PL144948B1 - Method of obtaining novel thienotriazolo-1,4-diazepin-2-carboxylamides - Google Patents
Method of obtaining novel thienotriazolo-1,4-diazepin-2-carboxylamides Download PDFInfo
- Publication number
- PL144948B1 PL144948B1 PL1986257602A PL25760286A PL144948B1 PL 144948 B1 PL144948 B1 PL 144948B1 PL 1986257602 A PL1986257602 A PL 1986257602A PL 25760286 A PL25760286 A PL 25760286A PL 144948 B1 PL144948 B1 PL 144948B1
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- carbon atoms
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (2)
1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych amidów kwasów tienotriazolo-1,4-diazepino-2-karboksy- lowych o wzorze ogólnym 1, w którym Rj oznacza atom wodoru, prosta lub rozgaleziona gru¬ pe alkilowa o 1- 4 atomach wegla, grupe cyklopropylowa, metoksylowa lub atom chloru lub bromu, IU i R*9 które sa jednakowe albo rózne, oznaczaja atom wodoru, prosta lub rozgale¬ ziona grupe alkilowa albo hydroksyalkilowa o 1 - 4 atomach wegla, albo obie grupy Rp i R, razem z atomem azotu oznaczaja 5-, 6- lub 7-czlonowy pierscien, który ewentualnie jako dalszy heteroatom zawiera atom azotu, tlenu lub siarki i przy czym drugi atom azotu jest ewentualnie podstawiony grupa metylowa, R, oznacza grupe fenylowa, przy czym pierscien fenyIowy jest podstawiony atomem chloru lub bromu, zas n oznacza jedna z liczb 0-8, znamienny tym, ze kwas 2-karboksylowy o wzorze ogólnym 2, w którym grupy R- i R« oraz n maja wyzej podane znaczenie poddaje sie reakcji z amina o wzorze ogólnym 3, w którym grupy R2 i R3 maja wyzej podane znaczenie, albo kwas o wzorze 2 przeprowadza w zwykly sposób w halogenek kwasowy albo bezwodnik kwasowy, który nastepnie poddaje reakcji z amina o wzorze ogólnym 3, przy czym Rg i R* maja wyzej podane znaczenie.
2. Sposób wytwarzania nowych amidów kwasów tienotriazolo-1,4-diazepino-2-karbo- ksylowych o wzorze ogólnym 1, w którym R^ oznacza prosta lub rozgaleziona grupe alkilowa o 1- 4 atomach wegla, podstawiona przez atom chlorowca albo przez grupe hydroksylowa, da¬ lej R1 oznacza grupe alkoksylowa o 2 lub 3 atomach wegla lub atom fluoru lub jodu, R~ i R,t które sa Jednakowe albo rózne, oznaczaja razem z atomem azotu 5-, 6- lub 7-czlonowy pierscien, który ewentualnie jako dalszy heteroatom zawiera atom azotu, tlenu lub siarki i przy czym drugi atom azotu Jest ewentualnie podstawiony grupa alkilowa o 2 - 4 atomach wegla, R^ oznacza grupe fenylowa, przy czym pierscien fenylowy jest ewentualnie podstawio¬ ny w pozycji 2 albo w pozycji 2 i 6 grupa metylowa, atomem chlorowca, grupa nitrowa albo grupa trifluorometylowa, albo oznacza grupe oC -pirydylcwa, zas n oznacza jedna z liczb 0-8, znamienny tym, ze kwas 2-karboksylowy o wzorze ogólnym 2, w którym grupy R* i R/ oraz n maja wyzej podane znaczenie, poddaje sie reakcji z amina o wzorze ogólnym 3, w którym grupy Rp i R3 maja wyzej podane znaczenie, albo kwas o wzorze 2 prze¬ prowadza w zwykly sposób w halogenek kwasowy lub bezwodnik kwasowy i te nastepnie poddaje reakcji z amina o wzorze ogólnym 3, w którym Rp i R, maja wyzej podane znaczenie.144 948 R<,-^ N, 2v s V " N-C-(CH2)n -b^IN I I R3' :N R4 WZÓR 1 R1 N. II*, s ^N HO-C-(CH2)n—£Y N WZÓR 2 Ra /R2 HN R3 WZÓR 3 — N WZÓR 3a CH3 \ WZÓR U N — Cl 0 WZtfR 5CH3 HC CH3 \j- / WZÓR 6 144 948 CH3 \ CH- / N- WZdR 7 D- WZÓR 8 CH3-N N- WZOR 10 o- WZdR 9 H WZÓR 11 HrC 5^2 \ N— H5C2^ WZdR 12 0 N — \ / WZÓR 13 N. CH2CH20H CH2CH2OH o WZÓR U WZdR 15144 948 PL PL PL
