FI68820C - Foerfarande foer framstaellning av terapeutiskt anvaendbara amnotiazoler - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara amnotiazoler Download PDFInfo
- Publication number
- FI68820C FI68820C FI791754A FI791754A FI68820C FI 68820 C FI68820 C FI 68820C FI 791754 A FI791754 A FI 791754A FI 791754 A FI791754 A FI 791754A FI 68820 C FI68820 C FI 68820C
- Authority
- FI
- Finland
- Prior art keywords
- phenyl
- carbon atoms
- hydrogen
- compounds
- mol
- Prior art date
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- 238000010438 heat treatment Methods 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- -1 monosubstituted phenyl Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
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- 238000006243 chemical reaction Methods 0.000 claims description 14
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
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- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
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- 239000002253 acid Substances 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
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- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims 9
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- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 1
- HKHXNMWREYJWGY-UHFFFAOYSA-N n-(furan-2-ylmethyl)-5-methyl-4-phenyl-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.N=1C(C=2C=CC=CC=2)=C(C)SC=1NCC1=CC=CO1 HKHXNMWREYJWGY-UHFFFAOYSA-N 0.000 description 1
- JKOBOYCYCFKVJC-UHFFFAOYSA-N n-benzhydryl-1,3-thiazol-2-amine Chemical class N=1C=CSC=1NC(C=1C=CC=CC=1)C1=CC=CC=C1 JKOBOYCYCFKVJC-UHFFFAOYSA-N 0.000 description 1
- QSLBXMRJPQRVER-UHFFFAOYSA-N n-benzyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1CNC1=NC=CS1 QSLBXMRJPQRVER-UHFFFAOYSA-N 0.000 description 1
- GJRJECJQBNZINV-UHFFFAOYSA-N n-benzyl-4-phenyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1CNC(SC=1)=NC=1C1=CC=CC=C1 GJRJECJQBNZINV-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- OGVGQYZRJXSMGC-UHFFFAOYSA-N n-phenyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1NC1=NC=CS1 OGVGQYZRJXSMGC-UHFFFAOYSA-N 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- NCYDRNOBBHFJHE-UHFFFAOYSA-N propane-1,2-diol;prop-1-ene Chemical compound CC=C.CC(O)CO NCYDRNOBBHFJHE-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B15/00—Nails; Staples
- F16B15/0023—Nail plates
- F16B2015/0076—Nail plates with provisions for additional fastening means, e.g. hooks, holes for separate screws or nails, adhesive
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (5)
1. Förfarande för framställning av en terapeutiskt användbar förening med formeln I ‘ j- N R3 \ J- NH-R, /X väri är en av grupperna -CH^ , “C^-Cl^-NH-X och - (CH2) Y, X väri X är fenyl eller monosubstituerad fenyl, varvid nämnda substituent kan vara alkyl med 1-3 kolatomer, hydroxi, alkoxi med 1-3 kol-atomer, klor, brom eller fluor; Y är tienyl, monosubstituerad tienyl, furyl eller monosubstituerad furyl, varvid nämnda substituent kan vara alkyl med 1-3 kolatomer, klor, brom eller fluor; m är ett eller tvä; R2 är fenyl, tienyl eller monosubstituerad fenyl, varvid nämnda substituent kan vara alkyl med 1-3 kolatomer, hydroxi, alkoxi med 1-3 kolatomer, klor, brom och fluor; och R^ är väte, alkyl med 1-3 kolatomer, fenyl eller monosubstituerad fenyl, varvid nämnda substituent kan vara alkyl med 1-3 kolatomer, alkoxi med 1-3 kolatomer, brom, klor eller fluor, k ä n - netecknat därav, att ett lämpligt substituerat N-aralkyl- S „ li -X tiouera med formeln R^NHCNI^, eller, ifali önskvärt da R1 är CH^ , S X II bis-substituerat N-aralkyl-tiourea med formeln R^NHCNHR^, väri R^ och X är som tidigare definierats, omsätts med en alfa-halogenföre-ning med formeln R2COCH(Z)R3, väri R2 och R3 är som tidigare definierats och Z är halogen, och, ifall önskvärt, omvandlas sedan föreningen med formeln I tili ett farmaceutiskt godtagbart syraadditionssalt.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att reaktionen uföres i en n-alkanol med 1-6 kolatomer och vid en temperatur mellan 50 och 175°C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91183078A | 1978-06-02 | 1978-06-02 | |
| US91183078 | 1978-06-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI791754A FI791754A (fi) | 1979-11-26 |
| FI68820B FI68820B (fi) | 1985-07-31 |
| FI68820C true FI68820C (fi) | 1985-11-11 |
Family
ID=25430923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI791754A FI68820C (fi) | 1978-06-02 | 1979-06-01 | Foerfarande foer framstaellning av terapeutiskt anvaendbara amnotiazoler |
Country Status (36)
| Country | Link |
|---|---|
| JP (1) | JPS5936988B2 (sv) |
| AR (1) | AR226285A1 (sv) |
| AT (1) | AT373248B (sv) |
| AU (1) | AU511242B2 (sv) |
| BE (1) | BE876732A (sv) |
| CA (1) | CA1117949A (sv) |
| CH (1) | CH639653A5 (sv) |
| CS (1) | CS216927B2 (sv) |
| DD (1) | DD144055A5 (sv) |
| DE (1) | DE2922523C2 (sv) |
| DK (1) | DK150068C (sv) |
| EG (1) | EG14354A (sv) |
| ES (1) | ES481220A1 (sv) |
| FI (1) | FI68820C (sv) |
| FR (1) | FR2427333A1 (sv) |
| GB (1) | GB2022085B (sv) |
| GR (1) | GR73142B (sv) |
| HK (1) | HK66487A (sv) |
| HU (1) | HU180045B (sv) |
| IE (1) | IE48426B1 (sv) |
| IL (1) | IL57450A (sv) |
| IT (1) | IT1121238B (sv) |
| KE (1) | KE3459A (sv) |
| LU (1) | LU81349A1 (sv) |
| MY (1) | MY8500318A (sv) |
| NL (1) | NL178421C (sv) |
| NO (1) | NO150760C (sv) |
| NZ (1) | NZ190623A (sv) |
| PH (1) | PH17020A (sv) |
| PL (1) | PL117515B1 (sv) |
| PT (1) | PT69718A (sv) |
| SE (1) | SE438333B (sv) |
| SG (1) | SG56184G (sv) |
| SU (1) | SU843746A3 (sv) |
| YU (1) | YU40997B (sv) |
| ZA (1) | ZA792729B (sv) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57501565A (sv) * | 1980-10-24 | 1982-09-02 | ||
| JPS57136579A (en) * | 1981-01-21 | 1982-08-23 | Mitsui Toatsu Chem Inc | Thiazolylurea derivative, its preparation, and pharmaceutical composition containing the same |
| EP0068033B1 (en) * | 1981-01-08 | 1985-07-10 | Mitsui Toatsu Kagaku Kabushiki Kaisha | N-(4-phenyl-2-thiazolyl)carbamate derivatives, process for their preparation, and medicinal composition containing same |
| JPS57116067A (en) * | 1981-01-12 | 1982-07-19 | Sankyo Kagaku Kk | Novel 8-quinolinesulfonyl derivative, its synthesis and use |
| US4501750A (en) * | 1981-01-13 | 1985-02-26 | Mitsui Toatsu Kaguku Kabushiki Kaisha | Thiazole compounds, a process for preparing same and a pharmaceutical composition containing the thiazole compounds |
| WO1982002386A1 (en) * | 1981-01-13 | 1982-07-22 | Sakano Isao | Aminothiazole derivatives,process for their preparation,and medicinal composition containing same |
| JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
| DE3227329A1 (de) * | 1982-07-22 | 1984-01-26 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 2-n,n-disubstituierten aminothiazolen |
| WO1986003203A1 (en) * | 1984-11-22 | 1986-06-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Thienylthiazole derivatives |
| FR2581063B1 (fr) * | 1985-04-30 | 1987-07-17 | Chauvin Blache Lab | Amino-2 thiazoles n-substitues, leur procede de preparation et leur application en therapeutique |
| JPS63152368A (ja) * | 1986-06-03 | 1988-06-24 | Sumitomo Pharmaceut Co Ltd | 新規なアミノアゾ−ル誘導体およびその酸付加塩 |
| JPH075579B2 (ja) * | 1986-09-01 | 1995-01-25 | 吉富製薬株式会社 | アミノチアゾ−ル化合物 |
| JPH0753666B2 (ja) * | 1987-09-14 | 1995-06-07 | 久光製薬株式会社 | 置換ジフェニルチアゾール誘導体からなる抗炎症剤 |
| ATE159622T1 (de) * | 1989-08-10 | 1997-11-15 | Commw Scient Ind Res Org | Verfahren zur herstellung von einer elektrosuspension von mikropartikeln |
| DE69132293D1 (de) * | 1991-03-07 | 2000-08-10 | Hisamitsu Pharmaceutical Co | Diphenylthiazolderivate mit antiinflammatorischer aktivität |
| FR2692893B1 (fr) * | 1992-06-24 | 1994-09-02 | Sanofi Elf | Dérivés alkylamino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| CA2195847A1 (en) * | 1994-07-27 | 1996-02-08 | John J. Talley | Substituted thiazoles for the treatment of inflammation |
| FR2754258B1 (fr) | 1996-10-08 | 1998-12-31 | Sanofi Sa | Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant |
| US7105550B2 (en) * | 2000-03-01 | 2006-09-12 | Christopher Love | 2,4-disubstituted thiazolyl derivatives |
| EP1423113A4 (en) * | 2001-08-13 | 2007-04-18 | Phenex Pharmaceuticals Ag | NR1H4 NUCLEAR RECEPTOR BINDING COMPOUNDS |
| WO2003027096A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Substituted 3-pyridyl imidazoles as c17,20 lyase inhibitors |
| PT1471054E (pt) | 2002-01-11 | 2009-09-23 | Daiichi Sankyo Co Ltd | Derivado de aminoálcool ou derivado de ácido fosfónico e composição medicinal que os contém |
| EP1555264A1 (en) * | 2004-01-15 | 2005-07-20 | Sireen AG | Five-membered heterocyclic compounds as inhibitors of SRC family protein kinase. |
| KR20110136901A (ko) | 2004-02-24 | 2011-12-21 | 상꾜 가부시키가이샤 | 아미노 알코올 화합물 |
| KR20080019213A (ko) | 2005-05-09 | 2008-03-03 | 아칠리온 파르마세우티칼스 인코포레이티드 | 티아졸 화합물 및 그 사용방법 |
| ES2389062T3 (es) | 2006-01-18 | 2012-10-22 | Amgen, Inc | Compuestos de tiazol como inhibidores de proteína cinasa B (PKB) |
| AU2008276521B2 (en) | 2007-07-17 | 2011-11-03 | Amgen Inc. | Heterocyclic modulators of PKB |
| AU2008276512A1 (en) | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of PKB |
| WO2012170951A2 (en) * | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9856240B2 (en) | 2011-10-19 | 2018-01-02 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN110590785B (zh) * | 2019-09-23 | 2021-02-02 | 武汉大学 | 一种氨基噻唑类化合物及其制备方法与抗肠道病毒71型的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3458526A (en) * | 1966-09-26 | 1969-07-29 | Upjohn Co | Certain 2-amino-4,5-bis(p-methoxyphenyl)thiazoles |
-
1979
- 1979-04-30 DK DK177679A patent/DK150068C/da not_active IP Right Cessation
- 1979-05-23 GB GB7917872A patent/GB2022085B/en not_active Expired
- 1979-05-29 CH CH501679A patent/CH639653A5/fr not_active IP Right Cessation
- 1979-05-30 CS CS793728A patent/CS216927B2/cs unknown
- 1979-05-30 EG EG333/79A patent/EG14354A/xx active
- 1979-05-31 SE SE7904798A patent/SE438333B/sv not_active IP Right Cessation
- 1979-05-31 YU YU1288/79A patent/YU40997B/xx unknown
- 1979-05-31 LU LU81349A patent/LU81349A1/xx unknown
- 1979-05-31 IL IL57450A patent/IL57450A/xx unknown
- 1979-05-31 SU SU792773929A patent/SU843746A3/ru active
- 1979-05-31 AU AU47634/79A patent/AU511242B2/en not_active Ceased
- 1979-05-31 CA CA000328805A patent/CA1117949A/en not_active Expired
- 1979-05-31 HU HU79PI679A patent/HU180045B/hu not_active IP Right Cessation
- 1979-05-31 PH PH22588A patent/PH17020A/en unknown
- 1979-06-01 AR AR276782A patent/AR226285A1/es active
- 1979-06-01 PL PL1979216030A patent/PL117515B1/pl unknown
- 1979-06-01 NZ NZ190623A patent/NZ190623A/en unknown
- 1979-06-01 NO NO791831A patent/NO150760C/no unknown
- 1979-06-01 NL NLAANVRAGE7904337,A patent/NL178421C/xx not_active IP Right Cessation
- 1979-06-01 DD DD79213371A patent/DD144055A5/de not_active IP Right Cessation
- 1979-06-01 GR GR59240A patent/GR73142B/el unknown
- 1979-06-01 AT AT0401679A patent/AT373248B/de not_active IP Right Cessation
- 1979-06-01 BE BE0/195534A patent/BE876732A/xx not_active IP Right Cessation
- 1979-06-01 ZA ZA792729A patent/ZA792729B/xx unknown
- 1979-06-01 FR FR7914164A patent/FR2427333A1/fr active Granted
- 1979-06-01 PT PT69718A patent/PT69718A/pt unknown
- 1979-06-01 JP JP54068781A patent/JPS5936988B2/ja not_active Expired
- 1979-06-01 IT IT23228/79A patent/IT1121238B/it active
- 1979-06-01 FI FI791754A patent/FI68820C/fi not_active IP Right Cessation
- 1979-06-01 ES ES481220A patent/ES481220A1/es not_active Expired
- 1979-06-01 DE DE2922523A patent/DE2922523C2/de not_active Expired
- 1979-08-08 IE IE1069/79A patent/IE48426B1/en unknown
-
1984
- 1984-08-13 SG SG561/84A patent/SG56184G/en unknown
- 1984-09-24 KE KE3459A patent/KE3459A/xx unknown
-
1985
- 1985-12-30 MY MY318/85A patent/MY8500318A/xx unknown
-
1987
- 1987-09-17 HK HK664/87A patent/HK66487A/xx unknown
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