JP2008524250A5 - - Google Patents
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- JP2008524250A5 JP2008524250A5 JP2007546991A JP2007546991A JP2008524250A5 JP 2008524250 A5 JP2008524250 A5 JP 2008524250A5 JP 2007546991 A JP2007546991 A JP 2007546991A JP 2007546991 A JP2007546991 A JP 2007546991A JP 2008524250 A5 JP2008524250 A5 JP 2008524250A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- thiazolo
- chloro
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 chloro, methoxy Chemical group 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- NRAFIAPTASCPOX-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCC1 NRAFIAPTASCPOX-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- CYDIUTPFBMHRED-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[1-(2-pyrrolidin-1-ylethyl)indol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C3C=CN(CCN4CCCC4)C3=CC=1)CC2 CYDIUTPFBMHRED-UHFFFAOYSA-N 0.000 claims 2
- TVEDENRTDWLOMQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(3-pyrrolidin-1-ylpropyl)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1CCCN1CCCC1 TVEDENRTDWLOMQ-UHFFFAOYSA-N 0.000 claims 2
- UAZFWESTBFIFDL-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(3-pyrrolidin-1-ylpropyl)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1CCCN1CCCC1 UAZFWESTBFIFDL-UHFFFAOYSA-N 0.000 claims 2
- KWQLJEOLJXHWIL-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[2-(dimethylamino)ethoxy]-3-methoxyphenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=C(OCCN(C)C)C(OC)=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=C1 KWQLJEOLJXHWIL-UHFFFAOYSA-N 0.000 claims 2
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000005233 alkylalcohol group Chemical group 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- BDJAEZRIGNCQBZ-UHFFFAOYSA-N methylcyclobutane Chemical compound CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- SZCGSOCKWZXXCY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C(=CC(Cl)=CC=2)Cl)=O)=CC=C1OCCN1CCCC1 SZCGSOCKWZXXCY-UHFFFAOYSA-N 0.000 claims 1
- DGCBEZHOLSSEBJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[1-(2-pyrrolidin-1-ylethyl)benzimidazol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C3N=CN(CCN4CCCC4)C3=CC=1)CC2 DGCBEZHOLSSEBJ-UHFFFAOYSA-N 0.000 claims 1
- IGEPVFCJCBWCKR-KRWDZBQOSA-N 2-(4-chlorophenyl)-5-[1-[(3s)-pyrrolidine-3-carbonyl]-2,3-dihydroindol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C3CCN(C3=CC=1)C(=O)[C@@H]1CNCC1)CC2 IGEPVFCJCBWCKR-KRWDZBQOSA-N 0.000 claims 1
- ZZYBGWHYINHNRV-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[1-methyl-3-(2-pyrrolidin-1-ylethyl)indol-6-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C12=CC=C(N3C(C=4SC(=NC=4CC3)C=3C=CC(Cl)=CC=3)=O)C=C2N(C)C=C1CCN1CCCC1 ZZYBGWHYINHNRV-UHFFFAOYSA-N 0.000 claims 1
- IDKQBMBADBCOLZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[2,3-dimethyl-1-(2-pyrrolidin-1-ylethyl)indol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound CC1=C(C)C2=CC(N3C(C=4SC(=NC=4CC3)C=3C=CC(Cl)=CC=3)=O)=CC=C2N1CCN1CCCC1 IDKQBMBADBCOLZ-UHFFFAOYSA-N 0.000 claims 1
- NJTPXAXJMQQREB-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound N=1C2=CC(N3C(C=4SC(=NC=4CC3)C=3C=CC(Cl)=CC=3)=O)=CC=C2OC=1N(C)C1CCN(C)CC1 NJTPXAXJMQQREB-UHFFFAOYSA-N 0.000 claims 1
- BPFBVGGGKIJLGS-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[2-methyl-1-(2-pyrrolidin-1-ylethyl)indol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound CC1=CC2=CC(N3C(C=4SC(=NC=4CC3)C=3C=CC(Cl)=CC=3)=O)=CC=C2N1CCN1CCCC1 BPFBVGGGKIJLGS-UHFFFAOYSA-N 0.000 claims 1
- IAIBUBMMHHAHGC-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-chloro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C(Cl)C(OCCN3CCCC3)=CC=1)CC2 IAIBUBMMHHAHGC-UHFFFAOYSA-N 0.000 claims 1
- DQMBNMCYYGORQP-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-chloro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C(Cl)C(OCCN3CCCC3)=CC=1)C=C2 DQMBNMCYYGORQP-UHFFFAOYSA-N 0.000 claims 1
- WNFFYVCNKSAKHD-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCOCC1 WNFFYVCNKSAKHD-UHFFFAOYSA-N 0.000 claims 1
- VOZPLKROXDWMKC-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-piperidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCCC1 VOZPLKROXDWMKC-UHFFFAOYSA-N 0.000 claims 1
- OLTKJRQUTDMQEN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCC1 OLTKJRQUTDMQEN-UHFFFAOYSA-N 0.000 claims 1
- UHNODELAPSDZMI-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[(3-methylimidazol-4-yl)methoxy]phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCC1=CN=CN1C UHNODELAPSDZMI-UHFFFAOYSA-N 0.000 claims 1
- RBHCOCLWURYQEX-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[2-(2,2,6,6-tetramethylmorpholin-4-yl)ethoxy]phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CC(C)(C)OC(C)(C)C1 RBHCOCLWURYQEX-UHFFFAOYSA-N 0.000 claims 1
- ZXNVSFWPFVIAFF-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[2-(4-piperidin-1-ylpiperidin-1-yl)ethoxy]phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN(CC1)CCC1N1CCCCC1 ZXNVSFWPFVIAFF-UHFFFAOYSA-N 0.000 claims 1
- NZUCXHZUPVYJHQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[2-[methyl(propan-2-yl)amino]ethoxy]phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=C(OCCN(C)C(C)C)C(OC)=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=C1 NZUCXHZUPVYJHQ-UHFFFAOYSA-N 0.000 claims 1
- JNIIIKKUGUGXHU-GOSISDBHSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[[(2r)-morpholin-2-yl]methoxy]phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OC[C@H]1CNCCO1 JNIIIKKUGUGXHU-GOSISDBHSA-N 0.000 claims 1
- IWKYKHVUBJBBQU-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-(2-pyrrolidin-1-ylethyl)-2,3-dihydro-1,4-benzoxazin-7-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C3OCCN(CCN4CCCC4)C3=CC=1)CC2 IWKYKHVUBJBBQU-UHFFFAOYSA-N 0.000 claims 1
- CFGXMGVRHCZTOP-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[2-(2,2-dimethylmorpholin-4-yl)ethoxy]-3-methoxyphenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCOC(C)(C)C1 CFGXMGVRHCZTOP-UHFFFAOYSA-N 0.000 claims 1
- WXJFJGWILLCRME-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[2-(diethylamino)ethoxy]-3-methoxyphenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC=C1N1C(=O)C(SC(=N2)C=3C=CC(Cl)=CC=3)=C2CC1 WXJFJGWILLCRME-UHFFFAOYSA-N 0.000 claims 1
- ZUJHMOJGLZQVRS-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[2-[cyclohexyl(methyl)amino]ethoxy]-3-methoxyphenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN(C)C1CCCCC1 ZUJHMOJGLZQVRS-UHFFFAOYSA-N 0.000 claims 1
- ZOVTYAMQLZVMDU-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[3-(dimethylamino)propoxy]-3-methoxyphenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=C(OCCCN(C)C)C(OC)=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=C1 ZOVTYAMQLZVMDU-UHFFFAOYSA-N 0.000 claims 1
- MFRDDZGIVQDKLU-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-methyl-2-(2-morpholin-4-ylethylamino)quinolin-6-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound N=1C2=CC=C(N3C(C=4SC(=NC=4CC3)C=3C=CC(Cl)=CC=3)=O)C=C2C(C)=CC=1NCCN1CCOCC1 MFRDDZGIVQDKLU-UHFFFAOYSA-N 0.000 claims 1
- NFKRRJUDHXGJOM-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C(OC)C(OCCN3CCCC3)=CC=1)CC2 NFKRRJUDHXGJOM-UHFFFAOYSA-N 0.000 claims 1
- RVQGJWZVRMUDIC-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C(OC)C(OCCN3CCCC3)=CC=1)C=C2 RVQGJWZVRMUDIC-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- JFRFSLWAFTZZCF-UHFFFAOYSA-N 4-[2-[4-[2-(4-chlorophenyl)-4-oxo-[1,3]thiazolo[5,4-c]pyridin-5-yl]-2-methoxyphenoxy]ethyl]morpholin-3-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCOCC1=O JFRFSLWAFTZZCF-UHFFFAOYSA-N 0.000 claims 1
- JYGNQNQOYZNELV-UHFFFAOYSA-N 5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-2-[4-(trifluoromethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=CC=C1OCCN1CCCC1 JYGNQNQOYZNELV-UHFFFAOYSA-N 0.000 claims 1
- DYJPHFUMUVBJBW-UHFFFAOYSA-N 5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-2-[4-(trifluoromethyl)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(=CC=2)C(F)(F)F)=O)=CC=C1OCCN1CCCC1 DYJPHFUMUVBJBW-UHFFFAOYSA-N 0.000 claims 1
- NHGALHMAWAWSQJ-UHFFFAOYSA-N 5-[3-methoxy-4-[(3-methylimidazol-4-yl)methoxy]phenyl]-2-(4-methoxyphenyl)-[1,3]thiazolo[5,4-c]pyridin-4-one;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C(OC)C(OCC=3N(C=NC=3)C)=CC=1)C=C2 NHGALHMAWAWSQJ-UHFFFAOYSA-N 0.000 claims 1
- ZXIUZISEBUGWLI-UHFFFAOYSA-N 5-[3-methoxy-4-[(3-methylimidazol-4-yl)methoxy]phenyl]-2-[4-(trifluoromethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=CC=C1OCC1=CN=CN1C ZXIUZISEBUGWLI-UHFFFAOYSA-N 0.000 claims 1
- QMOGNLWKZOOBLG-UHFFFAOYSA-N 5-[4-[2-(dimethylamino)ethoxy]-3-methoxyphenyl]-2-(4-methoxyphenyl)-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C(OC)C(OCCN(C)C)=CC=1)CC2 QMOGNLWKZOOBLG-UHFFFAOYSA-N 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
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010022714 Intestinal ulcer Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
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| CA2582327A1 (en) | 2004-10-01 | 2006-04-13 | Takao Suzuki | 2-arylcarboxamide-nitrogeneous heterocycle compound |
| CA2639910A1 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| MX2008015662A (es) * | 2006-06-08 | 2009-01-12 | Lilly Co Eli | Nuevos receptores antagonistas de la hormona concentradora de melanina (mch). |
| CN101558075A (zh) * | 2006-12-14 | 2009-10-14 | 伊莱利利公司 | 5-[4-(氮杂环丁烷-3-基氧基)-苯基]-2-苯基-5H-噻唑并[5,4-c]吡啶-4-酮衍生物及其作为MCH受体拮抗剂的用途 |
| US8198307B2 (en) * | 2007-05-11 | 2012-06-12 | Korea Research Institute Of Chemical Technology | Imidazole derivatives having aryl piperidine substituent, method for preparation thereof and pharmaceutical compositions containing same |
| DE102007028925A1 (de) | 2007-06-22 | 2008-12-24 | Saltigo Gmbh | Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden |
| US20090076275A1 (en) * | 2007-09-19 | 2009-03-19 | David Robert Bolin | Diacylglycerol acyltransferase inhibitors |
| WO2010024258A1 (ja) | 2008-08-29 | 2010-03-04 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する縮環アゾール誘導体 |
| KR20120101551A (ko) | 2009-12-18 | 2012-09-13 | 얀센 파마슈티카 엔.브이. | Ｍｇｌｕｒ５ 수용체의 알로스테릭 조절자로서 바이사이클릭 티아졸 |
| CA2782950A1 (en) | 2009-12-18 | 2011-06-23 | Janssen Pharmaceutica Nv | Bicyclic thiazoles as allosteric modulators of mglur5 receptors |
| US8895737B2 (en) | 2010-07-16 | 2014-11-25 | Shashank Shekhar | Process for preparing antiviral compounds |
| BR112013001138A2 (pt) | 2010-07-16 | 2016-07-05 | Abbvie Inc | ligantes de fosfina para reações catalíticas |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| CN102532123B (zh) * | 2010-12-29 | 2016-03-09 | 中国医学科学院药物研究所 | 噻唑-5-甲酰胺化合物、及其制法和药物组合物与用途 |
| WO2012109573A1 (en) * | 2011-02-11 | 2012-08-16 | Purdue Research Foundation | Substituted thiazoles for use as antiviral agents |
| CN104350059B (zh) * | 2012-03-27 | 2016-12-07 | 拜耳知识产权有限责任公司 | 具有除草和杀虫活性的噻唑并吡啶酮 |
| EP2848621A4 (en) * | 2012-05-10 | 2016-06-01 | Takeda Pharmaceutical | AROMATIC RING CONNECTION |
