EA023239B1 - Соединения в качестве ингибиторов диацилглицерин ацилтрансферазы - Google Patents
Соединения в качестве ингибиторов диацилглицерин ацилтрансферазы Download PDFInfo
- Publication number
- EA023239B1 EA023239B1 EA201391724A EA201391724A EA023239B1 EA 023239 B1 EA023239 B1 EA 023239B1 EA 201391724 A EA201391724 A EA 201391724A EA 201391724 A EA201391724 A EA 201391724A EA 023239 B1 EA023239 B1 EA 023239B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- phenyl
- amino
- acetic acid
- oxo
- carbamoyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 305
- 102000002148 Diacylglycerol O-acyltransferase Human genes 0.000 title abstract description 4
- 108010001348 Diacylglycerol O-acyltransferase Proteins 0.000 title abstract description 4
- 239000002404 acyltransferase inhibitor Substances 0.000 title 1
- -1 acyl coenzyme A Chemical compound 0.000 claims abstract description 222
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 208000008589 Obesity Diseases 0.000 claims abstract description 17
- 235000020824 obesity Nutrition 0.000 claims abstract description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 722
- 235000011054 acetic acid Nutrition 0.000 claims description 263
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 197
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 110
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 82
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 73
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000010802 sludge Substances 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 28
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 235000019260 propionic acid Nutrition 0.000 claims description 17
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 17
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 11
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- UALUVYAVLBCJSX-UHFFFAOYSA-N 2-[1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 UALUVYAVLBCJSX-UHFFFAOYSA-N 0.000 claims description 7
- 239000013256 coordination polymer Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- DKUAUHFLWURXHI-UHFFFAOYSA-N 2-[2-methyl-1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 DKUAUHFLWURXHI-UHFFFAOYSA-N 0.000 claims description 6
- AUHZKZVYXYNDKZ-UHFFFAOYSA-N 2-[1-hydroxy-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(O)C(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 AUHZKZVYXYNDKZ-UHFFFAOYSA-N 0.000 claims description 5
- SAKJAQCRZKYULA-UHFFFAOYSA-N 2-[1-oxo-6-[4-(phenylcarbamoylamino)phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(CC(F)(F)F)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 SAKJAQCRZKYULA-UHFFFAOYSA-N 0.000 claims description 5
- CNQKDFXIPQEAPX-UHFFFAOYSA-N 2-[1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydroisoquinolin-2-yl]acetic acid Chemical compound C=1C=C2C(=O)N(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 CNQKDFXIPQEAPX-UHFFFAOYSA-N 0.000 claims description 5
- NGNMLHRBBDNHLP-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 NGNMLHRBBDNHLP-UHFFFAOYSA-N 0.000 claims description 5
- XBHSNOFIXYWDDM-UHFFFAOYSA-N 2-[2-hydroxy-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydro-1h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2CC(CC(=O)O)(O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 XBHSNOFIXYWDDM-UHFFFAOYSA-N 0.000 claims description 5
- GCFDSXAGASLFHR-UHFFFAOYSA-N 2-[2-methoxy-1-oxo-6-[4-(phenylcarbamoylamino)phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(OC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 GCFDSXAGASLFHR-UHFFFAOYSA-N 0.000 claims description 5
- KBWVFPJLQSTUIL-UHFFFAOYSA-N 2-[6-[2-chloro-4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C(=C1)Cl)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 KBWVFPJLQSTUIL-UHFFFAOYSA-N 0.000 claims description 5
- JDLZNLPUKKDOQG-UHFFFAOYSA-N 2-[6-[2-chloro-4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C(=C1)Cl)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 JDLZNLPUKKDOQG-UHFFFAOYSA-N 0.000 claims description 5
- OTKTZEZTFCAULO-UHFFFAOYSA-N 2-[6-[5-[(3,4-difluorophenyl)carbamoylamino]pyrazin-2-yl]-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(CC(F)(F)F)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC=C(F)C(F)=C1 OTKTZEZTFCAULO-UHFFFAOYSA-N 0.000 claims description 5
- LGJLRWLKQDDLTR-UHFFFAOYSA-N 2-[2-(methoxymethyl)-1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(COC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 LGJLRWLKQDDLTR-UHFFFAOYSA-N 0.000 claims description 4
- PVAWMRNDSIIVHE-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[4-(phenylcarbamoylamino)phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 PVAWMRNDSIIVHE-UHFFFAOYSA-N 0.000 claims description 4
- SMMPSMUJHXWKMI-UHFFFAOYSA-N 2-[2-ethyl-3-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-inden-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 SMMPSMUJHXWKMI-UHFFFAOYSA-N 0.000 claims description 4
- PFTRMWGVCRYJIY-UHFFFAOYSA-N 2-[2-hydroxy-1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 PFTRMWGVCRYJIY-UHFFFAOYSA-N 0.000 claims description 4
- CXHMUZQQGKFASI-UHFFFAOYSA-N 2-[6-[4-(phenylcarbamoylamino)phenyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2CC(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 CXHMUZQQGKFASI-UHFFFAOYSA-N 0.000 claims description 4
- UZFDYBISEDYSCF-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-3-fluorophenyl]-2-(hydroxymethyl)-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CO)(CC(O)=O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 UZFDYBISEDYSCF-UHFFFAOYSA-N 0.000 claims description 4
- CRWJBOJJZTWCRV-UHFFFAOYSA-N 3-[1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound C=1C=C2C(=O)C(CCC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 CRWJBOJJZTWCRV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- SUHRJLNXGXGOHI-UHFFFAOYSA-N 2-[1-oxo-6-[4-[[2-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F SUHRJLNXGXGOHI-UHFFFAOYSA-N 0.000 claims description 2
- JRDFRLJGPLFYKQ-UHFFFAOYSA-N 2-[1-oxo-6-[4-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 JRDFRLJGPLFYKQ-UHFFFAOYSA-N 0.000 claims description 2
- FAUOEZXQDNQESE-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[4-[[2-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F FAUOEZXQDNQESE-UHFFFAOYSA-N 0.000 claims description 2
- MPFGNAJAYMCGJJ-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[4-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 MPFGNAJAYMCGJJ-UHFFFAOYSA-N 0.000 claims description 2
- YYCRLBMQMLIHOA-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[5-(phenylcarbamoylamino)pyrazin-2-yl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC=CC=C1 YYCRLBMQMLIHOA-UHFFFAOYSA-N 0.000 claims description 2
- GOOOZNPSYJLFGF-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[5-(phenylcarbamoylamino)pyridin-2-yl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=C1)=CC=C1NC(=O)NC1=CC=CC=C1 GOOOZNPSYJLFGF-UHFFFAOYSA-N 0.000 claims description 2
- XZBKUTVPUYFSKP-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[6-[[3-(trifluoromethyl)phenyl]carbamoylamino]pyridazin-3-yl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=N1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 XZBKUTVPUYFSKP-UHFFFAOYSA-N 0.000 claims description 2
- PEVWITOYSZCNAJ-UHFFFAOYSA-N 2-[2-ethyl-6-[3-fluoro-4-(phenylcarbamoylamino)phenyl]-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC=C1 PEVWITOYSZCNAJ-UHFFFAOYSA-N 0.000 claims description 2
