US3962447A
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Novel pro-drug derivatives of pyridinium aldoxime type cholinesterase reactivators and method of using same
Assignee: Interx Research Corp
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Filing: 1975-08-11
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Granted: 1976-06-08
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Expires: 1995-08-11
Abstract
Abstract There is provided, novel pro-drug forms of pyridinium aldoxime type cholinesterase reactivators, namely, dihydropyridinium aldoximes, having the formula:
Inventors
- 👤 Takeru Higuchi
- 👤 Nicolae S. Bodor
- 👤 Efraim Shek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 19:00
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/82
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
178 words
A pharmaceutical composition for reactivating blocked cholinesterase in a warm-blooded animal and suitable for oral administration and absorption through the small intestine of said warm-blooded animal, comprising an effective cholinesterase reactivating amount of a pro-drug compound of the pyridine aldoxime-(hydroxyiminomethyl pyridinium) type capable of reactivating blocked cholinesterase having the formula: ##SPC17## wherein R represents a member selected from the group consisting of an alkyl (C 1 -C 4 ) group, a ##SPC18## group, a ##SPC19## group, ##SPC20## group, and a ##SPC21## group, wherein Z represents a member selected from the group consisting of a --CH 2 --CH 2 -- group, a --CH 2 --O--CH 2 -- group, a --CH 2 CH 2 OCH 2 CH 2 -- group, and a --CH 2 O--CH 2 --CH 2 --O--CH 2 -- group; wherein R 1 represents a member selected from the group consisting of a hydrogen atom, a methyl group, an acyl group and a ##EQU3## group; and wherein X - represents an anion derived from a pharmaceutically acceptable acid addition salt in combination with a pharmaceutically acceptable enteric carrier.
Claim 2
Dependent Claim
178 words
A pharmaceutical composition for reactivating blocked cholinesterase in a warm-blooded animal and suitable for oral administration and absorption through the small intestine of said warm-blooded animal, comprising an effective cholinesterase reactivating amount of a pro-drug compound of the pyridine aldoxime-(hydroxyiminomethyl pyridinium) type capable of reactivating blocked cholinesterase having the formula: ##SPC17## wherein R represents a member selected from the group consisting of an alkyl (C 1 -C 4 ) group, a ##SPC18## group, a ##SPC19## group, ##SPC20## group, and a ##SPC21## group, wherein Z represents a member selected from the group consisting of a --CH 2 --CH 2 -- group, a --CH 2 --O--CH 2 -- group, a --CH 2 CH 2 OCH 2 CH 2 -- group, and a --CH 2 O--CH 2 --CH 2 --O--CH 2 -- group; wherein R 1 represents a member selected from the group consisting of a hydrogen atom, a methyl group, an acyl group and a ##EQU3## group; and wherein X - represents an anion derived from a pharmaceutically acceptable acid addition salt in combination with a pharmaceutically acceptable enteric carrier.
Claim 3
Dependent Claim
21 words
The composition of claim 1, wherein said compound is: 1-Methyl-1,6-dihydropyridine-2-aldoxime and its HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 4
Dependent Claim
21 words
The composition of claim 1, wherein said compound is: Trimethylene-bis-[1-(dihydropyridine-4-carbaldoxime)] and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 5
Dependent Claim
21 words
The composition of claim 3, wherein said compound is: Trimethylene-bis-[1-(1,4-dihydropyridine-4-carbaldoxime] and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 6
Dependent Claim
21 words
The composition of claim 3, wherein said compound is: Trimethylene-bis-[(1,6-dihydropyridine-4-carbaldoxime] and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 7
Dependent Claim
22 words
The composition of claim 1, wherein said compound is: Bis-(4-hydroxyiminomethyl-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 8
Dependent Claim
22 words
The composition of claim 6, wherein said compound is: Bis-(4-hydroxyiminomethyl-1,4-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 9
Dependent Claim
22 words
The composition of claim 6, wherein said compound is: Bis-(4-hydroxyiminomethyl-1,6-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 10
Dependent Claim
22 words
The composition of claim 1, wherein said compound is: Bis-(2-hydroxyiminomethyl-1,6-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 11
Dependent Claim
22 words
The composition of claim 1, wherein said compound is: Bis-[2-(4-hydroxyiminomethyl-dihydropyridino)ethyl] ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 12
Dependent Claim
23 words
The composition of claim 10, wherein said compound is: Bis-[2-(4-hydroxyiminomethyl-1,4-dihydropyridino) ethyl] ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 13
Dependent Claim
23 words
The composition of claim 10, wherein said compound is: Bis-[2-(4-hydroxyiminomethyl-1,6-dihydropyridino) ethyl] ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 14
Dependent Claim
23 words
The composition of claim 1, wherein said compound is: Ethylene glycol-bis-(4-hydroxyiminomethyl-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 15
Dependent Claim
23 words
The composition of claim 13, wherein said compound is: Ethylene glycol-bis-(4-hydroxyiminomethyl-1,4-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 16
Dependent Claim
23 words
The composition of claim 13, wherein said compound is: Ethylene glycol-bis-(4-hydroxyiminomethyl-1,6-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 17
Independent Claim
165 words
A method for reactivating blocked cholinesterase in a warm-blooded animal as a result of anticholinesterase compound poisoning, which comprises: administering thereto, an effective cholinesterase reactivating amount of a pro-drug compound of the pyridine aldoxime (hydroxyiminomethyl pyridinium) type capable of reactivating blocked cholinesterase having the formula: ##SPC22## wherein R represents a member selected from the group consisting of an alkyl (C 1 -C 4 ) group, a ##SPC23## group, a ##SPC24## group, ##SPC25## group and a ##SPC26## group, wherein Z represents a member selected from the group consisting of a --CH 2 --CH 2 -- group, a --CH 2 --O--CH 2 -- group, a --CH 2 CH 2 OCH 2 CH 2 -- group, and a --CH 2 O--CH 2 --CH 2 --O--CH 2 -- group; wherein R 1 represents a member selected from the group consisting of a hydrogen atom, a methyl group, an acyl group and a ##EQU4## group; and wherein X - represents an anion derived from a pharmaceutically acceptable acid addition salt.
Claim 18
Independent Claim
165 words
A method for reactivating blocked cholinesterase in a warm-blooded animal as a result of anticholinesterase compound poisoning, which comprises: administering thereto, an effective cholinesterase reactivating amount of a pro-drug compound of the pyridine aldoxime (hydroxyiminomethyl pyridinium) type capable of reactivating blocked cholinesterase having the formula: ##SPC22## wherein R represents a member selected from the group consisting of an alkyl (C 1 -C 4 ) group, a ##SPC23## group, a ##SPC24## group, ##SPC25## group and a ##SPC26## group, wherein Z represents a member selected from the group consisting of a --CH 2 --CH 2 -- group, a --CH 2 --O--CH 2 -- group, a --CH 2 CH 2 OCH 2 CH 2 -- group, and a --CH 2 O--CH 2 --CH 2 --O--CH 2 -- group; wherein R 1 represents a member selected from the group consisting of a hydrogen atom, a methyl group, an acyl group and a ##EQU4## group; and wherein X - represents an anion derived from a pharmaceutically acceptable acid addition salt.
Claim 19
Dependent Claim
21 words
The method of claim 16, wherein said compound is: 1-Methyl-1,6-dihydropyridine-2-aldoxime and its HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 20
Dependent Claim
21 words
The method of claim 16, wherein said compound is: Trimethylene-bis-[1-(dihydropyridine-4-carbaldoxime)] and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 21
Dependent Claim
21 words
The method of claim 18, wherein said compound is: Trimethylene-bis-[1-(1,4-dihydropyridine-4-carbaldoxime] and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 22
Dependent Claim
21 words
The method of claim 18, wherein said compound is: Trimethylene-bis-[(1,6-dihydropyridine-4-carbaldoxime] and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 23
Dependent Claim
22 words
Th method of claim 16, wherein said compound is: Bis-(4-hydroxyiminomethyl-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 24
Dependent Claim
22 words
The method of claim 21, wherein said compound is: Bis-(4-hydroxyiminomethyl-1,4-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptble anion.
Claim 25
Dependent Claim
22 words
The method of claim 21, wherein said compound is: Bis-(4-hydroxyiminomethyl-1,6-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 26
Dependent Claim
22 words
The method of claim 16, wherein said compound is: Bis-(2-hydroxyiminomethyl-1,6-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 27
Dependent Claim
23 words
The method of claim 16, wherein said compound is: Bis-[2-(4-hydroxyiminomethyl-dihydropyridino) ethyl] ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 28
Dependent Claim
23 words
The method of claim 25, wherein said compound is: Bis-[2-(4-hydroxyiminomethyl-1,4-dihydropyridino) ethyl] ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 29
Dependent Claim
24 words
The method of claim 25, wherein said compound is: Bis-[2-(4-hydroxyiminomethyl-1,6-dihydropyridino) ethyl ] ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 30
Dependent Claim
23 words
The method of claim 16, wherein said compound is: Ethylene glycol-bis-(4-hydroxyiminomethyl-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 31
Dependent Claim
23 words
The method of claim 28, wherein said compound is: Ethylene glycol-bis-(4-hydroxyiminomethyl-1,4-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 32
Dependent Claim
23 words
The method of claim 28, wherein said compound is: Ethylene glycol-bis-(4-hydroxyiminomethyl-1,6-dihydropyridine-1-methyl) ether and its di-HX salts, wherein X represents a pharmaceutically acceptable anion.
Claim 33
Dependent Claim
18 words
The method of claim 16, wherein said compound is maintained in combination with a pharmaceutically acceptable enteric carrier.
Claim 34
Dependent Claim
18 words
The method of claim 16, wherein said compound is maintained in combination with a pharmaceutically acceptable parenteral vehicle.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-08 | 1979-12-08 | 1980-06-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-08 | 1983-12-08 | 1984-06-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-08 | 1987-12-08 | 1988-06-08 | $7700.00 | Window Closed / Lapsed |