JPS5896036A - 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
- JPS5896036A JPS5896036A JP57190681A JP19068182A JPS5896036A JP S5896036 A JPS5896036 A JP S5896036A JP 57190681 A JP57190681 A JP 57190681A JP 19068182 A JP19068182 A JP 19068182A JP S5896036 A JPS5896036 A JP S5896036A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- manufacture
- compounds
- naphthalene derivative
- novel 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.)
- Granted
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)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (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)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
め要約のデータは記録されません。
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の製法に
関するものである。
関するものである。
ある釉のナフタレン誘導体は有用な抗炎症性を有し、種
々のリウ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。
々のリウ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
ナフタレン誘導体のひとつに式(1)を有するナゾロキ
セン(Naproxen)がア7)。j(7)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1.2
71.132号、同第1.274.271号同第1.2
74.272号、同第1.274.273号、同第1.
291.386号、同第1.211.134号、同第1
.297.306号、同第1.276.261号、同第
1.216.882号、同第1.289.041号、同
第1.321.347号、および同第1.296.49
3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〔JeMed−Chem* 、13゜
203、(1970) 、J@Pham@Exp−Th
era。
ナフタレン誘導体のひとつに式(1)を有するナゾロキ
セン(Naproxen)がア7)。j(7)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1.2
71.132号、同第1.274.271号同第1.2
74.272号、同第1.274.273号、同第1.
291.386号、同第1.211.134号、同第1
.297.306号、同第1.276.261号、同第
1.216.882号、同第1.289.041号、同
第1.321.347号、および同第1.296.49
3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〔JeMed−Chem* 、13゜
203、(1970) 、J@Pham@Exp−Th
era。
179、 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。
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。
り
本発明によって、他のナス2レン誘導体が良好な抗炎症
性を有するばかシでなく、冑腸内の刺激に基いて体重に
対する薬効量の比率が改良されていることが分かった。
性を有するばかシでなく、冑腸内の刺激に基いて体重に
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(…)(式中、R1け水素原子ま
たはメチル基であり、点線は追加の結合を表わすかまた
は点線が達する二つの炭素原子の各々に結合した水素原
子を表わす)を有する化合物である。
たはメチル基であり、点線は追加の結合を表わすかまた
は点線が達する二つの炭素原子の各々に結合した水素原
子を表わす)を有する化合物である。
R1がメチル基である式(It)の化合物は投与量を多
くすると発情性作用を示す傾向があるが、R1が水素で
ある式i)の化合物はこの作用を示す傾向が小さくなる
。
くすると発情性作用を示す傾向があるが、R1が水素で
ある式i)の化合物はこの作用を示す傾向が小さくなる
。
式(II)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。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(II)の薬効成分を20〜1000■、さ
らに一般的には100〜600 my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l″i1日2〜4回に、70kC!の体重の人間の1
日投与量が通常300〜3000■、さらに好オしくに
500〜2000■たとえば600〜1600■に力る
ようにすることができる。
炎性および(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(II)の薬効成分を20〜1000■、さ
らに一般的には100〜600 my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l″i1日2〜4回に、70kC!の体重の人間の1
日投与量が通常300〜3000■、さらに好オしくに
500〜2000■たとえば600〜1600■に力る
ようにすることができる。
式(II)
(式中、R1は水素原子寸たはメチル基であり、点線は
追加の結合を表わすかまたは点線が達する二つの炭素原
子の各々に結合した水素原子を表わす)を有する化合物
を還元して式(II)(式中、R1および点線Fi!i
+述の意味を表わす)を有する化合物とする。
追加の結合を表わすかまたは点線が達する二つの炭素原
子の各々に結合した水素原子を表わす)を有する化合物
を還元して式(II)(式中、R1および点線Fi!i
+述の意味を表わす)を有する化合物とする。
カルボニル基である式(1)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NaBH4、LiAl
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NaBH4、LiAl
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。
接触水素添加はオレフィン系二重結合を還元することが
あるので、このような二重結合を有する化合物を製造す
るときには好ましくない。
あるので、このような二重結合を有する化合物を製造す
るときには好ましくない。
実施例1
4−(6’−メトキシ−2′−ナフチル)−ペンタン−
2−オル メタノール100rnl中の4−(6’−メトキシ−2
′−ナフチル)−ペンタン−2−オ> 2 t ノ溶液
を水中で冷却し、これに水素化ホウ累ナトリウム1t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100dずつで3回抽出する。水洗したエー
テル抽出物を無水Nag so4 で乾燥し、蒸発す
ると、透明な無色油状物1.3tを得る。
2−オル メタノール100rnl中の4−(6’−メトキシ−2
′−ナフチル)−ペンタン−2−オ> 2 t ノ溶液
を水中で冷却し、これに水素化ホウ累ナトリウム1t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100dずつで3回抽出する。水洗したエー
テル抽出物を無水Nag so4 で乾燥し、蒸発す
ると、透明な無色油状物1.3tを得る。
IR:3400tM−”OHの吸収帯、COの吸収帯は
消失 代理人 弁理士 秋 沢 政 光 他1名
消失 代理人 弁理士 秋 沢 政 光 他1名
Claims (1)
- (1)式(III) (式中、R1は水素原子またはメチル基であり、点線は
追加の結合を表わすかまたは点線が達する二つの炭素原
子の各々に結合した水素原子を表わす) を有する化合物を還元することを特徴とする式() (式中、R1は前述の意味を有する) を有する化合物の製法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB4255073A GB1474377A (en) | 1973-09-11 | 1973-09-11 | Naphthalene derivatives |
GB42550 | 1973-09-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5896036A true JPS5896036A (ja) | 1983-06-07 |
JPS605580B2 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 |
JP57190680A Expired JPS5921850B2 (ja) | 1973-09-11 | 1982-10-29 | 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 |
Family Applications Before (3)
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 |
JP57190680A Expired JPS5921850B2 (ja) | 1973-09-11 | 1982-10-29 | 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 |
Country Status (15)
Country | Link |
---|---|
JP (4) | JPS5920655B2 (ja) |
BE (1) | BE819794A (ja) |
CH (8) | CH603524A5 (ja) |
CY (2) | CY1083A (ja) |
DE (2) | DE2463219C2 (ja) |
DK (1) | DK156642C (ja) |
FR (1) | FR2242972B1 (ja) |
GB (1) | GB1474377A (ja) |
HK (2) | HK56180A (ja) |
IE (1) | IE40001B1 (ja) |
KE (2) | KE3081A (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 |
CN1675154A (zh) * | 2002-06-07 | 2005-09-28 | 科蒂科股份有限公司 | 抑制巨噬细胞移动抑制因子(mif)的细胞因子或生物活性的萘衍生物 |
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 DE2463219A patent/DE2463219C2/de not_active Expired
- 1974-09-04 DE DE2442305A patent/DE2442305C2/de not_active Expired
- 1974-09-05 SE SE7411261A patent/SE420598B/xx not_active IP Right Cessation
- 1974-09-05 FR FR7430151A patent/FR2242972B1/fr not_active Expired
- 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 CH999677A patent/CH603524A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999377A patent/CH603523A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999977A patent/CH603527A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999877A patent/CH603526A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999777A patent/CH603525A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999477A patent/CH613932A5/xx not_active IP Right Cessation
- 1974-09-11 CH CH999577A patent/CH603543A5/xx not_active IP Right Cessation
- 1974-09-11 BE BE148417A patent/BE819794A/xx active Protection Beyond IP Right Term
- 1974-09-11 CH CH1236974A patent/CH599090A5/xx not_active IP Right Cessation
- 1974-09-11 NL NLAANVRAGE7412060,A patent/NL175812C/xx not_active IP Right Cessation
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1979
- 1979-08-23 SE SE7907064A patent/SE7907064L/sv unknown
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1980
- 1980-09-06 KE KE3081A patent/KE3081A/xx unknown
- 1980-09-06 KE KE3082A patent/KE3082A/xx unknown
- 1980-10-02 HK HK561/80A patent/HK56180A/xx unknown
- 1980-10-02 HK HK562/80A patent/HK56280A/xx unknown
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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 JP57190680A patent/JPS5921850B2/ja not_active Expired
- 1982-10-29 JP JP57190679A patent/JPS6033818B2/ja not_active Expired
- 1982-10-29 JP JP57190681A patent/JPS605580B2/ja not_active Expired
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