GB1273653A - Derivatives of phenolic amino alcohols - Google Patents
Derivatives of phenolic amino alcoholsInfo
- Publication number
- GB1273653A GB1273653A GB32589/70A GB3258970A GB1273653A GB 1273653 A GB1273653 A GB 1273653A GB 32589/70 A GB32589/70 A GB 32589/70A GB 3258970 A GB3258970 A GB 3258970A GB 1273653 A GB1273653 A GB 1273653A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phenyl
- radical
- prepared
- alkoxy
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1,273,653. Derivatives of phenolic amino alcohols. MERCK & CO. Inc. 6 July, 1970 [10 July, 1969], No. 32589/70. Heading C2C. Novel compounds of Formula I wherein R<SP>1</SP> is H or -C : O.R or where R<SP>4</SP> is a hydrogen atom, an alkyl, cycloalkyi, alkenyl, cycloalkenyl, alkoxy, phenyl or benzyl radical, a substituted phenyl or benzyl in which the substituent(s) is/are halogen, C 1-6 alkyl, C 1-6 perfluoroalkyl, C 1-6 alkoxy, hydroxy, amino, alkylamino, dialkylamino, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, sulfamoyl, alkylsulfamoyl or phenyl, a substituted alkyl radical in which the substituent(s) is/are halogen, aryl, hydroxy, amino, C 1-6 alkoxy, carboxy or esterified carboxy, or a heterocyclic radical that is optionally substituted by C 1-6 alkyl, halogen or methoxy, and R<SP>5</SP> is a hydrogen atom or an alkyl or phenyl radical or a substituted phenyl radical in which the substituent(s) is/are halogen, C 1-6 alkyl, C 1-6 perfluoroalkyl, C 1-6 alkoxy, hydroxy, amino, alkylamino, dialkylamino, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, sulfamoyl, alkylsulfamoyl or phenyl or R<SP>4</SP> and R<SP>5</SP> are combined to form a saturated or unsaturated unsubstituted or phenyl-substituted alicyclic or heterocyclic ring; R<SP>6</SP> is a hydrogen atom or an alkyl or phenyl radical and n is 0 when R<SP>4</SP> or R<SP>5</SP> is joined to the C atom by a double bond, n otherwise being 1; X is a hydrogen or halogen atom, a hydroxy, alkoxy, alkyl or phenyl radical or a radical of formula R<SP>3</SP> is a hydrogen atom or a C 1-6 alkyl radical and each R<SP>2</SP> is a hydrogen atom, an alkyl, phenyl, benzyl, heterocyclic, cycloalkyl, alkenyl or cycloalkenyl radical, a substituted phenyl or benzyl in which the substituent(s) is/are halogen, C 1-6 alkyl, C 1-6 perfluoroalkyl, C 1-6 alkoxy, hydroxy, amino, alkylamino, dialkylamino, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, sulfamoyl, alkylsulfamoyl or phenyl or a substituted alkyl radical in which the substituent(s) is/are halogen, aryl, hydroxy, amino, C 1-6 alkoxy, carboxy or esterified carboxy, are prepared either by rearrangement under acidic conditions of a compound of Formula II wherein Z is OH or Cl, or by reaction of an acid halide or anhydride of an acid of formula R<SP>2</SP>COOH with a compound of Formula IV wherein R<SP>7</SP> is an amino blocking group which is removed after the reaction. Intermediates of Formula II above are prepared by reaction of an alcohol of Formula XII with one equivalent of a reactive derivative of R 2 COOH optionally followed by conversion of Z when OH into Z=Cl by SOCl 2 . Threo α-(1-aminoethyl)-3-hydroxybenzyl alcohol is prepared by action of hydrogen and catalyst on threo 3-benzyloxy-α-(1-dibenzylaminoethyl)- benzyl alcohol prepared by reduction of m-benzyloxy-α-dibenzylaminopropiophenone obtained by reaction of dibenzylamine with m-benzyloxy-α- bromopropiophenone, itself or prepared by action of bromine on the unhalogenated compound. Erythro α-(1-aminoethyl)-3-methoxy-6-methylbenzyl alcohol is prepared by catalytic reduction of 3-methoxy-6-methyl-α-aminopropiophenone obtained by reduction of the corresponding amine which is prepared by rearrangement of the oxime obtained from 3-methoxy-6-methylpropiophenone prepared by reaction of propionitrile and the Grignard reagent from 2-bromo-4- methoxytoluene. Pharmaceutical compositions in conventional forms for oral or parenteral administration and having antihypertensive activity and capable of inhibiting gastric secretion comprise an above novel compound and a carrier or diluent.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US84512069A | 1969-07-10 | 1969-07-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1273653A true GB1273653A (en) | 1972-05-10 |
Family
ID=25294452
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32589/70A Expired GB1273653A (en) | 1969-07-10 | 1970-07-06 | Derivatives of phenolic amino alcohols |
Country Status (14)
Country | Link |
---|---|
US (1) | US3714229A (en) |
JP (1) | JPS5220463B1 (en) |
AU (1) | AU1710070A (en) |
BE (1) | BE753237A (en) |
BR (1) | BR6914798D0 (en) |
CH (1) | CH565138A5 (en) |
DK (1) | DK138418B (en) |
ES (1) | ES381597A1 (en) |
FR (1) | FR2059503B1 (en) |
GB (1) | GB1273653A (en) |
IL (1) | IL34831A0 (en) |
NL (1) | NL7009390A (en) |
SE (1) | SE383511B (en) |
ZA (1) | ZA704157B (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4336400A (en) * | 1969-04-01 | 1982-06-22 | Sterling Drug Inc. | 3-(Hydroxy or hydroxymethyl)-4-hydroxy-alpha(aminomethyl)benzyl alcohols and methods of use |
US4138581A (en) * | 1969-04-01 | 1979-02-06 | Sterling Drugs Inc. | 3(Hydroxy or hydroxymethyl)-4(hydroxy)-α-(aminomethyl)benzyl alcohols |
GB1346401A (en) * | 1971-05-12 | 1974-02-13 | Lepetit Spa | Cardioactive arylaminobutanols |
US3928426A (en) * | 1972-01-28 | 1975-12-23 | Robins Co Inc A H | 1-Cyclopropyl-1-phenyl-omega-amino-1-lower alkanoyloxyalkanes |
US4001429A (en) * | 1974-04-01 | 1977-01-04 | A. H. Robins Company, Incorporated | 1-Cyclopropyl-1-phenyl-ω-amino-1-alkanols and 1-lower-alkylacyl derivatives as analgetics |
JPS556625B2 (en) * | 1974-05-16 | 1980-02-18 | ||
JPS52171571U (en) * | 1976-06-16 | 1977-12-27 | ||
JPS53114564U (en) * | 1977-02-16 | 1978-09-12 | ||
DE2817494A1 (en) * | 1977-05-03 | 1978-11-09 | Continental Pharma | AMINO ALCOHOL DERIVATIVE |
JPS6210048A (en) * | 1985-07-04 | 1987-01-19 | Microbial Chem Res Found | Novel physiologically active substance mh435 |
US5220063A (en) * | 1991-05-10 | 1993-06-15 | Hoechst Celanese Corporation | Method for the preparation of arylalkanolacylamides |
CN116332774A (en) * | 2023-03-29 | 2023-06-27 | 成都瑞尔医药科技有限公司 | Preparation method of high chiral purity meta-hydroxylamine bitartrate |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2442797A (en) * | 1943-10-05 | 1948-06-08 | Sharp & Dohme Inc | Para-amino benzoic acid esters |
FR1537803A (en) * | 1966-07-14 | 1968-08-30 | Diwag Chemische Fabriken Gmbh | Process for making acylaminophenolalkanols |
-
1969
- 1969-07-10 US US00845120A patent/US3714229A/en not_active Expired - Lifetime
- 1969-12-05 BR BR214798/69A patent/BR6914798D0/en unknown
-
1970
- 1970-06-18 ZA ZA704157A patent/ZA704157B/en unknown
- 1970-06-25 NL NL7009390A patent/NL7009390A/xx unknown
- 1970-07-01 IL IL34831A patent/IL34831A0/en unknown
- 1970-07-02 AU AU17100/70A patent/AU1710070A/en not_active Expired
- 1970-07-06 GB GB32589/70A patent/GB1273653A/en not_active Expired
- 1970-07-08 CH CH1033670A patent/CH565138A5/xx not_active IP Right Cessation
- 1970-07-09 ES ES381597A patent/ES381597A1/en not_active Expired
- 1970-07-09 BE BE753237D patent/BE753237A/en unknown
- 1970-07-09 SE SE7009536A patent/SE383511B/en unknown
- 1970-07-09 DK DK358870AA patent/DK138418B/en unknown
- 1970-07-10 JP JP45060028A patent/JPS5220463B1/ja active Pending
- 1970-07-10 FR FR707025768A patent/FR2059503B1/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US3714229A (en) | 1973-01-30 |
ES381597A1 (en) | 1973-04-16 |
CH565138A5 (en) | 1975-08-15 |
ZA704157B (en) | 1972-01-26 |
DE2034139A1 (en) | 1971-02-04 |
BE753237A (en) | 1971-01-11 |
DK138418C (en) | 1979-02-12 |
JPS5220463B1 (en) | 1977-06-03 |
FR2059503A1 (en) | 1971-06-04 |
DK138418B (en) | 1978-09-04 |
NL7009390A (en) | 1971-01-12 |
AU1710070A (en) | 1972-01-06 |
IL34831A0 (en) | 1970-09-17 |
FR2059503B1 (en) | 1973-07-13 |
SE383511B (en) | 1976-03-15 |
BR6914798D0 (en) | 1973-03-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |