IP Library Granted Patent US 7,217,815
Granted Patent B2
US 7,217,815 · App. 10/530,627 · Granted May 15, 2007

2-beta -modified-6-substituted adenosine analogs and their use as antiviral agents

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Quick Facts
Patent No.
US 7,217,815
App. No.
10/530,627
Granted
May 15, 2007
Kind
B2
Abstract

Various 2′-beta-methyl-6-substituted adenosine analogs (including 2,6-disubstituted adenosine, 8-aza-6-substituted adenosine, and 2-aza-6-substituted adenosine) are prepared by conventional and combinatorial library approaches. Contemplated compounds are particularly useful as therapeutic agents, and especially as antiviral agents.

Claims (12)

1. A compound accordine to Formula 1

wherein Z is selected from the group consisting of alkyl, haloalkyl, hydroxyalkyl, O-alkyl, O-haloalkyl, O-hydroxyalkyl, alkenyl, haloalkenyl, hydroxyalkenyl, alkynyl, haloalkynyl, hydroxyalkynyl, and CN;

R 3 and R 4 are independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, alkoxy, alkaryl, aryl, heteroaryl, substituted aryl, acyl, substituted acyl, and alkylsulfonyl; and

R is selected from the group consisting of H,

wherein BR 1 and B′R 2 are independently selected from the group consisting of OCH 2 CH 2 SC(═O)t-butyl, OCH 2 OC(═O)iPr, and NH-acyl, where acyl is an amino acid acyl group;

V, W, and W′ are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkaryl, and substituted alkaryl; and

B and B′ are independently O or NH; and

Z′ is hydrogen, CHWOH, CHWOCOW′, SW, or CH 2 aryl.

2. The compound of claim 1 wherein R 3 is H or CH 3 , and wherein R 4 is selected from the group consisting of H, CHO, C(O)CH 3 , C(O)OCH 3 , S(O) 2 CH 3 , and CH 3 .

3. The compound of claim 1 wherein V is m-chlorophenyl.

4. The compound of claim 2 wherein V is m-chlorophenyl.

5. The compound of claim 2 wherein R is H.

Assignments (10)
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMA POLAND SPOLKA Z ORGANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z.O.O.
Reel/Frame 073637/0222 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
Reel/Frame 073637/0126 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 3, 2019
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.À R.L.; VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z O. O.
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 049672/0652 →
SECURITY INTEREST Recorded Mar 11, 2019
From: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 048556/0758 →
SECURITY INTEREST Recorded Jul 19, 2017
From: VALEANT PHARMACEUTICALS INTERNATIONAL
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043045/0913 →
NOTICE OF SUCCESSION OF AGENCY Recorded Jan 9, 2015
From: GOLDMAN SACHS LENDING PARTNERS, LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 034749/0689 →
SECURITY AGREEMENT Recorded Jul 18, 2011
From: VALEANT PHARMACEUTICALS INTERNATIONAL, A DELAWARE CORPORATION; ATON PHARMA, INC., A DELAWARE CORPORATION; CORIA LABORATORIES, LTD., A DELAWARE CORPORATION; DOW PHARMACEUTICAL SCIENCES, INC., A DELAWARE CORPORATION; VALEANT PHARMACEUTICALS NORTH AMERICA LLC, A DELAWARE LLC; PRESTWICK PHARMACEUTICALS, INC., A DELAWARE CORPORATION; VALEANT BIOMEDICALS, INC., A DELAWARE CORPORATION
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 026606/0061 →
PATENT SECURITY RELEASE AGREEMENT Recorded Mar 14, 2011
From: GOLDMAN SACHS LENDING PARTNERS LLC
To: VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS NORTH AMERICA; CORIA LABORATORIES, LTD.; DOW PHARMACEUTICAL SCIENCES, INC.; ATON PHARMA, INC.
Reel/Frame 025950/0048 →
SECURITY AGREEMENT Recorded Oct 4, 2010
From: ATON PHARMA, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA; VALEANT PHARMACEUTICALS INTERNATIONAL; CORIA LABORATORIES, LTD.; DOW PHARMACEUTICAL SCIENCES, INC.
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 025084/0169 →