Claims
- 1. Pyrimido�4,5-b!indoles of the formula (I)
- where R.sub.2-1 is
- (A) --H,
- (B) C.sub.1 -C.sub.8 alkyl optionally substituted with 1 thru 4
- (1) --OR.sub.2-10 where R.sub.2-10 is
- (a) --H,
- (b) C.sub.1-C.sub.4 alkyl,
- (c) --CO--R.sub.2-11 where R.sub.2-11 is C.sub.1 -C.sub.4 alkyl or C.sub.6 -C.sub.9 aralkyl,
- (d) --CO--NR.sub.2-12 R.sub.2-13 where R.sub.2-12 and R.sub.2-13 are the same or different and are --H or C.sub.1 -C.sub.2 alkyl,
- where R.sub.2-2 is
- (A) --H,
- (B) C.sub.1 -C.sub.8 alkyl optionally substituted with 1 thru 4
- (1) --OR.sub.2-10 where R.sub.2-10 is as defined above, or R.sub.2-1 and R.sub.2-2 are taken together with the attached nitrogen atom to form a heterocyclic ring selected from the group consisting of 1-pyrrolidinyl, 1-piperdinyl4-morpholinyl, 4-methylpiperazinyl, 4-thiomorpholinyl and 1-piperazinyl,
- where R.sub.4-1 is defined the same as R.sub.2-1, but may be the same or different than R.sub.2-1,
- where R.sub.4-2 is defined the same as R.sub.2-2 but may be the same or different than R.sub.2-2 ;
- where R.sub.7 is
- (A) C.sub.1 -C.sub.8 alkyl substituted with 1 thru 4 R.sub.7-1 where R.sub.7-1 is
- (1) --OR.sub.7-2 where R.sub.7-2 is
- (a) --H,
- (b) C.sub.1 -C.sub.4 alkyl,
- (c) --CO--R.sub.7-8 where R.sub.7-8 is C.sub.1 -C.sub.4 alkyl or C.sub.8 -C.sub.9 aralkyl,
- (d) --CO--NR.sub.7-10 R.sub.7-11 where R.sub.7-10 and R.sub.7-11 are the same or different and are --H or C.sub.1 -C.sub.3 alkyl,
- (2) --NR.sub.7-4 R.sub.7-5 where R.sub.7-4 and R.sub.7-6 are the same or different and are C.sub.1 -C.sub.4 alkyl or may taken together with the attached nitrogen atom to form the heterocyclic ring --N*--(CH.sub.2).sub.n1 --R.sub.5-6 --(CH.sub.2).sub.n2 * where the atoms marked with an asterisk (*) are bonded together resulting in the formation of a ring, where n.sub.1 is 1 thru 5, n.sub.2 is 0 thru 3 and R.sub.5-6 is
- (a) --C.sub.2 --,
- (b) --O--,
- (c) --S--,
- (3) --(CH.sub.2),.sub.n3 CO.sub.2 R.sub.7-2, where n.sub.3 is 0 thru 6 and R.sub.7-2 is as defined above,
- (4) --(CH.sub.2).sub.n3 CON(R.sub.7-3).sub.3 where n.sub.3 is as defined as above and where R.sub.7-3 may be the same or different and is --H or C.sub.1 -C.sub.3 alkyl,
- (5) --(CH.sub.2).sub.n3 CONR.sub.7-4 R.sub.7-5 where n.sub.3, R.sub.7-4, R.sub.7-5 are as defined above,
- (6) --(CH.sub.2).sub.n1 OR.sub.7-2 where R.sub.7-2 and n.sub.1 are as defined above,
- (7) --(CH.sub.2).sub.n2 OCOR.sub.7-3 where R.sub.7-3 and n.sub.1 are as defined above, and pharmaccutically acceptable salts thereof.
- 2. Pyrimido�4,5-b!indoles (I) according to claim 1 where R.sub.2-1 and R.sub.2-2 are taken together with the attached nitrogen atom to form 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-methylpiperazinyl, 4-thiomorpholinyl and 1-piperazinyl.
- 3. Pyrimido�4,5-b!indoles (I) according to claim 2 where R.sub.2-1 and R.sub.2-2 are 1-pyrrolidinyl and 1-piperazinyl.
- 4. Pyrimido�4,5-b!indoles (I) according to claim 2 where R.sub.4-1 and R.sub.4-2 are taken together with the attached nitrogen atom to form 1-pyrrolidinyl, 1-piperidinyl, 4-30 morpholinyl, 4-methylpiperazinyl, 4-thiomorpholinyl and 1-piperazinyl.
- 5. Pyrimido�4,5-b!indoles (I) according to claim 4 where R.sub.4-1 and R.sub.4-2 are 1-pyrrolidinyl and 1-piperazinyl.
- 6. Pyrimido�4,5-b!indoles (I) according to claim 2 where R.sub.7 is 2-(4-morpholinyl)ethyl, and 2-(1-piperidinyl)ethyl.
- 7. Pyrimido�4,5-b!indoles (I) according to claim 6 where R.sub.7 is 2-(4-morpholinyl)ethyl.
- 8. Pyrimido�4,5-b!indoles (I) according to claim 2 where the pharmaceutically acceptable salts are salts of the following acids hydrochloric, hydrobromic, methanesulfonic, sulfuric, phosphoric, nitric, benzoic, citric, tartaric, fumaric, maleic, CH.sub.3 --(CH.sub.2).sub.n --COOH where n is 0 thru 4, HOOC--(CH.sub.2)n--COOH where n is as defined above.
- 9. Pyrimido�4,5-b!indoles (I) according to claim 2 where the pyrimido�4,5-b!indole is selected from the group consisting of
- 9-(2-hydroxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole,
- 9-�2-(1-piperidinyl)ethyl!-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole,
- 9-�2-(4-morpholinyl)ethyl!-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole,
- 10. Pyrimido�4,5-b!indoles (I) according to claim 9 where the pyrimido�4,5-b!indole is 9-�2-(4-morpholinyl)ethyl!-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole.
- 11. Pyrimido�4,5-b!indoles (I) according to claim 10 where the pyrimido�4,5-b!indole is:
- 9-�2-(4-morpholinyl)ethyl!-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole monohydrochloride,
- 9-�2-(4-morpholinyl)ethyl!-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole sulfate.
- 12. Pyrimido�4,5-b!indoles (I) according to claim 11 where the pyrimido�4,5-b!indole is 9-�2-(4-morpholinyl)ethyl!-2,4-di-1-pyrrolidinyl-9H-pyrimido�4,5-b!indole monohydrochloride.
Parent Case Info
This application is a continuation (national phase) of International Application No. PCT/US96/02397, International Filing Date 1 Mar. 1996, which was a continuation-in-part of U.S. patent application Ser. No. 08/398,201 filed 2 Mar. 1995, now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US96/02397 |
3/1/1996 |
|
|
7/25/1997 |
7/25/1997 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO96/26941 |
9/6/1996 |
|
|
Non-Patent Literature Citations (1)
Entry |
WO93/20078 (Oct. 1993). |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
398201 |
Mar 1995 |
|