CA2041620A1 - An ortho-lithiation process for the synthesis of 2-substituted-1-(tetrazol-5-yl) benzenes - Google Patents

An ortho-lithiation process for the synthesis of 2-substituted-1-(tetrazol-5-yl) benzenes

Info

Publication number
CA2041620A1
CA2041620A1 CA002041620A CA2041620A CA2041620A1 CA 2041620 A1 CA2041620 A1 CA 2041620A1 CA 002041620 A CA002041620 A CA 002041620A CA 2041620 A CA2041620 A CA 2041620A CA 2041620 A1 CA2041620 A1 CA 2041620A1
Authority
CA
Canada
Prior art keywords
tetrazol
synthesis
substituted
ortho
benzenes
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
CA002041620A
Other languages
French (fr)
Other versions
CA2041620C (en
Inventor
Richard F. Shuman
Anthony O. King
Robert K. Anderson
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.)
Merck Sharp and Dohme LLC
Original Assignee
Merck and Co Inc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24061644&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2041620(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of CA2041620A1 publication Critical patent/CA2041620A1/en
Application granted granted Critical
Publication of CA2041620C publication Critical patent/CA2041620C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (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)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Battery Electrode And Active Subsutance (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

A process utilizes the tetrazole functional group to direct lithiation at the ortho position of a phenyltetrazole and generate a nucleophilic aryllithium species which then undergoes reaction with an electrophile to generate a 2-substituted 1-(tetrazol-5-yl)benzene. The process is useful in the production of intermediates in the synthesis of angiotensin II antagonists. This novel process is a more cost effective and versatile route for the large-scale preparation of these key intermediates.
CA002041620A 1990-05-02 1991-05-01 An ortho-lithiation process for the synthesis of 2-substituted-1-(tetrazol-5-yl) benzenes Expired - Lifetime CA2041620C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/517,889 US5039814A (en) 1990-05-02 1990-05-02 Ortho-lithiation process for the synthesis of 2-substituted 1-(tetrazol-5-yl)benzenes
US517,889 1990-05-02

Publications (2)

Publication Number Publication Date
CA2041620A1 true CA2041620A1 (en) 1991-11-03
CA2041620C CA2041620C (en) 2003-03-11

Family

ID=24061644

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002041620A Expired - Lifetime CA2041620C (en) 1990-05-02 1991-05-01 An ortho-lithiation process for the synthesis of 2-substituted-1-(tetrazol-5-yl) benzenes

Country Status (15)

