CS205049B2 - Method of preparing substituted 4-/2-benzofuranyl/-1,2,3,6-tetrahydropyridine - Google Patents
Method of preparing substituted 4-/2-benzofuranyl/-1,2,3,6-tetrahydropyridine Download PDFInfo
- Publication number
- CS205049B2 CS205049B2 CS767637A CS763776A CS205049B2 CS 205049 B2 CS205049 B2 CS 205049B2 CS 767637 A CS767637 A CS 767637A CS 763776 A CS763776 A CS 763776A CS 205049 B2 CS205049 B2 CS 205049B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- benzofuranyl
- bromo
- compound
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- WRPWAHAJKLEKPZ-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-1,2,3,6-tetrahydropyridine Chemical class C1NCCC(C=2OC3=CC=CC=C3C=2)=C1 WRPWAHAJKLEKPZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 6
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract description 2
- 108010062431 Monoamine oxidase Proteins 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- WZXHSWVDAYOFPE-UHFFFAOYSA-N brofaromine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1CCNCC1 WZXHSWVDAYOFPE-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000006965 reversible inhibition Effects 0.000 abstract 1
- 238000003797 solvolysis reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- WKUCLUMAURVHBQ-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)pyridine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1=CC=NC=C1 WKUCLUMAURVHBQ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- -1 7-bromo-5-methoxy-2-benzofuranyl Chemical group 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RTNSSJWVRPIISI-UHFFFAOYSA-M 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methylpyridin-1-ium;iodide Chemical compound [I-].C=1C2=CC(OC)=CC(Br)=C2OC=1C1=CC=[N+](C)C=C1 RTNSSJWVRPIISI-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- BSLKYCQDKAAGGV-UHFFFAOYSA-N 3-bromo-2-hydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(Br)=C(O)C(C=O)=C1 BSLKYCQDKAAGGV-UHFFFAOYSA-N 0.000 description 1
- VJXBMRMOGQEDKB-UHFFFAOYSA-N 3-bromo-5-methoxy-2-(pyridin-4-ylmethoxy)benzaldehyde Chemical compound N1=CC=C(C=C1)COC1=C(C=O)C=C(C=C1Br)OC VJXBMRMOGQEDKB-UHFFFAOYSA-N 0.000 description 1
- MAKLWNAYDCEBJB-UHFFFAOYSA-N 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methyl-3,6-dihydro-2h-pyridine Chemical compound C=1C2=CC(OC)=CC(Br)=C2OC=1C1=CCN(C)CC1 MAKLWNAYDCEBJB-UHFFFAOYSA-N 0.000 description 1
- KRLKXOLFFQWKPZ-UHFFFAOYSA-N 4-(bromomethyl)pyridine Chemical compound BrCC1=CC=NC=C1 KRLKXOLFFQWKPZ-UHFFFAOYSA-N 0.000 description 1
- WZIYCIBURCPKAR-UHFFFAOYSA-N 4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC=C1 WZIYCIBURCPKAR-UHFFFAOYSA-N 0.000 description 1
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 201000003102 mental depression Diseases 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000012154 norepinephrine uptake Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1530175A CH609054A5 (en) | 1975-11-26 | 1975-11-26 | Process for the preparation of a novel piperidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS205049B2 true CS205049B2 (en) | 1981-04-30 |
Family
ID=4407989
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS767637A CS205049B2 (en) | 1975-11-26 | 1976-11-25 | Method of preparing substituted 4-/2-benzofuranyl/-1,2,3,6-tetrahydropyridine |
| CS767637A CS205050B2 (en) | 1975-11-26 | 1976-11-25 | Method of preparing 4-/7-brom-5-methoxy-2-benzofuranyl/-1-methylpiperidine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS767637A CS205050B2 (en) | 1975-11-26 | 1976-11-25 | Method of preparing 4-/7-brom-5-methoxy-2-benzofuranyl/-1-methylpiperidine |
Country Status (23)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006524A1 (de) | 1978-06-22 | 1980-01-09 | Ciba-Geigy Ag | Neue Tetrahydropyridin- und Piperidinderivate und deren Säureadditionssalze, Verfahren zu deren Herstellung und solche enthaltende pharmazeutische Zusammensetzungen |
| US5455254A (en) * | 1991-02-15 | 1995-10-03 | Mondadori; Cesare | Substituted benzofuranylpiperidine as a nootropic agent |
| RU2095339C1 (ru) * | 1991-10-17 | 1997-11-10 | Циба-Гейги АГ | Производные гидрохинона в свободном виде или в виде соли, способы их получения, производные пиперидина и способы их получения |
| US5693807A (en) * | 1992-10-14 | 1997-12-02 | Ciba-Geigy Corporation | Substituted hydroquinone derivatives |
| ATE180780T1 (de) * | 1993-08-05 | 1999-06-15 | Hoechst Marion Roussel Inc | 2-(piperidin-4-yl, pyridin-4-yl und tetrahydropyridin-4-yl)-benzofuran-7-carbamat derivate, ihre herstellung und verwendung als acetylcholinesterase inhibitoren |
| CN101810606A (zh) * | 2010-03-12 | 2010-08-25 | 南方医科大学 | 2-(6-羟基-2′,3′-二甲氧基苯基)-6-羟基-7-甲氧基苯骈呋喃在制备单胺氧化酶抑制剂中的应用 |
| US8796306B2 (en) | 2010-06-23 | 2014-08-05 | Sumitomo Chemical Company, Limited | Noxious arthropod controlling composition and heterocyclic compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH592656A5 (enrdf_load_stackoverflow) * | 1973-03-02 | 1977-10-31 | Ciba Geigy Ag | |
| IE39264B1 (en) * | 1973-05-25 | 1978-08-30 | Ciba Geigy Ag | New pharmaceutical preparations |
-
1975
- 1975-11-26 CH CH1530175A patent/CH609054A5/xx not_active IP Right Cessation
-
1976
- 1976-11-22 AR AR265561A patent/AR214985A1/es active
- 1976-11-23 GB GB48763/76A patent/GB1565055A/en not_active Expired
- 1976-11-23 NL NL7613050A patent/NL7613050A/xx not_active Application Discontinuation
- 1976-11-23 DE DE19762653147 patent/DE2653147A1/de active Granted
- 1976-11-23 CY CY1179A patent/CY1179A/xx unknown
- 1976-11-24 DD DD7600195944A patent/DD129328A6/xx unknown
- 1976-11-24 CA CA266,466A patent/CA1088940A/en not_active Expired
- 1976-11-24 FR FR7635373A patent/FR2332754A2/fr active Granted
- 1976-11-24 ES ES453582A patent/ES453582A2/es not_active Expired
- 1976-11-25 AT AT874476A patent/AT352728B/de not_active IP Right Cessation
- 1976-11-25 NZ NZ182716A patent/NZ182716A/xx unknown
- 1976-11-25 CS CS767637A patent/CS205049B2/cs unknown
- 1976-11-25 IE IE2588/76A patent/IE44084B1/en unknown
- 1976-11-25 DK DK532176A patent/DK142987C/da active
- 1976-11-25 ZA ZA00777068A patent/ZA777068B/xx unknown
- 1976-11-25 SU SU762422953A patent/SU679136A3/ru active
- 1976-11-25 CS CS767637A patent/CS205050B2/cs unknown
- 1976-11-25 AU AU19995/76A patent/AU507722B2/en not_active Expired
- 1976-11-25 SE SE7613193A patent/SE426826B/xx not_active IP Right Cessation
- 1976-11-25 BE BE172674A patent/BE848720R/xx not_active IP Right Cessation
- 1976-11-26 JP JP51141389A patent/JPS5265277A/ja active Granted
-
1978
- 1978-04-17 SU SU782602552A patent/SU680648A3/ru active
- 1978-04-17 SU SU782602551A patent/SU682132A3/ru active
-
1983
- 1983-05-19 HK HK167/83A patent/HK16783A/xx unknown
-
1984
- 1984-12-30 MY MY93/84A patent/MY8400093A/xx unknown
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