KR830005187A - 아미노사이클로펜탄 알케노산 및 에스테르의 제조방법 - Google Patents
아미노사이클로펜탄 알케노산 및 에스테르의 제조방법 Download PDFInfo
- Publication number
- KR830005187A KR830005187A KR1019810001478A KR810001478A KR830005187A KR 830005187 A KR830005187 A KR 830005187A KR 1019810001478 A KR1019810001478 A KR 1019810001478A KR 810001478 A KR810001478 A KR 810001478A KR 830005187 A KR830005187 A KR 830005187A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- phenyl
- optionally substituted
- alkoxy
- halogen
- Prior art date
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- 239000002253 acid Substances 0.000 title claims 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 238000005341 cation exchange Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- A—HUMAN NECESSITIES
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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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- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
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- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
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- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
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- C07D267/02—Seven-membered rings
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
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- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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Abstract
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Claims (1)
- 다음 일반식(2)의 화합물을 산화시키거나 R3가 알킬 또는 아르알킬인 화합물을 제조하기 위하여는 R3가 수소원자인 상응하는 화합물을 에스테르화하거나 X가 아세틸렌기인 상응하는 화합물을 환원시키거나 염을 제조하기 위해서는 일반식(Ⅰ)의 화합물을 산(R3가 수소원자임) 또는 염기로 처리하거나 양이온교환에 의해 염을 다른 화합물로 전환시켜서 다음 일반식(1)의 화합물 및 그의 생리학적으로 무독한 염 및 그의 용매화합물을 제조하는 방법.상기식에서X는 시스 또는 트란스 -CH=CH-이며R1은 말단치환체로서 -COOR3(R3는 수소원자 C1-6알킬 또는 C|7-10아르알킬이다)를 가지는 직쇄 또는 측쇄 C1-7알킬이며Y는 5내지 8원환의 포화된 복소환 아미노기이며(a) 임의로 환중에 -O-, -S-, -SO2-, -NR4(R4는 수소, C1-7알킬 또는 C1-4알킬부위를 가지는 아르알킬이다)를 함유하며/또는(b) 하나 또는 2이상의 C1-4알킬기로 임의로 치환된다. R2는 (i) C2-4알카노일(ii) 페닐(페닐은 C1-4알킬, C1-4알콕시, 할로겐, C5-7사이클로알킬 또는 페닐 C1-4알킬로 임의로 치환된다), 페닐(C1-4알킬, C1-4알콕시 또는 할로겐으로 임의로 치환된다), 또는 나프틸에 의해 임의로 치환된 C3-6알케닐,(iii) C1-12알킬,(iv) (a) 페닐[할로겐, 하이드록시, C1-6알킬, C1-6알콕시, C1-4하이드록시알콕시, 트리플루오로메틸, 시아노, 아릴옥시(예 : 페녹시), C5-7사이클로알킬, 아르알콕시(예 : 벤질옥시), 디메틸아미노메틸, 카복스아미도(-CONH2)5, 티오카복스아미도(-CSNH2) C1-4알카노일, -NR5R6(이때 R5는 및 R6는 같거나 다르며 각각은 수소 또는 C1-4알킬이거나 -NR5R6가 위에서 Y에 대해 정의한 바와 같은 포화된 복소환 아미노기이다), C1-3알킬티오, C1-3알킬설피닐, C1-3알킬부를 가지는 페닐알킬, 아미노설포닐, C1-3알카노일아미노설포닐, 페닐설포닐, 페닐설포닐(페닐부는 C1-3알킬 또는 C1-3알콕시에 의해 임의로 치환된다), 니트로 또는 티에닐에 의해 임의로 치환됨).(b) 티에닐 또는 푸라닐[티에닐 및 푸라닐기는 C1-6알킬, C1-6알콕시, 아릴(예 : 페닐) 또는 페닐(C1-3)알킬 또는 페닐(C1-3)알콕시(아릴 또는 페닐기는 각 경우 C1-3알킬, C1-3알콕시 또는 할로겐으로 임의 치환된다) 아릴옥시(예 : 펜옥시), C5-7사이클로알킬, 할로겐, 니트로 또는 티에닐에 의해 임의로 치환된다](c) 비페닐(페닐 또는 하나 또는 두개의 C1-4알킬알콕시 또는 할로겐 치환체에 의해 임의로 치환된다) 또는 (d) 나프틸(C1-4알킬, C1-4알콕시 또는 할로겐에 의해 임의로 치환된다)에 의해 치환된 C1-5알킬이며 R10는 -COOR3로 치환된 직쇄 또는 측쇄알킬기, -CH2OH 또는 -CHO이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8014256 | 1980-04-30 | ||
| GB8014256 | 1980-04-30 | ||
| GB8100326 | 1981-01-07 | ||
| GB8100326 | 1981-01-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830005187A true KR830005187A (ko) | 1983-08-03 |
| KR850000214B1 KR850000214B1 (ko) | 1985-03-06 |
Family
ID=26275368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810001478A KR850000214B1 (ko) | 1980-04-30 | 1981-04-29 | 아미노사이클로펜탄 알케노산 및 에스테르의 제조방법 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4342756A (ko) |
| JP (2) | JPS5718671A (ko) |
| KR (1) | KR850000214B1 (ko) |
| AT (1) | ATA191781A (ko) |
| AU (1) | AU540147B2 (ko) |
| BE (1) | BE888645A (ko) |
| CH (1) | CH646965A5 (ko) |
| DE (1) | DE3117087A1 (ko) |
| DK (1) | DK189881A (ko) |
| ES (2) | ES8207498A1 (ko) |
| FI (1) | FI78293C (ko) |
| FR (1) | FR2481703B1 (ko) |
| GB (1) | GB2075503B (ko) |
| IE (1) | IE51241B1 (ko) |
| IL (1) | IL62734A (ko) |
| IT (1) | IT1170929B (ko) |
| NL (1) | NL8102116A (ko) |
| NO (1) | NO811470L (ko) |
| NZ (1) | NZ196966A (ko) |
| PT (1) | PT72951B (ko) |
| SE (1) | SE8102731L (ko) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1117403B (it) * | 1978-07-11 | 1986-02-17 | Glaxo Group Ltd | Composti prostanoidi e procedimento per produrli |
| ZA81114B (en) | 1980-01-09 | 1982-01-27 | Glaxo Group Ltd | Prostanoid compounds and their preparation and pharmaceutical formalation |
| US4438111A (en) | 1980-01-09 | 1984-03-20 | Glaxo Group Limited | Prostanoid compounds and pharmaceutical formulations |
| CA1191134A (en) * | 1981-04-29 | 1985-07-30 | Eric W. Collington | Aminocyclopentanol acids and esters and their preparation and pharmaceutical formulation |
| CA1190926A (en) * | 1981-09-16 | 1985-07-23 | Christopher J. Wallis | Aminocyclopentane esters and their preparation and pharmaceutical formulation |
| US4410521A (en) * | 1981-09-16 | 1983-10-18 | Glaxo Group Limited | Aminocyclopentane esters and pharmaceutical formulations |
| IL67041A (en) * | 1981-10-29 | 1988-03-31 | Glaxo Group Ltd | 2-aminocyclopentane alkanoic and alkenoic acid esters,process for their preparation and pharmaceutical compositions containing them |
| GR77727B (ko) * | 1981-10-29 | 1984-09-25 | Glaxo Group Ltd | |
| US4837234A (en) * | 1981-12-23 | 1989-06-06 | National Research Development Corporation | Prostaglandins |
| EP0082646B1 (en) * | 1981-12-23 | 1989-11-15 | National Research Development Corporation | Prostaglandins |
| AU576476B2 (en) * | 1982-09-16 | 1988-09-01 | Glaxo Group Limited | Piperidinylcyclopentanol heptenoic acid salt |
| GB2127406B (en) * | 1982-09-16 | 1986-03-05 | Glaxo Group Ltd | Piperidinlycyclopentanolheptenoic acid salt |
| CA1191136A (en) * | 1982-10-28 | 1985-07-30 | Ian Waterhouse | Preparation of aminocyclopentane acids |
| GB8307099D0 (en) * | 1983-03-15 | 1983-04-20 | Glaxo Group Ltd | Carbocyclic compounds |
| CH662350A5 (fr) * | 1983-09-06 | 1987-09-30 | Glaxo Group Ltd | Aminocyclopentanes, leur preparation et compositions pharmaceutiques les contenant. |
| GB2167404A (en) * | 1984-10-26 | 1986-05-29 | Glaxo Group Ltd | Prostanoid aminocyclopentane alkenoic acids and esters, their preparation and pharmaceutical formulation |
| GB8601985D0 (en) * | 1986-01-28 | 1986-03-05 | Glaxo Group Ltd | Chemical process |
| GB8625326D0 (en) * | 1986-10-22 | 1986-11-26 | Glaxo Group Ltd | Medicaments |
| GB8715333D0 (en) * | 1987-06-30 | 1987-08-05 | Glaxo Group Ltd | Process |
| GB9720270D0 (en) * | 1997-09-25 | 1997-11-26 | Pharmagene Lab Limited | Medicaments for the treatment of migraine |
| GB2330307A (en) * | 1998-02-07 | 1999-04-21 | Glaxo Group Ltd | EP4 Receptor antagonists as bone resorption inhibitors |
| US6414006B1 (en) | 1998-10-15 | 2002-07-02 | Merck Frosst Canada & Co. | Methods for inhibiting bone resorption |
| ES2274378T3 (es) | 1999-08-10 | 2007-05-16 | Glaxo Group Limited | Ligando del receptor ep4 y uso contra dolor neuropatico, cancer de colon,hiv y migraña. |
| GB0124124D0 (en) * | 2001-10-08 | 2001-11-28 | Medical Res Council | Methods of treatment |
| GB0208785D0 (en) * | 2002-04-17 | 2002-05-29 | Medical Res Council | Treatment methtods |
| US20060166872A1 (en) * | 2002-04-17 | 2006-07-27 | Jabbour Henry N | Fp receptor antagonists or pgf2 alpha antagonists for treating menorrhagia |
| US20060171945A1 (en) * | 2003-02-14 | 2006-08-03 | Critchley Hilary Octavia D | Ip receptor antagonists for the treatment of pathological uterine conditions |
| WO2007017670A1 (en) | 2005-08-08 | 2007-02-15 | Argenta Discovery Ltd. | Bicyclo[2.2.]hept-7-ylamine derivatives and their uses |
| JP2008193940A (ja) * | 2007-02-13 | 2008-08-28 | Honda Motor Co Ltd | ポリヒドロキシ酪酸精製方法 |
| EP2951149B1 (en) | 2013-01-30 | 2018-10-10 | Ecolab USA Inc. | Hydrogen sulfide scavengers |
| US10308886B2 (en) | 2015-04-22 | 2019-06-04 | Ecolab Usa Inc. | Development of a novel high temperature stable scavenger for removal of hydrogen sulfide |
| US10584286B2 (en) | 2015-09-08 | 2020-03-10 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
| CN107949625B (zh) | 2015-09-08 | 2020-10-02 | 艺康美国股份有限公司 | 作为硫化氢清除剂的烃溶性/分散性半缩甲醛 |
| BR112019000714B1 (pt) | 2016-07-29 | 2022-05-31 | Ecolab Usa Inc | Composição, e, método |
| WO2019014415A1 (en) | 2017-07-13 | 2019-01-17 | Ecolab USA, Inc. | METHOD FOR REMOVING A COMPOUND CONTAINING SULFUR BY ADDITION OF A COMPOSITION |
| CA3127439A1 (en) | 2019-01-23 | 2020-07-30 | Championx Usa Inc. | Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a michael acceptor |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1553293A (en) | 1976-02-23 | 1979-09-26 | Lepetit Spa | Azaprostaglandins |
| US4189606A (en) * | 1976-02-23 | 1980-02-19 | Gruppo Lepetit S.P.A. | 13-Azaprostaglandins |
| GB2028805B (en) * | 1978-07-11 | 1982-11-03 | Glaxo Group Ltd | Prostanoid compounds |
| IT1117403B (it) * | 1978-07-11 | 1986-02-17 | Glaxo Group Ltd | Composti prostanoidi e procedimento per produrli |
| US4239778A (en) * | 1978-09-12 | 1980-12-16 | The University Of Illinois Foundation | Azaprostanoic acid analogs and their use as inhibitors of platelet aggregation |
-
1981
- 1981-04-28 JP JP6353781A patent/JPS5718671A/ja active Granted
- 1981-04-28 IL IL62734A patent/IL62734A/xx unknown
- 1981-04-29 ES ES501740A patent/ES8207498A1/es not_active Expired
- 1981-04-29 NZ NZ196966A patent/NZ196966A/en unknown
- 1981-04-29 FI FI811350A patent/FI78293C/fi not_active IP Right Cessation
- 1981-04-29 IT IT48367/81A patent/IT1170929B/it active
- 1981-04-29 GB GB8113239A patent/GB2075503B/en not_active Expired
- 1981-04-29 DK DK189881A patent/DK189881A/da not_active Application Discontinuation
- 1981-04-29 KR KR1019810001478A patent/KR850000214B1/ko active IP Right Grant
- 1981-04-29 NL NL8102116A patent/NL8102116A/nl not_active Application Discontinuation
- 1981-04-29 SE SE8102731A patent/SE8102731L/xx not_active Application Discontinuation
- 1981-04-29 AT AT0191781A patent/ATA191781A/de not_active IP Right Cessation
- 1981-04-29 DE DE19813117087 patent/DE3117087A1/de active Granted
- 1981-04-29 AU AU69957/81A patent/AU540147B2/en not_active Ceased
- 1981-04-29 CH CH280181A patent/CH646965A5/de not_active IP Right Cessation
- 1981-04-29 PT PT72951A patent/PT72951B/pt unknown
- 1981-04-29 NO NO811470A patent/NO811470L/no unknown
- 1981-04-29 US US06/258,721 patent/US4342756A/en not_active Expired - Fee Related
- 1981-04-29 IE IE957/81A patent/IE51241B1/en unknown
- 1981-04-29 US US06/258,737 patent/US4327092A/en not_active Expired - Fee Related
- 1981-04-30 BE BE0/204664A patent/BE888645A/fr not_active IP Right Cessation
- 1981-04-30 FR FR8108660A patent/FR2481703B1/fr not_active Expired
-
1982
- 1982-03-26 ES ES510838A patent/ES510838A0/es active Granted
- 1982-10-29 JP JP57190702A patent/JPS5882723A/ja active Granted
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