IP Library › Granted Patent US 6,894,165
Granted Patent B2
US 6,894,165 · App. 10/824,232 · Granted May 17, 2005

Imidazonaphthyridines

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Quick Facts
Patent No.
US 6,894,165
App. No.
10/824,232
Granted
May 17, 2005
Kind
B2
Abstract

Imidazonaphthyridine and tetrahydroimidazonaphthyridine compounds induce the biosynthesis of cytokines such as interferon and tumor necrosis factor. The compounds exhibit antiviral and antitumor properties. Methods of preparing the compounds and intermediates useful in the preparation of the compounds are also disclosed.

Claims (135)

1. A compound of formula

wherein

R 1 is selected from the group consisting of:

hydrogen;

C 1-20 alkyl or C 2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:

aryl;

heteroaryl;

heterocyclyl;

O—C 1-20 alkyl,

O—(C 1-20 alkyl) 0-1 -aryl;

O—(C 1-20 alkyl) 0-1 -heteroaryl;

O—(C 1-20 alkyl) 0-1 -heterocyclyl;

C 1-20 alkoxycarbonyl;

S(O) 0-2 —C 1-20 alkyl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -aryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heteroaryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heterocyclyl;

N(R 3 ) 2 ;

N 3 ;

oxo;

halogen;

NO 2 ;

OH; and

SH; and

C 1-20 alkyl-NR 3 -Q-X—R 4 or —C 2-20 alkenyl-NR 3 -Q-X—R 4 wherein Q is —CO— or —SO 2 —; X is a bond, —O— or —NR 3 — and R 4 is aryl; heteroaryl; heterocyclyl; or —C 1-20 alkyl or C 2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:

aryl;

heteroaryl;

heterocyclyl;

O—C 1-20 alkyl, —O—(C 1-20 alkyl) 0-1 -aryl;

O—(C 1-20 alkyl) 0-1 -heteroaryl;

O—(C 1-20 alkyl) 0-1 -heterocyclyl;

C 1-20 alkoxycarbonyl;

S(O) 0-2 —C 1-20 alkyl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -aryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heteroaryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heterocyclyl;

N(R 3 ) 2 ;

NR 3 —CO—O—C 1-20 alkyl;

N 3 ;

oxo;

halogen;

NO 2 ;

OH; and

SH; or R 4 is

wherein Y is —N— or —CR—;

R 2 is selected from the group consisting of:

hydrogen;

C 1-10 alkyl;

C 2-10 alkenyl;

aryl;

C 1-10 alkyl-O—C 1-10 -alkyl;

C 1-10 alkyl-O—C 2-10 alkenyl; and

C 1-10 alkyl or C 2-10 alkenyl substituted by one or more substituents selected from the group consisting of:

OH;

halogen;

N(R 3 ) 2 ;

CO—N(R 3 ) 2 ;

CO—C 1-10 alkyl;

N 3 ;

aryl;

heteroaryl;

heterocyclyl;

CO-aryl; and

CO-heteroaryl;

each R 3 is independently selected from the group consisting of hydrogen and C 1-10 alkyl; and

each R is independently selected from the group consisting of hydrogen, C 1-10 alkyl C 1-10 alkoxy, halogen and trifluoromethyl,

or a pharmaceutically acceptable salt thereof.

2. A compound of formula

wherein

R 1 is selected from the group consisting of:

hydrogen;

C 1-20 alkyl or C 2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:

aryl;

heteroaryl;

heterocyclyl;

O—C 1-20 alkyl,

O—(C 1-20 alkyl) 0-1 -aryl;

O—(C 1-20 alkyl) 0-1 -heteroaryl;

O—(C 1-20 alkyl) 0-1 -heterocyclyl;

C 1-20 alkoxycarbonyl;

S(O) 0-2 —C 1-20 alkyl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -aryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heteroaryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heterocyclyl;

N(R 3 ) 2 ;

N 3 ;

oxo;

halogen;

NO 2 ;

OH; and

SH; and

C 1-20 alkyl-NR 3 -Q-X—R 4 or —C 2-20 alkenyl-NR 3 -Q-X—R 4 wherein Q is —CO— or —SO 2 —; X is a bond, —O— or —NR 3 — and R 4 is aryl; heteroaryl; heterocyclyl; or —C 1-20 alkyl or C 2-20 alkenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of:

aryl;

heteroaryl;

heterocyclyl;

O—C 1-20 alkyl,

O—(C 1-20 alkyl) 0-1 -aryl;

O—(C 1-20 alkyl) 0-1 -heteroaryl;

O—(C 1-20 alkyl) 0-1 -heterocyclyl;

C 1-20 alkoxycarbonyl;

S(O) 0-2 —C 1-20 alkyl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -aryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heteroaryl;

S(O) 0-2 —(C 1-20 alkyl) 0-1 -heterocyclyl;

N(R 3 ) 2 ;

NR 3 —CO—O—C 1-20 alkyl;

N 3 ;

oxo;

halogen;

NO 2 ;

OH; and

SH; or R 4 is

wherein Y is —N— or —CR—;

R 2 is selected from the group consisting of:

hydrogen;

C 1-10 alkyl;

C 2-10 alkenyl;

aryl;

C 1-10 alkyl-O—C 1-10 -alkyl;

C 1-10 alkyl-O—C 2-10 alkenyl; and

C 1-10 alkyl or C 2-10 alkenyl substituted by one or more substituents selected from the group consisting of:

OH;

halogen;

N(R 3 ) 2 ;

CO—N(R 3 ) 2 ;

CO—C 1-10 alkyl;

N 3 ;

aryl;

heteroaryl;

heterocyclyl;

CO-aryl; and

CO-heteroaryl;

each R 3 is independently selected from the group consisting of hydrogen and C 1-10 alkyl; and

each R is independently selected from the group consisting of hydrogen, C 1-10 alkyl, C 1-10 alkoxy, halogen and trifluoromethyl,

or a pharmaceutically acceptable salt thereof.

Assignments (2)
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 →
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 →