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Patent US3933830A successfully refreshed from Google Patents.
US3933830A
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Process for the synthesis of 4-(2-pyridylamido ethyl) piperidines
Assignee: Pfizer Inc
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Filing: 1974-09-10
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Granted: 1976-01-20
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Expires: 1994-09-10
Abstract
Abstract Disclosed herein is an improved process for the preparation of known hypoglycemic piperidinesulfamylureas of the structure OO PARALLEL PARALLEL R-CNH(CH2)2-SO2NHC-NHR' wherein R is selected from the group consisting of 3-(2-methoxy)pyridyl, 3-(2-ethoxy)pyridyl and 2-(4-chloro)pyridyl and R' is selected from the group consisting of bicyclo[2.2.1]hept-5-en-2-yl-endo-methyl, bicyclo[2.2.1]hept-2-yl-endo-methyl, 7-oxabicyclo[2.2.1]hept-2-yl-methyl, 1-adamantyl and cycloalkyl having from five to eight carbon atoms.
Inventors
- 👤 Wayne E. Barth
- 👤 Donald E. Kuhla
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 23:08
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/81; C07D213/82; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44; A61K31/445; C07D401/00; C07D401/02; C07D401/12
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
64 words
A process for preparing a 4-(2-pyridylamidoethyl)piperidine of the structure ##EQU5## wherein R is selected from the group consisting of 3-(2-methoxy) pyridyl, 3-(2-ethoxy)pyridyl and 2-(4-chloro)pyridyl comprising contacting the corresponding 4-(2-pyridylamidoethyl)pyridine in reaction-inert solvent with hydrogen at about 25 to 75 psig. and about 15° to 40°C. in the presence of noble metal catalyst and a substantially equimolar portion of acid until reaction is substantially complete.
Claim 2
Dependent Claim
64 words
A process for preparing a 4-(2-pyridylamidoethyl)piperidine of the structure ##EQU5## wherein R is selected from the group consisting of 3-(2-methoxy) pyridyl, 3-(2-ethoxy)pyridyl and 2-(4-chloro)pyridyl comprising contacting the corresponding 4-(2-pyridylamidoethyl)pyridine in reaction-inert solvent with hydrogen at about 25 to 75 psig. and about 15° to 40°C. in the presence of noble metal catalyst and a substantially equimolar portion of acid until reaction is substantially complete.
Claim 3
Dependent Claim
10 words
The process of claim 1 wherein R is 3-(2-methoxy) pyridyl.
Claim 4
Dependent Claim
11 words
The process of claim 1 wherein said acid is hydrochloric acid.
Claim 5
Dependent Claim
11 words
The process of claim 1 wherein said acid is sulfuric acid.
Claim 6
Dependent Claim
11 words
The process of claim 1 wherein said solvent is lower alkanol.
Claim 7
Dependent Claim
10 words
The process of claim 5 wherein said solvent is methanol.
Claim 8
Dependent Claim
11 words
The process of claim 1 wherein said catalyst is platinum oxide.
Claim 9
Dependent Claim
174 words
A process for preparing a 4-(2-pyridylamidoethyl)piperidine of the structure ##EQU6## wherein R is selected from the group consisting of 3-(2-methoxy) pyridyl, 3-(2-ethoxy)pyridyl and 2-(4-chloro)pyridyl comprising contacting the corresponding 4-(2-pyridylamidoethyl)pyridine with a substantially equimolar portion of an agent chosen from the group consisting of benzyl bromide, benzyl iodide, the α-bromo- and α-iodoxylyenes, the α-bromo- and α-iodomethylnaphthalenes and the mono- and disubstituted derivaties thereof wherein said substituents are chosen from the group consisting of lower alkyl, lower alkoxy, phenyl and phenoxy, in reaction-inert solvent at reflux temperature until reaction to form the corresponding N-substituted-4-(2-pyridylamidoethyl)pyridinium salt is substantially complete; contacting said salt with metal hydride selected from the group consisting of sodium borohydride, lithium aluminum hydride and sodium bis-(2-methoxyethoxy)aluminum hydride in reaction-inert solvent until reaction to form the corresponding N-substituted-4-(2-pyridylamidoethyl)-1,2,5,6-tetrahydropyridine is substantially complete; and contacting said tetrahydropyridine with hydrogen at up to about 400 psig. from about 40° to 75°C. in reaction-inert solvent in the presence of moble metal catalyst and an approximately equimolar portion of acid until reaction to form the corresponding 4-(2-pyridylamidoethyl)piperidine is substantially complete.
Claim 10
Dependent Claim
174 words
A process for preparing a 4-(2-pyridylamidoethyl)piperidine of the structure ##EQU6## wherein R is selected from the group consisting of 3-(2-methoxy) pyridyl, 3-(2-ethoxy)pyridyl and 2-(4-chloro)pyridyl comprising contacting the corresponding 4-(2-pyridylamidoethyl)pyridine with a substantially equimolar portion of an agent chosen from the group consisting of benzyl bromide, benzyl iodide, the α-bromo- and α-iodoxylyenes, the α-bromo- and α-iodomethylnaphthalenes and the mono- and disubstituted derivaties thereof wherein said substituents are chosen from the group consisting of lower alkyl, lower alkoxy, phenyl and phenoxy, in reaction-inert solvent at reflux temperature until reaction to form the corresponding N-substituted-4-(2-pyridylamidoethyl)pyridinium salt is substantially complete; contacting said salt with metal hydride selected from the group consisting of sodium borohydride, lithium aluminum hydride and sodium bis-(2-methoxyethoxy)aluminum hydride in reaction-inert solvent until reaction to form the corresponding N-substituted-4-(2-pyridylamidoethyl)-1,2,5,6-tetrahydropyridine is substantially complete; and contacting said tetrahydropyridine with hydrogen at up to about 400 psig. from about 40° to 75°C. in reaction-inert solvent in the presence of moble metal catalyst and an approximately equimolar portion of acid until reaction to form the corresponding 4-(2-pyridylamidoethyl)piperidine is substantially complete.
Claim 11
Dependent Claim
11 words
The process of claim 8 wherein said agent is benzyl bromide.
Claim 12
Dependent Claim
12 words
The process of claim 9 wherein said agent is dissolved in acetonitrile.
Claim 13
Dependent Claim
12 words
The process of claim 8 wherein said metal hydride is sodium borohydride.
Claim 14
Dependent Claim
10 words
The process of claim 8 wherein said catalyst is palladium.
Claim 15
Dependent Claim
17 words
The process of claim 8 wherein contact with said metal hydride and hydrogen is effected in methanol.
Claim 16
Dependent Claim
10 words
The process of claim 11 wherein R is 3-(2-methoxy) pyridyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-19 | 1979-07-21 | 1980-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-19 | 1983-07-21 | 1984-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-19 | 1987-07-21 | 1988-01-20 | $7700.00 | Window Closed / Lapsed |