AU2010276490B2 - Enantio- and stereo-specific syntheses of beta-amino-alpha- hydroxy amides - Google Patents

Enantio- and stereo-specific syntheses of beta-amino-alpha- hydroxy amides Download PDF

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Publication number
AU2010276490B2
AU2010276490B2 AU2010276490A AU2010276490A AU2010276490B2 AU 2010276490 B2 AU2010276490 B2 AU 2010276490B2 AU 2010276490 A AU2010276490 A AU 2010276490A AU 2010276490 A AU2010276490 A AU 2010276490A AU 2010276490 B2 AU2010276490 B2 AU 2010276490B2
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AU
Australia
Prior art keywords
formula
compound
acid
preparing
alkyl
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.)
Ceased
Application number
AU2010276490A
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English (en)
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AU2010276490A1 (en
Inventor
Jennifer Albaneze-Walker
Ashok Arasappan
Frank Bennett
Stephane L. Bogen
Yonggang Chen
Patrice Demonchaux
Amadeo Ferreira
Thomas J. Hunter
Jianshe Kong
Shen-Chun Kuo
Azzeddine Lekhal
William W. Leong
Hongbiao Liao
Kenneth S. Matthews
Steven P. Miller
F. George Njoroge
Marc Poirier
Randi M. Smith
John Traverse
Scott T. Trzaska
Lijun Wang
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 & Dohme LLC
Original Assignee
Merck Sharp and Dohme Ltd
Merck Sharp & Dohme LLC
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
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Application filed by Merck Sharp and Dohme Ltd, Merck Sharp & Dohme LLC filed Critical Merck Sharp and Dohme Ltd
Publication of AU2010276490A1 publication Critical patent/AU2010276490A1/en
Assigned to MERCK SHARP & DOHME CORP. reassignment MERCK SHARP & DOHME CORP. Alteration of Name(s) of Applicant(s) under S113 Assignors: SCHERING CORPORATION
Application granted granted Critical
Publication of AU2010276490B2 publication Critical patent/AU2010276490B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Pulmonology (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU2010276490A 2009-07-29 2010-07-27 Enantio- and stereo-specific syntheses of beta-amino-alpha- hydroxy amides Ceased AU2010276490B2 (en)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
US22961809P 2009-07-29 2009-07-29
US22965209P 2009-07-29 2009-07-29
US22963609P 2009-07-29 2009-07-29
US22961309P 2009-07-29 2009-07-29
US22964809P 2009-07-29 2009-07-29
US61/229,618 2009-07-29
US61/229,652 2009-07-29
US61/229,648 2009-07-29
US61/229,636 2009-07-29
US61/229,613 2009-07-29
PCT/US2010/043356 WO2011014494A1 (en) 2009-07-29 2010-07-27 ENANTIO- AND STEREO-SPECIFIC SYNTHESES OF β-AMINO-α- HYDROXY AMIDES

Publications (2)

Publication Number Publication Date
AU2010276490A1 AU2010276490A1 (en) 2012-03-08
AU2010276490B2 true AU2010276490B2 (en) 2013-11-14

Family

ID=42753493

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2010276490A Ceased AU2010276490B2 (en) 2009-07-29 2010-07-27 Enantio- and stereo-specific syntheses of beta-amino-alpha- hydroxy amides

Country Status (12)

Country Link
US (1) US8680294B2 (enExample)
EP (1) EP2459525B1 (enExample)
JP (1) JP2013500971A (enExample)
CN (1) CN102639492A (enExample)
AR (1) AR077506A1 (enExample)
AU (1) AU2010276490B2 (enExample)
CA (1) CA2768838A1 (enExample)
EA (1) EA022038B1 (enExample)
GE (1) GEP20207101B (enExample)
IN (1) IN2012DN00346A (enExample)
SG (1) SG178115A1 (enExample)
WO (1) WO2011014494A1 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UY37592A (es) 2017-02-06 2018-08-31 Gilead Sciences Inc Compuestos inhibidores del vih
CN115160205B (zh) * 2022-07-08 2024-06-07 上海皓鸿生物医药科技有限公司 一种制备(s)-1-(叔丁氧羰基)-2,5-二氢-1h-吡咯-2-羧酸及盐的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005087731A1 (en) * 2004-02-27 2005-09-22 Schering Corporation Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease
WO2005097301A1 (ja) * 2004-04-07 2005-10-20 K.I Chemical Industry Co., Ltd. 硫化水素、メルカプタン等の硫化物の除去方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4825129B2 (ja) 2003-06-17 2011-11-30 シェーリング コーポレイション （１ｒ，２ｓ，５ｓ）−６，６−ジメチル−３−アザビシクロ［３，１，０］ヘキサン−２−カルボキシレートまたはその塩の調製のためのプロセスおよび中間体
WO2007138928A1 (ja) * 2006-05-26 2007-12-06 Kaneka Corporation 光学活性３－アミノ－２－ヒドロキシプロピオン酸シクロプロピルアミド誘導体およびその塩の製造方法
DE102006059317A1 (de) * 2006-07-04 2008-01-10 Evonik Degussa Gmbh Verfahren zur Herstellung von β-Amino-α-hydroxy-carbonsäureamiden

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005087731A1 (en) * 2004-02-27 2005-09-22 Schering Corporation Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease
WO2005097301A1 (ja) * 2004-04-07 2005-10-20 K.I Chemical Industry Co., Ltd. 硫化水素、メルカプタン等の硫化物の除去方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Arasappan, A. et al "Discovery of Narlaprevir (SCH 900518): A Potent, Second Generation HCV NS3 Serine Protease Inhibitor" ACS Medicinal Chemistry Letters (2010), 1(2), 64-69 *

Also Published As

Publication number Publication date
JP2013500971A (ja) 2013-01-10
CN102639492A (zh) 2012-08-15
CA2768838A1 (en) 2011-02-03
AR077506A1 (es) 2011-08-31
EA201270223A1 (ru) 2012-07-30
EP2459525B1 (en) 2017-03-01
GEAP202012594A (en) 2020-01-27
AU2010276490A1 (en) 2012-03-08
US20120178942A1 (en) 2012-07-12
EP2459525A1 (en) 2012-06-06
GEP20207101B (en) 2020-05-11
SG178115A1 (en) 2012-03-29
EA022038B1 (ru) 2015-10-30
WO2011014494A1 (en) 2011-02-03
US8680294B2 (en) 2014-03-25
IN2012DN00346A (enExample) 2015-05-08

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FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired