CS274461B2 - Method of 6-substituted 2,3-dideoxynucleosides production - Google Patents

Method of 6-substituted 2,3-dideoxynucleosides production Download PDF

Info

Publication number: CS274461B2
Authority: CS; Czechoslovakia
Prior art keywords: carbon atoms; group; dideoxyribofuranoside; hydrogen; amino
Prior art date: 1987-04-09

Application number

CS242188A

Other languages

Czech (cs)

English (en)

Other versions

CS242188A2 (en

Inventor

George W Koszalka

Thomas A Krenitsky

Janet L Rideout

Charlene L Burns

Original Assignee

Wellcome Found

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.)

1987-04-09

Filing date

1988-04-08

Publication date

1991-04-11

1987-04-09 Priority claimed from GB878708512A external-priority patent/GB8708512D0/en

1987-05-29 Priority claimed from GB878712691A external-priority patent/GB8712691D0/en

1987-09-30 Priority claimed from GB878723013A external-priority patent/GB8723013D0/en

1988-04-08 Application filed by Wellcome Found filed Critical Wellcome Found

1990-09-12 Publication of CS242188A2 publication Critical patent/CS242188A2/cs

1991-04-11 Publication of CS274461B2 publication Critical patent/CS274461B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 35
238000004519 manufacturing process Methods 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 40
239000002777 nucleoside Substances 0.000 claims abstract description 6
-1 alkyl radical Chemical class 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
150000003833 nucleoside derivatives Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
102000004190 Enzymes Human genes 0.000 claims description 3
108090000790 Enzymes Proteins 0.000 claims description 3
125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
125000001805 pentosyl group Chemical group 0.000 claims description 3
238000012546 transfer Methods 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000012467 final product Substances 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 7
125000005843 halogen group Chemical group 0.000 claims 4
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000005110 aryl thio group Chemical group 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
244000145841 kine Species 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 15
238000011321 prophylaxis Methods 0.000 abstract description 7
208000031886 HIV Infections Diseases 0.000 abstract description 6
239000008194 pharmaceutical composition Substances 0.000 abstract description 6
125000003835 nucleoside group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 174
239000000047 product Substances 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
229910001868 water Inorganic materials 0.000 description 50
239000000203 mixture Substances 0.000 description 47
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
239000004480 active ingredient Substances 0.000 description 44
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229920005989 resin Polymers 0.000 description 41
239000011347 resin Substances 0.000 description 41
238000004458 analytical method Methods 0.000 description 39
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239000000741 silica gel Substances 0.000 description 33
229910002027 silica gel Inorganic materials 0.000 description 33
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239000002904 solvent Substances 0.000 description 30
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 27
239000003826 tablet Substances 0.000 description 25
239000000126 substance Substances 0.000 description 24
101710132082 Pyrimidine/purine nucleoside phosphorylase Proteins 0.000 description 23
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
239000000706 filtrate Substances 0.000 description 21
238000004108 freeze drying Methods 0.000 description 21
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
239000000725 suspension Substances 0.000 description 20
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101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 description 17
102000030764 Purine-nucleoside phosphorylase Human genes 0.000 description 17
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 17
XKKCQTLDIPIRQD-JGVFFNPUSA-N 1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical class O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)CC1 XKKCQTLDIPIRQD-JGVFFNPUSA-N 0.000 description 16
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
230000000269 nucleophilic effect Effects 0.000 description 15
229910000160 potassium phosphate Inorganic materials 0.000 description 15
235000011009 potassium phosphates Nutrition 0.000 description 15
ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 13
239000002775 capsule Substances 0.000 description 13
239000004615 ingredient Substances 0.000 description 13
239000007795 chemical reaction product Substances 0.000 description 11
239000008057 potassium phosphate buffer Substances 0.000 description 10
208000030507 AIDS Diseases 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
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241000725303 Human immunodeficiency virus Species 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
239000000872 buffer Substances 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
239000008101 lactose Substances 0.000 description 8
235000019359 magnesium stearate Nutrition 0.000 description 8
229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
239000001267 polyvinylpyrrolidone Substances 0.000 description 8
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 6
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
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239000007903 gelatin capsule Substances 0.000 description 4
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239000002212 purine nucleoside Substances 0.000 description 4
229920003109 sodium starch glycolate Polymers 0.000 description 4
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
210000001744 T-lymphocyte Anatomy 0.000 description 3
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239000000969 carrier Substances 0.000 description 3
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PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 3
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CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 description 2
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
HBYORZQNJPQOQI-UHFFFAOYSA-N 5-[[3-[(3,4-dichlorophenyl)methylsulfanyl]thiophene-2-carbonyl]sulfamoyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1S(=O)(=O)NC(=O)C1=C(SCC=2C=C(Cl)C(Cl)=CC=2)C=CS1 HBYORZQNJPQOQI-UHFFFAOYSA-N 0.000 description 2
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UAPKUSSHIIMXGE-UHFFFAOYSA-N 6-cyclohexyloxy-7h-purine Chemical compound C1CCCCC1OC1=NC=NC2=C1NC=N2 UAPKUSSHIIMXGE-UHFFFAOYSA-N 0.000 description 2
MEOMXKNIFWDDGZ-UHFFFAOYSA-N 6-morpholin-4-yl-9h-purine Chemical compound C1COCCN1C1=NC=NC2=C1N=CN2 MEOMXKNIFWDDGZ-UHFFFAOYSA-N 0.000 description 2
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STYFLCAHEVROJU-UHFFFAOYSA-N n,n-diethyl-7h-purin-6-amine Chemical compound CCN(CC)C1=NC=NC2=C1NC=N2 STYFLCAHEVROJU-UHFFFAOYSA-N 0.000 description 2
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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150000003871 sulfonates Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000008719 thickening Effects 0.000 description 1
YFTWHEBLORWGNI-UHFFFAOYSA-N tiamiprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC(N)=NC2=C1NC=N2 YFTWHEBLORWGNI-UHFFFAOYSA-N 0.000 description 1
229950011457 tiamiprine Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000005389 trialkylsiloxy group Chemical group 0.000 description 1
125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229960000523 zalcitabine Drugs 0.000 description 1

Classifications

- 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
- C07H19/16—Purine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Virology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Immunology (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Tropical Medicine & Parasitology (AREA)
AIDS & HIV (AREA)
Bioinformatics & Cheminformatics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CS242188A 1987-04-09 1988-04-08 Method of 6-substituted 2,3-dideoxynucleosides production CS274461B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB878708512A GB8708512D0 (en)	1987-04-09	1987-04-09	Therapeutic nucleosides
GB878712691A GB8712691D0 (en)	1987-05-29	1987-05-29	Therapeutic nucleosides
GB878723013A GB8723013D0 (en)	1987-09-30	1987-09-30	Therapeutic nucleosides

Publications (2)

Publication Number	Publication Date
CS242188A2 CS242188A2 (en)	1990-09-12
CS274461B2 true CS274461B2 (en)	1991-04-11

Family

ID=27263377

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS242188A CS274461B2 (en)	1987-04-09	1988-04-08	Method of 6-substituted 2,3-dideoxynucleosides production

Country Status (20)

Country	Link
US (1)	US5068320A (pt)
EP (1)	EP0286425B1 (pt)
JP (1)	JP2763888B2 (pt)
KR (1)	KR880012630A (pt)
AP (1)	AP78A (pt)
AT (1)	ATE116984T1 (pt)
AU (1)	AU608590B2 (pt)
CA (1)	CA1326237C (pt)
CS (1)	CS274461B2 (pt)
DE (1)	DE3852710T2 (pt)
DK (1)	DK191688A (pt)
FI (1)	FI87214C (pt)
HU (1)	HU201954B (pt)
IL (1)	IL86007A0 (pt)
MC (1)	MC1915A1 (pt)
NO (1)	NO171641C (pt)
NZ (1)	NZ224189A (pt)
PL (1)	PL154956B1 (pt)
PT (1)	PT87191B (pt)
RU (1)	RU1779256C (pt)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL86007A0 (en) *	1987-04-09	1988-09-30	Wellcome Found	6-substituted purine nucleosides,their preparation and pharmaceutical compositions containing them
US5185437A (en) *	1987-04-09	1993-02-09	Burroughs Wellcome Co.	Therapeutic nucleosides
US5077280A (en) *	1988-04-12	1991-12-31	Brown University Research Foundation	Treatment of viral infections
IE882585L (en) *	1988-08-25	1990-02-25	Prendergast Patrick T	Viral treatment system
DE68907013D1 (de) *	1988-10-24	1993-07-15	Wellcome Found	Guaninderivate mit antiviraler wirkung und deren pharmazeutisch vertraegliche salze.
AU4817490A (en) *	1988-11-29	1990-06-26	Institut Fur Molekularbiologie Und Analytik (Ima) G.M.B.H.	2',3'-dideoxyribofuranosides and process for producing them
JP2619710B2 (ja) *	1989-02-27	1997-06-11	日本製紙株式会社	２′，３′−ジデオキシプリンヌクレオシド類の製造方法
US5585364A (en) *	1989-04-13	1996-12-17	British Technology Group Limited	Antiviral compounds
US5013829A (en) *	1989-04-26	1991-05-07	University Of Iowa Research Foundation	Stable congener of 2',3'-dideoxyadenosine
DE4020529A1 (de) *	1989-09-12	1991-03-21	Roxana Vasiloiu	Multifunktionelle(s) enzym(e) mit nucleosid-didesoxyribosyltransferase(n) und/oder nucleoside-desoxyribosyltransferasen(n) und/oder kinease- und/oder reduktase- und/oder desaminase- und/oder polymerase-aktivitaet
JPH0637391B2 (ja) *	1989-09-29	1994-05-18	日本製紙株式会社	抗エイズウイルス剤
PT95516A (pt) *	1989-10-06	1991-08-14	Wellcome Found	Processo para a preparacao de derivados de 2',3'-didesoxi nucleosidos 6-substituidos
CA2075490A1 (en) *	1990-02-09	1991-08-10	Hiroaki Mitsuya	6-halo-and 2-amino-6-halo-purine 2',3'-dideoxy nucleosides and their use as antiviral agents
US5654286A (en) *	1993-05-12	1997-08-05	Hostetler; Karl Y.	Nucleotides for topical treatment of psoriasis, and methods for using same
MXPA01006425A (es) *	1998-12-23	2002-06-04	Iaf Biochem Int	Analogos de nucleosido antivirales.
CN101220071B (zh) *	2008-01-17	2011-04-06	南京长澳医药科技有限公司	稳定的6-甲氧基-2’,3’-双脱氧鸟嘌呤核苷及其制备方法和包含它的药物组合物
CN102234280B (zh) *	2010-04-26	2014-01-08	北京大学	D,l-鸟嘌呤核苷类似物及其制备方法和应用
NZ607996A (en)	2010-09-22	2014-07-25	Alios Biopharma Inc	Substituted nucleotide analogs
WO2012167053A1 (en)	2011-06-01	2012-12-06	Janus Biotherapeutics, Inc.	Novel immune system modulators
CA2860234A1 (en)	2011-12-22	2013-06-27	Alios Biopharma, Inc.	Substituted phosphorothioate nucleotide analogs
HK1206362A1 (zh)	2012-03-21	2016-01-08	Alios Biopharma, Inc.	硫代氨基磷酸酯核苷酸前藥的固體形式
WO2013142157A1 (en)	2012-03-22	2013-09-26	Alios Biopharma, Inc.	Pharmaceutical combinations comprising a thionucleotide analog
CN105073750A (zh) *	2013-03-05	2015-11-18	豪夫迈·罗氏有限公司	布鲁顿氏酪氨酸激酶抑制剂

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1573777A (en) *	1977-11-03	1980-08-28	Wellcome Found	9-d-arabinonucleosides and an enzymatic process for their preparation
US4724232A (en) *	1985-03-16	1988-02-09	Burroughs Wellcome Co.	Treatment of human viral infections
ATE113603T1 (de) *	1985-03-16	1994-11-15	Wellcome Found	Antivirale nukleoside.
ES8801303A1 (es) *	1985-05-15	1987-12-16	Wellcome Found	Un procedimiento para preparar una formulacion farmaceutica que contiene un 2'3'-didesoxi-nucleosido.
WO1987001283A1 (en) *	1985-08-26	1987-03-12	United States Of America, Represented By The Unite	Inhibition of in vitro infectivity and cytopathic effect of htlv-iii/lav by 2',3'-dideoxycytidine
DE3650741T2 (de) *	1985-09-17	2000-10-12	The Wellcome Foundation Ltd., Greenford	Kombination therapeutische Nukleoside mit weiteren therapeutisch wirksamen Komponenten.
IT1203558B (it) *	1986-05-20	1989-02-15	Firestone Int Dev Spa	Metodo per la realizzazione di un pneumatico radiale di prima fase per veicoli
AU613026B2 (en) *	1987-03-24	1991-07-25	Nycomed As	2',3' dideoxyribofuranoxide derivatives
IL86007A0 (en) *	1987-04-09	1988-09-30	Wellcome Found	6-substituted purine nucleosides,their preparation and pharmaceutical compositions containing them
NZ225447A (en) *	1987-07-20	1991-12-23	Merck & Co Inc	Piperazinyl derivatives of purine and purine isosteres and pharmaceutical compositions

