DE2460527A1 - Neue organische verbindungen und verfahren zu deren herstellung - Google Patents
Neue organische verbindungen und verfahren zu deren herstellungInfo
- Publication number
- DE2460527A1 DE2460527A1 DE19742460527 DE2460527A DE2460527A1 DE 2460527 A1 DE2460527 A1 DE 2460527A1 DE 19742460527 DE19742460527 DE 19742460527 DE 2460527 A DE2460527 A DE 2460527A DE 2460527 A1 DE2460527 A1 DE 2460527A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrogen
- compounds
- chlorine
- fluorine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Chemical group 0.000 claims description 18
- 229910052801 chlorine Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- -1 methylenedioxy group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- BYLPZVAKOZYZPH-UHFFFAOYSA-N imidazo[2,1-a]isoquinoline Chemical class C1=CC=C2C3=NC=CN3C=CC2=C1 BYLPZVAKOZYZPH-UHFFFAOYSA-N 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- ZNWOXGIEIAGCQA-UHFFFAOYSA-N 2-(2-methylphenyl)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC=C1C1=NCCN1 ZNWOXGIEIAGCQA-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- OYHRTIFEWIRHKM-UHFFFAOYSA-N 5-(4-chlorophenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1C2=CC=CC=C2C2=NCCN2C1(O)C1=CC=C(Cl)C=C1 OYHRTIFEWIRHKM-UHFFFAOYSA-N 0.000 description 2
- ASAXCWFAAMUWMC-UHFFFAOYSA-N 5-(4-fluorophenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1C2=CC=CC=C2C2=NCCN2C1(O)C1=CC=C(F)C=C1 ASAXCWFAAMUWMC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940005513 antidepressants Drugs 0.000 description 2
- UMPRJGKLMUDRHL-UHFFFAOYSA-N ethyl 4-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1 UMPRJGKLMUDRHL-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- CSNXUYRHPXGSJD-UHFFFAOYSA-N isoquinolin-5-ol Chemical compound N1=CC=C2C(O)=CC=CC2=C1 CSNXUYRHPXGSJD-UHFFFAOYSA-N 0.000 description 2
- LXNFVVDCCWUUKC-UHFFFAOYSA-N methyl 4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1 LXNFVVDCCWUUKC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229960003147 reserpine Drugs 0.000 description 2
- 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 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- BPDHWJWTERFDRD-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC(C)=CC=C1C1=NCCN1 BPDHWJWTERFDRD-UHFFFAOYSA-N 0.000 description 1
- KRDOZBINVYHCDI-UHFFFAOYSA-N 2-(5-chloro-2-methylphenyl)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=C(Cl)C=C1C1=NCCN1 KRDOZBINVYHCDI-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- VTMGLOBDVHRQIR-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1=C2OCOC2=CC(C2(N3CCN=C3C3=CC=CC=C3C2)O)=C1 VTMGLOBDVHRQIR-UHFFFAOYSA-N 0.000 description 1
- MRYHNERJCXUYSM-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1C2=CC=CC=C2C2=NCCN2C1(O)C1=CC=C(Cl)C=C1Cl MRYHNERJCXUYSM-UHFFFAOYSA-N 0.000 description 1
- UHCJZTKRADXJBR-UHFFFAOYSA-N 5-(2-chlorophenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1C2=CC=CC=C2C2=NCCN2C1(O)C1=CC=CC=C1Cl UHCJZTKRADXJBR-UHFFFAOYSA-N 0.000 description 1
- HQRRHGZAZVWSPF-UHFFFAOYSA-N 5-(3-fluorophenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1C2=CC=CC=C2C2=NCCN2C1(O)C1=CC=CC(F)=C1 HQRRHGZAZVWSPF-UHFFFAOYSA-N 0.000 description 1
- JAHZSXVGNHTXMR-UHFFFAOYSA-N 5-(4-methoxyphenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1=CC(OC)=CC=C1C1(O)N2CCN=C2C2=CC=CC=C2C1 JAHZSXVGNHTXMR-UHFFFAOYSA-N 0.000 description 1
