US3948919A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-Hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl)pyridine preparation and intermediate compounds
Assignee: Pfizer Inc
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Filing: 1974-10-09
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Granted: 1976-04-06
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Expires: 1994-10-09
Abstract
Abstract Process for preparing 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl)pyridine and the acid addition salts thereof which are useful as β-adrenergic agonist bronchodilators in mammals, and the intermediate compounds 2-hydroxymethyl-3-benzyloxypyridine-6-epoxyethane, 2-phenyl-4H-pyrido[3,2-d]-1,3-dioxin-6-epoxyethane and 2,2-disubstituted-4H-pyrido[3,2-d]-1,3-dioxin-6-epoxyethanes.
Inventors
- 👤 Susumu Nakanishi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 16:40
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/65
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
50 words
A process for producing a compound selected from the group consisting of ##SPC5## and the pharmaceutically accepted acid addition salts thereof, comprising the steps of heating 2-phenyl-4H-pyrido[3,2-d]-1,3-dioxin-6-epoxyethane with at least a molar amount of t-butylamine, and acid hydrolyzing the resulting product at a pH of from about 1 to 6.
Claim 2
Dependent Claim
50 words
A process for producing a compound selected from the group consisting of ##SPC5## and the pharmaceutically accepted acid addition salts thereof, comprising the steps of heating 2-phenyl-4H-pyrido[3,2-d]-1,3-dioxin-6-epoxyethane with at least a molar amount of t-butylamine, and acid hydrolyzing the resulting product at a pH of from about 1 to 6.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein said pH is from 2 to 4.
Claim 4
Dependent Claim
18 words
The process of claim 1 wherein the heating step is carried out at 35° C. to reflux temperature.
Claim 5
Dependent Claim
22 words
The process of claim 1 wherein the heating setp is carried out in a closed system at reflux temperature at 85° C.
Claim 6
Dependent Claim
48 words
The process according to claim 2 wherein a mono- or diacid addition salt is formed by adding an acid selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, nitric, sulfuric, sulfurous, phorphoric, acetic, lactic, citric, tartaric, succinic, maleic and gluconic acids to the product obtained by acid hydrolysis.
Claim 7
Dependent Claim
73 words
A process for producing a compound selected from the group consisting of ##SPC6## and the pharmaceutically accepted acid addition salts thereof, comprising the steps of heating a compound selected from the group consisting of ##SPC7## wherein R and R' are each selected from the group consisting of methyl and phenyl, with at least a molar amount of t-butylamine, and acid hydrolyzing the resulting product at a pH of from about 1 to 6.
Claim 8
Dependent Claim
73 words
A process for producing a compound selected from the group consisting of ##SPC6## and the pharmaceutically accepted acid addition salts thereof, comprising the steps of heating a compound selected from the group consisting of ##SPC7## wherein R and R' are each selected from the group consisting of methyl and phenyl, with at least a molar amount of t-butylamine, and acid hydrolyzing the resulting product at a pH of from about 1 to 6.
Claim 9
Dependent Claim
13 words
The process of claim 6 wherein said pH is from 2 to 4.
Claim 10
Dependent Claim
18 words
The process of claim 6 wherein the heating step is carried out at 35° C. to reflux temperature.
Claim 11
Dependent Claim
48 words
The process of claim 6 wherein a mono- or diacid addition salt is formed by adding an acid selected from the group consisting of hydrobromic, hydroiodic, hydrochloric, nitric, sulfuric, sulfurous, phorphoric, acetic, lactic, citric, tartaric, succinic, maleic and gluconic acids to the product obtained by reaction with t-butylamine.
Claim 12
Dependent Claim
12 words
The process of claim 6 wherein R and R' are each methyl.
Claim 13
Dependent Claim
24 words
A compound selected from the group consisting of ##SPC8## wherein R and R' are each selected from the group consisting of methyl and phenyl.
Claim 14
Dependent Claim
24 words
A compound selected from the group consisting of ##SPC8## wherein R and R' are each selected from the group consisting of methyl and phenyl.
Claim 15
Dependent Claim
9 words
The compound of claim 11 of the formula ##SPC9##
Claim 16
Dependent Claim
6 words
A compound of the formula ##SPC10##
Claim 17
Dependent Claim
6 words
A compound of the formula ##SPC10##
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) | 1979-04-06 | 1979-10-06 | 1980-04-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-06 | 1983-10-06 | 1984-04-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-06 | 1987-10-06 | 1988-04-06 | $7700.00 | Window Closed / Lapsed |