AP463A - "Indoline derivatives as 5HT2c antagonist". - Google Patents
"Indoline derivatives as 5HT2c antagonist". Download PDFInfo
- Publication number
- AP463A AP463A APAP/P/1994/000653A AP9400653A AP463A AP 463 A AP463 A AP 463A AP 9400653 A AP9400653 A AP 9400653A AP 463 A AP463 A AP 463A
- Authority
- AP
- ARIPO
- Prior art keywords
- indoline
- chloro
- pyridylcarbamoyl
- methyl
- nmr
- Prior art date
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- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title description 5
- 239000002484 serotonin 2C antagonist Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- 238000000034 method Methods 0.000 claims abstract description 98
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Chemical group 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 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 description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 description 4
- 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 4
- 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 description 4
- VUJXFEKATKVBBP-UHFFFAOYSA-N 6-bromo-5-ethylsulfanyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(Br)C(SCC)=CC=2CCN1C(=O)NC1=CC=CN=C1 VUJXFEKATKVBBP-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910006095 SO2F Inorganic materials 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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 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
- 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 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- DWZCCUPWPGYNMI-UHFFFAOYSA-N 5-iodo-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(I)=CC=C2N1C(=O)NC1=CC=CN=C1 DWZCCUPWPGYNMI-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
- 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 description 2
- 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 description 2
- 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 2
- 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 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
- 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 2
- YMQBRDYKNWNOQA-UHFFFAOYSA-N 6-chloro-5-methyl-n-(3-methyl-1,2-oxazol-5-yl)-2,3-dihydroindole-1-carboxamide Chemical compound O1N=C(C)C=C1NC(=O)N1C2=CC(Cl)=C(C)C=C2CC1 YMQBRDYKNWNOQA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- HOVMHIRTZYQSKM-UHFFFAOYSA-N 6-chloro-5-methyl-n-quinolin-5-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=CC=C2C(NC(=O)N3CCC=4C=C(C(=CC=43)Cl)C)=CC=CC2=N1 HOVMHIRTZYQSKM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 2
- 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 description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 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 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 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
- 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
- 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
- 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
- KXGXRAYAEKKRTR-UHFFFAOYSA-N 6-fluoro-5-methyl-n-pyridin-3-yl-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(F)C(C)=CC=2CCN1C(=O)NC1=CC=CN=C1 KXGXRAYAEKKRTR-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- ZYAVZXUEXDSCMB-UHFFFAOYSA-N methyl 6-chloro-1-(pyridin-3-ylcarbamoyl)-2,3-dihydroindole-5-carboxylate Chemical compound C1=2C=C(Cl)C(C(=O)OC)=CC=2CCN1C(=O)NC1=CC=CN=C1 ZYAVZXUEXDSCMB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- -1 c2-6 alkanonyl Chemical group 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
- 239000000203 mixture Substances 0.000 description 95
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 82
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- 239000007787 solid Substances 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 229960004756 ethanol Drugs 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
- 239000003921 oil Substances 0.000 description 24
- SHVVSKCXWMEDRW-UHFFFAOYSA-N 3-isocyanatopyridine Chemical compound O=C=NC1=CC=CN=C1 SHVVSKCXWMEDRW-UHFFFAOYSA-N 0.000 description 23
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 229940093499 ethyl acetate Drugs 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- ZAMJLADJGLXVOJ-UHFFFAOYSA-N 6-chloro-5-methyl-2,3-dihydro-1h-indole Chemical compound C1=C(Cl)C(C)=CC2=C1NCC2 ZAMJLADJGLXVOJ-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 229960004132 diethyl ether Drugs 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000007832 Na2SO4 Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229960001866 silicon dioxide Drugs 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- WUTIWOZYHHSBBU-UHFFFAOYSA-N 3-methoxy-4-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1[N+]([O-])=O WUTIWOZYHHSBBU-UHFFFAOYSA-N 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- RNTCWULFNYNFGI-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CCC2=C1 RNTCWULFNYNFGI-UHFFFAOYSA-N 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
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- 239000000375 suspending agent Substances 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000006365 thiocyanation reaction Methods 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 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)
- Plural Heterocyclic Compounds (AREA)
- Eyeglasses (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939313913A GB9313913D0 (en) | 1993-07-06 | 1993-07-06 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9400653A0 AP9400653A0 (en) | 1994-07-31 |
| AP463A true AP463A (en) | 1996-02-19 |
Family
ID=10738344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1994/000653A AP463A (en) | 1993-07-06 | 1994-07-04 | "Indoline derivatives as 5HT2c antagonist". |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5834494A (OSRAM) |
| EP (1) | EP0707581B1 (OSRAM) |
| JP (1) | JPH08512299A (OSRAM) |
| CN (1) | CN1129937A (OSRAM) |
| AP (1) | AP463A (OSRAM) |
| AT (1) | ATE149163T1 (OSRAM) |
| AU (1) | AU7228394A (OSRAM) |
| CA (1) | CA2166624A1 (OSRAM) |
| DE (1) | DE69401823T2 (OSRAM) |
| GB (1) | GB9313913D0 (OSRAM) |
| IL (1) | IL110204A0 (OSRAM) |
| MA (1) | MA23254A1 (OSRAM) |
| TW (1) | TW297023B (OSRAM) |
| WO (1) | WO1995001976A1 (OSRAM) |
| ZA (1) | ZA944807B (OSRAM) |
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 |
| CN1151147C (zh) * | 1995-02-02 | 2004-05-26 | 史密丝克莱恩比彻姆有限公司 | 作为5-ht受体拮抗剂的吲哚衍生物 |
| WO1996023769A2 (en) * | 1995-02-02 | 1996-08-08 | Smithkline Beecham Plc | Heterocyclic compounds possessing 5ht2c receptor antagonist activity |
| GB9517559D0 (en) * | 1995-08-26 | 1995-10-25 | Smithkline Beecham Plc | Novel compounds |
| CA2253941A1 (en) * | 1996-05-16 | 1997-11-20 | Sumanas Rakhit | 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 |
| AU6123699A (en) * | 1998-10-16 | 2000-05-08 | Takeda Chemical Industries Ltd. | Nitrogenous fused heterocycle compounds, process for the preparation thereof andagents containing the same |
| 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 |
| DK1178973T3 (da) * | 1999-05-21 | 2006-05-08 | Biovitrum Ab | Pyrazinyl-piperazin-forbindelser, deres anvendelse og fremstilling |
| 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 |
| 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 |
| EP1278085B1 (en) * | 2001-07-09 | 2003-05-21 | Alcatel | Connector for optical fibers |
| 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 |
| NZ536664A (en) | 2002-06-19 | 2007-07-27 | Biovitrum Ab | Piperazinylpyrazine derivative compounds, their use and preparation |
| WO2005000846A1 (en) | 2003-06-20 | 2005-01-06 | F.Hoffmann-La Roche Ag | Hexahydropyridoisoqinolines as dpp-iv inhibitors |
| 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 |
| US8277650B2 (en) | 2009-03-13 | 2012-10-02 | 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 |
Citations (1)
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328922A (en) * | 1990-09-13 | 1994-07-12 | Beecham Group P.L.C. | Indole ureas as 5 ht receptor antagonist |
| EP0656003A1 (en) * | 1992-08-20 | 1995-06-07 | Smithkline Beecham Plc | Condensed indole derivatives as 5ht2c and 5ht2b antagonists |
-
1993
- 1993-07-06 GB GB939313913A patent/GB9313913D0/en active Pending
-
1994
- 1994-06-30 WO PCT/EP1994/002148 patent/WO1995001976A1/en not_active Ceased
- 1994-06-30 EP EP94921638A patent/EP0707581B1/en not_active Expired - Lifetime
- 1994-06-30 JP JP7503812A patent/JPH08512299A/ja active Pending
- 1994-06-30 DE DE69401823T patent/DE69401823T2/de not_active Expired - Fee Related
- 1994-06-30 AT AT94921638T patent/ATE149163T1/de not_active IP Right Cessation
- 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 CA CA002166624A patent/CA2166624A1/en not_active Abandoned
- 1994-07-04 IL IL11020494A patent/IL110204A0/xx unknown
- 1994-07-04 AP APAP/P/1994/000653A patent/AP463A/en active
- 1994-07-04 ZA ZA944807A patent/ZA944807B/xx unknown
- 1994-07-04 MA MA23564A patent/MA23254A1/fr 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
Patent Citations (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2166624A1 (en) | 1995-01-19 |
| DE69401823T2 (de) | 1997-08-28 |
| MA23254A1 (fr) | 1995-04-01 |
| US5834494A (en) | 1998-11-10 |
| AU7228394A (en) | 1995-02-06 |
| DE69401823D1 (de) | 1997-04-03 |
| EP0707581B1 (en) | 1997-02-26 |
| AP9400653A0 (en) | 1994-07-31 |
| EP0707581A1 (en) | 1996-04-24 |
| CN1129937A (zh) | 1996-08-28 |
| TW297023B (OSRAM) | 1997-02-01 |
| ATE149163T1 (de) | 1997-03-15 |
| ZA944807B (en) | 1996-01-04 |
| GB9313913D0 (en) | 1993-08-18 |
| JPH08512299A (ja) | 1996-12-24 |
| WO1995001976A1 (en) | 1995-01-19 |
| IL110204A0 (en) | 1995-01-24 |
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