JP2010500330A - 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 - Google Patents
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 Download PDFInfo
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- JP2010500330A JP2010500330A JP2009523299A JP2009523299A JP2010500330A JP 2010500330 A JP2010500330 A JP 2010500330A JP 2009523299 A JP2009523299 A JP 2009523299A JP 2009523299 A JP2009523299 A JP 2009523299A JP 2010500330 A JP2010500330 A JP 2010500330A
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- Prior art keywords
- methyl
- phenyl
- quinolin
- oxo
- acetamide
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- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 46
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical class C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 title description 21
- 102000027484 GABAA receptors Human genes 0.000 title 1
- 108091008681 GABAA receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 43
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims abstract description 21
- 206010022437 insomnia Diseases 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 206010039897 Sedation Diseases 0.000 claims abstract description 17
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 15
- 230000036506 anxiety Effects 0.000 claims abstract description 15
- 230000007958 sleep Effects 0.000 claims abstract description 14
- 206010015037 epilepsy Diseases 0.000 claims abstract description 11
- 208000019116 sleep disease Diseases 0.000 claims abstract description 11
- 206010021118 Hypotonia Diseases 0.000 claims abstract description 10
- 230000036640 muscle relaxation Effects 0.000 claims abstract description 10
- 206010002091 Anaesthesia Diseases 0.000 claims abstract description 9
- 230000037005 anaesthesia Effects 0.000 claims abstract description 9
- 150000004677 hydrates Chemical class 0.000 claims abstract description 6
- -1 methoxy, ethoxy Chemical group 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 241000124008 Mammalia Species 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
- 230000001939 inductive effect Effects 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000000147 hypnotic effect Effects 0.000 claims description 8
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 230000036280 sedation Effects 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 4
- 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 4
- 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 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 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
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 230000008569 process Effects 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
- HPBPNWPROCLLAA-UHFFFAOYSA-N 2-bromoethanone Chemical compound BrC[C]=O HPBPNWPROCLLAA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 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
- 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 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
- 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
- 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 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
- 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
- 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 description 2
- 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 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
- 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 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
- 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 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
- 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 description 2
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- NNFQNNWEKKIWIT-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-thiophen-2-ylethyl)-3-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)C1=CC=CS1 NNFQNNWEKKIWIT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- JNVLJPZHGCZLDC-UHFFFAOYSA-N ethyl 2-(7-methyl-4-oxo-2-phenylquinolin-1-yl)acetate Chemical compound C=1C(=O)C2=CC=C(C)C=C2N(CC(=O)OCC)C=1C1=CC=CC=C1 JNVLJPZHGCZLDC-UHFFFAOYSA-N 0.000 claims description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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- 239000003921 oil Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 238000011458 pharmacological treatment Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 229960004559 theobromine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229960000820 zopiclone Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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)
| Publication Number | Publication Date |
|---|---|
| JP2010500330A true JP2010500330A (ja) | 2010-01-07 |
| JP2010500330A5 JP2010500330A5 (enExample) | 2010-07-29 |
Family
ID=38779597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
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 |
| KR20090035744A (ko) | 2009-04-10 |
| PL2064185T3 (pl) | 2011-11-30 |
| EP2064185A1 (en) | 2009-06-03 |
| NO20090971L (no) | 2009-04-30 |
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