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Claims for Patent: 6,812,238

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Claims for Patent: 6,812,238

Title: N-substituted carbamoyloxyalkyl-azolium derivatives
Abstract:N-substituted carbamoyloxyalkyl-azolium derivatives which have antifungal activity and are useful for the treatment of fungal diseases.
Inventor(s): Fukuda; Hiroshi (Tokyo, JP), Hayase; Tadakatsu (Chigasaki, JP), Mizuguchi; Eisaku (Kamakura, JP), Shimma; Nobuo (Chigasaki, JP), Ohwada; Jun (Kamakura, JP), Oikawa; Nobuhiro (Kawasaki, JP), Sakaitani; Masahiro (Chigasaki, JP), Tsukazaki; Masao (Fujisawa, JP), Umeda; Isao (Yokohama, JP)
Assignee: Basilea Pharmaceutica AG (Binningen, CH)
Application Number:09/702,944
Patent Claims: 1. A compound of the formula (I), ##STR37##

wherein Q is a 3-[4-(4-cyanophenyl)thiazol-2-yl)]-2-(2,5-difluorophenyl)-1-(1H-1,2,4-tria zol-1-yl)-butan-2-ol moiety which is linked to the remainder of the compound of formula (I) by a nitrogen in the triazole; R.sup.1 is hydrogen or alkyl; R.sup.2 is hydrogen, alkyl, alkylcarbonyloxyalkyl, alkoxycarbonyl, alkylcarbonyl, mono- or dialkylaminoalkylcarbonyloxyalkyl; R.sup.3 is pyridin-2-yl or substituted pyridin-2-yl; and X.sup.- is a pharmaceutically acceptable anion, wherein when R.sup.3 is substituted pyridin-2-yl, the substituent is selected from the group consisting of halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, carboxy, alkyloxycarbonyl, cyano, trifluoromethyl, trifluoromethoxy, nitro, aminosulfonyl, alkylaminocarboyloxyalkyl, sulfo, alkylcarbonyloxyalkyl and aminoalkylcarbonyloxyalkyl; or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein R.sup.3 is substituted pyridin-2-yl.

3. The Compound of claim 2 having formula (II), ##STR38##

wherein ##STR39##

is pyridin-2-yl; R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, carboxy, alkyloxycarbonyl, cyano, trifluoromethyl, trifluoromethoxy nitro, aminosulfonyl, alkylaminocarboyloxyalkyl, sulfo, alkylcarbonyloxyalkyl and aminoalkylcarbonyloxyalkyl; and R.sup.6 is hydroxy, alkoxycarbonylalkylamino, alkoxycarbonylamino, amino, alkylamino, alkylcarbonyloxy, alkoxycarbonylalkylaminoalkylcarbonyloxy, alkoxycarbonylamino-alkylcarbonyloxy, alkylaminoalkylcarbonyloxy, aminoalkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylalkylamino, acyloxy, acylamino, acylalkylamino wherein said acyl group is a hydrolizable radical.

4. Compounds of claim 3 having formula (III), ##STR40##

wherein R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, carboxy, alkyloxycarbonyl, cyano, trifluoromethyl, trifluoromethoxy, nitro, aminosulfonyl or sulfo; and R.sup.6 is hydroxy, alkoxycarbonylalkylamino, alkoxycarbonylamino, amino, alkylamino, alkylcarbonyloxy, alkoxycarbonylalkylaminoalkylcarbonyloxy, alkoxycarbonylamino-alkylcarbonyloxy, alkylaminoalkylcarbonyloxy, aminoalkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylalkylamino, acyloxy, acylamino, acylalkylamino wherein said acyl is a hydrolizable radical.

5. The compound of claim 4 wherein R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, halogen, alkoxy, cyano, trifluoromethyl, trifluoromethoxy and nitro.

6. The compound of claim 5 wherein R.sup.4 and R.sup.5 are independently selected from the group consisting of hydrogen, halogen and alkoxy.

7. The compound of claim 4 wherein R.sup.4 and R.sup.5 are hydrogen.

8. The compound of claim 4 wherein R.sup.6 is alkylamino, alkylcarbonyloxy, alkylaminoalkylcarbonyloxy or aminoalkylcarbonyloxy.

9. The compound of claim 8 wherein R.sup.6 is alkylaminoalkylcarbonyloxy.

10. The compound of claim 1 wherein R.sup.1 is hydrogen or alkyl.

11. The compound of claim 10 wherein R.sup.1 is methyl.

12. The compound of claim 1 wherein R.sup.2 is hydrogen or alkyl.

13. The compound of claim 12 wherein R.sup.2 is alkyl.

14. The compound of claim 1 wherein X is a halogen.

15. The compound of claim 14 wherein X is chloro.

16. A compound selected from the group consisting of 1-[[N-methyl-N-3-[(methylamino)acetoxyethyl]pyridin-2-yl]carbamoyloxy]ethyl -1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2- yl]butyl]-1H-[1,2,4]triazol-4-ium chloride dihydrochloride, 1-[[N-methyl-N-3-[(methylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethy l-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2 -yl]butyl]-1H-[1,2,4]triazol-4-ium chloride hydrochloride, or 1-[[N-methyl-N-3-(acetoxymethyl)pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)- 2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H -[1,2,4]triazol-4-ium chloride hydrochloride.

17. A compound which is 1-[[N-methyl-N-3-[(methylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]eth yl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol- 2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride hydrochloride.

18. An pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

19. A method of treating fungal infections comprising administering to the infected organism an effective amount of a compound of claim 1.
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