NZ262984A - Use of xanthine derivatives in the preparation of medicaments - Google Patents
Use of xanthine derivatives in the preparation of medicamentsInfo
- Publication number
- NZ262984A NZ262984A NZ262984A NZ26298494A NZ262984A NZ 262984 A NZ262984 A NZ 262984A NZ 262984 A NZ262984 A NZ 262984A NZ 26298494 A NZ26298494 A NZ 26298494A NZ 262984 A NZ262984 A NZ 262984A
- Authority
- NZ
- New Zealand
- Prior art keywords
- dione
- dihydro
- purine
- dipropyl
- yield
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 13
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title description 5
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title description 4
- 230000007278 cognition impairment Effects 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 nitro, amino, hydroxy Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- MFDOIDPESZOBLK-AWEZNQCLSA-N 8-[(2s)-1-phenylpropan-2-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound C([C@H](C)C1=NC=2N(C(N(CCC)C(=O)C=2N1)=O)CCC)C1=CC=CC=C1 MFDOIDPESZOBLK-AWEZNQCLSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 132
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 72
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 55
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 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 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- 150000001408 amides Chemical class 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000004587 chromatography analysis Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 26
- 235000019341 magnesium sulphate Nutrition 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 239000000284 extract Substances 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 21
- 229960005305 adenosine Drugs 0.000 description 21
- 235000019441 ethanol Nutrition 0.000 description 20
- 102000005962 receptors Human genes 0.000 description 20
- 108020003175 receptors Proteins 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 229940075420 xanthine Drugs 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 239000012528 membrane Substances 0.000 description 17
- 238000003818 flash chromatography Methods 0.000 description 16
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 16
- 108050000203 Adenosine receptors Proteins 0.000 description 15
- 102000009346 Adenosine receptors Human genes 0.000 description 15
- 230000027455 binding Effects 0.000 description 15
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
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- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 11
- 239000005557 antagonist Substances 0.000 description 11
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 11
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- 241001465754 Metazoa Species 0.000 description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 9
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- 239000003826 tablet Substances 0.000 description 8
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- CHMUHOFITZIING-XNIJJKJLSA-N (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-2-cyclohexyl-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@]1(C2CCCCC2)O[C@H](CO)[C@@H](O)[C@H]1O CHMUHOFITZIING-XNIJJKJLSA-N 0.000 description 6
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- MCIIDRLDHRQKPH-UHFFFAOYSA-N 2-methyl-3-phenylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=CC=C1 MCIIDRLDHRQKPH-UHFFFAOYSA-N 0.000 description 6
- SVMBOONGPUFHRA-UHFFFAOYSA-N 5,6-diamino-1,3-dipropylpyrimidine-2,4-dione Chemical compound CCCN1C(N)=C(N)C(=O)N(CCC)C1=O SVMBOONGPUFHRA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- RUHGOZFOVBMWOO-UHFFFAOYSA-N 8-(3-oxocyclopentyl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1CCC(=O)C1 RUHGOZFOVBMWOO-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2350193A | 1993-02-26 | 1993-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ262984A true NZ262984A (en) | 1997-05-26 |
Family
ID=21815459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ262984A NZ262984A (en) | 1993-02-26 | 1994-01-27 | Use of xanthine derivatives in the preparation of medicaments |
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| CA (1) | CA2155130C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69412073T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK0686155T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2120025T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUT72677A (cg-RX-API-DMAC7.html) |
| IL (1) | IL108750A (cg-RX-API-DMAC7.html) |
| MX (1) | MX9401406A (cg-RX-API-DMAC7.html) |
| NO (1) | NO311920B1 (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ262984A (cg-RX-API-DMAC7.html) |
| TW (1) | TW261532B (cg-RX-API-DMAC7.html) |
| WO (1) | WO1994019349A1 (cg-RX-API-DMAC7.html) |
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998041237A1 (en) * | 1997-03-18 | 1998-09-24 | Fujisawa Pharmaceutical Co., Ltd. | Preventives and remedies for hyperphosphatemia |
| JP4611524B2 (ja) | 1998-06-02 | 2011-01-12 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | ピロロ［２，３ｄ］ピリミジン組成物およびその使用 |
| US6680322B2 (en) | 1999-12-02 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US6680324B2 (en) | 2000-12-01 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US20020115635A1 (en) * | 2001-02-21 | 2002-08-22 | Pnina Fishman | Modulation of GSK-3beta activity and its different uses |
| ATE446298T1 (de) | 2001-11-30 | 2009-11-15 | Osi Pharm Inc | Verbindungen, die für adenosin a1 und a3 rezeptoren spezifisch sind, und deren anwendungen |
| EA007468B1 (ru) | 2001-12-20 | 2006-10-27 | Оси Фармасьютикалз, Инк. | Пиримидиновые соединения, относящиеся к a-селективным антагонистам, их синтез и применение |
| US6846958B2 (en) * | 2002-05-15 | 2005-01-25 | Genzyme Corporation | Synthesis of benzimidate from benzoic acid |
| WO2004086047A2 (en) * | 2003-03-28 | 2004-10-07 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g-protein-coupled receptor adenosine a1 (adora1) |
| BRPI0417241A (pt) * | 2003-12-09 | 2007-03-06 | Kyowa Hakko Kogyo Kk | agente e processo para a prevenção e/ou para o tratamento de disfunção do cérebro superior, e, uso de um derivado de xantina, ou um sal farmaceuticamente aceitável do mesmo |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| WO2007095161A2 (en) * | 2006-02-14 | 2007-08-23 | New York University | Methods and compositions for treating disorders associated with increased bone turnover and osteopenia |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE8817122U1 (de) * | 1988-12-22 | 1993-02-04 | Boehringer Ingelheim Kg, 55218 Ingelheim | Neue Xanthinderivate mit Adenosinantogenistischer Wirkung |
| US5047534A (en) * | 1990-03-26 | 1991-09-10 | Merrell Dow Pharmaceuticals Inc. | Selective adenosine receptor agents |
| DE4019892A1 (de) * | 1990-06-22 | 1992-01-02 | Boehringer Ingelheim Kg | Neue xanthinderivate |
| JPH0455150A (ja) * | 1990-06-22 | 1992-02-21 | Takata Kk | 助手席用エアバッグ装置 |
| US5087827A (en) * | 1991-02-11 | 1992-02-11 | Tektronix, Inc. | Variable voltage transition circuit |
| US5208240A (en) * | 1991-03-12 | 1993-05-04 | Merrell Dow Pharmaceuticals Inc. | 8-substituted purines as selective adenosine receptor agents |
| US5281607B1 (en) * | 1992-10-08 | 1998-05-19 | Univ New York | Method of using alpha 2-antagonists for the treatment of neurodegenerative diseases |
-
1994
- 1994-01-27 AU AU62968/94A patent/AU680241B2/en not_active Ceased
- 1994-01-27 KR KR1019950703577A patent/KR100315898B1/ko not_active Expired - Fee Related
- 1994-01-27 EP EP94910661A patent/EP0686155B1/en not_active Expired - Lifetime
- 1994-01-27 JP JP6518986A patent/JPH08512281A/ja active Pending
- 1994-01-27 ES ES94910661T patent/ES2120025T3/es not_active Expired - Lifetime
- 1994-01-27 CA CA002155130A patent/CA2155130C/en not_active Expired - Fee Related
- 1994-01-27 WO PCT/US1994/001009 patent/WO1994019349A1/en not_active Ceased
- 1994-01-27 DK DK94910661T patent/DK0686155T3/da active
- 1994-01-27 AT AT94910661T patent/ATE169019T1/de not_active IP Right Cessation
- 1994-01-27 HU HU9502495A patent/HUT72677A/hu unknown
- 1994-01-27 CN CN94191309A patent/CN1041418C/zh not_active Expired - Fee Related
- 1994-01-27 NZ NZ262984A patent/NZ262984A/en unknown
- 1994-01-27 DE DE69412073T patent/DE69412073T2/de not_active Expired - Fee Related
- 1994-01-27 US US08/500,991 patent/US5840729A/en not_active Expired - Fee Related
- 1994-02-21 ZA ZA941176A patent/ZA941176B/xx unknown
- 1994-02-22 TW TW083101485A patent/TW261532B/zh active
- 1994-02-23 IL IL10875094A patent/IL108750A/xx not_active IP Right Cessation
- 1994-02-24 MX MX9401406A patent/MX9401406A/es not_active IP Right Cessation
-
1995
- 1995-08-25 NO NO19953353A patent/NO311920B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU680241B2 (en) | 1997-07-24 |
| EP0686155B1 (en) | 1998-07-29 |
| ZA941176B (en) | 1994-09-20 |
| DK0686155T3 (da) | 1999-02-01 |
| DE69412073T2 (de) | 1999-02-18 |
| CA2155130A1 (en) | 1994-09-01 |
| JPH08512281A (ja) | 1996-12-24 |
| CN1041418C (zh) | 1998-12-30 |
| NO953353L (no) | 1995-08-25 |
| MX9401406A (es) | 1994-08-31 |
| EP0686155A1 (en) | 1995-12-13 |
| ES2120025T3 (es) | 1998-10-16 |
| TW261532B (cg-RX-API-DMAC7.html) | 1995-11-01 |
| CA2155130C (en) | 1994-09-01 |
| KR100315898B1 (ko) | 2002-02-28 |
| CN1118599A (zh) | 1996-03-13 |
| ATE169019T1 (de) | 1998-08-15 |
| US5840729A (en) | 1998-11-24 |
| HU9502495D0 (en) | 1995-10-30 |
| DE69412073D1 (de) | 1998-09-03 |
| WO1994019349A1 (en) | 1994-09-01 |
| NO311920B1 (no) | 2002-02-18 |
| IL108750A0 (en) | 1994-05-30 |
| HUT72677A (en) | 1996-05-28 |
| NO953353D0 (no) | 1995-08-25 |
| AU6296894A (en) | 1994-09-14 |
| IL108750A (en) | 2000-09-28 |
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