LV12047B - CONDENSED PIRIMIDINE DERIVATIVES AND THEIR USE OF ANGIOTENZINE II ANTAGONISTS - Google Patents
CONDENSED PIRIMIDINE DERIVATIVES AND THEIR USE OF ANGIOTENZINE II ANTAGONISTS Download PDFInfo
- Publication number
- LV12047B LV12047B LVP-98-45A LV980045A LV12047B LV 12047 B LV12047 B LV 12047B LV 980045 A LV980045 A LV 980045A LV 12047 B LV12047 B LV 12047B
- Authority
- LV
- Latvia
- Prior art keywords
- formula
- compound
- methyl
- pharmaceutically acceptable
- tetrazol
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 21
- 206010020772 Hypertension Diseases 0.000 claims abstract description 11
- 206010019280 Heart failures Diseases 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 208000037803 restenosis Diseases 0.000 claims abstract description 6
- 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- -1 tri-n-butylnannyl Chemical group 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 11
- 150000001204 N-oxides Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 150000001540 azides Chemical class 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
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- 125000002619 bicyclic group Chemical group 0.000 claims description 2
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- 239000012467 final product Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000003776 cleavage reaction Methods 0.000 claims 2
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- 230000002792 vascular Effects 0.000 claims 2
- XSHXQLODFJYKON-UHFFFAOYSA-N 2,4-dimethyl-8-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=N1)=CC=C1C1=CC=CC=C1C1=NN=NN1 XSHXQLODFJYKON-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
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- 238000005502 peroxidation Methods 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 abstract description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
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- 239000000284 extract Substances 0.000 description 24
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- 239000000243 solution Substances 0.000 description 18
- 238000003818 flash chromatography Methods 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
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- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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- 102000005862 Angiotensin II Human genes 0.000 description 6
- 101800000733 Angiotensin-2 Proteins 0.000 description 6
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 6
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- 229950006323 angiotensin ii Drugs 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000012131 assay buffer Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
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- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 150000003230 pyrimidines Chemical class 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
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- CXVCPPQCXTUFQC-UHFFFAOYSA-N 2,4-dimethyl-6,8-dihydro-5h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(=O)NC2=NC(C)=NC(C)=C21 CXVCPPQCXTUFQC-UHFFFAOYSA-N 0.000 description 3
- YTUQQODSCXAWRW-UHFFFAOYSA-N 2-[5-(chloromethyl)pyridin-2-yl]benzonitrile Chemical compound N1=CC(CCl)=CC=C1C1=CC=CC=C1C#N YTUQQODSCXAWRW-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 150000001499 aryl bromides Chemical class 0.000 description 3
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- AXFFJQDPDFDMGZ-UHFFFAOYSA-N (6-bromopyridin-3-yl)methoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=C(Br)N=C1 AXFFJQDPDFDMGZ-UHFFFAOYSA-N 0.000 description 2
- NSSSVJYQTZRVMH-UHFFFAOYSA-N (6-methylpyridin-3-yl) trifluoromethanesulfonate Chemical compound CC1=CC=C(OS(=O)(=O)C(F)(F)F)C=N1 NSSSVJYQTZRVMH-UHFFFAOYSA-N 0.000 description 2
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- IFABSFWIDIAPQM-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-3-yl] trifluoromethanesulfonate Chemical compound OCC1=CC=C(OS(=O)(=O)C(F)(F)F)C=N1 IFABSFWIDIAPQM-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- 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
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/782,025 US5149699A (en) | 1991-10-24 | 1991-10-24 | Substituted pyridopyrimidines useful as antgiotensin II antagonists |
| GB9207560A GB2265899A (en) | 1992-04-07 | 1992-04-07 | Substituted pyrimidines |
| US07/901,485 US5256654A (en) | 1991-10-24 | 1992-06-25 | Substituted pyrrolopyrimidines, azepinopyrimidines and pyridopyrimidines useful as angiotensin II antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV12047A LV12047A (lv) | 1998-05-20 |
| LV12047B true LV12047B (en) | 1998-08-20 |
Family
ID=27266132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-98-45A LV12047B (en) | 1991-10-24 | 1998-03-09 | CONDENSED PIRIMIDINE DERIVATIVES AND THEIR USE OF ANGIOTENZINE II ANTAGONISTS |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0539086B1 (en:Method) |
| JP (1) | JP3240192B2 (en:Method) |
| KR (1) | KR100286624B1 (en:Method) |
| CN (2) | CN1039324C (en:Method) |
| AT (1) | ATE161537T1 (en:Method) |
| AU (1) | AU653635B2 (en:Method) |
| CA (1) | CA2080705C (en:Method) |
| DE (1) | DE69223734T2 (en:Method) |
| DK (1) | DK0539086T3 (en:Method) |
| ES (1) | ES2111617T3 (en:Method) |
| FI (1) | FI103971B (en:Method) |
| GR (1) | GR3025926T3 (en:Method) |
| HK (1) | HK1003031A1 (en:Method) |
| HU (2) | HU218786B (en:Method) |
| IL (1) | IL103436A (en:Method) |
| LV (1) | LV12047B (en:Method) |
| NO (1) | NO301275B1 (en:Method) |
| SG (1) | SG47626A1 (en:Method) |
| SK (1) | SK280292B6 (en:Method) |
| TW (1) | TW226375B (en:Method) |
| UA (1) | UA27748C2 (en:Method) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69233208T2 (de) * | 1991-11-18 | 2004-07-08 | E.I. Du Pont De Nemours And Co., Wilmington | Tetrazolylphenylborsäureintermediate zur synthese von aii rezeptor antagonisten |
| DE69415706T2 (de) * | 1993-03-24 | 1999-05-20 | American Home Products Corp., Madison, N.J. | Substituierte Pyridopyrimidine als Antihypertensiva |
| DE69507887T2 (de) * | 1994-09-20 | 1999-06-17 | Wakunaga Seiyaku K.K., Osaka | Verfahren zur herstellung von n-biphenylmethylthiadiazolin derivaten oder deren salzen sowie dafür benötigte zwischen verbindungen |
| IT1292437B1 (it) * | 1997-06-30 | 1999-02-08 | Zambon Spa | Processo di orto-metallazione utile per la sintesi di 1 - tetrazol- 5-il) benzeni 2-sostituiti |
| US6638937B2 (en) | 1998-07-06 | 2003-10-28 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| AR033390A1 (es) | 2000-08-22 | 2003-12-17 | Novartis Ag | Una composicion farmaceutica que comprende un antagonista del receptor at1 y un potenciador de la secrecion de insulina, el uso de dicha composicion para la fabricacion de un medicamento y un kit de partes |
| US8168616B1 (en) | 2000-11-17 | 2012-05-01 | Novartis Ag | Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| GB0327839D0 (en) | 2003-12-01 | 2003-12-31 | Novartis Ag | Organic compounds |
| GB0402262D0 (en) | 2004-02-02 | 2004-03-10 | Novartis Ag | Process for the manufacture of organic compounds |
| KR20070006774A (ko) | 2004-03-17 | 2007-01-11 | 노파르티스 아게 | 치료에서 레닌 억제제의 용도 |
| CA2580862A1 (en) | 2004-10-08 | 2006-04-20 | Novartis Ag | Use of renin inhibitors for the prevention or treatment of diastolic dysfunction or diastolic heart failure |
| EP1749828A1 (en) | 2005-08-04 | 2007-02-07 | Farmaprojects S.L. | Process for preparing an angiotensin II receptor antagonist |
| ZA200905537B (en) | 2007-03-01 | 2010-10-27 | Probiodrug Ag | New use of glutaminyl cyclase inhibitors |
| JP5667440B2 (ja) | 2007-04-18 | 2015-02-12 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのチオ尿素誘導体 |
| AU2008261102B2 (en) | 2007-06-04 | 2013-11-28 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8034782B2 (en) | 2008-07-16 | 2011-10-11 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| RS54459B1 (sr) * | 2007-06-07 | 2016-06-30 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Derivati 5beta, 14beta androstana korisni za lečenje bolesti nastalih iz fibroze organa |
| CA2930674A1 (en) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| PL2475428T3 (pl) | 2009-09-11 | 2015-12-31 | Probiodrug Ag | Pochodne heterocykliczne jako inhibitory cyklazy glutaminowej |
| ES2586231T3 (es) | 2010-03-03 | 2016-10-13 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
| EA022420B1 (ru) | 2010-03-10 | 2015-12-30 | Пробиодруг Аг | Гетероциклические ингибиторы глутаминилциклазы (qc, ec 2.3.2.5) |
| JP5945532B2 (ja) | 2010-04-21 | 2016-07-05 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| WO2012123563A1 (en) | 2011-03-16 | 2012-09-20 | Probiodrug Ag | Benz imidazole derivatives as inhibitors of glutaminyl cyclase |
| US20130158080A1 (en) | 2011-12-15 | 2013-06-20 | Takeda Pharmaceuticals U.S.A., Inc. | Methods for treating hypertension in black patients |
| EP2968439A2 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| AU2014235215A1 (en) | 2013-03-15 | 2015-10-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CN113388007A (zh) | 2013-06-05 | 2021-09-14 | 博士医疗爱尔兰有限公司 | 鸟苷酸环化酶c的超纯激动剂、制备和使用所述激动剂的方法 |
| PL3461819T3 (pl) | 2017-09-29 | 2020-11-30 | Probiodrug Ag | Inhibitory cyklazy glutaminylowej |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0407342A3 (en) * | 1989-07-06 | 1991-07-10 | Ciba-Geigy Ag | Pyrimidine derivatives |
| US5100897A (en) * | 1989-08-28 | 1992-03-31 | Merck & Co., Inc. | Substituted pyrimidinones as angiotensin ii antagonists |
| EP0415886A3 (en) * | 1989-08-30 | 1991-10-23 | Ciba-Geigy Ag | Aza compounds |
| WO1991011999A1 (en) * | 1990-02-13 | 1991-08-22 | Merck & Co., Inc. | Angiotensin ii antagonists incorporating a substituted benzyl element |
| IL100917A0 (en) | 1991-02-16 | 1992-11-15 | Fisons Plc | Pyridinone and pyrimidinone derivatives,their preparation and pharmaceutical compositions containing them |
| US5149699A (en) * | 1991-10-24 | 1992-09-22 | American Home Products Corporation | Substituted pyridopyrimidines useful as antgiotensin II antagonists |
-
1992
- 1992-08-27 TW TW081106755A patent/TW226375B/zh active
- 1992-09-30 FI FI924397A patent/FI103971B/fi not_active IP Right Cessation
- 1992-10-01 AU AU26079/92A patent/AU653635B2/en not_active Ceased
- 1992-10-06 HU HU9203161A patent/HU218786B/hu not_active IP Right Cessation
- 1992-10-14 DE DE69223734T patent/DE69223734T2/de not_active Expired - Fee Related
- 1992-10-14 SG SG1996003253A patent/SG47626A1/en unknown
- 1992-10-14 AT AT92309333T patent/ATE161537T1/de not_active IP Right Cessation
- 1992-10-14 ES ES92309333T patent/ES2111617T3/es not_active Expired - Lifetime
- 1992-10-14 EP EP92309333A patent/EP0539086B1/en not_active Expired - Lifetime
- 1992-10-14 DK DK92309333.0T patent/DK0539086T3/da active
- 1992-10-15 IL IL10343692A patent/IL103436A/en not_active IP Right Cessation
- 1992-10-16 CA CA002080705A patent/CA2080705C/en not_active Expired - Fee Related
- 1992-10-23 CN CN92113781A patent/CN1039324C/zh not_active Expired - Fee Related
- 1992-10-23 NO NO924121A patent/NO301275B1/no not_active IP Right Cessation
- 1992-10-23 KR KR1019920019580A patent/KR100286624B1/ko not_active Expired - Fee Related
- 1992-10-23 JP JP28588592A patent/JP3240192B2/ja not_active Expired - Fee Related
- 1992-10-26 SK SK3221-92A patent/SK280292B6/sk unknown
-
1993
- 1993-06-18 UA UA93003129A patent/UA27748C2/uk unknown
-
1995
- 1995-06-29 HU HU95P/P00549P patent/HU211915A9/hu unknown
-
1997
- 1997-05-13 CN CN97111592A patent/CN1175414A/zh active Pending
-
1998
- 1998-01-15 GR GR980400096T patent/GR3025926T3/el unknown
- 1998-03-09 LV LVP-98-45A patent/LV12047B/en unknown
- 1998-03-12 HK HK98102075A patent/HK1003031A1/en not_active IP Right Cessation
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