KR840000514A - 벤조일- 페닐- 피페리딘 유도체의 제법 - Google Patents
벤조일- 페닐- 피페리딘 유도체의 제법 Download PDFInfo
- Publication number
- KR840000514A KR840000514A KR1019820002891A KR820002891A KR840000514A KR 840000514 A KR840000514 A KR 840000514A KR 1019820002891 A KR1019820002891 A KR 1019820002891A KR 820002891 A KR820002891 A KR 820002891A KR 840000514 A KR840000514 A KR 840000514A
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- KR
- South Korea
- Prior art keywords
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- compound
- different
- same
- alkyl group
- Prior art date
Links
- PLDZBWIWZXXVPV-UHFFFAOYSA-N phenyl-(1-phenylpiperidin-2-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1CCCCN1C1=CC=CC=C1 PLDZBWIWZXXVPV-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 229910004013 NO 2 Inorganic materials 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000009615 deamination Effects 0.000 claims 1
- 238000006481 deamination reaction Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- AYMIERIHYPLRIR-UHFFFAOYSA-N phenyl-(2-piperidin-1-ylphenyl)methanone Chemical class C=1C=CC=C(N2CCCCC2)C=1C(=O)C1=CC=CC=C1 AYMIERIHYPLRIR-UHFFFAOYSA-N 0.000 claims 1
- 235000010289 potassium nitrite Nutrition 0.000 claims 1
- 239000004304 potassium nitrite Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D295/04—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
- C07D295/12—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 or doubly bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D295/04—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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- ⅰ) 하기식(Ⅲ)의 2-할로게노-5-니트로-벤조페놀을 하기식(Ⅱ)의 치환 피리딘과 반응시켜 하기식(I0)의 니트로 화합물을 얻고, ⅱ) 상기에서 수득된 화합물(I0)의 니트로기를 아미노기로 환원시켜 R4=NH2인 식(Ⅰ)의 아미노 유도체를 얻은 다음, 상기 아미노 유도체를 탈아미노기, 알킬화 또는 아미노기를 할로겐기로 전환시키는 반응을 시킴을 특징으로 하는 하기식(Ⅰ)의 2-피페리디노벤조페논류로 구성된 군으로부터 선택된 신규벤조일-페닐-피페리딘 유도체 및 그의 산부가염의 제조방법.상기 식에서;-R1,R2및 R3는 동일 또는 상이한데, 각각 수소원자, 히드록시기, CF3, 할로겐, 저급알킬기 또는 저급알콕시기이고; -R4는 수소원자, 할로겐, NO2기, NR'R"기[여기서, R' 및 R"는 동일 또는 상이하며, 수소원자, 저급알킬기 또는 CO2R기(R은 저급알킬기 또는 벤질기를 나타냄)]이고; -R5및 R6는 동일 또는 상이하며 각각 수소원자, 저급알킬기, OH기, 페닐기 또는 벤질기이고; -X는 할로겐원자(바람직하기는 Cl 또는 F)이다.
- 제1항에 있어서, 반응단계 ⅰ) 이 화합물(Ⅲ) 1.1몰 대 화합물(Ⅱ) 1몰 비율로 15℃ 내지 반응 매질의 환류 온도사이의 온도에서 염기 존재하, 특히 방향족 탄화수소류, 에테르류 및 알코올류로 구성된 군으로부터 선택된 불활성 유기 용매중에서 수행됨을 특징으로 하는 방법.
- 제1항에 있어서, 니트로기의 환원반응 단계 ⅱ)가 15℃ 내지 반응 매질의 환류온도 사이의 온도에서철 및 산존재하, 특히 알코올 및 알코올-물의 혼합물로 이루어진 군으로부터 선택된 불활성 유기용매 중에서 행해짐을 특징으로하는 방법.
- 제1항에 있어서 0℃에서 아질산나트륨 또는 아질산 칼륨으로 상기 아미노기를 디아조화시킨 다음, 생성된 디아조늄기를 수소원자, 할로겐원자 또는 CF3기로 공지의 메카니즘에 따라 치환시킴으로써 아미노기의 탈아미노 기화 단계 ⅱ)가 행해짐을 특징으로 하는 방법.
- 제1항에 있어서, -R1,R2및 R3가 동일 또는 상이하며 각각 H,F, Cl,Br,OH,CF3,C1~C4-알킬기 또는 C1~C4-알콕시기이며; -R4는 H,Cl,Br,F 또는 NR'R"[여기서, R' 및 R"는 동일 또는 상이하며, H,C1~C4-알킬기 또는 CO2R기(여기서, R은 C1~C4-알킬기 또는 벤질기임)을 나타냄]이고; -R5및 R6는 동일 또는 상이하며 각각 H, C1~C4알킬기, OH기, 페닐기 또는 벤질기임을 특징으로 하는방법.
- 제1항에 있어서, -R1,R2및 R3가 동일 또는 상이하며 각각 H,F,Cl,Br,OH,CF3,C1~C4-알킬기 또는 C1~C4-알콕시기를 나타내며; -R4는 H,Cl,Br,F,NO2또는 NR'R"[여기서, R' 및 R"는 동일 또는 상이하며 H,C1~C|4-알킬기 또는 CO2R기(여기서, R은 C1~C4-알킬기 또는 벤질기임)을 나타냄]기이며; -R5및 R6는 동일 또는 상이하며 각각 H,C1~C4알킬기, OH기, 페닐기 또는 벤질기를 나타내고; -R1,R2,R3,R4,R5및 R6은 하기 2가지 조선(A) 및 (B)[(A)-R1,R2,R3,R4,R5및 R6중의 하나 이상은 수소가 아님 (B) R1=R2=R3=R5=R6=H인 경우 R4는 NO2가 아님]중 하나 이상의 조건에 따라야 함을 특징으로 하는 방법.
- 제1 또는 2항에 있어서, R1=4-Cl; R=NO2; R5=4-CH3; 그리고 R2=R5=R6=H인 방법.
- 제1 또는 3항에 있어서, R1=4-Cl; R4=NH2; R5=4-CH3; 그리고 R2=R3=R6=H인 방법.
- 제1 또는 3항에 있어서, R1=4-Cl; R4=NH2; R5=3-CH3; 그리고 R2=R3=R6=H인 방법.
- 제1 또는 3항에 있어서, R1=4-Cl; R4=NH2; R5=2-CH3; 그리고 R2=R3=R6=H인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8112745A FR2508445A1 (fr) | 1981-06-29 | 1981-06-29 | Nouveaux derives de benzoyl-phenyl-piperidine, leur procede de preparation et leur application, notamment en therapeutique |
| FR8112745 | 1981-06-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840000514A true KR840000514A (ko) | 1984-02-22 |
| KR880001298B1 KR880001298B1 (ko) | 1988-07-22 |
Family
ID=9259970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8202891A KR880001298B1 (ko) | 1981-06-29 | 1982-06-29 | 벤조일-페닐-피페리딘 유도체의 제법 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4528294A (ko) |
| EP (1) | EP0069012B1 (ko) |
| JP (1) | JPS588061A (ko) |
| KR (1) | KR880001298B1 (ko) |
| AR (1) | AR230048A1 (ko) |
| AT (1) | ATE9795T1 (ko) |
| AU (1) | AU550320B2 (ko) |
| CA (1) | CA1187501A (ko) |
| CS (1) | CS235542B2 (ko) |
| DD (1) | DD202557A5 (ko) |
| DE (1) | DE3260949D1 (ko) |
| DK (1) | DK152668C (ko) |
| ES (1) | ES8304936A1 (ko) |
| FI (1) | FI77447C (ko) |
| FR (1) | FR2508445A1 (ko) |
| GR (1) | GR76401B (ko) |
| HU (1) | HU189150B (ko) |
| IE (1) | IE53189B1 (ko) |
| IL (2) | IL66123A (ko) |
| NO (1) | NO160136C (ko) |
| OA (1) | OA07133A (ko) |
| PH (1) | PH17368A (ko) |
| PT (1) | PT75135B (ko) |
| SU (1) | SU1147251A3 (ko) |
| YU (1) | YU43799B (ko) |
| ZA (1) | ZA824536B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL82573A0 (en) * | 1986-05-30 | 1987-11-30 | Sori Soc Rech Ind | Preparation of benzoylphenyl-piperidine derivatives |
| FR2620027A1 (fr) * | 1987-09-09 | 1989-03-10 | Fournier Innovation Synergie | Nouvelle utilisation de la (5-amino-2-(4-methyl-1-piperidinyl)phenyl)-(4-chlorophenyl)-methanone |
| WO2000071519A2 (en) * | 1999-05-21 | 2000-11-30 | Eli Lilly And Company | Immunopotentiator agents |
| JP2003528830A (ja) * | 2000-03-10 | 2003-09-30 | ファルマシア・コーポレーション | テトラヒドロベンゾチエピン類の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3202655A (en) * | 1962-04-27 | 1965-08-24 | Yvon G Perron | 6-[alpha-substituted-alpha-(2-or 3-heterocyclic) acetamido] penicillanic acid and nontoxic salts thereof |
| BE637329A (ko) * | 1962-11-13 | |||
| FR1375300A (fr) * | 1962-11-13 | 1964-10-16 | Hoffmann La Roche | Dérivés de benzophénone et leur préparation |
| FR1403939A (fr) * | 1963-06-07 | 1965-06-25 | Hoffmann La Roche | Procédé pour la préparation de dérivés de benzodiazépine |
| FR1526708A (fr) * | 1966-06-13 | 1968-05-24 | Upjohn Co | 1.3-amino-alcools, leurs intermédiaires et dérivés et leur procédé de préparation |
| US3668199A (en) * | 1966-06-13 | 1972-06-06 | Upjohn Co | 1,3-aminoalcohols |
| FR1530393A (fr) * | 1966-07-11 | 1968-06-21 | Hoffmann La Roche | Procédé pour la préparation de dérivés de pipéridine |
| IE34545B1 (en) * | 1969-10-01 | 1975-06-11 | Continental Pharma | Amino-alcohols,their salts and process for preparing the same |
| HU167950B (ko) * | 1973-07-26 | 1976-01-28 | ||
| HU167949B (ko) * | 1973-07-26 | 1976-01-28 | ||
| US4064121A (en) * | 1973-07-26 | 1977-12-20 | Richter Gedeon Vegyeszeti Gyar Rt. | Substituted nitrobenzophenone derivatives and a process for the preparation thereof |
| US4021563A (en) * | 1975-02-06 | 1977-05-03 | Sven Eric Harry Hernestam | Method of treating cardiac arrhythmia with γ-piperidino-butyrophenones |
| IE49998B1 (en) * | 1979-08-06 | 1986-01-22 | Merrell Dow Pharma | 4-(naphthalenyloxy)piperidine derivatives |
-
1981
- 1981-06-29 FR FR8112745A patent/FR2508445A1/fr active Granted
-
1982
- 1982-06-21 FI FI822215A patent/FI77447C/fi not_active IP Right Cessation
- 1982-06-21 GR GR68497A patent/GR76401B/el unknown
- 1982-06-22 IE IE1475/82A patent/IE53189B1/en not_active IP Right Cessation
- 1982-06-23 DE DE8282401154T patent/DE3260949D1/de not_active Expired
- 1982-06-23 AT AT82401154T patent/ATE9795T1/de active
- 1982-06-23 EP EP82401154A patent/EP0069012B1/fr not_active Expired
- 1982-06-24 IL IL66123A patent/IL66123A/xx unknown
- 1982-06-24 US US06/391,915 patent/US4528294A/en not_active Expired - Fee Related
- 1982-06-25 ZA ZA824536A patent/ZA824536B/xx unknown
- 1982-06-28 ES ES513565A patent/ES8304936A1/es not_active Expired
- 1982-06-28 PT PT75135A patent/PT75135B/pt not_active IP Right Cessation
- 1982-06-28 NO NO822185A patent/NO160136C/no unknown
- 1982-06-28 AR AR289803A patent/AR230048A1/es active
- 1982-06-28 SU SU823456997A patent/SU1147251A3/ru active
- 1982-06-28 HU HU822088A patent/HU189150B/hu not_active IP Right Cessation
- 1982-06-28 DK DK289382A patent/DK152668C/da not_active IP Right Cessation
- 1982-06-29 DD DD82241202A patent/DD202557A5/de not_active IP Right Cessation
- 1982-06-29 YU YU1415/82A patent/YU43799B/xx unknown
- 1982-06-29 CA CA000406296A patent/CA1187501A/en not_active Expired
- 1982-06-29 JP JP57110936A patent/JPS588061A/ja active Granted
- 1982-06-29 OA OA57724A patent/OA07133A/xx unknown
- 1982-06-29 AU AU85429/82A patent/AU550320B2/en not_active Ceased
- 1982-06-29 KR KR8202891A patent/KR880001298B1/ko not_active IP Right Cessation
- 1982-06-29 CS CS824905A patent/CS235542B2/cs unknown
- 1982-06-29 PH PH27508A patent/PH17368A/en unknown
-
1985
- 1985-09-04 IL IL8576287A patent/IL76287A0/xx not_active IP Right Cessation
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1986
- 1986-05-30 US US06/868,443 patent/US4680402A/en not_active Expired - Fee Related
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