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19853502392 DE3502392A1 (de) | 1985-01-25 | 1985-01-25 | Neue thieno-triazolo-1,4-diazepino-2- carbonsaeureamide, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
Publications (2)
Publication Number | Publication Date |
---|---|
PL257602A1 PL257602A1 (en) | 1987-05-04 |
PL144948B1 true PL144948B1 (en) | 1988-07-30 |
Family
ID=6260695
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1986257602A PL144948B1 (en) | 1985-01-25 | 1986-01-23 | Method of obtaining novel thienotriazolo-1,4-diazepin-2-carboxylamides |
Country Status (28)
Country | Link |
---|---|
US (3) | US4968794A (pl) |
EP (1) | EP0194416B1 (pl) |
JP (2) | JPH0633278B2 (pl) |
KR (1) | KR920010711B1 (pl) |
AT (1) | ATE42556T1 (pl) |
AU (1) | AU584663B2 (pl) |
CA (1) | CA1269373A (pl) |
CS (1) | CS254992B2 (pl) |
CZ (1) | CZ410791A3 (pl) |
DD (3) | DD265799A5 (pl) |
DE (2) | DE3502392A1 (pl) |
DK (2) | DK165323C (pl) |
ES (3) | ES8704949A1 (pl) |
FI (1) | FI86851C (pl) |
GR (1) | GR860189B (pl) |
HK (1) | HK75792A (pl) |
HU (2) | HU195821B (pl) |
IE (1) | IE58728B1 (pl) |
IL (1) | IL77702A (pl) |
MX (1) | MX9203258A (pl) |
NO (2) | NO164029C (pl) |
NZ (1) | NZ214926A (pl) |
PL (1) | PL144948B1 (pl) |
PT (1) | PT81898B (pl) |
SG (1) | SG44292G (pl) |
SU (1) | SU1402265A3 (pl) |
YU (2) | YU44280B (pl) |
ZA (1) | ZA86542B (pl) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3502392A1 (de) * | 1985-01-25 | 1986-07-31 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue thieno-triazolo-1,4-diazepino-2- carbonsaeureamide, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
ES2037013T3 (es) * | 1986-01-21 | 1993-06-16 | Boehringer Ingelheim Kg | Procedimiento para preparar tieno-1,4-diazepinas. |
DE3610848A1 (de) * | 1986-04-01 | 1987-10-15 | Boehringer Ingelheim Kg | Neue 1,4-diazepine |
PH30676A (en) * | 1986-07-22 | 1997-09-16 | Boehringer Ingelhein Kg | Hetrazepine compounds which have useful pharmaceutical utility |
DE3745135C2 (de) * | 1986-10-21 | 1999-05-12 | Korth Ruth | Verwendung von hydrophilen Triazolothieno-diazepinen zur Behandlung von Arteriosklerose |
EP0268242B1 (en) * | 1986-11-17 | 1992-03-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Paf-antagonistic thienotriazolodiazepine compounds and pharmaceutical uses thereof |
DE3725130C2 (de) * | 1987-07-29 | 1996-12-12 | Boehringer Ingelheim Kg | Tritium-oder ·1··4·C-markiertes 4-(2-Chlorphenyl)-9-methyl-2-[3-(4-morpholinyl)-3-propanon-1-yl]-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin, Verfahren zu deren Herstellung und deren Verwendung als Radiorezeptorassay sowie zu diagnostischen Zwecken |
US5895785A (en) * | 1987-10-20 | 1999-04-20 | Ruth Korth | Treatment and prevention of disorders mediated by LA-paf or endothelial cells |
US4959361A (en) * | 1987-12-18 | 1990-09-25 | Hoffmann-La Roche Inc. | Triazolo(4,3-A)(1,4)benzodiazepines and thieno (3,2-F)(1,2,4)triazolo(4,3-A)(1,4)diazepine compounds which have useful activity as platelet activating factor (PAF) antagonists |
CA1324863C (en) * | 1988-01-30 | 1993-11-30 | Minoru Moriwaki | Thienotriazolodiazepine compounds and pharmaceutical uses thereof |
EP0338993A1 (en) * | 1988-04-21 | 1989-10-25 | Sandoz Ag | 6-Aryl-substituted-4h-thieno[2,3-e][1,2,4]triazolo [3,4-c][1,4]diazepines |
JPH0655673B2 (ja) * | 1988-04-27 | 1994-07-27 | シェリング・コーポレーション | Paf拮抗薬‐抗ヒスタミン剤の組合せ及び使用方法 |
US5334592A (en) * | 1988-04-27 | 1994-08-02 | Schering Corporation | Certain PAF antagonist antihistamine combinations and methods |
CA1322367C (en) * | 1988-05-17 | 1993-09-21 | Yoshitomi Pharmaceutical Industries Ltd. | Thienotriazolodiazepine compounds and pharmaceutical uses thereof |
US5221671A (en) * | 1988-10-31 | 1993-06-22 | Eisai Co., Ltd. | Triazolo-1,4-diazepine derivatives and their use in pharmaceuticals |
US5468740A (en) * | 1988-10-31 | 1995-11-21 | Eisai Co., Ltd. | 1,4-diazepine derivative and its pharmaceutical use |
RU2117670C1 (ru) * | 1988-10-31 | 1998-08-20 | Эйсай Ко., Лтд. | Производные триазоло[1,4]диазепина и способы их получения |
FI95708C (fi) | 1988-10-31 | 1996-03-11 | Eisai Co Ltd | Analogiamenetelmä 1,4-diatsepiinijohdannaisen ja sen farmaseuttisesti sopivan suolan valmistamiseksi |
US5304553A (en) * | 1988-10-31 | 1994-04-19 | Eisai Co., Ltd. | 1,4-diazepine derivative and its pharmaceutical use |
US5382579A (en) * | 1988-10-31 | 1995-01-17 | Eisai Co., Ltd. | Triazolo-1,4-diazepine derivatives and their use in pharmaceuticals |
EP0387613A1 (de) * | 1989-03-03 | 1990-09-19 | Boehringer Ingelheim Kg | Neue Thienodiazepine |
DE4010528A1 (de) * | 1990-04-02 | 1991-10-17 | Boehringer Ingelheim Kg | Praeparativ chromatographisches trennverfahren zur herstellung enantiomerenreiner hetrazepine |
CA2083611A1 (en) * | 1990-05-31 | 1991-12-01 | David Frederick Woodward | Use of platelet activating factor antagonists as anti-pruritic agents |
DE4027470A1 (de) * | 1990-08-30 | 1992-03-05 | Boehringer Ingelheim Kg | Neue hetrazepinoide amide |
DE4128579A1 (de) * | 1991-08-28 | 1993-03-04 | Boehringer Ingelheim Kg | Verwendung von 4-(2-chlorphenyl)-9-methyl-2-(3(4-morpholinyl)-3-propanon-1-y1)-6h-thieno-(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepin zur behandlung der allergischen rhinitis |
DE69133083C5 (de) * | 1991-11-04 | 2007-05-31 | Korth, Ruth-Maria, Dr.med. | Behandlung und Vorbeugung von erhöhten Lyso-PAF-Spiegel mediierten mentalen Erkrankungen mit PAF-Antagonisten |
TW219935B (pl) * | 1991-12-25 | 1994-02-01 | Mitsubishi Chemicals Co Ltd | |
DE4200619A1 (de) * | 1992-01-13 | 1993-07-15 | Boehringer Ingelheim Kg | Verwendung von 4-(2-chlorphenyl)-9-methyl-2-/3(4-morpholinyl)-3-propanon-1-yl/-6h-thieno-/3,2-f//1,2,4/ triazolo/4,3-a//1,4/diazepin zur behandlung der dysmenorrhes |
GB9207645D0 (en) * | 1992-04-08 | 1992-05-27 | Smithkline Beecham Corp | Methods |
EP0656004A1 (en) * | 1992-08-20 | 1995-06-07 | Cytomed, Inc. | Dual functional anti-inflammatory and immunosuppressive agents |
US5288514A (en) * | 1992-09-14 | 1994-02-22 | The Regents Of The University Of California | Solid phase and combinatorial synthesis of benzodiazepine compounds on a solid support |
US5302590A (en) * | 1992-12-18 | 1994-04-12 | Hoffmann-La Roche Inc. | Compounds useful as dual antagonists of platelet activating factor and leukotriene D4 |
CA2202985A1 (en) * | 1994-11-08 | 1996-05-17 | Haruhiko Makino | Thienopyridine or thienopyrimidine derivatives and their use |
WO1998058930A1 (fr) | 1997-06-25 | 1998-12-30 | Nikken Chemicals Co., Ltd. | Composes de triazolo-1,4-diazepine et composition medicinale les contenant |
AP2501A (en) | 2003-05-30 | 2012-10-22 | Ranbaxy Lab Ltd | Substituted pyrrole derivatives |
US7223167B2 (en) * | 2005-04-01 | 2007-05-29 | Cnh America Llc | Anti-wind wiper with adjustable extension |
EP1948599A1 (en) | 2005-11-08 | 2008-07-30 | Ranbaxy Laboratories Limited | Process for (3r, 5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4- [(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3, 5-dihydroxy-heptanoic acid hemi calcium salt |
US9638493B2 (en) | 2011-11-26 | 2017-05-02 | Orval E. Bowman | Pointing devices, apparatus, systems and methods for high shock environments |
WO2022101377A1 (en) | 2020-11-16 | 2022-05-19 | Boehringer Ingelheim International Gmbh | Cyclopentathiophene carboxamide derivatives as platelet activating factor receptor antagonists |
CN118414340A (zh) | 2021-12-22 | 2024-07-30 | 勃林格殷格翰国际有限公司 | 作为血小板活化因子受体拮抗剂的环戊烷并噻吩甲酰胺衍生物 |
Family Cites Families (11)
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PH12303A (en) * | 1973-02-08 | 1979-01-16 | Hoffmann La Roche | Thienotriazolodiazepine derivatives |
DE2503235A1 (de) * | 1975-01-27 | 1976-07-29 | Boehringer Sohn Ingelheim | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen |
US4201712A (en) * | 1975-07-16 | 1980-05-06 | Boehringer Ingelheim Gmbh | Process for preparation of 6-aryl-4H-s-triazolo-[3,4-c]-thieno-[2,3-e]-1,4-diazepines |
AU518438B2 (en) * | 1978-04-26 | 1981-10-01 | Boehringer Ingelheim International Gmbh | Substituted 6-aryl-4h-s-triazolo-3,4-c-thieno-2,3-e-1,4-diazepines |
AU520063B2 (en) * | 1978-07-13 | 1982-01-14 | Boehringer Ingelheim International Gmbh | Substituted 4h-s-triazolo(3,4-c)thieno(2,3-e)1,4-diazepines |
DE3435973A1 (de) * | 1984-10-01 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Diazepine enthaltende pharmazeutische zusammensetzungen mit paf-antagonistischer wirkung |
DE3502392A1 (de) * | 1985-01-25 | 1986-07-31 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue thieno-triazolo-1,4-diazepino-2- carbonsaeureamide, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
ES2037013T3 (es) * | 1986-01-21 | 1993-06-16 | Boehringer Ingelheim Kg | Procedimiento para preparar tieno-1,4-diazepinas. |
WO1988009333A1 (en) * | 1987-05-28 | 1988-12-01 | Yoshitomi Pharmaceutical Industries, Ltd. | Thieno(triazolo)diazepine compound and medicinal application of the same |
US4959361A (en) * | 1987-12-18 | 1990-09-25 | Hoffmann-La Roche Inc. | Triazolo(4,3-A)(1,4)benzodiazepines and thieno (3,2-F)(1,2,4)triazolo(4,3-A)(1,4)diazepine compounds which have useful activity as platelet activating factor (PAF) antagonists |
US4914096A (en) * | 1988-04-21 | 1990-04-03 | Sandoz Pharmaceuticals Corp. | 6-aryl-substituted-4H-thieno(2,3-e)(1,2,4)triazolo(3,4-c)(1,4)diazepines |
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1985
- 1985-01-25 DE DE19853502392 patent/DE3502392A1/de not_active Withdrawn
- 1985-12-23 NO NO855260A patent/NO164029C/no unknown
-
1986
- 1986-01-16 SU SU864008368A patent/SU1402265A3/ru active
- 1986-01-20 DE DE8686100656T patent/DE3663028D1/de not_active Expired
- 1986-01-20 EP EP86100656A patent/EP0194416B1/de not_active Expired
- 1986-01-20 YU YU78/86A patent/YU44280B/xx unknown
- 1986-01-20 AT AT86100656T patent/ATE42556T1/de not_active IP Right Cessation
- 1986-01-21 CS CS86452A patent/CS254992B2/cs not_active IP Right Cessation
- 1986-01-22 FI FI860296A patent/FI86851C/fi not_active IP Right Cessation
- 1986-01-23 GR GR860189A patent/GR860189B/el not_active IP Right Cessation
- 1986-01-23 DD DD86311014A patent/DD265799A5/de not_active IP Right Cessation
- 1986-01-23 PL PL1986257602A patent/PL144948B1/pl unknown
- 1986-01-23 DD DD86311011A patent/DD265899A5/de not_active IP Right Cessation
- 1986-01-23 DD DD86286429A patent/DD263063A5/de unknown
- 1986-01-24 PT PT81898A patent/PT81898B/pt not_active IP Right Cessation
- 1986-01-24 HU HU852044A patent/HU195821B/hu not_active IP Right Cessation
- 1986-01-24 IL IL77702A patent/IL77702A/xx not_active IP Right Cessation
- 1986-01-24 JP JP61013605A patent/JPH0633278B2/ja not_active Expired - Fee Related
- 1986-01-24 DK DK036786A patent/DK165323C/da not_active IP Right Cessation
- 1986-01-24 ES ES551198A patent/ES8704949A1/es not_active Expired
- 1986-01-24 NZ NZ214926A patent/NZ214926A/xx unknown
- 1986-01-24 AU AU52728/86A patent/AU584663B2/en not_active Ceased
- 1986-01-24 ZA ZA85542A patent/ZA86542B/xx unknown
- 1986-01-24 IE IE20986A patent/IE58728B1/en not_active IP Right Cessation
- 1986-01-24 CA CA000500345A patent/CA1269373A/en not_active Expired - Fee Related
- 1986-01-24 KR KR1019860000445A patent/KR920010711B1/ko not_active IP Right Cessation
- 1986-01-24 HU HU86356A patent/HU193624B/hu not_active IP Right Cessation
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1987
- 1987-01-21 ES ES557344A patent/ES8802523A1/es not_active Expired
- 1987-01-21 ES ES557343A patent/ES8802426A1/es not_active Expired
- 1987-05-05 YU YU79987A patent/YU46049B/sh unknown
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1988
- 1988-10-03 US US07/252,725 patent/US4968794A/en not_active Expired - Lifetime
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1989
- 1989-09-13 JP JP1238305A patent/JPH0651704B2/ja not_active Expired - Fee Related
- 1989-11-22 NO NO894640A patent/NO166646C/no unknown
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1990
- 1990-06-15 US US07/539,416 patent/US5082839A/en not_active Expired - Lifetime
-
1991
- 1991-10-11 US US07/774,683 patent/US5155103A/en not_active Expired - Fee Related
- 1991-12-27 CZ CS914107A patent/CZ410791A3/cs unknown
-
1992
- 1992-04-06 DK DK92462A patent/DK46292D0/da not_active Application Discontinuation
- 1992-04-22 SG SG442/92A patent/SG44292G/en unknown
- 1992-06-24 MX MX9203258A patent/MX9203258A/es unknown
- 1992-10-01 HK HK757/92A patent/HK75792A/xx not_active IP Right Cessation
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