- FPWYJXIPDDSLDW-UHFFFAOYSA-N 2-[2-methyl-1-oxo-6-[5-(phenylcarbamoylamino)pyridin-2-yl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(N=C1)=CC=C1NC(=O)NC1=CC=CC=C1 FPWYJXIPDDSLDW-UHFFFAOYSA-N 0.000 claims description 2
- YHPOUAZQLBFWHY-UHFFFAOYSA-N 2-[2-methyl-1-oxo-6-[5-(phenylcarbamoylamino)pyrimidin-2-yl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(N=C1)=NC=C1NC(=O)NC1=CC=CC=C1 YHPOUAZQLBFWHY-UHFFFAOYSA-N 0.000 claims description 2
- ZOFMQZIBUUJOQK-UHFFFAOYSA-N 2-[3-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1,2-dihydroinden-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 ZOFMQZIBUUJOQK-UHFFFAOYSA-N 0.000 claims description 2
- LLAHSXQFACDLMM-UHFFFAOYSA-N 2-[3-oxo-6-[4-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1,2-dihydroinden-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 LLAHSXQFACDLMM-UHFFFAOYSA-N 0.000 claims description 2
- MIQYTXQVOMDRST-UHFFFAOYSA-N 2-[6-[2-chloro-4-[(3-chlorophenyl)carbamoylamino]phenyl]-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(CC(F)(F)F)CCC2=CC=1C(C(=C1)Cl)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 MIQYTXQVOMDRST-UHFFFAOYSA-N 0.000 claims description 2
- ZPCRUKQDYCMMJO-UHFFFAOYSA-N 2-[6-[2-fluoro-4-(phenylcarbamoylamino)phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C(=C1)F)=CC=C1NC(=O)NC1=CC=CC=C1 ZPCRUKQDYCMMJO-UHFFFAOYSA-N 0.000 claims description 2
- XCXMPJYDLWIOIW-UHFFFAOYSA-N 2-[6-[3-fluoro-4-(phenylcarbamoylamino)phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC=C1 XCXMPJYDLWIOIW-UHFFFAOYSA-N 0.000 claims description 2
- KXKXEAZHESEXLX-UHFFFAOYSA-N 2-[6-[4-[(3,5-dimethylphenyl)carbamoylamino]phenyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetic acid Chemical compound CC1=CC(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCC(CC(O)=O)CC3=CC=2)=C1 KXKXEAZHESEXLX-UHFFFAOYSA-N 0.000 claims description 2
- DQVYPYPMZGYYFY-UHFFFAOYSA-N 2-[6-[4-[(3,5-dimethylphenyl)carbamoylamino]phenyl]-2-methoxy-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(OC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC(C)=CC(C)=C1 DQVYPYPMZGYYFY-UHFFFAOYSA-N 0.000 claims description 2
- XDJXVWDGWRQSIT-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-2,5-difluorophenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical class C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C(=C1)F)=CC(F)=C1NC(=O)NC1=CC=CC(Cl)=C1 XDJXVWDGWRQSIT-UHFFFAOYSA-N 0.000 claims description 2
- AYKTXESUYKIISE-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 AYKTXESUYKIISE-UHFFFAOYSA-N 0.000 claims description 2
- CUFFYZOQFNAEHV-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 CUFFYZOQFNAEHV-UHFFFAOYSA-N 0.000 claims description 2
- NYJBKDQQEBZXNF-UHFFFAOYSA-N 2-[6-[4-[(3-methoxyphenyl)carbamoylamino]phenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound COC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCC(C)(CC(O)=O)C(=O)C3=CC=2)=C1 NYJBKDQQEBZXNF-UHFFFAOYSA-N 0.000 claims description 2
- YZUNJPZMSSNGRD-UHFFFAOYSA-N 2-[6-[4-[(4-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C=2C=C3CCC(CC(O)=O)C(=O)C3=CC=2)C=C1 YZUNJPZMSSNGRD-UHFFFAOYSA-N 0.000 claims description 2
- GCAJWPRCJQPFBU-UHFFFAOYSA-N 2-[6-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2CC(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GCAJWPRCJQPFBU-UHFFFAOYSA-N 0.000 claims description 2
- GMQPWNCRFKWGEB-UHFFFAOYSA-N 2-[6-[5-(cyclohexylcarbamoylamino)pyrazin-2-yl]-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(CC(F)(F)F)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1CCCCC1 GMQPWNCRFKWGEB-UHFFFAOYSA-N 0.000 claims description 2
- GUUQHJVAAUFDBS-UHFFFAOYSA-N 2-[6-[5-[(3,5-dimethylphenyl)carbamoylamino]pyrazin-2-yl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC(C)=CC(C)=C1 GUUQHJVAAUFDBS-UHFFFAOYSA-N 0.000 claims description 2
- INPUQEYVTRHTDO-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyrazin-2-yl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC=CC(Cl)=C1 INPUQEYVTRHTDO-UHFFFAOYSA-N 0.000 claims description 2
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- KSBGWPYFAMSOQV-UHFFFAOYSA-N 3-[6-[4-[(3-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCC(CCC(O)=O)C(=O)C3=CC=2)=C1 KSBGWPYFAMSOQV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
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- RXZAFVHCBIDZJQ-UHFFFAOYSA-N 2-[6-[4-[(4-chlorophenyl)carbamoylamino]phenyl]-2-methoxy-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(OC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 RXZAFVHCBIDZJQ-UHFFFAOYSA-N 0.000 claims 3
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- VDUXYZMUJYVPAW-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-methoxy-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(OC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 VDUXYZMUJYVPAW-UHFFFAOYSA-N 0.000 claims 2
- AIQQVYTXDMUIDX-UHFFFAOYSA-N 2-[1-hydroxy-6-[4-(phenylcarbamoylamino)phenyl]-2-(2,2,2-trifluoroethyl)-3,4-dihydro-1h-naphthalen-2-yl]acetic acid Chemical compound C1=C2CCC(CC(F)(F)F)(CC(O)=O)C(O)C2=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 AIQQVYTXDMUIDX-UHFFFAOYSA-N 0.000 claims 1
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- HONMNFJGBGMBIO-UHFFFAOYSA-N 2-[2-ethyl-1-oxo-6-[6-[[3-(trifluoromethyl)phenyl]carbamoylamino]pyridin-3-yl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=N1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 HONMNFJGBGMBIO-UHFFFAOYSA-N 0.000 claims 1
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- QWNADNIJCPTTMX-UHFFFAOYSA-N 2-[2-methoxy-1-oxo-6-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(OC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 QWNADNIJCPTTMX-UHFFFAOYSA-N 0.000 claims 1
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- RZPJXJRZQCHFBM-UHFFFAOYSA-N 2-[6-[2-chloro-4-[(3-methoxyphenyl)carbamoylamino]phenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C(=C1)Cl)=CC=C1NC(=O)NC1=CC=CC(OC)=C1 RZPJXJRZQCHFBM-UHFFFAOYSA-N 0.000 claims 1
- LOHQOEXTYNDTAV-UHFFFAOYSA-N 2-[6-[2-chloro-4-[(4-chlorophenyl)carbamoylamino]phenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C(=C1)Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 LOHQOEXTYNDTAV-UHFFFAOYSA-N 0.000 claims 1
- DFZSEUXDSOXZQN-UHFFFAOYSA-N 2-[6-[2-chloro-4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C(=C1)Cl)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 DFZSEUXDSOXZQN-UHFFFAOYSA-N 0.000 claims 1
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- YGZKEUGZJSCUPO-UHFFFAOYSA-N 2-[6-[3-fluoro-4-[(3-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=C3CCC(CC(O)=O)C(=O)C3=CC=2)F)=C1 YGZKEUGZJSCUPO-UHFFFAOYSA-N 0.000 claims 1
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- ZZRKKOSPJGNZIY-UHFFFAOYSA-N 2-[6-[4-[(2-fluorophenyl)carbamoylamino]phenyl]-2-hydroxy-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F ZZRKKOSPJGNZIY-UHFFFAOYSA-N 0.000 claims 1
- MBSGOSUKLKAMDW-UHFFFAOYSA-N 2-[6-[4-[(2-methoxy-5-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound COC1=CC=C(C)C=C1NC(=O)NC1=CC=C(C=2C=C3CCC(CC(O)=O)C(=O)C3=CC=2)C=C1 MBSGOSUKLKAMDW-UHFFFAOYSA-N 0.000 claims 1
- YJSRZRDWYZZROJ-UHFFFAOYSA-N 2-[6-[4-[(3,5-dimethylphenyl)carbamoylamino]-3-fluorophenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound CC1=CC(C)=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=C3CCC(CC(O)=O)C(=O)C3=CC=2)F)=C1 YJSRZRDWYZZROJ-UHFFFAOYSA-N 0.000 claims 1
