CA1172168A - Deazapurine nucleoside, formulations thereof, and use thereof in therapy - Google Patents
Deazapurine nucleoside, formulations thereof, and use thereof in therapyInfo
- Publication number
- CA1172168A CA1172168A CA000375956A CA375956A CA1172168A CA 1172168 A CA1172168 A CA 1172168A CA 000375956 A CA000375956 A CA 000375956A CA 375956 A CA375956 A CA 375956A CA 1172168 A CA1172168 A CA 1172168A
- Authority
- CA
- Canada
- Prior art keywords
- formulation
- active ingredient
- effective
- unit dosage
- dosage form
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 26
- 238000009472 formulation Methods 0.000 title claims description 24
- 239000002777 nucleoside Substances 0.000 title 1
- 150000003833 nucleoside derivatives Chemical class 0.000 title 1
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 16
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 10
- 239000002674 ointment Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 5
- 239000004264 Petrolatum Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 229940066842 petrolatum Drugs 0.000 claims description 3
- 235000019271 petrolatum Nutrition 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 3
- 239000004166 Lanolin Substances 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 235000015110 jellies Nutrition 0.000 claims description 2
- 229940039717 lanolin Drugs 0.000 claims description 2
- 235000019388 lanolin Nutrition 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229940068917 polyethylene glycols Drugs 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 9
- 239000008274 jelly Substances 0.000 claims 1
- DBZQFUNLCALWDY-PNHWDRBUSA-N (2r,3r,4s,5r)-2-(4-aminoimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=CC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O DBZQFUNLCALWDY-PNHWDRBUSA-N 0.000 abstract description 31
- 206010061218 Inflammation Diseases 0.000 abstract description 13
- 230000004054 inflammatory process Effects 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000012049 topical pharmaceutical composition Substances 0.000 abstract description 5
- 241000124008 Mammalia Species 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 11
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 7
- 229960001138 acetylsalicylic acid Drugs 0.000 description 7
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 208000009386 Experimental Arthritis Diseases 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229940124599 anti-inflammatory drug Drugs 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 210000000416 exudates and transudate Anatomy 0.000 description 3
- 229960000890 hydrocortisone Drugs 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229960005205 prednisolone Drugs 0.000 description 3
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000219061 Rheum Species 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 208000008423 pleurisy Diseases 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- 208000032529 Accidental overdose Diseases 0.000 description 1
- 208000018380 Chemical injury Diseases 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 102100030612 Mast cell carboxypeptidase A Human genes 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101150114843 Mgll gene Proteins 0.000 description 1
- 108091006676 Monovalent cation:proton antiporter-3 Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000008952 bacterial invasion Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 208000035850 clinical syndrome Diseases 0.000 description 1
- 230000002089 crippling effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000008629 immune suppression Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940099563 lactobionic acid Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000002089 prostaglandin antagonist Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 succinic acld Chemical compound 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- C07H19/052—Imidazole radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Biotechnology (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8013411 | 1980-04-23 | ||
| GB8013411A GB2074858B (en) | 1980-04-23 | 1980-04-23 | Compositions containing 3-deazaaden-osine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1172168A true CA1172168A (en) | 1984-08-07 |
Family
ID=10512973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000375956A Expired CA1172168A (en) | 1980-04-23 | 1981-04-22 | Deazapurine nucleoside, formulations thereof, and use thereof in therapy |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0038567B1 (en, 2012) |
| JP (1) | JPS56166118A (en, 2012) |
| AU (1) | AU553680B2 (en, 2012) |
| BE (1) | BE888525A (en, 2012) |
| CA (1) | CA1172168A (en, 2012) |
| CH (1) | CH654316A5 (en, 2012) |
| DE (2) | DE3116029A1 (en, 2012) |
| DK (1) | DK179781A (en, 2012) |
| GB (1) | GB2074858B (en, 2012) |
| IE (2) | IE51738B1 (en, 2012) |
| IL (1) | IL62696A (en, 2012) |
| IT (1) | IT1170910B (en, 2012) |
| NL (1) | NL8101987A (en, 2012) |
| NZ (1) | NZ196883A (en, 2012) |
| ZA (1) | ZA812640B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU596637B2 (en) * | 1986-08-06 | 1990-05-10 | Sumitomo Chemical Company, Limited | Mulching film for repelling insect pests |
| US4918060A (en) * | 1987-09-04 | 1990-04-17 | The Johns Hopkins University | Method of treating myasthenia gravis and related diseases |
| US5137876A (en) * | 1990-10-12 | 1992-08-11 | Merck & Co., Inc. | Nucleoside antiviral and anti-inflammatory compounds and compositions and methods for using same |
| US5698533A (en) * | 1994-07-26 | 1997-12-16 | Kang; Meng-Che | Ophthalmic pharmaceutical composition |
| US6495579B1 (en) | 1996-12-02 | 2002-12-17 | Angiotech Pharmaceuticals, Inc. | Method for treating multiple sclerosis |
| US6515016B2 (en) * | 1996-12-02 | 2003-02-04 | Angiotech Pharmaceuticals, Inc. | Composition and methods of paclitaxel for treating psoriasis |
| EP1107765B1 (en) * | 1998-09-03 | 2006-08-09 | Kerckhoff-Klink Gesellschaft mit Beschrankter Haftung | 3-deazaadenosine used in the prevention of atherosclerosis and graft vasculopathy |
| JP2002274626A (ja) * | 2001-03-19 | 2002-09-25 | Okamura Corp | ローラコンベヤ装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148888A (en) * | 1978-03-13 | 1979-04-10 | The United States Of America As Represented By The Department Of Health, Education And Welfare | 3-Deazaadenosine as an inhibitor of adenosylhomocysteine hydrolase with antiviral activity |
| EP0010668B1 (en) * | 1978-10-13 | 1986-01-22 | The Wellcome Foundation Limited | 3-deazaadenosine and pharmaceutical compositions containing it |
-
1980
- 1980-04-23 GB GB8013411A patent/GB2074858B/en not_active Expired
-
1981
- 1981-04-22 IL IL62696A patent/IL62696A/xx unknown
- 1981-04-22 IT IT48327/81A patent/IT1170910B/it active
- 1981-04-22 IE IE1594/81A patent/IE51738B1/en unknown
- 1981-04-22 NZ NZ196883A patent/NZ196883A/en unknown
- 1981-04-22 JP JP6111581A patent/JPS56166118A/ja active Granted
- 1981-04-22 DE DE19813116029 patent/DE3116029A1/de active Granted
- 1981-04-22 CH CH2640/81A patent/CH654316A5/de not_active IP Right Cessation
- 1981-04-22 CA CA000375956A patent/CA1172168A/en not_active Expired
- 1981-04-22 EP EP81103043A patent/EP0038567B1/en not_active Expired
- 1981-04-22 DE DE8181103043T patent/DE3176462D1/de not_active Expired
- 1981-04-22 DK DK179781A patent/DK179781A/da not_active Application Discontinuation
- 1981-04-22 IE IE891/81A patent/IE51737B1/en unknown
- 1981-04-22 BE BE0/204577A patent/BE888525A/fr not_active IP Right Cessation
- 1981-04-22 ZA ZA00812640A patent/ZA812640B/xx unknown
- 1981-04-22 NL NL8101987A patent/NL8101987A/nl not_active Application Discontinuation
- 1981-04-22 AU AU69710/81A patent/AU553680B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| NL8101987A (nl) | 1981-11-16 |
| AU553680B2 (en) | 1986-07-24 |
| ZA812640B (en) | 1982-12-29 |
| IE811594L (en) | 1981-10-23 |
| JPH0428686B2 (en, 2012) | 1992-05-15 |
| NZ196883A (en) | 1984-07-31 |
| IL62696A0 (en) | 1981-06-29 |
| EP0038567B1 (en) | 1987-09-23 |
| DE3116029C2 (en, 2012) | 1991-01-17 |
| DE3116029A1 (de) | 1982-03-18 |
| EP0038567A1 (en) | 1981-10-28 |
| CH654316A5 (de) | 1986-02-14 |
| IT1170910B (it) | 1987-06-03 |
| IL62696A (en) | 1984-03-30 |
| AU6971081A (en) | 1981-10-29 |
| BE888525A (fr) | 1981-10-22 |
| DE3176462D1 (en) | 1987-10-29 |
| GB2074858B (en) | 1985-03-20 |
| JPS56166118A (en) | 1981-12-21 |
| IT8148327A0 (it) | 1981-04-22 |
| IE810891L (en) | 1981-10-23 |
| GB2074858A (en) | 1981-11-11 |
| IE51737B1 (en) | 1987-03-18 |
| DK179781A (da) | 1981-10-24 |
| IE51738B1 (en) | 1987-03-18 |
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