LV12047B - Kondensēti pirimidīna atvasinājumi un to lietošana par angiotenzīna ii antagonistiem - Google Patents
Kondensēti pirimidīna atvasinājumi un to lietošana par angiotenzīna ii antagonistiem 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
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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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
-
- 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
-
- 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
- A61P9/14—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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (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)
Claims (15)
- LV 12047 FORMULA 1. Savienojums ar formulu Ikur: R2·, R2, R2 un R4 ir neatkarīgi H, alkilgrupa ar 1 līdz 6 oglekļa atomiem, vai perfluoroalkilgrupa ar 1 līdz 6 oglekļa atomiem; R5 ir H vai, kad n ir 1, R2 kopā ar R2 .ietver dubulto saiti, n ir 0 līdz 1, p ir 0 līdz 2, m ir 0 līdz 3; Ar2· irkur W ir H, alkilgrupa ar 1 līdz 6 oglekļa atomiem, halogēns, hidroksigrupa vai alkoksi atvasinājums ar 1 līdz 6 oglekļa atomiem, Ar2 irkur X ir Οθ£Η, CN, vai 2kur R6 ir H, trešējā butilgrupa, tri-n-butilstannil-, vai trifenilmetilgrupa; vai šo savienojumu farmaceitiski pieņemama sāls; vai šo savienojumu N-oksīds.
- 2. Savienojums saskaņā ar 1. punktu ar formulu IIII kur: Ri, R^, r3 un R^ ir neatkarīgi Hf alkilgrupa ar 1 līdz 6 10 oglekļa atomiem, vai perfluoroalkilgrupa ar 1 līdz 6 oglekļa atomiem; R5 ir H vai, kad n ir 1, R3 kopā ar R3 ietver dubultu saiti; n ir 0 līdz 1, Ar1 ir20x \\ N vai /N kur X ir vai C02H, CN, 25 LV 12047 3kur R® ir H, trešējā butilgrupa, tri-n-butilstannil-, vai trifenilmetilgrupa, vai šo savienojumu farmaceitiski pieņemama sāls.
- 3. Savienojums saskaņā ar 1. vai 2. punktu, kur X ir C0£H, CN, vai
- 4. Savienojums saskaņā ar 3. punktu ar formulu IIIkur: R1, R^, r3 un R4 ir neatkarīgi H, metilgrupa, trifluorometilgrupa; R5 ir H vai, kad n ir 1, R5 kopā ar R3 ietver dubulto saiti, n ir 0 līdz 1; Ar^- irvai šo savienojumu farmaceitiski pieņemama sāls. 4
- 5. Savienojums saskaņā ar 4. punktu, kurš ir 2,4-dimetil-5,6,8-trihidro-8-[ [2 ’ - (lH-tetrazol-5-il)(1,1-bifenil]-4-il]metil]-7H-pirido [2,3-d] pirimidīn-7-ons vai šī savienojuma farmaceitiski pieņemama sāls.
- 6. Savienojums saskaņā ar 4. punktu, kurš ir 2,4-diraetil-5,7-dihidro-7-[[2(lH-tetrazol-5-il)[1,1— bifenil]-4-il]metil]-6H-pirolo [2,3-d] pirimidīn-6-ons vai šī savienojuma farmaceitiski pieņemama sāls, vai 5,7-dihidro-2-metil-7-[[2'-(lH-tetrazol-5-il) [1,1-bifenil]-4-il] metil]-4-(trifluorometil)-6H-pirolo [2,3-d] pirimidīn-6-ons vai šī savienojuma farmaceitiski pieņemama sāls, vai 2-metil-4-trifluorometil-5, 6,8-trihidro-8-[[2'-(lH-tetrazol-5-il)[1,1-bifenil]-4-il]-7H-pirido [2,3-d] pirimidīn-7-ons vai šī savienojuma farmaceitiski pieņemama sāls, vai 2,4-dimetil-5,6,8-trihidro-8-[[6-[2-(lH-tetrazol-5-il)fenil]-3-piridinil]metil]-7H-pirido [2,3-d] pirimidīn-7-ons vai šī savienojuma farmaceitiski pieņemama sāls, vai LV 12047 5 2-metil-4-trifluorometil-5,6,8-trihidra-8-[[6-[2(1H-tetrazol-5-il)fenil]-3-piridinil]metil]-7H-pirido [2,3-d] pirimidīn-7-ons vai šī savienojuma farmaceitiski pieņemama sāls, vai 2.4- dimetil-5,6,8-trihidro-8-[[5- [2-(lH-tetrazol-5-il)fenil]-2- piridinil]metil]-7H-pirido [2,3-d] pirimidxn-7-ons vai šī savienojuma farmaceitiski pieņemama sāls, vai 2,4,6-trimetil-5,6,8-trihidro-8-[[2(lH-tetrazol-5-il) [1,1-bifenil]-4-il]metil]-7H-pirido [2,3-d] pirimidīn-7-ons vai ši savienojuma farmaceitiski pieņemama sāls, vai 2.4- dimetil-8-[[2'-(lH-tetrazol-5-il)[1,1-bifenil]-4-ilļmetil]-7H- pirido [2,3-d] pirimidīn-7-ons vai ši savienojuma farmaceitiski pieņemama sāls.
- 7. Process, lai sagatavotu savienojumu ar formulu II 6 kur: rA, R2, R2 un R4 ir neatkarīgi H, alkilgrupa ar 1 līdz 6 oglekļa atomiem, vai perfluoroalkigrupa ar 1 līdz 6 oglekļa atomiem; R2 ir H vai, kad n ir 1, R2 kopā ar R2 ietver dubulto saiti, n ir 0 līdz 1, p ir 0 līdz 2, m ir 0 līdz 3; Ari -j_r=\W // vai c=vW kur W ir H, alkilgrupa ar 1 līdz 6 oglekļa atomiem, halogēns, hidroksigrupa, vai alkoksi atvasinājums ar 1 līdz 6 oglekļa atomiem, Ar2 irkur X ir CO2H, CN, vaikur R® ir H, tresējā butilgrupa, tri-n-butilstannilgrupa, vai trifenilmetilgrupa; vai šo savienojumu farmaceitiski pieņemama sāls; vai šo savienojumu N-oksīds; kura iegūšana ietver (a) sekojoša pirimidlna kondensāciju LV 12047 7kur: rA, R2, R3, r4 f r5 n un p ir definēti formulā I, Z^- ir 5 aizejošā grupa un R7 ir alkilgrupa, ar sekojošu amīnu: H2N-(CH2)m-Ar1-Ar2 kur: m, Ar^ un Ar2 ir definēti formulā I, vai 0 (b) sekojoša bicikliska savienojumakur: 15 R1, R2, R3, R4 , R5 , n, m, p un Ar1 ir definēti formulā I un Y ir para-bromo vai para-jodo grupa, reakciju ar arilborskābi vai arilstannānu pallādija katalizatora klātbūtnē, vai 20 (c) sekojoša bicikliska savienojuma kondensāciju 8kur: R1, R2, R2, R4 , R5 , n un p ir definēti kā formulā I, ar biaril-savienojumu ar formulu 5 Z1-(CH2)m-Ar1-Ar2 kur: m, Ar^ un Ar2 ir definēti augstāk un Z^- ir aizejošā grupa, 10 vai (d) aizsarggrupas atšķelšanu no savienojuma ar formulu I, kur X irkur: 15 R6 ir trešējā butilgrupa, tri-n- butilstannilgrupa vai trifenilmetilgrupa, radot savienojumu, kur R6 ir ūdeņradis, vai (e) savienojuma ar formulu I, kur X ir -CN, reakciju ar 20 azīda reaģentu, tādejādi radot savienojumu ar formulu I, kur X ir, vai (f) savienojuma ar formulu I sāls iegūšanu reakcijā ar neorganisku vai organisku skābi vai bāzi, vai (g) savienojumu ar formulu I vai tā sāls pārvēršanu par šī savienojuma N-oksIdu peroksidēšanas aģentu iedarbībā.
- 8. Process, lai sagatavotu savienojumu ar formulu I kā definēts punktā 7, kurā X ir CO2H, CN, vaikur R® ir H, trešējā butilgrupa; kas ietver (a) savienojuma ar formulu 1 reakciju C026t1 kur: R1, R2, R3, R4 , R5, nun p ir definēti augstāk, ar sekojošu amīnu (formula 2) 10 HjN—(CHz)m—Ar'Y 1 kur: m un Ar^ ir definēti augstāk, un Y ir para-bromo vai para-jodo grupa, lai iegūtu savienojumu ar formulu 3^Ar'Y kur: 10 R1, R2, R3, R4 , R5, n, m, p, Ar1 un Y ir definēti augstāk, un savienojuma ar formulu 3 reakciju ar arilborskābi ar formulu 4: 3(OH)2 Ar2 4 kur: 15 Ar2 ir definēts augstāk; pallādija katalizatora klātbūtnē, un pēc izvēles, kad ir trešējā butilgrupa, atšķeļot LV 12047 11 aizsarggrupu acidolīzes reakcijā, lai iegūtu savienojumu ar formulu I,I kur: 5 rA, R.2, r3, r4 , r5 , n, m, p, Ar-^- un Ar^ ir definēti augstāk.
- 9. Process saskaņā ar punktu 8, kurā savienojums ar formulu 4 10 b<oh)2 Ar2 4 kur Air12 kur R® ir trešējā butilgrupa; ir sagatavots procesā, kas ietver savienojuma ar formulu 5 apstrādāšanu kur Ar^ ir definēts augstāk, ar Mg un trialkilborātu, B(OR^)3, kur R^ ir alkilgrupa ar 1 līdz 6 oglekļa atomiem, aprotonā šķīdinātājā, lai pēc bāziskās vai skābās apstrādes iegūtu arilborskābi ar formulu 4 10 8(OH)2 Ar2 4 kur Ar^ ir definēts augstāk. 15
- 10. Farmaceitiska kompozīcija, kas satur savienojumu saskaņā ar jebkuru no punktiem 3 līdz 6 un farmaceitiski pieņemamu nesēju.
- 11. Savienojums saskaņā ar jebkuru no punktiem 3 līdz 6 farmaceitiskai lietošanai.
- 12. Savienojums saskaņā ar jebkuru no punktiem 3 līdz 6 hipertensijas vai sirds mazspējas no aizsprostojumiem 25 ārstēšanai.
- 13. Savienojums saskaņā ar jebkuru no punktiem 3 līdz 6 pielietojams aizsardzībai pret restenozi pēc asinsvadu plastiskām operācijām vai tās ārstēšanai zīdītājiem. 30 LV 12047 13
- 14. Savienojums saskaņā ar jebkuru no punktiem 3 līdz 6 medikamentu ražošanai aizsardzībai pret hipertensiju vai sirds mazspēju no aizsprostojumiem vai aizsardzībai pret restenozi pēc asinsvadu plastiskām operācijām vai to ārstēšanai.
- 15. Process saskaņā ar jebkuru no punktiem 7 līdz 9, kur gala produkts ir 2,4,dimetil-5,7-dihidro-7- [[2'-(lH-tetrazol-5-il) [1,1-bifenil]-4-il]metil]-6H-pirolo [2,3-d] pirimidīn-6-ons vai šī savienojuma farmaceitiski pieņemama sāls.
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 (lv) | 1998-08-20 |
Family
ID=27266132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-98-45A LV12047B (lv) | 1991-10-24 | 1998-03-09 | Kondensēti pirimidīna atvasinājumi un to lietošana par angiotenzīna ii antagonistiem |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0539086B1 (lv) |
| JP (1) | JP3240192B2 (lv) |
| KR (1) | KR100286624B1 (lv) |
| CN (2) | CN1039324C (lv) |
| AT (1) | ATE161537T1 (lv) |
| AU (1) | AU653635B2 (lv) |
| CA (1) | CA2080705C (lv) |
| DE (1) | DE69223734T2 (lv) |
| DK (1) | DK0539086T3 (lv) |
| ES (1) | ES2111617T3 (lv) |
| FI (1) | FI103971B1 (lv) |
| GR (1) | GR3025926T3 (lv) |
| HK (1) | HK1003031A1 (lv) |
| HU (2) | HU218786B (lv) |
| IL (1) | IL103436A (lv) |
| LV (1) | LV12047B (lv) |
| NO (1) | NO301275B1 (lv) |
| SG (1) | SG47626A1 (lv) |
| SK (1) | SK280292B6 (lv) |
| TW (1) | TW226375B (lv) |
| UA (1) | UA27748C2 (lv) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993010106A1 (en) * | 1991-11-18 | 1993-05-27 | E.I. Du Pont De Nemours And Company | Tetrazolylphenylboronic acid intermediates for the synthesis of aii receptor antagonists |
| EP0618207B1 (en) * | 1993-03-24 | 1999-01-07 | American Home Products Corporation | Substituted pyridopyrimidines as antihypertensives |
| WO1996009301A1 (fr) * | 1994-09-20 | 1996-03-28 | Wakunaga Seiyaku Kabushiki Kaisha | Procede de production d'un derive de n-biphenylmethylthiadiazoline ou un sel de celui-ci et son intermediaire de production |
| 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 |
| TW200605867A (en) | 2004-03-17 | 2006-02-16 | Novartis Ag | Use of organic compounds |
| KR20130048281A (ko) | 2004-10-08 | 2013-05-09 | 노파르티스 아게 | 확장기 기능장애 또는 확장기 심부전의 예방 또는 치료를 위한 레닌 억제제의 용도 |
| EP1749828A1 (en) | 2005-08-04 | 2007-02-07 | Farmaprojects S.L. | Process for preparing an angiotensin II receptor antagonist |
| EP2481408A3 (en) | 2007-03-01 | 2013-01-09 | Probiodrug AG | New use of glutaminyl cyclase inhibitors |
| EP2865670B1 (en) | 2007-04-18 | 2017-01-11 | Probiodrug AG | Thiourea derivatives as glutaminyl cyclase inhibitors |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | 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 |
| CA3089569C (en) | 2007-06-04 | 2023-12-05 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2008148812A1 (en) * | 2007-06-07 | 2008-12-11 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | 5beta, 14beta-androstane derivatives useful for the treatment of restenosis after angioplastic or endoartherectomy and diseases due to organ fibrosis |
| EP2321341B1 (en) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| US8486940B2 (en) | 2009-09-11 | 2013-07-16 | Probiodrug Ag | Inhibitors |
| JP6026284B2 (ja) | 2010-03-03 | 2016-11-16 | 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 |
| EP2545047B9 (en) | 2010-03-10 | 2015-06-10 | Probiodrug AG | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| EP2560953B1 (en) | 2010-04-21 | 2016-01-06 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| JP6050264B2 (ja) | 2011-03-16 | 2016-12-21 | 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 |
| BR112014014527A2 (pt) | 2011-12-15 | 2017-06-13 | Takeda Pharmaceuticals Usa Inc | combinações de azilsartan e clorotalidona para tratar hipertensão em pacientes negros |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| RS65632B1 (sr) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Ltd | Ultra-prečišćeni agonisti guanilat-ciklaze c, postupak njihove pripreme i upotrebe |
| PL3461819T3 (pl) | 2017-09-29 | 2020-11-30 | Probiodrug Ag | Inhibitory cyklazy glutaminylowej |
Family Cites Families (5)
| 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 |
| JPH05504969A (ja) * | 1990-02-13 | 1993-07-29 | メルク・エンド・カムパニー・インコーポレーテツド | 置換ベンジル要素を含有するアンギオテンシン２アンタゴニスト類 |
| 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/FI103971B1/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 EP EP92309333A patent/EP0539086B1/en not_active Expired - Lifetime
- 1992-10-14 SG SG1996003253A patent/SG47626A1/en unknown
- 1992-10-14 DK DK92309333.0T patent/DK0539086T3/da active
- 1992-10-14 DE DE69223734T patent/DE69223734T2/de not_active Expired - Fee Related
- 1992-10-14 ES ES92309333T patent/ES2111617T3/es not_active Expired - Lifetime
- 1992-10-14 AT AT92309333T patent/ATE161537T1/de not_active IP Right Cessation
- 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 NO NO924121A patent/NO301275B1/no not_active IP Right Cessation
- 1992-10-23 CN CN92113781A patent/CN1039324C/zh not_active Expired - Fee Related
- 1992-10-23 KR KR1019920019580A patent/KR100286624B1/ko not_active IP Right Cessation
- 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/lv unknown
- 1998-03-12 HK HK98102075A patent/HK1003031A1/xx not_active IP Right Cessation
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