DK170302B1 - Substituerede imidazo[1,5-a]pyridinderivater og deres 7,8-dihydro- og 5,6,7,8-tetrahydroderivater samt 5H-5-(4-cyanophenyl)-6,7-dihydropyrrolo[1,2-c]imidazol-derivater og salte deraf, en fremgangsmåde til deres fremstilling, deres anvendelse til fremstilling af farmaceutiske præparater samt farmaceutiske præparater med indhold deraf - Google Patents
Substituerede imidazo[1,5-a]pyridinderivater og deres 7,8-dihydro- og 5,6,7,8-tetrahydroderivater samt 5H-5-(4-cyanophenyl)-6,7-dihydropyrrolo[1,2-c]imidazol-derivater og salte deraf, en fremgangsmåde til deres fremstilling, deres anvendelse til fremstilling af farmaceutiske præparater samt farmaceutiske præparater med indhold deraf Download PDFInfo
- Publication number
- DK170302B1 DK170302B1 DK277685A DK277685A DK170302B1 DK 170302 B1 DK170302 B1 DK 170302B1 DK 277685 A DK277685 A DK 277685A DK 277685 A DK277685 A DK 277685A DK 170302 B1 DK170302 B1 DK 170302B1
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- DK
- Denmark
- Prior art keywords
- formula
- compound
- dihydro
- cyano
- compounds
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 46
- 230000008569 process Effects 0.000 title claims description 20
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical class C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 title claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 title description 5
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 38
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
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- 239000002253 acid Substances 0.000 claims description 25
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical group C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
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- 238000003776 cleavage reaction Methods 0.000 claims description 6
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
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- 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 4
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- ZRBDYBQIBBZJBE-UHFFFAOYSA-N 4-imidazo[1,5-a]pyridin-5-ylbenzonitrile Chemical group C1=CC(C#N)=CC=C1C1=CC=CC2=CN=CN12 ZRBDYBQIBBZJBE-UHFFFAOYSA-N 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 229940125810 compound 20 Drugs 0.000 claims 1
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- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims 1
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C07D471/04—Ortho-condensed systems
-
- 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
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62242184 | 1984-06-20 | ||
US06/622,421 US4617307A (en) | 1984-06-20 | 1984-06-20 | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
Publications (3)
Publication Number | Publication Date |
---|---|
DK277685D0 DK277685D0 (da) | 1985-06-19 |
DK277685A DK277685A (da) | 1985-12-21 |
DK170302B1 true DK170302B1 (da) | 1995-07-31 |
Family
ID=24494112
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK277685A DK170302B1 (da) | 1984-06-20 | 1985-06-19 | Substituerede imidazo[1,5-a]pyridinderivater og deres 7,8-dihydro- og 5,6,7,8-tetrahydroderivater samt 5H-5-(4-cyanophenyl)-6,7-dihydropyrrolo[1,2-c]imidazol-derivater og salte deraf, en fremgangsmåde til deres fremstilling, deres anvendelse til fremstilling af farmaceutiske præparater samt farmaceutiske præparater med indhold deraf |
Country Status (31)
Country | Link |
---|---|
US (1) | US4617307A (ru) |
EP (1) | EP0165904B1 (ru) |
JP (1) | JPS6112688A (ru) |
KR (1) | KR900008566B1 (ru) |
AT (1) | ATE62415T1 (ru) |
AU (1) | AU589565B2 (ru) |
BG (7) | BG60262B1 (ru) |
CA (1) | CA1276633C (ru) |
