-N n-[1-cyclopropyl-2-[[7-(4-fluorophenyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC1C(N(C=O)O)CS(=O)(=O)N(CC1=C2)CCC1=CC=C2C1=CC=C(F)C=C1 XNWHEHIDCHAQJQ-UHFFFAOYSA-N 0.000 claims 1
- YEYJGTYBIXXXGO-UHFFFAOYSA-N n-[1-cyclopropyl-2-[[7-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(C(F)(F)F)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CC1 YEYJGTYBIXXXGO-UHFFFAOYSA-N 0.000 claims 1
- RVUOJQJSJAKXOI-YSSOQSIOSA-N n-[2-(1,3-dihydroisoindol-2-ylsulfonyl)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1C(N(O)C=O)CS(=O)(=O)N1CC2=CC=CC=C2C1 RVUOJQJSJAKXOI-YSSOQSIOSA-N 0.000 claims 1
- RCNGSVDQIWIMHW-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-(6-methoxypyridin-3-yl)ethyl]-n-hydroxyformamide Chemical compound C1=NC(OC)=CC=C1C(N(O)C=O)CS(=O)(=O)N1CC2=CC=CC=C2CC1 RCNGSVDQIWIMHW-UHFFFAOYSA-N 0.000 claims 1
- GHCKEMOKFQMKKS-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-(6-methoxypyridin-3-yl)ethyl]hydroxylamine Chemical compound C1=NC(OC)=CC=C1C(NO)CS(=O)(=O)N1CC2=CC=CC=C2CC1 GHCKEMOKFQMKKS-UHFFFAOYSA-N 0.000 claims 1
- NMUOOUICJGKGRE-OEMAIJDKSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1C(N(O)C=O)CS(=O)(=O)N1CC2=CC=CC=C2CC1 NMUOOUICJGKGRE-OEMAIJDKSA-N 0.000 claims 1
- QBZAKIRWKRGARF-YSSOQSIOSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]hydroxylamine Chemical compound O1C(C)(C)OC[C@@H]1C(NO)CS(=O)(=O)N1CC2=CC=CC=C2CC1 QBZAKIRWKRGARF-YSSOQSIOSA-N 0.000 claims 1
- ULMVRJBATBTYCL-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-pyridin-3-ylethyl]hydroxylamine Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(NO)C1=CC=CN=C1 ULMVRJBATBTYCL-UHFFFAOYSA-N 0.000 claims 1
- XLIPSRBIYAIREO-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-pyrimidin-2-ylethyl]hydroxylamine Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(NO)C1=NC=CC=N1 XLIPSRBIYAIREO-UHFFFAOYSA-N 0.000 claims 1
- WWMXPWXUCFALMR-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-pyrimidin-5-ylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1=CN=CN=C1 WWMXPWXUCFALMR-UHFFFAOYSA-N 0.000 claims 1
- UMUFUQZLMVWLDL-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-thiophen-2-ylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C1=CC=CS1 UMUFUQZLMVWLDL-UHFFFAOYSA-N 0.000 claims 1
- MJVXUZSNTYHBGN-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-thiophen-2-ylethyl]hydroxylamine Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(NO)C1=CC=CS1 MJVXUZSNTYHBGN-UHFFFAOYSA-N 0.000 claims 1
- RDAUFKOPPVIISI-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-thiophen-3-ylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(N(C=O)O)C=1C=CSC=1 RDAUFKOPPVIISI-UHFFFAOYSA-N 0.000 claims 1
- WLSYZUZDZVRLPN-UHFFFAOYSA-N n-[2-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)-1-thiophen-3-ylethyl]hydroxylamine Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)CC(NO)C=1C=CSC=1 WLSYZUZDZVRLPN-UHFFFAOYSA-N 0.000 claims 1
- QPVJJUAPVXEAMA-KPMSDPLLSA-N n-[2-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-n-hydroxyformamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(N(O)C=O)[C@H]1COC(C)(C)O1 QPVJJUAPVXEAMA-KPMSDPLLSA-N 0.000 claims 1
- BLMDGFWRRXLILT-FBMWCMRBSA-N n-[2-[(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]hydroxylamine Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1S(=O)(=O)CC(NO)[C@H]1COC(C)(C)O1 BLMDGFWRRXLILT-FBMWCMRBSA-N 0.000 claims 1
- IMHIBDPIRJIAIX-UHFFFAOYSA-N n-[2-[(7-bromo-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-cyclopentylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Br)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 IMHIBDPIRJIAIX-UHFFFAOYSA-N 0.000 claims 1
- ONJXVBWMIMCJAO-OEMAIJDKSA-N n-[2-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1C(N(O)C=O)CS(=O)(=O)N1CC2=CC(Cl)=CC=C2CC1 ONJXVBWMIMCJAO-OEMAIJDKSA-N 0.000 claims 1
- AYBONFWBZHJTEH-UHFFFAOYSA-N n-[2-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-cyclopentylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Cl)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CCCC1 AYBONFWBZHJTEH-UHFFFAOYSA-N 0.000 claims 1
- VIOORFHSPKRORY-UHFFFAOYSA-N n-[2-[(7-chloro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-cyclopropylethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(Cl)C=C2CN1S(=O)(=O)CC(N(C=O)O)C1CC1 VIOORFHSPKRORY-UHFFFAOYSA-N 0.000 claims 1
- ZTXMDOMIWZWWFM-UHFFFAOYSA-N n-[2-[(7-fluoro-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-(furan-3-yl)ethyl]-n-hydroxyformamide Chemical compound C1CC2=CC=C(F)C=C2CN1S(=O)(=O)CC(N(C=O)O)C=1C=COC=1 ZTXMDOMIWZWWFM-UHFFFAOYSA-N 0.000 claims 1
- FWAHFNXBIAFQBJ-UHFFFAOYSA-N n-[2-[(7-tert-butyl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-1-(oxan-4-yl)ethyl]-n-hydroxyformamide Chemical compound C1C2=CC(C(C)(C)C)=CC=C2CCN1S(=O)(=O)CC(N(O)C=O)C1CCOCC1 FWAHFNXBIAFQBJ-UHFFFAOYSA-N 0.000 claims 1
- AGEKNMCQUWBDOL-UHFFFAOYSA-N n-[3,3-dimethyl-1-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]oct-5-yn-2-yl]-n-hydroxyformamide Chemical compound FC(F)(F)C1=CC=C2CN(S(=O)(=O)CC(C(C)(C)CC#CCC)N(O)C=O)CCC2=C1 AGEKNMCQUWBDOL-UHFFFAOYSA-N 0.000 claims 1
- YEMXWRKCRNHGQG-UHFFFAOYSA-N n-[3,3-dimethyl-1-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]octan-2-yl]-n-hydroxyformamide Chemical compound FC(F)(F)C1=CC=C2CN(S(=O)(=O)CC(C(C)(C)CCCCC)N(O)C=O)CCC2=C1 YEMXWRKCRNHGQG-UHFFFAOYSA-N 0.000 claims 1
- SZBMNJCTMMLJJK-UHFFFAOYSA-N n-[3,3-dimethyl-4-phenyl-1-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]butan-2-yl]-n-hydroxyformamide Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2CN1S(=O)(=O)CC(N(O)C=O)C(C)(C)CC1=CC=CC=C1 SZBMNJCTMMLJJK-UHFFFAOYSA-N 0.000 claims 1
- XFMJFABQTKZYQF-UHFFFAOYSA-N n-[3-ethyl-1-[(6-propan-2-yl-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]pentan-2-yl]-n-hydroxyformamide Chemical compound CC(C)C1=CC=C2CN(S(=O)(=O)CC(C(CC)CC)N(O)C=O)CCC2=C1 XFMJFABQTKZYQF-UHFFFAOYSA-N 0.000 claims 1
- DCDQFXXTNVAMKP-UHFFFAOYSA-N n-[3-ethyl-1-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]pentan-2-yl]-n-hydroxyformamide Chemical compound FC(F)(F)C1=CC=C2CN(S(=O)(=O)CC(C(CC)CC)N(O)C=O)CCC2=C1 DCDQFXXTNVAMKP-UHFFFAOYSA-N 0.000 claims 1
- VCXUXRQJHGECPT-UHFFFAOYSA-N n-[4,4-dimethyl-1-[(7-propoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]pentan-2-yl]-n-hydroxyformamide Chemical compound C1CN(S(=O)(=O)CC(CC(C)(C)C)N(O)C=O)CC2=CC(OCCC)=CC=C21 VCXUXRQJHGECPT-UHFFFAOYSA-N 0.000 claims 1
- GOHHXUFGEIVJGD-UHFFFAOYSA-N n-[4,4-dimethyl-1-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]pentan-2-yl]-n-hydroxyformamide Chemical compound FC(F)(F)C1=CC=C2CN(S(=O)(=O)CC(CC(C)(C)C)N(O)C=O)CCC2=C1 GOHHXUFGEIVJGD-UHFFFAOYSA-N 0.000 claims 1
