FI111254B - Menetelmä terapeuttisesti käyttökelpoisten substituoitujen pyratsoliyhdisteiden valmistamiseksi - Google Patents
Menetelmä terapeuttisesti käyttökelpoisten substituoitujen pyratsoliyhdisteiden valmistamiseksi Download PDFInfo
- Publication number
- FI111254B FI111254B FI935672A FI935672A FI111254B FI 111254 B FI111254 B FI 111254B FI 935672 A FI935672 A FI 935672A FI 935672 A FI935672 A FI 935672A FI 111254 B FI111254 B FI 111254B
- Authority
- FI
- Finland
- Prior art keywords
- process according
- compound
- formula
- ylmethyl
- pyrazol
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 17
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- -1 2,4,6-trisubstituted phenyl Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- WPBWAPRNKZZQTQ-UHFFFAOYSA-N 2-[[3,5-diethyl-1-(2,4,6-trimethylphenyl)pyrazol-4-yl]methyl]-3-(methoxymethyl)-3,4-dihydro-1h-isoquinoline Chemical compound CCC1=C(CN2C(CC3=CC=CC=C3C2)COC)C(CC)=NN1C1=C(C)C=C(C)C=C1C WPBWAPRNKZZQTQ-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 abstract description 10
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 abstract description 10
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
- 239000005557 antagonist Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 208000019901 Anxiety disease Diseases 0.000 abstract description 3
- 230000036506 anxiety Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZSKDXMLMMQFHGW-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-3-ylmethanol Chemical compound C1=CC=C2CNC(CO)CC2=C1 ZSKDXMLMMQFHGW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- 201000010099 disease Diseases 0.000 description 6
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- 238000000746 purification Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Medicinal Chemistry (AREA)
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- Diabetes (AREA)
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- Molecular Biology (AREA)
- Oncology (AREA)
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- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99222892A | 1992-12-17 | 1992-12-17 | |
| US99222892 | 1992-12-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI935672A0 FI935672A0 (fi) | 1993-12-16 |
| FI935672L FI935672L (fi) | 1994-06-18 |
| FI111254B true FI111254B (fi) | 2003-06-30 |
Family
ID=25538068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI935672A FI111254B (fi) | 1992-12-17 | 1993-12-16 | Menetelmä terapeuttisesti käyttökelpoisten substituoitujen pyratsoliyhdisteiden valmistamiseksi |
Country Status (26)
| Country | Link |
|---|---|
| EP (2) | EP0959074A3 (cs) |
| JP (1) | JP2781661B2 (cs) |
| KR (1) | KR100190730B1 (cs) |
| CN (1) | CN1045293C (cs) |
| AT (1) | ATE187451T1 (cs) |
| AU (1) | AU690079B2 (cs) |
| BR (1) | BR9307664A (cs) |
| CA (1) | CA2150703C (cs) |
| CZ (1) | CZ287925B6 (cs) |
| DE (1) | DE69327254T2 (cs) |
| DK (1) | DK0674631T3 (cs) |
| EG (1) | EG20440A (cs) |
| ES (1) | ES2139676T3 (cs) |
| FI (1) | FI111254B (cs) |
| GR (1) | GR3032461T3 (cs) |
| HU (1) | HUT65822A (cs) |
| IL (1) | IL107947A (cs) |
| MY (1) | MY109522A (cs) |
| NO (1) | NO307884B1 (cs) |
| NZ (1) | NZ256620A (cs) |
| PL (1) | PL175982B1 (cs) |
| PT (1) | PT674631E (cs) |
| RU (1) | RU2130453C1 (cs) |
| TW (1) | TW237455B (cs) |
| WO (1) | WO1994013661A1 (cs) |
| ZA (1) | ZA939406B (cs) |
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| BR9407799A (pt) | 1993-10-12 | 1997-05-06 | Du Pont Merck Pharma | Composição de matéria método de tratamento e composição farmaceutica |
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| 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 |
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| GB9526245D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9608435D0 (en) * | 1996-04-24 | 1996-06-26 | Celltech Therapeutics Ltd | Chemical compounds |
| US6011052A (en) * | 1996-04-30 | 2000-01-04 | Warner-Lambert Company | Pyrazolone derivatives as MCP-1 antagonists |
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| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
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| GB9619284D0 (en) * | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| US6159980A (en) * | 1996-09-16 | 2000-12-12 | Dupont Pharmaceuticals Company | Pyrazinones and triazinones and their derivatives thereof |
| GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| US5760225A (en) * | 1996-11-15 | 1998-06-02 | Neurogen Corporation | Certain pyrazole derivatives as corticotropin-releasing factor receptor CRF1 specific ligands |
| GB9625184D0 (en) * | 1996-12-04 | 1997-01-22 | Celltech Therapeutics Ltd | Chemical compounds |
| JP2001507349A (ja) * | 1996-12-23 | 2001-06-05 | セルテック セラピューティックス リミテッド | 縮合多環式２−アミノピリミジン誘導体、それらの製造およびたんぱく質チロシンキナーゼ抑制因子としてのそれらの使用 |
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| US6472402B1 (en) | 1998-04-02 | 2002-10-29 | Neurogen Corporation | Aminoalkyl substituted 5,6,7,8-Tetrahydro-9H-Pyridino [2,3-B]indole derivatives |
| JP2002510686A (ja) | 1998-04-02 | 2002-04-09 | ニューロゲン コーポレイション | アミノアルキルで置換された５，６，７，８−テトラヒドロ−９Ｈ−ピリジノ［２，３−ｂ］インドール及び５，６，７，８−テトラヒドロ−９Ｈピリミジノ［４，５−Ｂ］インドール誘導体：ＣＲＦ１特異的配位子 |
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| KR20010080402A (ko) | 1998-11-12 | 2001-08-22 | 추후기재 | Ｃｒｆ 수용체 길항제 및 그와 관련된 방법 |
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| US6506784B1 (en) | 1999-07-01 | 2003-01-14 | 3-Dimensional Pharmaceuticals, Inc. | Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides |
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| TWI271406B (en) | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| US6569885B1 (en) | 1999-12-23 | 2003-05-27 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| WO2001058489A1 (fr) * | 2000-02-14 | 2001-08-16 | Japan Tobacco Inc. | Agents prophylactiques/therapeutiques contre le stress postoperatoire |
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| GB0016787D0 (en) | 2000-07-07 | 2000-08-30 | Pfizer Ltd | Compounds useful in therapy |
| GB0024795D0 (en) * | 2000-10-10 | 2000-11-22 | Hoffmann La Roche | Pyrazole derivatives for the treatment of viral diseases |
| US20060287335A1 (en) | 2000-11-28 | 2006-12-21 | Wyeth | Serotonergic agents for treating sexual dysfunction |
| US20060223824A1 (en) | 2000-11-28 | 2006-10-05 | Wyeth | Serotonergic agents |
| TWI312347B (en) | 2001-02-08 | 2009-07-21 | Eisai R&D Man Co Ltd | Bicyclic nitrogen-containing condensed ring compounds |
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| MXPA03010810A (es) | 2001-05-29 | 2004-03-22 | Schering Ag | Pirimidinas inhibidoras de cdk, su obtencion y su uso como medicamentos. |
| IL144900A (en) | 2001-08-14 | 2013-12-31 | Neurim Pharma 1991 | Melatonin and drugs containing it for use in the treatment of primary insomnia, and the manufacture of those drugs |
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| DE60334016D1 (de) | 2002-11-05 | 2010-10-14 | Glaxo Group Ltd | Antibakterielle mittel |
| KR20050085636A (ko) | 2002-12-13 | 2005-08-29 | 워너-램버트 캄파니 엘엘씨 | 섬유근육통 및 기타 질환의 치료를 위한 프레가발린 유도체 |
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| WO2007073300A1 (en) * | 2005-12-23 | 2007-06-28 | Astrazeneca Ab | Gaba-b receptor modulators |
| CA2656715A1 (en) * | 2006-07-21 | 2008-01-24 | Irm Llc | Compounds and compositions as itpkb inhibitors |
| TW200901974A (en) | 2007-01-16 | 2009-01-16 | Wyeth Corp | Compounds, compositions, and methods of making and using them |
| MX2009013215A (es) | 2007-06-15 | 2010-01-25 | Irm Llc | Compuestos y composiciones como inhibidores de itpkb. |
| WO2009104080A2 (en) | 2008-02-20 | 2009-08-27 | Targia Pharmaceuticals | Cns pharmaceutical compositions and methods of use |
| HRP20121021T1 (hr) | 2008-04-15 | 2013-01-31 | Eisai R&D Management Co., Ltd. | SPOJ 3-FENILPIRAZOLO[5,1-b]TIAZOLA |
| WO2009128057A2 (en) | 2008-04-18 | 2009-10-22 | UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al | Psycho-pharmaceuticals |
| AR078521A1 (es) | 2009-10-08 | 2011-11-16 | Eisai R&D Man Co Ltd | Compuesto pirazolotiazol |
| DE102013002393A1 (de) | 2013-02-13 | 2014-08-14 | Rauch Landmaschinenfabrik Gmbh | Verfahren zur Regelung des Massenstromes an Streugut bei einem Scheibenstreuer |
| CN114716389A (zh) * | 2021-12-31 | 2022-07-08 | 北京岳达生物科技有限公司 | 一种3,5-二乙基异恶唑-4-羧酸的合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1427781A1 (ru) * | 1987-02-13 | 1992-04-23 | Научно-исследовательский институт фармакологии АМН СССР | 4-Аминокарбонил- или 4-аминоэтил-5-метилпиразолы, обладающие способностью регулировать скорость выведени этанола |
| US5063245A (en) * | 1990-03-28 | 1991-11-05 | Nova Pharmaceutical Corporation | Corticotropin-releasing factor antagonism compounds |
-
1993
- 1993-09-30 WO PCT/US1993/009170 patent/WO1994013661A1/en active IP Right Grant
- 1993-09-30 EP EP99109027A patent/EP0959074A3/en not_active Withdrawn
- 1993-09-30 NZ NZ256620A patent/NZ256620A/en unknown
- 1993-09-30 AU AU51413/93A patent/AU690079B2/en not_active Ceased
- 1993-09-30 CZ CZ19951582A patent/CZ287925B6/cs not_active IP Right Cessation
- 1993-09-30 JP JP6506653A patent/JP2781661B2/ja not_active Expired - Fee Related
- 1993-09-30 PT PT93922407T patent/PT674631E/pt unknown
- 1993-09-30 DK DK93922407T patent/DK0674631T3/da active
- 1993-09-30 RU RU95113965/04A patent/RU2130453C1/ru not_active IP Right Cessation
- 1993-09-30 ES ES93922407T patent/ES2139676T3/es not_active Expired - Lifetime
- 1993-09-30 AT AT93922407T patent/ATE187451T1/de not_active IP Right Cessation
- 1993-09-30 CA CA002150703A patent/CA2150703C/en not_active Expired - Fee Related
- 1993-09-30 EP EP93922407A patent/EP0674631B1/en not_active Expired - Lifetime
- 1993-09-30 DE DE69327254T patent/DE69327254T2/de not_active Expired - Fee Related
- 1993-09-30 BR BR9307664A patent/BR9307664A/pt not_active Application Discontinuation
- 1993-09-30 KR KR1019950702479A patent/KR100190730B1/ko not_active Expired - Fee Related
- 1993-10-02 TW TW082108104A patent/TW237455B/zh active
- 1993-12-09 IL IL10794793A patent/IL107947A/en not_active IP Right Cessation
- 1993-12-10 MY MYPI93002671A patent/MY109522A/en unknown
- 1993-12-12 EG EG78493A patent/EG20440A/xx active
- 1993-12-15 ZA ZA939406A patent/ZA939406B/xx unknown
- 1993-12-16 FI FI935672A patent/FI111254B/fi not_active IP Right Cessation
- 1993-12-16 HU HU9303615A patent/HUT65822A/hu not_active Application Discontinuation
- 1993-12-16 CN CN93120122A patent/CN1045293C/zh not_active Expired - Fee Related
-
1995
- 1995-05-31 PL PL93309355A patent/PL175982B1/pl not_active IP Right Cessation
- 1995-06-16 NO NO952397A patent/NO307884B1/no not_active IP Right Cessation
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2000
- 2000-01-25 GR GR20000400155T patent/GR3032461T3/el not_active IP Right Cessation
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| MA | Patent expired |