PH26955A - Novel 1,7-fused 1H-indole-2-carboxylic acid N-(1,4-benzodiazepin-3-YL) amides - Google Patents
Novel 1,7-fused 1H-indole-2-carboxylic acid N-(1,4-benzodiazepin-3-YL) amides Download PDFInfo
- Publication number
- PH26955A PH26955A PH40052A PH40052A PH26955A PH 26955 A PH26955 A PH 26955A PH 40052 A PH40052 A PH 40052A PH 40052 A PH40052 A PH 40052A PH 26955 A PH26955 A PH 26955A
- Authority
- PH
- Philippines
- Prior art keywords
- represents hydrogen
- halogen
- lower alkyl
- methyl
- formula
- Prior art date
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- ZDPSGFYSVVWKBE-UHFFFAOYSA-N n-(1h-1,4-benzodiazepin-3-yl)-1h-indole-2-carboxamide Chemical class N1C2=CC=CC=C2C=NC(NC(=O)C=2NC3=CC=CC=C3C=2)=C1 ZDPSGFYSVVWKBE-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- 239000001257 hydrogen Substances 0.000 claims abstract description 49
- 150000002367 halogens Chemical group 0.000 claims abstract description 40
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 5
- 229930192474 thiophene Natural products 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 18
- 239000002253 acid Substances 0.000 claims description 61
- -1 methoxy, methyl Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 7
- 229910052731 fluorine Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- NSGCECVNIHAAIE-UHFFFAOYSA-N 2,3-dihydro-1h-1,4-benzodiazepine Chemical compound N1CCN=CC2=CC=CC=C21 NSGCECVNIHAAIE-UHFFFAOYSA-N 0.000 claims 1
- 101100165798 Arabidopsis thaliana CYP86A1 gene Proteins 0.000 claims 1
- 241000282461 Canis lupus Species 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 218
- 239000000243 solution Substances 0.000 description 100
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000011541 reaction mixture Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 28
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000012043 crude product Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 17
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- 241001465754 Metazoa Species 0.000 description 14
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- 238000010609 cell counting kit-8 assay Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000003480 eluent Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 13
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 12
- 108010087230 Sincalide Proteins 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 210000002784 stomach Anatomy 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3907390A DE3907390A1 (de) | 1989-03-08 | 1989-03-08 | Neue 1,7-anellierte 1h-indol-2-carbonsaeure-n-(5-phenyl-1,4-benzodiazepin-3-yl)amide |
| DE3907389A DE3907389A1 (de) | 1989-03-08 | 1989-03-08 | Neue 1,7-anellierte 1h-indol-carbonsaeure-n-(5-alkyl-1,4-benzodiazepin-3-yl)amide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26955A true PH26955A (en) | 1992-12-03 |
Family
ID=25878542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH40052A PH26955A (en) | 1989-03-08 | 1990-02-14 | Novel 1,7-fused 1H-indole-2-carboxylic acid N-(1,4-benzodiazepin-3-YL) amides |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5010076A (no) |
| EP (1) | EP0387618B1 (no) |
| JP (1) | JP3010558B2 (no) |
| KR (1) | KR920003627B1 (no) |
| CN (1) | CN1032208C (no) |
| AT (1) | ATE109146T1 (no) |
| AU (1) | AU616835B2 (no) |
| CS (1) | CS390091A3 (no) |
| DE (1) | DE59006544D1 (no) |
| DK (1) | DK0387618T3 (no) |
| ES (1) | ES2057216T3 (no) |
| FI (1) | FI92486C (no) |
| HK (1) | HK1006570A1 (no) |
| HU (2) | HU207317B (no) |
| IE (1) | IE65030B1 (no) |
| IL (1) | IL93401A (no) |
| NO (1) | NO173869C (no) |
| NZ (1) | NZ232774A (no) |
| PH (1) | PH26955A (no) |
| PT (1) | PT93360B (no) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07103105B2 (ja) * | 1989-05-12 | 1995-11-08 | 杏林製薬株式会社 | インドール誘導体及びその製造方法 |
| US5264419A (en) * | 1990-08-31 | 1993-11-23 | Warner-Lambert Company | N-substituted cycloalkyl and polycycloalkyl α-substituted TRP derivatives |
| CA2068355A1 (en) * | 1991-05-14 | 1992-11-15 | Mark S. Chambers | Benzodiazephine derivatives, compositions containing them and their use in therapy |
| DE4128015A1 (de) * | 1991-08-23 | 1993-02-25 | Kali Chemie Pharma Gmbh | 1,7-anellierte 2-(piperazinoalkyl)indol-derivate sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindugnen enthaltende arzneimittel |
| GB9203790D0 (en) * | 1992-02-21 | 1992-04-08 | Merck Sharp & Dohme | Therapeutic agents |
| US5360802A (en) * | 1992-05-11 | 1994-11-01 | Merck Sharpe & Dohme Ltd. | Benzodiazepine derivatives, compositions containing them and their use in therapy |
| DE4304806A1 (de) * | 1993-02-17 | 1994-08-18 | Kali Chemie Pharma Gmbh | 5-Phenyl-pyrrolo-1,4-benzoxazin- und -thiazin-Derivate sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5556969A (en) * | 1994-12-07 | 1996-09-17 | Merck Sharp & Dohme Ltd. | Benzodiazepine derivatives |
| NZ314105A (en) * | 1996-02-02 | 1997-12-19 | Sumitomo Pharma | Guanidine derivative substituted with a substituted indole which is peri condensed with a heterocyclic ring |
| CN1572299A (zh) * | 1998-09-30 | 2005-02-02 | 武田药品工业株式会社 | 改善膀胱排泄能力的药物 |
| IL159105A0 (en) * | 2001-06-07 | 2004-05-12 | Neuro3D | Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses thereof |
| DE60324449D1 (de) * | 2002-10-30 | 2008-12-11 | Via Pharmaceuticals Inc | Inhibitoren der phosphodiesterase der zyklischen n, und deren verwendung in therapie |
| FR2846653B1 (fr) * | 2002-10-30 | 2007-04-20 | Neuro3D | Inhibiteurs des phosphodiesterases des nucleotides cycliques, preparation et utilisations |
| WO2014098000A1 (en) * | 2012-12-17 | 2014-06-26 | Daiichi Sankyo Company, Limited | Process for preparation of a tricyclic heterocycle |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE34392T1 (de) * | 1983-10-17 | 1988-06-15 | Synthelabo | Imidazolinderivate, ihre herstellung und therapeutische verwendung. |
| CA1332410C (en) * | 1984-06-26 | 1994-10-11 | Roger M. Freidinger | Benzodiazepine analogs |
| US4820834A (en) * | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| FR2567126B1 (fr) * | 1984-07-06 | 1986-12-12 | Synthelabo | Derives de pyrrolo(1,2,3-de) benzoxazine et benzothiazine, leur preparation et leur application en therapeutique |
| US4628084A (en) * | 1986-01-02 | 1986-12-09 | Merck & Co., Inc. | Process for 3-acylamino benzodiazepines |
| EP0322016A1 (en) * | 1987-12-10 | 1989-06-28 | Duphar International Research B.V | 1,7-Annelated indolecarboxylic acid esters and -amides |
