IP Library Granted Patent US 7,553,975
Granted Patent B2
US 7,553,975 · App. 11/442,758 · Granted Jun 30, 2009

Farnesyl transferase inhibitors

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Quick Facts
Patent No.
US 7,553,975
App. No.
11/442,758
Granted
Jun 30, 2009
Kind
B2
Abstract

A family of compounds capable of inhibiting the activity of farnesyl transferase.

Claims (23)

1. A compound having the formula

wherein:

R 1 is H, lower alkyl, cycloalkylthio, or lower alkylthio;

each of R 2 and R 3 , independently, is H or lower alkyl;

R 4 is O;

R 5 is H, or substituted or unsubstituted lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, cycloalkyl lower alkyl, cycloalkenyl, cycloalkenyl lower alkyl, aryl, aryl lower alkyl, heterocyclyl, or heterocyclyl lower alkyl, wherein the substituent is lower alkyl, —O—R 10 , —S(O) m R 10 (where m is 0, 1, or 2), —N(R 10 )(R 11 ), —N—C(O)—R 10 , —NH—(SO 2 )—R 10 ; —CO 2 —R 10 , —C(O)—N(R 10 )(R 11 ), or —(SO 2 )—N(R 10 )(R 11 );

R 6 is —C(O)NHCHR 13 CO 2 R 14 ;

R 7 is substituted or unsubstituted aryl, wherein the substituent is OH, lower alkyl, lower alkoxy, aryloxy, aryl lower alkoxy, —N(R 10 )(R 11 ), —COOH, —C(O)—N(R 10 )(R 11 ), or halo;

R 8 is H, or substituted or unsubstituted lower alkyl, cycloalkyl, cycloalkyl lower alkyl, cycloalkenyl, cycloalkenyl lower alkyl, aryl, aryl lower alkyl, heterocyclyl, or heterocyclyl lower alkyl, wherein the substituent is OH, lower alkyl, lower alkoxy, —N(R 10 )(R 11 ), —COOH, —C(O)—N(R 10 )(R 11 ), or halo; or R 8 and R 9 , together, form aryl or heterocyclyl; and

each of R 10 and R 11 , independently, is H, lower alkyl, aryl, aryl lower alkyl, cycloalkyl, cycloalkyl lower alkyl, heterocyclyl, or heterocyclyl lower alkyl;

R 12 is S;

R 13 is substituted lower alkyl wherein the substituent is —S(O) m R 10 (wherein m is 0); and

R 14 is H;

or a pharmaceutically acceptable salt thereof.

2. A compound of claim 1 , wherein R 5 is substituted or unsubstituted lower alkyl, cycloalkyl, or cycloalkyl lower alkyl; or a pharmaceutically acceptable salt thereof.

3. A compound of claim 2 , wherein each of R 1 , R 2 , and R 3 , independently, is H; or a pharmaceutically acceptable salt thereof.

4. A compound of claim 3 , wherein R 7 is phenyl; or a pharmaceutically acceptable salt thereof.

5. A compound of claim 4 , wherein R 8 is H; or a pharmaceutically acceptable salt thereof.

6. A compound of claim 5 , wherein R 5 is H; or a pharmaceutically acceptable salt thereof.

7. A compound of claim 1 , wherein said compound is of the formula:

2-(((2-amino-1-oxo-3-mercapto-propyl)-amino)-methyl)-5-phenyl-thiazole-4-carbonyl-methionine;

or a pharmaceutically acceptable salt thereof.

8. A compound consisting of a first compound and a second compound of claim 1 , wherein said first and second compounds are identical, and wherein R 1 in said first compound and R 1 in said second compound, in combination, form a disulfide bond; or a pharmaceutically acceptable salt thereof.

Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR NAME PREVIOUSLY RECORDED ON REEL 296336 FRAME 0777. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jan 5, 2016
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES, S.A.S.
To: IPSEN PHARMA S.A.S.
Reel/Frame 037430/0194 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS PREVIOUSLY RECORDED ON REEL 023034 FRAME 0251. ASSIGNOR(S) HEREBY CONFIRMS THE ADDRESS SHOULD BE 65 QUAI GEORGES GORSE, 92100 BOULOGNE-BILLANCOURT, FRANCE. Recorded Jan 16, 2013
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATION SCIENTIFIQUES (S.C.R.A.S.)
To: IPSEN PHARMA S.A.S.
Reel/Frame 029636/0777 →
CHANGE OF NAME Recorded Jul 31, 2009
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATION SCIENTIFIQUES (S.C.R.A.S.)
To: IPSEN PHARMA S.A.S.
Reel/Frame 023034/0251 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2006
From: BIOMEASURE, INCORPORATED
To: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES, S.A.S.
Reel/Frame 018101/0150 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2006
From: MORGAN, BARRY A.; GORDON, THOMAS D.
To: BIOMEASURE, INCORPORATED
Reel/Frame 018089/0231 →