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
- Publication number
- 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
- 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
Links
- 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
- 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 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
- 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
- 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 description 2
- HGBFSOVREANURT-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(1,3-thiazol-2-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC(Cl)=CC=2)=C2)=O)C=1N2CC(=O)NC1=NC=CS1 HGBFSOVREANURT-UHFFFAOYSA-N 0.000 claims description 2
- GOFQPQJTEJAVAO-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound O1C(C)=CC(NC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC(Cl)=CC=3)=C2)=N1 GOFQPQJTEJAVAO-UHFFFAOYSA-N 0.000 claims description 2
- WDXUTVMGOUAUCJ-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-methylacetohydrazide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(N)C)C=C1C1=CC=C(Cl)C=C1 WDXUTVMGOUAUCJ-UHFFFAOYSA-N 0.000 claims description 2
- ITUSTXBGCUDYQC-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-phenylacetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC(Cl)=CC=2)=C2)=O)C=1N2CC(=O)NC1=CC=CC=C1 ITUSTXBGCUDYQC-UHFFFAOYSA-N 0.000 claims description 2
- RRJNEQBEAWUJQZ-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-pyrazin-2-ylacetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC(Cl)=CC=2)=C2)=O)C=1N2CC(=O)NC1=CN=CC=N1 RRJNEQBEAWUJQZ-UHFFFAOYSA-N 0.000 claims description 2
- QGWJWUIXGOFFFB-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]acetic acid Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(O)=O)C=C2C1=CC=C(Cl)C=C1 QGWJWUIXGOFFFB-UHFFFAOYSA-N 0.000 claims description 2
- NRTGQYGJONTPAZ-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]acetohydrazide Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(=O)NN)C=C2C1=CC=C(Cl)C=C1 NRTGQYGJONTPAZ-UHFFFAOYSA-N 0.000 claims description 2
- FAOPCYGEDDDLQU-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(1,3-thiazol-2-yl)acetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC(F)=CC=2)=C2)=O)C=1N2CC(=O)NC1=NC=CS1 FAOPCYGEDDDLQU-UHFFFAOYSA-N 0.000 claims description 2
- GFVNVHHOXISPSH-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound O1C(C)=CC(NC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC(F)=CC=3)=C2)=N1 GFVNVHHOXISPSH-UHFFFAOYSA-N 0.000 claims description 2
- ZJGBJMOTPMSWRA-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-methylacetohydrazide Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)N(N)C)C=C1C1=CC=C(F)C=C1 ZJGBJMOTPMSWRA-UHFFFAOYSA-N 0.000 claims description 2
- BIDWBQCYKFEYOA-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]-n-phenylacetamide Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC(F)=CC=2)=C2)=O)C=1N2CC(=O)NC1=CC=CC=C1 BIDWBQCYKFEYOA-UHFFFAOYSA-N 0.000 claims description 2
- DKDOFAALIRSQMH-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]acetic acid Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(O)=O)C=C2C1=CC=C(F)C=C1 DKDOFAALIRSQMH-UHFFFAOYSA-N 0.000 claims description 2
- UWHYAOMLCONVCC-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]acetohydrazide Chemical compound C=1C(C)=CC=C(C2=O)C=1N(CC(=O)NN)C=C2C1=CC=C(F)C=C1 UWHYAOMLCONVCC-UHFFFAOYSA-N 0.000 claims description 2
- NICXRTUJPBTUTM-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-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(OC)C=C1 NICXRTUJPBTUTM-UHFFFAOYSA-N 0.000 claims description 2
- JCGBDGSRVODJJJ-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(1,2-oxazol-3-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=NOC=C1 JCGBDGSRVODJJJ-UHFFFAOYSA-N 0.000 claims description 2
- SCHPJLLBUWCLCI-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(1,3-thiazol-2-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=NC=CS1 SCHPJLLBUWCLCI-UHFFFAOYSA-N 0.000 claims description 2
- GLDXKFJWRMFOGF-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(1-methylpyrazol-3-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=NN(C)C=C1 GLDXKFJWRMFOGF-UHFFFAOYSA-N 0.000 claims description 2
- BDLHPRPHVAZYAM-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=CC(C)=NO1 BDLHPRPHVAZYAM-UHFFFAOYSA-N 0.000 claims description 2
- RADCCJAXEGKZEF-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(5-methyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=CC(C)=NN1 RADCCJAXEGKZEF-UHFFFAOYSA-N 0.000 claims description 2
- KQZOGVUIJKILCH-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-(5-methylpyridin-2-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=CC=C(C)C=N1 KQZOGVUIJKILCH-UHFFFAOYSA-N 0.000 claims description 2
- JSWIKFLZXPHZIX-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=CC=C(C(F)(F)F)C=C1 JSWIKFLZXPHZIX-UHFFFAOYSA-N 0.000 claims description 2
- IYXXIIVRERAXAG-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CN(CC(O)=O)C2=CC(C)=CC=C2C1=O IYXXIIVRERAXAG-UHFFFAOYSA-N 0.000 claims description 2
- YGZUBCKPYHZJIG-UHFFFAOYSA-N 2-[7-methyl-3-(4-methylphenyl)-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(C)C=C1 YGZUBCKPYHZJIG-UHFFFAOYSA-N 0.000 claims description 2
- YNJYJCFSNSHNLI-UHFFFAOYSA-N 2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]-n-(1,3-thiazol-2-yl)acetamide Chemical compound C1=CC(C)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=NC=CS1 YNJYJCFSNSHNLI-UHFFFAOYSA-N 0.000 claims description 2
- MKWCTMIUWSZTFE-UHFFFAOYSA-N 2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]-n-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound O1C(C)=CC(NC(=O)CN2C3=CC(C)=CC=C3C(=O)C(C=3C=CC(C)=CC=3)=C2)=N1 MKWCTMIUWSZTFE-UHFFFAOYSA-N 0.000 claims description 2
- ZJBMMPKOYCZPSC-UHFFFAOYSA-N 2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]-n-phenylacetamide Chemical compound C1=CC(C)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)NC1=CC=CC=C1 ZJBMMPKOYCZPSC-UHFFFAOYSA-N 0.000 claims description 2
- OHEPZBMPGQZQMY-UHFFFAOYSA-N 2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=CN(CC(O)=O)C2=CC(C)=CC=C2C1=O OHEPZBMPGQZQMY-UHFFFAOYSA-N 0.000 claims description 2
- FWLCHFDFCHAPAF-UHFFFAOYSA-N 2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]acetohydrazide Chemical compound C1=CC(C)=CC=C1C1=CN(CC(=O)NN)C2=CC(C)=CC=C2C1=O FWLCHFDFCHAPAF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 claims description 2
- GDUHWXIMLBSYCM-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-methyl-1-(2-oxo-2-piperidin-1-ylethyl)quinolin-4-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)N1CCCCC1 GDUHWXIMLBSYCM-UHFFFAOYSA-N 0.000 claims description 2
- VQAGCTQQELQPBM-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-methyl-1-(2-oxo-2-pyrrolidin-1-ylethyl)quinolin-4-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=CC=C(C)C=C11)=O)=CN1CC(=O)N1CCCC1 VQAGCTQQELQPBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- ZLMKNVMKAKGPDW-UHFFFAOYSA-N 5-methyl-1-(2-morpholin-4-yl-2-oxoethyl)-2-phenylquinolin-4-one Chemical compound C=1C=CC=CC=1C1=CC(=O)C=2C(C)=CC=CC=2N1CC(=O)N1CCOCC1 ZLMKNVMKAKGPDW-UHFFFAOYSA-N 0.000 claims description 2
- PRUPJWANVMZUGZ-UHFFFAOYSA-N 5-methyl-1-(2-morpholin-4-yl-2-oxoethyl)-3-phenylquinolin-4-one Chemical compound C1=C(C=2C=CC=CC=2)C(=O)C=2C(C)=CC=CC=2N1CC(=O)N1CCOCC1 PRUPJWANVMZUGZ-UHFFFAOYSA-N 0.000 claims description 2
- KEFHRAGYZXMZST-UHFFFAOYSA-N 5-methyl-1-(2-oxo-2-piperidin-1-ylethyl)-2-phenylquinolin-4-one Chemical compound C=1C=CC=CC=1C1=CC(=O)C=2C(C)=CC=CC=2N1CC(=O)N1CCCCC1 KEFHRAGYZXMZST-UHFFFAOYSA-N 0.000 claims description 2
- FVTTZCWPVGOQLR-UHFFFAOYSA-N 5-methyl-1-(2-oxo-2-piperidin-1-ylethyl)-3-phenylquinolin-4-one Chemical compound C1=C(C=2C=CC=CC=2)C(=O)C=2C(C)=CC=CC=2N1CC(=O)N1CCCCC1 FVTTZCWPVGOQLR-UHFFFAOYSA-N 0.000 claims description 2
- LAAPZMCNWLYNET-UHFFFAOYSA-N 7-bromo-1-[2-(2,5-dimethyl-2,5-dihydropyrrol-1-yl)-2-oxoethyl]-3-phenylquinolin-4-one Chemical compound CC1C=CC(C)N1C(=O)CN1C2=CC(Br)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 LAAPZMCNWLYNET-UHFFFAOYSA-N 0.000 claims description 2
- JSFWTQSVWIMNGC-UHFFFAOYSA-N 7-bromo-1-[2-(2,6-dimethylmorpholin-4-yl)-2-oxoethyl]-3-phenylquinolin-4-one Chemical compound C1C(C)OC(C)CN1C(=O)CN1C2=CC(Br)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 JSFWTQSVWIMNGC-UHFFFAOYSA-N 0.000 claims description 2
- BRPLCVJDAONFEN-UHFFFAOYSA-N 7-bromo-1-[2-(3,6-dihydro-2h-pyridin-1-yl)-2-oxoethyl]-3-phenylquinolin-4-one Chemical compound C=1C(Br)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCC=CC1 BRPLCVJDAONFEN-UHFFFAOYSA-N 0.000 claims description 2
- OCJVTOMGWDHGEI-UHFFFAOYSA-N 7-methyl-1-(2-morpholin-4-yl-2-oxoethyl)-2-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C=C2C=3C=CC=CC=3)=O)C=1N2CC(=O)N1CCOCC1 OCJVTOMGWDHGEI-UHFFFAOYSA-N 0.000 claims description 2
- ZUHHNQWWVFOVSE-UHFFFAOYSA-N 7-methyl-1-(2-morpholin-4-yl-2-oxoethyl)-3-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCOCC1 ZUHHNQWWVFOVSE-UHFFFAOYSA-N 0.000 claims description 2
- QKLZBIVRNUHIHP-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-piperidin-1-ylethyl)-3-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCCCC1 QKLZBIVRNUHIHP-UHFFFAOYSA-N 0.000 claims description 2
- ZVMBGFYLPYXVGB-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-pyrazin-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=CN=CC=N1 ZVMBGFYLPYXVGB-UHFFFAOYSA-N 0.000 claims description 2
- PUALSSFUDLRAQY-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-pyridin-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=CC=N1 PUALSSFUDLRAQY-UHFFFAOYSA-N 0.000 claims description 2
- PJAGJWUVKXGXNE-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-pyridin-3-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=CN=C1 PJAGJWUVKXGXNE-UHFFFAOYSA-N 0.000 claims description 2
- LMRREPKIIWQGKU-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-pyridin-4-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=NC=C1 LMRREPKIIWQGKU-UHFFFAOYSA-N 0.000 claims description 2
- LGDKXYHXVZUWCX-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-pyrrolidin-1-ylethyl)-2-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C=C2C=3C=CC=CC=3)=O)C=1N2CC(=O)N1CCCC1 LGDKXYHXVZUWCX-UHFFFAOYSA-N 0.000 claims description 2
- LHRXVVIDIBRCQA-UHFFFAOYSA-N 7-methyl-1-(2-oxo-2-pyrrolidin-1-ylethyl)-3-phenylquinolin-4-one Chemical compound C=1C(C)=CC=C(C(C(C=2C=CC=CC=2)=C2)=O)C=1N2CC(=O)N1CCCC1 LHRXVVIDIBRCQA-UHFFFAOYSA-N 0.000 claims description 2
- 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
- XOJMIXHZSVZFBG-UHFFFAOYSA-N 7-methyl-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-3-phenylquinolin-4-one Chemical compound C1CN(C)CCN1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 XOJMIXHZSVZFBG-UHFFFAOYSA-N 0.000 claims description 2
- VWCHQJMNXBQZRE-UHFFFAOYSA-N 7-methyl-1-[2-(5-methylfuran-2-yl)-2-oxoethyl]-3-phenylquinolin-4-one Chemical compound O1C(C)=CC=C1C(=O)CN1C2=CC(C)=CC=C2C(=O)C(C=2C=CC=CC=2)=C1 VWCHQJMNXBQZRE-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 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
- QESXQPWQYLZRDT-UHFFFAOYSA-N methyl 2-(7-methyl-4-oxo-3-phenylquinolin-1-yl)acetate Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)OC)C=C1C1=CC=CC=C1 QESXQPWQYLZRDT-UHFFFAOYSA-N 0.000 claims description 2
- JETJPLNSKJVOCL-UHFFFAOYSA-N methyl 2-[3-(4-chlorophenyl)-7-methyl-4-oxoquinolin-1-yl]acetate Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)OC)C=C1C1=CC=C(Cl)C=C1 JETJPLNSKJVOCL-UHFFFAOYSA-N 0.000 claims description 2
- QEQBLPCPJCUKHT-UHFFFAOYSA-N methyl 2-[3-(4-fluorophenyl)-7-methyl-4-oxoquinolin-1-yl]acetate Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)OC)C=C1C1=CC=C(F)C=C1 QEQBLPCPJCUKHT-UHFFFAOYSA-N 0.000 claims description 2
- OWDILJZIQZHKIB-UHFFFAOYSA-N methyl 2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetate Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)OC)C=C1C1=CC=C(OC)C=C1 OWDILJZIQZHKIB-UHFFFAOYSA-N 0.000 claims description 2
- UFBTXOJPFDLYNH-UHFFFAOYSA-N methyl 2-[7-methyl-3-(4-methylphenyl)-4-oxoquinolin-1-yl]acetate Chemical compound O=C1C2=CC=C(C)C=C2N(CC(=O)OC)C=C1C1=CC=C(C)C=C1 UFBTXOJPFDLYNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- GNUHTQQYTXDSAT-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-2-[3-(4-methoxyphenyl)-7-methyl-4-oxoquinolin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=CN(CC(=O)N(CCO)CCO)C2=CC(C)=CC=C2C1=O GNUHTQQYTXDSAT-UHFFFAOYSA-N 0.000 claims description 2
- SFXCTFCTKUXGBA-UHFFFAOYSA-N n,n-dibutyl-2-(5-methyl-4-oxo-3-phenylquinolin-1-yl)acetamide Chemical compound O=C1C2=C(C)C=CC=C2N(CC(=O)N(CCCC)CCCC)C=C1C1=CC=CC=C1 SFXCTFCTKUXGBA-UHFFFAOYSA-N 0.000 claims description 2
- JYQBCOBHGLKAIB-UHFFFAOYSA-N n,n-dibutyl-2-(7-methyl-4-oxo-2-phenylquinolin-1-yl)acetamide Chemical compound C=1C(=O)C2=CC=C(C)C=C2N(CC(=O)N(CCCC)CCCC)C=1C1=CC=CC=C1 JYQBCOBHGLKAIB-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 229940016681 dipropylacetamide Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 description 47
- 108020003175 receptors Proteins 0.000 description 47
- 239000000243 solution Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000006698 induction Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 229960001475 zolpidem Drugs 0.000 description 6
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229940049706 benzodiazepine Drugs 0.000 description 5
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 5
- 229960003529 diazepam Drugs 0.000 description 5
- 150000002081 enamines Chemical class 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 150000001557 benzodiazepines Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- OFBIFZUFASYYRE-UHFFFAOYSA-N flumazenil Chemical compound C1N(C)C(=O)C2=CC(F)=CC=C2N2C=NC(C(=O)OCC)=C21 OFBIFZUFASYYRE-UHFFFAOYSA-N 0.000 description 4
- 229960004381 flumazenil Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 210000000278 spinal cord Anatomy 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 208000000044 Amnesia Diseases 0.000 description 3
- 208000031091 Amnestic disease Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000006986 amnesia Effects 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003326 hypnotic agent Substances 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229960004010 zaleplon Drugs 0.000 description 3
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- CGKCBYCUHQKZMN-UHFFFAOYSA-N 3-carbamoyl-1-methyl-4-oxoquinoline-2-carboxylic acid Chemical compound C1=CC=C2N(C)C(C(O)=O)=C(C(N)=O)C(=O)C2=C1 CGKCBYCUHQKZMN-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 0 CCOC(C(*)=C(*)Nc1cc(*)cc(*)c1)=O Chemical compound CCOC(C(*)=C(*)Nc1cc(*)cc(*)c1)=O 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 238000003512 Claisen condensation reaction Methods 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000001638 cerebellum Anatomy 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000037023 motor activity Effects 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 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 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- WMKQJWAFNNRSAL-UHFFFAOYSA-N 3-cyclohexa-2,4-dien-1-yl-3h-quinolin-4-one Chemical class C1=NC2=CC=CC=C2C(=O)C1C1CC=CC=C1 WMKQJWAFNNRSAL-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- KELCTBVAWFXTQV-UHFFFAOYSA-N 7-bromo-1-(2-oxo-2-pyrrolidin-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)N1CCCC1 KELCTBVAWFXTQV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CBIAWPMZSFFRGN-UHFFFAOYSA-N Indiplon Chemical compound CC(=O)N(C)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C(=O)C=2SC=CC=2)=C1 CBIAWPMZSFFRGN-UHFFFAOYSA-N 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229940121985 Non-benzodiazepine hypnotic Drugs 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- HFDGGXUVSFYTLN-UHFFFAOYSA-N c1ncc2[nH]ccnc12 Chemical compound c1ncc2[nH]ccnc12 HFDGGXUVSFYTLN-UHFFFAOYSA-N 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 229940114119 gentisate Drugs 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 238000012623 in vivo measurement Methods 0.000 description 1
- 229950003867 indiplon Drugs 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- FITZJYAVATZPMJ-UHFFFAOYSA-L naphthalene-2,6-disulfonate(2-) Chemical compound C1=C(S([O-])(=O)=O)C=CC2=CC(S(=O)(=O)[O-])=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-L 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 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 |
| EP3484528B1 (en) | 2016-07-18 | 2020-11-25 | Janssen Pharmaceutica NV | Tau pet imaging ligands |
| WO2018122746A1 (en) | 2016-12-28 | 2018-07-05 | 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 |
| SMT202500447T1 (it) | 2021-11-02 | 2026-01-12 | Flare Therapeutics Inc | Agonisti inversi di pparg e loro usi |
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 |
| EP1503759B1 (en) * | 2002-05-14 | 2008-12-17 | The Regents Of The University Of California | Substituted quinolone carboxylic acids, their derivatives, site of action, and uses thereof |
-
2007
- 2007-08-09 JP JP2009523299A patent/JP2010500330A/ja active Pending
- 2007-08-09 EP EP07788348A patent/EP2064185B1/en not_active Not-in-force
- 2007-08-09 WO PCT/EP2007/058288 patent/WO2008017710A1/en not_active Ceased
- 2007-08-09 MX MX2009001478A patent/MX2009001478A/es active IP Right Grant
- 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 PL PL07788348T patent/PL2064185T3/pl unknown
- 2007-08-09 AU AU2007283570A patent/AU2007283570A1/en not_active Abandoned
-
2009
- 2009-03-03 NO NO20090971A patent/NO20090971L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090035744A (ko) | 2009-04-10 |
| AU2007283570A1 (en) | 2008-02-14 |
| WO2008017710A1 (en) | 2008-02-14 |
| CA2660421A1 (en) | 2008-02-14 |
| MX2009001478A (es) | 2009-03-31 |
| EP2064185A1 (en) | 2009-06-03 |
| PL2064185T3 (pl) | 2011-11-30 |
| NO20090971L (no) | 2009-04-30 |
| EP2064185B1 (en) | 2011-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2559895C2 (ru) | Азотосодержащие производные гетероарилов | |
| CA2531291A1 (en) | Pyrazoloisoquinoline derivatives as kinase inhibitors | |
| AU2018379321A1 (en) | 1,2,4-oxadiazole derivatives as histone deacetylase 6 inhibitors | |
| JP2013544256A (ja) | 複素環式アミンおよびその使用 | |
| TW201331194A (zh) | 雜芳基化合物及其用途 | |
| WO2016009297A1 (en) | Pyridine derivatives as muscarinic m1 receptor positive allosteric modulators | |
| US11198687B2 (en) | Heteroaryl allosteric modulators of nicotinic acetylcholine receptors | |
| WO2014146493A1 (en) | Acyclic cyanoethylpyrazolo pyridones as janus kinase inhibitors | |
| JP5487100B2 (ja) | アデノシンａ３受容体リガンドとしてのトリアゾロ［１，５−ａ］キノリン | |
| WO2016148232A1 (ja) | モルヒナン誘導体 | |
| JP5205276B2 (ja) | 酵素阻害剤 | |
| CN112601742A (zh) | 组织蛋白酶c抑制剂 | |
| US20100168099A1 (en) | 1h-quinolin-4-one compounds, with affinity for the gaba receptor, processes, uses and compositions | |
| EP2064185B1 (en) | 1h-quinolin-4-one compounds, with affinity for the gaba receptor, processes, uses and compositions | |
| JP7763538B2 (ja) | Ｐａｒｐ７阻害剤及びその使用 | |
| WO2018085171A1 (en) | Substituted bicyclic heteroaryl allosteric modulators of nicotinic acetylcholine receptors | |
| JP3012338B2 (ja) | アリールおよびヘテロアリールアルコキシナフタレン誘導体 | |
| AU2006334364B2 (en) | Imidazo (1,2-a)pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof | |
| ES2369481T3 (es) | Compuestos de 1h-quinolin-4-ona, procedimientos, usos y composiciones. | |
| RU2797613C2 (ru) | Производные 1,2,4-оксадиазола в качестве ингибиторов гистондезацетилазы 6 | |
| JPWO2006075619A1 (ja) | ２−（環状アミノカルボニル）インドリン誘導体及びそれを含有する医薬組成物 | |
| HK1123792B (en) | Imidazo (1,2-a)pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100611 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100611 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121211 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130507 |