HU218909B - Pirido[2,3-f][1,4]tiazepinek és pirido[3,2-b][1,5]benzotiazepinek, eljárás előállításura, és az ezeket tartalmazó gyógyszerkészítmények - Google Patents
Pirido[2,3-f][1,4]tiazepinek és pirido[3,2-b][1,5]benzotiazepinek, eljárás előállításura, és az ezeket tartalmazó gyógyszerkészítmények Download PDFInfo
- Publication number
- HU218909B HU218909B HU476/91A HU147691A HU218909B HU 218909 B HU218909 B HU 218909B HU 476/91 A HU476/91 A HU 476/91A HU 147691 A HU147691 A HU 147691A HU 218909 B HU218909 B HU 218909B
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- HU
- Hungary
- Prior art keywords
- ethyl
- dioxo
- carboxylate
- thiazepine
- dichlorophenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- JROBKLYZJGATCR-UHFFFAOYSA-N pyrido[2,3-f][1,4]thiazepine Chemical class S1C=CN=CC2=NC=CC=C12 JROBKLYZJGATCR-UHFFFAOYSA-N 0.000 title claims description 5
- BYUYCWQSIZPKCS-UHFFFAOYSA-N pyrido[3,2-b][1,5]benzothiazepine Chemical class C1=NC2=CC=CC=C2SC2=CC=CN=C21 BYUYCWQSIZPKCS-UHFFFAOYSA-N 0.000 title claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 68
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 claims description 9
- UBHDBZKDPMMXQE-UHFFFAOYSA-N 1,1-dioxothiazepin-3-one Chemical class O=C1NS(=O)(=O)C=CC=C1 UBHDBZKDPMMXQE-UHFFFAOYSA-N 0.000 claims description 7
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 208000026723 Urinary tract disease Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- WOBLPDAWNVAVAS-UHFFFAOYSA-N butyl carboxy carbonate Chemical compound CCCCOC(=O)OC(O)=O WOBLPDAWNVAVAS-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- OAOPDYUHWPBJCW-UHFFFAOYSA-N cyanoboron;sodium Chemical compound [Na].[B]C#N OAOPDYUHWPBJCW-UHFFFAOYSA-N 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
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- 238000011067 equilibration Methods 0.000 description 1
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- ABDBTUQWVQRHIR-UHFFFAOYSA-N ethyl 4,7-dimethyl-1,1-dioxo-9-(2,3,4,5,6-pentafluorophenyl)-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(C)CCS2(=O)=O)=C2C1C1=C(F)C(F)=C(F)C(F)=C1F ABDBTUQWVQRHIR-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
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- 210000003205 muscle Anatomy 0.000 description 1
- 230000004703 negative regulation of smooth muscle contraction Effects 0.000 description 1
- 238000011587 new zealand white rabbit Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
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- 238000001356 surgical procedure Methods 0.000 description 1
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- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- GSJJCZSHYJNRPN-UHFFFAOYSA-N tert-butyl n-(2-sulfanylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCS GSJJCZSHYJNRPN-UHFFFAOYSA-N 0.000 description 1
- LFTNGLIVHOVMSS-UHFFFAOYSA-N tert-butyl n-[2-(3-chloro-2-hydroxypropyl)sulfanylethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCSCC(O)CCl LFTNGLIVHOVMSS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
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- 238000001665 trituration Methods 0.000 description 1
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Classifications
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- 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
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
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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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (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)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/518,351 US5075440A (en) | 1990-05-03 | 1990-05-03 | Novel pyrido[2,3-f](1,4)thiazepines and pyrido[3,2-b](1,5)benzothiazepines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU911476D0 HU911476D0 (en) | 1991-11-28 |
| HUT60745A HUT60745A (en) | 1992-10-28 |
| HU218909B true HU218909B (hu) | 2000-12-28 |
Family
ID=24063558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU476/91A HU218909B (hu) | 1990-05-03 | 1991-05-02 | Pirido[2,3-f][1,4]tiazepinek és pirido[3,2-b][1,5]benzotiazepinek, eljárás előállításura, és az ezeket tartalmazó gyógyszerkészítmények |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5075440A (https=) |
| EP (1) | EP0462696B1 (https=) |
| JP (1) | JP3296499B2 (https=) |
| KR (1) | KR100195345B1 (https=) |
| CN (2) | CN1034077C (https=) |
| AT (1) | ATE126231T1 (https=) |
| AU (1) | AU651580B2 (https=) |
| CA (1) | CA2041594C (https=) |
| DE (1) | DE69111915T2 (https=) |
| DK (1) | DK0462696T3 (https=) |
| ES (1) | ES2079570T3 (https=) |
| FI (1) | FI95912C (https=) |
| GR (1) | GR3017305T3 (https=) |
| HK (1) | HK51496A (https=) |
| HU (1) | HU218909B (https=) |
| IE (1) | IE68524B1 (https=) |
| IL (6) | IL127047A0 (https=) |
| MY (1) | MY106552A (https=) |
| NO (1) | NO179411C (https=) |
| NZ (1) | NZ237988A (https=) |
| PT (1) | PT97547B (https=) |
| TN (1) | TNSN91030A1 (https=) |
| TW (1) | TW218878B (https=) |
| ZA (1) | ZA913319B (https=) |
| ZW (1) | ZW5291A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6593335B1 (en) | 1997-12-18 | 2003-07-15 | Abbott Laboratories | Potassium channel openers |
| US6265417B1 (en) | 1997-12-18 | 2001-07-24 | Abbott Laboratories | Potassium channel openers |
| AU756505B2 (en) * | 1997-12-18 | 2003-01-16 | Abbott Laboratories | Potassium channel openers |
| JPH11193289A (ja) * | 1997-12-26 | 1999-07-21 | Suntory Ltd | ピロールスルホンアミド誘導体 |
| US6482854B1 (en) * | 1999-03-25 | 2002-11-19 | Massachusetts Eye And Ear Infirmary | Glaucoma treatment |
| US7015212B1 (en) | 1999-05-12 | 2006-03-21 | The United States Of America As Represented By The Department Of Health And Human Services | Thiazepine inhibitors of HIV-1 integrase |
| HUP0201566A3 (en) * | 1999-06-14 | 2004-03-01 | Ortho Mcneil Pharm Inc | Dithiepino[6,5-b]pyridines, their preparation pharmaceutical compositions containing thereof and an apparatus for their administering |
| ES2246248T3 (es) * | 1999-07-12 | 2006-02-16 | Ortho-Mcneil Pharmaceutical, Inc. | Oxatiepino (6,5-b)dihidropiridinas, y composiciones y metodos relacionados. |
| US6472530B1 (en) | 1999-09-22 | 2002-10-29 | Ortho-Mcneil Pharmaceutical, Inc. | Benzo-fused dithiepino[6,5-b]pyridines, and related compositions and methods |
| CA2396962A1 (en) | 2000-01-12 | 2001-07-19 | Ortho-Mcneil Pharmaceutical, Inc. | Benzosulfones and related compositions and methods |
| AU783503B2 (en) * | 2000-01-27 | 2005-11-03 | Ortho-Mcneil Pharmaceutical, Inc. | Benzoxathiepino(3,4-b)pyridine derivatives, process for their preparation and their use as medicaments |
| JP2003528104A (ja) | 2000-03-23 | 2003-09-24 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | チエピノ［３，２−ｂ］ジヒドロピリジンおよび関連組成物ならびに方法 |
| CN1444587A (zh) | 2000-05-30 | 2003-09-24 | 奥索-麦克尼尔药品公司 | 二氢吡啶软药及相关组合物和方法 |
| KR101233139B1 (ko) | 2011-04-21 | 2013-02-21 | 주식회사 한서켐 | 라세믹 1,4-티아제핀 화합물의 분할 방법 |
| US20160207893A1 (en) * | 2014-12-30 | 2016-07-21 | Myotherix, Inc. | Novel calcium modulators |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1587128A (en) * | 1977-04-07 | 1981-04-01 | Hexachimie | Benzothiazepine derivatives |
| US4285955A (en) * | 1978-10-31 | 1981-08-25 | Bayer Aktiengesellschaft | 1,4-Dihydropyridinecarboxylic acids |
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| FR2511683A1 (fr) * | 1981-08-20 | 1983-02-25 | Hexachimie | Nouveaux derives de la pyrido (2,3-b) benzothiazepine(1,5) substituee en 5 par une carboxypiperazine, leur procede de preparation, leur application en therapeutique |
| EP0225175A3 (en) * | 1985-11-28 | 1988-12-28 | FISONS plc | Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof |
-
1990
- 1990-05-03 US US07/518,351 patent/US5075440A/en not_active Expired - Lifetime
-
1991
- 1991-04-29 IL IL12704798A patent/IL127047A0/xx unknown
- 1991-04-29 IL IL12044691A patent/IL120446A/xx not_active IP Right Cessation
- 1991-04-29 IL IL97999A patent/IL97999A/xx not_active IP Right Cessation
- 1991-04-29 IL IL12704791A patent/IL127047A/xx not_active IP Right Cessation
- 1991-04-29 IL IL12044697A patent/IL120446A0/xx unknown
- 1991-04-29 NZ NZ237988A patent/NZ237988A/xx unknown
- 1991-04-29 IL IL12044797A patent/IL120447A/xx not_active IP Right Cessation
- 1991-05-01 CA CA002041594A patent/CA2041594C/en not_active Expired - Fee Related
- 1991-05-02 FI FI912124A patent/FI95912C/fi active
- 1991-05-02 DE DE69111915T patent/DE69111915T2/de not_active Expired - Fee Related
- 1991-05-02 ZW ZW52/91A patent/ZW5291A1/xx unknown
- 1991-05-02 HU HU476/91A patent/HU218909B/hu not_active IP Right Cessation
- 1991-05-02 EP EP91303970A patent/EP0462696B1/en not_active Expired - Lifetime
- 1991-05-02 ES ES91303970T patent/ES2079570T3/es not_active Expired - Lifetime
- 1991-05-02 PT PT97547A patent/PT97547B/pt not_active IP Right Cessation
- 1991-05-02 DK DK91303970.7T patent/DK0462696T3/da active
- 1991-05-02 ZA ZA913319A patent/ZA913319B/xx unknown
- 1991-05-02 NO NO911723A patent/NO179411C/no unknown
- 1991-05-02 AU AU76354/91A patent/AU651580B2/en not_active Ceased
- 1991-05-02 KR KR1019910007086A patent/KR100195345B1/ko not_active Expired - Fee Related
- 1991-05-02 IE IE148891A patent/IE68524B1/en not_active IP Right Cessation
- 1991-05-02 AT AT91303970T patent/ATE126231T1/de not_active IP Right Cessation
- 1991-05-02 JP JP13047291A patent/JP3296499B2/ja not_active Expired - Fee Related
- 1991-05-02 MY MYPI91000748A patent/MY106552A/en unknown
- 1991-05-03 CN CN91103594A patent/CN1034077C/zh not_active Expired - Fee Related
- 1991-05-03 TN TNTNSN91030A patent/TNSN91030A1/fr unknown
- 1991-07-20 TW TW080105637A patent/TW218878B/zh active
-
1995
- 1995-07-29 CN CN95109346A patent/CN1039416C/zh not_active Expired - Fee Related
- 1995-09-06 GR GR950402432T patent/GR3017305T3/el unknown
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1996
- 1996-03-21 HK HK51496A patent/HK51496A/en not_active IP Right Cessation
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| MM4A | Lapse of definitive patent protection due to non-payment of fees |