WO2009042094A3 - Hiv protease inhibitors - Google Patents

Hiv protease inhibitors Download PDF

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Publication number
WO2009042094A3
WO2009042094A3 PCT/US2008/010972 US2008010972W WO2009042094A3 WO 2009042094 A3 WO2009042094 A3 WO 2009042094A3 US 2008010972 W US2008010972 W US 2008010972W WO 2009042094 A3 WO2009042094 A3 WO 2009042094A3
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
protease inhibitors
hiv protease
prophylaxis
formula
Prior art date
Application number
PCT/US2008/010972
Other languages
French (fr)
Other versions
WO2009042094A2 (en
Inventor
Craig A Coburn
Joseph P Vacca
Hemaka A Rajapakse
Kristen L G Jones
Philippe Nantermet
James C Barrow
Keith P Moore
Cory Theberge
Abbas M Walji
Original Assignee
Merck & Co Inc
Craig A Coburn
Joseph P Vacca
Hemaka A Rajapakse
Kristen L G Jones
Philippe Nantermet
James C Barrow
Keith P Moore
Cory Theberge
Abbas M Walji
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 Merck & Co Inc, Craig A Coburn, Joseph P Vacca, Hemaka A Rajapakse, Kristen L G Jones, Philippe Nantermet, James C Barrow, Keith P Moore, Cory Theberge, Abbas M Walji filed Critical Merck & Co Inc
Publication of WO2009042094A2 publication Critical patent/WO2009042094A2/en
Publication of WO2009042094A3 publication Critical patent/WO2009042094A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/41—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • AIDS & HIV (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Compounds of Formula A are disclosed: (A), wherein XA, k, R1, R2, R3, R4, R5, R5A, R6 and R7 are defined herein. The compounds encompassed by Formula A include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
PCT/US2008/010972 2007-09-25 2008-09-22 Hiv protease inhibitors WO2009042094A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US99520207P 2007-09-25 2007-09-25
US60/995,202 2007-09-25
US18872008P 2008-08-12 2008-08-12
US61/188,720 2008-08-12

Publications (2)

Publication Number Publication Date
WO2009042094A2 WO2009042094A2 (en) 2009-04-02
WO2009042094A3 true WO2009042094A3 (en) 2009-07-30

Family

ID=40329420

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/010972 WO2009042094A2 (en) 2007-09-25 2008-09-22 Hiv protease inhibitors

Country Status (2)

Country Link
TW (1) TW201006475A (en)
WO (1) WO2009042094A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2632895B1 (en) * 2010-10-28 2018-10-03 Merck Canada Inc. Hiv protease inhibitors
US9187415B2 (en) 2010-10-29 2015-11-17 Merck Canada Inc. Sulfonamides as HIV protease inhibitors
EP2771332B1 (en) 2011-10-26 2016-06-29 Merck Canada Inc. Thiophen and thiazol sulfonamid derivatives as HIV protease inhibitors for the treatment of AIDS
US9315475B2 (en) 2012-09-11 2016-04-19 Merck Sharp & Dohme Corp. HIV protease inhibitors
WO2015013835A1 (en) 2013-07-31 2015-02-05 Merck Sharp & Dohme Corp. Piperazine derivatives as hiv protease inhibitors
EP3083609B1 (en) 2013-12-19 2018-08-15 Merck Sharp & Dohme Corp. Hiv protease inhibitors
WO2015095276A1 (en) 2013-12-19 2015-06-25 Merck Sharp & Dohme Corp. Hiv protease inhibitors
US10138255B2 (en) 2014-03-10 2018-11-27 Merck Sharp & Dohme Corp. Piperazine derivatives as HIV protease inhibitors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008077070A2 (en) * 2006-12-18 2008-06-26 University Of Massachusetts Crystal structures of hiv-1 protease inhibitors bound to hiv-1 protease

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008077070A2 (en) * 2006-12-18 2008-06-26 University Of Massachusetts Crystal structures of hiv-1 protease inhibitors bound to hiv-1 protease

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
NALAM MADHAVI N L ET AL: "Crystal structure of lysine sulfonamide inhibitor reveals the displacement of the conserved flap water molecule in human immunodeficiency virus type 1 protease", JOURNAL OF VIROLOGY, THE AMERICAN SOCIETY FOR MICROBIOLOGY, US, vol. 81, no. 17, 1 September 2007 (2007-09-01), pages 9512 - 9518, XP002482672, ISSN: 0022-538X *
STRANIX B R ET AL: "Lysine sulfonamides as novel HIV-protease inhibitors: Nepsilon-Acyl aromatic alpha-amino acids", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 16, no. 13, 1 July 2006 (2006-07-01), pages 3459 - 3462, XP025107392, ISSN: 0960-894X, [retrieved on 20060701] *

Also Published As

Publication number Publication date
WO2009042094A2 (en) 2009-04-02
TW201006475A (en) 2010-02-16

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