Country Link
US (1) US5039814A (en)
EP (1) EP0455423B1 (en)
JP (1) JPH0717619B2 (en)
AT (1) ATE146461T1 (en)
CA (1) CA2041620C (en)
CY (1) CY1998A (en)
DE (1) DE69123632T2 (en)
DK (1) DK0455423T3 (en)
ES (1) ES2095907T3 (en)
GR (1) GR3022107T3 (en)
HK (1) HK59497A (en)
IE (1) IE911455A1 (en)
LV (1) LV11893B (en)
PT (1) PT97528B (en)
RO (1) RO110339B1 (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5616599A (en) * 1991-02-21 1997-04-01 Sankyo Company, Limited Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use
US5283242A (en) * 1991-10-24 1994-02-01 American Home Products Corporation Substituted benzimidazoles and quinazolines as antihypertensives
US5256654A (en) * 1991-10-24 1993-10-26 American Home Products Corporation Substituted pyrrolopyrimidines, azepinopyrimidines and pyridopyrimidines useful as angiotensin II antagonists
US5149699A (en) * 1991-10-24 1992-09-22 American Home Products Corporation Substituted pyridopyrimidines useful as antgiotensin II antagonists
US5252753A (en) * 1991-11-01 1993-10-12 Ortho Pharmaceutical Corporation Process for the preparation of certain substituted biphenyl tetrazoles and compounds thereof
ES2203614T3 (en) * 1991-11-18 2004-04-16 E.I. Du Pont De Nemours And Company TETRAZOLILPHENILBORONIC ACID INTERMEDIATES FOR SYNTHESIS OF ANTAGONISTS OF AII RECEIVERS.
US5206374A (en) * 1991-11-18 1993-04-27 E. I. Du Pont De Nemours And Company Process for preparing tetrazolylphenylboronic acid intermediates
EP0550313A1 (en) * 1991-12-30 1993-07-07 Synthelabo 2-(Tetranol-5-yl)-(1,1'-biphenyl)derivatives, their preparation and use as intermediates
FR2688503B1 (en) * 1992-03-16 1994-05-06 Synthelabo PROCESS FOR THE PREPARATION OF 2- (TETRAZOL-5-YL) - [1,1'-BIPHENYL] DERIVATIVES.
FR2696746B1 (en) * 1992-10-12 1994-11-18 Synthelabo Benzeneborinic acid derivatives, their preparation and their use as synthesis intermediates.
FR2696745B1 (en) * 1992-10-12 1995-05-12 Synthelabo Process for the preparation of phenyltetrazole derivatives.
HU219598B (en) * 1992-12-17 2001-05-28 Sankyo Co. Ltd. Imidazole- and pyridine derivatives of biphenyl compounds, process for producing them and pharmaceutical compositions containing them
US5567815A (en) * 1994-07-18 1996-10-22 Bridgestone Corporation Teritary amine containing antonic initiators used in preparing polymers and process for the preparation thereof
WO1996009301A1 (en) * 1994-09-20 1996-03-28 Wakunaga Seiyaku Kabushiki Kaisha Process for producing n-biphenylmethylthiadiazoline derivative or salt thereof and intermediate for producing the same
KR100354802B1 (en) * 1994-10-20 2002-12-26 한국화학연구원 Process for preparing tetrazole derivatives
US5760220A (en) * 1995-06-07 1998-06-02 American Home Products Corporation Process for preparation of biphenyl derivatives
JPH11507625A (en) * 1995-06-07 1999-07-06 アメリカン・ホーム・プロダクツ・コーポレイション Method for producing biphenyl derivative
IT1292437B1 (en) 1997-06-30 1999-02-08 Zambon Spa ORTHO-METALLATION PROCESS USEFUL FOR THE SYNTHESIS OF 1 - TETRAZOL- 5-IL) 2-SUBSTITUTED BENZENES
ES2264641B1 (en) * 2005-06-17 2008-03-01 Quimica Sintetica, S.A. PROCEDURE FOR OBTAINING DERIVATIVES OF BENCIMIDAZOL AND ITS INTERMEDIATES.
JP2010510177A (en) 2006-11-17 2010-04-02 クイーンズ ユニバーシティ アット キングストン Compounds and methods for treating protein folding disorders
EP3287434A1 (en) 2007-12-17 2018-02-28 United Therapeutics Corporation Process to prepare treprostinil, the active ingredient in remodulin ®
EP2576492B1 (en) 2010-06-03 2017-09-20 United Therapeutics Corporation Treprostinil production
JP5580491B2 (en) 2011-03-02 2014-08-27 ユナイテッド セラピューティクス コーポレイション Synthesis of intermediates for the production of treprostinil.
US9593061B2 (en) 2014-10-20 2017-03-14 United Therapeutics Corporation Synthesis of intermediates for producing prostacyclin derivatives

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3534113A (en) * 1968-02-08 1970-10-13 Lithium Corp Preparation of aryllithium compounds by metalation
CH531511A (en) * 1969-03-05 1972-12-15 Sandoz Ag Process for the preparation of the N, o-dilithium derivative of 2-phenyl-2-imidazoline
US4620025A (en) * 1984-08-01 1986-10-28 Merck & Co., Inc. Process for the preparation of biphenyl intermediates
US4820843A (en) * 1987-05-22 1989-04-11 E. I. Du Pont De Nemours And Company Tetrazole intermediates to antihypertensive compounds
US4870186A (en) * 1987-05-22 1989-09-26 E. I. Du Pont De Nemours And Company Tetrazole intermediates to antihypertensive compounds
CA1338238C (en) * 1988-01-07 1996-04-09 David John Carini Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids

Also Published As

Publication number Publication date
DE69123632T2 (en) 1997-05-15
CY1998A (en) 1997-12-05
JPH0717619B2 (en) 1995-03-01
US5039814A (en) 1991-08-13
LV11893A (en) 1997-12-20
PT97528A (en) 1992-01-31
HK59497A (en) 1997-05-16
JPH04225966A (en) 1992-08-14
DK0455423T3 (en) 1997-06-09
CA2041620C (en) 2003-03-11
PT97528B (en) 1998-08-31
ATE146461T1 (en) 1997-01-15
LV11893B (en) 1998-03-20
RO110339B1 (en) 1995-12-29
EP0455423B1 (en) 1996-12-18
DE69123632D1 (en) 1997-01-30
IE911455A1 (en) 1991-11-06
ES2095907T3 (en) 1997-03-01
GR3022107T3 (en) 1997-03-31
EP0455423A3 (en) 1992-12-09
EP0455423A2 (en) 1991-11-06

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