CS114291A3 - Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them - Google Patents

Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them Download PDF

Info

Publication number: CS114291A3
Authority: CS; Czechoslovakia
Prior art keywords: formula; compound; dione; general formula; benzothieno
Prior art date: 1990-04-24

Application number

CS911142A

Other languages

Czech (cs)

English (en)

Inventor

Anker Steen Jorgensen

Carsten Enggaard Stidsen

Peter Faarup

Frederik Christian Gronvald

Flemming Elmelund Nielsen

Original Assignee

Novo Nordisk As

Priority date (The priority date 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 date listed.)

1990-04-24

Filing date

1991-04-22

Publication date

1992-01-15

1991-04-22 Application filed by Novo Nordisk As filed Critical Novo Nordisk As

1992-01-15 Publication of CS114291A3 publication Critical patent/CS114291A3/cs

Links

238000000034 method Methods 0.000 title claims description 66
238000002360 preparation method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 5
241000551547 Dione <red algae> Species 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 87
210000003169 central nervous system Anatomy 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 8
GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
230000002829 reductive effect Effects 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 5
229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
239000001119 stannous chloride Substances 0.000 claims description 5
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XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
229910052979 sodium sulfide Inorganic materials 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
NLSNNKYMIMMKII-UHFFFAOYSA-N 2-cyanobenzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1C#N NLSNNKYMIMMKII-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
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SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
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229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract description 20
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102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 abstract description 7
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 abstract description 7
JZFCFMFLPKVLRY-UHFFFAOYSA-N 1,4-dihydro-[1]benzothiolo[2,3-b]pyrazine-2,3-dione Chemical class S1C2=CC=CC=C2C2=C1NC(=O)C(=O)N2 JZFCFMFLPKVLRY-UHFFFAOYSA-N 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 28
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
238000005160 1H NMR spectroscopy Methods 0.000 description 21
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 14
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
239000005457 ice water Substances 0.000 description 13
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
238000007046 ethoxylation reaction Methods 0.000 description 10
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238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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238000004458 analytical method Methods 0.000 description 8
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235000019341 magnesium sulphate Nutrition 0.000 description 8
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239000000725 suspension Substances 0.000 description 8
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239000004480 active ingredient Substances 0.000 description 6
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239000002552 dosage form Substances 0.000 description 5
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FCTXEFOUDMXDPD-UHFFFAOYSA-N 3-sulfanylpropanenitrile Chemical compound SCCC#N FCTXEFOUDMXDPD-UHFFFAOYSA-N 0.000 description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
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210000004027 cell Anatomy 0.000 description 4
230000000694 effects Effects 0.000 description 4
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
HCKUBNLZMKAEIN-UHFFFAOYSA-N 3-amino-1-hydroxypyrrolidin-2-one Chemical compound NC1CCN(O)C1=O HCKUBNLZMKAEIN-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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125000000623 heterocyclic group Chemical group 0.000 description 3
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
OHDYZVVLNPXKDX-UHFFFAOYSA-N 2,3-dichlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1Cl OHDYZVVLNPXKDX-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
HOYWWXGKNSWEBS-UHFFFAOYSA-N 3-bromo-5-chloro-2-nitro-1-benzothiophene Chemical compound C1=C(Cl)C=C2C(Br)=C([N+](=O)[O-])SC2=C1 HOYWWXGKNSWEBS-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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PXASFQGNVIBHDO-UHFFFAOYSA-N 5-fluoro-2-nitro-1-benzothiophen-3-amine Chemical compound C1=C(F)C=C2C(N)=C([N+]([O-])=O)SC2=C1 PXASFQGNVIBHDO-UHFFFAOYSA-N 0.000 description 2
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TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
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BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
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ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/20—Hypnotics; Sedatives

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)

CS911142A 1990-04-24 1991-04-22 Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them CS114291A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK101290A DK101290D0 (da)	1990-04-24	1990-04-24	Heterocykliske forbindelser, deres fremstilling og anvendelse

Publications (1)

Publication Number	Publication Date
CS114291A3 true CS114291A3 (en)	1992-01-15

Family

ID=8100008

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911142A CS114291A3 (en)	1990-04-24	1991-04-22	Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them

Country Status (19)

Country	Link
US (1)	US5182279A (de)
EP (1)	EP0526588B1 (de)
JP (1)	JPH05507468A (de)
AT (1)	ATE102626T1 (de)
AU (1)	AU640230B2 (de)
CA (1)	CA2081201A1 (de)
CS (1)	CS114291A3 (de)
DE (1)	DE69101378T2 (de)
DK (2)	DK101290D0 (de)
ES (1)	ES2062819T3 (de)
FI (1)	FI99014C (de)
HU (1)	HUT67021A (de)
IE (1)	IE73246B1 (de)
IL (1)	IL97913A (de)
NO (1)	NO300776B1 (de)
NZ (1)	NZ237921A (de)
PT (1)	PT97479B (de)
WO (1)	WO1991016325A1 (de)
ZA (1)	ZA913084B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07505908A (ja) *	1992-09-28	1995-06-29	マックセチーニ、マリア　ルイザ	Ｎｍｄａ受容体のアロステリックモジュレーター
FR2696466B1 (fr) *	1992-10-02	1994-11-25	Rhone Poulenc Rorer Sa	Dérivés de 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant.
ATE157977T1 (de)	1992-10-13	1997-09-15	Warner Lambert Co	Chinoxalinderivate als eaa antagonisten
DK12293D0 (da) *	1993-02-02	1993-02-02	Novo Nordisk As	Heterocykliske forbindelser og deres fremstilling og anvendelse
FR2707645B1 (fr) *	1993-07-16	1995-08-11	Rhone Poulenc Rorer Sa	Dérivés d'imidazo[1,2-a]pirazine-4-one, leur préparation et les médicaments les contenant.
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1990
- 1990-04-24 DK DK101290A patent/DK101290D0/da not_active Application Discontinuation
1991
- 1991-04-18 US US07/688,008 patent/US5182279A/en not_active Expired - Fee Related
- 1991-04-22 IL IL9791391A patent/IL97913A/en not_active IP Right Cessation
- 1991-04-22 IE IE132991A patent/IE73246B1/en not_active IP Right Cessation
- 1991-04-22 CS CS911142A patent/CS114291A3/cs unknown
- 1991-04-23 CA CA002081201A patent/CA2081201A1/en not_active Abandoned
- 1991-04-23 AT AT91919028T patent/ATE102626T1/de not_active IP Right Cessation
- 1991-04-23 EP EP91919028A patent/EP0526588B1/de not_active Expired - Lifetime
- 1991-04-23 NZ NZ237921A patent/NZ237921A/en unknown
- 1991-04-23 JP JP91508446A patent/JPH05507468A/ja active Pending
- 1991-04-23 HU HU9203325A patent/HUT67021A/hu unknown
- 1991-04-23 AU AU77736/91A patent/AU640230B2/en not_active Ceased
- 1991-04-23 DE DE69101378T patent/DE69101378T2/de not_active Expired - Fee Related
- 1991-04-23 ES ES91919028T patent/ES2062819T3/es not_active Expired - Lifetime
- 1991-04-23 DK DK91919028.0T patent/DK0526588T3/da active
- 1991-04-23 WO PCT/DK1991/000105 patent/WO1991016325A1/en not_active Ceased
- 1991-04-24 ZA ZA913084A patent/ZA913084B/xx unknown
- 1991-04-24 PT PT97479A patent/PT97479B/pt not_active IP Right Cessation
1992
- 1992-10-23 FI FI924829A patent/FI99014C/fi not_active IP Right Cessation
- 1992-10-23 NO NO924120A patent/NO300776B1/no unknown

Also Published As

Publication number	Publication date
EP0526588B1 (de)	1994-03-09
FI924829A0 (fi)	1992-10-23
AU7773691A (en)	1991-11-11
DK0526588T3 (da)	1994-08-22
ES2062819T3 (es)	1994-12-16
NZ237921A (en)	1993-08-26
US5182279A (en)	1993-01-26
DK101290D0 (da)	1990-04-24
DE69101378D1 (de)	1994-04-14
IL97913A0 (en)	1992-06-21
AU640230B2 (en)	1993-08-19
NO924120L (no)	1992-10-23
WO1991016325A1 (en)	1991-10-31
HUT67021A (en)	1995-01-30
NO300776B1 (no)	1997-07-21
FI99014B (fi)	1997-06-13
IE73246B1 (en)	1997-05-21
NO924120D0 (no)	1992-10-23
PT97479B (pt)	1998-08-31
JPH05507468A (ja)	1993-10-28
FI99014C (fi)	1997-09-25
IE911329A1 (en)	1991-11-06
EP0526588A1 (de)	1993-02-10
CA2081201A1 (en)	1991-10-25
HU9203325D0 (en)	1993-01-28
PT97479A (pt)	1992-01-31
ATE102626T1 (de)	1994-03-15
FI924829L (fi)	1992-10-23
DE69101378T2 (de)	1994-06-16
IL97913A (en)	1995-01-24
ZA913084B (en)	1992-02-26

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