JP2010500330A5 - - Google Patents
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- Publication number
- JP2010500330A5 JP2010500330A5 JP2009523299A JP2009523299A JP2010500330A5 JP 2010500330 A5 JP2010500330 A5 JP 2010500330A5 JP 2009523299 A JP2009523299 A JP 2009523299A JP 2009523299 A JP2009523299 A JP 2009523299A JP 2010500330 A5 JP2010500330 A5 JP 2010500330A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- quinolin
- oxo
- acetamide
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 60
- -1 5-methyl-2-furyl Chemical group 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 239000003795 chemical substances by application Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000002971 oxazolyl group Chemical group 0.000 claims 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 230000001939 inductive effect Effects 0.000 claims 5
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- 206010021118 Hypotonia Diseases 0.000 claims 4
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 4
- 230000036506 anxiety Effects 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 206010015037 epilepsy Diseases 0.000 claims 4
- 206010022437 insomnia Diseases 0.000 claims 4
- 230000036640 muscle relaxation Effects 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims 3
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 2
- BOGNZHRLPQGMID-UHFFFAOYSA-N 1-[2-(3,6-dihydro-2h-pyridin-1-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCC=CC1 BOGNZHRLPQGMID-UHFFFAOYSA-N 0.000 claims 2
- RZUTZNLVXOASCC-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetic acid Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(O)=O)C=C2C1=CC=CC=C1 RZUTZNLVXOASCC-UHFFFAOYSA-N 0.000 claims 2
- HPBPNWPROCLLAA-UHFFFAOYSA-N 2-bromoethanone Chemical compound BrC[C]=O HPBPNWPROCLLAA-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- LUYNJGULZWSSRR-UHFFFAOYSA-N 5-methyl-1-(2-oxo-2-pyrrolidin-1-ylethyl)-2-phenylquinolin-4-one Chemical compound C=1C=CC=CC=1C1=CC(=O)C=2C(C)=CC=CC=2N1CC(=O)N1CCCC1 LUYNJGULZWSSRR-UHFFFAOYSA-N 0.000 claims 2
- QDPOTMAVZCHLCV-UHFFFAOYSA-N 7-bromo-1-(2-oxo-2-piperidin-1-ylethyl)-3-phenylquinolin-4-one Chemical compound C=1C(Br)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCCCC1 QDPOTMAVZCHLCV-UHFFFAOYSA-N 0.000 claims 2
- 206010002091 Anaesthesia Diseases 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 206010039897 Sedation Diseases 0.000 claims 2
- 230000037005 anaesthesia Effects 0.000 claims 2
- 230000003444 anaesthetic effect Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 230000004799 sedative–hypnotic effect Effects 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- JXOSVPFKMYZOBP-UHFFFAOYSA-N 1-[2-(2,4-dimethyl-1,3-oxazol-5-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound O1C(C)=NC(C)=C1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 JXOSVPFKMYZOBP-UHFFFAOYSA-N 0.000 claims 1
- DWPCRBFCOANPFX-UHFFFAOYSA-N 1-[2-(2,5-dimethyl-2,5-dihydropyrrol-1-yl)-2-oxoethyl]-3-(4-methoxyphenyl)-7-methylquinolin-4-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)N1C(C)C=CC1C DWPCRBFCOANPFX-UHFFFAOYSA-N 0.000 claims 1
- CZEXJJNXGJUPOG-UHFFFAOYSA-N 1-[2-(2,5-dimethyl-2,5-dihydropyrrol-1-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound CC1C=CC(C)N1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 CZEXJJNXGJUPOG-UHFFFAOYSA-N 0.000 claims 1
- MHZQEEGUXIJDEC-UHFFFAOYSA-N 1-[2-(2,6-dimethylmorpholin-4-yl)-2-oxoethyl]-3-(4-methoxyphenyl)-7-methylquinolin-4-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)N1CC(C)OC(C)C1 MHZQEEGUXIJDEC-UHFFFAOYSA-N 0.000 claims 1
- PNMGWCBEGYKAEV-UHFFFAOYSA-N 1-[2-(2,6-dimethylmorpholin-4-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound C1C(C)OC(C)CN1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 PNMGWCBEGYKAEV-UHFFFAOYSA-N 0.000 claims 1
- FDLQPRVNOGEUQA-UHFFFAOYSA-N 1-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-3-(4-methoxyphenyl)-7-methylquinolin-4-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)N1CC(C)CC(C)C1 FDLQPRVNOGEUQA-UHFFFAOYSA-N 0.000 claims 1
- JWKMGCLOPNCMJO-UHFFFAOYSA-N 1-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound C1C(C)CC(C)CN1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 JWKMGCLOPNCMJO-UHFFFAOYSA-N 0.000 claims 1
- ZMAPOQKBKSVOIU-UHFFFAOYSA-N 1-[2-(4-acetylpiperazin-1-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound C1CN(C(=O)C)CCN1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 ZMAPOQKBKSVOIU-UHFFFAOYSA-N 0.000 claims 1
- FWPPKEBPCTXWCE-UHFFFAOYSA-N 1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-3-(4-methoxyphenyl)-7-methylquinolin-4-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)N1CCC(O)CC1 FWPPKEBPCTXWCE-UHFFFAOYSA-N 0.000 claims 1
- MZBHXISGRDJTJL-UHFFFAOYSA-N 1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-7-methyl-3-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCC(O)CC1 MZBHXISGRDJTJL-UHFFFAOYSA-N 0.000 claims 1
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims 1
- TXQDHQBSNAJSHQ-UHFFFAOYSA-N 2,5-dimethyl-2,5-dihydro-1h-pyrrole Chemical compound CC1NC(C)C=C1 TXQDHQBSNAJSHQ-UHFFFAOYSA-N 0.000 claims 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims 1
- XIGLAJYWKFSEQK-UHFFFAOYSA-N 2-(4-oxo-3,5-diphenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound O=C1C2=C(C=3C=CC=CC=3)C=CC=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=CC=C1 XIGLAJYWKFSEQK-UHFFFAOYSA-N 0.000 claims 1
- DBMOUAXPUBTGFR-UHFFFAOYSA-N 2-(4-oxo-3,7-diphenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound O=C1C2=CC=C(C=3C=CC=CC=3)C=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=CC=C1 DBMOUAXPUBTGFR-UHFFFAOYSA-N 0.000 claims 1
- LGKBIVRTMDBONU-UHFFFAOYSA-N 2-(4-oxo-3-phenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound O=C1C2=CC=CC=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=CC=C1 LGKBIVRTMDBONU-UHFFFAOYSA-N 0.000 claims 1
- RTRYWMRMNLVDIQ-UHFFFAOYSA-N 2-(5-methyl-4-oxo-2-phenylquinolin-1-yl)-n,n-di(propan-2-yl)acetamide Chemical compound C=1C(=O)C2=C(C)C=CC=C2N(CC(=O)N(C(C)C)C(C)C)C=1C1=CC=CC=C1 RTRYWMRMNLVDIQ-UHFFFAOYSA-N 0.000 claims 1
- ARDWULOUZZPLML-UHFFFAOYSA-N 2-(5-methyl-4-oxo-3-phenylquinolin-1-yl)acetic acid Chemical compound O=C1C=2C(C)=CC=CC=2N(CC(O)=O)C=C1C1=CC=CC=C1 ARDWULOUZZPLML-UHFFFAOYSA-N 0.000 claims 1
- MMSRVNKFSOFZFQ-UHFFFAOYSA-N 2-(7-bromo-4-oxo-3-phenylquinolin-1-yl)-n,n-dibutylacetamide Chemical compound O=C1C2=CC=C(Br)C=C2N(CC(=O)N(CCCC)CCCC)C=C1C1=CC=CC=C1 MMSRVNKFSOFZFQ-UHFFFAOYSA-N 0.000 claims 1
- GOAXNKURYJECIU-UHFFFAOYSA-N 2-(7-bromo-4-oxo-3-phenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound O=C1C2=CC=C(Br)C=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=CC=C1 GOAXNKURYJECIU-UHFFFAOYSA-N 0.000 claims 1
- NGLGSWSXUGMPRV-UHFFFAOYSA-N 2-(7-bromo-4-oxo-3-phenylquinolin-1-yl)-n-(cyclopropylmethyl)-n-propylacetamide Chemical compound C1=C(C=2C=CC=CC=2)C(=O)C2=CC=C(Br)C=C2N1CC(=O)N(CCC)CC1CC1 NGLGSWSXUGMPRV-UHFFFAOYSA-N 0.000 claims 1
- AQTZKLCZSOBXOS-UHFFFAOYSA-N 2-(7-bromo-4-oxo-3-phenylquinolin-1-yl)acetic acid Chemical compound O=C1C2=CC=C(Br)C=C2N(CC(=O)O)C=C1C1=CC=CC=C1 AQTZKLCZSOBXOS-UHFFFAOYSA-N 0.000 claims 1
- BVJOBFGDATYWPY-UHFFFAOYSA-N 2-(7-bromo-4-oxo-3-phenylquinolin-1-yl)acetohydrazide Chemical compound O=C1C2=CC=C(Br)C=C2N(CC(=O)NN)C=C1C1=CC=CC=C1 BVJOBFGDATYWPY-UHFFFAOYSA-N 0.000 claims 1
- BDPNGUFXSYYCJV-UHFFFAOYSA-N 2-(7-methyl-4-oxo-2-phenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound C=1C(=O)C2=CC=C(C)C=C2N(CC(=O)N(CCC)CCC)C=1C1=CC=CC=C1 BDPNGUFXSYYCJV-UHFFFAOYSA-N 0.000 claims 1
- SXFIFHQVBWRGGO-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n,n-di(propan-2-yl)acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(C(C)C)C(C)C)C=C1C1=CC=CC=C1 SXFIFHQVBWRGGO-UHFFFAOYSA-N 0.000 claims 1
- DDAWCJWRQYMAJP-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=CC=C1 DDAWCJWRQYMAJP-UHFFFAOYSA-N 0.000 claims 1
- YRGDSQGPTOYZLC-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(1,2-oxazol-3-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC=1C=CON=1 YRGDSQGPTOYZLC-UHFFFAOYSA-N 0.000 claims 1
- VYNQGWBNHGHGKE-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(1,3,4-thiadiazol-2-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=NN=CS1 VYNQGWBNHGHGKE-UHFFFAOYSA-N 0.000 claims 1
- OALVOWIDIXOGTP-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(1,3-thiazol-2-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=NC=CS1 OALVOWIDIXOGTP-UHFFFAOYSA-N 0.000 claims 1
- HMSJHELQSJRRTQ-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(1-methylpyrazol-3-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC=1C=CN(C)N=1 HMSJHELQSJRRTQ-UHFFFAOYSA-N 0.000 claims 1
- XHSFMRGBANQHQC-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(1h-pyrazol-5-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC=1C=CNN=1 XHSFMRGBANQHQC-UHFFFAOYSA-N 0.000 claims 1
- KNHOLVFOTTUYSC-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(2-methylpyrazol-3-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=CC=NN1C KNHOLVFOTTUYSC-UHFFFAOYSA-N 0.000 claims 1
- OLNJHMJSZJXYLM-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(2-thiophen-2-ylethyl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NCCC1=CC=CS1 OLNJHMJSZJXYLM-UHFFFAOYSA-N 0.000 claims 1
- ZCQQTLBLHWJTQP-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(4-methyl-1,3-thiazol-2-yl)acetamide Chemical compound CC1=CSC(NC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC=CC=3)=C2)=N1 ZCQQTLBLHWJTQP-UHFFFAOYSA-N 0.000 claims 1
- DFVPHBSQSOSHRF-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)acetamide Chemical compound N1N=C(C)C=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 DFVPHBSQSOSHRF-UHFFFAOYSA-N 0.000 claims 1
- QVOMRFDCPQJTGG-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(5-methylpyridin-2-yl)acetamide Chemical compound N1=CC(C)=CC=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 QVOMRFDCPQJTGG-UHFFFAOYSA-N 0.000 claims 1
- QSDNBQWGDHSLKZ-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(5-nitro-1,3-thiazol-2-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=NC=C([N+]([O-])=O)S1 QSDNBQWGDHSLKZ-UHFFFAOYSA-N 0.000 claims 1
- MWWRMEUVBSSQAE-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(pyridin-2-ylmethyl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NCC1=CC=CC=N1 MWWRMEUVBSSQAE-UHFFFAOYSA-N 0.000 claims 1
- YTLZGGFLAQTMCF-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-[(3-methylthiophen-2-yl)methyl]acetamide Chemical compound C1=CSC(CNC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC=CC=3)=C2)=C1C YTLZGGFLAQTMCF-UHFFFAOYSA-N 0.000 claims 1
- WMCFYAYGWIJCQP-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=CC=C(C(F)(F)F)C=C1 WMCFYAYGWIJCQP-UHFFFAOYSA-N 0.000 claims 1
- JEKYVJSEMUINES-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=NN=C(C(F)(F)F)S1 JEKYVJSEMUINES-UHFFFAOYSA-N 0.000 claims 1
- UMAOZLYPGMMJCA-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-quinolin-2-ylacetamide Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(=O)NC=1N=C3C=CC=CC3=CC=1)C=C2C1=CC=CC=C1 UMAOZLYPGMMJCA-UHFFFAOYSA-N 0.000 claims 1
- MJMPVGJAOZQSNN-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n,n-dipropylacetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=C(Cl)C=C1 MJMPVGJAOZQSNN-UHFFFAOYSA-N 0.000 claims 1
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- ACVDOJNTYNQSDC-UHFFFAOYSA-N n,n-dibutyl-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCCC)CCCC)C=C1C1=CC=CC=C1 ACVDOJNTYNQSDC-UHFFFAOYSA-N 0.000 claims 1
- CZNAMKGCKYBELS-UHFFFAOYSA-N n,n-diethyl-2-(5-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=C(C)C=CC=C2N(CC(=O)N(CC)CC)C=C1C1=CC=CC=C1 CZNAMKGCKYBELS-UHFFFAOYSA-N 0.000 claims 1
- PDFBHGMEVMFIOR-UHFFFAOYSA-N n,n-diethyl-2-(7-methyl-4-oxo-2-phenylquinolin-1-yl)acetamide Chemical compound C=1C(=O)C2=CC=C(C)C=C2N(CC(=O)N(CC)CC)C=1C1=CC=CC=C1 PDFBHGMEVMFIOR-UHFFFAOYSA-N 0.000 claims 1
- KCEJJNDCJWSUNA-UHFFFAOYSA-N n,n-diethyl-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CC)CC)C=C1C1=CC=CC=C1 KCEJJNDCJWSUNA-UHFFFAOYSA-N 0.000 claims 1
- UJRNWKCRKKYPMX-UHFFFAOYSA-N n,n-diethyl-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CC)CC)C=C1C1=CC=C(OC)C=C1 UJRNWKCRKKYPMX-UHFFFAOYSA-N 0.000 claims 1
- KKFNHGZGUAMGMK-UHFFFAOYSA-N n,n-dihexyl-2-(5-methyl-4-oxo-2-phenylquinolin-1-yl)acetamide Chemical compound C=1C(=O)C2=C(C)C=CC=C2N(CC(=O)N(CCCCCC)CCCCCC)C=1C1=CC=CC=C1 KKFNHGZGUAMGMK-UHFFFAOYSA-N 0.000 claims 1
- DUJYMHPCOCBCSB-UHFFFAOYSA-N n,n-dihexyl-2-(5-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=C(C)C=CC=C2N(CC(=O)N(CCCCCC)CCCCCC)C=C1C1=CC=CC=C1 DUJYMHPCOCBCSB-UHFFFAOYSA-N 0.000 claims 1
- KCAOSGKYEOUYGZ-UHFFFAOYSA-N n,n-dihexyl-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCCCCC)CCCCCC)C=C1C1=CC=CC=C1 KCAOSGKYEOUYGZ-UHFFFAOYSA-N 0.000 claims 1
- YFVKMPMJKCZGTG-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(=O)NC1CC3=CC=CC=C3C1)C=C2C1=CC=CC=C1 YFVKMPMJKCZGTG-UHFFFAOYSA-N 0.000 claims 1
- MYIIFINZHKWJLM-UHFFFAOYSA-N n-(2,5-dimethylpyrazol-3-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound CN1N=C(C)C=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 MYIIFINZHKWJLM-UHFFFAOYSA-N 0.000 claims 1
- LBHGUCOFHMXLPV-UHFFFAOYSA-N n-(2,5-dimethylpyrazol-3-yl)-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=CC(C)=NN1C LBHGUCOFHMXLPV-UHFFFAOYSA-N 0.000 claims 1
- SMGJWJPJLQPJSO-UHFFFAOYSA-N n-(2-acetylthiophen-3-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound S1C=CC(NC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC=CC=3)=C2)=C1C(=O)C SMGJWJPJLQPJSO-UHFFFAOYSA-N 0.000 claims 1
- FTWYGTTUSJPMMB-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-(5-methyl-4-oxo-3-phenylquinolin-1-yl)-n-propylacetamide Chemical compound O=C1C2=C(C)C=CC=C2N(CC(=O)N(CCO)CCC)C=C1C1=CC=CC=C1 FTWYGTTUSJPMMB-UHFFFAOYSA-N 0.000 claims 1
- JPKLYWBUYJDMDQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-propylacetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCO)CCC)C=C1C1=CC=CC=C1 JPKLYWBUYJDMDQ-UHFFFAOYSA-N 0.000 claims 1
- AQUHWLGRVWWLMR-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-propylacetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCO)CCC)C=C1C1=CC=C(OC)C=C1 AQUHWLGRVWWLMR-UHFFFAOYSA-N 0.000 claims 1
- JYEQRJJPGYMOEV-UHFFFAOYSA-N n-(2-methyl-1h-indol-5-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(=O)CN(C1=CC(C)=CC=C1C1=O)C=C1C1=CC=CC=C1 JYEQRJJPGYMOEV-UHFFFAOYSA-N 0.000 claims 1
- VXEPIUDSHADBHC-UHFFFAOYSA-N n-(3,5-dimethyl-1,2-oxazol-4-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound CC1=NOC(C)=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 VXEPIUDSHADBHC-UHFFFAOYSA-N 0.000 claims 1
- DINSLLXMCNSREB-UHFFFAOYSA-N n-(3-methyl-1,2-oxazol-5-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O1N=C(C)C=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 DINSLLXMCNSREB-UHFFFAOYSA-N 0.000 claims 1
- JRPZIWAVLLAVAW-UHFFFAOYSA-N n-(4-fluorophenyl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=CC=C(F)C=C1 JRPZIWAVLLAVAW-UHFFFAOYSA-N 0.000 claims 1
- KQIGTFJXHNGLQP-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 KQIGTFJXHNGLQP-UHFFFAOYSA-N 0.000 claims 1
- BNEIJBCSFWZTCS-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC(OC)=CC=2)=C1 BNEIJBCSFWZTCS-UHFFFAOYSA-N 0.000 claims 1
- BRDOEBNHCOYPOL-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC(NN=1)=CC=1C1CC1 BRDOEBNHCOYPOL-UHFFFAOYSA-N 0.000 claims 1
- KAUIMWSTMVGUOW-UHFFFAOYSA-N n-(6-methoxypyrimidin-4-yl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C1=NC(OC)=CC(NC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC=CC=3)=C2)=N1 KAUIMWSTMVGUOW-UHFFFAOYSA-N 0.000 claims 1
- JMGZTJTVGCBPKY-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-propylacetamide Chemical compound C1=C(C=2C=CC=CC=2)C(=O)C2=CC=C(C)C=C2N1CC(=O)N(CCC)CC1CC1 JMGZTJTVGCBPKY-UHFFFAOYSA-N 0.000 claims 1
- RNFCTWYNMGPQFR-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-propylacetamide Chemical compound C1=C(C=2C=CC(OC)=CC=2)C(=O)C2=CC=C(C)C=C2N1CC(=O)N(CCC)CC1CC1 RNFCTWYNMGPQFR-UHFFFAOYSA-N 0.000 claims 1
- GLSCZVDTSHNUPQ-UHFFFAOYSA-N n-(furan-2-ylmethyl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NCC1=CC=CO1 GLSCZVDTSHNUPQ-UHFFFAOYSA-N 0.000 claims 1
- MIUHYWIXBDYZKZ-UHFFFAOYSA-N n-[4-(dimethylamino)phenyl]-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 MIUHYWIXBDYZKZ-UHFFFAOYSA-N 0.000 claims 1
- HYQHTRHNVQYEKS-UHFFFAOYSA-N n-ethyl-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(1,3,4-thiadiazol-2-yl)acetamide Chemical compound N=1N=CSC=1N(CC)C(=O)CN(C1=CC(C)=CC=C1C1=O)C=C1C1=CC=CC=C1 HYQHTRHNVQYEKS-UHFFFAOYSA-N 0.000 claims 1
- ZFMRQLOKWHSSKK-UHFFFAOYSA-N n-ethyl-n-(2-hydroxyethyl)-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCO)CC)C=C1C1=CC=CC=C1 ZFMRQLOKWHSSKK-UHFFFAOYSA-N 0.000 claims 1
- LPYQSYNQQPWIOK-UHFFFAOYSA-N n-ethyl-n-(2-hydroxyethyl)-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetamide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(CCO)CC)C=C1C1=CC=C(OC)C=C1 LPYQSYNQQPWIOK-UHFFFAOYSA-N 0.000 claims 1
- XZSRYXBQSINTDT-UHFFFAOYSA-N n-isoquinolin-3-yl-2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(=O)NC=1N=CC3=CC=CC=C3C=1)C=C2C1=CC=CC=C1 XZSRYXBQSINTDT-UHFFFAOYSA-N 0.000 claims 1
- YCDWUKHRCMVHGA-UHFFFAOYSA-N n-methyl-2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]acetohydrazide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(N)C)C=C1C1=CC=C(C)C=C1 YCDWUKHRCMVHGA-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 1
- 230000036280 sedation Effects 0.000 claims 1
- 0 *C(CN(C(*)=C1*)c2cc(*)cc(*)c2C1=O)=O Chemical compound *C(CN(C(*)=C1*)c2cc(*)cc(*)c2C1=O)=O 0.000 description 2
Applications Claiming Priority (3)
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| US83666606P | 2006-08-10 | 2006-08-10 | |
| EP06118720A EP1886996A1 (en) | 2006-08-10 | 2006-08-10 | 1H-Quinolin-4-one compounds, with affinity for the GABA receptor, processes, uses and compositions |
| PCT/EP2007/058288 WO2008017710A1 (en) | 2006-08-10 | 2007-08-09 | 1h-quinolin-4-one compounds, with affinity for the gaba receptor, processes, uses and compositions |
Publications (2)
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| JP2010500330A JP2010500330A (ja) | 2010-01-07 |
| JP2010500330A5 true JP2010500330A5 (enExample) | 2010-07-29 |
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| JP2009523299A Pending JP2010500330A (ja) | 2006-08-10 | 2007-08-09 | Ｇａｂａａ受容体に対して親和性を有する１ｈ−キノリン−４−オン化合物、方法、使用及び組成物 |
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| Country | Link |
|---|---|
| EP (1) | EP2064185B1 (enExample) |
| JP (1) | JP2010500330A (enExample) |
| KR (1) | KR20090035744A (enExample) |
| AU (1) | AU2007283570A1 (enExample) |
| CA (1) | CA2660421A1 (enExample) |
| MX (1) | MX2009001478A (enExample) |
| NO (1) | NO20090971L (enExample) |
| PL (1) | PL2064185T3 (enExample) |
| WO (1) | WO2008017710A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010053127A1 (ja) * | 2008-11-05 | 2010-05-14 | 協和発酵キリン株式会社 | α1GABAA受容体またはα5GABAA受容体の調整剤 |
| ES2846833T3 (es) | 2016-07-18 | 2021-07-29 | Janssen Pharmaceutica Nv | Ligandos de obtención de imágenes de tau por PET |
| EP3562821B9 (en) | 2016-12-28 | 2021-05-26 | Minoryx Therapeutics S.L. | Isoquinoline compounds, methods for their preparation, and therapeutic uses thereof in conditions associated with the alteration of the activity of beta galactosidase |
| DK4426434T3 (da) | 2021-11-02 | 2025-11-10 | Flare Therapeutics Inc | Pparg inverse agonists and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2728900B1 (fr) * | 1994-12-29 | 1997-01-31 | Synthelabo | Derives de 3-phenylisoquinolein-1(2h)-one, leur preparation et leur application en therapeutique |
| GB9621757D0 (en) * | 1996-10-18 | 1996-12-11 | Ciba Geigy Ag | Phenyl-substituted bicyclic heterocyclyl derivatives and their use |
| FR2813791B1 (fr) * | 2000-09-14 | 2004-03-12 | Lafon Labor | Utilisation de 2- et 4-quinolones pour inhiber la neo-proliferation intimale |
| CA2484308A1 (en) * | 2002-05-14 | 2003-11-27 | The Regents Of The University Of California | Substituted quinolone carboxylic acids, their derivatives, site of action, and uses thereof |
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2007
- 2007-08-09 KR KR1020097004628A patent/KR20090035744A/ko not_active Withdrawn
- 2007-08-09 CA CA002660421A patent/CA2660421A1/en not_active Abandoned
- 2007-08-09 WO PCT/EP2007/058288 patent/WO2008017710A1/en not_active Ceased
- 2007-08-09 PL PL07788348T patent/PL2064185T3/pl unknown
- 2007-08-09 JP JP2009523299A patent/JP2010500330A/ja active Pending
- 2007-08-09 MX MX2009001478A patent/MX2009001478A/es active IP Right Grant
- 2007-08-09 AU AU2007283570A patent/AU2007283570A1/en not_active Abandoned
- 2007-08-09 EP EP07788348A patent/EP2064185B1/en not_active Not-in-force
-
2009
- 2009-03-03 NO NO20090971A patent/NO20090971L/no not_active Application Discontinuation
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