US4072696A
Expired / Lapsed
US
⏱️ 0.0 years remaining
5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
Assignee: Syntex USA LLC
•
Filing: 1974-01-18
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Granted: 1978-02-07
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Expires: 1994-01-18
Abstract
Abstract Carbalkoxythioureidobenzene derivatives represented by the following formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R 1 is --SR 2 , --SOR 2 , --SO 2 R 2 , --OR 2 , --SCN, --SC(O)NR 3 R 4 , or --M'(CH 2 ) n MR 7 where n is 1-4; R 2 is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, aralkyl or aryl, provided that when R 1 is --SO 2 R 2 , R 2 is not aralkyl or phenyl; R 3 and R 4 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; Y is amino, nitro, acylamino where the acyl portion has 1 to 6 carbon atoms, --NHC(O) (CH 2 ) m COOH where m is 1-6, or --NHC(S)NHCOOR; M and M' are independently O, S or ##STR2## and R 7 is lower alkyl having 1 to 4 carbon atoms or aryl. The R 1 substitution is either at the 4- or 5-position. The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
Inventors
- 👤 Colin C. Beard
- 👤 John A. Edwards
- 👤 John H. Fried
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 06:58
CPC Classifications
C; C07; C07C; C07C335/00; C07C335/04; C07C335/24; C07C335/28
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
185 words
A compound selected from the group of compounds represented by the formula: ##STR9## where R is a lower alkyl group having 1 to 4 carbon atoms; R 1 is --SR 2 , --SOR 2 , --OR 2 , --SCN, or --M'(CH 2 ) n MR 7 where n is 1-4; R 2 is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, benzyl or phenyl, provided that when R 1 is --SO 2 R 2 , R 2 is not benzyl or phenyl, provided further that when R 1 is either --SR 2 or --OR 2 , R 2 can not be either alkyl or cycloalkyl; Y is amino, nitro, alkanoylamino having 1 to 6 carbon atoms, --NHC(O) (CH 2 ) m COOH where m is 1-6, or --NHC(S)NHCOOR; M and M' are independently O, S or ##STR10## and R 7 is lower alkyl having 1 to 4 carbon atoms or phenyl; the R 1 -substitution being at the 4- or 5-position; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
185 words
A compound selected from the group of compounds represented by the formula: ##STR9## where R is a lower alkyl group having 1 to 4 carbon atoms; R 1 is --SR 2 , --SOR 2 , --OR 2 , --SCN, or --M'(CH 2 ) n MR 7 where n is 1-4; R 2 is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, benzyl or phenyl, provided that when R 1 is --SO 2 R 2 , R 2 is not benzyl or phenyl, provided further that when R 1 is either --SR 2 or --OR 2 , R 2 can not be either alkyl or cycloalkyl; Y is amino, nitro, alkanoylamino having 1 to 6 carbon atoms, --NHC(O) (CH 2 ) m COOH where m is 1-6, or --NHC(S)NHCOOR; M and M' are independently O, S or ##STR10## and R 7 is lower alkyl having 1 to 4 carbon atoms or phenyl; the R 1 -substitution being at the 4- or 5-position; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
14 words
The compound of claim 1 wherein the R 1 substituent is at the 4-position.
Claim 4
Dependent Claim
14 words
The compound of claim 1 wherein the R 1 substituent is at the 5-position.
Claim 5
Dependent Claim
12 words
The compound of claim 1 wherein R 1 is --SR 2 .
Claim 6
Dependent Claim
12 words
The compound of claim 1 wherein R 1 is --SOR 2 .
Claim 7
Dependent Claim
14 words
The compound of claim 1 wherein R 1 is --SO 2 R 2 .
Claim 8
Dependent Claim
12 words
The compound of claim 1 wherein R 1 is --OR 2 .
Claim 9
Dependent Claim
10 words
The compound of claim 1 wherein R 1 is --SCN.
Claim 10
Dependent Claim
16 words
The compound of claim 1 wherein R 1 is --O(CH 2 ) n OR 7 .
Claim 11
Dependent Claim
16 words
The compound of claim 1 wherein R 1 is --O(CH 2 ) n SR 7 .
Claim 12
Dependent Claim
16 words
The compound of claim 1 wherein R 1 is --S(CH 2 ) n OR 7 .
Claim 13
Dependent Claim
11 words
The compound of claim 1 wherein R 2 is lower alkyl.
Claim 14
Dependent Claim
11 words
The compound of claim 1 wherein R 2 is lower alkenyl.
Claim 15
Dependent Claim
11 words
The compound of claim 1 wherein R 2 is lower alkynyl.
Claim 16
Dependent Claim
16 words
The compound of claim 1 wherein R 1 is --S(CH 2 ) n SR 7 .
Claim 17
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is benzyl.
Claim 18
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is phenyl.
Claim 19
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-(2-phenoxyethoxy)benzene.
Claim 20
Dependent Claim
7 words
The compound of claim 1 wherein 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5-(2-phenoxyethoxy)benzene.
Claim 21
Dependent Claim
9 words
The compound of claim 1 wherein Y is amino.
Claim 22
Dependent Claim
9 words
The compound of claim 1 wherein Y is nitro.
Claim 23
Dependent Claim
9 words
The compound of claim 1 wherein Y is acetamido.
Claim 24
Dependent Claim
9 words
The compound of claim 1 wherein Y is --NHC(S)NHCOOR.
Claim 25
Dependent Claim
11 words
The compound of claim 1 wherein Y is --NHC(S)NHCOOCH 3 .
Claim 26
Dependent Claim
13 words
The compound of claim 1 wherein Y is --NHC(O)(CH 2 ) m COOH.
Claim 27
Dependent Claim
9 words
The compound of claim 1 wherein R is methyl.
Claim 28
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-methoxyethylsulfinylbenzene.
Claim 29
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5-methoxyethylsulfinylbenzene.
Claim 30
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-methylsulfinylbenzene.
Claim 31
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-thiocyanatobenzene.
Claim 32
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-iso-propylsulfinylbenzene.
Claim 33
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-n-propylsulfinylbenzene.
Claim 34
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-n-butylsulfinylbenzene.
Claim 35
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-phenoxybenzene.
Claim 36
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-ethylsulfinylbenzene.
Claim 37
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido-4-methoxymethoxybenzene.
Claim 38
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-ethoxymethoxybenzene.
Claim 39
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-methoxymethylthiobenzene.
Claim 40
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-4-methoxymethylsulfinylbenzene.
Claim 41
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-methylthiomethoxybenzene.
Claim 42
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-5-phenylsulfinylbenzene.
Claim 43
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-4-phenylsulfinylbenzene.
Claim 44
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido)-2-amino-5-phenylthiobenzene.
Claim 45
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 1-(3-methoxycarbonyl-2-thioureido-2-amino-4-phenylthiobenzene.
Claim 46
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 2-acetamido-1-(3-methoxycarbonyl-2-thioureido)-5-benzylthiobenzene.
Claim 47
Dependent Claim
10 words
The compound of claim 1 wherein R 1 is ##STR11##
Claim 48
Dependent Claim
10 words
The compound of claim 1 wherein R 1 is ##STR12##
Claim 49
Dependent Claim
10 words
The compound of claim 1 wherein R 7 is phenyl.
Claim 50
Dependent Claim
13 words
The compound of claim 1 wherein R 7 is either methyl or ethyl.
Claim 51
Dependent Claim
10 words
The compound of claim 1 wherein said compound is 2-amino-1-(3-methoxycarbonyl-2-thioureido)-5-methoxymethylsulfinylbenzene.
Claim 52
Dependent Claim
1 words
1,2-bis-(3-ethoxycarbonyl-2-thioureido)-4-phenylthiobenzene.
Claim 53
Dependent Claim
1 words
1,2-bis-(3-ethoxycarbonyl-2-thioureido)-4-phenylthiobenzene.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-06 | 1981-08-08 | 1982-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-06 | 1985-08-08 | 1986-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-06 | 1989-08-08 | 1990-02-07 | $7700.00 | Window Closed / Lapsed |