KR20090035744A - Ｇａｂａ 수용체의 친화력을 갖는 1ｈ-퀴놀린-4-원 화합물,제조방법, 사용방법 및 조성물 - Google Patents
Ｇａｂａ 수용체의 친화력을 갖는 1ｈ-퀴놀린-4-원 화합물,제조방법, 사용방법 및 조성물 Download PDFInfo
- Publication number
- KR20090035744A KR20090035744A KR1020097004628A KR20097004628A KR20090035744A KR 20090035744 A KR20090035744 A KR 20090035744A KR 1020097004628 A KR1020097004628 A KR 1020097004628A KR 20097004628 A KR20097004628 A KR 20097004628A KR 20090035744 A KR20090035744 A KR 20090035744A
- Authority
- KR
- South Korea
- 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.)
- Withdrawn
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- 238000000034 method Methods 0.000 title claims abstract description 43
- -1 1H-Quinoline-4-one compound Chemical class 0.000 title claims description 102
- 238000002360 preparation method Methods 0.000 title description 13
- 239000000203 mixture Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 39
- 230000007958 sleep Effects 0.000 claims abstract description 25
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 24
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims abstract description 19
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 206010022437 insomnia Diseases 0.000 claims abstract description 19
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 18
- 230000036506 anxiety Effects 0.000 claims abstract description 18
- 230000033228 biological regulation Effects 0.000 claims abstract description 13
- 150000004679 hydroxides Chemical class 0.000 claims abstract description 12
- 206010021118 Hypotonia Diseases 0.000 claims abstract description 11
- 206010039897 Sedation Diseases 0.000 claims abstract description 11
- 150000001805 chlorine compounds Chemical class 0.000 claims abstract description 11
- 206010015037 epilepsy Diseases 0.000 claims abstract description 11
- 230000036640 muscle relaxation Effects 0.000 claims abstract description 11
- 208000019116 sleep disease Diseases 0.000 claims abstract description 8
- 241001465754 Metazoa Species 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 230000001939 inductive effect Effects 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 230000036280 sedation Effects 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 4
- 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 description 4
- 206010002091 Anaesthesia Diseases 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 230000037005 anaesthesia Effects 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical group COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 3
- 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 description 3
- HPBPNWPROCLLAA-UHFFFAOYSA-N 2-bromoethanone Chemical compound BrC[C]=O HPBPNWPROCLLAA-UHFFFAOYSA-N 0.000 claims description 3
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 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 description 2
- 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 description 2
- 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 description 2
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims description 2
- TXQDHQBSNAJSHQ-UHFFFAOYSA-N 2,5-dimethyl-2,5-dihydro-1h-pyrrole Chemical compound CC1NC(C)C=C1 TXQDHQBSNAJSHQ-UHFFFAOYSA-N 0.000 claims description 2
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- MEKDMLHYMHHQMO-UHFFFAOYSA-N 2-(5-bromo-4-oxo-3-phenylquinolin-1-yl)-n,n-dipropylacetamide Chemical compound O=C1C2=C(Br)C=CC=C2N(CC(=O)N(CCC)CCC)C=C1C1=CC=CC=C1 MEKDMLHYMHHQMO-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- WCAWMCKNVDFZLK-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1NC(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 WCAWMCKNVDFZLK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- OXRTXNMACXGUQE-UHFFFAOYSA-N 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)-n-pyrimidin-2-ylacetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)NC1=NC=CC=N1 OXRTXNMACXGUQE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83666606P | 2006-08-10 | 2006-08-10 | |
| EP06118720.9 | 2006-08-10 | ||
| US60/836,666 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090035744A true KR20090035744A (ko) | 2009-04-10 |
Family
ID=38779597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097004628A Withdrawn KR20090035744A (ko) | 2006-08-10 | 2007-08-09 | Ｇａｂａ 수용체의 친화력을 갖는 1ｈ-퀴놀린-4-원 화합물,제조방법, 사용방법 및 조성물 |
Country Status (9)
| 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 |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| CA2660421A1 (en) | 2008-02-14 |
| MX2009001478A (es) | 2009-03-31 |
| EP2064185B1 (en) | 2011-06-08 |
| WO2008017710A1 (en) | 2008-02-14 |
| AU2007283570A1 (en) | 2008-02-14 |
| PL2064185T3 (pl) | 2011-11-30 |
| EP2064185A1 (en) | 2009-06-03 |
| JP2010500330A (ja) | 2010-01-07 |
| NO20090971L (no) | 2009-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20090305 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |