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US4338433A
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Moranoline derivatives and process for preparation thereof
Assignee: Nippon Shinyaku Co Ltd
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Filing: 1980-12-08
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Granted: 1982-07-06
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Expires: 2000-12-08
Abstract
Abstract Moranolines are produced which are useful for controlling blood sugar levels.
Inventors
- 👤 Shingo Matsumura
- 👤 Hiroshi Enomoto
- 👤 Yoshiaki Aoyagi
- 👤 Yoji Ezure
- 👤 Yoshiaki Yoshikuni
- 👤 Masahiro Yagi
- 👤 Nobutoshi Ojima
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 10:07
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/02
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
24 words
A moranoline derivative of the formula: ##STR9## wherein n is an integer of from 0 to 7, and R is H or lower alkyl.
Claim 2
Dependent Claim
24 words
A moranoline derivative of the formula: ##STR9## wherein n is an integer of from 0 to 7, and R is H or lower alkyl.
Claim 3
Dependent Claim
78 words
A process for the preparation of a moranoline derivative of the formula (I): ##STR10## wherein R is H or lower alkyl, and n is an integer of from 1 to 7, which comprises reacting an aqueous solution containing a moranoline of the formula (II): ##STR11## wherein R is as defined above and cyclodextrin or soluble starch with cyclodextrin glycosyltransferase to obtain a mixture containing a moranoline derivative of the formula (I) and isolating the mixture into respective components.
Claim 4
Dependent Claim
78 words
A process for the preparation of a moranoline derivative of the formula (I): ##STR10## wherein R is H or lower alkyl, and n is an integer of from 1 to 7, which comprises reacting an aqueous solution containing a moranoline of the formula (II): ##STR11## wherein R is as defined above and cyclodextrin or soluble starch with cyclodextrin glycosyltransferase to obtain a mixture containing a moranoline derivative of the formula (I) and isolating the mixture into respective components.
Claim 5
Dependent Claim
107 words
A process for the preparation of a glucosylmoranoline derivative of the formula ##STR12## wherein R is hydrogen or lower alkyl, which comprises reacting a solution of a mixture containing a compound of the formula (I): ##STR13## wherein R is as defined above and n is an integer of from 0 to 20, and a compound of the formula (IV): ##STR14## wherein R is as defined above, with the proviso that the case where a compound of the formula (I) in which n is zero is used alone as the compound of the formula (I) is excluded with α-1,4-glucanglucohydrolase directly or after addition of a cation exchange resin.
Claim 6
Dependent Claim
107 words
A process for the preparation of a glucosylmoranoline derivative of the formula ##STR12## wherein R is hydrogen or lower alkyl, which comprises reacting a solution of a mixture containing a compound of the formula (I): ##STR13## wherein R is as defined above and n is an integer of from 0 to 20, and a compound of the formula (IV): ##STR14## wherein R is as defined above, with the proviso that the case where a compound of the formula (I) in which n is zero is used alone as the compound of the formula (I) is excluded with α-1,4-glucanglucohydrolase directly or after addition of a cation exchange resin.
Claim 7
Dependent Claim
10 words
A moranoline according to claim 1 wherein R is H.
Claim 8
Dependent Claim
11 words
A moranoline according to claim 1 wherein R is lower alkyl.
Claim 9
Dependent Claim
10 words
A moranoline according to claim 1 wherein n is zero.
Claim 10
Dependent Claim
31 words
A process according to claim 2 wherein the reaction temperature is about 40° C. and the pH is from 5.0 to 8.5 for a reaction time of 1 to 3 days.
Claim 11
Dependent Claim
10 words
A moranoline according to claim 1 wherein R is methyl.
Claim 12
Dependent Claim
10 words
A process according to claim 2 wherein R is methyl.
Claim 13
Dependent Claim
10 words
A process according to claim 3 wherein R is methyl.
Claim 14
Dependent Claim
24 words
A process according to claim 3 wherein a cation exchange resin is added, said cation exchange resin being a strongly acidic cation exchange resin.
References Cited (Backward Citations)
US3553191A
Cited
JPS54106595A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-07-05 | 1986-01-04 | 1986-07-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-05 | 1990-01-04 | 1990-07-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-05 | 1994-01-04 | 1994-07-06 | $7700.00 | Window Closed / Lapsed |