US3666856A - Treating immune response with amino purine derivatives - Google Patents
Treating immune response with amino purine derivatives Download PDFInfo
- Publication number
- US3666856A US3666856A US877443A US3666856DA US3666856A US 3666856 A US3666856 A US 3666856A US 877443 A US877443 A US 877443A US 3666856D A US3666856D A US 3666856DA US 3666856 A US3666856 A US 3666856A
- Authority
- US
- United States
- Prior art keywords
- compound
- amino
- compounds
- formula
- immune response
- 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.)
- Expired - Lifetime
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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
-
- 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
Definitions
- R is amino or lower alkylamino
- R is amino or hydrogen and pharmaceutically acceptable salts thereof, provided that when R is amino, R is amino.
- the compounds are useful as immune suppressants and as antivirals.
- lower alkyl is defined as having one to four carbon atoms (i,e., methyl,ethyl, propyl, and butyl).
- the compounds of this invention may also be provided as salts and be used in pharmacological and medical applications as pharmaceutically acceptable salts, although it should be understood that the activity of any salt administered or used medically resides in the base.
- toxic salts can be made and converted to either the base or pharmaceutically acceptable salts by standard decomposition methods.
- Salts which are especially preferred for therapeutic use are salts of pharmaceutically acceptable carboxylic acids such s lactic, acetic, malic as well as salts of pharmaceutically acceptable weak mineral acids.
- the compounds of Formula I and their pharmaceutically acceptable salts are particularly useful in treating viral infections resulting from DNA viruses, of which type vaccinia and herpes are examples.
- the compounds of Formula I or their pharmaceutically acceptable salts would preferably be applied to the infected part of the body of the patient as a topical ointment.
- the compounds of this invention are also useful in treating systemic vaccinial and herpes viral infections and for such use, the compounds are preferably administered orally or parenterally.
- the compounds of Formula I or their pharmaceutically acceptable salts are also useful to suppress the immune response of an animal to the transplant of foreign cells into the body of the animal.
- the compounds of Formula I or their phannaceutically acceptable salts are also useful in the treatment of autoimmune diseases in mamals such as Lupus Erythematosis, Hemolytic anemia, Ulcerative Colitis and Nephrosis.
- the compounds of this invention are preferably used internally (orally or parenterally) for the treatment of viral infections at dose levels (as base) at about 1-100 mg./kg. of mammal bodyweight, and is preferably used in man in a unit dosage form (administered a few times daily) in the amount of to 250 mg. per unit dose depending on the patient being treated.
- dose levels as base
- unit dosage form administered a few times daily
- the amount used would be about one half of that used for internal use.
- the compounds of Formula I are administered internally at dosages preferrably of about 3 to 10 mg./kg. of mammal body weight.
- the compound where R and R are both amino is the most preferred, particularly for its extremely high antiviral activity.
- This compound, 2,6- diamino-9-(B-D-arabino furanosyl) purine has in tests been found to be an extremely effective as an antiviral agent, as for example, against the herpes virus.
- mice infected intracerebrally with 100 LD of herpes virus were injected subcutaneously with 1 mg. (50 mg./kg.) 2,6-diarnino-9-(l3-D arabinofuranosyl) purine (twice daily to a total of five doses).
- the injection is preferably a solution of the compound in a sterile fluid, i.e., water since the compound is readily soluble.
- the compound 2,6-diamino-9-(B-D-arabinofuranosyl) purine has also shown substantial and unexpectedly high activity against vaccinia virus.
- Five mice injected intracerebrally with I00 LD of Vaccinia virus were given the compound subcutaneously in a dose of l mg.(50 mg./kg.) twice a day.
- 60 percent survival were achieved with the treated mice, while all the mice of the control group died within 4- /5 days.
- the compound 2,6-diamino-9-(B-D- arabinofuranosyl) purine or its salts may be given parenterally (in an injectable solution), orally (tablets or capsules), used as a suppository, applied as an optic solution, or applied topically as an ointment, cream, powder, etc., as a pharmaceutical preparation in accordance with known medical or veterinarial practice.
- the preferred compound is preferably administered at a dosage of about 1 to mg./kg. of mammal body weight (i.e., mice, rats, dogs, humans). In a unit dosage the compound is preferably administered at a dosage of about 10-250 mg.
- the dosage is preferably one half the dosage given above, i.e., 5 to 50 mg./kg. or 5-125 mg. per unit close.
- the preferred drug or compound is preferably given orally and at a dose level of about 3 to 10 mg./kg. of mammal body weight a few times daily.
- the compounds of Formula I may be conveniently prepared by reducing (i.e., by catalytic hydrogenation) the compound of Formula II.
- Z is a blocking group such that when attached to the oxygen atom at position 2 of the sugar moiety, there is no interference with processes at carbon No. l of the sugar.
- acyl is not acceptable as Z but alkyl is.
- a further limitation is that Z should be removable, when desired, under mild conditions.
- the benzyl group satisfies both requirements and is preferred. Others that can be used are p-phenylbenzyl and a and B- menaphthyl.
- the reduction may be accomplished catalytically, i.e., by use of a hydrogenation catalyst such as palladium, palladized charcoal, platinum black,Raney nickel, or by reacting the compound of Formula II with a reducing agent such as sodium in liquid ammonia. Potassium and other alkali metals may also be used.
- a hydrogenation catalyst such as palladium, palladized charcoal, platinum black,Raney nickel
- a reducing agent such as sodium in liquid ammonia.
- Potassium and other alkali metals may also be used.
- steps (b) and (c) are reductive processes which can be combined into one step using either of the reductive methods described previously in the description for making the compounds of Formula I from the intermediates therefor.
- the present invention provides the above methods of preparation of the compound of Formula I and the preferred compound R and R NH and acid addition salts thereof.
- compositions or preparations comprising a compound of Formula I or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefore.
- the compositions may be used orally, parenterally or topically depending on whether the preparation is used to treat internal or external viral infections caused by DNA viruses.
- It is preferably administered orally or as a solution (injection) when it is an immune or autoimmunal response suppressant.
- This invention also provides a method for treating viral infections caused by DNA viruses in mammals, (i.e., mice,rats, dogs, man etc.) by administering an effective non-toxic antiviral amount of a compound of Formula I (preferably where R R NH or a salt thereof to the infected mammal.
- DNA viruses are those viruses which utilize DNA as building blocks.
- the invention also provides novel and useful compounds of the above formulas.
- fine powders or granules of the compounds may contain diluting, dispersing and/or surface active agents, and may be presented in a draft, in water or in a syrup, in capsules or cachets in the dry state or in a non-aqueous suspension wherein suspending agents may be included; in tablets, when binders and lubricants may be included; or in a suspension in water or a syrup.
- compositions may be presented in aqueous injection solutions which may contain antioxidants, buffers etc.
- the precipitated sodium chloride was filtered off, and the yellow filtrate, containing the 2,6-diazido-9-(2,3,5-tri-O-benzyl- ⁇ 3-D-arabinofuranosyl) purine showed absorption maxima at 245,270 (shoulder), 300 mu in ethanol.
- the filtrate was used directly for the reduction in the next step.