- VGHDVSAUHFSSJE-HZPDHXFCSA-N n-hydroxy-n-[(1s)-1-[(2r)-oxolan-2-yl]-2-[[7-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]formamide Chemical compound C([C@@H]1[C@@H](CS(=O)(=O)N2CC3=CC(=CC=C3CC2)C(F)(F)F)N(C=O)O)CCO1 VGHDVSAUHFSSJE-HZPDHXFCSA-N 0.000 claims 1
- GCLQHMDMALNENB-OEMAIJDKSA-N n-hydroxy-n-[1-[(2r)-oxolan-2-yl]-2-[[6-(trifluoromethyl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonyl]ethyl]formamide Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2CN1S(=O)(=O)CC(N(C=O)O)[C@H]1CCCO1 GCLQHMDMALNENB-OEMAIJDKSA-N 0.000 claims 1
- JTZBPGSTBZLPTB-UHFFFAOYSA-N n-hydroxy-n-[1-[(7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]-4-(oxolan-2-yl)butan-2-yl]formamide Chemical compound C1C2=CC(OC)=CC=C2CCN1S(=O)(=O)CC(N(O)C=O)CCC1CCCO1 JTZBPGSTBZLPTB-UHFFFAOYSA-N 0.000 claims 1
- NMIVQOXYTAOBTQ-UHFFFAOYSA-N n-hydroxy-n-[4-methyl-1-[(7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl)sulfonyl]pentan-2-yl]formamide Chemical compound C1=C(OC(C)C)C=C2CN(S(=O)(=O)CC(CC(C)C)N(O)C=O)CCC2=C1 NMIVQOXYTAOBTQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- 206010016654 Fibrosis Diseases 0.000 abstract 1
- 206010003246 arthritis Diseases 0.000 abstract 1
- 208000019425 cirrhosis of liver Diseases 0.000 abstract 1
- 230000004761 fibrosis Effects 0.000 abstract 1
- 210000004185 liver Anatomy 0.000 abstract 1
- 208000005069 pulmonary fibrosis Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/4035—Isoindoles, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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Applications Claiming Priority (2)
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EP05110035 | 2005-10-26 | ||
PCT/EP2006/067713 WO2007048788A1 (en) | 2005-10-26 | 2006-10-24 | Sulfonamide derivatives and use thereof for the modulation of metalloproteinases |
Publications (1)
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HRP20110874T1 true HRP20110874T1 (hr) | 2011-12-31 |
Family
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Family Applications (1)
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HR20110874T HRP20110874T1 (hr) | 2005-10-26 | 2011-11-23 | Derivati sulfonamida i njihova uporaba za modulaciju metaloproteinaza |
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EP (1) | EP1951674B1 (xx) |
JP (1) | JP5203956B2 (xx) |
KR (1) | KR20080064880A (xx) |
CN (1) | CN101346353B (xx) |
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ES (1) | ES2372866T3 (xx) |
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SI (1) | SI1951674T1 (xx) |
WO (1) | WO2007048788A1 (xx) |
ZA (1) | ZA200803327B (xx) |
Families Citing this family (20)
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NZ552397A (en) | 2004-07-15 | 2011-04-29 | Amr Technology Inc | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
ES2643161T3 (es) * | 2008-11-11 | 2017-11-21 | Novartis Ag | Formas cristalinas de HCL de fingolimod |
EP2429293B1 (en) | 2009-05-12 | 2014-10-29 | Bristol-Myers Squibb Company | CRYSTALLINE FORMS OF (S)-7-([1,2,4]TRIAZOLO[1,5-a]PYRIDIN-6-YL)-4-(3,4-DICHLOROHPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AND USE THEREOF |
EP2429295B1 (en) | 2009-05-12 | 2013-12-25 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
WO2010132442A1 (en) | 2009-05-12 | 2010-11-18 | Albany Molecular Reserch, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
AU2010260455A1 (en) * | 2009-06-19 | 2012-02-02 | Teva Pharmaceutical Industries Ltd. | Treatment of multiple sclerosis with laquinimod |
EA025468B1 (ru) * | 2009-07-30 | 2016-12-30 | Тева Фармасьютикал Индастриз Лтд. | Лечение болезни крона с применением лаквинимода |
JP5859438B2 (ja) | 2009-08-10 | 2016-02-10 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドを用いたbdnf関連疾患の治療 |
SG10201501535UA (en) * | 2010-03-03 | 2015-04-29 | Teva Pharma | Treatment of lupus nephritis using laquinimod |
JP5819328B2 (ja) * | 2010-03-03 | 2015-11-24 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドとメトトレキセートとの組合せによる関節リウマチの治療 |
PE20130496A1 (es) * | 2010-03-03 | 2013-05-08 | Teva Pharma | Tratamiento de artritis por lupus usando laquinimod |
JP5950428B2 (ja) * | 2010-08-05 | 2016-07-13 | 日東電工株式会社 | 線維化組織から正常組織を再生するための組成物 |
CA2811504C (en) * | 2010-09-17 | 2018-06-05 | Kaken Pharmaceutical Co., Ltd. | Composition for maintaining function of platelets |
CA2851525A1 (en) | 2011-10-12 | 2013-04-18 | Teva Pharmaceutical Industries Ltd. | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
US20140323550A1 (en) * | 2011-11-18 | 2014-10-30 | Nitto Denko Corporation | Intestinal fibrosis treatment agent |
AU2013214909A1 (en) | 2012-02-03 | 2014-09-18 | Teva Pharmaceutical Industries Ltd. | Use of laquinimod for treating Crohn's disease patients who failed first-line anti-TNFa therapy |
TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
CN103102304B (zh) * | 2013-01-19 | 2015-03-11 | 安徽师范大学 | N-磺酰基取代四氢异喹啉衍生物的制备方法 |
AU2023211607A1 (en) * | 2022-01-28 | 2024-08-22 | Opna Bio SA | Compounds and methods for yap/tead modulation and indications therefor |
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GB9919776D0 (en) * | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
DE60033809T2 (de) * | 1999-06-04 | 2007-12-06 | Astrazeneca Ab | Inhibitoren von metalloproteinasen |
WO2001087844A1 (en) * | 2000-05-15 | 2001-11-22 | Darwin Discovery Limited | Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity |
GB0216383D0 (en) * | 2002-07-13 | 2002-08-21 | Astrazeneca Ab | Compounds |
SE0301922D0 (sv) * | 2003-06-27 | 2003-06-27 | Astrazeneca Ab | Novel compounds |
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DK1951674T3 (da) | 2012-01-02 |
CN101346353B (zh) | 2012-01-11 |
CY1112370T1 (el) | 2015-12-09 |
EP1951674B1 (en) | 2011-11-23 |
US20090221575A1 (en) | 2009-09-03 |
RS52229B (en) | 2012-10-31 |
EP1951674A1 (en) | 2008-08-06 |
JP2009513601A (ja) | 2009-04-02 |
WO2007048788A1 (en) | 2007-05-03 |
JP5203956B2 (ja) | 2013-06-05 |
ES2372866T3 (es) | 2012-01-27 |
BRPI0617931A2 (pt) | 2011-08-09 |
CA2623879A1 (en) | 2007-05-03 |
EA013907B1 (ru) | 2010-08-30 |
HK1123304A1 (en) | 2009-06-12 |
ZA200803327B (en) | 2009-09-30 |
AU2006307939A1 (en) | 2007-05-03 |
CA2623879C (en) | 2014-03-25 |
IL190835A (en) | 2013-01-31 |
KR20080064880A (ko) | 2008-07-09 |
ATE534630T1 (de) | 2011-12-15 |
EA200801183A1 (ru) | 2008-10-30 |
PL1951674T3 (pl) | 2012-04-30 |
AU2006307939B2 (en) | 2012-03-29 |
SI1951674T1 (sl) | 2012-01-31 |
CN101346353A (zh) | 2009-01-14 |
US7879876B2 (en) | 2011-02-01 |
PT1951674E (pt) | 2011-12-19 |
IL190835A0 (en) | 2008-11-03 |
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