| FR2630440B1 (fr) * | 1988-04-25 | 1991-09-20 | Jouveinal Sa | Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique |
| IL91361A (en) * | 1988-09-09 | 1994-10-07 | Fujisawa Pharmaceutical Co | Benzodiazepinone compounds [4,1] connected via positions 1 and 9 and carrying two transducers, processes for their preparation and pharmaceutical preparations containing them |
| FR2652352A1 (fr) * | 1989-09-28 | 1991-03-29 | Jouveinal Sa | Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique. |
-
1990
- 1990-02-14 PH PH40052A patent/PH26955A/en unknown
- 1990-02-14 IL IL9340190A patent/IL93401A/en not_active IP Right Cessation
- 1990-03-01 EP EP90103990A patent/EP0387618B1/de not_active Expired - Lifetime
- 1990-03-01 ES ES90103990T patent/ES2057216T3/es not_active Expired - Lifetime
- 1990-03-01 DE DE59006544T patent/DE59006544D1/de not_active Expired - Fee Related
- 1990-03-01 AT AT90103990T patent/ATE109146T1/de not_active IP Right Cessation
- 1990-03-01 DK DK90103990.9T patent/DK0387618T3/da active
- 1990-03-05 NZ NZ232774A patent/NZ232774A/en unknown
- 1990-03-05 CN CN90101141A patent/CN1032208C/zh not_active Expired - Fee Related
- 1990-03-07 AU AU50753/90A patent/AU616835B2/en not_active Ceased
- 1990-03-07 NO NO901083A patent/NO173869C/no unknown
- 1990-03-07 PT PT93360A patent/PT93360B/pt not_active IP Right Cessation
- 1990-03-07 KR KR1019900003005A patent/KR920003627B1/ko not_active IP Right Cessation
- 1990-03-07 FI FI901154A patent/FI92486C/fi not_active IP Right Cessation
- 1990-03-07 US US07/489,502 patent/US5010076A/en not_active Expired - Lifetime
- 1990-03-07 HU HU901333A patent/HU207317B/hu not_active IP Right Cessation
- 1990-03-07 IE IE81390A patent/IE65030B1/en not_active IP Right Cessation
- 1990-03-08 JP JP2055191A patent/JP3010558B2/ja not_active Expired - Fee Related
-
1991
- 1991-12-19 CS CS913900A patent/CS390091A3/cs unknown
-
1994
- 1994-09-30 HU HU94P/P00034P patent/HU210354A9/hu unknown
-
1998
- 1998-06-17 HK HK98105568A patent/HK1006570A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE65030B1 (en) | 1995-10-04 |
| NZ232774A (en) | 1991-04-26 |
| HU210354A9 (en) | 1995-03-28 |
| DE59006544D1 (de) | 1994-09-01 |
| FI92486C (fi) | 1994-11-25 |
| EP0387618B1 (de) | 1994-07-27 |
| PT93360A (pt) | 1990-11-07 |
| ES2057216T3 (es) | 1994-10-16 |
| NO173869B (no) | 1993-11-08 |
| IL93401A (en) | 1994-08-26 |
| JPH02273678A (ja) | 1990-11-08 |
| AU616835B2 (en) | 1991-11-07 |
| IL93401A0 (en) | 1990-11-29 |
| CN1045392A (zh) | 1990-09-19 |
| DK0387618T3 (da) | 1994-08-22 |
| JP3010558B2 (ja) | 2000-02-21 |
| HU207317B (en) | 1993-03-29 |
| NO173869C (no) | 1994-02-16 |
| FI901154A0 (fi) | 1990-03-07 |
| HUT53641A (en) | 1990-11-28 |
| HU901333D0 (en) | 1990-05-28 |
| EP0387618A1 (de) | 1990-09-19 |
| AU5075390A (en) | 1990-09-13 |
| ATE109146T1 (de) | 1994-08-15 |
| CS390091A3 (en) | 1992-06-17 |
| KR920003627B1 (ko) | 1992-05-04 |
| NO901083D0 (no) | 1990-03-07 |
| CN1032208C (zh) | 1996-07-03 |
| PT93360B (pt) | 1996-02-29 |
| FI92486B (fi) | 1994-08-15 |
| NO901083L (no) | 1990-09-10 |
| HK1006570A1 (en) | 1999-03-05 |
| US5010076A (en) | 1991-04-23 |
| KR900014391A (ko) | 1990-10-23 |
| IE900813L (en) | 1990-09-08 |
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