- FWCVCAUHZGOSNT-UHFFFAOYSA-N 5-(4-methylphenyl)-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1=CC(C)=CC=C1C1(O)N2CCN=C2C2=CC=CC=C2C1 FWCVCAUHZGOSNT-UHFFFAOYSA-N 0.000 description 1
- YEQDDLZHZCNPFQ-UHFFFAOYSA-N 5-phenyl-3,6-dihydro-2h-imidazo[2,1-a]isoquinolin-5-ol Chemical compound C1C2=CC=CC=C2C2=NCCN2C1(O)C1=CC=CC=C1 YEQDDLZHZCNPFQ-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZBBGAUHWTZKKQQ-UHFFFAOYSA-N ethyl 2,4-dichlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1Cl ZBBGAUHWTZKKQQ-UHFFFAOYSA-N 0.000 description 1
- RETLCWPMLJPOTP-UHFFFAOYSA-N ethyl 2-chlorobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1Cl RETLCWPMLJPOTP-UHFFFAOYSA-N 0.000 description 1
- YONQPSPHUKKUEJ-UHFFFAOYSA-N ethyl 3,4-dichlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(Cl)=C1 YONQPSPHUKKUEJ-UHFFFAOYSA-N 0.000 description 1
- ZQDADDSPMCHZPX-UHFFFAOYSA-N ethyl 4-(trifluoromethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(C(F)(F)F)C=C1 ZQDADDSPMCHZPX-UHFFFAOYSA-N 0.000 description 1
- NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42952674A | 1974-01-02 | 1974-01-02 | |
| US05/520,537 US4101553A (en) | 1974-01-02 | 1974-11-04 | Imidazo[2,1-a]isoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2460527A1 true DE2460527A1 (de) | 1975-07-10 |
Family
ID=27028230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742460527 Pending DE2460527A1 (de) | 1974-01-02 | 1974-12-20 | Neue organische verbindungen und verfahren zu deren herstellung |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS50105698A (en:Method) |
| AU (1) | AU7703574A (en:Method) |
| DD (1) | DD116235A5 (en:Method) |
| DE (1) | DE2460527A1 (en:Method) |
| DK (1) | DK683374A (en:Method) |
| FI (1) | FI370674A7 (en:Method) |
| FR (1) | FR2255907A1 (en:Method) |
| IL (1) | IL46370A0 (en:Method) |
| NL (1) | NL7416999A (en:Method) |
| NO (1) | NO744667L (en:Method) |
| SE (1) | SE7416301L (en:Method) |
| YU (1) | YU351974A (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI753070A7 (en:Method) * | 1974-11-12 | 1976-05-13 | Sandoz Ag | |
| PH15001A (en) * | 1977-07-25 | 1982-03-22 | Sandoz Ag | Prolactin secretion inhibitors |
| DE2853409A1 (de) * | 1977-12-20 | 1979-06-21 | Sandoz Ag | Anti-parkinson zusammensetzungen |
-
1974
- 1974-12-20 FI FI3706/74A patent/FI370674A7/fi unknown
- 1974-12-20 DE DE19742460527 patent/DE2460527A1/de active Pending
- 1974-12-23 NO NO744667A patent/NO744667L/no unknown
- 1974-12-27 JP JP49149104A patent/JPS50105698A/ja active Pending
- 1974-12-27 DK DK683374A patent/DK683374A/da unknown
- 1974-12-27 SE SE7416301A patent/SE7416301L/xx unknown
- 1974-12-30 NL NL7416999A patent/NL7416999A/xx unknown
- 1974-12-30 YU YU03519/74A patent/YU351974A/xx unknown
- 1974-12-31 AU AU77035/74A patent/AU7703574A/en not_active Expired
- 1974-12-31 IL IL46370A patent/IL46370A0/xx unknown
-
1975
- 1975-01-02 FR FR7500029A patent/FR2255907A1/fr not_active Withdrawn
- 1975-01-02 DD DD183475A patent/DD116235A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO744667L (en:Method) | 1975-07-28 |
| AU7703574A (en) | 1976-07-01 |
| JPS50105698A (en:Method) | 1975-08-20 |
| FR2255907A1 (en) | 1975-07-25 |
| NL7416999A (nl) | 1975-07-04 |
| DK683374A (en:Method) | 1975-09-01 |
| YU351974A (en) | 1982-05-31 |
| IL46370A0 (en) | 1975-08-31 |
| FI370674A7 (en:Method) | 1975-07-03 |
| SE7416301L (en:Method) | 1975-07-03 |
| DD116235A5 (en:Method) | 1975-11-12 |
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