IL96879A - 4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing it - Google Patents
4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing itInfo
- Publication number
- IL96879A IL96879A IL9687991A IL9687991A IL96879A IL 96879 A IL96879 A IL 96879A IL 9687991 A IL9687991 A IL 9687991A IL 9687991 A IL9687991 A IL 9687991A IL 96879 A IL96879 A IL 96879A
- Authority
- IL
- Israel
- Prior art keywords
- water
- hemihydrate
- formula
- pyridin
- hydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- AYOZOVVTFYCBNM-UHFFFAOYSA-N 4-(1,2,3,5-tetrahydroimidazo[1,5-a]pyridin-1-yl)benzonitrile hydrochloride Chemical compound Cl.C1(NCN2C1=CC=CC2)C2=CC=C(C#N)C=C2 AYOZOVVTFYCBNM-UHFFFAOYSA-N 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 32
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims abstract description 18
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- 102000014654 Aromatase Human genes 0.000 claims description 3
- 108010078554 Aromatase Proteins 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 238000004279 X-ray Guinier Methods 0.000 claims description 2
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- 102100035863 E3 SUMO-protein ligase ZNF451 Human genes 0.000 claims 1
- 101000782473 Homo sapiens E3 SUMO-protein ligase ZNF451 Proteins 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 5
- 230000008025 crystallization Effects 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
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- 239000004480 active ingredient Substances 0.000 description 15
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- 238000012986 modification Methods 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
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- 239000003125 aqueous solvent Substances 0.000 description 3
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- 239000001828 Gelatine Substances 0.000 description 2
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
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- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RBNOZCGLHXZRLF-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1.C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 RBNOZCGLHXZRLF-UHFFFAOYSA-N 0.000 description 1
- ZVZKQUVPVSHUPY-UHFFFAOYSA-N 4-[1-chloro-4-(1h-imidazol-5-yl)butyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(Cl)CCCC1=CNC=N1 ZVZKQUVPVSHUPY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CCLDINJQFZRBPY-UHFFFAOYSA-N Cl.N1=C(C=CC=C1)C1=CC=CC=C1C#N Chemical compound Cl.N1=C(C=CC=C1)C1=CC=CC=C1C#N CCLDINJQFZRBPY-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
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- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical class C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- CNQDVAWRPXCHEG-UHFFFAOYSA-K trilithium;trichloride Chemical compound [Li+].[Li+].[Li+].[Cl-].[Cl-].[Cl-] CNQDVAWRPXCHEG-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Lubricants (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Liquid Crystal Substances (AREA)
- Pyridine Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH10090 | 1990-01-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96879A0 IL96879A0 (en) | 1992-03-29 |
| IL96879A true IL96879A (en) | 1995-06-29 |
Family
ID=4179261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9687991A IL96879A (en) | 1990-01-12 | 1991-01-04 | 4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing it |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5098911A (pl) |
| EP (1) | EP0437415B1 (pl) |
| JP (1) | JP2694186B2 (pl) |
| KR (1) | KR100191360B1 (pl) |
| CN (1) | CN1037966C (pl) |
| AT (1) | ATE125809T1 (pl) |
| AU (1) | AU638085B2 (pl) |
| BG (2) | BG60033B2 (pl) |
| CA (1) | CA2033937C (pl) |
| CZ (1) | CZ279823B6 (pl) |
| DE (1) | DE59106101D1 (pl) |
| DK (1) | DK0437415T3 (pl) |
| DZ (1) | DZ1482A1 (pl) |
| ES (1) | ES2075399T3 (pl) |
| FI (1) | FI94528C (pl) |
| GR (1) | GR3017027T3 (pl) |
| HU (1) | HU216192B (pl) |
| ID (1) | ID964B (pl) |
| IE (1) | IE67512B1 (pl) |
| IL (1) | IL96879A (pl) |
| MA (1) | MA22040A1 (pl) |
| MT (1) | MTP1076B (pl) |
| NO (1) | NO175747C (pl) |
| NZ (1) | NZ236735A (pl) |
| PH (1) | PH27601A (pl) |
| PL (3) | PL167164B1 (pl) |
| PT (1) | PT96447B (pl) |
| RO (1) | RO107408B1 (pl) |
| RU (2) | RU2021271C1 (pl) |
| SA (1) | SA93140021B1 (pl) |
| TN (1) | TNSN91001A1 (pl) |
| ZA (1) | ZA91229B (pl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW208013B (pl) * | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd | |
| EP0457716A1 (de) * | 1990-04-20 | 1991-11-21 | Ciba-Geigy Ag | Naphthalinderivate |
| TW224461B (pl) * | 1990-09-18 | 1994-06-01 | Ciba Geigy Ag | |
| CH683151A5 (de) * | 1991-04-24 | 1994-01-31 | Ciba Geigy Ag | Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus. |
| JP2914324B2 (ja) | 1995-10-23 | 1999-06-28 | 味の素株式会社 | ピペリジン誘導体の結晶並びにその製造中間体及び製造方法 |
| SE9902550D0 (sv) * | 1999-07-02 | 1999-07-02 | Astra Ab | New crystalline forms |
| WO2012030939A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to individuals with renal impairment |
| ES2704455T3 (es) | 2010-09-01 | 2019-03-18 | Arena Pharm Inc | Formas farmacéuticas de liberación modificada de agonistas de 5-HT2C útiles para la gestión del peso |
| CA2863339C (en) | 2012-01-17 | 2021-03-23 | Novartis Ag | Forms and salts of a dihydropyrrolo[1,2-c]imidazolyl aldosterone synthase or aromatase inhibitor |
| WO2018078049A1 (en) | 2016-10-27 | 2018-05-03 | Damian Pharma Ag | Aldosterone synthase inhibitor |
| BR112019007954A2 (pt) | 2016-10-27 | 2019-07-02 | Damian Pharma Ag | inibidor da aldosterona sintase |
| BR112020022173A2 (pt) | 2018-05-03 | 2021-02-02 | Damian Pharma Ag | r-fadrozol para uso no tratamento de aldostonerismo |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4617307A (en) * | 1984-06-20 | 1986-10-14 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
-
1990
- 1990-12-14 MT MT1076A patent/MTP1076B/xx unknown
-
1991
- 1991-01-02 US US07/636,816 patent/US5098911A/en not_active Expired - Lifetime
- 1991-01-02 PH PH41805A patent/PH27601A/en unknown
- 1991-01-03 EP EP91810003A patent/EP0437415B1/de not_active Expired - Lifetime
- 1991-01-03 AT AT91810003T patent/ATE125809T1/de not_active IP Right Cessation
- 1991-01-03 DK DK91810003.3T patent/DK0437415T3/da active
- 1991-01-03 ES ES91810003T patent/ES2075399T3/es not_active Expired - Lifetime
- 1991-01-03 DE DE59106101T patent/DE59106101D1/de not_active Expired - Lifetime
- 1991-01-04 IL IL9687991A patent/IL96879A/en not_active IP Right Cessation
- 1991-01-07 MA MA22312A patent/MA22040A1/fr unknown
- 1991-01-09 FI FI910126A patent/FI94528C/fi active
- 1991-01-09 DZ DZ910008A patent/DZ1482A1/fr active
- 1991-01-10 PL PL91304084A patent/PL167164B1/pl unknown
- 1991-01-10 PL PL91288653A patent/PL166157B1/pl unknown
- 1991-01-10 CA CA002033937A patent/CA2033937C/en not_active Expired - Lifetime
- 1991-01-10 AU AU69280/91A patent/AU638085B2/en not_active Expired
- 1991-01-10 PT PT96447A patent/PT96447B/pt not_active IP Right Cessation
- 1991-01-10 PL PL91304087A patent/PL166500B1/pl unknown
- 1991-01-10 RO RO146713A patent/RO107408B1/ro unknown
- 1991-01-10 NZ NZ236735A patent/NZ236735A/xx unknown
- 1991-01-10 KR KR1019910000244A patent/KR100191360B1/ko not_active Expired - Lifetime
- 1991-01-11 HU HU4/91A patent/HU216192B/hu unknown
- 1991-01-11 NO NO910137A patent/NO175747C/no not_active IP Right Cessation
- 1991-01-11 TN TNTNSN91001A patent/TNSN91001A1/fr unknown
- 1991-01-11 CN CN91101118A patent/CN1037966C/zh not_active Expired - Lifetime
- 1991-01-11 CZ CS9155A patent/CZ279823B6/cs not_active IP Right Cessation
- 1991-01-11 JP JP3065711A patent/JP2694186B2/ja not_active Expired - Lifetime
- 1991-01-11 RU SU914894233A patent/RU2021271C1/ru active
- 1991-01-11 IE IE10391A patent/IE67512B1/en not_active IP Right Cessation
- 1991-01-11 ZA ZA91229A patent/ZA91229B/xx unknown
- 1991-01-14 BG BG093623A patent/BG60033B2/xx unknown
-
1992
- 1992-01-30 ID IDP190792A patent/ID964B/id unknown
- 1992-04-07 RU SU925011257A patent/RU2088584C1/ru active
- 1992-08-18 BG BG096793A patent/BG61489B2/bg unknown
-
1993
- 1993-06-29 SA SA93140021A patent/SA93140021B1/ar unknown
-
1995
- 1995-08-03 GR GR950401945T patent/GR3017027T3/el unknown
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Legal Events
| Date | Code | Title | Description |
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| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |