CA1267903A - Trifluoromethanesulfonates and a process for their preparation - Google Patents

Trifluoromethanesulfonates and a process for their preparation

Info

Publication number
CA1267903A
CA1267903A CA000577190A CA577190A CA1267903A CA 1267903 A CA1267903 A CA 1267903A CA 000577190 A CA000577190 A CA 000577190A CA 577190 A CA577190 A CA 577190A CA 1267903 A CA1267903 A CA 1267903A
Authority
CA
Canada
Prior art keywords
alkyl
aryl
alkenyl
amino
cycloalkyl
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 - Lifetime
Application number
CA000577190A
Other languages
French (fr)
Inventor
Hansjorg Urbach
Rainer Henning
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
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Application granted granted Critical
Publication of CA1267903A publication Critical patent/CA1267903A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth 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)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention relates to trifluoromethanesulfonates of the formulae II and III <IMG> (II) <IMG> (III) in which n = 2, R represents (C1 to C6-alkyl, (C2 to C6)-alkenyl, (C3 to C9)-cycloalkyl, (C2-C5)-acylamino-(C1- C4)-alkyl, (C7-C13)-aroylamino-(C1-C4)-alkyl, (C1-C4)-alkoxycarbonylamino-(C1-C4)-alkyl, (C6 C12)-aryl-(C1-C4)-alkoxycarbonylamino-(C1-C4)-alkyl, (C6 to C12)-aryl which can be monosubstituted, dissubstrituted or trisubstituted by one or more of (C1-C4)-alkyl, (C1 to C4)-alkoxyhydroxy, halogen, nitro, amino, (C1 to C4)-alkylamino, di-(C1 to C4)-alkylamino and methylenedioxy, or 3-indolyl, R1 represents hydrogen or (C2 to C6)-alkyl, which can be optionally substituted by amino, (C1 to C6)-acyl-amino or benzoylamino, (C2 to C6)-alkenyl, (C3 to C9)-cycloalkyl, (C5 to C9)-cycloalkenyl, (C3 to C7)-cycloalkyl-(C1 to C4)-alkyl, (C6 to C12)aryl or partially hydrogenated aryl, either of which can be substituted by (C1 to C4)-alkyl, (C1 or C2)-alkoxy or halogen, (C6 to C12)-aryl-(C2 to C4)-alkyl or (C7-C13)-aroyl-(C1-C12)-alkyl, either of which can be substituted in the aryl radical as defined above, a monocyclic or bicyclic heterocyclic radical having 5 to 7 or 8 to 10 ring atoms respectively of which 1 or 2 ring atoms represent sulfur or oxygen atoms and/or 1 to 4 ring atoms represent nitrogen atoms which can be thienyl, benzo-¢b!thienyl, furyl, pyranyl, benzofuryl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, indazolyl, isoindolyl, indolyl, purinyl, quinolizinyl, isoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolyl, cinnolinyl, pteridinyl, oxazolyl, isoxazolyl, thiazolyl or isothiazolyl, or a side chain of a naturally occurring protected .alpha.-amino acid, R2 represents hydrogen, (C1 to C6)-alkyl, (C2 to C6)-alkenyl or (C6 to C12)-aryl- (C1 to C4)alkyl, and R3 represents hydrogen, (C1 to C6)-alkyl, (C2 to (C6)-alkenyl or (C6-C12)-aryl-(C1 to C4)-alkyl and processes for their preparation. The compounds of the formula II and III are intermediates for the preparation of inhibitors of the angiotensin converting enzyme.
CA000577190A 1983-02-02 1988-09-12 Trifluoromethanesulfonates and a process for their preparation Expired - Lifetime CA1267903A (en)

Applications Claiming Priority (3)

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
DEP3303344.7 1983-02-02
CA 446562 CA1292236C (en) 1983-02-02 1984-02-01 Process for preparing n-alkylated amino acids and esters thereof

Publications (1)

Publication Number Publication Date
CA1267903A true CA1267903A (en) 1990-04-17

Family

ID=6189750

Family Applications (2)

Application Number Title Priority Date Filing Date
CA 446562 Expired - Lifetime CA1292236C (en) 1983-02-02 1984-02-01 Process for preparing n-alkylated amino acids and esters thereof
CA000577190A Expired - Lifetime CA1267903A (en) 1983-02-02 1988-09-12 Trifluoromethanesulfonates and a process for their preparation

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA 446562 Expired - Lifetime CA1292236C (en) 1983-02-02 1984-02-01 Process for preparing n-alkylated amino acids and esters thereof

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) ES8500215A1 (en)
GR (1) GR79751B (en)
IE (1) IE56751B1 (en)
IL (1) IL70847A (en)
PT (1) PT78047B (en)
ZA (1) ZA84740B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6919450B2 (en) 2001-03-27 2005-07-19 Ranbaxy Laboratories Limited Process for the preparation of benazepril
US8269038B2 (en) 2006-09-12 2012-09-18 Wako Pure Chemical Industries, Ltd. Process for production of sulfonic acid ester
US10980794B2 (en) 2012-12-21 2021-04-20 Epizyme, Inc. PRMT5 inhibitors and uses thereof

Families Citing this family (9)

* 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

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* 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
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
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
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
DE3177311D1 (en) 1980-08-30 1994-06-09 Hoechst Ag Amino acid derivatives, processes for their preparation, compositions containing them and their use.
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
ATE20469T1 (en) 1980-10-23 1986-07-15 Schering Corp CARBOXYALKYL DIPEPTIDES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICALS 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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6919450B2 (en) 2001-03-27 2005-07-19 Ranbaxy Laboratories Limited Process for the preparation of benazepril
US8269038B2 (en) 2006-09-12 2012-09-18 Wako Pure Chemical Industries, Ltd. Process for production of sulfonic acid ester
US10980794B2 (en) 2012-12-21 2021-04-20 Epizyme, Inc. PRMT5 inhibitors and uses thereof

Also Published As

Publication number Publication date
DK45584D0 (en) 1984-02-01
AU588483B2 (en) 1989-09-14
AU566053B2 (en) 1987-10-08
KR910008135B1 (en) 1991-10-10
IL70847A0 (en) 1984-05-31
CA1292236C (en) 1991-11-19
EP0117448A1 (en) 1984-09-05
EP0117448B1 (en) 1986-09-03
DK173770B1 (en) 2001-09-24
IE840244L (en) 1984-08-02
KR850000384A (en) 1985-02-27
ZA84740B (en) 1984-09-26
PT78047B (en) 1986-07-15
DE3303344A1 (en) 1984-08-02
IL70847A (en) 1991-04-15
AU2399884A (en) 1984-08-09
JPH0587499B2 (en) 1993-12-16
JPS59172442A (en) 1984-09-29
GR79751B (en) 1984-10-31
PT78047A (en) 1984-03-01
DK49492D0 (en) 1992-04-13
AU7830487A (en) 1987-12-17
DK49492A (en) 1992-04-13
ES529302A0 (en) 1984-10-01
DE3460578D1 (en) 1986-10-09
IE56751B1 (en) 1991-12-04
JPH06102646B2 (en) 1994-12-14
DK166619C (en) 1993-11-08
ATE21890T1 (en) 1986-09-15
DK45584A (en) 1984-08-03
ES8500215A1 (en) 1984-10-01
DK166619B (en) 1993-06-21
JPH05320119A (en) 1993-12-03

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