JPS605580B2 - 新ナフタレン誘導体の製法 - Google Patents
新ナフタレン誘導体の製法Info
- Publication number
- JPS605580B2 JPS605580B2 JP57190681A JP19068182A JPS605580B2 JP S605580 B2 JPS605580 B2 JP S605580B2 JP 57190681 A JP57190681 A JP 57190681A JP 19068182 A JP19068182 A JP 19068182A JP S605580 B2 JPS605580 B2 JP S605580B2
- Authority
- JP
- Japan
- Prior art keywords
- naphthalene derivatives
- formula
- manufacturing
- compound
- new naphthalene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/26—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydration of carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
【発明の詳細な説明】
本発明は製薬上活性を有するナフタレン誘導体を製造す
る方法に関するものである。
る方法に関するものである。
ある種のナフタレン誘導体は有用な抗炎症性を有し、種
々のりゥマチ性および関節炎性病状の治療に使用するの
に適していることが知られている。
々のりゥマチ性および関節炎性病状の治療に使用するの
に適していることが知られている。
臨床的に使用できることが知られている特に効果がある
ナフタレン譲導体のひとつに式(1)を有するナプロキ
セン(Naproxen)がある。この化合物およびこ
れに関連するある種の化合物は英国特許第127113
2号、同第1274271号、同第1274272号、
同第1274273号、同第1291386号、同第1
211134号、同第1297306号、同第1276
261号、同第1216882号、同第1289041
号、同第1321347号、および同第1296493
号の各明細書に記載されている。この種の化合物の薬理
学的効果も文献〔J.Med.Chem.、13 20
3(1970)、J.Pham.E×p.mera、1
79 114、(1971)〕に記載されている。残念
ながら式(1)の化合物は治療用投与量をあまり大して
越えない投与量で、ある被験者の胃腸に激しい刺激を生
じることがある。本発明によって、他のナフタレン譲導
体が良好な抗炎症性を有するばかりでなく、胃腸内の刺
激に塞いて体重に対する薬効量の比率が改良されている
ことが分かった。
ナフタレン譲導体のひとつに式(1)を有するナプロキ
セン(Naproxen)がある。この化合物およびこ
れに関連するある種の化合物は英国特許第127113
2号、同第1274271号、同第1274272号、
同第1274273号、同第1291386号、同第1
211134号、同第1297306号、同第1276
261号、同第1216882号、同第1289041
号、同第1321347号、および同第1296493
号の各明細書に記載されている。この種の化合物の薬理
学的効果も文献〔J.Med.Chem.、13 20
3(1970)、J.Pham.E×p.mera、1
79 114、(1971)〕に記載されている。残念
ながら式(1)の化合物は治療用投与量をあまり大して
越えない投与量で、ある被験者の胃腸に激しい刺激を生
じることがある。本発明によって、他のナフタレン譲導
体が良好な抗炎症性を有するばかりでなく、胃腸内の刺
激に塞いて体重に対する薬効量の比率が改良されている
ことが分かった。
このような化合物は式(〇)を有する化合物である。
式(0)の化合物は人間に対する経口投与に適した抗炎
性および(または)鎮痛性組成物に入れることができる
。
性および(または)鎮痛性組成物に入れることができる
。
この種の組成物は錠剤、カプセル剤、粉末等任意の形に
することができる。単位投与量を含有する形のときには
通常式(D)の薬効成分を20〜1000の9、さらに
一般的には100〜600の夕を含有する。このような
単位投与量を含有する形は1日1回以上、好ましくは1
日2〜4回に、70k9の体重の人間の1日投与量が通
常300〜3000の9、さらに好ましくは500〜2
000の2たとえば600〜1600ののこなるように
することができる。本発明によれば下記よりなる前記(
0)の新しい化合物の製法が得られる。式(m) を有する化合物を還元して式(0) を有する化合物とする。
することができる。単位投与量を含有する形のときには
通常式(D)の薬効成分を20〜1000の9、さらに
一般的には100〜600の夕を含有する。このような
単位投与量を含有する形は1日1回以上、好ましくは1
日2〜4回に、70k9の体重の人間の1日投与量が通
常300〜3000の9、さらに好ましくは500〜2
000の2たとえば600〜1600ののこなるように
することができる。本発明によれば下記よりなる前記(
0)の新しい化合物の製法が得られる。式(m) を有する化合物を還元して式(0) を有する化合物とする。
カルボニル基である式(m)の化合物を還元して対応す
る第二アルコールにする反応は遷移金属触媒の存在下の
水素添加または水素化物たとえばNaB日4、LiAI
H4等の使用のような通常行なわれている還元法を使用
して実施することができる。
る第二アルコールにする反応は遷移金属触媒の存在下の
水素添加または水素化物たとえばNaB日4、LiAI
H4等の使用のような通常行なわれている還元法を使用
して実施することができる。
実施例 14一(6−メトキシ−2′−ナフチル)ーベ
ンタン−2ーオルメタノール100凧【中の4一(6−
メトキシ−2ーナフチル)ーベンタン−2−オン2夕の
溶液を氷中で冷却し、これに水素化ホウ素ナトリウム1
夕を加え、溶液を1時間かきまぜてから、希塩酸で酸性
にし、エーテル100の【ずつで3回抽出する。
ンタン−2ーオルメタノール100凧【中の4一(6−
メトキシ−2ーナフチル)ーベンタン−2−オン2夕の
溶液を氷中で冷却し、これに水素化ホウ素ナトリウム1
夕を加え、溶液を1時間かきまぜてから、希塩酸で酸性
にし、エーテル100の【ずつで3回抽出する。
水洗したエーテル抽出物を無水Na2S04で乾燥し、
蒸発すると、透明な無色油状物1.3夕を得る。IR三
3400肌‐10日の吸収帯、COの吸収帯は消失。
蒸発すると、透明な無色油状物1.3夕を得る。IR三
3400肌‐10日の吸収帯、COの吸収帯は消失。
Claims (1)