- WAFRQRAIKCYHTO-UHFFFAOYSA-N 2-[6-[4-[(3,5-dimethylphenyl)carbamoylamino]-3-fluorophenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical class C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC(C)=CC(C)=C1 WAFRQRAIKCYHTO-UHFFFAOYSA-N 0.000 claims 1
- PGCIZTOGIVQWAF-UHFFFAOYSA-N 2-[6-[4-[(3,5-dimethylphenyl)carbamoylamino]phenyl]-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound CC1=CC(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCC(CC(O)=O)(CC(F)(F)F)C(=O)C3=CC=2)=C1 PGCIZTOGIVQWAF-UHFFFAOYSA-N 0.000 claims 1
- FBXVQKFUSGPDRC-UHFFFAOYSA-N 2-[6-[4-[(3,5-dimethylphenyl)carbamoylamino]phenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC(C)=CC(C)=C1 FBXVQKFUSGPDRC-UHFFFAOYSA-N 0.000 claims 1
- ATVFUXFGPGVLDU-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-2-fluorophenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C(=C1)F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 ATVFUXFGPGVLDU-UHFFFAOYSA-N 0.000 claims 1
- JHLHDIVKVQTZQV-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-2-methylphenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C(C=2C=C3CCC(C)(CC(O)=O)C(=O)C3=CC=2)C(C)=CC=1NC(=O)NC1=CC=CC(Cl)=C1 JHLHDIVKVQTZQV-UHFFFAOYSA-N 0.000 claims 1
- RSPPZZQAZJAFQJ-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-3-fluorophenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 RSPPZZQAZJAFQJ-UHFFFAOYSA-N 0.000 claims 1
- HDCNICRJZJKNGW-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-3-fluorophenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 HDCNICRJZJKNGW-UHFFFAOYSA-N 0.000 claims 1
- XMPBBLJTZJRWCH-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]-3-fluorophenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 XMPBBLJTZJRWCH-UHFFFAOYSA-N 0.000 claims 1
- YOWRGCUYUFZWTH-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-1-oxo-2-propyl-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CCC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 YOWRGCUYUFZWTH-UHFFFAOYSA-N 0.000 claims 1
- LAXQTSCQSWMNKS-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]-2-methylpropanoic acid Chemical compound C=1C=C2C(=O)C(C(C)(C)C(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 LAXQTSCQSWMNKS-UHFFFAOYSA-N 0.000 claims 1
- UXAYRDNCWJDJDQ-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-(methoxymethyl)-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(COC)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 UXAYRDNCWJDJDQ-UHFFFAOYSA-N 0.000 claims 1
- SCKUUPFDYKIQOE-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-ethyl-3-oxo-1h-inden-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 SCKUUPFDYKIQOE-UHFFFAOYSA-N 0.000 claims 1
- GDEAIUOGQRCFTK-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-fluoro-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(F)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 GDEAIUOGQRCFTK-UHFFFAOYSA-N 0.000 claims 1
- BDNIMUGIXJPXQS-UHFFFAOYSA-N 2-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-2-hydroxy-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 BDNIMUGIXJPXQS-UHFFFAOYSA-N 0.000 claims 1
- YXFWVGCLGFGZML-UHFFFAOYSA-N 2-[6-[4-[(3-cyanophenyl)carbamoylamino]-3-fluorophenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(C#N)=C1 YXFWVGCLGFGZML-UHFFFAOYSA-N 0.000 claims 1
- GQVYWHVTDLQUQS-UHFFFAOYSA-N 2-[6-[4-[(3-fluorophenyl)carbamoylamino]phenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 GQVYWHVTDLQUQS-UHFFFAOYSA-N 0.000 claims 1
- JAWVYUYMTKONOL-UHFFFAOYSA-N 2-[6-[4-[(3-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]acetic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCC(CC(O)=O)C(=O)C3=CC=2)=C1 JAWVYUYMTKONOL-UHFFFAOYSA-N 0.000 claims 1
