DD262802A5 - Verfahren zur herstellung einer pharmazeutischen formulierung - Google Patents
Verfahren zur herstellung einer pharmazeutischen formulierung Download PDFInfo
- Publication number
- DD262802A5 DD262802A5 DD86309343A DD30934386A DD262802A5 DD 262802 A5 DD262802 A5 DD 262802A5 DD 86309343 A DD86309343 A DD 86309343A DD 30934386 A DD30934386 A DD 30934386A DD 262802 A5 DD262802 A5 DD 262802A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- azido
- compound
- active ingredient
- pharmaceutically acceptable
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims abstract description 102
- 238000000034 method Methods 0.000 claims abstract description 61
- 230000008569 process Effects 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 139
- 229910052739 hydrogen Inorganic materials 0.000 claims description 102
- -1 hydroxy , Mercapto, amino Chemical group 0.000 claims description 53
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 102000014150 Interferons Human genes 0.000 claims description 17
- 108010050904 Interferons Proteins 0.000 claims description 17
- 229940079322 interferon Drugs 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229960004150 aciclovir Drugs 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical group O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 230000000925 erythroid effect Effects 0.000 claims description 6
- 229940104230 thymidine Drugs 0.000 claims description 6
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 238000000844 transformation Methods 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 75
- 238000009472 formulation Methods 0.000 abstract description 57
- 238000011282 treatment Methods 0.000 abstract description 26
- 208000030507 AIDS Diseases 0.000 abstract description 10
- 238000011321 prophylaxis Methods 0.000 abstract description 7
- 206010038997 Retroviral infections Diseases 0.000 abstract description 5
- 208000027096 gram-negative bacterial infections Diseases 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
- 229960002555 zidovudine Drugs 0.000 description 61
- 239000003921 oil Substances 0.000 description 53
- 235000019198 oils Nutrition 0.000 description 53
- 229910052757 nitrogen Inorganic materials 0.000 description 48
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 46
- 239000000047 product Substances 0.000 description 44
- 150000001412 amines Chemical class 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
- 241000700605 Viruses Species 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
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- 229910002027 silica gel Inorganic materials 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 35
- 210000004027 cell Anatomy 0.000 description 33
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- 238000004458 analytical method Methods 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 230000000694 effects Effects 0.000 description 28
- 239000002777 nucleoside Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 235000019359 magnesium stearate Nutrition 0.000 description 23
- 150000003833 nucleoside derivatives Chemical class 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000003112 inhibitor Substances 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- 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 20
- 238000002474 experimental method Methods 0.000 description 20
- 239000008101 lactose Substances 0.000 description 20
- 239000003826 tablet Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 230000001225 therapeutic effect Effects 0.000 description 14
- 239000008215 water for injection Substances 0.000 description 14
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 13
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 13
- 239000002775 capsule Substances 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
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- 239000004615 ingredient Substances 0.000 description 13
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 13
- 229940069328 povidone Drugs 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 12
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- 238000010828 elution Methods 0.000 description 11
- 230000023611 glucuronidation Effects 0.000 description 11
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- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 10
- 239000003242 anti bacterial agent Substances 0.000 description 10
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- 229920003109 sodium starch glycolate Polymers 0.000 description 10
- 239000008109 sodium starch glycolate Substances 0.000 description 10
- 229940079832 sodium starch glycolate Drugs 0.000 description 10
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
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- 239000000463 material Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229940124597 therapeutic agent Drugs 0.000 description 9
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 9
- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 8
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 8
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- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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- ZSNNBSPEFVIUDS-SHYZEUOFSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 ZSNNBSPEFVIUDS-SHYZEUOFSA-N 0.000 description 4
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
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- MXKOAPUYOVRCDD-UYVBYVPASA-N diazonio-[(2s,3s,5r)-2-[hydroxy(methylsulfonyl)methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]azanide Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](C(O)S(C)(=O)=O)[C@@H]([N-][N+]#N)C1 MXKOAPUYOVRCDD-UYVBYVPASA-N 0.000 description 4
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
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- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 4
- 229940045145 uridine Drugs 0.000 description 4
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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- 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
- C07H19/06—Pyrimidine radicals
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- 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
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
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- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/776,899 US4724232A (en) | 1985-03-16 | 1985-09-17 | Treatment of human viral infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD262802A5 true DD262802A5 (de) | 1988-12-14 |
Family
ID=25108682
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86309343A DD262802A5 (de) | 1985-09-17 | 1986-09-15 | Verfahren zur herstellung einer pharmazeutischen formulierung |
| DD86294404A DD251984A5 (de) | 1985-09-17 | 1986-09-15 | Verfahren zur herstellung von 3'-azidonucleosiden und pharmazeutisch vertraeglichen derivaten davon |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86294404A DD251984A5 (de) | 1985-09-17 | 1986-09-15 | Verfahren zur herstellung von 3'-azidonucleosiden und pharmazeutisch vertraeglichen derivaten davon |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2523527B2 (ja) |
| DD (2) | DD262802A5 (ja) |
| ZA (1) | ZA867013B (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4916122A (en) * | 1987-01-28 | 1990-04-10 | University Of Georgia Research Foundation, Inc. | 3'-Azido-2',3'-dideoxyuridine anti-retroviral composition |
| DE3739366A1 (de) * | 1987-04-10 | 1988-10-27 | Boehringer Mannheim Gmbh | Desaza-purin-nucleosid-derivate, verfahren zu deren herstellung sowie deren verwendung bei der nucleinsaeure-sequenzierung sowie als antivirale mittel |
| GB8800276D0 (en) * | 1988-01-07 | 1988-02-10 | Univ Liverpool | Medical treatment |
| JPH02255696A (ja) * | 1989-03-28 | 1990-10-16 | Sanyo Kokusaku Pulp Co Ltd | 3’―アジド―2’、3’―ジデオキシ―4―チオピリミジンヌクレオシド誘導体、その製法およびそれを用いた抗ウイルス剤 |
| WO1997006179A1 (en) * | 1995-08-04 | 1997-02-20 | Kobayashi Perfumery Co., Ltd. | Process for producing azido nucleoside derivatives |
| EA200800932A1 (ru) | 2005-09-26 | 2008-10-30 | Фармассет, Инк. | Модифицированные 4`-нуклеозиды в качестве противовирусных агентов |
| DE102006037786A1 (de) * | 2006-08-11 | 2008-03-20 | Resprotect Gmbh | Nukleoside, diese enthaltendes Arzneimittel und deren Verwendung |
-
1986
- 1986-09-15 DD DD86309343A patent/DD262802A5/de not_active IP Right Cessation
- 1986-09-15 DD DD86294404A patent/DD251984A5/de not_active IP Right Cessation
- 1986-09-15 ZA ZA867013A patent/ZA867013B/xx unknown
- 1986-09-16 JP JP61217871A patent/JP2523527B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2523527B2 (ja) | 1996-08-14 |
| DD251984A5 (de) | 1987-12-02 |
| JPS62103100A (ja) | 1987-05-13 |
| ZA867013B (en) | 1988-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |