GB1186938A - Tertiary 1,3-Aminoalcohols - Google Patents
Tertiary 1,3-AminoalcoholsInfo
- Publication number
- GB1186938A GB1186938A GB39082/67A GB3908267A GB1186938A GB 1186938 A GB1186938 A GB 1186938A GB 39082/67 A GB39082/67 A GB 39082/67A GB 3908267 A GB3908267 A GB 3908267A GB 1186938 A GB1186938 A GB 1186938A
- Authority
- GB
- United Kingdom
- Prior art keywords
- treating
- compound
- alkyl
- benzoyl
- appropriate
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,186,938. Tertiary 1,3-aminoalcohols. UPJOHN CO. 24 Aug., 1967 [26 Sept., 1966], No. 39082/67. Heading C2C. Novel compounds of Formula II wherein n is 1-4; -N Z is a heterocyclic radical with 5-10 atoms in the ring; R<SP>1</SP>, R<SP>11</SP> and R<SP>111</SP> are selected from hydrogen atoms, halogen atoms, C 1-6 alkyl, C 1-6 alkoxy and -CF 3 radicals; and R 1 , R 2 and R 3 are selected from hydrogen atoms, C 1-6 alkyl, C 1-6 alkoxy and -CF 3 radicals and their C 1-4 alkyl ethers, esters with C 2-8 straight-chain alkanoic acids, benzoic acid, mono-substituted benzoic acids, phenylacetic acid and phenyl-propionic acid, N-oxides, acid addition salts and quaternary C 1-12 alkyl ammonium halide salts are prepared by the following processes: (a) where the free hydroxy compound is required by treating a compound of Formula I with a Grignard reagent V wherein X is iodine or bromine, followed by decomposition of the resultant complex with water, (b) where the ether is required, by treating a compound II with sodamide in liquid ammonia followed by an alkyl bromide or iodide, (c) where the ester is required, by treating a compound I with butyl lithium and treating the salt formed with the appropriate acyl chloride, and (d) where the N-oxide is required, by treating a compound I with a peracid, followed in (a), (b), (c) or (d), where desired, by salt formation. Electrocardiographic jellies contain as the active ingredient a quaternary ammonium halide salt of compounds (II). A suitable jelly contains 5 parts glycerol, 10 parts starch, 60 parts quaternary ammonium salt and 100 parts water. The starting materials of Formula I are prepared by reacting the appropriate cycloalkanone with an heterocyclic amine to form an enamine and reacting this enamine with the appropriate benzoyl chloride, the benzoyl radical of which attaches itself to the 2-position of the cycloalkenyl moiety of the enamine. After hydrolysis the 2-(benzoyl or substituted benzoyl)-cycloalkanone is reacted with the appropriate heterocyclic amine. The thus-obtained (phenyl or substituted phenyl) (2-heterocyclicamino-1-cycloalken-1-yl) ketone is hydrogenated to give the starting material I. Pharmaceutical compositions comprise the compounds (II) and a carrier therefor. Compositions may be in a form suitable for enteral or parenteral administration and are useful in the treatment of oedema associated with hepatic disease, oedema and toxaemia of pregnancy, hypertensive vascular disease, premenstrual fluid retention and congestive heart failure.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US58173066A | 1966-09-26 | 1966-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1186938A true GB1186938A (en) | 1970-04-08 |
Family
ID=24326344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB39082/67A Expired GB1186938A (en) | 1966-09-26 | 1967-08-24 | Tertiary 1,3-Aminoalcohols |
Country Status (7)
Country | Link |
---|---|
US (1) | US3506670A (en) |
BE (1) | BE704301A (en) |
DE (1) | DE1695955A1 (en) |
FR (1) | FR1557678A (en) |
GB (1) | GB1186938A (en) |
IL (1) | IL28595A (en) |
NL (1) | NL6712786A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
FR2833004B1 (en) * | 2001-12-05 | 2004-12-10 | Aventis Pharma Sa | SUBSTITUTED ARYL-CYCLOALCANS, COMPOSITIONS CONTAINING THEM, AND USE |
CA2532286A1 (en) * | 2006-01-05 | 2007-07-05 | Seprotech Systems Incorporated | Removal of phosphates from wastewater |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3078275A (en) * | 1956-05-28 | 1963-02-19 | Upjohn Co | N, n-disubstituted-alpha-(tertiaryaminoalkyl)-alpha, alpha-diphenylacetamides |
DE1111208B (en) * | 1957-07-18 | 1961-07-20 | Hoechst Ag | Process for the production of cough-relieving, basic substituted diphenylcarbinol esters |
US3157656A (en) * | 1960-07-20 | 1964-11-17 | Olin Mathieson | Heterocyclic compounds |
GB993525A (en) * | 1961-05-19 | 1965-05-26 | Smith Kline French Lab | Substituted propanolamines and process for preparing the same |
NL63794C (en) * | 1961-10-10 |
-
1966
- 1966-09-26 US US581730A patent/US3506670A/en not_active Expired - Lifetime
-
1967
- 1967-08-24 GB GB39082/67A patent/GB1186938A/en not_active Expired
- 1967-08-25 DE DE19671695955 patent/DE1695955A1/en active Pending
- 1967-09-01 IL IL28595A patent/IL28595A/en unknown
- 1967-09-19 NL NL6712786A patent/NL6712786A/xx unknown
- 1967-09-25 FR FR1557678D patent/FR1557678A/fr not_active Expired
- 1967-09-26 BE BE704301D patent/BE704301A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
IL28595A (en) | 1971-05-26 |
FR1557678A (en) | 1969-02-21 |
DE1695955A1 (en) | 1971-05-27 |
NL6712786A (en) | 1968-03-27 |
US3506670A (en) | 1970-04-14 |
BE704301A (en) | 1968-03-26 |
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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 |