AP463A - "Indoline derivatives as 5HT2c antagonist". - Google Patents

"Indoline derivatives as 5HT2c antagonist". Download PDF

Info

Publication number: AP463A
Authority: AP; ARIPO
Prior art keywords: indoline; chloro; pyridylcarbamoyl; methyl; nmr
Prior art date: 1993-07-06

Application number

APAP/P/1994/000653A

Other languages

English (en)

Other versions

AP9400653A0 (en

Inventor

Peter Ham

Graham Elgin Jones

Ian Thomson Forbes

Original Assignee

Smithkline Beecham Plc

Priority date (The priority date 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 date listed.)

1993-07-06

Filing date

1994-07-04

Publication date

1996-02-19

1994-07-04 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

1994-07-31 Publication of AP9400653A0 publication Critical patent/AP9400653A0/xx

1996-02-19 Application granted granted Critical

1996-02-19 Publication of AP463A publication Critical patent/AP463A/en

Links

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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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)
Eyeglasses (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

APAP/P/1994/000653A 1993-07-06 1994-07-04 "Indoline derivatives as 5HT2c antagonist". AP463A (en)

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 (cs)
EP (1)	EP0707581B1 (cs)
JP (1)	JPH08512299A (cs)
CN (1)	CN1129937A (cs)
AP (1)	AP463A (cs)
AT (1)	ATE149163T1 (cs)
AU (1)	AU7228394A (cs)
CA (1)	CA2166624A1 (cs)
DE (1)	DE69401823T2 (cs)
GB (1)	GB9313913D0 (cs)
IL (1)	IL110204A0 (cs)
MA (1)	MA23254A1 (cs)
TW (1)	TW297023B (cs)
WO (1)	WO1995001976A1 (cs)
ZA (1)	ZA944807B (cs)

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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

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US4428881A (en) *	1977-12-23	1984-01-31	Gulf Oil Corporation	Control of unwanted vegetation with N-carbamylindolines

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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

Patent Citations (1)

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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
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
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 (cs)	1997-02-01
DE69401823T2 (de)	1997-08-28
CA2166624A1 (en)	1995-01-19
GB9313913D0 (en)	1993-08-18
AP9400653A0 (en)	1994-07-31
JPH08512299A (ja)	1996-12-24
AU7228394A (en)	1995-02-06

Publication	Publication Date	Title
EP0707581B1 (en)	1997-02-26	Indoline derivatives as 5ht2c antagonists
KR950010163B1 (ko)	1995-09-11	신규 인돌 유도체
DE69610822T2 (de)	2001-06-07	Indolderivate als 5-ht rezeptorantagoniste
EP0690843B1 (en)	2000-08-30	Formyl- or cyano- substituted indole derivatives having dopaminergic activity
JPH11513391A (ja)	1999-11-16	Ｃｃ−１０６５及びズオカーマイシンのｃｂｉ類縁体
FR2804114A1 (fr)	2001-07-27	Nouveaux derives de 1,3-dihydro-2h-indol-2-one, un procede pour leur preparation et les compositions pharmaceutiques en contenant
WO2003013510A1 (en)	2003-02-20	3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders
CN101351446A (zh)	2009-01-21	新的稠合吡咯衍生物
WO2001023374A1 (en)	2001-04-05	Piperazine derivatives as 5-ht1b antagonists
EP1296976B1 (fr)	2005-01-26	Derives de 1,3-dihydro-2h-indol-2-one et leur utilisation en tant que ligands des recepteurs v1b et v1a de l'arginine-vasopressine
KR20070114123A (ko)	2007-11-29	염증 치료에 유용한 인돌
EA011320B1 (ru)	2009-02-27	N-арилсульфонил-3-замещенные индолы, обладающие афинностью к серотониновому рецептору, способ их получения и содержащая их фармацевтическая композиция
FR2827604A1 (fr)	2003-01-24	Nouveaux derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2- one, un procede pour leur preparation et les compositions pharmaceutiques en contenant
EP2887803A1 (en)	2015-07-01	Pro-neurogenic compounds
JP2001526643A (ja)	2001-12-18	５ｈｔ１ａ、５ｈｔ１ｂおよび５ｈｔ１ｄ受容体アンタゴニスト活性を合わせ持つ化合物を含む二環式アリールまたは二環式複素環
KR20020027622A (ko)	2002-04-13	중추신경계 질병 치료용 아미노알콕시 카르바졸
AU2006237920A1 (en)	2006-10-26	Nitrogen-containing heterocyclic compound
FR2805536A1 (fr)	2001-08-31	Nouveaux derives de 1,3-dihydro-2h-indol-2-one, un procede pour leur preparation et les compositions pharmaceutiques en contenant
JP2005516951A (ja)	2005-06-09	尿素誘導体およびバニロイド受容体アンタゴニストとしてのその使用
EP1487801A1 (en)	2004-12-22	7-arylsulfonamido-2,3,4,5-tetrahydro-1h-benzo[d]azepine derivatives with 5-ht6 receptor affinity for the treatment of cns disorders
CA2621720A1 (en)	2007-03-29	Carbazole derivatives
CN1437597A (zh)	2003-08-20	取代的苯基－哌嗪衍生物及其制备和用途
WO2009115685A1 (fr)	2009-09-24	Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique.
CZ289799B6 (cs)	2002-04-17	Indolinový derivát jako antagonista 5-HT-2C receptoru
KR100363484B1 (ko)	2003-02-05	3-치환1-아릴인돌화합물