NO744175L - - Google Patents
Info
- Publication number
- NO744175L NO744175L NO744175A NO744175A NO744175L NO 744175 L NO744175 L NO 744175L NO 744175 A NO744175 A NO 744175A NO 744175 A NO744175 A NO 744175A NO 744175 L NO744175 L NO 744175L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- acid
- compounds
- dihydro
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SUXLVXOMPKZBOV-CXAGYDPISA-N (6ar,9r)-n,n-diethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](NC[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 SUXLVXOMPKZBOV-CXAGYDPISA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- -1 caustic soda Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 1
- 229960004704 dihydroergotamine Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- FSIZNIXUPRQTLZ-QMTHXVAHSA-N lysergic acid Chemical class C1=CC=C2C3=C[C@@H](C(O)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 FSIZNIXUPRQTLZ-QMTHXVAHSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ORIBUSCBDFDAIQ-GYYYEOQOSA-N methyl (6ar,9r)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C2[C@H](NC[C@@H](C2)C(=O)OC)C2)=C3C2=CNC3=C1 ORIBUSCBDFDAIQ-GYYYEOQOSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
- 229930015720 peptide alkaloid Natural products 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 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
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1669873A CH587858A5 (ru) | 1973-11-28 | 1973-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO744175L true NO744175L (ru) | 1975-06-23 |
Family
ID=4419482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO744175A NO744175L (ru) | 1973-11-28 | 1974-11-20 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4229451A (ru) |
| JP (1) | JPS5919116B2 (ru) |
| AT (1) | AT352911B (ru) |
| BE (1) | BE822729A (ru) |
| CA (1) | CA1034572A (ru) |
| CH (1) | CH587858A5 (ru) |
| CS (1) | CS176291B2 (ru) |
| DD (1) | DD115119A5 (ru) |
| DE (1) | DE2454619A1 (ru) |
| DK (1) | DK143804C (ru) |
| ES (1) | ES432288A1 (ru) |
| FI (1) | FI59254C (ru) |
| FR (2) | FR2252098B1 (ru) |
| GB (2) | GB1496491A (ru) |
| HK (1) | HK54080A (ru) |
| HU (1) | HU168859B (ru) |
| IE (1) | IE41767B1 (ru) |
| IL (1) | IL46128A (ru) |
| MY (1) | MY8100185A (ru) |
| NL (1) | NL7415250A (ru) |
| NO (1) | NO744175L (ru) |
| PH (1) | PH13669A (ru) |
| SE (2) | SE417319B (ru) |
| SU (1) | SU516355A3 (ru) |
| ZA (1) | ZA747603B (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH601321A5 (ru) * | 1975-01-06 | 1978-07-14 | Sandoz Ag | |
| CH619468A5 (ru) * | 1976-01-12 | 1980-09-30 | Sandoz Ag | |
| DE3020895A1 (de) * | 1979-06-12 | 1980-12-18 | Sandoz Ag | Ergopeptinderivate, verfahren zu deren herstellung sowie diese ergopeptinderivate enthaltende pharmazeutischen zusammensetzungen |
| US5069911A (en) * | 1985-02-05 | 1991-12-03 | Sandoz Ltd. | Pharmaceutical 9,10-dihydrogenated ergot alkaloid containing compositions |
| US7771746B2 (en) * | 1999-12-03 | 2010-08-10 | Polichem Sa | Methods for making sustained-release pharmaceutical compositions of ergot alkaloids having improved bioavailability and compositions thereof |
| GB0409785D0 (en) * | 2004-04-30 | 2004-06-09 | Resolution Chemicals Ltd | Preparation of cabergoline |
| US7339060B2 (en) | 2005-03-23 | 2008-03-04 | Resolution Chemicals, Ltd. | Preparation of cabergoline |
| GB0505965D0 (en) * | 2005-03-23 | 2005-04-27 | Resolution Chemicals Ltd | Preparation of cabergoline |
| US20070197576A1 (en) * | 2006-02-08 | 2007-08-23 | Resolution Chemicals Limited | Production of Cabergoline and Novel Polymorphic Form Thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619488A (en) * | 1952-11-25 | Method of preparing d | ||
| GB769260A (en) * | 1954-04-07 | 1957-03-06 | Sandoz Ltd | Process for the preparation of isomeric racemic dihydrolysergic acids and their homologues |
| DE1006425B (de) * | 1954-04-07 | 1957-04-18 | Sandoz Ag | Verfahren zur Herstellung der isomeren racemischen Dihydrolysergsaeuren und ihren Homologen |
| GB1011112A (en) * | 1961-05-10 | 1965-11-24 | Sandoz Ag | Improvements in or relating to ergot alkaloids |
| CH469006A (de) * | 1965-07-07 | 1969-02-28 | Sandoz Ag | Verfahren zur Herstellung neuer synthetischer Alkaloide |
| CH469735A (de) * | 1965-11-02 | 1969-03-15 | Sandoz Ag | Verfahren zur Herstellung heterocyclischer Verbindungen |
| GB1298277A (en) * | 1969-04-18 | 1972-11-29 | Sandoz Ltd | Preparation of ergot peptide alkaloids |
| CH534683A (de) * | 1970-05-26 | 1973-03-15 | Sandoz Ag | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| CH601321A5 (ru) * | 1975-01-06 | 1978-07-14 | Sandoz Ag | |
| US4138565A (en) * | 1975-05-31 | 1979-02-06 | Sandoz Ltd. | Stable solutions and processes for their preparation |
-
1973
- 1973-11-28 CH CH1669873A patent/CH587858A5/xx not_active IP Right Cessation
-
1974
- 1974-11-18 DE DE19742454619 patent/DE2454619A1/de not_active Withdrawn
- 1974-11-19 DK DK600374A patent/DK143804C/da not_active IP Right Cessation
- 1974-11-19 FI FI3345/74A patent/FI59254C/fi active
- 1974-11-20 NO NO744175A patent/NO744175L/no unknown
- 1974-11-20 SE SE7414607A patent/SE417319B/xx unknown
- 1974-11-22 NL NL7415250A patent/NL7415250A/xx not_active Application Discontinuation
- 1974-11-25 GB GB50914/74A patent/GB1496491A/en not_active Expired
- 1974-11-25 GB GB23690/77A patent/GB1496492A/en not_active Expired
- 1974-11-26 IE IE2432/74A patent/IE41767B1/en unknown
- 1974-11-26 AT AT945174A patent/AT352911B/de not_active IP Right Cessation
- 1974-11-26 HU HUSA2719A patent/HU168859B/hu unknown
- 1974-11-26 PH PH16563A patent/PH13669A/en unknown
- 1974-11-26 ES ES432288A patent/ES432288A1/es not_active Expired
- 1974-11-26 DD DD182581A patent/DD115119A5/xx unknown
- 1974-11-26 CS CS8081A patent/CS176291B2/cs unknown
- 1974-11-26 IL IL46128A patent/IL46128A/en unknown
- 1974-11-27 CA CA214,716A patent/CA1034572A/en not_active Expired
- 1974-11-27 JP JP49135657A patent/JPS5919116B2/ja not_active Expired
- 1974-11-28 ZA ZA00747603A patent/ZA747603B/xx unknown
- 1974-11-28 SU SU2082566A patent/SU516355A3/ru active
- 1974-11-28 FR FR7439049A patent/FR2252098B1/fr not_active Expired
- 1974-11-28 BE BE150971A patent/BE822729A/xx not_active IP Right Cessation
-
1977
- 1977-01-31 FR FR7702636A patent/FR2334681A1/fr active Granted
- 1977-09-16 SE SE7710418A patent/SE424869B/xx unknown
-
1978
- 1978-06-29 US US05/920,480 patent/US4229451A/en not_active Expired - Lifetime
-
1980
- 1980-09-25 HK HK540/80A patent/HK54080A/xx unknown
-
1981
- 1981-12-30 MY MY185/81A patent/MY8100185A/xx unknown
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