Claims
- 1. A compound of the formula ##STR5## or its pharmaceutically acceptable salt, wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, or chloro;
- R.sub.2 and R.sub.3 each are independently hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, allyloxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, hydroxy, halo, cyano, nitro, amino, mono- or di-(C.sub.1 -C.sub.4 alkyl)amino, trifluoromethyl, or Z-Q-substituted C.sub.1 -C.sub.4 alkoxy, wherein Q is oxygen, sulfur, sulfinyl, sulfonyl, or a bond, and Z is C.sub.1 -C.sub.4 alkyl, phenyl, or phenyl substituted with a group selected from halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, nitro, amino, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, or C.sub.1 -C.sub.4 alkylsulfonyl; and
- R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkoxy;
- with the provisions that:
- (a) if R.sub.1 and two of R.sub.2, R.sub.3, and R.sub.4 are all hydrogen, the other of R.sub.2, R.sub.3, and R.sub.4 is not hydrogen, halo, hydroxy, nitro, amino, di-(C.sub.1 -C.sub.2 alkyl)amino, or C.sub.1 -C.sub.2 alkoxy;
- (b) if R.sub.1 and one of R.sub.2, R.sub.3, and R.sub.4 are both hydrogen, and another of R.sub.2, R.sub.3, and R.sub.4 is C.sub.1 -C.sub.2 alkoxy, the other of R.sub.2, R.sub.3, and R.sub.4 is not hydroxy or C.sub.1 -C.sub.2 alkoxy;
- (c) if R.sub.1 is chloro and two of R.sub.2, R.sub.3, and R.sub.4 are both hydrogen, the other of R.sub.2, R.sub.3, and R.sub.4 is not hydrogen, halo, C.sub.1 -C.sub.2 alkyl, or nitro; and
- (d) if R.sub.1 is chloro and R.sub.4 is hydrogen, R.sub.2 and R.sub.3 may not both be nitro.
- 2. The compounds of claim 1 wherein R.sub.1 is hydrogen.
- 3. The compounds of claim 2 wherein R.sub.2 is C.sub.1 -C.sub.4 alkylsulfinyl.
- 4. The compounds of claim 3 wherein R.sub.2 is methylsulfinyl.
- 5. The compounds of claim 2 wherein R.sub.2 is C.sub.1 -C.sub.4 alkyl.
- 6. The compounds of claim 5 wherein R.sub.2 is methyl.
- 7. The compounds of claim 2 wherein R.sub.3 is C.sub.1 -C.sub.4 alkoxy.
- 8. The compounds of claim 7 wherein R.sub.3 is methoxy.
- 9. The compounds of claim 2 wherein R.sub.2 is C.sub.1 -C.sub.4 alkylsulfonyl.
- 10. The compounds of claim 9 wherein R.sub.2 is methylsulfonyl.
- 11. The compound of claim 4 which is 2-(2-methoxy-4-methylsulfinylphenyl)imidazo[4,5-c]pyridine or a pharmaceutically acceptable salt thereof.
- 12. The compound of claim 10 which is 2-(2-methoxy-4-methylsulfonylphenyl)imidazo[4,5-c]pyridine or a pharmaceutically acceptable salt thereof.
- 13. The compound of claim 8 which is 2-(2-methoxy-4-methylmercaptophenyl)imidazo[4,5-c]pyridine or a pharmaceutically acceptable salt thereof.
- 14. The compound of claim 8 which is 2-(2-methoxy-4-trifluoromethylphenyl)imidazo[4,5-c]pyridine or a pharmaceutically acceptable salt thereof.
- 15. The compound of claim 8 which is 2-(2-methoxy-4-nitrophenyl)imidazo[4,5-c]pyridine or a pharmaceutically acceptable salt thereof.
CROSS-REFERENCE
"This application is a division of copending application Ser. No. 06/878,718, filed June 26, 1986, now U.S. Pat. No. 4,758,574 which is a continuation of Ser. No. 569,364, filed January 9, 1984, now abandoned, which is a continuation-in-part of application Ser. No. 469,883, filed February 25, 1983, now abandoned, which is a continuation-in-part of application Ser. No. 373,932, filed May 3, 1982, now abandoned.
US Referenced Citations (6)
Foreign Referenced Citations (5)
Number |
Date |
Country |
820316 |
Aug 1969 |
CAX |
72926 |
Mar 1983 |
EPX |
79083 |
May 1983 |
EPX |
93593 |
Nov 1983 |
EPX |
2119377 |
Nov 1983 |
GBX |
Non-Patent Literature Citations (10)
Entry |
Ber., 71B, 2347, (1938, abstracted in CA 33:984(6). |
J. Het. Chem., 17, 1757, (1980). |
Mutation Research, 78, 323, (1980). |
Org. Prep. Proced. Int., 12, (3-4), 234, (1980). |
J. Med. Chem., 13 (4), 697, (1970). |
J. Het. Chem., 6 (5), 605, (1966). |
CA 96:68900f, (1982), reporting Deposited Doc., 1980, VINITI 5441-80. |
CA 63:5628F, (1965), reporting Indian J. Chem., 3 (3), 138, (1965). |
J. Org. Chem., 29, 2403, (1964). |
Chemical Abstracts CA 88:22904s, (1978) summarizes U.S.S.R. patent 566,842. |
Divisions (1)
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878718 |
Jun 1986 |
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Continuations (1)
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Date |
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569364 |
Jan 1984 |
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Continuation in Parts (2)
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Number |
Date |
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Parent |
469883 |
Feb 1983 |
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Parent |
373932 |
May 1982 |
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