US4038404A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,2,4-triazole antimycotic compositions and use thereof
Assignee: Bayer AG
•
Filing: 1976-01-02
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Granted: 1977-07-26
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Expires: 1996-01-02
Abstract
Abstract Antimycotic compositions are produced which comprise an antimycotically effective amount of a 1,2,4-triazole of the formula: ##STR1## or a pharmaceutically acceptable non-toxic salt thereof wherein X 1 is hydrogen or alkyl; X 2 is hydrogen or alkyl; R 1 is alkyl, unsubstituted or substituted aryl or unsubstituted or substituted aralkyl; R 2 is hydrogen, alkyl or unsubstituted or substituted aryl; R 3 is alkyl, cycloalkyl, unsubstituted or substituted aryl or unsubstituted or substituted aralkyl; and Y is a keto group or a functional derivative of a keto group, in combination with a pharmaceutically acceptable non-toxic, inert diluent or carrier.
Inventors
- 👤 Werner Meiser
- 👤 Wolfgang Kramer
- 👤 Karl Heinz Buchel
- 👤 Manfred Plempel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:47
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/63; C07C45/004; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07D; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
254 words
An antimycotic composition for treating mycotic infections in humans and animals which comprises an antimycotically effective amount of a 1,2,4-triazole of the formula ##STR72## wherein X 1 is hydrogen or alkyl of 1 to 3 carbon atoms; X 2 is hydrogen or alkyl of 1 to 3 carbon atoms; R 1 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 2 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 3 is alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 7 carbon atoms; and Y is CO; in combination with a pharmaceutically acceptable non-toxic, inert carrier.
Claim 2
Dependent Claim
254 words
An antimycotic composition for treating mycotic infections in humans and animals which comprises an antimycotically effective amount of a 1,2,4-triazole of the formula ##STR72## wherein X 1 is hydrogen or alkyl of 1 to 3 carbon atoms; X 2 is hydrogen or alkyl of 1 to 3 carbon atoms; R 1 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 2 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 3 is alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 7 carbon atoms; and Y is CO; in combination with a pharmaceutically acceptable non-toxic, inert carrier.
Claim 3
Dependent Claim
82 words
A composition according to claim 1 wherein X 1 and X 2 are each hydrogen; R 1 is phenyl unsubstituted or substituted by 1 to 5 halogeno moieties, by 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, fluorine, chlorine, bromine, iodine, trifluoromethyl, alkoxy of 1 or 2 carbon atoms, and nitro or by amino, phenyl, chlorophenyl or bromophenyl; R 2 is phenyl; and R 3 is alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
44 words
A composition according to claim 1 wherein R 1 is phenyl unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, t-butyl and trifluoromethyl, or by nitro or phenyl; and R 3 is methyl or t-butyl.
Claim 5
Dependent Claim
40 words
A composition according to claim 1 wherein R 1 is phenyl, chlorophenyl, dichlorophenyl, trichlorophenyl, tetrachlorophenyl, pentachlorophenyl, fluorophenyl, bromophenyl, chloromethylphenyl, chlorodimethylphenyl, chlorobromophenyl, chloronitrophenyl, trifluoromethylphenyl, dichlorotrifluoromethylphenyl, tolyl, dimethylphenyl, t-butylphenyl, methylnitrophenyl, methoxyphenyl, aminophenyl, diphenyl or phenylbromophenyl; and R 3 is methyl or t-butyl.
Claim 6
Dependent Claim
38 words
A composition according to claim 1 wherein the 1,2,4-triazole is in the form of a salt and said salt is selected from the group consisting of the hydrohalides, the phosphates, nitrates, monofunctional and difunctional carboxylates, hydroxycarboxylates and 1,5-naphthalenedisulphonate.
Claim 7
Dependent Claim
34 words
A composition according to claim 5 wherein the salt is selected from the group consisting of the hydrochloride, the hydrobromide, the phosphate, nitrate, acetate, maleate, succinate, fumarate, tartrate, citrate, salicylate, sorbate, lactate and 1,5-naphthalenedisulphonate.
Claim 8
Dependent Claim
17 words
A composition according to claim 1 wherein the 1,2,4-triazole is in the form of the hydrochloride salt.
Claim 9
Dependent Claim
16 words
The composition according to claim 1 wherein the 1,2,4-triazole is 1-[(4'-chlorophenoxy)]-1-[phenyl]-1-[1',2',4'-triazolyl-(1')]-3,3-dimethyl-butan-2-one or the hydrochloride salt thereof.
Claim 10
Dependent Claim
48 words
A composition according to claim 1 wherein the 1,2,4-triazole is of the formula: ##STR73## wherein X 1 is hydrogen; X 2 is hydrogen; R 1 is ##STR74## R 2 is ##STR75## R 3 is C(CH 3 ) 3 ; and Y is CO, or the hydrochloride salt thereof.
Claim 11
Dependent Claim
10 words
A composition according to claim 1 in oral administration form.
Claim 12
Dependent Claim
10 words
A composition according to claim 1 in topical application form.
Claim 13
Dependent Claim
12 words
A composition according to claim 1 in the form of a tablet.
Claim 14
Dependent Claim
15 words
A composition according to claim 12 wherein each tablet contains 200 ml of active agent.
Claim 15
Independent Claim
262 words
A method for treating mycotic infections in humans and animals which comprises administering to a human or animal in need thereof an antimycotically effective amount of a 1,2,4-triazole of the formula: ##STR76## wherein X 1 is hydrogen or alkyl of 1 to 3 carbon atoms; X 2 is hydrogen or alkyl of 1 to 3 carbon atoms; R 1 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 2 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 3 is alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 7 carbon atoms; and Y is CO; in combination with a pharmaceutically acceptable non-toxic, inert carrier.
Claim 16
Independent Claim
262 words
A method for treating mycotic infections in humans and animals which comprises administering to a human or animal in need thereof an antimycotically effective amount of a 1,2,4-triazole of the formula: ##STR76## wherein X 1 is hydrogen or alkyl of 1 to 3 carbon atoms; X 2 is hydrogen or alkyl of 1 to 3 carbon atoms; R 1 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 2 is phenyl unsubstituted or substituted by one to five substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, the same or different halogen, the same or different haloalkyl of 1 or 2 carbon atoms and 2 to 5 halogen atoms, alkoxy of 1 or 2 carbon atoms, the same or different haloalkoxy of 1 or 2 carbon atoms and 2 to 5 halogen atoms, and nitro, or by one substituent selected from the group consisting of phenyl, halophenyl or amino; R 3 is alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 7 carbon atoms; and Y is CO; in combination with a pharmaceutically acceptable non-toxic, inert carrier.
Claim 17
Dependent Claim
82 words
A method according to claim 14 wherein X 1 and X 2 are each hydrogen; R 1 is phenyl unsubstituted or substituted by 1 to 5 halogeno moieties, by 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, fluorine, chlorine, bromine, iodine, trifluoromethyl, alkoxy of 1 or 2 carbon atoms, and nitro or by amino, phenyl, chlorophenyl or bromophenyl; R 2 is phenyl; and R 3 is alkyl of 1 to 4 carbon atoms.
Claim 18
Dependent Claim
44 words
A method according to claim 14 wherein R 1 is phenyl unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, t-butyl and trifluoromethyl, or by nitro or phenyl; and R 3 is methyl or t-butyl.
Claim 19
Dependent Claim
40 words
A method according to claim 14 wherein R 1 is phenyl, chlorophenyl, dichlorophenyl, trichlorophenyl, tetrachlorophenyl, pentachlorophenyl, fluorophenyl, bromophenyl, chloromethylphenyl, chlorodimethylphenyl, chlorobromophenyl, chloronitrophenyl, trifluoromethylphenyl, dichlorotrifluoromethylphenyl, tolyl, dimethylphenyl, t-butylphenyl, methylnitrophenyl, methoxyphenyl, aminophenyl, diphenyl or phenylbromophenyl; and R 3 is methyl or t-butyl.
Claim 20
Dependent Claim
38 words
A method according to claim 14 wherein the 1,2,4-triazole is in the form of a salt and said salt is selected from the group consisting of the hydrohalides, the phosphates, nitrates, monofunctional and difunctional carboxylates, hydroxycarboxylates and 1,5-naphthalenedisulphonate.
Claim 21
Dependent Claim
34 words
A method according to claim 18 wherein the salt is selected from the group consisting of the hydrochloride, the hydrobromide, the phosphate, nitrate, acetate, maleate, succinate, fumarate, tartrate, citrate, salicylate, sorbate, lactate, and 1,5-naphthalenedisulphonate.
Claim 22
Dependent Claim
17 words
A method according to claim 14 wherein the 1,2,4-triazole is in the form of the hydrochloride salt.
Claim 23
Dependent Claim
17 words
The method according to claim 14 wherein the 1,2,4-triazole is 1-[(4'-chlorophenoxy)]-1-[phenyl]-1-[1' ,2',4'-triazolyl-(1')]-3,3-dimethyl-butan-2-one or the hydrochloride salt thereof.
Claim 24
Dependent Claim
48 words
The method according to claim 14 wherein the 1,2,4-triazole is of the formula: ##STR77## wherein X 1 is hydrogen; X 2 is hydrogen; R 1 is ##STR78## R 2 is ##STR79## R 3 is C(CH 3 ) 3 ; and Y is CO, or the hydrochloride salt thereof.
Claim 25
Dependent Claim
11 words
A method according to claim 14 wherein the administration is oral.
Claim 26
Dependent Claim
13 words
A method according to claim 14 wherein the administration is by topical application.
Claim 27
Dependent Claim
12 words
A method according to claim 14 wherein the administration is by tablet.
Claim 28
Dependent Claim
15 words
A method according to claim 25 wherein each tablet contains 200 ml of active agent.
Claim 29
Dependent Claim
19 words
A method according to claim 14 wherein the antimycotically effective amount is from 300 to 250 mg/kg per day.
Claim 30
Dependent Claim
19 words
A method according to claim 27 wherein the antimycotically effective amount is from 50 to 200 mg/kg. per day.
References Cited (Backward Citations)
US3755349A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |