US 2007/0185139 A1Published application

Thiazolopyrimidine kinase inhibitors

AssigneeJanssen Pharmaceutica NV

InventorsEva Binnun, Peter Connolly, Sigmond Johnson, Ronghui Lin, Steven Middleton, Sandra Moreno-Mazza, Niranjan Pandey, Steven Wetter

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Abstract

The present invention is directed to novel thiazolopyrimidine compounds of Formula (I) or a form or composition thereof and the thereof as inhibitors of ATP-protein kinase interactions.

Claims31

Dependent claims

A compound of a formula:

and a form thereof, wherein
p is 0, 1, 2 or 3;
L is selected from the group consisting of O, S, N(R5) and a bond;
R5 is selected from the group consisting of hydrogen, C1-8alkyl and C1-8alkyl(C1-8alkoxy);
Ar1 is selected from the group consisting of aryl, heteroaryl and heterocyclyl;
R1 and R2 is each independently selected from the group consisting of
(1) hydrogen,
(2) C1-8alkyl,
(3) C2-8alkenyl,
(4) C2-8alkynyl,
(5) C1-8alkoxy,
wherein (2), (3), (4) and (5) is each optionally substituted with one, two or three substituents independently selected from the group consisting of
(i) C3-8cycloalkyl,
(ii) aryl,
(iii) heteroaryl,
(iv) heterocyclyl,
wherein (i), (ii), (iii) and (iv) are optionally substituted with one, two or three substituents independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkoxy,
(c) C1-8alkyl(C1-8alkoxy),
(d) C1-8alkyl(halogen)1-3,
(e) C1-8alkyl(hydroxy)1-3,
(f) CO2(C1-8alkyl),
(g) amino optionally mono or disubstituted with C1-8alkyl,
(h) cyano,
(i) halogen,
(j) hydroxy,
(k) C1-8alkyl(amino) optionally mono or disubstituted on amino with C1-8alkyl,
(l) C3-8cycloalkyl, and
(m) aryl optionally substituted with C1-8alkyl, halogen, hydroxy, and
(v) amino optionally mono or disubstituted with a substituent independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkyl(C1-8alkoxy),
(c) C1-8alkyl(hydroxy)1-3,
(d) C3-8cycloalkyl,
(e) heterocyclyl optionally substituted with one or two C1-8alkyl substituents, and
(f) C1-8alkyl(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents,
(6) amino optionally mono or disubstituted with a substituent independently selected from the group consisting of
(i) C1-8alkyl,
(ii) heterocyclyl optionally substituted with one or two C1-8alkyl substituents, and
(iii) C1-8alkyl(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents,
(7) cyano,
(8) halogen,
(9) hydroxy,
(10) C3-8cycloalkyl,
(11) aryl,
(12) heteroaryl,
(13) heterocyclyl,
(14) SO2(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents,
(15) C(O) substituted with a substituent selected from the group consisting of
(i) hydroxy,
(ii) C1-8alkyl,
(iii) C1-8alkoxy, and
(iv) amino optionally mono or disubstituted with a substituent independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkyl(C1-8alkoxy),
(c) C1-8alkyl(amino) optionally mono or disubstituted on amino with C1-8alkyl, and
(d) C1-8alkyl(hydroxy)1-3, and
(16) SO2(amino) optionally mono or disubstituted on amino with a substituent independently selected from the group consisting of
(i) C1-8alkyl,
(ii) C1-8alkyl(C1-8alkoxy),
(iii) C1-8alkyl(amino) optionally mono or disubstituted on amino with C1-8alkyl,
(iv) C1-8alkyl(hydroxy)1-3, and
(v) C1-8alkyl(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents;
Ar2 is selected from the group consisting of aryl and heteroaryl;
and
R3 and R4 is each independently selected from the group consisting of
(1) hydrogen,
(2) C1-8alkyl,
(3) C2-8alkenyl,
(4) C2-8alkynyl,
(5) C1-8alkoxy,
wherein (2), (3), (4) and (5) is each optionally substituted with one, two or three substituents independently selected from the group consisting of
(i) halogen,
(ii) hydroxy,
(iii) C3-8cycloalkyl, and
(iv) aryl,
wherein (iii) and (iv) are optionally substituted with one, two or three substituents independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkoxy,
(c) halogen, and
(d) hydroxy,
(6) amino optionally mono or disubstituted with C1-8alkyl,
(7) oxy substituted with a substituent selected from the group consisting of
(i) C3-8cycloalkyl,
(ii) aryl, and
(iii) heteroaryl,
(8) cyano,
(9) halogen,
(10) hydroxy,
(11) nitro, and
(12) heterocyclyl.

89 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/498,221Filed 2 Aug 2006
Priority: 8 Aug 2005
Published: 9 Aug 2007
Term ends: Not estimatedThe source records don’t support an estimate.

Classification35 codes

C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/18
Drugs for disorders of the alimentary tract or the digestive system: for pancreatic disorders, e.g. pancreatic enzymes
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics

Family

Application60/706,840Us provisional application · filed 8 Aug 2005
US 7,605,154 B2Related patent
US 2007/0185139 A1This patent

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

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Abstract

The present invention is directed to novel thiazolopyrimidine compounds of Formula (I) or a form or composition thereof and the thereof as inhibitors of ATP-protein kinase interactions.

A compound of a formula:

and a form thereof, wherein
p is 0, 1, 2 or 3;
L is selected from the group consisting of O, S, N(R5) and a bond;
R5 is selected from the group consisting of hydrogen, C1-8alkyl and C1-8alkyl(C1-8alkoxy);
Ar1 is selected from the group consisting of aryl, heteroaryl and heterocyclyl;
R1 and R2 is each independently selected from the group consisting of
(1) hydrogen,
(2) C1-8alkyl,
(3) C2-8alkenyl,
(4) C2-8alkynyl,
(5) C1-8alkoxy,
wherein (2), (3), (4) and (5) is each optionally substituted with one, two or three substituents independently selected from the group consisting of
(i) C3-8cycloalkyl,
(ii) aryl,
(iii) heteroaryl,
(iv) heterocyclyl,
wherein (i), (ii), (iii) and (iv) are optionally substituted with one, two or three substituents independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkoxy,
(c) C1-8alkyl(C1-8alkoxy),
(d) C1-8alkyl(halogen)1-3,
(e) C1-8alkyl(hydroxy)1-3,
(f) CO2(C1-8alkyl),
(g) amino optionally mono or disubstituted with C1-8alkyl,
(h) cyano,
(i) halogen,
(j) hydroxy,
(k) C1-8alkyl(amino) optionally mono or disubstituted on amino with C1-8alkyl,
(l) C3-8cycloalkyl, and
(m) aryl optionally substituted with C1-8alkyl, halogen, hydroxy, and
(v) amino optionally mono or disubstituted with a substituent independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkyl(C1-8alkoxy),
(c) C1-8alkyl(hydroxy)1-3,
(d) C3-8cycloalkyl,
(e) heterocyclyl optionally substituted with one or two C1-8alkyl substituents, and
(f) C1-8alkyl(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents,
(6) amino optionally mono or disubstituted with a substituent independently selected from the group consisting of
(i) C1-8alkyl,
(ii) heterocyclyl optionally substituted with one or two C1-8alkyl substituents, and
(iii) C1-8alkyl(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents,
(7) cyano,
(8) halogen,
(9) hydroxy,
(10) C3-8cycloalkyl,
(11) aryl,
(12) heteroaryl,
(13) heterocyclyl,
(14) SO2(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents,
(15) C(O) substituted with a substituent selected from the group consisting of
(i) hydroxy,
(ii) C1-8alkyl,
(iii) C1-8alkoxy, and
(iv) amino optionally mono or disubstituted with a substituent independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkyl(C1-8alkoxy),
(c) C1-8alkyl(amino) optionally mono or disubstituted on amino with C1-8alkyl, and
(d) C1-8alkyl(hydroxy)1-3, and
(16) SO2(amino) optionally mono or disubstituted on amino with a substituent independently selected from the group consisting of
(i) C1-8alkyl,
(ii) C1-8alkyl(C1-8alkoxy),
(iii) C1-8alkyl(amino) optionally mono or disubstituted on amino with C1-8alkyl,
(iv) C1-8alkyl(hydroxy)1-3, and
(v) C1-8alkyl(heterocyclyl) optionally substituted on heterocyclyl with one or two C1-8alkyl substituents;
Ar2 is selected from the group consisting of aryl and heteroaryl;
and
R3 and R4 is each independently selected from the group consisting of
(1) hydrogen,
(2) C1-8alkyl,
(3) C2-8alkenyl,
(4) C2-8alkynyl,
(5) C1-8alkoxy,
wherein (2), (3), (4) and (5) is each optionally substituted with one, two or three substituents independently selected from the group consisting of
(i) halogen,
(ii) hydroxy,
(iii) C3-8cycloalkyl, and
(iv) aryl,
wherein (iii) and (iv) are optionally substituted with one, two or three substituents independently selected from the group consisting of
(a) C1-8alkyl,
(b) C1-8alkoxy,
(c) halogen, and
(d) hydroxy,
(6) amino optionally mono or disubstituted with C1-8alkyl,
(7) oxy substituted with a substituent selected from the group consisting of
(i) C3-8cycloalkyl,
(ii) aryl, and
(iii) heteroaryl,
(8) cyano,
(9) halogen,
(10) hydroxy,
(11) nitro, and
(12) heterocyclyl.

89 more elements

Facts

Application

11/498,221Filed 2 Aug 2006

Priority

8 Aug 2005

Published

9 Aug 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification35 codes

C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/18
Drugs for disorders of the alimentary tract or the digestive system: for pancreatic disorders, e.g. pancreatic enzymes
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics