CA2166624A1 - Indoline derivatives as 5ht2c antagonists - Google Patents
Indoline derivatives as 5ht2c antagonistsInfo
- Publication number
- CA2166624A1 CA2166624A1 CA002166624A CA2166624A CA2166624A1 CA 2166624 A1 CA2166624 A1 CA 2166624A1 CA 002166624 A CA002166624 A CA 002166624A CA 2166624 A CA2166624 A CA 2166624A CA 2166624 A1 CA2166624 A1 CA 2166624A1
- Authority
- CA
- Canada
- Prior art keywords
- indoline
- pyridylcarbamoyl
- chloro
- methyl
- alkyl
- 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.)
- Abandoned
Links
- 239000005557 antagonist Substances 0.000 title description 3
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Chemical group 0.000 claims abstract description 3
- 238000011282 treatment Methods 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 14
- 229910006095 SO2F Inorganic materials 0.000 claims abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- FJUARYIMIPGIJS-UHFFFAOYSA-N 4-chloro-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(Cl)C(C)=CC=C2N1C(=O)NC1=CC=CN=C1 FJUARYIMIPGIJS-UHFFFAOYSA-N 0.000 claims description 4
- YSGSQACIWFDMAJ-UHFFFAOYSA-N 5-phenyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(C=3C=CC=CC=3)=CC=C2N1C(=O)NC1=CC=CN=C1 YSGSQACIWFDMAJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- NLNBNROVVZQUSP-UHFFFAOYSA-N 4-bromo-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(Br)C(C)=CC=C2N1C(=O)NC1=CC=CN=C1 NLNBNROVVZQUSP-UHFFFAOYSA-N 0.000 claims description 3
- KBIGCTQWHDNTLK-UHFFFAOYSA-N 4-chloro-5-methylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(Cl)C(SC)=CC=C2N1C(=O)NC1=CC=CN=C1 KBIGCTQWHDNTLK-UHFFFAOYSA-N 0.000 claims description 3
- LOLNBESEFOMRHG-UHFFFAOYSA-N 6-bromo-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Br)C(C)=CC=2CCN1C(=O)NC1=CC=CN=C1 LOLNBESEFOMRHG-UHFFFAOYSA-N 0.000 claims description 3
- YDUBGXHYRPGOAZ-UHFFFAOYSA-N 6-bromo-5-propylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Br)C(SCCC)=CC=2CCN1C(=O)NC1=CC=CN=C1 YDUBGXHYRPGOAZ-UHFFFAOYSA-N 0.000 claims description 3
- ILEVMOFZKXQODL-UHFFFAOYSA-N 6-chloro-5-ethenyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC=2C=C(C=C)C(Cl)=CC=2N1C(=O)NC1=CC=CN=C1 ILEVMOFZKXQODL-UHFFFAOYSA-N 0.000 claims description 3
- OUQBLYJEKPCIMP-UHFFFAOYSA-N 6-chloro-5-ethyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(CC)=CC=2CCN1C(=O)NC1=CC=CN=C1 OUQBLYJEKPCIMP-UHFFFAOYSA-N 0.000 claims description 3
- JQICQYRHIKFUGD-UHFFFAOYSA-N 6-chloro-5-iodo-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC=2C=C(I)C(Cl)=CC=2N1C(=O)NC1=CC=CN=C1 JQICQYRHIKFUGD-UHFFFAOYSA-N 0.000 claims description 3
- UFWVDYDZMXVCCJ-UHFFFAOYSA-N 6-chloro-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(C)=CC=2CCN1C(=O)NC1=CC=CN=C1 UFWVDYDZMXVCCJ-UHFFFAOYSA-N 0.000 claims description 3
- MRLTTXUXAHTDRR-UHFFFAOYSA-N 6-chloro-5-methyl-n-pyridin-4-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(C)=CC=2CCN1C(=O)NC1=CC=NC=C1 MRLTTXUXAHTDRR-UHFFFAOYSA-N 0.000 claims description 3
- GYVNZUJLZLMDFJ-UHFFFAOYSA-N 6-chloro-5-propyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(CCC)=CC=2CCN1C(=O)NC1=CC=CN=C1 GYVNZUJLZLMDFJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- XNRDHEFXDKDCMQ-UHFFFAOYSA-N 5-chloro-6-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC=2C=C(Cl)C(C)=CC=2N1C(=O)NC1=CC=CN=C1 XNRDHEFXDKDCMQ-UHFFFAOYSA-N 0.000 claims description 2
- QUYCDINJTDAKPI-UHFFFAOYSA-N 5-ethylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(SCC)=CC=C2N1C(=O)NC1=CC=CN=C1 QUYCDINJTDAKPI-UHFFFAOYSA-N 0.000 claims description 2
- IRRJKRJNCNEHIL-UHFFFAOYSA-N 5-methylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(SC)=CC=C2N1C(=O)NC1=CC=CN=C1 IRRJKRJNCNEHIL-UHFFFAOYSA-N 0.000 claims description 2
- VBIZDMWYWUAKCO-UHFFFAOYSA-N 5-nitro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC([N+](=O)[O-])=CC=C2N1C(=O)NC1=CC=CN=C1 VBIZDMWYWUAKCO-UHFFFAOYSA-N 0.000 claims description 2
- WNWFIXVUQPDYNA-UHFFFAOYSA-N 6-chloro-5-ethylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(SCC)=CC=2CCN1C(=O)NC1=CC=CN=C1 WNWFIXVUQPDYNA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- ZHENAFZDGOXHIQ-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)-6-chloro-5-methyl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(C)=CC=2CCN1C(=O)NC1=CN=CC(Br)=C1 ZHENAFZDGOXHIQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- ZDDXCYKFUQNTQB-UHFFFAOYSA-N 4,5-dichloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(Cl)C(Cl)=CC=C2N1C(=O)NC1=CC=CN=C1 ZDDXCYKFUQNTQB-UHFFFAOYSA-N 0.000 claims 1
- MCMJACABBYFBRJ-UHFFFAOYSA-N 4,6-dichloro-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(Cl)C(C)=C(Cl)C=C2N1C(=O)NC1=CC=CN=C1 MCMJACABBYFBRJ-UHFFFAOYSA-N 0.000 claims 1
- IFMKJNSSPPAQOQ-UHFFFAOYSA-N 4-iodo-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(I)C(C)=CC=C2N1C(=O)NC1=CC=CN=C1 IFMKJNSSPPAQOQ-UHFFFAOYSA-N 0.000 claims 1
- NUYRXFCMGKSSNP-UHFFFAOYSA-N 5,6-dichloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(Cl)=CC=2CCN1C(=O)NC1=CC=CN=C1 NUYRXFCMGKSSNP-UHFFFAOYSA-N 0.000 claims 1
- KBWLFKZKDRWOOP-UHFFFAOYSA-N 5-(dimethylamino)-n-(2-methylquinolin-4-yl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=CC=C2C(NC(=O)N3C4=CC=C(C=C4CC3)N(C)C)=CC(C)=NC2=C1 KBWLFKZKDRWOOP-UHFFFAOYSA-N 0.000 claims 1
- CBDUBPRIZSXHOV-UHFFFAOYSA-N 5-(dimethylamino)-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(N(C)C)=CC=C2N1C(=O)NC1=CC=CN=C1 CBDUBPRIZSXHOV-UHFFFAOYSA-N 0.000 claims 1
- QWWIPMXYCFVJFJ-UHFFFAOYSA-N 5-bromo-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(Br)=CC=C2N1C(=O)NC1=CC=CN=C1 QWWIPMXYCFVJFJ-UHFFFAOYSA-N 0.000 claims 1
- BYXYRVSXGVLRKM-UHFFFAOYSA-N 5-chloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(Cl)=CC=C2N1C(=O)NC1=CC=CN=C1 BYXYRVSXGVLRKM-UHFFFAOYSA-N 0.000 claims 1
- KGFDFBKKNJTMJX-UHFFFAOYSA-N 5-tert-butyl-4-chloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=C(Cl)C(C(C)(C)C)=CC=C2N1C(=O)NC1=CC=CN=C1 KGFDFBKKNJTMJX-UHFFFAOYSA-N 0.000 claims 1
- NJCWASKCTHVLLT-UHFFFAOYSA-N 5-tert-butyl-6-chloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(C(C)(C)C)=CC=2CCN1C(=O)NC1=CC=CN=C1 NJCWASKCTHVLLT-UHFFFAOYSA-N 0.000 claims 1
- SUTFBUFCLSOFQF-UHFFFAOYSA-N 6,7-dichloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C12=C(Cl)C(Cl)=CC=C2CCN1C(=O)NC1=CC=CN=C1 SUTFBUFCLSOFQF-UHFFFAOYSA-N 0.000 claims 1
- VFDSFIDQQPMNEX-UHFFFAOYSA-N 6-bromo-5-methylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Br)C(SC)=CC=2CCN1C(=O)NC1=CC=CN=C1 VFDSFIDQQPMNEX-UHFFFAOYSA-N 0.000 claims 1
- VQJYXENSGGKYBD-UHFFFAOYSA-N 6-chloro-5-methylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(SC)=CC=2CCN1C(=O)NC1=CC=CN=C1 VQJYXENSGGKYBD-UHFFFAOYSA-N 0.000 claims 1
- HDBXAVYYGFJNFM-UHFFFAOYSA-N 6-chloro-5-propan-2-yl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(C(C)C)=CC=2CCN1C(=O)NC1=CC=CN=C1 HDBXAVYYGFJNFM-UHFFFAOYSA-N 0.000 claims 1
- FGTRCUOWUGYCLD-UHFFFAOYSA-N 6-chloro-5-propan-2-ylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Cl)C(SC(C)C)=CC=2CCN1C(=O)NC1=CC=CN=C1 FGTRCUOWUGYCLD-UHFFFAOYSA-N 0.000 claims 1
- LOMPSBWQXLVHJX-UHFFFAOYSA-N 6-chloro-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C12=CC(Cl)=CC=C2CCN1C(=O)NC1=CC=CN=C1 LOMPSBWQXLVHJX-UHFFFAOYSA-N 0.000 claims 1
- JCRAEXACIZJAKA-UHFFFAOYSA-N 6-iodo-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(I)C(C)=CC=2CCN1C(=O)NC1=CC=CN=C1 JCRAEXACIZJAKA-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- JDEDDUYWHVGXBK-UHFFFAOYSA-N n-pyridin-3-yl-5-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2N1C(=O)NC1=CC=CN=C1 JDEDDUYWHVGXBK-UHFFFAOYSA-N 0.000 claims 1
- KIAWWMDXYYZGJQ-UHFFFAOYSA-N n-pyridin-3-yl-5-thiophen-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(C3=CSC=C3)=CC=C2N1C(=O)NC1=CC=CN=C1 KIAWWMDXYYZGJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- -1 SCF3 Chemical group 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 7
- 208000015114 central nervous system disease Diseases 0.000 abstract description 3
- 229940044551 receptor antagonist Drugs 0.000 abstract description 3
- 239000002464 receptor antagonist Substances 0.000 abstract description 3
- 229940116892 5 Hydroxytryptamine 2B receptor antagonist Drugs 0.000 abstract 1
- 239000002891 serotonin 2B antagonist Substances 0.000 abstract 1
- 239000002484 serotonin 2C antagonist Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 79
- 101150041968 CDC13 gene Proteins 0.000 description 64
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 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 31
- 229910052708 sodium Inorganic materials 0.000 description 31
- 239000011734 sodium Substances 0.000 description 31
- 239000003921 oil Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 16
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 14
- 229960004756 ethanol Drugs 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
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- 150000001540 azides Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- OPMNROCQHKJDAQ-FKSUSPILSA-N loline Chemical compound C1C[C@@H]2O[C@H]3[C@H](NC)[C@@H]2N1C3 OPMNROCQHKJDAQ-FKSUSPILSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 102100022210 COX assembly mitochondrial protein 2 homolog Human genes 0.000 description 5
- 101100225553 Caenorhabditis elegans epg-4 gene Proteins 0.000 description 5
- 101000900446 Homo sapiens COX assembly mitochondrial protein 2 homolog Proteins 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CFGKECNZKWERMQ-UHFFFAOYSA-N 6-chloro-5-ethenyl-2,3-dihydro-1h-indole Chemical compound C1=C(C=C)C(Cl)=CC2=C1CCN2 CFGKECNZKWERMQ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000282320 Panthera leo Species 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- LCFDJWUYKUPBJM-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-indole Chemical compound FC(F)(F)C1=CC=C2NC=CC2=C1 LCFDJWUYKUPBJM-UHFFFAOYSA-N 0.000 description 3
