NO881135L - Fremgangsmaate for fremstilling av 1-(3-azido-2,3-dideoksy-betad-erytro-pentofuranosyl)-5-metyl-2(1h)-pyrimidinon. - Google Patents
Fremgangsmaate for fremstilling av 1-(3-azido-2,3-dideoksy-betad-erytro-pentofuranosyl)-5-metyl-2(1h)-pyrimidinon.Info
- Publication number
- NO881135L NO881135L NO881135A NO881135A NO881135L NO 881135 L NO881135 L NO 881135L NO 881135 A NO881135 A NO 881135A NO 881135 A NO881135 A NO 881135A NO 881135 L NO881135 L NO 881135L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- azido
- preparation
- group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 22
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title claims 5
- 150000001875 compounds Chemical class 0.000 claims description 64
- 238000011282 treatment Methods 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 229910001923 silver oxide Inorganic materials 0.000 claims description 2
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 claims 4
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 238000000844 transformation Methods 0.000 claims 1
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- 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 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- -1 1-(3-azido-2 Chemical class 0.000 description 12
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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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- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- TZBAVQKIEKDGFH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-1-benzothiophene-2-carboxamide;hydrochloride Chemical compound [Cl-].C1=CC=C2SC(C(=O)NCC[NH+](CC)CC)=CC2=C1 TZBAVQKIEKDGFH-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005550 wet granulation Methods 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
- C07H19/06—Pyrimidine radicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878706176A GB8706176D0 (en) | 1987-03-16 | 1987-03-16 | Therapeutic nucleosides |
| US13880887A | 1987-12-28 | 1987-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO881135D0 NO881135D0 (no) | 1988-03-15 |
| NO881135L true NO881135L (no) | 1988-09-19 |
Family
ID=26292019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO881135A NO881135L (no) | 1987-03-16 | 1988-03-15 | Fremgangsmaate for fremstilling av 1-(3-azido-2,3-dideoksy-betad-erytro-pentofuranosyl)-5-metyl-2(1h)-pyrimidinon. |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0287215B1 (da) |
| JP (1) | JPS63290894A (da) |
| AP (1) | AP73A (da) |
| AU (1) | AU601556B2 (da) |
| CA (1) | CA1321387C (da) |
| DE (1) | DE3872028T2 (da) |
| DK (1) | DK140588A (da) |
| ES (1) | ES2039615T3 (da) |
| FI (1) | FI881216A (da) |
| GR (1) | GR3005506T3 (da) |
| HU (1) | HU199865B (da) |
| IL (1) | IL85738A0 (da) |
| MC (1) | MC1914A1 (da) |
| NO (1) | NO881135L (da) |
| NZ (1) | NZ223880A (da) |
| PH (1) | PH24812A (da) |
| PL (1) | PL271196A1 (da) |
| PT (1) | PT86982B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8706176D0 (en) * | 1987-03-16 | 1987-04-23 | Wellcome Found | Therapeutic nucleosides |
| US4804651A (en) * | 1987-06-09 | 1989-02-14 | Board Of Regents, The University Of Texas System | Methods and compositions for the treatment of psoriasis |
| US5077280A (en) * | 1988-04-12 | 1991-12-31 | Brown University Research Foundation | Treatment of viral infections |
| GB8902041D0 (en) * | 1989-01-31 | 1989-03-22 | Tanabe Seiyaku Co | Antiviral agent and novel nucleoside |
| US5220003A (en) * | 1991-03-29 | 1993-06-15 | The Regents Of The University Of California | Process for the synthesis of 2',3'-dideoxynucleosides |
| CA2103050A1 (en) * | 1991-05-15 | 1992-11-16 | Yung-Chi Cheng | Determination of prodrugs metabolizable by the liver and therapeutic use thereof |
| RU2111970C1 (ru) * | 1996-06-25 | 1998-05-27 | Иван Игоревич Федоров | 3'-оксимино-2',3'-дидезоксинуклеозиды |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4468384A (en) * | 1982-01-05 | 1984-08-28 | The Research Foundation Of State University Of New York | Method for the inhibition of the replication of DNA viruses with 5-substituted 2-pyrimidinone nucleosides |
| EP0199451B1 (en) * | 1985-03-16 | 1996-03-06 | The Wellcome Foundation Limited | Therapeutic nucleosides |
| PT82199B (pt) * | 1985-03-16 | 1990-11-07 | Wellcome Found | Processo para a preparacao de nucleosidos antivirais e de composicoes farmaceuticas que os contem |
| ATE190064T1 (de) * | 1985-09-17 | 2000-03-15 | Wellcome Found | Kombination therapeutische nukleoside mit weiteren therapeutisch wirksamen komponenten. |
-
1988
- 1988-03-15 HU HU881231A patent/HU199865B/hu unknown
- 1988-03-15 PL PL27119688A patent/PL271196A1/xx unknown
- 1988-03-15 DK DK140588A patent/DK140588A/da not_active Application Discontinuation
- 1988-03-15 FI FI881216A patent/FI881216A/fi not_active IP Right Cessation
- 1988-03-15 JP JP63061752A patent/JPS63290894A/ja active Pending
- 1988-03-15 NO NO881135A patent/NO881135L/no unknown
- 1988-03-15 IL IL85738A patent/IL85738A0/xx unknown
- 1988-03-15 PH PH36641A patent/PH24812A/en unknown
- 1988-03-15 PT PT86982A patent/PT86982B/pt not_active IP Right Cessation
- 1988-03-15 CA CA000561458A patent/CA1321387C/en not_active Expired - Fee Related
- 1988-03-15 ES ES198888302233T patent/ES2039615T3/es not_active Expired - Lifetime
- 1988-03-15 DE DE8888302233T patent/DE3872028T2/de not_active Expired - Fee Related
- 1988-03-15 AU AU13185/88A patent/AU601556B2/en not_active Ceased
- 1988-03-15 MC MC881958A patent/MC1914A1/xx unknown
- 1988-03-15 NZ NZ223880A patent/NZ223880A/xx unknown
- 1988-03-15 AP APAP/P/1988/000085A patent/AP73A/en active
- 1988-03-15 EP EP88302233A patent/EP0287215B1/en not_active Expired - Lifetime
-
1992
- 1992-08-25 GR GR920401850T patent/GR3005506T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3872028T2 (de) | 1993-01-14 |
| AU601556B2 (en) | 1990-09-13 |
| NZ223880A (en) | 1991-06-25 |
| NO881135D0 (no) | 1988-03-15 |
| EP0287215A2 (en) | 1988-10-19 |
| AU1318588A (en) | 1988-09-15 |
| FI881216A0 (fi) | 1988-03-15 |
| PH24812A (en) | 1990-10-30 |
| CA1321387C (en) | 1993-08-17 |
| GR3005506T3 (da) | 1993-06-07 |
| DE3872028D1 (en) | 1992-07-23 |
| PT86982B (pt) | 1992-06-30 |
| FI881216A (fi) | 1988-09-17 |
| DK140588D0 (da) | 1988-03-15 |
| AP8800085A0 (en) | 1988-02-01 |
| MC1914A1 (fr) | 1989-04-06 |
| IL85738A0 (en) | 1988-08-31 |
| EP0287215B1 (en) | 1992-06-17 |
| ES2039615T3 (es) | 1993-10-01 |
| HUT47591A (en) | 1989-03-28 |
| EP0287215A3 (en) | 1990-01-10 |
| DK140588A (da) | 1988-09-17 |
| JPS63290894A (ja) | 1988-11-28 |
| PT86982A (pt) | 1988-04-01 |
| AP73A (en) | 1990-03-01 |
| HU199865B (en) | 1990-03-28 |
| PL271196A1 (en) | 1988-12-08 |
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