WO1994004492A1 - Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors - Google Patents

Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors Download PDF

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Publication number
WO1994004492A1
WO1994004492A1 PCT/US1993/007814 US9307814W WO9404492A1 WO 1994004492 A1 WO1994004492 A1 WO 1994004492A1 US 9307814 W US9307814 W US 9307814W WO 9404492 A1 WO9404492 A1 WO 9404492A1
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WO
WIPO (PCT)
Prior art keywords
radicals
compound
alkyl
amino
para
Prior art date
Application number
PCT/US1993/007814
Other languages
English (en)
French (fr)
Inventor
Michael L. Vazquez
Richard A. Mueller
John J. Talley
Daniel Getman
Gary A. Decrescenzo
John N. Freskos
Original Assignee
G.D. Searle & Co.
The Monsanto Company
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=25466397&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1994004492(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to KR1019950700563A priority Critical patent/KR100296463B1/ko
Priority to DK93923714T priority patent/DK0656887T3/da
Priority to EP93923714A priority patent/EP0656887B1/en
Priority to CA002140929A priority patent/CA2140929C/en
Application filed by G.D. Searle & Co., The Monsanto Company filed Critical G.D. Searle & Co.
Priority to DE69321845T priority patent/DE69321845T2/de
Priority to AU53474/94A priority patent/AU680635C/en
Priority to JP50653094A priority patent/JP3657002B2/ja
Priority to KR1020007012894A priority patent/KR100336699B1/ko
Priority to US08/204,827 priority patent/US6060476A/en
Publication of WO1994004492A1 publication Critical patent/WO1994004492A1/en
Priority to US08/294,468 priority patent/US5968942A/en
Priority to US08/586,866 priority patent/US6046190A/en
Priority to NO950533A priority patent/NO305478B1/no
Priority to FI950650A priority patent/FI112471B/fi
Priority to US08/451,090 priority patent/US6455581B1/en
Priority to NO983099A priority patent/NO307047B1/no
Priority to US09/288,080 priority patent/US6248775B1/en
Priority to US09/525,161 priority patent/US6500832B1/en
Priority to US09/798,255 priority patent/US6417387B1/en
Priority to FI20012317A priority patent/FI119427B/fi
Priority to US10/157,019 priority patent/US6646010B2/en
Priority to US10/199,481 priority patent/US6846954B2/en
Priority to US10/633,376 priority patent/US6924286B1/en
Priority to US10/812,343 priority patent/US7115618B2/en
Priority to US11/110,943 priority patent/US7141609B2/en
Priority to US11/433,797 priority patent/US7531538B2/en
Priority to US11/526,101 priority patent/US7320983B2/en
Priority to US11/788,948 priority patent/USRE43596E1/en
Priority to US11/788,947 priority patent/USRE42889E1/en
Priority to NL300283C priority patent/NL300283I1/nl
Priority to US11/952,520 priority patent/US7829564B2/en
Priority to US13/238,923 priority patent/USRE43802E1/en

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    • 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
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals 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
    • 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
    • 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
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/11—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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    • C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
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    • 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
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/20—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 a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
    • C07C311/31—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 atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/32—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 atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • 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
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    • 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
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
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    • C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
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    • 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
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
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    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
PCT/US1993/007814 1992-08-25 1993-08-24 Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors WO1994004492A1 (en)

Priority Applications (31)

Application Number Priority Date Filing Date Title
EP93923714A EP0656887B1 (en) 1992-08-25 1993-08-24 Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
JP50653094A JP3657002B2 (ja) 1992-08-25 1993-08-24 レトロウイルスプロテアーゼ阻害剤として有用なα−およびβ−アミノ酸ヒドロキシエチルアミノスルホンアミド
KR1020007012894A KR100336699B1 (ko) 1992-08-25 1993-08-24 레트로바이러스 프로테아제 저해제로서 유용한히드록시에틸아미노 술폰아미드
CA002140929A CA2140929C (en) 1992-08-25 1993-08-24 Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
DK93923714T DK0656887T3 (da) 1992-08-25 1993-08-24 Hydroxyethylaminosulfonamider til anvendelse som inhibitorer af retrovirale proteaser
DE69321845T DE69321845T2 (de) 1992-08-25 1993-08-24 Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen
AU53474/94A AU680635C (en) 1992-08-25 1993-08-24 Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
KR1019950700563A KR100296463B1 (ko) 1992-08-25 1993-08-24 레트로바이러스프로테아제저해제로서유용한히드록시에틸아미노술폰아미드
US08/204,827 US6060476A (en) 1992-08-25 1994-03-02 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US08/586,866 US6046190A (en) 1992-08-25 1994-08-23 Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
US08/294,468 US5968942A (en) 1992-08-25 1994-08-23 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
NO950533A NO305478B1 (no) 1992-08-25 1995-02-13 Hydroksyetylaminosulfonamider som retrovirale proteasehemmere
FI950650A FI112471B (fi) 1992-08-25 1995-02-14 Menetelmä uusien terapeuttisesti käyttökelpoisten hydroksietyyliaminosulfoniamidien valmistamiseksi
US08/451,090 US6455581B1 (en) 1992-08-25 1995-05-25 α-and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
NO983099A NO307047B1 (no) 1992-08-25 1998-07-03 Nye hydroksyetylaminosulfonamider som er nyttige som retrovirale proteasehemmere, farmasøytisk preparat inneholdende slike, og anvendelse derav
US09/288,080 US6248775B1 (en) 1992-08-25 1999-04-08 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US09/525,161 US6500832B1 (en) 1992-08-25 2000-03-14 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US09/798,255 US6417387B1 (en) 1992-08-25 2001-03-05 α-and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
FI20012317A FI119427B (fi) 1992-08-25 2001-11-27 Menetelmä retrovirusproteaasi-inhibiittoreina käyttökelpoisten hydroksietyyliaminosulfoniamidien valmistamiseksi
US10/157,019 US6646010B2 (en) 1992-08-25 2002-05-30 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US10/199,481 US6846954B2 (en) 1992-08-25 2002-07-22 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US10/633,376 US6924286B1 (en) 1992-08-25 2003-08-04 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US10/812,343 US7115618B2 (en) 1992-08-25 2004-03-30 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US11/110,943 US7141609B2 (en) 1992-08-25 2005-04-21 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US11/433,797 US7531538B2 (en) 1992-08-25 2006-05-15 α- and β-Amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US11/526,101 US7320983B2 (en) 1992-08-25 2006-09-25 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US11/788,947 USRE42889E1 (en) 1992-08-25 2007-04-23 α- and β- amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US11/788,948 USRE43596E1 (en) 1992-08-25 2007-04-23 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
NL300283C NL300283I1 (nl) 1992-08-25 2007-06-13 Alfa- en bèta-aminozuur-hydroxyethylamino-sulfonamiden die toepasbaar zijn als retrovirale-prothease-remmers.
US11/952,520 US7829564B2 (en) 1992-08-25 2007-12-07 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US13/238,923 USRE43802E1 (en) 1992-08-25 2011-09-21 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US93498492A 1992-08-25 1992-08-25
US07/934,984 1992-08-25

Related Parent Applications (3)

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US93498492A Continuation-In-Part 1992-08-25 1992-08-25
US10091193A Continuation-In-Part 1993-07-30 1993-07-30
US08/110,911 Continuation-In-Part US5843946A (en) 1992-08-25 1993-08-24 α-and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors

Related Child Applications (3)

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US20482792A Continuation-In-Part 1992-08-25 1992-12-19
US20487294A Continuation-In-Part 1993-03-09 1994-03-02
US08/204,827 Continuation-In-Part US6060476A (en) 1992-08-25 1994-03-02 α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors

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EP (2) EP0656887B1 (US06534493-20030318-C00291.png)
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NO (2) NO305478B1 (US06534493-20030318-C00291.png)
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WO1995006030A1 (en) * 1993-08-24 1995-03-02 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
WO1995032185A1 (en) * 1994-05-23 1995-11-30 Agouron Pharmaceuticals, Inc. N-(3-amino-2-hydroxybutyl)sulphonamide derivatives as hiv protease inhibitors
US5484926A (en) * 1993-10-07 1996-01-16 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
WO1996022275A1 (en) 1995-01-20 1996-07-25 G.D. Searle & Co. Method of preparing retroviral protease inhibitor intermediates
WO1996028464A1 (en) * 1995-03-10 1996-09-19 G.D. Searle & Co. Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
WO1996028463A1 (en) * 1995-03-10 1996-09-19 G.D. Searle & Co. Amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
WO1996028465A1 (en) * 1995-03-10 1996-09-19 G.D. Searle & Co. Heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US5585397A (en) * 1992-09-08 1996-12-17 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
US5691372A (en) * 1995-04-19 1997-11-25 Vertex Pharmaceuticals Incorporated Oxygenated-Heterocycle containing sulfonamide inhibitors of aspartyl protease
US5705647A (en) * 1996-09-05 1998-01-06 Agouron Pharmaceuticals, Inc. Intermediates for making HIV-protease inhibitors
US5723490A (en) * 1992-09-08 1998-03-03 Vertex Pharmaceuticals Incorporated THF-containing sulfonamide inhibitors of aspartyl protease
US5776971A (en) * 1995-03-10 1998-07-07 G.D. Searle & Co. Heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US5783701A (en) * 1992-09-08 1998-07-21 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
US5846993A (en) * 1992-12-22 1998-12-08 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
US5847201A (en) * 1995-11-16 1998-12-08 G.D. Searle & Co. N-protected/N-substituted-beta-amino hydroxy sulfonates
US5962725A (en) * 1996-09-05 1999-10-05 Agouron Pharmaceuticals, Inc. Intermediate compounds useful for making HIV protease inhibitors such as nelfinavir
US5968942A (en) * 1992-08-25 1999-10-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US6001851A (en) * 1997-03-13 1999-12-14 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
US6004957A (en) * 1995-06-07 1999-12-21 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
US6046190A (en) * 1992-08-25 2000-04-04 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
US6084107A (en) * 1997-09-05 2000-07-04 Agouron Pharmaceuticals, Inc. Intermediates for making HIV-protease inhibitors
WO2000042060A1 (en) * 1999-01-13 2000-07-20 Dupont Pharmaceuticals Company Bis-amino acid sulfonamides containing n-terminally a substituted benzyl group as hiv protease inhibitors
WO2000047551A2 (en) * 1999-02-12 2000-08-17 Vertex Pharmaceuticals Incorporated Inhibitors of aspartyl protease
US6117999A (en) * 1996-09-05 2000-09-12 Agouron Phramaceuticals, Inc. Methods of making HIV-protease inhibitors and intermediates for making HIV-protease inhibitors
US6127372A (en) * 1994-03-07 2000-10-03 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
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