Claims
- 1. A compound of the formula ##STR22## in which Ph represents phenyl substituted by lower alkyl, halogen and/or by trifluoromethyl, alk represents lower alkylidene, R.sub.1 is hydrogen or lower alkyl, and R.sub.2 represents carbamoyl that is unsubstituted or is substituted by lower alkyl or by lower alkanoyl, with the proviso that, in a compound of the formula I in which R.sub.1 represents methyl, R.sub.2 represents N,N-diethylcarbamoyl and alk represents methylene, Ph is other than phenyl substituted in the p-position by chlorine, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt.
- 2. A compound of the formula I according to claim 1, in which Ph represents phenyl mono-, di- or tri-substituted by lower alkyl, halogen and/or by trifluoromethyl, alk represents lower alkylidene, R.sub.1 is hydrogen or lower alkyl, and R.sub.2 represents carbamoyl, N-lower alkylcarbamoyl, N,N-di-lower alkylcarbamoyl or N-lower alkanoylcarbamoyl, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt.
- 3. A compound of the formula I according to claim 1, in which Ph represents phenyl mono-substituted by C.sub.1 -C.sub.4 -alkyl, halogen or by trifluoromethyl or di-substituted by halogen, by halogen and C.sub.1 -C.sub.4 -alkyl, or by halogen and trifluoromethyl, wherein halogen in each case has an atomic number of up to and including 35, alk represents 1,1- or 2,2-C.sub.1 -C.sub.4 -alkylidene, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sub.2 represents carbamoyl, N-C.sub.1 -C.sub.4 -alkylcarbamoyl, N,N-di-C.sub.1 -C.sub.4 -alkylcarbamoyl or N-C.sub.2 -C.sub.7 -alkanoylcarbamoyl, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt.
- 4. A compound of the formula I according to claim 1, in which Ph carries at least one of the lower alkyl and/or halogen substituents in an o-position or a trifluoromethyl substituent in a m-position, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt.
- 5. A compound of the formula I according to claim 1, in which Ph represents o-C.sub.1 -C.sub.4 -alkylphenyl, m-tri-fluoromethylphenyl, o-halophenyl or 2,3-, 2,4-, 2,5- or 2,6-dihalophenyl, wherein halogen in each case has an atomic number of up to and including 35, alk represents 1,1-C.sub.1 -C.sub.4 -alkylidene, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sub.2 represents carbamoyl or N-C.sub.1 -C.sub.4 -alkylcarbamoyl, N,N-di-C.sub.1 -C.sub.4 -alkylcarbamoyl or N-C.sub.2 -C.sub.7 -alkanoylcarbamoyl, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt.
- 6. A compound of the formula I according to claim 1 with the further proviso that Ph is other than phenyl mono-substituted by halogen, especially by chlorine, when R.sub.2 represents N,N-di-C.sub.1 -C.sub.4 -alkylcarbamoyl in which the two N-alkyl groups are identical or different, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt.
- 7. A compound of the formula I according to claim 1, in which Ph represents m-tri-fluoromethylphenyl, o-fluorophenyl or 2,6-difluorophenyl, alk represents methylene, R.sub.1 is C.sub.1 -C.sub.4 -alkyl, and R.sub.2 represents carbamoyl, in each case in free form or in form of a pharmaceutically acceptable salt.
- 8. A compound of the formula I according to claim 1, in which Ph represents m-trifluoromethylphenyl or 2,6-difluorophenyl, alk represents methylene, R.sub.1 is C.sub.1 -C.sub.4 -alkyl, and R.sub.2 represents carbamoyl, in each case in free form or in form of a pharmaceutically acceptable salt.
- 9. A compound according to claim 1 being 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
- 10. A compound according to claim 1 being 5-(o-chlorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
- 11. A compound according to claim 1 being 5-(o-fluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
- 12. A compound according to claim 1 being 4-methyl-5-(m-trifluoromethylbenzyl)-4H-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
- 13. A compound according to claim 1 being 4-ethyl-5-(2,6-difluorobenzyl)-4H-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
- 14. A compound according to claim 1 being 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-(N-methyl)carboxamide or a pharmaceutically acceptable salt thereof.
- 15. A compound according to claim 1 being 5-[1-(2,6-difluorophenyl)ethyl]-4-methyl-4H-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
- 16. A compound according to claim 1 being 5-(2,6-difluorobenzyl)-4-methyl-4H-1,2,4-triazole-3-(N-acetyl)carboxamide or a pharmaceutically acceptable salt thereof.
- 17. A pharmaceutical preparation containing an anti-convulsively effective amount of a compound of the formula ##STR23## in which Ph represents phenyl substituted by lower alkyl, halogen and/or by trifluoromethyl, alk represents lower alkylidene, R.sub.1 is hydrogen or lower alkyl, and R.sub.2 represents carbamoyl that is unsubstituted or is substituted by lower alkyl or by lower alkanoyl, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt, optionally together with customary pharmaceutical adjuncts.
- 18. A pharmaceutical preparation containing an anti-convulsively effective amount of a compound according to claim 1, or, as the case may be, a tautomer thereof, in each case in free form or in form of a pharmaceutically acceptable salt, optionally together with customary pharmaceutical adjuncts.
- 19. A compound according to claim 1 being 5-(2,6-difluorobenzyl)-1,2,4-triazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
Priority Claims (1)
Number |
Date |
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4035/86 |
Oct 1986 |
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Parent Case Info
This is a divisional of Ser. No. 622,130 filed Dec. 3, 1990 now U.S. Pat. No. 5,045,556 which is a continuation of Ser. No. 333,378 filed Apr. 5, 1989 now abandoned which is a continuation-in-part of Ser. No. 290,817 filed Dec. 22, 1988 now abandoned which is a continuation of Ser. No. 103,147 filed Oct. 1, 1987 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4789680 |
Meier |
Dec 1988 |
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Foreign Referenced Citations (4)
Number |
Date |
Country |
0126326 |
Nov 1984 |
EPX |
0174562 |
Mar 1986 |
EPX |
0267147 |
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0206368 |
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JPX |
Non-Patent Literature Citations (4)
Entry |
Pesson, M. "1,2,4-Triazole-5-Carboxylic Amides" CA 70:87820j (1969). |
Pesson, M. et al., "1,2,4-Triazole V. N,N-Dialkylamides Derived From 1,2,4-Triazoles-Carboxylic Acids" CA 73:66517n (1970). |
Ikizler, A. "Preparation of Some 1,2,4-Trizole Derivatives" CA 99:105183; (1983). |
Legraverend, M. "Synthesis of S-Triazolo [4,3rd]-and-[1,5rd]-1,2,4-Triazines" CA 96:217801d (1982). |
Divisions (1)
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Parent |
622130 |
Dec 1990 |
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Continuations (2)
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333378 |
Apr 1989 |
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Parent |
103147 |
Oct 1987 |
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Continuation in Parts (1)
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290817 |
Dec 1988 |
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