| FI3805233T3 (fi) | 2014-01-13 | 2024-04-17 | Aurigene Oncology Ltd | N-(5-(3-hydroksipyrrolidin-1-yyli)-2-morfolinooksatsolo[4,5-b]pyridin-6-yyli)-2-(2-metylipyridin-4-yyli)okatsoli-karboksamidin (r)- (s)-enantiomeerit irak4-estäjänä syövän hoitoon |
| US20150252022A1 (en) * | 2014-03-10 | 2015-09-10 | Innov17 Llc | Retinoic acid receptor-related orphan receptor modulators and uses thereof |
| US20150252051A1 (en) * | 2014-03-10 | 2015-09-10 | Innov17 Llc | Retinoic acid receptor-related orphan receptor modulators and uses thereof |
| BR112018000624A2 (pt) * | 2015-07-15 | 2018-09-18 | Aurigene Discovery Technologies Limited | compostos de indazol e azaindazol como inibidores de irak-4 |
| NZ746901A (en) * | 2016-03-11 | 2023-06-30 | Ac Immune Sa | Bicyclic compounds for diagnosis and therapy |
| DK3600270T3 (da) | 2017-03-31 | 2023-07-10 | Aurigene Oncology Ltd | Forbindelser og sammensætninger til behandling af hæmatologiske lidelser |
| CA3079628A1 (en) | 2017-10-31 | 2019-05-09 | Curis, Inc. | Compounds and compositions for treating hematological disorders |
| CN109928939A (zh) * | 2019-02-27 | 2019-06-25 | 上海卡洛化学有限公司 | 一种2,2,6,6-四甲基吗啉的制备方法 |
| JP2024513227A (ja) | 2021-04-05 | 2024-03-22 | ハリア・セラピューティクス・インコーポレイテッド | Ｎｅｋ７阻害剤 |
| KR20240004476A (ko) | 2021-04-08 | 2024-01-11 | 쿠리스 인코퍼레이션 | 암 치료를 위한 병용 요법 |
| US20250177382A1 (en) | 2021-04-22 | 2025-06-05 | Halia Therapeutics, Inc. | Nek7 inhibitors |
| CN115403456B (zh) * | 2022-09-22 | 2023-11-17 | 成都大学 | 一种合成爱德万甜中间体3-羟基-4-甲氧基苯丙醛的方法 |
| CN119592965B (zh) * | 2024-12-10 | 2025-09-26 | 西安交通大学 | 一种基于电合成的羟基酮类化合物的制备方法及其制备的羟基酮类化合物 |
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| JPH0867678A (ja) * | 1993-11-10 | 1996-03-12 | Takeda Chem Ind Ltd | 複素環アミド化合物、その製造法および剤 |
| US7229986B2 (en) * | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| JP2002371059A (ja) * | 2000-05-16 | 2002-12-26 | Takeda Chem Ind Ltd | メラニン凝集ホルモン拮抗剤 |
| GB0124627D0 (en) | 2001-10-15 | 2001-12-05 | Smithkline Beecham Plc | Novel compounds |
| SE0202134D0 (sv) * | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Therapeutic agents |
| EP1572637A1 (en) | 2002-12-11 | 2005-09-14 | Eli Lilly And Company | Novel mch receptor antagonists |
| US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| WO2005047293A1 (en) | 2003-11-07 | 2005-05-26 | Neurocrine Biosciences, Inc. | Melanin-concentrating hormone receptor antagonists and compositions and methods related thereto |
| MX2007007226A (es) * | 2004-12-17 | 2007-08-21 | Lilly Co Eli | Antagonistas receptores novedosos de hormona concentradora de melanina (mch). |
| EP1987020B1 (en) | 2006-02-15 | 2012-10-03 | Sanofi | Azacyclyl-substituted aryldihydroisoquinolinones, process for their preparation and their use as medicaments |
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- 2005-12-16 WO PCT/US2005/045866 patent/WO2006066174A1/en not_active Ceased
- 2005-12-16 JP JP2007546991A patent/JP5072602B2/ja not_active Expired - Fee Related
- 2005-12-16 MX MX2007007227A patent/MX2007007227A/es active IP Right Grant
- 2005-12-16 ES ES05854554T patent/ES2333243T3/es not_active Expired - Lifetime
- 2005-12-16 CN CN2005800431124A patent/CN101080411B/zh not_active Expired - Fee Related
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- 2005-12-16 AT AT05854554T patent/ATE446962T1/de not_active IP Right Cessation
- 2005-12-16 BR BRPI0519124-6A patent/BRPI0519124A2/pt not_active IP Right Cessation
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- 2005-12-16 DE DE602005017423T patent/DE602005017423D1/de not_active Expired - Lifetime
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