- KFTXXNPIWHPKEY-UHFFFAOYSA-N 2-[6-[4-[(3-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydroisoquinolin-2-yl]acetic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCN(CC(O)=O)C(=O)C3=CC=2)=C1 KFTXXNPIWHPKEY-UHFFFAOYSA-N 0.000 claims 1
- HKQPJFRLSVKICC-UHFFFAOYSA-N 2-[6-[4-[(3-methylphenyl)carbamoylamino]phenyl]-3-oxo-1,2-dihydroinden-2-yl]acetic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CC(CC(O)=O)C(=O)C3=CC=2)=C1 HKQPJFRLSVKICC-UHFFFAOYSA-N 0.000 claims 1
- WTIDHOOQZUUBJK-UHFFFAOYSA-N 2-[6-[4-[(4-chlorophenyl)carbamoylamino]-2-methylphenyl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C(C=2C=C3CCC(C)(CC(O)=O)C(=O)C3=CC=2)C(C)=CC=1NC(=O)NC1=CC=C(Cl)C=C1 WTIDHOOQZUUBJK-UHFFFAOYSA-N 0.000 claims 1
- AEARCQQPFRJMST-UHFFFAOYSA-N 2-[6-[4-[(4-chlorophenyl)carbamoylamino]-3-fluorophenyl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 AEARCQQPFRJMST-UHFFFAOYSA-N 0.000 claims 1
- VIDDMOYXGCYFMO-UHFFFAOYSA-N 2-[6-[4-[(4-chlorophenyl)carbamoylamino]phenyl]-2-hydroxy-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 VIDDMOYXGCYFMO-UHFFFAOYSA-N 0.000 claims 1
- PSFWQDRSKGYFAF-UHFFFAOYSA-N 2-[6-[4-[[4-fluoro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2CC(CC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 PSFWQDRSKGYFAF-UHFFFAOYSA-N 0.000 claims 1
- KCHONDPMLCCCAN-UHFFFAOYSA-N 2-[6-[5-[(3,5-dimethylphenyl)carbamoylamino]pyridin-2-yl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=C1)=CC=C1NC(=O)NC1=CC(C)=CC(C)=C1 KCHONDPMLCCCAN-UHFFFAOYSA-N 0.000 claims 1
- DJQCXRIJMYGDLW-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyrazin-2-yl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2CC(CC(=O)O)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC=CC(Cl)=C1 DJQCXRIJMYGDLW-UHFFFAOYSA-N 0.000 claims 1
- FRBDTYWKBPROEC-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyrazin-2-yl]-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC(=O)O)(CC(F)(F)F)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC=CC(Cl)=C1 FRBDTYWKBPROEC-UHFFFAOYSA-N 0.000 claims 1
- YRBREPFXGDPFDC-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyrazin-2-yl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=C1)=CN=C1NC(=O)NC1=CC=CC(Cl)=C1 YRBREPFXGDPFDC-UHFFFAOYSA-N 0.000 claims 1
- VPWSANNUPDNRLI-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyridin-2-yl]-1-oxo-2-propyl-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CCC)(CC(O)=O)CCC2=CC=1C(N=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 VPWSANNUPDNRLI-UHFFFAOYSA-N 0.000 claims 1
- PQGNPEFETCCBQD-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyridin-2-yl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 PQGNPEFETCCBQD-UHFFFAOYSA-N 0.000 claims 1
- KMFYIIXOLYVANS-UHFFFAOYSA-N 2-[6-[5-[(3-chlorophenyl)carbamoylamino]pyridin-2-yl]-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(C)(CC(O)=O)CCC2=CC=1C(N=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 KMFYIIXOLYVANS-UHFFFAOYSA-N 0.000 claims 1
- MDNSDJGRMXRPPX-UHFFFAOYSA-N 2-[6-[6-[(3-chlorophenyl)carbamoylamino]pyridazin-3-yl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(N=N1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 MDNSDJGRMXRPPX-UHFFFAOYSA-N 0.000 claims 1
- MQGTVKUXJJWHCL-UHFFFAOYSA-N 2-[6-[6-[(3-chlorophenyl)carbamoylamino]pyridin-3-yl]-2-ethyl-1-oxo-3,4-dihydronaphthalen-2-yl]acetic acid Chemical compound C=1C=C2C(=O)C(CC)(CC(O)=O)CCC2=CC=1C(C=N1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 MQGTVKUXJJWHCL-UHFFFAOYSA-N 0.000 claims 1
- BZVAHHBEYFOWQO-UHFFFAOYSA-N 2-methyl-2-[1-oxo-6-[4-(phenylcarbamoylamino)phenyl]-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound C=1C=C2C(=O)C(C(C)(C)C(O)=O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 BZVAHHBEYFOWQO-UHFFFAOYSA-N 0.000 claims 1
- KFEFSMQSMHUFJK-UHFFFAOYSA-N 3-[1-oxo-6-[4-(phenylcarbamoylamino)phenyl]-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound C=1C=C2C(=O)C(CCC(=O)O)CCC2=CC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 KFEFSMQSMHUFJK-UHFFFAOYSA-N 0.000 claims 1
- YTQNMJJEZWPBTF-UHFFFAOYSA-N 3-[6-[3-fluoro-4-[(3-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound CC1=CC=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=C3CCC(CCC(O)=O)C(=O)C3=CC=2)F)=C1 YTQNMJJEZWPBTF-UHFFFAOYSA-N 0.000 claims 1
- QOOWUARUWPPMRI-UHFFFAOYSA-N 3-[6-[3-fluoro-4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound C=1C=C2C(=O)C(CCC(=O)O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 QOOWUARUWPPMRI-UHFFFAOYSA-N 0.000 claims 1
- LWOCAVRYWXSZCC-UHFFFAOYSA-N 3-[6-[4-[(2-methoxy-5-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound COC1=CC=C(C)C=C1NC(=O)NC1=CC=C(C=2C=C3CCC(CCC(O)=O)C(=O)C3=CC=2)C=C1 LWOCAVRYWXSZCC-UHFFFAOYSA-N 0.000 claims 1
- ZWRDEGDDFJIDDB-UHFFFAOYSA-N 3-[6-[4-[(2-methoxy-5-methylphenyl)carbamoylamino]phenyl]-1-oxo-3,4-dihydroisoquinolin-2-yl]propanoic acid Chemical compound COC1=CC=C(C)C=C1NC(=O)NC1=CC=C(C=2C=C3CCN(CCC(O)=O)C(=O)C3=CC=2)C=C1 ZWRDEGDDFJIDDB-UHFFFAOYSA-N 0.000 claims 1
- LAMFURLXIRNKRK-UHFFFAOYSA-N 3-[6-[4-[(3-chlorophenyl)carbamoylamino]-3-fluorophenyl]-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]propanoic acid Chemical compound C=1C=C2C(=O)C(CCC(=O)O)CCC2=CC=1C(C=C1F)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 LAMFURLXIRNKRK-UHFFFAOYSA-N 0.000 claims 1
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- WXEUEECQCOZKEJ-UHFFFAOYSA-N Cc1cccc(NC(=O)Nc2ncc(cn2)-c2ccc3CC(CC(O)=O)CCc3c2)c1 Chemical compound Cc1cccc(NC(=O)Nc2ncc(cn2)-c2ccc3CC(CC(O)=O)CCc3c2)c1 WXEUEECQCOZKEJ-UHFFFAOYSA-N 0.000 claims 1
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- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
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- 239000000661 sodium alginate Substances 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N sodium azide Substances [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Substances [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1451DE2011 | 2011-05-20 | ||
| US201161495049P | 2011-06-09 | 2011-06-09 | |
| PCT/US2012/038520 WO2012162127A1 (en) | 2011-05-20 | 2012-05-18 | Novel compounds as diacylglycerol acyltransferase inhibitors |
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| EA201391724A1 EA201391724A1 (ru) | 2014-04-30 |
| EA023239B1 true EA023239B1 (ru) | 2016-05-31 |
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| JP (1) | JP5893724B2 (https=) |
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| WO (1) | WO2012162127A1 (https=) |
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| AU2013341115B2 (en) * | 2012-11-09 | 2016-07-14 | Glaxosmithkline Llc | Novel compounds as diacylglycerol acyltransferase inhibitors |
| WO2014081995A1 (en) * | 2012-11-23 | 2014-05-30 | Glaxosmithkline Llc | Novel compounds as diacylglycerol acyltransferase inhibitors |
| WO2022026380A1 (en) * | 2020-07-29 | 2022-02-03 | Board Of Regents, The University Of Texas System | Urea inhibitors of micro-rna |
| CN111747876B (zh) * | 2020-08-03 | 2023-05-26 | 万华化学集团股份有限公司 | 一种氧化角黄素制备虾青素的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070249620A1 (en) * | 2004-07-02 | 2007-10-25 | Hitoshi Kurata | Urea Derivative |
| US20100041590A1 (en) * | 2006-12-21 | 2010-02-18 | Anne Marie Jeanne Bouillot | Compounds |
| WO2011080718A1 (en) * | 2009-12-31 | 2011-07-07 | Piramal Life Sciences Limited | Inhibitors of diacylglycerol acyl transferase |
| US20110245247A1 (en) * | 2010-03-30 | 2011-10-06 | Abbott Gmbh & Co. Kg | Novel small molecule potentiators of metabotropic glutamate receptors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2006045209A (ja) * | 2004-07-02 | 2006-02-16 | Sankyo Co Ltd | ウレア誘導体 |
| KR20080000652A (ko) * | 2005-04-19 | 2008-01-02 | 바이엘 파마슈티칼스 코포레이션 | 아릴 알킬산 유도체 및 그의 용도 |
| EP2402320A1 (en) | 2006-03-31 | 2012-01-04 | Novartis AG | Anorectic agents |
| WO2008099221A1 (en) * | 2007-02-15 | 2008-08-21 | Prosidion Limited | Amide and urea derivatives for the treatment of metabolic diseases |
| JP2008255024A (ja) * | 2007-04-02 | 2008-10-23 | Banyu Pharmaceut Co Ltd | ビアリールアミン誘導体 |
| US8394823B2 (en) * | 2008-04-11 | 2013-03-12 | Bristol-Myers Squibb Company | Triazolopyridine compounds useful as DGAT1 inhibitors |
| CA2790390A1 (en) | 2009-08-28 | 2011-03-03 | Daiichi Sankyo Company, Limited | Novel tetrahydroisoquinoline compounds |
| JP2011088889A (ja) * | 2009-09-24 | 2011-05-06 | Daiichi Sankyo Co Ltd | 新規テトラヒドロイソキノリン誘導体を含有する医薬 |
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- 2012-05-18 US US14/118,913 patent/US9242929B2/en not_active Expired - Fee Related
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- 2012-05-18 PH PH1/2013/502403A patent/PH12013502403A1/en unknown
- 2012-05-18 KR KR1020137033506A patent/KR20140033426A/ko not_active Withdrawn
- 2012-05-18 SG SG2013084603A patent/SG194976A1/en unknown
- 2012-05-18 AU AU2012259042A patent/AU2012259042B2/en not_active Ceased
- 2012-05-18 ES ES12789372T patent/ES2572261T3/es active Active
- 2012-05-18 PE PE2013002520A patent/PE20140618A1/es not_active Application Discontinuation
- 2012-05-18 WO PCT/US2012/038520 patent/WO2012162127A1/en not_active Ceased
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- 2012-05-18 EA EA201391724A patent/EA023239B1/ru not_active IP Right Cessation
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- 2013-12-13 MA MA36565A patent/MA35398B1/fr unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070249620A1 (en) * | 2004-07-02 | 2007-10-25 | Hitoshi Kurata | Urea Derivative |
| US20100041590A1 (en) * | 2006-12-21 | 2010-02-18 | Anne Marie Jeanne Bouillot | Compounds |
| WO2011080718A1 (en) * | 2009-12-31 | 2011-07-07 | Piramal Life Sciences Limited | Inhibitors of diacylglycerol acyl transferase |
| US20110245247A1 (en) * | 2010-03-30 | 2011-10-06 | Abbott Gmbh & Co. Kg | Novel small molecule potentiators of metabotropic glutamate receptors |
Non-Patent Citations (1)
| Title |
|---|
| CURTIN et al. Isoindolinone ureas a novel class of KDR kinase inhibitors. Bioorganic & Medicinal Chemistry Letters 14 (2004) Pgs 4505-4509 entire document * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103687595A (zh) | 2014-03-26 |
| EP2723332A1 (en) | 2014-04-30 |
| US9242929B2 (en) | 2016-01-26 |
| EP2723332B1 (en) | 2016-03-02 |
| ES2572261T3 (es) | 2016-05-31 |
| DOP2013000273A (es) | 2014-04-15 |
| CN103687595B (zh) | 2017-05-24 |
| KR20140033426A (ko) | 2014-03-18 |
| WO2012162127A1 (en) | 2012-11-29 |
| US20150307445A1 (en) | 2015-10-29 |
| PH12013502403A1 (en) | 2018-04-11 |
| CO6811853A2 (es) | 2013-12-16 |
| PE20140618A1 (es) | 2014-06-05 |
| SG194976A1 (en) | 2013-12-30 |
| JP5893724B2 (ja) | 2016-03-23 |
| JP2014525895A (ja) | 2014-10-02 |
| MA35398B1 (fr) | 2014-09-01 |
| CR20130603A (es) | 2014-09-09 |
| CA2836666A1 (en) | 2012-11-29 |
| AU2012259042A1 (en) | 2013-04-18 |
| MX2013013565A (es) | 2014-01-08 |
| ZA201308569B (en) | 2014-07-30 |
| EP2723332A4 (en) | 2014-10-15 |
| IL229487A0 (en) | 2014-01-30 |
| AU2012259042B2 (en) | 2015-06-11 |
| EA201391724A1 (ru) | 2014-04-30 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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