IE36107L - Pharmaceutical compositions; indole derivatives - Google Patents
Pharmaceutical compositions; indole derivativesInfo
- Publication number
- IE36107L IE36107L IE711465A IE146571A IE36107L IE 36107 L IE36107 L IE 36107L IE 711465 A IE711465 A IE 711465A IE 146571 A IE146571 A IE 146571A IE 36107 L IE36107 L IE 36107L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- oxide
- pyridyl
- reacting
- hydrolysing
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title abstract 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001204 N-oxides Chemical class 0.000 abstract 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000002466 imines Chemical class 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
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- BZFGKBQHQJVAHS-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C(F)(F)F)=C1 BZFGKBQHQJVAHS-UHFFFAOYSA-N 0.000 abstract 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- -1 4-pyridinecarboxylic acid halide Chemical class 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 150000004658 ketimines Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1318300 Indole-derived ketones and ketimines LABAZ 22 Nov 1971 [9 Dec 1970] 58543/70 Heading C2C The invention comprises compounds of formula and their pharmaceutically acceptable acid addition salts, wherein R 1 is H, C 1-4 alkyl, cyclohexyl or Ph (possibly p-Cl, F or MeO- substituted); R 2 , R 5 are each H or C 1-4 alkyl; R 3 is H, C 1-4 alkyl, Cl or MeO; R 4 is H, C 1-4 alkyl or Cl; R 6 is O or NH; and R 7 is 2-, 3- or 4-pyridyl (or their N-oxides), provided that (a) when R 6 is O, R 7 is pyridyl-N-oxide, and (b) when R 6 is NH, R 2 ... R 5 are each H and R 7 is pyridyl, R 1 is not Me. The imines are prepared by reacting the corresponding 3-unsubstituted indole (II) with 2-, 3- or 4-cyanopyridine or its N-oxide. The ketones are prepared by (i) forming the imine as just described, followed by hydrolysis; (ii) reacting II with a 2-, 3- or 4- pyridinecarboxylic acid dialkylamide (N-oxide) in presence of a Lewis Acid, and hydrolysing the complex so formed; (iii) reacting II-organo-Mg derivative with a 2-, 3- or 4-pyridinecarboxylic acid halide (N-oxide), and hydrolysing the complex so formed. Pharmaceutical and veterinary compositions for treating inflammation or combatting intravascular thrombosis comprise the above compounds (but the proviso does not apply), and may be administered orally, parenterally, rectally or topically.
[GB1318300A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5854370 | 1970-12-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36107L true IE36107L (en) | 1972-06-09 |
| IE36107B1 IE36107B1 (en) | 1976-08-18 |
Family
ID=10481862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1465/71A IE36107B1 (en) | 1970-12-09 | 1971-11-19 | Indole derivatives and compositions containing the same |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5133910B1 (en) |
| AT (2) | AT319229B (en) |
| AU (1) | AU452586B2 (en) |
| BE (1) | BE775487A (en) |
| CA (1) | CA956638A (en) |
| CH (1) | CH532596A (en) |
| DK (1) | DK136367B (en) |
| ES (1) | ES397787A1 (en) |
| FI (1) | FI55509C (en) |
| FR (1) | FR2117878B1 (en) |
| GB (1) | GB1318300A (en) |
| HU (1) | HU166730B (en) |
| IE (1) | IE36107B1 (en) |
| NL (1) | NL153774B (en) |
| NO (1) | NO137549C (en) |
| OA (1) | OA03929A (en) |
| SE (1) | SE390305B (en) |
| YU (1) | YU34519B (en) |
| ZA (1) | ZA717857B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59145847U (en) * | 1983-03-18 | 1984-09-29 | 三菱自動車工業株式会社 | Reclining adjuster mounting bracket |
| CN108239083B (en) * | 2016-12-26 | 2021-08-17 | 阿里根公司 | Aromatic hydrocarbon receptor modulators |
| EP3713937A2 (en) | 2017-11-20 | 2020-09-30 | Ariagen, Inc. | Indole compounds as aryl hydrocarbon receptor (ahr) modulators |
| IL287177B2 (en) | 2019-04-15 | 2026-04-01 | Ariagen Inc | Chiral indole-based thiazole derivatives and their use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL100127C (en) * | 1954-04-28 | |||
| US3517020A (en) * | 1967-11-01 | 1970-06-23 | Sandoz Ag | Certain 1-(3'-nicotinoyl)-2-loweralkylthio-benzimidazoles |
| US3557142A (en) * | 1968-02-20 | 1971-01-19 | Sterling Drug Inc | 4,5,6,7-tetrahydro-indole-lower-alkanoic acids and esters |
-
1970
- 1970-12-09 GB GB5854370A patent/GB1318300A/en not_active Expired
-
1971
- 1971-11-18 BE BE775487A patent/BE775487A/en not_active IP Right Cessation
- 1971-11-19 IE IE1465/71A patent/IE36107B1/en unknown
- 1971-11-22 ZA ZA717857A patent/ZA717857B/en unknown
- 1971-11-24 FR FR7142006A patent/FR2117878B1/fr not_active Expired
- 1971-11-24 SE SE7115067A patent/SE390305B/en unknown
- 1971-11-25 YU YU2981/71A patent/YU34519B/en unknown
- 1971-11-26 AU AU36229/71A patent/AU452586B2/en not_active Expired
- 1971-11-29 CH CH1734771A patent/CH532596A/en not_active IP Right Cessation
- 1971-11-29 NL NL717116360A patent/NL153774B/en not_active IP Right Cessation
- 1971-12-08 NO NO4526/71A patent/NO137549C/en unknown
- 1971-12-08 CA CA129,677A patent/CA956638A/en not_active Expired
- 1971-12-08 DK DK601371AA patent/DK136367B/en not_active IP Right Cessation
- 1971-12-09 HU HULA785A patent/HU166730B/hu unknown
- 1971-12-09 FI FI3512/71A patent/FI55509C/en active
- 1971-12-09 OA OA54437A patent/OA03929A/en unknown
- 1971-12-09 ES ES397787A patent/ES397787A1/en not_active Expired
- 1971-12-09 AT AT173173A patent/AT319229B/en not_active IP Right Cessation
- 1971-12-09 JP JP46100058A patent/JPS5133910B1/ja active Pending
- 1971-12-09 AT AT1061171A patent/AT312594B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL153774B (en) | 1977-07-15 |
| FR2117878A1 (en) | 1972-07-28 |
| DE2160017B2 (en) | 1976-02-19 |
| AT319229B (en) | 1974-12-10 |
| JPS5133910B1 (en) | 1976-09-22 |
| BE775487A (en) | 1972-05-18 |
| SE390305B (en) | 1976-12-13 |
| ZA717857B (en) | 1972-08-30 |
| FI55509C (en) | 1979-08-10 |
| IE36107B1 (en) | 1976-08-18 |
| NL7116360A (en) | 1972-06-13 |
| AU3622971A (en) | 1973-05-31 |
| DK136367C (en) | 1978-02-27 |
| FI55509B (en) | 1979-04-30 |
| HU166730B (en) | 1975-05-28 |
| CH532596A (en) | 1973-01-15 |
| DK136367B (en) | 1977-10-03 |
| NO137549B (en) | 1977-12-05 |
| OA03929A (en) | 1975-08-14 |
| AT312594B (en) | 1974-01-10 |
| NO137549C (en) | 1978-03-15 |
| ES397787A1 (en) | 1975-04-16 |
| AU452586B2 (en) | 1974-09-05 |
| FR2117878B1 (en) | 1974-10-18 |
| YU298171A (en) | 1979-02-28 |
| CA956638A (en) | 1974-10-22 |
| YU34519B (en) | 1979-09-10 |
| GB1318300A (en) | 1973-05-23 |
| DE2160017A1 (en) | 1972-06-22 |
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