US 7,582,627 B2Granted

3-aminoquinazolin-2,4-dione antibacterial agents

AssigneeWarner-Lambert Company

InventorsPaul Bird, Edmund Lee Ellsworth, Dai Quoc Nguyen, Joseph Peter Sanchez, Howard Daniel Hollis Showalter, Rajeshwar Singh, Michael Andrew Stier, Tuan Phong Tran, Brian Morgan Watson, Judy Yip

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Abstract

Antibacterial 3-aminoquinazolin-2,4-diones have formula (I) wherein: R1 and R3 include alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, and heteroaryl; R5, R6, and R8 include H, alkyl, alkoxy, halo, NO2, CN, NH2, alkyl and dialkylamino; R7 includes hydrogen, alkyl, cycloalkyl, heterocyclic, fused heterocyclic, aryl and fused aryl; J and K are C or N; and pharmaceutically acceptable salts thereof.

Claims2

Dependent claims

A compound of Formula VII

or pharmaceutically acceptable salt thereof,
wherein:
R1 and R3 independently are H,
C1-C12 alkyl and substituted alkyl,
C2-C12 alkenyl and substituted alkenyl,
C2-C12 alkynyl and substituted alkynyl,
C3-C12 cycloalkyl and substituted cycloalkyl,
aryl and substituted aryl,
heterocyclic and substituted heterocyclic,
or heteroaryl and substituted heteroaryl;
R7 is hydrogen,
C1-C12 alkyl and substituted alkyl,
C2-C12 alkenyl and substituted alkenyl,
C2-C12 alkynyl and substituted alkynyl,
halo,
NO2,
CN,
NR′R″,
COOR′
aryl,
fused aryl,
heterocyclic,
fused heterocyclic,
bicyclic heterocyclic, or
spiro heterocyclic,
wherein all ring groups can be substituted;
and
R8 is H,
(O)nC1-C12 alkyl and substituted alkyl,
(O)nC2-C12 alkenyl and substituted alkenyl,
(O)nC2-C12 alkynyl and substituted alkynyl,
wherein n is 0 or 1,
halo,
NO2,
CN,
NR′R″;
wherein R′ and R″ independently are H,
C1-C12 alkyl and substituted alkyl,
C2-C12 alkenyl and substituted alkenyl,
C2-C12 alkynyl and substituted alkynyl,
CO—C1-C12 alkyl and substituted alkyl,
or R′ and R″ taken together with the nitrogen to which they are attached form a 3- to 7-membered ring containing from 1 to 3 heteroatoms selected from N, O, and S, said ring being unsubstituted or substituted with up to 4 substituent groups,
R7 is hydrogen,
C1-C12 alkyl and substituted alkyl,
C2-C12 alkenyl and substituted alkenyl,
C2-C12 alkynyl and substituted alkynyl,
halo,
NO2,
CN,
NR′R″,
COOR′
aryl,
fused aryl,
heterocyclic,
fused heterocyclic,
bicyclic heterocyclic, or
spiro heterocyclic,
wherein all ring groups can be substituted.

55 more elements

A compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:

3-Amino-7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-1-methylethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-phenoxyethyl)-pyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-phenoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-phenoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-phenoxyethyl)-4,4-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-methoxypropyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
3-Amino-7-[3-(1-amino-2-methoxypropyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methyl-1H-pyrido[4,3-d]pyrimidine-2,4-dione;
{2-Amino-2-[1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[4,3-d]pyrimidin-7-yl)pyrrolidin-3-yl]ethylurea;
{2-Amino-2-[1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[4,3-d]pyrimidin-7-yl)pyrrolidin-3-yl]ethylurea;
{2-Amino-2-[1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[4,3-d]pyrimidin-7-yl)-4-methylpyrrolidin-3-yl]ethylurea;
{2-Amino-2-[1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[4,3-d]pyrimidin-7-yl)-4-fluoropyrrolidin-3-yl]ethylurea;
and
{2-Amino-2-[1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[4,3-d]pyrimidin-7-yl)-4,4-dimethylpyrrolidin-3-yl]ethylurea.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/452,121Filed 13 Jun 2006 · division
Priority: 24 Jan 2000
Published: US 2006/0183762 A121 Dec 2006
Granted: 1 Sep 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 401/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
A61P 31/14
Antivirals: for RNA viruses
C07D 239/96
With hetero atoms directly attached in positions 2 and 4: two oxygen atoms

Family

Application60/178,252Us provisional application · filed 24 Jan 2000
Application60/241,267Us provisional application · filed 18 Oct 2000
PCT/US00/33656Parent of this division · filed 12 Dec 2000
US 2006/0287308 A1Pre-grant publication · published 21 Dec 2006
Application10/182,221Parent of this division
US 7,094,780 B1Parent of this division
US 2006/0183762 A1Published application
US 7,582,627 B2This patent

From the US filing history. Foreign family members aren’t listed.