NO174805B - Analogifremgangsmåte for fremstilling av terapeutisk aktive oksimkarbamater og oksim-karbonater - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive oksimkarbamater og oksim-karbonater Download PDFInfo
- Publication number
- NO174805B NO174805B NO913065A NO913065A NO174805B NO 174805 B NO174805 B NO 174805B NO 913065 A NO913065 A NO 913065A NO 913065 A NO913065 A NO 913065A NO 174805 B NO174805 B NO 174805B
- Authority
- NO
- Norway
- Prior art keywords
- mmol
- oxime
- methylene chloride
- methoxyphenyl
- cyclopentyloxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 150000002923 oximes Chemical class 0.000 claims abstract description 27
- -1 loweralkylamino Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 18
- VWNHESFEFMDDOY-UHFFFAOYSA-N 1-(3-butoxy-4-methoxyphenyl)ethanone Chemical compound CCCCOC1=CC(C(C)=O)=CC=C1OC VWNHESFEFMDDOY-UHFFFAOYSA-N 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- STUPRJVKLDILNL-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethanone Chemical compound COC1=CC=C(C(=O)CC=2C=CC=CC=2)C=C1OC1CCCC1 STUPRJVKLDILNL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- BFQYBNXJQBXNSS-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylpropan-2-one Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1CC(=O)CC1=CC=CC=C1 BFQYBNXJQBXNSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- KTQNWVIHYKDPEV-UHFFFAOYSA-N 1-[3-(3-bicyclo[2.2.1]heptanyloxy)-4-methoxyphenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1OC1C(C2)CCC2C1 KTQNWVIHYKDPEV-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- STTRYQAGHGJXJJ-LICLKQGHSA-N filaminast Chemical compound COC1=CC=C(C(\C)=N\OC(N)=O)C=C1OC1CCCC1 STTRYQAGHGJXJJ-LICLKQGHSA-N 0.000 claims 1
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- 239000008346 aqueous phase Substances 0.000 description 8
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 8
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229940033687 beuthanasia Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 208000030303 breathing problems Diseases 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 230000007883 bronchodilation Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
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- 229940029575 guanosine Drugs 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
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- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
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- MSHFRERJPWKJFX-UHFFFAOYSA-N para-methoxybenzyl alcohol Natural products COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
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- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- UVDTXTAXFIUJCQ-UHFFFAOYSA-N uranium tetrahydrate Chemical compound O.O.O.O.[U] UVDTXTAXFIUJCQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Reinforced Plastic Materials (AREA)
- Quinoline Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/564,263 US5124455A (en) | 1990-08-08 | 1990-08-08 | Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO913065D0 NO913065D0 (no) | 1991-08-07 |
| NO913065L NO913065L (no) | 1992-02-10 |
| NO174805B true NO174805B (no) | 1994-04-05 |
| NO174805C NO174805C (cs) | 1994-07-13 |
Family
ID=24253782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO913065A NO174805B (no) | 1990-08-08 | 1991-08-07 | Analogifremgangsmåte for fremstilling av terapeutisk aktive oksimkarbamater og oksim-karbonater |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5124455A (cs) |
| EP (1) | EP0470805B1 (cs) |
| JP (1) | JP2651292B2 (cs) |
| KR (1) | KR920004335A (cs) |
| CN (1) | CN1029613C (cs) |
| AT (1) | ATE111076T1 (cs) |
| AU (1) | AU640251B2 (cs) |
| CA (1) | CA2048518A1 (cs) |
| CS (1) | CS245091A3 (cs) |
| CY (1) | CY2057B1 (cs) |
| DE (1) | DE69103846T2 (cs) |
| DK (1) | DK0470805T3 (cs) |
| ES (1) | ES2060307T3 (cs) |
| FI (1) | FI913738A (cs) |
| GB (1) | GB2246777B (cs) |
| HK (1) | HK1000103A1 (cs) |
| HU (3) | HU207289B (cs) |
| IE (1) | IE66049B1 (cs) |
| IL (1) | IL99081A (cs) |
| MX (1) | MX9100549A (cs) |
| NO (1) | NO174805B (cs) |
| NZ (1) | NZ239279A (cs) |
| PT (1) | PT98596B (cs) |
| RU (1) | RU2051145C1 (cs) |
| ZA (1) | ZA916154B (cs) |
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| US5698711A (en) | 1991-01-28 | 1997-12-16 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group |
| GB9311281D0 (en) * | 1993-06-01 | 1993-07-21 | Rhone Poulenc Rorer Ltd | Novel composition of matter |
| GB9204808D0 (en) * | 1992-03-04 | 1992-04-15 | Rhone Poulenc Rorer Ltd | Novel compositions of matter |
| GB9212673D0 (en) * | 1992-06-15 | 1992-07-29 | Celltech Ltd | Chemical compounds |
| JP3775684B2 (ja) * | 1992-07-28 | 2006-05-17 | ローン−プーラン・ロレ・リミテツド | 脂肪族−またはヘテロ原子−含有連結基によりアリールまたはヘテロアリールに連結されたフェニル含有化合物 |
| US5679696A (en) * | 1992-07-28 | 1997-10-21 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic-or heteroatom-containing linking group |
| GB9222253D0 (en) * | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| US5622977A (en) * | 1992-12-23 | 1997-04-22 | Celltech Therapeutics Limited | Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same |
| GB9226830D0 (en) * | 1992-12-23 | 1993-02-17 | Celltech Ltd | Chemical compounds |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| US5502072A (en) * | 1993-11-26 | 1996-03-26 | Pfizer Inc. | Substituted oxindoles |
| GB9326173D0 (en) * | 1993-12-22 | 1994-02-23 | Celltech Ltd | Chemical compounds and process |
| DE69433594T2 (de) * | 1993-12-22 | 2004-08-05 | Celltech R&D Ltd., Slough | Trisubstituierte phenyl-derivate, verfahren zu deren herstellung und deren verwendung als phosphodiesterase (typ iv) hemmstoffe |
| US5786354A (en) * | 1994-06-21 | 1998-07-28 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| GB9412571D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412573D0 (en) * | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412672D0 (en) * | 1994-06-23 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| US6448235B1 (en) | 1994-07-11 | 2002-09-10 | University Of Virginia Patent Foundation | Method for treating restenosis with A2A adenosine receptor agonists |
| US6514949B1 (en) | 1994-07-11 | 2003-02-04 | University Of Virginia Patent Foundation | Method compositions for treating the inflammatory response |
| US5665737B1 (en) * | 1994-10-12 | 1999-02-16 | Euro Celtique Sa | Substituted benzoxazoles |
| WO1996018399A1 (en) | 1994-12-13 | 1996-06-20 | Euro-Celtique, S.A. | Aryl thioxanthines |
| US6025361A (en) * | 1994-12-13 | 2000-02-15 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| US6268373B1 (en) | 1995-06-07 | 2001-07-31 | Euro-Celtique S.A. | Trisubstituted thioxanthines |
| PT850215E (pt) | 1995-07-26 | 2001-03-30 | Pfizer | Derivados de acidos n-(aroil)glicina-hidroxamicos e compostos relacionados |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526243D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526246D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526245D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| US6075016A (en) | 1996-04-10 | 2000-06-13 | Euro-Celtique S.A. | 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity |
| GB9608435D0 (en) * | 1996-04-24 | 1996-06-26 | Celltech Therapeutics Ltd | Chemical compounds |
| US5864037A (en) | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
| EP2223920A3 (en) | 1996-06-19 | 2011-09-28 | Aventis Pharma Limited | Substituted azabicyclic compounds |
| GB9619284D0 (en) * | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| US5744473A (en) * | 1996-09-16 | 1998-04-28 | Euro-Celtique, S.A. | PDE IV inhibitors: "bis-compounds" |
| GB9622363D0 (en) * | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9625184D0 (en) * | 1996-12-04 | 1997-01-22 | Celltech Therapeutics Ltd | Chemical compounds |
| WO1998028281A1 (en) | 1996-12-23 | 1998-07-02 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives, their preparation and their use as protein tyrosine kinase inhibitors |
| US5981549A (en) * | 1997-02-14 | 1999-11-09 | Synapse Pharmaceutical International | Method for controlling or alleviating the symptoms of respiratory disease and allergies |
| GB9705361D0 (en) | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
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| ES2222614T3 (es) | 1997-11-12 | 2005-02-01 | Mitsubishi Chemical Corporation | Derivados de purina y medicina que los contiene como ingrediente activo. |
| US6117878A (en) * | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| KR100479019B1 (ko) * | 1998-05-22 | 2005-08-29 | 씨제이 주식회사 | 캐테콜히드라존유도체,이의제조방법및그를함유한약제학적조성물 |
| KR100578425B1 (ko) * | 1998-10-16 | 2007-01-11 | 씨제이 주식회사 | 캐테콜 히드라진 유도체, 이의 제조 방법 및 이를 함유한 약제학적 조성물 |
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| US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| DE60006663T2 (de) | 1999-05-11 | 2004-10-07 | Mitsubishi Chem Corp | Dihydrat eines purinderivates, medikamente die dieses als aktiven wirkstoff enthalten und zwischenprodukte zu dessen herstellung |
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| US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
| DE60043318D1 (de) | 1999-08-21 | 2010-01-14 | Nycomed Gmbh | Synergistische kombination von pumafentrine und salmeterol |
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| CA2460911C (en) * | 2001-10-01 | 2011-08-30 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
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-
1990
- 1990-08-08 US US07/564,263 patent/US5124455A/en not_active Expired - Fee Related
-
1991
- 1991-08-05 AU AU81623/91A patent/AU640251B2/en not_active Ceased
- 1991-08-05 JP JP3195183A patent/JP2651292B2/ja not_active Expired - Lifetime
- 1991-08-05 IL IL9908191A patent/IL99081A/en unknown
- 1991-08-05 ZA ZA916154A patent/ZA916154B/xx unknown
- 1991-08-06 ES ES91307197T patent/ES2060307T3/es not_active Expired - Lifetime
- 1991-08-06 AT AT91307197T patent/ATE111076T1/de active
- 1991-08-06 KR KR1019910013552A patent/KR920004335A/ko active IP Right Grant
- 1991-08-06 DE DE69103846T patent/DE69103846T2/de not_active Expired - Fee Related
- 1991-08-06 GB GB9116950A patent/GB2246777B/en not_active Expired - Fee Related
- 1991-08-06 DK DK91307197.3T patent/DK0470805T3/da active
- 1991-08-06 EP EP91307197A patent/EP0470805B1/en not_active Expired - Lifetime
- 1991-08-06 NZ NZ239279A patent/NZ239279A/xx unknown
- 1991-08-06 MX MX9100549A patent/MX9100549A/es unknown
- 1991-08-06 FI FI913738A patent/FI913738A/fi unknown
- 1991-08-07 CA CA002048518A patent/CA2048518A1/en not_active Abandoned
- 1991-08-07 PT PT98596A patent/PT98596B/pt not_active IP Right Cessation
- 1991-08-07 CS CS912450A patent/CS245091A3/cs unknown
- 1991-08-07 HU HU912634A patent/HU207289B/hu not_active IP Right Cessation
- 1991-08-07 RU SU915001278A patent/RU2051145C1/ru active
- 1991-08-07 IE IE279491A patent/IE66049B1/en not_active IP Right Cessation
- 1991-08-07 CN CN91105530A patent/CN1029613C/zh not_active Expired - Fee Related
- 1991-08-07 HU HU9202417A patent/HU215159B/hu not_active IP Right Cessation
- 1991-08-07 NO NO913065A patent/NO174805B/no unknown
-
1995
- 1995-06-28 HU HU95P/P00483P patent/HU211643A9/hu unknown
-
1997
- 1997-07-17 HK HK97101569A patent/HK1000103A1/xx not_active IP Right Cessation
-
1998
- 1998-04-30 CY CY9802057A patent/CY2057B1/xx unknown
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