- KHJBSNUBUOHZAG-UHFFFAOYSA-N 6-chloro-5-iodo-1h-indole Chemical compound C1=C(I)C(Cl)=CC2=C1C=CN2 KHJBSNUBUOHZAG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- AVDXUVZURBFCNE-UHFFFAOYSA-N lolin Natural products CC1C(O)C(O)C2(COC(=O)C)C(CCC=C2CO)C13CC(OC3=O)c4cocc4 AVDXUVZURBFCNE-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229950008693 mesulergine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- ODXHNGJYIWHPAG-UHFFFAOYSA-N n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC=CC=C2N1C(=O)NC1=CC=CN=C1 ODXHNGJYIWHPAG-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940073020 nitrol Drugs 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07D401/02—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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Eyeglasses (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9313913.7 | 1993-07-06 | ||
| GB939313913A GB9313913D0 (en) | 1993-07-06 | 1993-07-06 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2166624A1 true CA2166624A1 (en) | 1995-01-19 |
Family
ID=10738344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002166624A Abandoned CA2166624A1 (en) | 1993-07-06 | 1994-06-30 | Indoline derivatives as 5ht2c antagonists |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5834494A (enExample) |
| EP (1) | EP0707581B1 (enExample) |
| JP (1) | JPH08512299A (enExample) |
| CN (1) | CN1129937A (enExample) |
| AP (1) | AP463A (enExample) |
| AT (1) | ATE149163T1 (enExample) |
| AU (1) | AU7228394A (enExample) |
| CA (1) | CA2166624A1 (enExample) |
| DE (1) | DE69401823T2 (enExample) |
| GB (1) | GB9313913D0 (enExample) |
| IL (1) | IL110204A0 (enExample) |
| MA (1) | MA23254A1 (enExample) |
| TW (1) | TW297023B (enExample) |
| WO (1) | WO1995001976A1 (enExample) |
| ZA (1) | ZA944807B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5618824A (en) * | 1994-03-09 | 1997-04-08 | Merrell Pharmaceuticals Inc. | Treatment of obsessive-compulsive disorders with 5-HT2 antagonists |
| GB9414139D0 (en) * | 1994-07-13 | 1994-08-31 | Smithkline Beecham Plc | Novel compounds |
| GB9420521D0 (en) * | 1994-10-12 | 1994-11-30 | Smithkline Beecham Plc | Novel compounds |
| WO1996023769A2 (en) * | 1995-02-02 | 1996-08-08 | Smithkline Beecham Plc | Heterocyclic compounds possessing 5ht2c receptor antagonist activity |
| NZ301265A (en) * | 1995-02-02 | 1998-12-23 | Smithkline Beecham Plc | Indole derivatives as 5ht receptor antagonists, preparation and pharmaceutical compositions thereof |
| GB9517559D0 (en) * | 1995-08-26 | 1995-10-25 | Smithkline Beecham Plc | Novel compounds |
| WO1997043281A1 (en) * | 1996-05-16 | 1997-11-20 | Allelix Biopharmaceuticals Inc. | Thiophene- and furan-tryptamine derivatives |
| GB9612885D0 (en) * | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
| GB9612883D0 (en) * | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
| US6362009B1 (en) | 1997-11-21 | 2002-03-26 | Merck & Co., Inc. | Solid phase synthesis of heterocycles |
| FR2778662B1 (fr) * | 1998-05-12 | 2000-06-16 | Adir | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA2347095A1 (en) * | 1998-10-16 | 2000-04-27 | Takeda Chemical Industries, Ltd. | Nitrogen-containing condensed heterocyclic derivatives, their production and agent |
| US6453357B1 (en) | 1999-01-07 | 2002-09-17 | Cisco Technology, Inc. | Method and system for processing fragments and their out-of-order delivery during address translation |
| US6465467B1 (en) | 1999-05-21 | 2002-10-15 | Biovitrum Ab | Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases |
| CA2374898C (en) * | 1999-05-21 | 2009-12-08 | Biovitrum Ab | Pyrazinyl-piperazine compounds, their use and preparation |
| UA77650C2 (en) | 1999-12-06 | 2007-01-15 | Lundbeck & Co As H | Use of serotonin reuptake inhibitor in combination with deramcyclane |
| FR2810979B1 (fr) * | 2000-06-29 | 2002-08-23 | Adir | Nouveaux derives de diphenyluree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0019950D0 (en) * | 2000-08-12 | 2000-09-27 | Smithkline Beecham Plc | Compounds |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| ATE241155T1 (de) * | 2001-07-09 | 2003-06-15 | Cit Alcatel | Verbinder für optische fasern |
| US6861440B2 (en) | 2001-10-26 | 2005-03-01 | Hoffmann-La Roche Inc. | DPP IV inhibitors |
| FR2837823B1 (fr) * | 2002-03-27 | 2005-04-08 | Servier Lab | Nouveaux derives d'indoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| BR0311970A (pt) | 2002-06-19 | 2005-03-29 | Biovitrum Ab | Novos compostos, seu uso e preparação |
| ATE437876T1 (de) | 2003-06-20 | 2009-08-15 | Hoffmann La Roche | Hexahydropyridoisochinoline als dpp-iv- inhibitoren |
| MXPA05013904A (es) | 2003-06-20 | 2006-02-24 | Hoffmann La Roche | Derivados de pirido[2,1-a] isoquinolinas como inhibidores de dipeptidil-peptidasa iv(dpp-iv). |
| EP1931622B1 (en) * | 2005-09-13 | 2011-08-24 | Bayer CropScience AG | Phenyloxy substituted phenylamidine derivatives as pesticides |
| US9052304B2 (en) | 2009-03-13 | 2015-06-09 | Terrasep, Llc | Methods and apparatus for centrifugal liquid chromatography |
| CN106278987A (zh) * | 2016-08-16 | 2017-01-04 | 都创(上海)医药科技有限公司 | 吲哚啉类化合物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4428881A (en) * | 1977-12-23 | 1984-01-31 | Gulf Oil Corporation | Control of unwanted vegetation with N-carbamylindolines |
| JPH06500551A (ja) * | 1990-09-13 | 1994-01-20 | ビーチャム・グループ・パブリック・リミテッド・カンパニー | ５ｈｔ受容体アンタゴニストとしてのインドールウレア |
| CA2142721A1 (en) * | 1992-08-20 | 1994-03-03 | Ian T. Forbes | Condensed indole derivatives as 5ht and 5ht antagonists |
-
1993
- 1993-07-06 GB GB939313913A patent/GB9313913D0/en active Pending
-
1994
- 1994-06-30 EP EP94921638A patent/EP0707581B1/en not_active Expired - Lifetime
- 1994-06-30 AU AU72283/94A patent/AU7228394A/en not_active Abandoned
- 1994-06-30 CN CN94193185A patent/CN1129937A/zh active Pending
- 1994-06-30 DE DE69401823T patent/DE69401823T2/de not_active Expired - Fee Related
- 1994-06-30 JP JP7503812A patent/JPH08512299A/ja active Pending
- 1994-06-30 AT AT94921638T patent/ATE149163T1/de not_active IP Right Cessation
- 1994-06-30 WO PCT/EP1994/002148 patent/WO1995001976A1/en not_active Ceased
- 1994-06-30 CA CA002166624A patent/CA2166624A1/en not_active Abandoned
- 1994-07-04 AP APAP/P/1994/000653A patent/AP463A/en active
- 1994-07-04 MA MA23564A patent/MA23254A1/fr unknown
- 1994-07-04 IL IL11020494A patent/IL110204A0/xx unknown
- 1994-07-04 ZA ZA944807A patent/ZA944807B/xx unknown
- 1994-07-05 TW TW083106150A patent/TW297023B/zh active
-
1996
- 1996-09-23 US US08/717,957 patent/US5834494A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995001976A1 (en) | 1995-01-19 |
| EP0707581A1 (en) | 1996-04-24 |
| DE69401823D1 (de) | 1997-04-03 |
| MA23254A1 (fr) | 1995-04-01 |
| IL110204A0 (en) | 1995-01-24 |
| AP463A (en) | 1996-02-19 |
| ATE149163T1 (de) | 1997-03-15 |
| CN1129937A (zh) | 1996-08-28 |
| EP0707581B1 (en) | 1997-02-26 |
| ZA944807B (en) | 1996-01-04 |
| US5834494A (en) | 1998-11-10 |
| TW297023B (enExample) | 1997-02-01 |
| DE69401823T2 (de) | 1997-08-28 |
| GB9313913D0 (en) | 1993-08-18 |
| AP9400653A0 (en) | 1994-07-31 |
| JPH08512299A (ja) | 1996-12-24 |
| AU7228394A (en) | 1995-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |