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Patent Application

App. No. 10/552,696

Sapphyrins and uses thereof

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Patent No.: US None
App. No.: 10/552,696

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Abstract

The present invention relates to compounds of Formula (I): their pharmaceutical composition and their utility in treating neoplasm.

Claims (157)

1 . A compound of Formula I

its pharmaceutically acceptable salts and prodrugs there of, wherein:

R 1 represents —(CH 2 ) 1-4 —O—C(═O)—NR 31 R 32 , —(CH 2 ) 1-4 —X—CH 2 —O—(CH 2 CH 2 O) 0-3 —CH 3 , —C 1-4 alkyl, —(CH 2 ) 1-4 —R 21 , H. —R 21 , or —(CH 2 ) 1-4 —OH;

R 2 represents H, —C 1-4 straight chain alkyl, or —C 3-6 branched alkyl;

R 3 represents H, —C 1-4 straight chain alkyl, —C 3-6 branched alkyl, halogen, —NO 2 , —CN, O-alkyl, —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , —(CH 2 ) 1-4 —OH, or —(CH 2 ) 1-4 —OCOCH 3 ;

R 4 represents H, —C 1-4 straight chain alkyl, —C 3-6 branched alkyl, halogen, —NO 2 , —CN, —O-alkyl, —(CH 2 ) 1-4 —OH, —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , or —(CH 2 ) 1-4 —OCOCH 3 ;

R 5 represents H, —C 1-4 straight chain alkyl, —C 3-6 branched alkyl, halogen, —NO 2 , —CN, —O-alkyl, —(CH 2 ) 1-4 —OH, —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , or —(CH 2 ) 1-4 —OCOCH 3 ;

R 6 represents H, C 1-4 straight chain ally, C 3-6 branched alkyl, halogen, NO 2 , —CN, O-alkyl, —(CH 2 ) 1-4 —OH, —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , or —(CH 2 ) 1-4 —OCOCH 3 ;

R 7 represents H, —C 1-4 straight chain alkyl, or —C 3-6 branched alkyl;

R 8 represents —(CH 2 ) 1-4 —X—CH 2 —O—(CH 2 CH 2 O) 0-3 —CH 3 , —C 1-4 alkyl, —(CH 2 ) 1-4 —R 21 , —R 21 , H, —(CH 2 ) 1-4 —O—C(═O)—NR 31 R 32 , or (CH 2 ) 1-4 —OH;

R 9 represents —C 1-4 straight chain alkyl, —C 3-6 branched alkyl, H, —O—C 1-4 -alkyl, —O—C 3-6 branched alkyl, or —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 ;

R 10 represents H, —C 1-4 straight chain alkyl, —C 3-6 branched alkyl; —O—C 1-4 -alkyl, or —O—C 3-6 branched alkyl; X represents —OCO 2 CH 2 —, —O 2 C—, —NHCO—, —OCONHCH 2 , —NHCO 2 CH 2 —, —NHCONHCH 2 —, or —NHCH 2 —;

R 21 , R 22 , R 23 , R 24 , and R 25 independently at each occurrence are selected from H, —CH 2 OH, —CH 2 NH 2 , —CH 2 N(C 2 H 4 OH) 2 , —COOH, —CON(C 2 H 4 OH) 2 , —OCON(C 2 H 4 OH) 2 , —NHCON(C 2 H 4 OH) 2 , and —O(CH 2 CH 2 O) 0-3 CH 3 ;

R 31 represents H, —(CH 2 ) 1-6 OH, C((CH 2 ) 1-4 OH) 3 , —C((CH 2 ) 1-4 O-alkyl) 3 , —(CH 2 ) 1-6 O-alkyl, or —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 ;

R 32 represents H, —(CH 2 ) 1-6 OH, —C((CH 2 ) 1-4 OH) 3 , —C((CH 2 ) 1-4 O-alkyl) 3 , —(CH 2 ) 1-6 O-alkyl, or —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 ;

R 33 represents H, —C 1-4 alkyl, —O—C 1-4 -alkyl, —O—C 3-6 branched alkyl, or

R 36 represents H or —C 1-4 alkyl;

R 37 represents H or —C 1-4 alkyl;

R 41 represents H or —C 1-4 alkyl; and

R 44 represents H, —C 1-4 alkyl, —O—C 1-4 alkyl, or

2 . A compound of claim 1 wherein:

R 1 represents —(CH 2 ) 3 —O—C(═O)—NR 31 R 32 ;

R 2 represents —C 1-4 straight chain alkyl, or —C 3-6 branched alkyl;

R 3 represents —C 1-4 straight chain alkyl, —C 3-6 branched alkyl, halogen, —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , —O-alkyl, (CH 2 ) 1-4 —OH, or —(CH 2 ) 1-4 —OCOCH 3 ;

R 4 represents —C 1-4 straight chain alkyl, —C 3-5 branched alkyl, halogen, —(CH 2 ) 1-4 —OH, or —(CH 2 ) 1-3 —OCOCH 3 ;

R 5 represents —C 1-3 straight chain alkyl, —C 3-5 branched alkyl, halogen, —O-alkyl, —(CH 2 ) 1-3 —OH, —(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , or —(CH 2 ) 1-3 —OCOCH 3 ;

R 6 represents —C 1-3 straight chain alkyl, —C 3-5 branched alkyl, halogen, —O-alkyl, —(CH 2 ) 1-3 —OH, —(CH 2 ) 1-3 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0.2 —CH 3 , or —(CH 2 ) 1-4 —OCOCH 3 ;

R 7 represents —C 1-3 straight chain alkyl, or —C 3-5 branched alkyl;

R 8 represents —(CH 2 ) 2-4 —O—C(═O)—NR 31 R 32 ;

R 9 represents —C 1-3 straight chain alkyl, —C 3-5 branched alkyl, —(CH 2 ) 2-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 , or —O-alkyl;

R 10 represents —C 1-4 straight chain alkyl, —C 3-6 branched alkyl, or —O-alkyl;

R 31 represents H, or —(CH 2 ) 2-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 —CH 3 ; and

R 32 represents H, or —(CH 2 ) 2-4 O—(CH 2 ) 1-4 O—(CH 2 ) 1-4 O—(CH 2 ) 0-2 -CH 3 .

3 . A compound of claim 1 wherein:

R 2 represents —CH 3 ;

R 3 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 4 represents —CH 3 , or —C 2 H 5 ;

R 5 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 6 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 7 represents —CH 3 ;

R 9 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 10 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 31 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ;

R 32 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

4 . A compound of claim 1 , wherein:

R 1 represents —(CH 2 ) 3 —O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —CH 3 , or —C 2 H 5 ;

R 4 represents —CH 3 , or —C 2 H 5 ;

R 5 represents —CH 3 , or —C 2 H 5 ;

R 6 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 7 represents —CH 3 ;

R 9 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 10 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 31 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ;

R 32 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

5 . A compound of claim 1 wherein:

R 1 represents —(CH 2 ) 1-3 —O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —C 2 H 5 ;

R 4 represents —CH 3 ;

R 5 represents —CH 3 ;

R 6 represents —C 2 H 5 ;

R 7 represents —CH 3 ;

R 8 represents —(CH 2 ) 1-3 —O—C(═O)—NR 31 R 32 ;

R 9 represents —C 2 H 5 ;

R 10 represents —C 2 H 5 ;

R 31 represents —(CH 2 —CH 2 O) 3 CH 3 ;

R 32 represents —(CH 2 —CH 2 O) 3 CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

6 . A compound of claim 1 , wherein:

R 1 represents —(CH 2 ) 1-3 —O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —C 2 H 5 ;

R 4 represents —C 2 H 5 ;

R 5 represents —C 2 H 5 ;

R 6 represents —C 2 H 5 ;

R 7 represents —CH 3 ;

R 8 represents —(CH 2 ) 1-3 —O—C(═O)—NR 31 R 32 ;

R 9 represents —C 2 H 5 ;

R 10 represents —C 2 H 5 ;

R 31 represents —(CH 2 —CH 2 O) 3 CH 3 ;

R 32 represents —(CH 2 —CH 2 O) 3 CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

7 . A compound of claim 1 , wherein:

R 1 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —C 2 H 5 ;

R 4 represents —C 2 H 5 ;

R 5 represents —C 2 H 5 ;

R 6 represents —C 2 H 5 ;

R 7 represents —CH 3 ;

R 8 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 9 represents —C 2 H 5 ;

R 10 represents —C 2 H 5 ;

R 31 represents —(CH 2 ) 2 OH;

R 32 represents —(CH 2 ) 2 OH; and

R 33 , R 36 , R 41 and R 44 represent H.

8 . A compound of Formula I:

wherein:

R 1 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 4 represents —CH 3 , or —C 2 H 5 ;

R 5 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 6 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 7 represents —CH 3 ;

R 8 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 9 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 10 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 31 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ;

R 32 represents —(CH 2 ) 2 —C—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

9 . A compound of Formula I:

wherein:

R 1 represents —(CH 2 ) 2 O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —C 2 H 5 , or —OCH 3 ;

R 4 represents —CH 3 ;

R 5 represents —CH 3 ;

R 6 represents —C 2 H 5 , or —OCH 3 ;

R 7 represents —CH 3 ;

R 8 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 9 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 10 represents —CH 3 , —C 2 H 5 , or —OCH 3 ;

R 31 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ;

R 32 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

10 . A compound of Formula I:

wherein:

R 1 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 2 represents —CH 3 ;

R 3 represents —C 2 H 5 ;

R 4 represents —CH 3 ;

R 5 represents —CH 3 ;

R 6 represents —C 2 H 5 ;

R 7 represents —CH 3 ;

R 8 represents —(CH 2 ) 2 —O—C(═O)—NR 31 R 32 ;

R 9 represents —C 2 H 5 ;

R 10 represents —C 2 H 5 ;

R 31 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ;

R 32 represents —(CH 2 ) 2 —O—(CH 2 ) 2 —O—(CH 2 ) 2 —O—CH 3 ; and

R 33 , R 36 , R 41 and R 44 represent H.

11 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt form thereof.

12 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 8 or a pharmaceutically acceptable salt form thereof.

13 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 9 or a pharmaceutically acceptable salt form thereof.

14 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 10 or a pharmaceutically acceptable salt form thereof.

15 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 5 or a pharmaceutically acceptable salt form thereof.

16 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 6 or a pharmaceutically acceptable salt form thereof.

17 . A method of treating a host harboring a neoplasm comprising administering to the host a Formula I compound of claim 1 .

18 . A method of treating a host harboring a neoplasm comprising administering to the host a Formula I compound of claim 5 .

19 . A method of treating a host harboring a neoplasm comprising administering to the host a Formula I compound of claim 6 .

20 . A method of treating a host harboring a neoplasm comprising administering to the host a Formula I compound of claim 8 .

21 . A method of treating a host harboring a neoplasm comprising administering to the host a Formula I compound of claim 9 .

22 . A method of treating a host harboring a neoplasm comprising administering to the host a Formula I compound of claim 10.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2006

From: SESSLER, JONATHAN

To: BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEMS

Reel/Frame 017268/0758 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2006

From: MAGDA, DARREN; WANG, ZHONG

To: PHARMACYCLICS, INC.

Reel/Frame 017268/0984 →