GB1414841A

GB1414841A – 2,5-anhydro-dalloses derivatives thereof and c-glycosylnucleosides derived therefrom
– Google Patents

GB1414841A – 2,5-anhydro-dalloses derivatives thereof and c-glycosylnucleosides derived therefrom
– Google Patents
2,5-anhydro-dalloses derivatives thereof and c-glycosylnucleosides derived therefrom

Info

Publication number
GB1414841A

GB1414841A
GB585873A
GB585873A
GB1414841A
GB 1414841 A
GB1414841 A
GB 1414841A
GB 585873 A
GB585873 A
GB 585873A
GB 585873 A
GB585873 A
GB 585873A
GB 1414841 A
GB1414841 A
GB 1414841A
Authority
GB
United Kingdom
Prior art keywords
compounds
compound
yield
groups
benzoyl
Prior art date
1972-02-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
GB585873A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Syntex USA LLC

Original Assignee
Syntex USA LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1972-02-11
Filing date
1973-02-06
Publication date
1975-11-19

1973-02-06
Application filed by Syntex USA LLC
filed
Critical
Syntex USA LLC

1975-11-19
Publication of GB1414841A
publication
Critical
patent/GB1414841A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids

C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids

C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids

C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids

C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals

C07H15/02—Acyclic radicals, not substituted by cyclic structures

C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals

C07H15/18—Acyclic radicals, substituted by carbocyclic rings

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals

C07H15/20—Carbocyclic rings

C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS

C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof

C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen

C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom

C07H19/052—Imidazole radicals

Abstract

1414841 2,5-anhydro-D-alloses and their nucleosides SYNTEX (USA) Inc 6 Feb 1973 [11 Feb 1972] 5858/73 Heading C2C Novel compounds I in which OR3 is a hydrolyazble C 1-12 acyloxy group, t-butoxy, tetrahydropyran-21-yloxy, 41– methoxytetrahydropyran-21-yloxy, benzyloxy (optionally substituted by nitro, halo, C 1-6 alkyl or C 1-6 alkoxy) and OR1 and OR2 are the same and are selected from the groups for OR3 or together form an alkylenedioxy or cycloalkylidenedioxy group of up to 10 C atoms and R is phenyl optionally substituted by nitro, halo, C 1-6 alkyl or C 1-6 alkoxy are prepared from compound A in which R 9 is benzoyl (optionally substituted). Compound A is heated with dry halogen bromide in benzene and the product formed reacted with mercuric cyanide is nitromethane, to form a compound B in which R 10 is benzoyl. The free hydroxy (R 10 =H) compound is formed by reaction with sodium methoxide and neutralization. This is treated with isobutylene in concentrated sulphuric acid, or with dehydropyran or 4-methoxy 5,6-dihydro-2H-pyran in the presence of toluenesulphonic acid to yield the respective ether groups (R 10 =t-butyl, tetrahydropyran-2-yl or 4-methoxy-tetrahydropyran-4-yl). Compounds B are reacted with sodium hypophosphite and Raney nickel in pyridine/water/acetic acid and with an N,N1-diphenylethylenediamine to form a compound I in which R1, R2, R3 are benzoyl, butyl or the above pyranyl groups. Compounds I (R1, R2, R3=benzoyl) are hydrolysed and treated with (a) sodium hydride in dimethyl sulphoxide followed by benzyl chloride to form compounds I in which R1, R2 and R3 are benzyl or (b) a carboxylic acid anhydride in pyridene to form compounds I in which R1 R2 and R3 are acyl. Treatment of compounds I (R1, R2, R3= benzoyl) with methanolic ammonia gives the 2,3- dehydroxy compound which is reacted with a ketone and the corresponding acetal in the presence of perchloric acid to yield compounds I in which R 2 and R 3 are alkylidene or cycloalkylidene. Novel compounds III in which R4 is 3(5)-carboxy-4-pyrazolyl, 3,5- dicarboxy-4-pyrazolyl, 5-carboxy-3-isoxazolyl, 4,5-dicarboxy-3-isoxazolyl or a hydrolysable ester containing up to 12 C atoms or the amide thereof, OR7 is hydroxy, C 1-12 hydrolysable acyloxy group, t-butoxy tetrahydropyran-2- yloxy, 4-methoxytetrahydropyran-4-yloxy benzyloxy (optionally substituted by nitro, halo, C 1-6 alkyl or C 1-6 alkoxy) and OR5 and OR6 are the same and are selected from the groups OR7 or are together alkylidene or cycloalkylidene of up to 10C atoms are obtained from compounds I Thus Compound VIII is prepared by reacting a novel Compound II (prepared from Compounds I by method claimed in 50993/74 (Specification 1,414,842) with carbomethoxymethylene triphenyl phosphorane to form a compound IV which upon reaction with diazomethane yields the corresponding 2-pyrazoline which is halogenated and dehydrohalogenated with chlorine in CCl 4 to yield a Compound V which yields the methyl ester of Compound VIII by one of the following treatments: (1) when OR1, OR2 and OR3 are ester groups with a sodium methoxide and a cation exchange resin in hydrogen form (2) when OR1, OR2 and OR3 are benzyloxy, with ethanol containing 10% of (10% Pd on BaSO 4 ) and hydrogen with vigorous stirring, (3) when OR1, OR2 and OR3 are the remaining groups with 90% trifluoroacetic acid at room temperature. Treatment of compound (V) or the methyl ester of compound VIII with methanolic ammonia yields the amide of compound VIII. Treatment of the methyl ester with sodium hydroxide gives the free carboxylic acid VIII. Compounds (IX) in which R 12 is carboxy, a C 1-12 acyloxy group or carboxamido are prepared by reacting compounds IV with ethyl diazoacetate to yield a 2-pyrazolidine which undergo a similar set of reactions as above to yield compounds IX. Compounds XIII and XV in which R 13 and R 14 are carboxy. C 1-12 acyloxy or carboxamido are prepared by reacting aldehyde II with hydroxylamine hydrochloride and the resulting oxime is chlorinated in a diethyl ether solution to give an oximino chloride which upon reaction with (a) ethyl propiolate in the presence of triethylamine gives a 5-carbethoxy-3-isoxazole derivative or with (b) dimethylacetylene dicarboxylate in the presence of triethylamine forms the 4,5-dicarbmethoxy-3- isoxazole derivative. These derivatives undergo reactions as described above to yield the various compounds XIII and XIV. Compounds III are anti-metabolic, antibacterial and anti-viral agents and form with an excipient a pharmaceutical composition.

GB585873A
1972-02-11
1973-02-06
2,5-anhydro-dalloses derivatives thereof and c-glycosylnucleosides derived therefrom

Expired

GB1414841A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US22561372A

1972-02-11
1972-02-11

Publications (1)

Publication Number
Publication Date

GB1414841A
true

GB1414841A
(en)

1975-11-19

Family
ID=22845555
Family Applications (2)

Application Number
Title
Priority Date
Filing Date

GB585873A
Expired

GB1414841A
(en)

1972-02-11
1973-02-06
2,5-anhydro-dalloses derivatives thereof and c-glycosylnucleosides derived therefrom

GB5099374A
Expired

GB1414842A
(en)

1972-02-11
1973-02-06
2,5-anhydro-d-alloses

Family Applications After (1)

Application Number
Title
Priority Date
Filing Date

GB5099374A
Expired

GB1414842A
(en)

1972-02-11
1973-02-06
2,5-anhydro-d-alloses

Country Status (5)

Country
Link

JP
(1)

JPS4891053A
(en)

DE
(1)

DE2305894A1
(en)

ES
(1)

ES411472A1
(en)

FR
(1)

FR2181721B1
(en)

GB
(2)

GB1414841A
(en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

JP2006524227A
(en)

*

2003-03-28
2006-10-26
ファーマセット，インク．

Compounds for the treatment of Flaviviridae virus infection

1973

1973-02-06
GB
GB585873A
patent/GB1414841A/en
not_active
Expired

1973-02-06
GB
GB5099374A
patent/GB1414842A/en
not_active
Expired

1973-02-07
DE
DE19732305894
patent/DE2305894A1/en
active
Pending

1973-02-09
ES
ES411472A
patent/ES411472A1/en
not_active
Expired

1973-02-09
JP
JP1635273A
patent/JPS4891053A/ja
active
Pending

1973-02-09
FR
FR7304783A
patent/FR2181721B1/fr
not_active
Expired

Also Published As

Publication number
Publication date

ES411472A1
(en)

1976-03-16

GB1414842A
(en)

1975-11-19

FR2181721A1
(en)

1973-12-07

DE2305894A1
(en)

1973-09-06

FR2181721B1
(en)

1977-07-01

JPS4891053A
(en)

1973-11-27

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Legal Events

Date
Code
Title
Description

1976-03-31
PS
Patent sealed

1977-09-01
PLNP
Patent lapsed through nonpayment of renewal fees

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