GB1192219A - Improvements in or relating to Aminoalcohols and the Manufacture thereof - Google Patents
Improvements in or relating to Aminoalcohols and the Manufacture thereofInfo
- Publication number
- GB1192219A GB1192219A GB57139/67A GB5713967A GB1192219A GB 1192219 A GB1192219 A GB 1192219A GB 57139/67 A GB57139/67 A GB 57139/67A GB 5713967 A GB5713967 A GB 5713967A GB 1192219 A GB1192219 A GB 1192219A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- give
- compound
- treatment
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
1,192,219. Aminoalcohols. UPJOHN CO. 15 Dec., 1967 [6 Jan., 1967], No. 57139/67. Heading C2C. Novel compounds of formula wherein n is 1-4; R 1 is H, C 1-6 alkyl, C 5-8 cycloalkyl, phenyl, substituted phenyl, benzyl, C 2-6 hydroxyalkyl, or C 2-6 alkoxyalkyl; R 2 is H, C 1-6 alkyl, benzyl or acyl of a hydrocarbon carboxylic acid with 2-12 carbon atoms; R<SP>1</SP>, R<SP>11</SP> and R<SP>111</SP> are H, halo, C 1-6 alkyl, C 1-6 alkoxy, or -CF 3 ; and R is H, C 1-6 alkyl or acyl as defined above, pharmaceutically acceptable acid addition salts, N-oxides and quaternary alkyl ammonium halide salts of the tertiary amino derivatives of Formula I wherein the alkyl group of the alkyl halide has 1-12 carbon atoms are prepared by: heating a diketo compound of Formula II with an amine HNR 3 (R 4 ) in the presence of an acid catalyst to give a compound of Formula III and hydrogenating this compound catalytically to give the aminoalcohol of Formula I, where R is H, followed where desired by treatment with a C 1-6 alkanol to give the ether of Formula I where R is alkyl, by treatment with a suitable acid anhydride or acid halide to give the ester of Formula I where R is acyl, by treatment of the alcohol, ether or ester with a peracid to give the N oxide or by treatment of a tertiary amino compound of Formula I to give the quaternary ammonium salt. Intermediates isolated are the compounds of Formula II which are prepared by reacting the appropriate cycloalkanone with pyrrolidine, morpholine or piperidine to give the appropriate 1 - pyrrolidino, 1 - morpholino or 1 - piperidino cycloalkene, followed by reaction of this compound with the appropriate benzoyl chloride and purification by formation of a copper complex. Pharmaceutical compositions comprise a compound I in association with a suitable carrier, are administered orally or parenterally and exhibit respiratory stimulating effects. Electrocardiographic jellies contain a quaternary alkyl ammonium halide of a compound I in a gelatinous base.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60762767A | 1967-01-06 | 1967-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1192219A true GB1192219A (en) | 1970-05-20 |
Family
ID=24433054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB57139/67A Expired GB1192219A (en) | 1967-01-06 | 1967-12-15 | Improvements in or relating to Aminoalcohols and the Manufacture thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3499033A (en) |
| BE (1) | BE709004A (en) |
| CH (1) | CH513809A (en) |
| DE (1) | DE1668798A1 (en) |
| FR (1) | FR1583191A (en) |
| GB (1) | GB1192219A (en) |
| NL (1) | NL6717720A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574445A (en) * | 2020-06-19 | 2020-08-25 | 湖北精瑜材料有限公司 | Water-soluble vulcanized dimer quinoline quaternary ammonium salt corrosion inhibitor and preparation method and application thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098904A (en) * | 1976-11-12 | 1978-07-04 | The Upjohn Company | Analgesic n-(2-aminocycloaliphatic)benzamides |
| US4179501A (en) * | 1976-11-12 | 1979-12-18 | The Upjohn Company | Analgesic N-(2-aminocycloaliphatic)azidobenzamides |
| US4540690A (en) * | 1982-02-09 | 1985-09-10 | The Upjohn Company | 2-(Phenylmethylene)cycloalkylamines and -azetidines |
| US4652559A (en) * | 1982-08-16 | 1987-03-24 | The Upjohn Company | 2-(Phenylmethylene)cycloalkyl-azetidines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2854483A (en) * | 1954-10-06 | 1958-09-30 | American Home Prod | Bronchodilator compounds |
| US3252996A (en) * | 1962-10-02 | 1966-05-24 | Ciba Geigy Corp | Alpha-pyrrolidinomethyl valero and caprophenones |
-
1967
- 1967-01-06 US US607627A patent/US3499033A/en not_active Expired - Lifetime
- 1967-12-15 GB GB57139/67A patent/GB1192219A/en not_active Expired
- 1967-12-22 CH CH1803967A patent/CH513809A/en not_active IP Right Cessation
- 1967-12-28 NL NL6717720A patent/NL6717720A/xx unknown
-
1968
- 1968-01-04 DE DE19681668798 patent/DE1668798A1/en active Pending
- 1968-01-05 FR FR1583191D patent/FR1583191A/fr not_active Expired
- 1968-01-05 BE BE709004D patent/BE709004A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574445A (en) * | 2020-06-19 | 2020-08-25 | 湖北精瑜材料有限公司 | Water-soluble vulcanized dimer quinoline quaternary ammonium salt corrosion inhibitor and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6717720A (en) | 1968-07-08 |
| CH513809A (en) | 1971-10-15 |
| FR1583191A (en) | 1969-10-24 |
| BE709004A (en) | 1968-07-05 |
| DE1668798A1 (en) | 1971-09-02 |
| US3499033A (en) | 1970-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |