US 2003/0144293 A1Published application

N-alkyl-adamantyl triazinyl benzamide derivatives

AssigneePfizer Inc.

InventorAllen J. Duplantier

Life of this patent

Estimating the term…

Abstract

The present invention relates to novel to N-alkyl adamantyl triazinyl benzylamide derivatives of formmula I 1 and to processs for their preparation, intermediates useful in their preparation, pharmaceutical compositions containing them, and their use in therapy. The active compounds of the present invention are useful in the treatment of inflammation, osteoarthritis, rhematoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

Claims23

Dependent claims

A compound of the formula

32
wherein A is —(C═O)NH— or —NH(C═O)—;
X, Y and Z are ═(CR3)—, ═(CR4)—, and ═(CR5)—;
or ═N—, ═(CR4)—, and ═(CR5)—;
or ═(CR3)— ═N—, and ═(CR5)—;
or ═(CR3)—, ═(CR4)—, and ═N—;
or ═N—, ═(CR4)—, and ═N—;
or ═(CR3)—, ═N—, and ═N—;
or ═N—, ═N—, and CR5, respectively;
W is a bond, —O—, >(C═O), —(CH2)0—, —(CH═CH)—, —C═C—, —(CH2)oO—, —O(CH2)o—, —O(CH2)pO—, —O(CH2)qO(CH2)r—, —CR6(OH)—, —(CH2)rO(CH2)r—, —(CH2)rO(CH2)qO, >NR′, —(CH2)ONR7—, —NR7(CH2)o—, —(CH2)rNR7(CH2)r—, —O(CH2)pNR7—, —O(CH2)qNR7(CH2)r—, —(CH2)rNR7(CH2)qO—, —NR7(CH2)qO—, —NR7(CH2)qO(CH2)r—, —CONR7—, —NR7CO—, >S(O)n, —S(O)nCH2—, —CH2S(O)n—, —SO2NR7—, or —NR7SO2—;
m is an integer from 1 to 2;
n is an integer from 0 to 2;
o is an integer from 1 to 6;
p is an integer from 2 to 6;
q is an integer from 2 to 3;
r is an integer from 1 to 3;
R1 is a 5 to 10 membered saturated, unsaturated or partially unsaturated heterocyclic ring containing three to five nitrogen atoms and zero to three additional heteroatoms independently selected from the group consisting of —O— and —S(O)n—;
wherein any of said carbon atoms of said 5 to 10 membered saturated, unsaturated or partially unsaturated heterocyclic ring may optionally contain 1-3 oxo groups;
wherein one to three of said nitrogen atoms of said heterocycle able to support an additional substituent may also optionally be substituted by R8;
wherein any carbon atom of said heterocycle able to support an additional substituent may also optionally be substituted by one to four R9 substituents per ring;
R2 is selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) cyano, (iv) (C1-C4)alkyl optionally substituted by one to four chloro or fluoro, (v) (C2-C4)alkenyl;
(vi) (C2-C4)alkynyl and (vii) (C1-C4)alkyloxy optionally substituted by one to four chloro or fluoro;
R3, R4 and R5 are each independently selected from the group consisting of (i) hydrogen;
(ii) halogen, (iii) cyano, (iv) nitro, (v) amino, (vi) hydroxyl, (vii) (C1-C6)alkyl optionally substituted by one to four chloro or fluoro, (viii) (C3-C8)cycloalkyl optionally substituted by one to four chloro or fluoro, (ix) (C1-C6)alkyloxy optionally substituted by one to four chloro or fluoro, and (x) (C3-C8)cycloalkyloxy optionally substituted by one to four chloro or fluoro;
R6 is hydrogen or (C1-C6)alkyl;
R7 is hydrogen, (C1-C6)alkyl or (C3-C8)cycloalkyl;
R8 is absent or is selected from the group consisting of hydrogen, —CF3, (C1-C6)alkyl, HO—(C2-C6)alkyl and (C3-C8)cycloalkyl,
R9 is selected from the group suitable substituents such as hydrogen, halo, (C1-C6)alkyl optionally substituted with one to six fluoro, —CO2H, HO—(C2-C6)alkyl, (C1-C6)alkoxy optionally substituted with one to six fluoro, hydroxy, (C1-C10)heteroaryl and (C3-C8)cycloalkyl,
each R10 is independently selected from the group consisting of hydrogen or halo;
or a pharmaceutically acceptable salt or solvate thereof.

27 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/292,886Filed 12 Nov 2002
Priority: 12 Nov 2001
Published: 31 Jul 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification46 codes

C07D 253/075
With hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics

Family

Application60/336,892Us provisional application · filed 12 Nov 2001
US 6,927,219 B2Related patent
US 2003/0144293 A1This patent

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

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Abstract

A compound of the formula

32
wherein A is —(C═O)NH— or —NH(C═O)—;
X, Y and Z are ═(CR3)—, ═(CR4)—, and ═(CR5)—;
or ═N—, ═(CR4)—, and ═(CR5)—;
or ═(CR3)— ═N—, and ═(CR5)—;
or ═(CR3)—, ═(CR4)—, and ═N—;
or ═N—, ═(CR4)—, and ═N—;
or ═(CR3)—, ═N—, and ═N—;
or ═N—, ═N—, and CR5, respectively;
W is a bond, —O—, >(C═O), —(CH2)0—, —(CH═CH)—, —C═C—, —(CH2)oO—, —O(CH2)o—, —O(CH2)pO—, —O(CH2)qO(CH2)r—, —CR6(OH)—, —(CH2)rO(CH2)r—, —(CH2)rO(CH2)qO, >NR′, —(CH2)ONR7—, —NR7(CH2)o—, —(CH2)rNR7(CH2)r—, —O(CH2)pNR7—, —O(CH2)qNR7(CH2)r—, —(CH2)rNR7(CH2)qO—, —NR7(CH2)qO—, —NR7(CH2)qO(CH2)r—, —CONR7—, —NR7CO—, >S(O)n, —S(O)nCH2—, —CH2S(O)n—, —SO2NR7—, or —NR7SO2—;
m is an integer from 1 to 2;
n is an integer from 0 to 2;
o is an integer from 1 to 6;
p is an integer from 2 to 6;
q is an integer from 2 to 3;
r is an integer from 1 to 3;
R1 is a 5 to 10 membered saturated, unsaturated or partially unsaturated heterocyclic ring containing three to five nitrogen atoms and zero to three additional heteroatoms independently selected from the group consisting of —O— and —S(O)n—;
wherein any of said carbon atoms of said 5 to 10 membered saturated, unsaturated or partially unsaturated heterocyclic ring may optionally contain 1-3 oxo groups;
wherein one to three of said nitrogen atoms of said heterocycle able to support an additional substituent may also optionally be substituted by R8;
wherein any carbon atom of said heterocycle able to support an additional substituent may also optionally be substituted by one to four R9 substituents per ring;
R2 is selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) cyano, (iv) (C1-C4)alkyl optionally substituted by one to four chloro or fluoro, (v) (C2-C4)alkenyl;
(vi) (C2-C4)alkynyl and (vii) (C1-C4)alkyloxy optionally substituted by one to four chloro or fluoro;
R3, R4 and R5 are each independently selected from the group consisting of (i) hydrogen;
(ii) halogen, (iii) cyano, (iv) nitro, (v) amino, (vi) hydroxyl, (vii) (C1-C6)alkyl optionally substituted by one to four chloro or fluoro, (viii) (C3-C8)cycloalkyl optionally substituted by one to four chloro or fluoro, (ix) (C1-C6)alkyloxy optionally substituted by one to four chloro or fluoro, and (x) (C3-C8)cycloalkyloxy optionally substituted by one to four chloro or fluoro;
R6 is hydrogen or (C1-C6)alkyl;
R7 is hydrogen, (C1-C6)alkyl or (C3-C8)cycloalkyl;
R8 is absent or is selected from the group consisting of hydrogen, —CF3, (C1-C6)alkyl, HO—(C2-C6)alkyl and (C3-C8)cycloalkyl,
R9 is selected from the group suitable substituents such as hydrogen, halo, (C1-C6)alkyl optionally substituted with one to six fluoro, —CO2H, HO—(C2-C6)alkyl, (C1-C6)alkoxy optionally substituted with one to six fluoro, hydroxy, (C1-C10)heteroaryl and (C3-C8)cycloalkyl,
each R10 is independently selected from the group consisting of hydrogen or halo;
or a pharmaceutically acceptable salt or solvate thereof.

27 more elements

Facts

Application

10/292,886Filed 12 Nov 2002

Priority

12 Nov 2001

Published

31 Jul 2003

Term ends

Not estimatedThe source records don’t support an estimate.

Classification46 codes

C07D 253/075
With hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics