US4064265A
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US
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Dithiocarbamic acid esters
Assignee: Novartis Corp
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Filing: 1976-06-23
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Granted: 1977-12-20
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Expires: 1996-06-23
Abstract
Abstract The present invention relates to new dithiocarbamic acid esters having the formula ##STR1## wherein R 1 represents a phenyloxyphenyl or phenylaminophenyl radical which is unsubstituted or substituted by lower alkyl, halogen, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents lower alkylidene or lower alkylene, and also to salts of compounds of the formula (I), wherein R 2 represents hydrogen, with pharmaceutically acceptable bases. These new compounds possess a strong anthelminthic activity and are useful for the treatment of warm-blooded animals infected with parasitic helminths. A specific embodiment is the N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester.
Inventors
- 👤 Denis V. Varsanyi
- 👤 Ernst Aufderhaar
- 👤 Ernst Schweizer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 10:39
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/21; A61K31/27; A61P; A61P33/00; A61P33/10; Y; Y02; Y02A; Y02A50/00; Y02A50/30
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
64 words
A dithiocarbamic acid ester of the formula ##STR4## wherein R 1 represents a phenyloxyphenyl or phenylaminophenyl radical which is unsubstituted or substituted by lower alkyl, halogen, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents lower alkylidene or lower alkylene, and the salts of a compound of the formula I, wherein R 2 represents hydrogen, with pharmaceutically acceptable bases.
Claim 2
Dependent Claim
64 words
A dithiocarbamic acid ester of the formula ##STR4## wherein R 1 represents a phenyloxyphenyl or phenylaminophenyl radical which is unsubstituted or substituted by lower alkyl, halogen, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents lower alkylidene or lower alkylene, and the salts of a compound of the formula I, wherein R 2 represents hydrogen, with pharmaceutically acceptable bases.
Claim 3
Dependent Claim
34 words
A compound according to claim 1 having the formula I, wherein R 1 and alk have the meanings given in claim 1 and R 2 represents hydrogen, and its salts with pharmaceutically acceptable bases.
Claim 4
Dependent Claim
28 words
A compound according to claim 1 having the formula I, wherein R 1 and alk have the meanings given in claim 1 and R 1 represents lower alkyl.
Claim 5
Dependent Claim
75 words
A compound according to claim 1 having the formula I, wherein R 1 represents 4-phenyloxyphenyl or 4-phenylaminophenyl which is unsubstituted or substituted by methyl, chlorine, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3, and the salts of a compound of the formula I, wherein R 2 represents hydrogen, with pharmaceutically acceptable bases.
Claim 6
Dependent Claim
60 words
A compound according to claim 1 having the formula I, wherein R 1 represents 4-phenyloxyphenyl or 4phenylaminophenyl which is unsubstituted or substituted by methyl, chlorine, trifluoromethyl, nitro or cyano, R 1 represents hydrogen and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3, and its salts with pharmaceutically acceptable bases.
Claim 7
Dependent Claim
54 words
A compound according to claim 1 having the formula I, wherein R 1 represents 4-phenyloxyphenyl or 4-phenylaminophenyl which is unsubstituted or substituted by methyl, chlorine, trifluoromethyl, nitro or cyano, R 1 represents lower alkyl, and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3.
Claim 8
Dependent Claim
59 words
A compound according to claim 1, wherein R 1 represents 4-(4-nitrophenyloxy)-phenyl or 4-(4-nitrophenylamino)-phenyl, R 2 represents hydrogen or lower alkyl, and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3, and the salts of a compound of the formula I, wherein R 2 represents hydrogen, with pharmaceutically acceptable bases.
Claim 9
Dependent Claim
48 words
A compound according to claim 1 having the formula I, wherein R 1 represents 4-(4-nitrophenyloxy)-phenyl or 4-(4-nitrophenylamino)-phenyl, R 1 represents hydrogen and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3, and its salts with pharmaceutically acceptable bases.
Claim 10
Dependent Claim
42 words
A compound according to claim 1 having the formula I wherein R 1 represents 4-(4-nitrophenyloxy)-phenyl or 4-(4-nitrophenylamino)-phenyl, R 1 represents lower alkyl and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3.
Claim 11
Dependent Claim
10 words
A compound according to claim 1 which is N-[-4-(4-nitrophenyloxy)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester.
Claim 12
Dependent Claim
19 words
A compound according to claim 1 which is a salt of the N-[-4-(4-nitrophenyloxy)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester with a pharmaceutically acceptable base.
Claim 13
Dependent Claim
10 words
A compound according to claim 1 which is N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester.
Claim 14
Dependent Claim
19 words
A compound according to claim 1 which is a salt of the N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester with a pharmaceutically acceptable base.
Claim 15
Dependent Claim
10 words
A compound according to claim 1 which is N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-[(ethoxycarbonyl)-methyl]-ester.
Claim 16
Dependent Claim
93 words
A method for the treatment of infections with parasitic helminths in a warm-blooded animal comprising administration to said animal of an antihelminthically effective amount of a compound according to claim 1 having the formula ##STR5## wherein R 1 represents a phenyloxyphenyl or phenylaminophenyl radical which is unsubstituted or substituted by lower alkyl, halogen, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents lower alkylidene or lower alkylene, or of a salt of a compound of the formula I, wherein R 2 represents hydrogen, with a pharmaceutically acceptable base.
Claim 17
Dependent Claim
16 words
A method according to claim 15 wherein an anthelminthically effective amount of N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester is administered.
Claim 18
Dependent Claim
25 words
A method according to claim 15 wherein an anthelminthically effective amount of a salt of the N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester with a pharmaceutically acceptable base is administered.
Claim 19
Dependent Claim
98 words
A pharmaceutical preparation for the treatment of warm-blooded animals infected with parasitic helminths comprising an anti-helminthically effective amount of a compound according to claim 1 having the formula ##STR6## wherein R 1 represents a phenyloxyphenyl or phenylaminophenyl radical which is unsubstituted or substituted by lower alkyl, halogen, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents lower alkylidene or lower alkylene, or of a salt of a compound of the formula I, wherein R 2 represents hydrogen, with a pharmaceutically acceptable base, in aqueous suspension or in admixture with a solid pharmaceutical carrier.
Claim 20
Dependent Claim
83 words
A pharmaceutical preparation according to claim 18, wherein the anthelminthically effective compound is such of formula I, wherein R 1 represents 4-phenyloxyphenyl or 4-phenylaminophenyl which is unsubstituted or substituted by methyl, chlorine, trifluoromethyl, nitro or cyano, R 2 represents hydrogen or lower alkyl, and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3, or a salt of said compound of the formula I, wherein R 2 represents hydrogen, with a pharmaceutically acceptable base.
Claim 21
Dependent Claim
71 words
A pharmaceutical preparation according to claim 18, wherein the antheminthically effective compound is such of formula I, wherein R 1 represents 4-(4-nitrophenyloxy)-phenyl or 4-(4-nitrophenylamino)-phenyl, R 2 represents hydrogen or lower alkyl, and alk represents the radical of the formula --(CH 2 ) n --, wherein n is 1, 2 or 3, or a salt of said compound of the formula I, wherein R 2 represents hydrogen, with a pharmaceutically acceptable base.
Claim 22
Dependent Claim
16 words
A pharmaceutical preparation according to claim 18, wherein the anthelminthically effective compound is the N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester.
Claim 23
Dependent Claim
24 words
A pharmaceutical preparation according to claim 18, wherein the anthelminthically effective compound is a salt of the N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester with a pharmaceutically acceptable base.
References Cited (Backward Citations)
US3923854A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-19 | 1981-06-20 | 1981-12-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-19 | 1985-06-20 | 1985-12-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-19 | 1989-06-20 | 1989-12-20 | $7700.00 | Window Closed / Lapsed |