CS (1) | CS268672B2 (ru) |
CY (1) | CY1750A (ru) |
DD (1) | DD237510A5 (ru) |
DE (1) | DE3582452D1 (ru) |
DK (1) | DK170302B1 (ru) |
DZ (1) | DZ799A1 (ru) |
ES (6) | ES8702406A1 (ru) |
FI (1) | FI80694C (ru) |
GR (1) | GR851487B (ru) |
HK (1) | HK23494A (ru) |
HU (1) | HU202529B (ru) |
IE (1) | IE58070B1 (ru) |
IL (1) | IL75546A (ru) |
MA (1) | MA20459A1 (ru) |
MX (1) | MX9203369A (ru) |
NO (1) | NO162467C (ru) |
NZ (1) | NZ212483A (ru) |
PH (1) | PH23390A (ru) |
PL (6) | PL145087B1 (ru) |
PT (1) | PT80661B (ru) |
RO (1) | RO92583A (ru) |
SU (6) | SU1433413A3 (ru) |
ZA (1) | ZA854615B (ru) |
Families Citing this family (66)
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US5428160A (en) * | 1982-12-21 | 1995-06-27 | Ciba-Geigy Corporation | Substituted imidazo[5-a]pyridine derviatives and other substituted bicyclic derivatives |
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GB8510541D0 (en) * | 1985-04-25 | 1985-05-30 | Wyeth John & Brother Ltd | Heterocyclic compounds |
US5171858A (en) * | 1985-06-05 | 1992-12-15 | Schering A.G. | Preparation of certain 5,6-dihydro-8-phenyl-imidazo[1,5-a]pyridines |
US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
US4749713A (en) * | 1986-03-07 | 1988-06-07 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
IL83163A (en) * | 1986-07-18 | 1991-06-10 | Erba Carlo Spa | Cycloalkyl-substituted 4-pyridyl derivatives,their preparation and pharmaceutical compositions containing them |
GB8820730D0 (en) * | 1988-09-02 | 1988-10-05 | Erba Carlo Spa | Substituted 5 6 7 8-tetrahydroimidazo/1.5-a/pyridines & process for their preparation |
US5057521A (en) * | 1988-10-26 | 1991-10-15 | Ciba-Geigy Corporation | Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism |
US5066656A (en) * | 1989-11-01 | 1991-11-19 | Janssen Pharmaceutica N.V. | Pharmacologically active (6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1H-benzotriazole derivatives |
CA2026792A1 (en) * | 1989-11-01 | 1991-05-02 | Michael N. Greco | (6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives |
MTP1076B (en) * | 1990-01-12 | 1991-09-30 | Ciba Geigy Ag | Hemihydrate |
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CA2066369A1 (en) * | 1991-04-19 | 1992-10-20 | Alex Elbrecht | Control of sex differentiation in fish |
CH683151A5 (de) * | 1991-04-24 | 1994-01-31 | Ciba Geigy Ag | Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus. |
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EP2095819A1 (en) * | 2008-02-28 | 2009-09-02 | Maastricht University | N-benzyl imidazole derivatives and their use as aldosterone synthase inhibitors |
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KR20140093726A (ko) * | 2012-01-17 | 2014-07-28 | 노파르티스 아게 | 디히드로피롤로[1,2-c]이미다졸릴 알도스테론 신타제 또는 아로마타제 억제제의 신규 형태 및 염 |
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JP2016527249A (ja) | 2013-07-25 | 2016-09-08 | ノバルティス アーゲー | 合成アペリンポリペプチドのバイオコンジュゲート |
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Family Cites Families (8)
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JPS5124517B1 (ru) * | 1971-03-15 | 1976-07-24 | ||
FR2449689A1 (fr) * | 1979-02-20 | 1980-09-19 | Logeais Labor Jacques | Nouveaux derives condenses de pyrrolidine ou de piperidine, leur procede de preparation et leurs applications en therapeutique |
FI75569C (fi) * | 1981-06-22 | 1988-07-11 | Ciba Geigy Ag | Analogifoerfarande foer framstaellning av terapeutiskt verkande imidazo/1,5-a/pyridiner. |
US4444775A (en) * | 1981-06-22 | 1984-04-24 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridines |
US4409226A (en) * | 1981-10-05 | 1983-10-11 | Schering Corporation | Imidazo[1,5-a]pyridines |
US4361567A (en) * | 1981-10-05 | 1982-11-30 | Schering Corporation | Treatment of peptic ulcer disease |
US4588732A (en) * | 1982-12-21 | 1986-05-13 | Ciba-Geigy Corporation | Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane synthetase inhibitors |
US4470986A (en) * | 1982-12-21 | 1984-09-11 | Ciba-Geigy Corporation | Certain imidazo (1,5-A) pyridine aliphatic carboxylic acid derivatives and their use as selective thromboxane inhibitors |
-
1984
- 1984-06-20 US US06/622,421 patent/US4617307A/en not_active Expired - Lifetime
-
1985
- 1985-06-17 DE DE8585810279T patent/DE3582452D1/de not_active Expired - Lifetime
- 1985-06-17 FI FI852399A patent/FI80694C/fi not_active IP Right Cessation
- 1985-06-17 AT AT85810279T patent/ATE62415T1/de not_active IP Right Cessation
- 1985-06-17 EP EP85810279A patent/EP0165904B1/de not_active Expired - Lifetime
- 1985-06-18 GR GR851487A patent/GR851487B/el unknown
- 1985-06-18 CS CS854449A patent/CS268672B2/cs not_active IP Right Cessation
- 1985-06-18 CA CA000484263A patent/CA1276633C/en not_active Expired - Lifetime
- 1985-06-18 DZ DZ850130A patent/DZ799A1/fr active
- 1985-06-18 IL IL75546A patent/IL75546A/xx not_active IP Right Cessation
- 1985-06-19 SU SU853917403A patent/SU1433413A3/ru active
- 1985-06-19 IE IE152085A patent/IE58070B1/en not_active IP Right Cessation
- 1985-06-19 PH PH32427A patent/PH23390A/en unknown
- 1985-06-19 BG BG070749A patent/BG60262B1/bg unknown
- 1985-06-19 MA MA20686A patent/MA20459A1/fr unknown
- 1985-06-19 AU AU43857/85A patent/AU589565B2/en not_active Expired
- 1985-06-19 ZA ZA854615A patent/ZA854615B/xx unknown
- 1985-06-19 HU HU852417A patent/HU202529B/hu unknown
- 1985-06-19 KR KR1019850004323A patent/KR900008566B1/ko not_active IP Right Cessation
- 1985-06-19 ES ES544344A patent/ES8702406A1/es not_active Expired
- 1985-06-19 PT PT80661A patent/PT80661B/pt unknown
- 1985-06-19 NO NO852474A patent/NO162467C/no unknown
- 1985-06-19 DK DK277685A patent/DK170302B1/da not_active IP Right Cessation
- 1985-06-19 NZ NZ212483A patent/NZ212483A/xx unknown
- 1985-06-19 RO RO85119210A patent/RO92583A/ro unknown
- 1985-06-20 PL PL1985254099A patent/PL145087B1/pl unknown
- 1985-06-20 PL PL1985259306A patent/PL145104B1/pl unknown
- 1985-06-20 PL PL1985259304A patent/PL145348B1/pl unknown
- 1985-06-20 PL PL1985259305A patent/PL145814B1/pl unknown
- 1985-06-20 PL PL1985259307A patent/PL145105B1/pl unknown
- 1985-06-20 PL PL1985259303A patent/PL145103B1/pl unknown
- 1985-06-20 DD DD85277587A patent/DD237510A5/de not_active IP Right Cessation
- 1985-06-20 JP JP60133167A patent/JPS6112688A/ja active Granted
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1986
- 1986-05-30 ES ES555538A patent/ES8802048A1/es not_active Expired
- 1986-05-30 ES ES555542A patent/ES8802049A1/es not_active Expired
- 1986-05-30 ES ES555541A patent/ES8800681A1/es not_active Expired
- 1986-05-30 ES ES555540A patent/ES8801262A1/es not_active Expired
- 1986-05-30 ES ES555539A patent/ES8802155A1/es not_active Expired
- 1986-07-02 SU SU864027755A patent/SU1436879A3/ru active
- 1986-07-02 SU SU864027756A patent/SU1482530A3/ru active
- 1986-07-02 SU SU864027758A patent/SU1443802A3/ru active
- 1986-07-02 SU SU864027757A patent/SU1436880A3/ru active
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1992
- 1992-06-25 MX MX9203369A patent/MX9203369A/es unknown
- 1992-10-22 BG BG97012A patent/BG60352B2/bg not_active Expired - Lifetime
- 1992-10-22 BG BG97010A patent/BG60306B2/bg unknown
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- 1992-10-22 BG BG97013A patent/BG60353B2/bg unknown
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1993
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B1 | Patent granted (law 1993) | ||
PUP | Patent expired |