ATE351T1 - PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT. - Google Patents

PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT.

Info

Publication number
ATE351T1
ATE351T1 AT79103473T AT79103473T ATE351T1 AT E351 T1 ATE351 T1 AT E351T1 AT 79103473 T AT79103473 T AT 79103473T AT 79103473 T AT79103473 T AT 79103473T AT E351 T1 ATE351 T1 AT E351T1
Authority
AT
Austria
Prior art keywords
acid addition
optical isomer
phenylalkylaminoaethylsalicylamide
derivative
preparation
Prior art date
Application number
AT79103473T
Other languages
German (de)
Inventor
Elijah Herman Gold
Wei Chang
Original Assignee
Schering Corporation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Schering Corporation filed Critical Schering Corporation
Application granted granted Critical
Publication of ATE351T1 publication Critical patent/ATE351T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The (R,R) optical isomer of labetalol, namely 5-[ (R)-1-hydroxy- 2-[(R)-1-methyl- 3-phenylpropyl)amino ]ethyl]salicylamide, and its pharmaceutically acceptable acid addition salts, in a state substantially free of the corresponding (R,S), (S,R) and (S,S) optical isomers, are novel compounds with favourable therapeutic properties in comparison with labetalol. They can be used in particular in the treatment of hypertension. The novel (R,R) optical isomer and its pharmaceutically acceptable acid addition salts can be prepared by removal of the protecting groups from an N,O-protected (R,R) optical isomer or acid addition salt thereof, wherein the basic nitrogen atom and the phenolic hydroxy group are protected, preferably by hydrogenolytic removal of hydrogenolysable groups.
AT79103473T 1978-09-20 1979-09-17 PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT. ATE351T1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94451678A 1978-09-20 1978-09-20
EP79103473A EP0009702B1 (en) 1978-09-20 1979-09-17 A phenylalkylaminoethylsalicylamide, its preparation and pharmaceutical compositions containing it

Publications (1)

Publication Number Publication Date
ATE351T1 true ATE351T1 (en) 1981-11-15

Family

ID=25481553

Family Applications (1)

Application Number Title Priority Date Filing Date
AT79103473T ATE351T1 (en) 1978-09-20 1979-09-17 PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT.

Country Status (27)

Country Link
EP (1) EP0009702B1 (en)
JP (3) JPS5555147A (en)
KR (2) KR830000904A (en)
AT (1) ATE351T1 (en)
AU (1) AU528626B2 (en)
CA (1) CA1151211A (en)
CY (1) CY1175A (en)
DD (1) DD150457A5 (en)
DE (1) DE2961263D1 (en)
DK (1) DK387579A (en)
FI (1) FI792884A (en)
GR (1) GR73179B (en)
HK (1) HK13383A (en)
HU (1) HU185523B (en)
IE (1) IE49301B1 (en)
IL (1) IL58258A (en)
KE (1) KE3283A (en)
MY (1) MY8500042A (en)
NO (1) NO149660C (en)
NZ (1) NZ191589A (en)
OA (1) OA06339A (en)
PH (1) PH16794A (en)
PL (1) PL129114B1 (en)
PT (1) PT70191A (en)
SG (1) SG283G (en)
YU (1) YU227379A (en)
ZA (1) ZA794872B (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4658060A (en) * 1982-04-26 1987-04-14 Schering Corporation Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-phenylpropyl)aminoethyl) salicylamide
IT1194406B (en) * 1983-09-27 1988-09-22 Scharper S P A PROCEDURE FOR THE PREPARATION OF 2-HYDROXY-5-01-HYDROXY-2 - ((4-FENYL-2-BUTYL) AMINO) ETHYL BENZAMIDE
HU190867B (en) * 1984-01-20 1986-11-28 Egyt Gyogyszervegyeszeti Gyar,Hu Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof
US4788183A (en) * 1987-11-30 1988-11-29 Schering Corporation Method for treatment of dyslipidemia in humans
US4879233A (en) * 1989-02-10 1989-11-07 Schering Corporation Novel Aspergillus niveus microorganism used for the chiral reduction of carbonyl groups
KR100251995B1 (en) * 1991-08-23 2000-06-01 젠센 제임스 유. Calcium receptor active molecules
US6313146B1 (en) 1991-08-23 2001-11-06 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US5763569A (en) * 1991-08-23 1998-06-09 The Brigham And Women's Hospital, Inc Calcium receptor-active molecules
US6031003A (en) * 1991-08-23 2000-02-29 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6011068A (en) * 1991-08-23 2000-01-04 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US5688938A (en) * 1991-08-23 1997-11-18 The Brigham & Women's Hospital, Inc. Calcium receptor-active molecules
US5858684A (en) * 1991-08-23 1999-01-12 The Brigham And Women's Hospital, Inc. Method of screening calcium receptor-active molecules
US6001884A (en) * 1991-08-23 1999-12-14 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US5962314A (en) * 1993-02-23 1999-10-05 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
EP1275635A1 (en) 1994-10-21 2003-01-15 Nps Pharmaceuticals, Inc. Calcium receptor-active compounds
ATE352537T1 (en) 1996-05-01 2007-02-15 Nps Pharma Inc COMPOUNDS ACTING ON INORGANIC ION RECEPTORS
IT1313583B1 (en) * 1999-07-30 2002-09-09 Chiesi Farma Spa 2-AMINOTETRALINIC DERIVATIVES FOR GLAUCOMA THERAPY.
DK1961735T3 (en) * 2007-02-22 2010-03-29 Indena Spa Process for Preparation of (2R, 3S) -3-Phenylisoserine Methyl Ester Acetate Salt
EP2603215A4 (en) 2010-08-11 2015-08-05 Philadelphia Health & Educatio Novel d3 dopamine receptor agonists to treat dyskinesia in parkinson's disease

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012444A (en) * 1969-07-08 1977-03-15 Allen & Hanburys Limited 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof
GB1266058A (en) * 1969-07-08 1972-03-08
JPS51128937A (en) * 1975-04-17 1976-11-10 Scherico Ltd Diastereomer of phenylaminoethanol derivatives

Also Published As

Publication number Publication date
PL218408A1 (en) 1980-09-08
AU5088179A (en) 1980-03-27
MY8500042A (en) 1985-12-31
EP0009702A1 (en) 1980-04-16
IL58258A0 (en) 1979-12-30
DK387579A (en) 1980-03-21
CA1151211A (en) 1983-08-02
KR830000904A (en) 1983-04-28
JPS59108749A (en) 1984-06-23
JPH02167253A (en) 1990-06-27
DE2961263D1 (en) 1982-01-14
GR73179B (en) 1984-02-14
ZA794872B (en) 1980-11-26
KR840005307A (en) 1984-11-05
KE3283A (en) 1983-05-13
CY1175A (en) 1983-06-10
HU185523B (en) 1985-02-28
HK13383A (en) 1983-04-29
JPH0210128B2 (en) 1990-03-06
PL129114B1 (en) 1984-03-31
OA06339A (en) 1981-06-30
IE49301B1 (en) 1985-09-18
DD150457A5 (en) 1981-09-02
YU227379A (en) 1983-06-30
NZ191589A (en) 1984-03-30
KR890001998B1 (en) 1989-06-07
NO149660B (en) 1984-02-20
FI792884A (en) 1980-03-21
EP0009702B1 (en) 1981-11-04
PT70191A (en) 1979-10-01
JPS5555147A (en) 1980-04-22
PH16794A (en) 1984-02-28
AU528626B2 (en) 1983-05-05
SG283G (en) 1983-09-16
IL58258A (en) 1984-01-31
NO792993L (en) 1980-03-21
NO149660C (en) 1984-05-30
IE791770L (en) 1980-03-20

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Legal Events

Date Code Title Description
UEP Publication of translation of european patent specification
REN Ceased due to non-payment of the annual fee