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US4097665A
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Diacylnucleosides and process for preparing the same
Assignee: Asahi Kasei Corp
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Filing: 1975-11-24
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Granted: 1978-06-27
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Expires: 1995-11-24
Abstract
Abstract Compounds represented by formula (I) ##STR1## wherein one of Z 1 ', Z 2 ', Z 3 ' and Z 4 ' represents R, another one of Z 1 ', Z 2 ', Z 3 ' and Z 4 ' represents Z, and the remaining two moieties of Z 1 ', Z 2 ', Z 3 ' and Z 4 ' represents a hydrogen atom and/or a protective group, one of R and Z represents A 1 and the other represents A 2 , A 1 being an acyl group having 14 to 22 carbon atoms which does not contain a carboxylic group and A 2 being an acyl group having 2 to 14 carbon atoms and having one carboxyl group, X represents a hydrogen atom or a halogen atom (hereinafter referred to as Compound Ia); a 2,2'-anhydro product of Compound Ia wherein Z 2 ' represents a hydrogen atom (hereinafter referred to as Compound Ib); an arabinosylation product of Compound Ia (hereinafter referred to as Compound Ic); a deamination product of Compound Ia (hereinafter referred to as Compound Id); a 2'-deoxy product of Compound Id wherein Z 2 ' represents a hydrogen atom (hereinafter referred to as Compound Ie); a salt of Compound Ia, Ib, Ic, or Id or Ie having an A 2 group with a base (hereinafter referred to as Compound If); and a salt of Compound Ia, Ib or Ic wherein Z 1 ' represents a hydrogen atom with an acid (hereinafter referred to as Compound Ih); and processes for preparing the same.
Inventors
- 👤 Torao Ishida
- 👤 Minoru Akiyama
- 👤 Daikichi Nishimura
- 👤 Hiroshi Hayashi
- 👤 Yoshio Sakurai
- 👤 Shigeru Tsukagoshi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 23:21
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; A; A61; A61P; A61P35/00; A61P35/02; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
204 words
A compound selected from the group consisting of compounds represented by the general formulae ##STR6## wherein (a) B represents OZ 2 ' or hydrogen; (b) one of Z 1 ', Z 2 ', Z 3 ' and Z 4 ' represents A 1 and another represents A 2 and the remainder represents hydrogen or a protective group wherein A 1 is C 14 -C 22 aliphatic acyl selected from the group consisting of myristoyl, palmitoyl, margaroyl, stearoyl, n-nonadecanoyl, arachidoyl, n-heneicosanoyl, behenoyl, oleoyl, arachidonoyl, or the aliphatic acyl substituted with fluoro, chloro, bromo, iodo, hydroxy, mercapto, phenyl, phenoxy, thiophenoxy, nitrophenyl, cyclohexyl, 2-thienyl, 2-tetrahydropyranyloxy, methoxy, thiomethoxy, carboxymethyl, epoxy and oxo; A 2 is C 2 -C 14 having carboxy or the acyl substituted with a group selected from the group consisting of phenyl, hydroxy, fluoro, chloro, bromo, iodo, N-carbobenzyloxyamino, cyclohexyl, mercapto, nitro, furane, pyridine, oxo, adamantane, oxymethenylcarboxy and thiomethenylcarboxy; and the protective group is selected from the group consisting of isopropylidene, ethylidene, benzylidene, tetrahydropyranyl, tetrahydrofuranyl, ethoxyethyl, methoxymethyl, ethoxymethyl, methoxyethyl, triphenylmethyl, 2,4-dinitroanilino, methoxycarbonyl, trichloroethoxycarbonyl, tribromoethoxycarbonyl, formyl, trifluoroacetyl, trichloroacetyl, benzyl, benzhydrine, 2,4-dinitrophenylsulphenyl, propenyl, borate, vinylthioether and benzoylpropyl; and (c) X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine and iodine; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
204 words
A compound selected from the group consisting of compounds represented by the general formulae ##STR6## wherein (a) B represents OZ 2 ' or hydrogen; (b) one of Z 1 ', Z 2 ', Z 3 ' and Z 4 ' represents A 1 and another represents A 2 and the remainder represents hydrogen or a protective group wherein A 1 is C 14 -C 22 aliphatic acyl selected from the group consisting of myristoyl, palmitoyl, margaroyl, stearoyl, n-nonadecanoyl, arachidoyl, n-heneicosanoyl, behenoyl, oleoyl, arachidonoyl, or the aliphatic acyl substituted with fluoro, chloro, bromo, iodo, hydroxy, mercapto, phenyl, phenoxy, thiophenoxy, nitrophenyl, cyclohexyl, 2-thienyl, 2-tetrahydropyranyloxy, methoxy, thiomethoxy, carboxymethyl, epoxy and oxo; A 2 is C 2 -C 14 having carboxy or the acyl substituted with a group selected from the group consisting of phenyl, hydroxy, fluoro, chloro, bromo, iodo, N-carbobenzyloxyamino, cyclohexyl, mercapto, nitro, furane, pyridine, oxo, adamantane, oxymethenylcarboxy and thiomethenylcarboxy; and the protective group is selected from the group consisting of isopropylidene, ethylidene, benzylidene, tetrahydropyranyl, tetrahydrofuranyl, ethoxyethyl, methoxymethyl, ethoxymethyl, methoxyethyl, triphenylmethyl, 2,4-dinitroanilino, methoxycarbonyl, trichloroethoxycarbonyl, tribromoethoxycarbonyl, formyl, trifluoroacetyl, trichloroacetyl, benzyl, benzhydrine, 2,4-dinitrophenylsulphenyl, propenyl, borate, vinylthioether and benzoylpropyl; and (c) X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine and iodine; and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
27 words
A compound according to claim 1, wherein said compound is selected from the group consisting of compounds represented by formula (1), (2) and pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
26 words
A compound according to claim 1, wherein said compound is selected from the group consisting of compounds represented by formula (2) and pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
48 words
A compound according to claim 1 wherein said compound is selected from the group consisting of compounds represented by formula (2) and pharmaceutically acceptable salts thereof, and wherein Z 1 ' is A 1 , Z 4 ' is A 2 , and Z 3 ' is hydrogen.
Claim 6
Dependent Claim
50 words
A compound according to claim 1, wherein the pharmaceutically acceptable salt is selected from the group consisting of a sodium salt, a potassium salt, a calcium salt, an ammonium salt, a trimethylamine salt, a triethylamine salt, a procaine salt, a dibenzylamine salt, N-benzyl-β-phenylamine salt, N,N'-dibenzylethylenediamine salt and a chloline salt.
Claim 7
Dependent Claim
79 words
A compound according to claim 5, wherein (a) A 1 is selected from the group consisting of myristoyl, palmitoyl, margaroyl, stearoyl, n-nonadecanoyl, arachidoyl, n-heneicosanoyl, behenoyl, oleoyl, arachidonoyl, 2-chlorostearoyl, 18-hydroxystearoyl, 2-mercaptostearoyl, phenylauroyl, phenoxylauroyl, p-nitrophenyllauroyl, thiophenoxylauroyl, cyclohexyllauroyl, 14-(2-thienyl)myristoyl, 14-(2-tetrahydropyranyloxy)myristoyl, 18-methoxystearoyl, 18-thiomethoxystearoyl, 16-carboxymethylpalmitoyl, 12,13-epoxy-9-octadecanoyl and 4-oxostearoyl; and (b) A 2 is selected from the group consisting of hemifumaroyl, 4-carboxymethylphenylacetyl, hemitartroyl, hemiterephthaloyl, hemisuccinyl, hemicitraconoyl, hemihomophthaloyl, hemibromosuccinyl, hemi-N-carbobenzyloxy-L-aspartyl, 1'-carboxymethylcyclohexylacetyl, hemidiglycoloyl, hemihydroxytartroyl, hemiitaconyl, hemiglutaryl, hemimercaptosuccinyl, hemimucoyl, heminitrosuccinyl, 1-carboxycyclobutanecarbonyl, 4-carboxyfurane-3-carbonyl, 5-carboxypyridine-2-carbonyl, 3-carboxyacetonecarbonyl, 3-carboxymethyladamataneacetyl, hemichloromaleoyl and hemidithioglycoloyl.
Claim 8
Dependent Claim
47 words
A compound according to claim 1 wherein (a) A 1 is selected from the group consisting of myristoyl, palmitoyl, margaroyl, stearoyl, n-nonadecanoyl, arachidoyl, n-heneicosanoyl and behenoyl; (b) A 2 is hemisuccinyl; (c) X is hydrogen of fluorine; and (d) the pharmaceutically acceptable salt is a sodium salt.
Claim 9
Dependent Claim
41 words
A compound according to claim 1, wherein (a) A 1 is selected from the group consisting of myristoyl, palmitoyl, margaroyl, stearoyl, n-nonadecanoyl, arachidoyl, n-heneicosanoyl and behenoyl; (b) A 2 is hemisuccinyl; and (c) the pharmaceutically acceptable salt is a sodium salt.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |