AU2399884A - Preparing n-alkylated amino acids and esters thereof - Google Patents

Preparing n-alkylated amino acids and esters thereof

Info

Publication number
AU2399884A
AU2399884A AU23998/84A AU2399884A AU2399884A AU 2399884 A AU2399884 A AU 2399884A AU 23998/84 A AU23998/84 A AU 23998/84A AU 2399884 A AU2399884 A AU 2399884A AU 2399884 A AU2399884 A AU 2399884A
Authority
AU
Australia
Prior art keywords
optionally substituted
carbon atoms
radical
cycloaliphatic
aliphatic radical
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.)
Granted
Application number
AU23998/84A
Other versions
AU566053B2 (en
Inventor
Rainer Henning
Hansjorg Urbach
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Aventis Pharma Deutschland GmbH
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 Aventis Pharma Deutschland GmbH filed Critical Aventis Pharma Deutschland GmbH
Publication of AU2399884A publication Critical patent/AU2399884A/en
Application granted granted Critical
Publication of AU566053B2 publication Critical patent/AU566053B2/en
Assigned to AVENTIS PHARMA DEUTSCHLAND GMBH reassignment AVENTIS PHARMA DEUTSCHLAND GMBH Alteration of Name(s) in Register under S187 Assignors: HOECHST A.G.
Anticipated expiration legal-status Critical
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

For the Contracting states : BE, CH, DE, FR, GB, IT, LU, NL, SE 1. A process for preparing compounds of the formula I see diagramm : EP0117448,P21,F1 in which n = 1 or 2, R denotes, hydrogen, carboxy, carbamoyl, an optionally substituted aliphatic radical having 2-8 carbon atoms, an optionally substituted cycloaliphatic radical having 3-9 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms, an OR**4 or SR**4 radical in which R**4 represents an optionally substituted aliphatic radical having 1-4 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms or an optionally substituted heteroaromatic radical having 5-10 ring atoms, or an optionally substituted heteroaromatic radical having 5-10 ring atoms, R**1 denotes hydrogen, an optionally substituted aliphatic radical having 1-6 carbon atoms, an optionally substituted cycloaliphatic radical having 3-9 carbon atoms, an optionally substituted cycloaliphatic-aliphatic radical having 4-13 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms, an optionally substituted araliphatic radical having 7-16 carbon atoms, an optionally substituted heteroaromatic radical having 5-10 ring atoms or the side chain of an optionally protected naturally occuring alpha-amino acid, R**2 and R**3 are identical or different and denote hydrogen, an optionally substituted aliphatic radical having 1-6 carbon atoms, an optionally substituted cycloaliphatic radical having 3-9 carbon atoms, an optionally substituted cycloaliphatic-aliphatic radical having 4-12 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms or an optionally substituted araliphatic radical having 7-16 carbon atoms, which comprises reacting compounds of the formulae II ou III see diagramm : EP0117448,P22,F2 in which n, R, R**1, R**2 and R**3 have the abovementioned meanings, with compounds of the formulae IV or V see diagramm : EP0117448,P22,F3 in which R, R**1, R**2, R**3 and n have the abovementioned meanings, if desired eliminating ester groups by hydrolysis or if desired esterifying free carboxyl groups in a manner known per se. For the Contracting state : Austria 1. A process for preparing compounds of the formula see diagramm : EP0117448,P25,F1 in which n = 1 or 2, R denotes, carbamoyl, hydrogen, carboxy an optionally substituted aliphatic radical having 2-8 carbon atoms, an optionally substituted cycloaliphatic radical having 3-9 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms, an OR**4 or SR**4 radical in which R**4 represents an optionally substituted aliphatic radical having 1-4 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms or an optionally substituted heteroaromatic radical having 5-10 ring atoms, or an optionally substituted heteroaromatic radical having 5-10 ring atoms, R**1 denotes hydrogen, an optionally substituted aliphatic radical having 1-6 carbon atoms, an optionally substituted cycloaliphatic radical having 3-9 carbon atoms, an optionally substituted cycloaliphatic-aliphatic radical having 4-13 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms, an optionally substituted araliphatic radical having 7-16 carbon atoms, an optionally substituted heteroaromatic radical having 5-10 ring atoms or the side chain of an optionally protected naturally accuring alpha-amino acid, R**2 and R**3 are identical or different and denote hydrogen, an optionally substituted aliphatic radical having 1-6 carbon atoms, an optionally substituted cycloaliphatic radical having 3-9 carbon atoms, an optionally substituted cycloaliphatic-aliphatic radical having 4-12 carbon atoms, an optionally substituted aromatic radical having 6-12 carbon atoms or an optionally substituted araliphatic radical having 7-16 carbon atoms, which comprises reacting compounds of the formulae II or III see diagramm : EP0117448,P26,F2 in which n, R, R**1, R**2 and R**3 have the abovementioned meanings, with compounds of the formulae IV or V see diagramm : EP0117448,P26,F3 in which R, R**1, R**2, R**3 and n have the abovementioned meanings, if desired eliminating ester groups by hydrolysis or hydrogenolysis or if desired esterifying free carboxyl groups in a manner known per se.
AU23998/84A 1983-02-02 1984-02-01 Preparing n-alkylated amino acids and esters thereof Expired AU566053B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19833303344 DE3303344A1 (en) 1983-02-02 1983-02-02 METHOD FOR PRODUCING N-ALKYLATED AMINO ACIDS AND THEIR ESTERS
DE3303344 1983-02-02

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU78304/87A Division AU588483B2 (en) 1983-02-02 1987-09-11 Trifluoromethanesulfonyloxy derivatives

Publications (2)

Publication Number Publication Date
AU2399884A true AU2399884A (en) 1984-08-09
AU566053B2 AU566053B2 (en) 1987-10-08

Family

ID=6189750

Family Applications (2)

Application Number Title Priority Date Filing Date
AU23998/84A Expired AU566053B2 (en) 1983-02-02 1984-02-01 Preparing n-alkylated amino acids and esters thereof
AU78304/87A Expired AU588483B2 (en) 1983-02-02 1987-09-11 Trifluoromethanesulfonyloxy derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU78304/87A Expired AU588483B2 (en) 1983-02-02 1987-09-11 Trifluoromethanesulfonyloxy derivatives

Country Status (14)

Country Link
EP (1) EP0117448B1 (en)
JP (2) JPS59172442A (en)
KR (1) KR910008135B1 (en)
AT (1) ATE21890T1 (en)
AU (2) AU566053B2 (en)
CA (2) CA1292236C (en)
DE (2) DE3303344A1 (en)
DK (2) DK166619C (en)
ES (1) ES529302A0 (en)
GR (1) GR79751B (en)
IE (1) IE56751B1 (en)
IL (1) IL70847A (en)
PT (1) PT78047B (en)
ZA (1) ZA84740B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3648935A (en) * 1970-02-04 1972-03-14 Amchem Prod Spray apparatus with movable head
DE3303344A1 (en) * 1983-02-02 1984-08-02 Hoechst Ag, 6230 Frankfurt METHOD FOR PRODUCING N-ALKYLATED AMINO ACIDS AND THEIR ESTERS
US4801721A (en) * 1984-08-16 1989-01-31 Ryan James W Stereospecific synthesis of carboxyalkyl peptides
DE3431591A1 (en) * 1984-08-28 1986-03-13 Diamalt AG, 8000 München METHOD FOR PRODUCING AMINO COMPOUNDS FROM HYDROXYL COMPOUNDS
JPS63170344A (en) * 1987-01-09 1988-07-14 Daicel Chem Ind Ltd N-alkylation of amino acid ester
JP2535001B2 (en) * 1987-01-13 1996-09-18 ダイセル化学工業株式会社 Process for producing N-alkylated amino acid ester
FR2620699B1 (en) * 1987-09-17 1990-06-01 Adir PROCESS FOR THE SYNTHESIS OF ALPHA AMINO N ALKYL ACIDS AND THEIR ESTERS. APPLICATION TO THE SYNTHESIS OF CARBOXYALKYL DIPEPTIDES
US5055588A (en) * 1988-07-06 1991-10-08 Daicel Chemical Industries Ltd. Process for preparing N-substituted amino acid esters
SE0000382D0 (en) 2000-02-07 2000-02-07 Astrazeneca Ab New process
CN1585744A (en) 2001-03-27 2005-02-23 兰贝克赛实验室有限公司 Process for the preparation of benazepril
WO2008032463A1 (en) * 2006-09-12 2008-03-20 Wako Pure Chemical Industries, Ltd. Process for production of sulfonic acid ester
HUE040323T2 (en) 2012-12-21 2019-02-28 Epizyme Inc Prmt5 inhibitors and uses thereof

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3419595A (en) * 1965-03-05 1968-12-31 Minnesota Mining & Mfg Fluorocarbon fluoroalkanesulfonates
NL144484B (en) * 1967-07-26 1975-01-15 Merck & Co Inc PROCESS FOR THE PREPARATION OF A MEDICINAL PRODUCT WITH ANTI-ANFLAMMATORY ACTION AND A PROCESS FOR THE PREPARATION OF THE ANTI-INFLAMMATORY ACTIVE ARALKYL MERCAPTOAMINO ACIDS.
GB1572185A (en) * 1975-10-25 1980-07-23 Beecham Group Ltd Intermediates for the preparation of 12-azaprostaglandins
DE2937779A1 (en) 1979-09-19 1981-04-09 Hoechst Ag, 6000 Frankfurt AMINO ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
DE3044236A1 (en) 1980-11-25 1982-06-16 Hoechst Ag, 6000 Frankfurt AMINO ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
FR2487829A2 (en) 1979-12-07 1982-02-05 Science Union & Cie NOVEL SUBSTITUTED IMINO ACIDS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS AN ENZYME INHIBITOR
FR2503155A2 (en) 1980-10-02 1982-10-08 Science Union & Cie NOVEL SUBSTITUTED IMINO DIACIDES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS AN ENZYME INHIBITOR
US4350704A (en) 1980-10-06 1982-09-21 Warner-Lambert Company Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids
IE52663B1 (en) 1980-04-02 1988-01-20 Warner Lambert Co Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids
DE3177130D1 (en) 1980-08-30 1990-01-11 Hoechst Ag AMINO ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, MEANS CONTAINING THEM AND THE USE THEREOF.
US4344949A (en) 1980-10-03 1982-08-17 Warner-Lambert Company Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids
FR2492381A1 (en) 1980-10-21 1982-04-23 Science Union & Cie NOVEL AZA BICYCLO ALKANE CARBOXYLIC ACIDS SUBSTITUTED IN THEIR PREPARATION METHODS AND THEIR USE AS AN ENZYME INHIBITOR
DE19575012I2 (en) 1980-10-23 2002-01-24 Schering Corp Carboxyalkyl dipeptides Process for their preparation and medicaments containing them
US4374847A (en) 1980-10-27 1983-02-22 Ciba-Geigy Corporation 1-Carboxyalkanoylindoline-2-carboxylic acids
DE3226768A1 (en) 1981-11-05 1983-05-26 Hoechst Ag, 6230 Frankfurt DERIVATIVES OF CIS, ENDO-2-AZABICYCLO- (3.3.0) -OCTAN-3-CARBONIC ACID, METHOD FOR THE PRODUCTION THEREOF, THE MEANS CONTAINING THEM AND THE USE THEREOF
DE3151690A1 (en) 1981-12-29 1983-07-07 Hoechst Ag, 6230 Frankfurt Novel derivatives of bicyclic amino acids, process for their preparation, compositions containing them and their use, and also novel bicyclic amino acids as intermediates and process for their preparation
DE3210496A1 (en) 1982-03-23 1983-10-06 Hoechst Ag NEW DERIVATIVES OF BICYCLIC AMINO ACIDS, METHOD FOR THE PRODUCTION THEREOF, THE MEANS CONTAINING THEM AND THE USE THEREOF, AND NEW BICYCLIC AMINO ACIDS AS INTERMEDIATE STAGES AND METHOD FOR THE PRODUCTION THEREOF
DE3211397A1 (en) 1982-03-27 1983-11-10 Hoechst Ag, 6230 Frankfurt SPIRO (4. (3 + N)) - 2-AZA-3-CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THE MEANS CONTAINING THEM AND THEIR USE
DE3211676A1 (en) 1982-03-30 1983-10-06 Hoechst Ag NEW DERIVATIVES OF CYCLOALKA (C) PYRROL CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF, THEIR SUBSTANCES AND THE USE THEREOF AND NEW CYCLOALKA (C) PYRROL CARBONIC ACIDS AS THE INTERMEDIATE LEVELS AND METHODS
DE3227055A1 (en) 1982-07-20 1984-01-26 Hoechst Ag, 6230 Frankfurt NEW DERIVATIVES OF 2-AZA-BICYCLO (2.2.2) OCTAN-3-CARBONIC ACID, METHOD FOR THE PRODUCTION THEREOF, THEIR SUBSTANCES AND THE USE THEREOF, AND 2-AZA-BICYCLO (2.2.2) OCTAN-3-CARBONIC ACID AS ANSWER FOR THEIR PRODUCTION
DE3242151A1 (en) 1982-11-13 1984-05-17 Hoechst Ag, 6230 Frankfurt NEW DERIVATIVES OF TRICYCLIC AMINO ACIDS, METHOD FOR THE PRODUCTION THEREOF, THEIR SUBSTANCES AND THE USE THEREOF, AND NEW BICYCLIC AMINO ACIDS AS INTERMEDIATE STAGES AND METHOD FOR THE PRODUCTION THEREOF
DE3246503A1 (en) 1982-12-16 1984-06-20 Hoechst Ag, 6230 Frankfurt DERIVATIVES OF CIS, ENDO-2-AZABICYCLO- (5.3.0) -DECAN-3-CARBONIC ACID, METHOD FOR THE PRODUCTION THEREOF, THESE AGENTS AND THE USE THEREOF
DE3246757A1 (en) 1982-12-17 1984-06-20 Hoechst Ag, 6230 Frankfurt NEW 2-AZABICYCLO (2.2.1) HEPTAN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THEIR SUBSTANCES AND THE USE THEREOF, AND 2-AZABICYCLO (2.2.1) HEPTAN DERIVATIVES AS INTERMEDIATE PRODUCTS AND METHOD FOR THE PRODUCTION THEREOF
DE3303344A1 (en) * 1983-02-02 1984-08-02 Hoechst Ag, 6230 Frankfurt METHOD FOR PRODUCING N-ALKYLATED AMINO ACIDS AND THEIR ESTERS

Also Published As

Publication number Publication date
PT78047B (en) 1986-07-15
EP0117448A1 (en) 1984-09-05
DK49492A (en) 1992-04-13
IE56751B1 (en) 1991-12-04
ES8500215A1 (en) 1984-10-01
CA1292236C (en) 1991-11-19
KR850000384A (en) 1985-02-27
EP0117448B1 (en) 1986-09-03
ES529302A0 (en) 1984-10-01
ZA84740B (en) 1984-09-26
AU7830487A (en) 1987-12-17
DK45584A (en) 1984-08-03
CA1267903A (en) 1990-04-17
JPH0587499B2 (en) 1993-12-16
DK49492D0 (en) 1992-04-13
ATE21890T1 (en) 1986-09-15
DK166619B (en) 1993-06-21
GR79751B (en) 1984-10-31
IE840244L (en) 1984-08-02
AU566053B2 (en) 1987-10-08
DK173770B1 (en) 2001-09-24
DE3460578D1 (en) 1986-10-09
JPH06102646B2 (en) 1994-12-14
KR910008135B1 (en) 1991-10-10
JPS59172442A (en) 1984-09-29
AU588483B2 (en) 1989-09-14
DE3303344A1 (en) 1984-08-02
IL70847A (en) 1991-04-15
PT78047A (en) 1984-03-01
DK45584D0 (en) 1984-02-01
IL70847A0 (en) 1984-05-31
JPH05320119A (en) 1993-12-03
DK166619C (en) 1993-11-08

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Legal Events

Date Code Title Description
PC Assignment registered

Owner name: AVENTIS PHARMA DEUTSCHLAND GMBH

Free format text: FORMER OWNER WAS: HOECHST A.G.

MK14 Patent ceased section 143(a) (annual fees not paid) or expired