US4156777A
Expired / Lapsed
US
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Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein
Assignee: Tanabe Pharma Corp
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Filing: 1978-01-26
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Granted: 1979-05-29
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Expires: 1998-01-26
Abstract
Abstract Glucopyranose-nitrosourea compounds having lower alkyl group and/or 2-chloroethyl group as substituent(s), are produced at high yield by reacting amino-glucopyranose compounds having lower alkoxy group and/or amino group(s) (or an acid-added amino group) as substituent(s), with o-nitro- or o-cyano-phenyl N-substituted-N-nitrosocarbamate compounds having lower alkyl group or 2-chloroethyl group as substituent. 1-(Lower alkyl or 2-chloroethyl)-3-(D-glucopyranos-6-yl)-1-nitrosourea compounds included within the scope of the nitrosourea compounds are novel. The nitrosourea compounds produced by this invention all show antitumor activity, among which the novel compounds exhibit excellent physical and pharmacological properties.
Inventors
- 👤 Goro Kimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 07:04
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/12; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
50 words
Process for the production of glucopyranosenitrosourea compounds having the general formula: ##STR11## which comprises reacting an amino-glucopyranose compound having the general formula: ##STR12## with a substituted-phenyl N-substituted-N-nitrosocarbamate compound having the general formula ##STR13## (in which R 7 represents a nitro or cyano group and R 8 is as hereinbefore defined).
Claim 2
Dependent Claim
50 words
Process for the production of glucopyranosenitrosourea compounds having the general formula: ##STR11## which comprises reacting an amino-glucopyranose compound having the general formula: ##STR12## with a substituted-phenyl N-substituted-N-nitrosocarbamate compound having the general formula ##STR13## (in which R 7 represents a nitro or cyano group and R 8 is as hereinbefore defined).
Claim 3
Dependent Claim
45 words
Process as claimed in claim 1, wherein a compound of formula IV is used in which R 4 is hydroxy or alkoxy having from 1 to 4 carbon atoms; R 5 is amino or an acid addition salt formed therefrom; and R 6 is hydroxy.
Claim 4
Dependent Claim
45 words
Process as claimed in claim 1, wherein a compound of formula IV is used in which R 4 is hydroxy or alkoxy having from 1 to 4 carbon atoms; and each of R 5 and R 6 is amino or an acid-addition salt formed therefrom.
Claim 5
Dependent Claim
44 words
Process as claimed in claim 1 wherein a compound of formula IV is used in which R 4 is hydroxy or alkoxy having from 1 to 4 carbon atoms; R 5 is hydroxy; and R 6 is amino or an acid-addition salt formed therefrom.
Claim 6
Dependent Claim
37 words
Process as claimed in claim 1, wherein a compound of formula IV is used in which R 4 is amino or an acid addition salt formed therefrom; and each of R 5 and R 6 is hydroxy.
Claim 7
Dependent Claim
29 words
Process as claimed in claim 1, wherein R 4 in the compound of formula IV is one member selected from the group consisting of methoxy, ethoxy, n=propoxy and n-butoxy.
Claim 8
Dependent Claim
17 words
Process as claimed in claim 1, wherein at least one acid-addition salt is formed from weak acids.
Claim 9
Dependent Claim
13 words
Process as claimed in claim 7, wherein the weak acid is carbonic acid.
Claim 10
Dependent Claim
22 words
Process as claimed in claim 6, wherein a compound of formula V is used in which R 7 is a nitro group.
Claim 11
Dependent Claim
22 words
Process as claimed in claim 7, wherein a compound of formula V is used in which R 7 is a nitro group.
Claim 12
Dependent Claim
22 words
Process as claimed in claim 6, wherein a compound of formula V is used in which R 7 is a cyano group.
Claim 13
Dependent Claim
22 words
Process as claimed in claim 7, wherein a compound of formula V is used in which R 7 is a cyano group.
Claim 14
Dependent Claim
20 words
Process as claimed in claim 10, wherein the reaction is effected at a temperature of not more than 60° C.
Claim 15
Dependent Claim
20 words
Process as claimed in claim 3, wherein the reaction is effected at a temperature of not more than 60° C.
Claim 16
Dependent Claim
20 words
Process as claimed in claim 4, wherein the reaction is effected at a temperature of not more than 80° C.
Claim 17
Dependent Claim
20 words
Process as claimed in claim 5, wherein the reaction is effected at a temperature of not more than 30° C.
Claim 18
Dependent Claim
50 words
Process as claimed in claim 13, wherein the reaction is effected in the presence of a mixture of one member selected from the group consisting of methanol, ethanol and isopropanol with one member selected from the group consisting of tetrahydrofuran, toluene, dioxane, benzene, ethylacetate, isopropyl ether, dimethylformamide and dimethyl sulfoxide.
Claim 19
Dependent Claim
48 words
Process as claimed in claim 14, wherein the reaction is effected in the presence of a mixture of one member selected from the group consisting of methanol, ethanol and isopropanol with one member selected from the group consisting of tetrahydrofuran, toluene, dioxane, ethylacetate, acetonitrile, dimethylformamide and dimethyl sulfoxide.
Claim 20
Dependent Claim
52 words
Process as claimed in claim 15, wherein the reaction is effected in the presence of a mixture of one member selected from the group consisting of methanol, ethanol and isopropanol with one member selected from the group consisting of tetrahydrofuran, toluene, dioxane, benzene, ethylacetate, methylene chloride, carbon tetrachloride, dimethylformamide and dimethyl sulfoxide.
Claim 21
Dependent Claim
45 words
Process as claimed in claim 16, wherein the reaction is effected in the presence of a mixture of one member selected from the group consisting of methanol, ethanol and isopropanol with one member selected from the group consisting of tetrahydrofuran, dioxane, benzene, ethylacetate, and dimethylformamide.
Claim 22
Dependent Claim
28 words
1-(Alkyl or 2-chloroethyl)-3-(D-glucopyranos-6-yl)-1-nitrosourea compounds having the general formula: ##STR14## in which R 8 represents an alkyl group having from 1 to 4 carbon atoms or a 2-chloroethyl group.
Claim 23
Dependent Claim
28 words
1-(Alkyl or 2-chloroethyl)-3-(D-glucopyranos-6-yl)-1-nitrosourea compounds having the general formula: ##STR14## in which R 8 represents an alkyl group having from 1 to 4 carbon atoms or a 2-chloroethyl group.
Claim 24
Dependent Claim
23 words
Compounds as claimed in claim 21, wherein R 8 is any member selected from the group consisting of ethyl, methyl, n-propyl and n-butyl.
References Cited (Backward Citations)
US4057684A
Cited
US4086415A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |