SE8803309L - ANTIVIRAL AGENTS - Google Patents
ANTIVIRAL AGENTSInfo
- Publication number
- SE8803309L SE8803309L SE8803309A SE8803309A SE8803309L SE 8803309 L SE8803309 L SE 8803309L SE 8803309 A SE8803309 A SE 8803309A SE 8803309 A SE8803309 A SE 8803309A SE 8803309 L SE8803309 L SE 8803309L
- Authority
- SE
- Sweden
- Prior art keywords
- compounds
- formula
- phosphonate
- salts
- azidomethyl
- Prior art date
Links
- 239000003443 antiviral agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 purine nucleoside phosphonate derivatives Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 241000725303 Human immunodeficiency virus Species 0.000 abstract 2
- 230000000840 anti-viral effect Effects 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004970 halomethyl group Chemical group 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical class N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 abstract 1
- 229930024421 Adenine Natural products 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000700605 Viruses Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229960000643 adenine Drugs 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 239000002212 purine nucleoside Substances 0.000 abstract 1
- 150000003212 purines Chemical class 0.000 abstract 1
- 241001430294 unidentified retrovirus Species 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Certain open chain purine nucleoside phosphonate derivatives have antiviral activity against the Herpes group of viruses, and also show effective antiviral activity against retroviruses, including human immunodeficiency virus (HIV). These compounds have formula (1), wherein B represents a substituted or unsubstituted purine base, especially adenine or guanine and their halogenated derivatives, R1 is selected from H, methyl, hydroxymethyl, halomethyl, azidomethyl, and cyano; R2 is selected from H, methyl, hydroxymethyl, halomethyl, azidomethyl, cyano, and OH; also when R2 is OH the carbon to which it is attached may be oxidized so that the H there shown and R2 together may be =0; and n is an integer of 0-5. The compounds of the invention further include the pharmaceutically acceptable mono- and dibasic salts and the mono- and diesters of the phosphonate moiety and the acid addition salts of the murine-substituted purines. In addition, when R1 or R2 is -CH2OH, or when R2 is OH, the acyl (1-6C) esters of these alcohols are included in the invention. Further, when n is 0, 1, or 2 and R1 is CH2OH, the compounds of formula (1) include the cyclic forms wherein formal dehydration between R1 and one of the -OH groups on the phosphonate results in compounds of formula (1a) and their corresponding salts and esters.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US547187A | 1987-01-20 | 1987-01-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8803309L true SE8803309L (en) | 1988-09-19 |
| SE8803309D0 SE8803309D0 (en) | 1988-09-19 |
Family
ID=21716038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8803309A SE8803309D0 (en) | 1987-01-20 | 1988-09-19 | ANTIVIRAL AGENTS |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0309491A1 (en) |
| JP (1) | JPH01501864A (en) |
| DE (1) | DE3790883T1 (en) |
| GB (1) | GB2209338A (en) |
| NL (1) | NL8720745A (en) |
| SE (1) | SE8803309D0 (en) |
| WO (1) | WO1988005438A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0335770B1 (en) * | 1988-04-01 | 1997-01-15 | Merrell Pharmaceuticals Inc. | Novel fluorophosphonate nucleotide derivatives |
| US5208221A (en) * | 1990-11-29 | 1993-05-04 | Bristol-Myers Squibb Company | Antiviral (phosphonomethoxy) methoxy purine/pyrimidine derivatives |
| WO1993006112A1 (en) * | 1991-09-24 | 1993-04-01 | The Wellcome Foundation Limited | Therapeutic nucleosides |
| US5532225A (en) * | 1992-07-31 | 1996-07-02 | Sri International | Acyclic purine phosphonate nucleotide analogs as antiviral agents, and related synthetic methods |
| AU690587B2 (en) * | 1993-09-17 | 1998-04-30 | Gilead Sciences, Inc. | Method for dosing therapeutic compounds |
| US5798340A (en) | 1993-09-17 | 1998-08-25 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5717095A (en) * | 1995-12-29 | 1998-02-10 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5877166A (en) * | 1996-04-29 | 1999-03-02 | Sri International | Enantiomerically pure 2-aminopurine phosphonate nucleotide analogs as antiviral agents |
| US5922695A (en) * | 1996-07-26 | 1999-07-13 | Gilead Sciences, Inc. | Antiviral phosphonomethyoxy nucleotide analogs having increased oral bioavarilability |
| US20040224916A1 (en) | 2003-01-14 | 2004-11-11 | Gilead Sciences, Inc. | Compositions and methods for combination antiviral therapy |
| TWI471145B (en) | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | Unitary pharmaceutical dosage form |
| TWI375560B (en) | 2005-06-13 | 2012-11-01 | Gilead Sciences Inc | Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2150570B (en) * | 1983-05-24 | 1987-04-08 | Stanford Res Inst Int | Novel antiviral agents |
| CA1288098C (en) * | 1984-08-24 | 1991-08-27 | Richard L. Tolman | 4-(guanin-9-yl)butanals and their 3-oxa, 3-thia and 2-ene derivatives having antiviral and antitumor activity |
-
1987
- 1987-12-23 WO PCT/US1987/003446 patent/WO1988005438A1/en not_active Application Discontinuation
- 1987-12-23 EP EP88900934A patent/EP0309491A1/en not_active Withdrawn
- 1987-12-23 NL NL8720745A patent/NL8720745A/en not_active Application Discontinuation
- 1987-12-23 JP JP63501095A patent/JPH01501864A/en active Pending
- 1987-12-23 DE DE19873790883 patent/DE3790883T1/de not_active Withdrawn
-
1988
- 1988-09-12 GB GB8821380A patent/GB2209338A/en active Pending
- 1988-09-19 SE SE8803309A patent/SE8803309D0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL8720745A (en) | 1988-12-01 |
| GB8821380D0 (en) | 1988-11-02 |
| EP0309491A1 (en) | 1989-04-05 |
| SE8803309D0 (en) | 1988-09-19 |
| GB2209338A (en) | 1989-05-10 |
| WO1988005438A1 (en) | 1988-07-28 |
| DE3790883T1 (en) | 1988-12-08 |
| JPH01501864A (en) | 1989-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAV | Patent application has lapsed |
Ref document number: 8803309-7 Effective date: 19930701 |