AU533863B2 - Indole derivatives with pharmacological properties - Google Patents
Indole derivatives with pharmacological propertiesInfo
- Publication number
- AU533863B2 AU533863B2 AU59153/80A AU5915380A AU533863B2 AU 533863 B2 AU533863 B2 AU 533863B2 AU 59153/80 A AU59153/80 A AU 59153/80A AU 5915380 A AU5915380 A AU 5915380A AU 533863 B2 AU533863 B2 AU 533863B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- carbon atoms
- radical containing
- compound
- submitted
- 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.)
- Ceased
Links
- 150000002475 indoles Chemical class 0.000 title abstract 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 28
- 150000001875 compounds Chemical class 0.000 abstract 28
- -1 alkyl radical Chemical class 0.000 abstract 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 16
- 239000003795 chemical substances by application Substances 0.000 abstract 13
- 125000005843 halogen group Chemical group 0.000 abstract 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 6
- 238000003776 cleavage reaction Methods 0.000 abstract 6
- 150000003254 radicals Chemical class 0.000 abstract 6
- 230000007017 scission Effects 0.000 abstract 6
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 4
- 208000005156 Dehydration Diseases 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 3
- 125000003386 piperidinyl group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- BBQQULRBTOMLTC-UHFFFAOYSA-N 1-benzylpiperidin-3-one Chemical compound C1C(=O)CCCN1CC1=CC=CC=C1 BBQQULRBTOMLTC-UHFFFAOYSA-N 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002734 organomagnesium group Chemical group 0.000 abstract 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 abstract 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
- C07D401/04—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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
For the Contracting States : BE, CH, LI, DE, FR, GB, IT, LU, NL, SE 1. Compounds with the formula (I) : see diagramm : EP0021924,P23,F1 in which : - R represents a hydrogen atom, an alkyl radical containing from 1 to 8 carbon atoms or an aralkyl radical containing from 7 to 12 carbon atoms. - X represents a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms, - Y represents a hydrogen atom or a halogen atom, - Z represents a hydrogen atom, an alkyl or hydroalkyl radical containing from 1 to 8 carbon atoms, an aryloxyalkyl radical containing from 7 to 12 carbon atoms, an aralkyl radical containing from 7 to 12 carbon atoms possibly substituted by one or more halogen atoms, by one or more alkoxy radicals containing from 1 to 4 carbon atoms, by one or more alkyl radicals containing from 1 to 4 carbon atoms, or by one or more radicals OH, CF3 , OCF3 , NO2 or NH2 or Z represents a cycloalkyl-alkyl radical containing from 4 to 12 carbon atoms, an alkenyl radical containing from 3 to 8 carbon atoms or an alkynyl radical containing from 3 to 8 carbon atoms and, - either a and b each represent a hydrogen atom, - or a represents a hydrogen atom and b represents a hydroxyl radical or an alkoxy radical containing from 1 to 8 carbon atoms, - or a and b together form a double carbon-carbon bond as well as the salts of addition with acids of the compounds with the formula (I). For the Contracting State : AT 1. Process for the preparation of compounds with the formula (I) : see diagramm : EP0021924,P25,F1 in which : - R represents a hydrogen atom, an alkyl radical containing from 1 to 8 carbon atoms or an aralkyl radical containing from 7 to 12 carbon atoms, - X represents a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms, - Y represents a hydrogen atom or a halogen atom, - Z represents a hydrogen atom, an alkyl or hydroalkyl radical containing from 1 to 8 carbon atoms, an aryloxyalkyl radical containing from 7 to 12 carbon atoms, an aralkyl radical containing from 7 to 12 carbon atoms possibly substituted by one or more halogen atoms, by one or more alkoxy radicals containing from 1 to 4 carbon atoms, by one or more alkyl radicals containing from 1 to 4 carbon atoms, or by one or more radicals OH, CF3 , OCF3 , NO2 or NH2 or Z represents a cycloalkyl-alkyl radical containing from 4 to 12 carbon atoms, an alkenyl radical containing from 3 to 8 carbon atoms or an alkynyl radical containing from 3 to 8 carbon atoms and, - either a and b each represent a hydrogen atom, - or a represents a hydrogen atom and b represents a hydroxyl radical or an alkoxy radical containing from 1 to 8 carbon atoms, - or a and b together form a double carbon-carbon bond as well as the salts of addition with acids characterized in that a compound with the formula (I). see diagramm : EP0021924,P25,F2 in which X represents a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms and Hal represents a halogen atom is submitted to the action of an alkylation or aralkylation agent, so as to obtain a compound with the formula (III) : see diagramm : EP0021924,P25,F3 in which R' represents an alkyl radical containing from 1 to 8 carbon atoms or an aralkyl radical containing from 7 to 12 carbon atoms, which is converted into an organo-magnesium derivative, so as to obtain a compound with the formula (IV) : see diagramm : EP0021924,P25,F4 which is condensed with N-benzyl 3-piperidone, so as to obtain a compound with the formula (IA ) : see diagramm : EP0021924,P26,F5 then, if desired - either the compound with the formula (IA ) is submitted to the action of a dehydratation agent, so as to obtain a compound with the formula (IB ) : see diagramm : EP0021924,P26,F6 which if desired, in the case where R' represents a benzyl radical is submitted to the action of a selective cleavage agent for the benzyl group carried by the nucleus of the indole, so as to obtain a compound with formula (IC ) : see diagramm : EP0021924,P26,F7 which, if desired, is submitted to the action of a cleavage agent for the benzyl group carried by the tetrahydropyridinyl nucleus, so as to obtain the compound of the formula (ID ) : see diagramm : EP0021924,P26,F8 - or the compound with the formula (IA ) is submitted to the action of a cleavage agent for the benzyl group carried by the nitrogen of the piperidinyl group, so as to obtain a compound with the formula (IE ) : see diagramm : EP0021924,P26,F9 which if desired is submitted to the action of a dehydratation agent, so as to obtain a compound with the formula (IF ) : see diagramm : EP0021924,P26,F10 - or, in the case where R' represents a benzyl group the compound with the formula (IA ) is submitted to the action of a selective cleavage agent for the benzyl group carried by the indole nucleus, so as to obtain a compound with the formula (IG ) : see diagramm : EP0021924,P26,F11 which, if desired, is submitted to the action of a cleavage agent for the benzyl group carried by the piperidinyl nucleus so as to obtain a compound with the formula (IH ) : see diagramm : EP0021924,P26,F12 then, if desired, each of the compounds obtained which respond to the formula (I) in which Z represents a hydrogen atom is submitted to the action of an agent able to introduce a radical Z', Z' having the same significante as Z, set out in claim 1, with the exception of hydrogen, so as to obtain the corresponding compounds with the formula (I) in which the nitrogen atom of the piperidinyl nucleus carries a radical Z' and, if desired, - either each of the compounds obtained responding to the formula (I) in which b represents a hydroxyl radical is submitted to the action of an etherification agent, so as to obtain the corresponding compounds with the formula (I) in which b represents an alkoxy radical containing from 1 to 8 carbon atoms, - or each of the compounds obtained responding to the formula (I) in which b represents a hydroxyl radical is submitted to the action of a dehydratation agent, so as to obtain the corresponding compounds with the formula (I) in which a and b together form a double carbon-carbon bond, - or each of the compounds obtained responding to the formula (I) in which b represents a hydroxyl radical, is submitted to the action of a cleavage agent for the hydroxyl group, so as to obtain the corresponding compounds with the formula (I) in which a and b each represent a hydrogen atom and, if desired each of the compounds with the formula (I) so obtained is submitted to the action of a halogenation agent able to introduce a halogen atom Hal in position 3 of the indole, so as to obtain the corresponding compound with the formula (I) in which Y represents a halogen atom, and if desired, each of the compounds with the formula (I) previously obtained is submitted to the action of an acid so as to form its salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7914976A FR2458549A1 (en) | 1979-06-12 | 1979-06-12 | NOVEL INDOLE DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS |
| FR7914976 | 1979-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5915380A AU5915380A (en) | 1980-12-18 |
| AU533863B2 true AU533863B2 (en) | 1983-12-15 |
Family
ID=9226466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU59153/80A Ceased AU533863B2 (en) | 1979-06-12 | 1980-06-09 | Indole derivatives with pharmacological properties |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0021924B1 (en) |
| JP (1) | JPS5636480A (en) |
| AT (1) | ATE2790T1 (en) |
| AU (1) | AU533863B2 (en) |
| CA (1) | CA1150265A (en) |
| DE (1) | DE3062331D1 (en) |
| DK (1) | DK186880A (en) |
| ES (1) | ES492321A0 (en) |
| FR (1) | FR2458549A1 (en) |
| HU (1) | HU184785B (en) |
| IE (1) | IE49906B1 (en) |
| PT (1) | PT71372B (en) |
| ZA (1) | ZA803217B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2492824A2 (en) * | 1980-10-24 | 1982-04-30 | Roussel Uclaf | 4-Piperidinyl indole derivs. - with dopaminergic activity e.g. for treating Parkinsons disease and excessive prolactin secretion |
| FR2486081A2 (en) * | 1979-06-12 | 1982-01-08 | Roussel Uclaf | 4-Piperidinyl 1H-indole minus isomer - prepd. by resolving racemic mixt. with D minus tartaric acid |
| FR2510111A1 (en) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | NOVEL DERIVATIVES OF PIPERIDIN-3-YL INDOLE, THEIR SALTS, PROCESS FOR PREPARING THEM, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THEM |
| FR2510112A1 (en) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | NOVEL DERIVATIVES OF 2-OXO-PYRID-3-YL OR PIPERIDIN-3-YL INDOLE, THEIR SALTS, PREPARATION METHOD, MEDICAMENT APPLICATION AND COMPOSITIONS COMPRISING THE SAME |
| FR2567884B1 (en) * | 1984-07-19 | 1987-03-06 | Roussel Uclaf | NEW INDOLE DERIVATIVES, THEIR PREPARATION, THEIR APPLICATION AS MEDICAMENTS AND THE COMPOSITIONS CONTAINING THEM |
| FR2578846B1 (en) * | 1985-03-12 | 1987-05-22 | Roussel Uclaf | 7-HYDROXY INDOLE DERIVATIVES, THEIR SALTS, PREPARATION PROCESS, APPLICATION AS MEDICAMENTS, COMPOSITIONS CONTAINING AND INTERMEDIATES |
| FR2610929B1 (en) * | 1987-02-13 | 1989-06-23 | Roussel Uclaf | BENZIMIDAZOL-2-ONE DERIVATIVES, SALTS THEREOF, PROCESS FOR PREPARATION, APPLICATION AS MEDICAMENTS, COMPOSITIONS CONTAINING AND INTERMEDIATES |
| EP0398413A1 (en) * | 1989-05-16 | 1990-11-22 | Duphar International Research B.V | "3,4-dehydropiperidine derivatives having psychotropic activity |
| TW222631B (en) * | 1991-07-15 | 1994-04-21 | Duphar Int Res |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1030623A (en) * | 1962-01-17 | 1966-05-25 | Upjohn Co | 3-substituted-indoles and their preparation |
| US3290332A (en) * | 1965-08-30 | 1966-12-06 | American Cyanamid Co | 6, 7-dihydroindoles and derivatives thereof |
| US3501484A (en) * | 1968-01-15 | 1970-03-17 | Miles Lab | Certain substituted 3 - (2-indolyl)-1,2,5,6-tetrahydropyridines and derivatives thereof |
| FR2391211A2 (en) * | 1977-05-18 | 1978-12-15 | Roussel Uclaf | Antihypertensive 2-indolyl:piperidinyl-1-benzo-dioxanyl ethanol cpds. - which are prepd. from indolyl:piperidine cpd. and oxiranyl benzodioxan |
-
1979
- 1979-06-12 FR FR7914976A patent/FR2458549A1/en active Granted
-
1980
- 1980-04-30 DK DK186880A patent/DK186880A/en not_active Application Discontinuation
- 1980-05-29 ZA ZA00803217A patent/ZA803217B/en unknown
- 1980-06-06 EP EP80400808A patent/EP0021924B1/en not_active Expired
- 1980-06-06 DE DE8080400808T patent/DE3062331D1/en not_active Expired
- 1980-06-06 AT AT80400808T patent/ATE2790T1/en active
- 1980-06-09 AU AU59153/80A patent/AU533863B2/en not_active Ceased
- 1980-06-11 ES ES492321A patent/ES492321A0/en active Granted
- 1980-06-11 JP JP7792380A patent/JPS5636480A/en active Granted
- 1980-06-11 HU HU801469A patent/HU184785B/en not_active IP Right Cessation
- 1980-06-11 PT PT71372A patent/PT71372B/en unknown
- 1980-06-11 CA CA000353814A patent/CA1150265A/en not_active Expired
- 1980-06-11 IE IE1207/80A patent/IE49906B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8102119A1 (en) | 1980-12-16 |
| PT71372B (en) | 1981-10-21 |
| JPH0113475B2 (en) | 1989-03-06 |
| ES492321A0 (en) | 1980-12-16 |
| FR2458549B1 (en) | 1981-10-16 |
| HU184785B (en) | 1984-10-29 |
| EP0021924B1 (en) | 1983-03-16 |
| DE3062331D1 (en) | 1983-04-21 |
| FR2458549A1 (en) | 1981-01-02 |
| ATE2790T1 (en) | 1983-04-15 |
| CA1150265A (en) | 1983-07-19 |
| DK186880A (en) | 1980-12-13 |
| EP0021924A2 (en) | 1981-01-07 |
| JPS5636480A (en) | 1981-04-09 |
| IE801207L (en) | 1980-12-12 |
| IE49906B1 (en) | 1986-01-08 |
| EP0021924A3 (en) | 1981-02-18 |
| AU5915380A (en) | 1980-12-18 |
| PT71372A (en) | 1980-07-01 |
| ZA803217B (en) | 1981-05-27 |
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