- a method of treating a mammal exhibiting an immune response as a result of the transplant of foreign cells into the body of the mammal which comprises internally administering to the mammal an effective immuno suppressant amount of the compound of Formula I or its pharmaceutically acceptable salts l AN Hoop2
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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)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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 |
---|---|---|---|
US87744369A | 1969-11-17 | 1969-11-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3666856A true US3666856A (en) | 1972-05-30 |
Family
ID=25369972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US877443A Expired - Lifetime US3666856A (en) | 1969-11-17 | 1969-11-17 | Treating immune response with amino purine derivatives |
Country Status (26)
Country | Link |
---|---|
US (1) | US3666856A (es) |
JP (1) | JPS5429520B1 (es) |
AT (1) | AT309696B (es) |
BE (1) | BE759011A (es) |
BR (1) | BR6915136D0 (es) |
CA (1) | CA967564A (es) |
CH (2) | CH555344A (es) |
CS (1) | CS181701B2 (es) |
DE (1) | DE2056327C2 (es) |
DK (1) | DK128117B (es) |
ES (2) | ES385590A1 (es) |
FI (1) | FI54315C (es) |
FR (1) | FR2073364B1 (es) |
GB (2) | GB1338906A (es) |
HU (1) | HU163812B (es) |
IE (1) | IE34737B1 (es) |
IL (1) | IL35658A (es) |
LU (1) | LU62071A1 (es) |
MC (1) | MC869A1 (es) |
NL (1) | NL171589C (es) |
NO (1) | NO128156B (es) |
PL (1) | PL81167B1 (es) |
SE (1) | SE385374B (es) |
YU (2) | YU35033B (es) |
ZA (1) | ZA707722B (es) |
ZM (1) | ZM12970A1 (es) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4081534A (en) * | 1973-09-11 | 1978-03-28 | Burroughs Wellcome Co. | Amino purine nucleosides as autoimmune suppressant agents |
US4136175A (en) * | 1975-06-17 | 1979-01-23 | Burroughs Wellcome Co. | Purine nucleotide antiveral composition and methods of use |
WO1989008658A1 (en) * | 1988-03-16 | 1989-09-21 | Scripps Clinic And Research Foundation | Substituted adenine derivatives useful as therapeutic agents |
US5034382A (en) * | 1983-05-27 | 1991-07-23 | Goedecke A.G. | Topical composition for treating herpes with adenosine |
US5292725A (en) * | 1988-08-25 | 1994-03-08 | Prendergast Patrick T | Administering particular compounds against various parasites, mycoplasmas, other indications and other infections |
US5308837A (en) * | 1990-08-22 | 1994-05-03 | Merrell Dow Pharmaceuticals Inc. | 5'-amine substituted adenosine analogs as immunosuppressants |
US5424295A (en) * | 1987-05-30 | 1995-06-13 | Burroughs Wellcome Co. | 9-β-D-arabinofuranasyl-2-amino-6-methaoxy-9H-purine |
US5681941A (en) * | 1990-01-11 | 1997-10-28 | Isis Pharmaceuticals, Inc. | Substituted purines and oligonucleotide cross-linking |
US5681831A (en) * | 1988-08-25 | 1997-10-28 | Prendergast; Patrick T. | Method of treating viral and retroviral infections including HIV by administration of N6 -(Δ)2 -isopentenyl) adenosine or an analogue thereof |
US6232463B1 (en) | 1997-10-09 | 2001-05-15 | Isis Pharmaceuticals, Inc. | Substituted purines and oligonucleotide cross-linking |
US6288069B1 (en) | 1999-11-16 | 2001-09-11 | Neotherapeutics, Inc. | Use of 9-substituted hypoxanthine derivatives to stimulate regeneration of nervous tissue |
US6303617B1 (en) | 1998-05-04 | 2001-10-16 | Neotherapeutics, Inc. | Serotonin-like 9-substituted hypoxanthine and methods of use |
US6338963B1 (en) | 1994-07-25 | 2002-01-15 | Neotherapeutics, Inc. | Use of carbon monoxide dependent guanylyl cyclase modifiers to stimulate neuritogenesis |
US6407237B1 (en) | 2001-02-21 | 2002-06-18 | Neotherapeutics, Inc. | Crystal forms of 9-substituted hypoxanthine derivatives |
US20030022892A1 (en) * | 2001-04-20 | 2003-01-30 | Glasky Alvin J. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US6630478B2 (en) | 2000-07-07 | 2003-10-07 | Neotherapeutics, Inc. | Methods for treatment of drug-induced peripheral neuropathy |
US20040116453A1 (en) * | 2001-07-17 | 2004-06-17 | Fick David B. | Synthesis and methods of use pyrimidine analogues and derivatives |
US20050014943A1 (en) * | 2000-06-23 | 2005-01-20 | Glasky Alvin J. | Methods of synthesis for 9-substituted hypoxanthine derivatives |
CN105237602A (zh) * | 2015-06-25 | 2016-01-13 | 新乡学院 | 一种2-氨基阿糖腺苷的制备方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4210745A (en) * | 1978-01-04 | 1980-07-01 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Procedure for the preparation of 9-β-D-arabinofuranosyl-2-fluoroadenine |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1070413A (en) * | 1962-11-15 | 1967-06-01 | Sankyo Co | A process for preparing purine and pyrimidine nucleosides |
US3407191A (en) * | 1966-08-29 | 1968-10-22 | Lilly Co Eli | Adamantoate esters of nucleosides |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1097965A (ja) * | 1996-09-20 | 1998-04-14 | Sony Corp | 生産管理方法 |
-
0
- BE BE759011D patent/BE759011A/xx not_active IP Right Cessation
-
1969
- 1969-11-17 US US877443A patent/US3666856A/en not_active Expired - Lifetime
- 1969-12-15 BR BR215136/69A patent/BR6915136D0/pt unknown
-
1970
- 1970-11-10 MC MC923A patent/MC869A1/xx unknown
- 1970-11-16 JP JP10095870A patent/JPS5429520B1/ja active Pending
- 1970-11-16 CH CH1694070A patent/CH555344A/xx not_active IP Right Cessation
- 1970-11-16 GB GB2751373A patent/GB1338906A/en not_active Expired
- 1970-11-16 CS CS7000007720A patent/CS181701B2/cs unknown
- 1970-11-16 IE IE1470/70A patent/IE34737B1/xx unknown
- 1970-11-16 GB GB5450270A patent/GB1338905A/en not_active Expired
- 1970-11-16 FI FI3069/70A patent/FI54315C/fi active
- 1970-11-16 SE SE7015440A patent/SE385374B/xx unknown
- 1970-11-16 NO NO04378/70A patent/NO128156B/no unknown
- 1970-11-16 ES ES385590A patent/ES385590A1/es not_active Expired
- 1970-11-16 CH CH1431873A patent/CH555833A/xx not_active IP Right Cessation
- 1970-11-16 LU LU62071D patent/LU62071A1/xx unknown
- 1970-11-16 PL PL1970144449A patent/PL81167B1/pl unknown
- 1970-11-16 CA CA098,272A patent/CA967564A/en not_active Expired
- 1970-11-16 DE DE2056327A patent/DE2056327C2/de not_active Expired
- 1970-11-16 FR FR7040956A patent/FR2073364B1/fr not_active Expired
- 1970-11-16 ZA ZA707722A patent/ZA707722B/xx unknown
- 1970-11-16 HU HUWE425A patent/HU163812B/hu unknown
- 1970-11-16 AT AT1028370A patent/AT309696B/de not_active IP Right Cessation
- 1970-11-16 DK DK581070AA patent/DK128117B/da not_active IP Right Cessation
- 1970-11-16 YU YU2806/70A patent/YU35033B/xx unknown
- 1970-11-16 NL NLAANVRAGE7016766,A patent/NL171589C/xx not_active IP Right Cessation
- 1970-11-16 IL IL35658A patent/IL35658A/en unknown
- 1970-11-17 ZM ZM129/70A patent/ZM12970A1/xx unknown
-
1973
- 1973-04-16 ES ES413787A patent/ES413787A1/es not_active Expired
-
1978
- 1978-08-24 YU YU2019/78A patent/YU35034B/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1070413A (en) * | 1962-11-15 | 1967-06-01 | Sankyo Co | A process for preparing purine and pyrimidine nucleosides |
US3407191A (en) * | 1966-08-29 | 1968-10-22 | Lilly Co Eli | Adamantoate esters of nucleosides |
Non-Patent Citations (1)
Title |
---|
Culliton, Science News, Vol. 95, pages 457 459, May 10, 1969 * |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4081534A (en) * | 1973-09-11 | 1978-03-28 | Burroughs Wellcome Co. | Amino purine nucleosides as autoimmune suppressant agents |
US4136175A (en) * | 1975-06-17 | 1979-01-23 | Burroughs Wellcome Co. | Purine nucleotide antiveral composition and methods of use |
US5034382A (en) * | 1983-05-27 | 1991-07-23 | Goedecke A.G. | Topical composition for treating herpes with adenosine |
US5424295A (en) * | 1987-05-30 | 1995-06-13 | Burroughs Wellcome Co. | 9-β-D-arabinofuranasyl-2-amino-6-methaoxy-9H-purine |
WO1989008658A1 (en) * | 1988-03-16 | 1989-09-21 | Scripps Clinic And Research Foundation | Substituted adenine derivatives useful as therapeutic agents |
US5681831A (en) * | 1988-08-25 | 1997-10-28 | Prendergast; Patrick T. | Method of treating viral and retroviral infections including HIV by administration of N6 -(Δ)2 -isopentenyl) adenosine or an analogue thereof |
US5292725A (en) * | 1988-08-25 | 1994-03-08 | Prendergast Patrick T | Administering particular compounds against various parasites, mycoplasmas, other indications and other infections |
US5681941A (en) * | 1990-01-11 | 1997-10-28 | Isis Pharmaceuticals, Inc. | Substituted purines and oligonucleotide cross-linking |
US5308837A (en) * | 1990-08-22 | 1994-05-03 | Merrell Dow Pharmaceuticals Inc. | 5'-amine substituted adenosine analogs as immunosuppressants |
US5811534A (en) * | 1994-02-01 | 1998-09-22 | Isis Pharmaceuticals, Inc. | Substituted purines and oligonucleotide cross-linking |
US6338963B1 (en) | 1994-07-25 | 2002-01-15 | Neotherapeutics, Inc. | Use of carbon monoxide dependent guanylyl cyclase modifiers to stimulate neuritogenesis |
US6232463B1 (en) | 1997-10-09 | 2001-05-15 | Isis Pharmaceuticals, Inc. | Substituted purines and oligonucleotide cross-linking |
US6303617B1 (en) | 1998-05-04 | 2001-10-16 | Neotherapeutics, Inc. | Serotonin-like 9-substituted hypoxanthine and methods of use |
US6288069B1 (en) | 1999-11-16 | 2001-09-11 | Neotherapeutics, Inc. | Use of 9-substituted hypoxanthine derivatives to stimulate regeneration of nervous tissue |
US20050014943A1 (en) * | 2000-06-23 | 2005-01-20 | Glasky Alvin J. | Methods of synthesis for 9-substituted hypoxanthine derivatives |
US6849735B1 (en) | 2000-06-23 | 2005-02-01 | Merck Eprova Ag | Methods of synthesis for 9-substituted hypoxanthine derivatives |
US6630478B2 (en) | 2000-07-07 | 2003-10-07 | Neotherapeutics, Inc. | Methods for treatment of drug-induced peripheral neuropathy |
US6630490B2 (en) | 2000-07-07 | 2003-10-07 | Neotherapeutics, Inc. | Methods for treatment of disease-induced peripheral neuropathy and related conditions |
US6407237B1 (en) | 2001-02-21 | 2002-06-18 | Neotherapeutics, Inc. | Crystal forms of 9-substituted hypoxanthine derivatives |
US20030022892A1 (en) * | 2001-04-20 | 2003-01-30 | Glasky Alvin J. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US20050096317A1 (en) * | 2001-04-20 | 2005-05-05 | Neotherapeutics, Inc. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US6982269B2 (en) | 2001-04-20 | 2006-01-03 | Spectrum Pharmaceuticals, Inc. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US7531670B2 (en) | 2001-04-20 | 2009-05-12 | Sprectrum Pharmaceuticals, Inc. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US8377456B2 (en) | 2001-04-20 | 2013-02-19 | Spectrum Pharmaceuticals, Inc. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US8734818B2 (en) | 2001-04-20 | 2014-05-27 | Spectrum Pharmaceuticals, Inc. | Methods for treating cognitive/attention deficit disorders using tetrahydroindolone analogues and derivatives |
US20040116453A1 (en) * | 2001-07-17 | 2004-06-17 | Fick David B. | Synthesis and methods of use pyrimidine analogues and derivatives |
CN105237602A (zh) * | 2015-06-25 | 2016-01-13 | 新乡学院 | 一种2-氨基阿糖腺苷的制备方法 |
CN105237602B (zh) * | 2015-06-25 | 2018-05-18 | 新乡学院 | 一种2-氨基阿糖腺苷的制备方法 |
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