Patent US4010178A successfully refreshed from Google Patents.
US4010178A
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Carbonic acid esters, and the preparation thereof and their use
Assignee: Astellas Pharma Inc
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Filing: 1975-08-26
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Granted: 1977-03-01
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Expires: 1995-08-26
Abstract
Abstract Carbonic acid esters of the formula substituent(s) substituents(s) R'.sub.1 OCOOR'.sub.2 wherein R' 1 is lower alkyl which may have substituent)s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituents)s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R' 2 is benzotriazolyl which may have halogen; or a group represented by the formula: ##STR1## wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R' 2 is a group represented by the formula: ##STR2## wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R' 1 is ar(lower) alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano. A process for the protection of amino and/or imino groups in compounds containing them by reacting them with the aforementioned esters is also disclosed.
Inventors
- 👤 Takashi Kamiya
- 👤 Masumi Itoh
- 👤 Daijiro Hagiwara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 09:00
CPC Classifications
C; C07; C07D; C07D249/00; C07D249/16; C07D249/18; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16; C07K; C07K1/00; C07K1/06
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
122 words
Carbonic acid esters of the formula: R'.sub.1 OCOOR'.sub.2 wherein R' 1 is lower alkyl which may have substituent(s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R' 2 is benzotriazolyl which may have halogen as a substituent; or a group represented by the formula: ##STR8##wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R' 2 is a group represented by the formula: ##STR9##wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R' 1 is ar(lower)alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano.
Claim 2
Dependent Claim
122 words
Carbonic acid esters of the formula: R'.sub.1 OCOOR'.sub.2 wherein R' 1 is lower alkyl which may have substituent(s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R' 2 is benzotriazolyl which may have halogen as a substituent; or a group represented by the formula: ##STR8##wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R' 2 is a group represented by the formula: ##STR9##wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R' 1 is ar(lower)alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano.
Claim 3
Dependent Claim
33 words
The compounds according to claim 1, wherein R' 2 is a group represented by the formula: ##STR10##wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl.
Claim 4
Dependent Claim
59 words
The compounds according to claim 2, wherein R' 1 is lower alkyl, or ar(lower)alkyl having lower alkoxy, and R' 2 is a group represented by the formula: ##STR11##wherein Y' is esterified carboxy or aroyl and Z' is esterified carboxy or lower alkanoyl; provided that when Y' and Z' are both esterified carboxy, R' 1 is ar(lower)alkyl having lower alkoxy.
Claim 5
Dependent Claim
23 words
The compounds according to claim 3, wherein R' 1 is lower alkyl, Y' is esterified carboxy or aroyl and Z' is lower alkanoyl.
Claim 6
Dependent Claim
13 words
The compounds according to claim 4, wherein Y' is lower alkoxycarbonyl or aroyl.
Claim 7
Dependent Claim
20 words
The compounds according to claim 5, wherein R' 1 is tert-butyl, Y' is ethoxycarbonyl, or benzoyl and Z' is acetyl.
Claim 8
Dependent Claim
10 words
The compound according to claim 6, wherein Y' is ethoxycarbonyl.
Claim 9
Dependent Claim
10 words
The compound according to claim 6, wherein Y' is benzoyl.
Claim 10
Dependent Claim
22 words
The compounds according to claim 3, wherein R' 1 is ar(lower)alkyl having lower alkoxy, and Y' and Z' are both esterified carboxy.
Claim 11
Dependent Claim
14 words
The compounds according to claim 9, wherein Y' and Z' are both lower alkoxycarbonyl.
Claim 12
Dependent Claim
20 words
The compounds according to claim 10, wherein R' 1 is benzyl having methoxy, and Y' and Z' are both ethoxycarbonyl.
Claim 13
Dependent Claim
11 words
The compound according to claim 11, wherein R' 1 is 4-methoxybenzyl.
Claim 14
Dependent Claim
26 words
The compounds according to claim 1, wherein R' 1 is lower alkyl or ar(lower)alkyl and R' 2 is benzotriazolyl which may have halogen as a substituent.
Claim 15
Dependent Claim
26 words
The compounds according to claim 13, wherein R' 1 is ethyl, tert-butyl or benzyl and R' 2 is benzotriazolyl which may have chlorine as a substituent.
Claim 16
Dependent Claim
13 words
The compounds according to claim 14, wherein R' 2 is 1H-benzotriazol-1-yl or 6-chloro-1H-benzotriazol-1-yl.
Claim 17
Dependent Claim
16 words
The compound according to claim 15, wherein R' 1 is ethyl and R' 2 is 6-chloro-1H-benzotriazol-1-yl.
Claim 18
Dependent Claim
16 words
The compound according to claim 15, wherein R' 1 is tert-butyl and R' 2 is 6-chloro-1H-benzotriazol-1-yl.
Claim 19
Dependent Claim
16 words
The compound according to claim 15, wherein R' 1 is benzyl and R' 2 is 1H-benzotriazol-1-yl.
Claim 20
Dependent Claim
208 words
A process for preparing carbonic acid esters of the formula: R'.sub.1 OCOOR'.sub.2 wherein R' 1 is lower alkyl which may have substituent(s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R' 2 is benzotriazolyl which may have halogen as a substituent; or a group represented by the formula: ##STR12##wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R' 2 is a group represented by the formula: ##STR13##wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R' 1 is ar(lower)alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano; which comprises a. reacting a haloformic acid ester of the formula: X--COOR'.sub.2 wherein X is halogen and R' 2 is as defined above, with a hydroxy-compound of the formula: R'.sub.1 -- OH wherein R' 1 is as defined above, or b. reacting a formic acid ester of the formula: R'.sub.1 --OCOX' wherein R' 1 is as defined above and X' is halogen, with a compound of the formula: R'.sub.2 -- OH wherein R' 2 is as defined above or a salt thereof.
Claim 21
Dependent Claim
208 words
A process for preparing carbonic acid esters of the formula: R'.sub.1 OCOOR'.sub.2 wherein R' 1 is lower alkyl which may have substituent(s) selected from the group of halogen, lower alkoxy and aryloxy, or ar(lower)-alkyl which may have substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano, and R' 2 is benzotriazolyl which may have halogen as a substituent; or a group represented by the formula: ##STR12##wherein Y' and Z' are each cyano, nitro, carbamoyl, esterified carboxy, lower alkanoyl, aroyl or disubstituted carbamoyl; provided that when R' 2 is a group represented by the formula: ##STR13##wherein Y' and Z' are each cyano, nitro, carbamoyl or esterified carboxy, R' 1 is ar(lower)alkyl having substituent(s) selected from the group of lower alkoxy, halogen, nitro and cyano; which comprises a. reacting a haloformic acid ester of the formula: X--COOR'.sub.2 wherein X is halogen and R' 2 is as defined above, with a hydroxy-compound of the formula: R'.sub.1 -- OH wherein R' 1 is as defined above, or b. reacting a formic acid ester of the formula: R'.sub.1 --OCOX' wherein R' 1 is as defined above and X' is halogen, with a compound of the formula: R'.sub.2 -- OH wherein R' 2 is as defined above or a salt thereof.
Claim 22
Dependent Claim
23 words
Compounds according to claim 1 wherein R' 1 is lower alkyl and R' 2 is benzotriazolyl which may have halogen as a substituent.
Claim 23
Dependent Claim
25 words
Compounds according to claim 20 wherein R' 1 is ethyl or tertiary butyl and R' 2 is benzotriazolyl which may have chlorine as a substituent.
Claim 24
Dependent Claim
12 words
Compounds according to claim 21 wherein R' 2 is 1H-benzotriazol-1-yl or 6-chloro-1H-benzotriazol-1-yl.
References Cited (Backward Citations)
US3189615A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-29 | 1980-08-30 | 1981-03-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-29 | 1984-08-30 | 1985-03-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-29 | 1988-08-30 | 1989-03-01 | $7700.00 | Window Closed / Lapsed |