FR2464072A1 - Medicament antiviral renfermant de la (b-d-arabinofurannosyl)-1 thymine - Google Patents
Medicament antiviral renfermant de la (b-d-arabinofurannosyl)-1 thymine Download PDFInfo
- Publication number
- FR2464072A1 FR2464072A1 FR8018998A FR8018998A FR2464072A1 FR 2464072 A1 FR2464072 A1 FR 2464072A1 FR 8018998 A FR8018998 A FR 8018998A FR 8018998 A FR8018998 A FR 8018998A FR 2464072 A1 FR2464072 A1 FR 2464072A1
- Authority
- FR
- France
- Prior art keywords
- administration
- ara
- thymine
- antiviral drug
- treatment
- Prior art date
- 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.)
- Granted
Links
- 239000003443 antiviral agent Substances 0.000 title claims abstract description 14
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229940113082 thymine Drugs 0.000 title claims description 6
- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 10
- 208000015181 infectious disease Diseases 0.000 claims abstract description 8
- 239000013543 active substance Substances 0.000 claims abstract description 4
- 238000011282 treatment Methods 0.000 claims description 17
- 241001465754 Metazoa Species 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 241000450599 DNA viruses Species 0.000 claims description 2
- 229940124977 antiviral medication Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 241000700605 Viruses Species 0.000 abstract description 4
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract description 3
- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 2
- 239000002671 adjuvant Substances 0.000 abstract 1
- 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 description 21
- DWRXFEITVBNRMK-JAGXHNFQSA-N Spongothymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 DWRXFEITVBNRMK-JAGXHNFQSA-N 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 16
- 238000007912 intraperitoneal administration Methods 0.000 description 10
- 230000004083 survival effect Effects 0.000 description 8
- 238000009472 formulation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000700584 Simplexvirus Species 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 208000037952 HSV-1 infection Diseases 0.000 description 3
- 231100000111 LD50 Toxicity 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 241001529453 unidentified herpesvirus Species 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- 241000701081 Equid alphaherpesvirus 1 Species 0.000 description 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound 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 2
- 239000000654 additive Substances 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 238000000729 Fisher's exact test Methods 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11299079A JPS5639019A (en) | 1979-09-05 | 1979-09-05 | Antiviral agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2464072A1 true FR2464072A1 (fr) | 1981-03-06 |
| FR2464072B1 FR2464072B1 (enExample) | 1983-09-30 |
Family
ID=14600652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018998A Granted FR2464072A1 (fr) | 1979-09-05 | 1980-09-03 | Medicament antiviral renfermant de la (b-d-arabinofurannosyl)-1 thymine |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4344937A (enExample) |
| JP (1) | JPS5639019A (enExample) |
| FR (1) | FR2464072A1 (enExample) |
| GB (1) | GB2057879B (enExample) |
| IT (1) | IT1128169B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58225097A (ja) * | 1982-06-23 | 1983-12-27 | Yamasa Shoyu Co Ltd | ヌクレオシド５′−アルキルもしくはアルケニルりん酸 |
| JPS61133954U (enExample) * | 1985-02-12 | 1986-08-21 | ||
| SE8605503D0 (sv) * | 1986-12-19 | 1986-12-19 | Astra Laekemedel Ab | Novel medicinal use |
| US5215971A (en) * | 1986-12-19 | 1993-06-01 | Medivir Ab | Antiviral pharmaceutical composition comprising 5-substituted pyrimidine nucleosides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5455580A (en) * | 1977-09-10 | 1979-05-02 | Minerou Saneyoshi | Synthesis of 11*betaadd arabinofuracil**55 alkyluracils |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998807A (en) * | 1972-03-03 | 1976-12-21 | Syntex (U.S.A.) Inc. | Arabinofuranosyl cytosines and methods of making |
| US4096324A (en) * | 1975-07-07 | 1978-06-20 | The Upjohn Company | Cytidine nucleoside compound |
| US4230698A (en) * | 1978-05-12 | 1980-10-28 | Research Corporation | 2-Substituted arabinofuranosyl nucleosides and nucleotides |
-
1979
- 1979-09-05 JP JP11299079A patent/JPS5639019A/ja active Pending
-
1980
- 1980-08-19 GB GB8027035A patent/GB2057879B/en not_active Expired
- 1980-08-28 US US06/182,001 patent/US4344937A/en not_active Expired - Lifetime
- 1980-09-03 IT IT49601/80A patent/IT1128169B/it active
- 1980-09-03 FR FR8018998A patent/FR2464072A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5455580A (en) * | 1977-09-10 | 1979-05-02 | Minerou Saneyoshi | Synthesis of 11*betaadd arabinofuracil**55 alkyluracils |
Non-Patent Citations (1)
| Title |
|---|
| CA1980 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2057879A (en) | 1981-04-08 |
| FR2464072B1 (enExample) | 1983-09-30 |
| US4344937A (en) | 1982-08-17 |
| IT8049601A0 (it) | 1980-09-03 |
| IT1128169B (it) | 1986-05-28 |
| JPS5639019A (en) | 1981-04-14 |
| GB2057879B (en) | 1984-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |