KR880007497A - 2,3-이치환된 이속사졸리딘, 그의 제조방법, 그를 함유하는 제제 및 그의 용도 - Google Patents
2,3-이치환된 이속사졸리딘, 그의 제조방법, 그를 함유하는 제제 및 그의 용도 Download PDFInfo
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- KR880007497A KR880007497A KR870014373A KR870014373A KR880007497A KR 880007497 A KR880007497 A KR 880007497A KR 870014373 A KR870014373 A KR 870014373A KR 870014373 A KR870014373 A KR 870014373A KR 880007497 A KR880007497 A KR 880007497A
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- -1 2,3-disubstituted isoxazolidine Chemical class 0.000 title claims 11
- 238000000034 method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 229940078467 Prolyl hydroxylase inhibitor Drugs 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 241000534944 Thia Species 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0823—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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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
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- A—HUMAN NECESSITIES
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- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
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- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
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- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
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- C07K5/08—Tripeptides
- C07K5/0819—Tripeptides with the first amino acid being acidic
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Abstract
Description
Claims (12)
- 일반식(I)의 화합물 및 그의 생리학적으로 허용되는 염.상기식에서, A는 a l)각각의 라디칼중 1,2 또는 3개의 수소원자가 카복실, 아미노,(C1-C4)-알킬아미노, 하이드록실, (C1-C4)-알콕시, 할로겐, 디-(C1-C4)-알킬아미노, 카바모일, 설파모일, (C1-C4)-알콕시카보닐, (C6-C12)-아릴 및 (C6-C12)-아릴-(C1-C5)-알킬로 이루어진 그룹으로부터 선택된 1,2 또는 3개의 동일하거나 상이한 라디칼로 임의 치환되거나, 1개의 수소원자가 (C3-C8)-사이클로알킬, (C1-C4)-알킬설포닐, (C1-C4)-알킬설피닐, (C6-C12)-아릴-(C1-C4)-알킬설포닐, (C6-C12)-아릴-(C1-C4)-알킬설피닐, (C6-C12)-아릴옥시, (C3-C9)-헤테로 아릴 및 (C3-C9)-헤테로 아릴옥시로 이루어진 그룹으로 부터 선택된 라디칼에 의해 임의 치환되고 1 또는 2개의 수소원자가 카복실, 아미노, (C1-C4)-알칼아미노, 하이드록실, (C1-C4)-알콕시, 할로겐, 디-(C1-C4)-알킬아미노, 카바모일, 설파모일, (C1-C4)-알콕시카보닐, (C6-C12)-아릴 및 (C6-C12)-아릴-(C1-C5)-알킬로 이루어진 그룹으로부터 선택된 1 또는 2개의 동일하거나 상이한 라디칼에 의해 치환된 (C1-C8)-알킬, (C1-C8)-알카노일, (C1-C8)-알콕시카보닐 또는 (C1-C8)-알킬 설포닐이거나, a 2) (C3-C8)-사이클로알킬, (C6-C12)-아릴, (C6-C12)-아릴설포닐 또는 (C3-C9)-헤테로아릴이거나(여기서, a l) 및 a 2)하에 정의된 라디칼중 (C6-C12)-아릴 또는 (C3-C9)-헤테로아릴은 각각 카복실, 아미노, 니트로, (C1-C4)-알킬아미노, 하이드록실, (C1-C4)-알콕시, 할로겐, 시아노, 디-(C1-C4)-알킬 아미노, 카바모일, 설파모일 및 (C1-C4)-알콕시카보닐로 이루어진 그룹으로부터 선택된 1,2 또는 3개의 동일하거나 상이한 라디칼에 의해 임의 치환된다). 또는 a 3) 일반식(IIa) 또는 (IIb)의 라디칼이며,R1은 b 1) 수소, 또는 b 2) a 1) 또는 a 2)에서 정의한 A와 같고, c 1) R2및 R2'는 동일하거나 상이하며 수소 또는 메틸이고, R3및 R3'는 동일하거나 상이하며 수소: 또는 아미노, 벤질옥시카보닐아미노, 하이드록실, 카복실, 카바모일, 구아니디노, 우레이도, 머캅토, 메틸머캅토, 페닐, 4-클로로페닐, 4-플루오로 페닐, 4-니트로 페닐, 4-메톡시페닐, 4-하이드록시 페닐, 프탈이미도, 4-이미다졸릴, 3-인돌릴, 2-티에닐, 3-티에닐, 2-피리딜, 3-피리딜 또는 사이클로헥실에 의해 임의로 일치환된 (C1-C6)-알킬이거나, c 2) R3및 R3'및/또는 R2'및 R3'각각은 함께 CH2그룹이 산소에 의해 치환될 수 있는 [-CH2-CH2-CH2-]이거나, 또는 c 3) R2및 R3및/또는 R2'및 R3'각각은 함께을 나타내며, B는 카보닐, 티오카보닐, 카비미도일, N-(C1-C3)-알킬-카비미도일, N-(C1-C3)-알콕시-카비미도일, 설피닐, CR5R6또는 직접 결합이고, d 1) R5및 R6는 동일하거나 상이하며, 수소,(C1-C8)-알킬 또는 (C3-C8)-사이클로알킬이거나, 또는 d 2) R5및 R6는 함께 1 또는 2개의 CH2그룹이 산소, 황 및/또는 NR7에 의해 임의로 치환되는 -[CH2]m-(여기에서, m은 4 또는 5이다)이고, D는 이미노, N-메틸이미노, 옥시, 메틸렌 또는 직접 결합을 나타내고, E는 카보닐, C=NR7, C=N-OR7또는 설피닐이거나, F가 결합인 경우 또한 하이드록시메틸렌일 수 있으며, R7은 d l) 에서 정의된 R5와 동일하며, F는 옥시, 이미노, N-메틸이미노 또는 직접 결합을 나타내고, R4는 각각의 알킬이 카복실, 아미노, (C1-C4)-알킬아미노, 하이드록실, (C1-C4)-알콕시, 할로겐, 디(C1-C4)-알킬아미노, 카바모일, (C1-C4)-알콕시카보닐, (C6-C12)-아릴 및 (C6-C12)-아릴-(C1-C5)-알킬로 이루어진 그룹으로부터 선택된 1 또는 2개의 동일하거나 상이한 라디칼에 의해 임의 치환되고, 각각의 (C6-C12)-아릴 또는 (C3-C9)-헤테로아릴이 카복실, 시아노, 아미노, 니트로, (C1-C4)-알킬아미노, 하이드록실, (C1-C4)-알콕시, 할로겐, 디-(C1-C4)-알킬아미노, 카바모일, 설파모일 및 (C1-C4)-알콕시카보닐로 이루어진 그룹으로부터 선택된 1,2 또는 3개의 동일하거나 상이한 라디칼에 의해 임의 치환된 (C1-C6)-알킬, (C3-C6)-사이클로알킬, (C6-C12)-아릴, (C6-C12)-아릴-(C1-C5)-알킬, (C6-C12)-아릴옥시-(C1-C5)-알킬, (C3-C9)-헤테로 아릴-(C1-C5)-알킬이며, R8은 c 1)에서 정의된 R3와 동일하다.
- 제1항에 있어서, A가 임의 치환된 (C1-C8)-알킬, (C1-C8)-알카노일 또는 임의 치환된 (C1-C8)-알콕시카보닐, 또는 제1항에서 a 3)에 정의된 바와 같은 일반식(I)의 화합물.
- 제1항 또는 2항에 있어서, R8가 수소인 일반식(I)의 화합물.
- 제1항 내지 3항중 어느 한 항에 있어서, B가 카보닐, 티오카보닐 또는 CR5R6(여기서 R5및 R8는 H이다)인 일반식(I)의 화합물.
- 제1항 내지 4항중 어느 한 항에 있어서, D가 이미노, 옥시 또는 메틸렌인 일반식(I)의 화합물.
- 제1항 내지 5항중 어느 한 항에 있어서, E카 카보닐인 일반식(I)의 화합물.
- 제1항 내지 6항중 어느 한 항에 있어서, F가 옥시 또는 직접 결합인 일반식(I)의 화합물.
- 제1항 내지 7항중 어느 한 항에 있어서, R4가 임의 치환된 (C6-C12)-아릴, 또는 알킬 잔기가 임의르 치환되고/되거나 아릴 잔기가 임의로 치환된 (C6-C12)-아릴-(C1-C5)-알킬인 일반식(I)의 화합물.
- 반응물들로부터 공지된 방법으로 화합물을 제조하고 경우에 따라서 하나 또는 그 이상의 임시로 도입된 보호그룹(들)을 제거하고, 경우에 따라서 카보닐 그룹을 티아 동족체로 전환시키고, 경우에 따라서 생성된 일반식(I)의 화합물을 그의 생리학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 제1항 내지 8항중 어느 한 항에 따른 일반식(I)의 화합물을 제조하는 방법.
- 제1항 내지 8항중 어느 한 항에 따른 화합물의, 프롤릴 하이드록실라제 저해제로서의 용도.
- 제1항 내지 8항중 어느 한 항에 따른 화합물의, 약제로서의 용도.
- 제1항 내지 8항중 어느 한 항에 따른 화합물 및 생리학적으로 허용되는 비이클을 함유하는 약제학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3643012.9 | 1986-12-17 | ||
DE19863643012 DE3643012A1 (de) | 1986-12-17 | 1986-12-17 | 2,3-disubstituierte isoxazolidine, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
KR880007497A true KR880007497A (ko) | 1988-08-27 |
KR960010349B1 KR960010349B1 (ko) | 1996-07-30 |
Family
ID=6316346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019870014373A KR960010349B1 (ko) | 1986-12-17 | 1987-12-17 | 2, 3-이치환된 이속사졸리딘, 그의 제조방법, 그를 함유하는 제제 및 그의 용도 |
Country Status (21)
Country | Link |
---|---|
US (2) | US5422342A (ko) |
EP (1) | EP0271865B1 (ko) |
JP (1) | JP2703912B2 (ko) |
KR (1) | KR960010349B1 (ko) |
AR (1) | AR246528A1 (ko) |
AT (1) | ATE81344T1 (ko) |
AU (1) | AU599177B2 (ko) |
CA (1) | CA1338484C (ko) |
DE (2) | DE3643012A1 (ko) |
DK (1) | DK171894B1 (ko) |
ES (1) | ES2052539T3 (ko) |
FI (1) | FI88303C (ko) |
GR (1) | GR3006699T3 (ko) |
HU (1) | HU201961B (ko) |
IE (1) | IE61034B1 (ko) |
IL (1) | IL84841A (ko) |
NO (1) | NO175058B (ko) |
NZ (1) | NZ222921A (ko) |
PH (1) | PH24746A (ko) |
PT (1) | PT86380B (ko) |
ZA (1) | ZA879400B (ko) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3818850A1 (de) * | 1988-06-03 | 1989-12-07 | Hoechst Ag | Oligopeptide mit zyklischen prolin-analogen aminosaeuren |
DD284030A5 (de) | 1988-11-24 | 1990-10-31 | Hoechst Ag,De | Verfahren zur herstellung von peptiden mit bradykinin-antagonistischer wirkung |
DE3842197A1 (de) * | 1988-12-15 | 1990-06-21 | Hoechst Ag | Rasch spaltbares substrat fuer die hiv-protease |
DE4016596A1 (de) * | 1990-05-23 | 1991-11-28 | Hoechst Ag | Ein neues kupplungsreagenz fuer die peptidsynthese |
LT3872B (en) | 1993-12-06 | 1996-04-25 | Hoechst Ag | Novel peptides and pharmaceutical compositions containing them |
DE4443892A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | 4-(Chinolin-2-yl-methoxy)-phenyl-essigsäurederivate |
FR2746394B1 (fr) | 1996-03-20 | 1998-05-29 | Roussel Uclaf | Nouveaux composes tricycliques, leur procede de preparation, et les intermediaires de ce procede, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
ATE212990T1 (de) | 1996-03-20 | 2002-02-15 | Hoechst Ag | Inhibitoren der knochenresorption und vitronectinrezeptor-antagonisten |
US5801187A (en) * | 1996-09-25 | 1998-09-01 | Gpi-Nil Holdings, Inc. | Heterocyclic esters and amides |
DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
DE19741235A1 (de) | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
DE19741873A1 (de) * | 1997-09-23 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
DE19751251A1 (de) | 1997-11-19 | 1999-05-20 | Hoechst Marion Roussel De Gmbh | Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate |
DE19821483A1 (de) | 1998-05-14 | 1999-11-18 | Hoechst Marion Roussel De Gmbh | Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
AU2002323368B2 (en) * | 2001-08-23 | 2006-12-07 | The Government Of The United States Of America As Represented By The Secretary, Department Of Health & Human Services | Methods of inhibiting formation of vascular channels and profileration using pyridinone derivatives |
US7842815B2 (en) | 2004-06-17 | 2010-11-30 | Infinity Pharmaceuticals, Inc. | Compounds and methods for inhibiting the interaction of BCL proteins with binding partners |
ATE548359T1 (de) | 2004-06-17 | 2012-03-15 | Infinity Discovery Inc | Verbindungen und verfahren zur inhibierung der wechselwirkung von bcl-proteinen mit bindungspartnern |
TWI389895B (zh) | 2006-08-21 | 2013-03-21 | Infinity Discovery Inc | 抑制bcl蛋白質與結合夥伴間之交互作用的化合物及方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3944562A (en) * | 1974-04-17 | 1976-03-16 | The Upjohn Company | αS, 4S, 5R α-Amino-3-chloro-4-hydroxy-2-isoxazoline-5-acetic acid |
US4269772A (en) * | 1980-01-14 | 1981-05-26 | Merck & Co., Inc. | Synthesis of thienamycin via trans-3-carboxymethylene-4-carboxy-5-methyl-Δ2 -isoxazoline |
DE3002989A1 (de) * | 1980-01-29 | 1981-07-30 | Hoechst Ag, 6000 Frankfurt | Hydroxyphenyl-thiazol, -thiazolin und -thiazolidin-carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des kollagenstoffwechsels |
US4562187A (en) * | 1985-01-22 | 1985-12-31 | Hoechst-Roussel Pharmaceuticals Inc. | (Isoxazol-3-yl)arylmethanones, compositions and pharmaceutical use |
DE3643957A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | Substituierte n-methylisoxazolidine |
-
1986
- 1986-12-17 DE DE19863643012 patent/DE3643012A1/de not_active Withdrawn
-
1987
- 1987-12-15 ES ES87118530T patent/ES2052539T3/es not_active Expired - Lifetime
- 1987-12-15 DE DE87118530T patent/DE3782149D1/de not_active Expired - Fee Related
- 1987-12-15 FI FI875503A patent/FI88303C/fi not_active IP Right Cessation
- 1987-12-15 EP EP87118530A patent/EP0271865B1/de not_active Expired - Lifetime
- 1987-12-15 ZA ZA879400A patent/ZA879400B/xx unknown
- 1987-12-15 NZ NZ222921A patent/NZ222921A/xx unknown
- 1987-12-15 PH PH36227A patent/PH24746A/en unknown
- 1987-12-15 AT AT87118530T patent/ATE81344T1/de not_active IP Right Cessation
- 1987-12-15 AR AR87309602A patent/AR246528A1/es active
- 1987-12-16 DK DK662087A patent/DK171894B1/da not_active IP Right Cessation
- 1987-12-16 IL IL84841A patent/IL84841A/xx not_active IP Right Cessation
- 1987-12-16 PT PT86380A patent/PT86380B/pt not_active IP Right Cessation
- 1987-12-16 AU AU82589/87A patent/AU599177B2/en not_active Ceased
- 1987-12-16 CA CA000554535A patent/CA1338484C/en not_active Expired - Fee Related
- 1987-12-16 NO NO875263A patent/NO175058B/no not_active IP Right Cessation
- 1987-12-16 JP JP62316361A patent/JP2703912B2/ja not_active Expired - Fee Related
- 1987-12-16 IE IE341887A patent/IE61034B1/en not_active IP Right Cessation
- 1987-12-17 HU HU875758A patent/HU201961B/hu not_active IP Right Cessation
- 1987-12-17 KR KR1019870014373A patent/KR960010349B1/ko not_active IP Right Cessation
-
1992
- 1992-12-30 GR GR920402521T patent/GR3006699T3/el unknown
-
1993
- 1993-04-16 US US08/047,074 patent/US5422342A/en not_active Expired - Fee Related
-
1995
- 1995-02-24 US US08/393,814 patent/US5610146A/en not_active Expired - Fee Related
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