- 【特許請求の範囲】 1 式(III) ▲数式、化学式、表等があります▼ を有する化合物を還元することを特徴とする式(II)▲
数式、化学式、表等があります▼ を有する化合物を製造する方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB42550 | 1973-09-11 | ||
GB4255073A GB1474377A (en) | 1973-09-11 | 1973-09-11 | Naphthalene derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5896036A JPS5896036A (ja) | 1983-06-07 |
JPS605580B2 true JPS605580B2 (ja) | 1985-02-12 |
Family
ID=10424914
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP49103764A Expired JPS5920655B2 (ja) | 1973-09-11 | 1974-09-09 | 新ナフタレン誘導体の製法 |
JP57190679A Expired JPS6033818B2 (ja) | 1973-09-11 | 1982-10-29 | 新ナフタレン誘導体の製法 |
JP57190681A Expired JPS605580B2 (ja) | 1973-09-11 | 1982-10-29 | 新ナフタレン誘導体の製法 |
JP57190680A Expired JPS5921850B2 (ja) | 1973-09-11 | 1982-10-29 | 新ナフタレン誘導体の製法 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP49103764A Expired JPS5920655B2 (ja) | 1973-09-11 | 1974-09-09 | 新ナフタレン誘導体の製法 |
JP57190679A Expired JPS6033818B2 (ja) | 1973-09-11 | 1982-10-29 | 新ナフタレン誘導体の製法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57190680A Expired JPS5921850B2 (ja) | 1973-09-11 | 1982-10-29 | 新ナフタレン誘導体の製法 |
Country Status (15)
Country | Link |
---|---|
JP (4) | JPS5920655B2 (ja) |
BE (1) | BE819794A (ja) |
CH (8) | CH613932A5 (ja) |
CY (2) | CY1083A (ja) |
DE (2) | DE2442305C2 (ja) |
DK (1) | DK156642C (ja) |
FR (1) | FR2242972B1 (ja) |
GB (1) | GB1474377A (ja) |
HK (2) | HK56280A (ja) |
IE (1) | IE40001B1 (ja) |
KE (2) | KE3082A (ja) |
MY (2) | MY8100198A (ja) |
NL (1) | NL175812C (ja) |
SE (2) | SE420598B (ja) |
ZA (1) | ZA745441B (ja) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL52006A0 (en) * | 1976-05-13 | 1977-07-31 | Beecham Group Ltd | Novel nephthalene derivatives their preparation and pharmaceutical compositions containing them |
GB2014993B (en) * | 1977-11-03 | 1982-05-12 | Beecham Group Ltd | Chemical compounds |
EP0003074B1 (en) * | 1978-01-07 | 1981-04-15 | Beecham Group Plc | Process for the preparation of 4-(6-methoxy-2-naphthyl)butan-2-one and 2-acetyl-3-(6-methoxy-2-naphthyl) propenoic acid esters |
CA1142965A (en) * | 1979-06-08 | 1983-03-15 | Alexander C. Goudie | Substituted decalins, their preparation and use |
GB8416638D0 (en) * | 1984-06-29 | 1984-08-01 | Beecham Group Plc | Topical treatment and composition |
GB8607119D0 (en) * | 1986-03-21 | 1986-04-30 | Beecham Group Plc | Process |
DE69120491T2 (de) * | 1990-09-18 | 1996-11-14 | Fujitsu Ltd | Cursorverschiebungssteuerungsgerät für eine Rechneranzeige |
GB9108128D0 (en) * | 1991-04-15 | 1991-06-05 | Zambeletti Spa L | Novel formulation |
GB9201857D0 (en) | 1992-01-29 | 1992-03-18 | Smithkline Beecham Plc | Novel compound |
GB9222849D0 (en) * | 1992-10-31 | 1992-12-16 | Smithkline Beecham Plc | Novel use of pharmaceutical compositions |
WO1997032837A1 (fr) * | 1996-03-06 | 1997-09-12 | Sumitomo Pharmaceuticals Co., Ltd. | Derives estrogenes non steroidiens |
US5861538A (en) * | 1997-08-04 | 1999-01-19 | Albemarle Corporation | Production of alkoxynaphthyl-substituted ketones from naphthaldehydes |
JP2006511445A (ja) * | 2002-06-07 | 2006-04-06 | コーティカル・ピーティーワイ・リミテッド | マクロファージ遊走阻止因子(mif)のサイトカインまたは生物学的活性を阻害するナフタレン誘導体 |
EP2123621A1 (de) | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma Aktiengesellschaft | Neue {F-18}-markierte L-Glutaminsäure- und L-Glutaminderivate (I), ihre Verwendung sowie Verfahren zu ihrer Herstellung |
EP2123619A1 (de) | 2008-05-20 | 2009-11-25 | Bayer Schering Pharma AG | Neue [F-18]-Markierte L-Glutaminsäure-und L-Glutaminderivate (II), ihre Verwendung sowie Verfahren zu ihrer Herstellung |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NO125971B (ja) * | 1969-05-22 | 1972-12-04 | Syntex Corp | |
BR6915468D0 (pt) * | 1969-10-09 | 1973-03-13 | Syntex Corp | Processo para a preparacao de d 2-(6-substituido-2-naftil)-propanal |
-
1973
- 1973-09-11 GB GB4255073A patent/GB1474377A/en not_active Expired
-
1974
- 1974-08-20 CY CY1083A patent/CY1083A/xx unknown
- 1974-08-20 CY CY1082A patent/CY1082A/xx unknown
- 1974-08-21 IE IE1740/74A patent/IE40001B1/xx unknown
- 1974-08-26 ZA ZA00745441A patent/ZA745441B/xx unknown
- 1974-09-04 DE DE2442305A patent/DE2442305C2/de not_active Expired
- 1974-09-04 DE DE2463219A patent/DE2463219C2/de not_active Expired
- 1974-09-05 FR FR7430151A patent/FR2242972B1/fr not_active Expired
- 1974-09-05 SE SE7411261A patent/SE420598B/xx not_active IP Right Cessation
- 1974-09-09 JP JP49103764A patent/JPS5920655B2/ja not_active Expired
- 1974-09-10 DK DK477674A patent/DK156642C/da not_active IP Right Cessation
- 1974-09-11 CH CH999477A patent/CH613932A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999677A patent/CH603524A5/xx not_active IP Right Cessation
- 1974-09-11 BE BE148417A patent/BE819794A/xx active Protection Beyond IP Right Term
- 1974-09-11 CH CH999777A patent/CH603525A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH1236974A patent/CH599090A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999877A patent/CH603526A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999377A patent/CH603523A5/xx not_active IP Right Cessation
- 1974-09-11 NL NLAANVRAGE7412060,A patent/NL175812C/xx not_active IP Right Cessation
- 1974-09-11 CH CH999977A patent/CH603527A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999577A patent/CH603543A5/xx not_active IP Right Cessation
-
1979
- 1979-08-23 SE SE7907064A patent/SE7907064A0/sv unknown
-
1980
- 1980-09-06 KE KE3082A patent/KE3082A/xx unknown
- 1980-09-06 KE KE3081A patent/KE3081A/xx unknown
- 1980-10-02 HK HK562/80A patent/HK56280A/xx unknown
- 1980-10-02 HK HK561/80A patent/HK56180A/xx unknown
-
1981
- 1981-12-30 MY MY198/81A patent/MY8100198A/xx unknown
- 1981-12-30 MY MY197/81A patent/MY8100197A/xx unknown
-
1982
- 1982-10-29 JP JP57190679A patent/JPS6033818B2/ja not_active Expired
- 1982-10-29 JP JP57190681A patent/JPS605580B2/ja not_active Expired
- 1982-10-29 JP JP57190680A patent/JPS5921850B2/ja not_active Expired
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