FR2458550A1 - Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant - Google Patents
Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant Download PDFInfo
- Publication number
- FR2458550A1 FR2458550A1 FR7914979A FR7914979A FR2458550A1 FR 2458550 A1 FR2458550 A1 FR 2458550A1 FR 7914979 A FR7914979 A FR 7914979A FR 7914979 A FR7914979 A FR 7914979A FR 2458550 A1 FR2458550 A1 FR 2458550A1
- Authority
- FR
- France
- Prior art keywords
- indole
- carbon atoms
- tetrahydropyridin
- atom
- radical containing
- 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.)
- Granted
Links
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- 239000003176 neuroleptic agent Substances 0.000 title abstract description 3
- 230000000701 neuroleptic effect Effects 0.000 title abstract description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 24
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 4
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- 125000004076 pyridyl group Chemical group 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- -1 alkoxy radical Chemical group 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- XUDGCZURHPXFLU-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydropyridin-4-yl)-1h-indole Chemical class C1=CNCCC1C1=CC2=CC=CC=C2N1 XUDGCZURHPXFLU-UHFFFAOYSA-N 0.000 claims description 9
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- 239000011707 mineral Substances 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- AEYHIZZYMFAUNU-UHFFFAOYSA-N 2-(3,4-dihydro-2h-pyridin-1-yl)-1h-indole Chemical class C1CCC=CN1C1=CC2=CC=CC=C2N1 AEYHIZZYMFAUNU-UHFFFAOYSA-N 0.000 abstract 1
- LQNYZAQTPONBOP-UHFFFAOYSA-N 5-chloro-3-(1-propyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indole;hydrochloride Chemical compound Cl.C1N(CCC)CCC(C=2C3=CC(Cl)=CC=C3NC=2)=C1 LQNYZAQTPONBOP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- RANMHKQOJANPJJ-UHFFFAOYSA-N 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1C1=CCNCC1 RANMHKQOJANPJJ-UHFFFAOYSA-N 0.000 description 4
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- 239000002274 desiccant Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- CIRSPTXGPFAXRE-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C1NCCC(C=2C3=CC=CC=C3NC=2)=C1 CIRSPTXGPFAXRE-UHFFFAOYSA-N 0.000 description 2
- GGSPQXPXRCIWOT-UHFFFAOYSA-N 6-methoxy-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound CC=1NC2=CC(OC)=CC=C2C=1C1=CCNCC1 GGSPQXPXRCIWOT-UHFFFAOYSA-N 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 230000003542 behavioural effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
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- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- RMCDUNHIVVEEDD-UHFFFAOYSA-N methylcyclopropane Chemical compound [CH2]C1CC1 RMCDUNHIVVEEDD-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
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- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7914979A FR2458550A1 (fr) | 1979-06-12 | 1979-06-12 | Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7914979A FR2458550A1 (fr) | 1979-06-12 | 1979-06-12 | Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2458550A1 true FR2458550A1 (fr) | 1981-01-02 |
| FR2458550B1 FR2458550B1 (enExample) | 1982-01-29 |
Family
ID=9226469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7914979A Granted FR2458550A1 (fr) | 1979-06-12 | 1979-06-12 | Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2458550A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE34299E (en) * | 1985-04-10 | 1993-06-29 | H. Lundbeck A/S | 1-(4'-fluorophenyl)-3,5-substituted indoles useful in the treatment of psychic disorders and pharmaceutical compositions thereof |
| US5468767A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antidepressant 3-(aminocycloalkenyl)-indole-5-nitrile derivatives |
| US5468768A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antimigraine derivatives of indolylcycloalkanylamines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2227873A1 (enExample) * | 1973-05-04 | 1974-11-29 | Boehringer Sohn Ingelheim |
-
1979
- 1979-06-12 FR FR7914979A patent/FR2458550A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2227873A1 (enExample) * | 1973-05-04 | 1974-11-29 | Boehringer Sohn Ingelheim |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/75 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE34299E (en) * | 1985-04-10 | 1993-06-29 | H. Lundbeck A/S | 1-(4'-fluorophenyl)-3,5-substituted indoles useful in the treatment of psychic disorders and pharmaceutical compositions thereof |
| US5468767A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antidepressant 3-(aminocycloalkenyl)-indole-5-nitrile derivatives |
| US5468768A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antimigraine derivatives of indolylcycloalkanylamines |
| US5583149A (en) * | 1994-01-06 | 1996-12-10 | Bristol-Myers Squibb Company | Antimigraine derivatives of indolylcycloalkanylamines |
| US5607961A (en) * | 1994-01-06 | 1997-03-04 | Bristol-Myers Squibb Company | Antidepressant 3-(aminocycloalkenyl)-indole-5-nitrile derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2458550B1 (enExample) | 1982-01-29 |
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