SK12012003A3 - Cyclopropylindole derivatives as selective serotonin reuptake inhibitors - Google Patents
Cyclopropylindole derivatives as selective serotonin reuptake inhibitors Download PDFInfo
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- SK12012003A3 SK12012003A3 SK12012003A SK12012003A SK12012003A3 SK 12012003 A3 SK12012003 A3 SK 12012003A3 SK 12012003 A SK12012003 A SK 12012003A SK 12012003 A SK12012003 A SK 12012003A SK 12012003 A3 SK12012003 A3 SK 12012003A3
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- Slovakia
- Prior art keywords
- group
- trans
- cyclopropane
- alkyl
- compound
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- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 title description 7
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 title description 7
- INCAQIRDTKGRNM-UHFFFAOYSA-N 2-cyclopropyl-1h-indole Chemical class C1CC1C1=CC2=CC=CC=C2N1 INCAQIRDTKGRNM-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 206010036596 premature ejaculation Diseases 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 8
- 208000019906 panic disease Diseases 0.000 claims abstract description 8
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 208000002193 Pain Diseases 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 6
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 claims abstract description 5
- -1 dihydroquinolyl Chemical group 0.000 claims description 283
- 239000000203 mixture Substances 0.000 claims description 164
- 229910052757 nitrogen Inorganic materials 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 50
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 44
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000004193 piperazinyl group Chemical group 0.000 claims description 27
- 125000003386 piperidinyl group Chemical group 0.000 claims description 27
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 125000002883 imidazolyl group Chemical group 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000001041 indolyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001544 thienyl group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
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- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 12
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 12
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 12
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000027455 binding Effects 0.000 claims description 11
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 125000005493 quinolyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
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- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- JBVSBLLOZVDAAZ-UHFFFAOYSA-N 2-diazonio-1-[(2-methylpropan-2-yl)oxy]ethenolate Chemical compound CC(C)(C)OC([O-])=C[N+]#N JBVSBLLOZVDAAZ-UHFFFAOYSA-N 0.000 claims description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
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- 239000001301 oxygen Substances 0.000 claims description 4
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- CKXUDRGPWPKVCK-UHFFFAOYSA-N 1-[2-(5,6-difluoro-1h-indol-3-yl)cyclopropyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1CC1C1=CNC2=CC(F)=C(F)C=C12 CKXUDRGPWPKVCK-UHFFFAOYSA-N 0.000 claims description 3
- NJDJOIUKIHRQSS-JQXSQYPDSA-N 3-[(1r,2r)-2-(1-pyrrolidin-1-ylethyl)cyclopropyl]-1h-indole-5-carbonitrile Chemical compound CC([C@H]1[C@@H](C1)C=1C2=CC(=CC=C2NC=1)C#N)N1CCCC1 NJDJOIUKIHRQSS-JQXSQYPDSA-N 0.000 claims description 3
- DEMWBYUAYXJYOC-NWDGAFQWSA-N 3-[(1r,2r)-2-[(dimethylamino)methyl]cyclopropyl]-1h-indole-5-carbonitrile Chemical compound CN(C)C[C@@H]1C[C@H]1C1=CNC2=CC=C(C#N)C=C12 DEMWBYUAYXJYOC-NWDGAFQWSA-N 0.000 claims description 3
- DBGSHMGMGALOBR-HEVMSJOKSA-N 3-[(1r,2r)-2-[1-(dimethylamino)ethyl]cyclopropyl]-1h-indole-5-carbonitrile Chemical compound CN(C)C(C)[C@@H]1C[C@H]1C1=CNC2=CC=C(C#N)C=C12 DBGSHMGMGALOBR-HEVMSJOKSA-N 0.000 claims description 3
- BCICWZZGWJGQJK-UHFFFAOYSA-N 6-[2-[(dimethylamino)methyl]cyclopropyl]-1h-indole-3-carbonitrile Chemical compound CN(C)CC1CC1C1=CC=C(C(=CN2)C#N)C2=C1 BCICWZZGWJGQJK-UHFFFAOYSA-N 0.000 claims description 3
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- JHGSXIXVNCURII-FCHUYYIVSA-N 3-[(1r,2r)-2-[(4-benzylpiperidin-1-yl)methyl]cyclopropyl]-1h-indole-5-carbonitrile Chemical compound C([C@@H]1C[C@H]1C1=CNC2=CC=C(C=C21)C#N)N(CC1)CCC1CC1=CC=CC=C1 JHGSXIXVNCURII-FCHUYYIVSA-N 0.000 claims description 2
- UQCNMBOIQYFDSK-JKSUJKDBSA-N 3-[(1r,2r)-2-[(dipropylamino)methyl]cyclopropyl]-1h-indole-5-carbonitrile Chemical compound CCCN(CCC)C[C@@H]1C[C@H]1C1=CNC2=CC=C(C#N)C=C12 UQCNMBOIQYFDSK-JKSUJKDBSA-N 0.000 claims description 2
- SFJIITPEHFLLPT-PKOBYXMFSA-N 3-[(1r,2r)-2-[[2-(1h-indol-3-yl)ethylamino]methyl]cyclopropyl]-1h-indole-5-carbonitrile Chemical compound C1=CC=C2C(CCNC[C@@H]3C[C@H]3C3=CNC4=CC=C(C=C43)C#N)=CNC2=C1 SFJIITPEHFLLPT-PKOBYXMFSA-N 0.000 claims description 2
- WXDWELIIACHSJV-FXAWDEMLSA-N 3-[(1s,2r)-2-[2-(2-methoxyphenyl)ethylamino]cyclopropyl]-1h-indole-5-carbonitrile Chemical compound COC1=CC=CC=C1CCN[C@H]1[C@H](C=2C3=CC(=CC=C3NC=2)C#N)C1 WXDWELIIACHSJV-FXAWDEMLSA-N 0.000 claims description 2
- ZALXONRNDYIIGY-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]cyclopropyl]-1h-indole-3-carbonitrile Chemical compound CN(C)CC1CC1C1=CC=C(NC=C2C#N)C2=C1 ZALXONRNDYIIGY-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
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- 238000004949 mass spectrometry Methods 0.000 description 179
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Classifications
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- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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| US27988801P | 2001-03-29 | 2001-03-29 | |
| US29312201P | 2001-05-23 | 2001-05-23 | |
| US32780401P | 2001-10-09 | 2001-10-09 | |
| PCT/US2002/006627 WO2002079152A1 (en) | 2001-03-29 | 2002-03-05 | Cyclopropylindole derivatives as selective serotonin reuptake inhibitors |
Publications (1)
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| SK12012003A3 true SK12012003A3 (en) | 2004-10-05 |
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| SK12012003A SK12012003A3 (en) | 2001-03-29 | 2002-03-05 | Cyclopropylindole derivatives as selective serotonin reuptake inhibitors |
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| EP (1) | EP1373203A1 (xx) |
| JP (1) | JP2004531506A (xx) |
| AR (1) | AR035793A1 (xx) |
| BG (1) | BG108207A (xx) |
| CA (1) | CA2442525A1 (xx) |
| CZ (1) | CZ20032644A3 (xx) |
| EE (1) | EE200300478A (xx) |
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| TW200418838A (en) | 2002-09-18 | 2004-10-01 | Bristol Myers Squibb Co | Compounds for the treatment of premature ejaculation |
| US20050065202A1 (en) * | 2003-05-09 | 2005-03-24 | Vidal Ramon Merce | Use of sulphonamide derivatives for the manufacture of a medicament for the prophylaxis and/or treatment of disorders of food ingestion |
| DE10337184A1 (de) * | 2003-08-13 | 2005-03-10 | Gruenenthal Gmbh | Substituierte 3-Pyrrolidin-Indol-Derivate |
| AP2007004024A0 (en) * | 2004-11-29 | 2007-06-30 | Warner Lambert Co | Therapeutic pyrazoloÄ3,4-BÜpyridines and indazoles |
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2002
- 2002-03-05 CA CA002442525A patent/CA2442525A1/en not_active Abandoned
- 2002-03-05 IL IL15804402A patent/IL158044A0/xx unknown
- 2002-03-05 MX MXPA03008807A patent/MXPA03008807A/es unknown
- 2002-03-05 US US10/091,232 patent/US6777437B2/en not_active Expired - Lifetime
- 2002-03-05 CZ CZ20032644A patent/CZ20032644A3/cs unknown
- 2002-03-05 WO PCT/US2002/006627 patent/WO2002079152A1/en not_active Ceased
- 2002-03-05 EP EP02709778A patent/EP1373203A1/en not_active Withdrawn
- 2002-03-05 JP JP2002577779A patent/JP2004531506A/ja active Pending
- 2002-03-05 SK SK12012003A patent/SK12012003A3/sk unknown
- 2002-03-05 HU HU0400343A patent/HUP0400343A2/hu unknown
- 2002-03-05 PL PL02364580A patent/PL364580A1/xx not_active Application Discontinuation
- 2002-03-05 EE EEP200300478A patent/EE200300478A/xx unknown
- 2002-03-26 AR ARP020101100A patent/AR035793A1/es not_active Application Discontinuation
- 2002-03-27 PE PE2002000243A patent/PE20020975A1/es not_active Application Discontinuation
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- 2003-09-26 NO NO20034307A patent/NO20034307L/no not_active Application Discontinuation
- 2003-09-26 IS IS6969A patent/IS6969A/is unknown
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| WO2002079152A1 (en) | 2002-10-10 |
| US6822100B2 (en) | 2004-11-23 |
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| EE200300478A (et) | 2003-12-15 |
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| JP2004531506A (ja) | 2004-10-14 |
| CZ20032644A3 (en) | 2004-06-16 |
| IL158044A0 (en) | 2004-03-28 |
| US20040143003A1 (en) | 2004-07-22 |
| PL364580A1 (en) | 2004-12-13 |
| MXPA03008807A (es) | 2004-02-12 |
| HUP0400343A2 (hu) | 2004-09-28 |
| BG108207A (en) | 2004-12-30 |
| AR035793A1 (es) | 2004-07-14 |
| PE20020975A1 (es) | 2002-10-30 |
| EP1373203A1 (en) | 2004-01-02 |
| CA2442525A1 (en) | 2002-10-10 |
| US20030073849A1 (en) | 2003-04-17 |
| NO20034307D0 (no) | 2003-09-26 |
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