1988
- 1988-04-07 IL IL86007A patent/IL86007A0/xx unknown
- 1988-04-08 NO NO881537A patent/NO171641C/no unknown
- 1988-04-08 PL PL1988271722A patent/PL154956B1/pl unknown
- 1988-04-08 EP EP88303158A patent/EP0286425B1/en not_active Expired - Lifetime
- 1988-04-08 NZ NZ224189A patent/NZ224189A/xx unknown
- 1988-04-08 JP JP63087034A patent/JP2763888B2/ja not_active Expired - Lifetime
- 1988-04-08 AU AU14444/88A patent/AU608590B2/en not_active Ceased
- 1988-04-08 CA CA000563634A patent/CA1326237C/en not_active Expired - Fee Related
- 1988-04-08 AT AT88303158T patent/ATE116984T1/de not_active IP Right Cessation
- 1988-04-08 KR KR1019880003964A patent/KR880012630A/ko not_active Ceased
- 1988-04-08 RU SU884355537A patent/RU1779256C/ru active
- 1988-04-08 DK DK191688A patent/DK191688A/da not_active Application Discontinuation
- 1988-04-08 FI FI881651A patent/FI87214C/fi not_active IP Right Cessation
- 1988-04-08 DE DE3852710T patent/DE3852710T2/de not_active Expired - Fee Related
- 1988-04-08 CS CS242188A patent/CS274461B2/cs unknown
- 1988-04-08 HU HU881784A patent/HU201954B/hu not_active IP Right Cessation
- 1988-04-08 AP APAP/P/1988/000086A patent/AP78A/en active
- 1988-04-08 MC MC881970A patent/MC1915A1/fr unknown
- 1988-04-08 PT PT87191A patent/PT87191B/pt active IP Right Grant
1989
- 1989-10-06 US US07/417,989 patent/US5068320A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO881537L (no)	1988-10-10
HUT48269A (en)	1989-05-29
DK191688A (da)	1988-10-10
JPS63267796A (ja)	1988-11-04
JP2763888B2 (ja)	1998-06-11
IL86007A0 (en)	1988-09-30
FI87214B (fi)	1992-08-31
FI87214C (fi)	1992-12-10
AU1444488A (en)	1988-10-13
AP78A (en)	1990-03-12
NO171641B (no)	1993-01-04
HU201954B (en)	1991-01-28
PT87191B (pt)	1993-02-26
DK191688D0 (da)	1988-04-08
MC1915A1 (fr)	1989-04-06
KR880012630A (ko)	1988-11-28
DE3852710D1 (de)	1995-02-23
DE3852710T2 (de)	1995-05-24
ATE116984T1 (de)	1995-01-15
NZ224189A (en)	1991-09-25
CA1326237C (en)	1994-01-18
AU608590B2 (en)	1991-04-11
PL271722A1 (en)	1989-01-23
EP0286425A3 (en)	1990-12-05
RU1779256C (ru)	1992-11-30
PL154956B1 (en)	1991-10-31
EP0286425B1 (en)	1995-01-11
CS242188A2 (en)	1990-09-12
FI881651L (fi)	1988-10-10
US5068320A (en)	1991-11-26
NO881537D0 (no)	1988-04-08
PT87191A (pt)	1988-05-01
FI881651A0 (fi)	1988-04-08
NO171641C (no)	1993-04-14
AP8800086A0 (en)	1988-02-01
EP0286425A2 (en)	1988-10-12

Publication	Publication Date	Title
CS274461B2 (en)	1991-04-11	Method of 6-substituted 2,3-dideoxynucleosides production
FI87783C (fi)	1993-02-25	Foerfarande foer framstaellning av terapeutiskt anvaendbara 2',3'-dideoxinukleosider
DE60026861T2 (de)	2006-09-21	Purin-derivate
DK167377B1 (da)	1993-10-25	3'-azidopyrimidinnucleosider eller farmaceutisk acceptable salte eller estere deraf til anvendelse ved behandling af eller profylakse for en human retrovirusinfektion
FI106461B (fi)	2001-02-15	Menetelmä terapeuttisesti käyttökelpoisten enantiomeeristen yhdisteiden valmistamiseksi sekä menetelmässä käyttökelpoinen välituote
US5185437A (en)	1993-02-09	Therapeutic nucleosides
SK18192001A3 (sk)	2003-04-01	Deriváty purínu
CZ20021223A3 (cs)	2003-05-14	Purinové deriváty
CZ283185B6 (cs)	1998-01-14	Protivirově účinná kombinace nukleosidů
EP0285432B1 (en)	1992-11-11	Therapeutic nucleosides
AU637831B2 (en)	1993-06-10	Therapeutic necleosides
AU616914B2 (en)	1991-11-14	Therapeutic necleosides
AP73A (en)	1990-03-01	Therapeautic nucleosides.
EP4399215A1 (en)	2024-07-17	Improved methods for production of cyclic guanosine-monophosphate analogues
JPH07502741A (ja)	1995-03-23	治療用ヌクレオシド
US5175274A (en)	1992-12-29	Therapeutic nucleosides
WO2024120467A1 (en)	2024-06-13	Phosphoramidate monosaccharides, pharmaceutical compositions, and diagnostic and therapeutic applications
JPH06500543A (ja)	1994-01-20	ヌクレオシドの新規なリン脂質誘導体、それらの製造法、並びに抗ウイルス性医薬としてのそれらの使用