CA1097365A - Process for preparing 1-tertiary-alkyl-3-(substituted furyl)-urea antihypertensives - Google Patents
Process for preparing 1-tertiary-alkyl-3-(substituted furyl)-urea antihypertensivesInfo
- Publication number
- CA1097365A CA1097365A CA274,514A CA274514A CA1097365A CA 1097365 A CA1097365 A CA 1097365A CA 274514 A CA274514 A CA 274514A CA 1097365 A CA1097365 A CA 1097365A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- furanone
- urea
- alkyl
- tertiary
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 239000004202 carbamide Substances 0.000 title abstract description 19
- 125000002541 furyl group Chemical group 0.000 title abstract description 4
- 229940030600 antihypertensive agent Drugs 0.000 title abstract 2
- 239000002220 antihypertensive agent Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- -1 tert-amyl Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229940067157 phenylhydrazine Drugs 0.000 abstract description 8
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract description 6
- 239000012948 isocyanate Substances 0.000 abstract description 4
- SABBJFPNIAIRGR-UHFFFAOYSA-N 3-amino-2h-furan-5-one Chemical compound NC1=CC(=O)OC1 SABBJFPNIAIRGR-UHFFFAOYSA-N 0.000 abstract description 3
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 abstract description 3
- XVXRHJRJIGTRIF-UHFFFAOYSA-N 3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound O=C1OCC(NNC=2C=CC=CC=2)=C1 XVXRHJRJIGTRIF-UHFFFAOYSA-N 0.000 abstract description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 2
- XYYGVTGRQFCJOF-UHFFFAOYSA-N 1-tert-butyl-3-(2-methyl-5-oxo-2h-furan-3-yl)urea Chemical compound CC1OC(=O)C=C1NC(=O)NC(C)(C)C XYYGVTGRQFCJOF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000013877 carbamide Nutrition 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- IXOOBJLFCYIKSF-UHFFFAOYSA-N 3-amino-2-methyl-2h-furan-5-one Chemical compound CC1OC(=O)C=C1N IXOOBJLFCYIKSF-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- WQPWMAYLHFRFPP-UHFFFAOYSA-N 2-ethyl-3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound CCC1OC(=O)C=C1NNC1=CC=CC=C1 WQPWMAYLHFRFPP-UHFFFAOYSA-N 0.000 description 3
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 3
- OPXIGKNSHMVEKG-UHFFFAOYSA-N 2-methyl-3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound CC1OC(=O)C=C1NNC1=CC=CC=C1 OPXIGKNSHMVEKG-UHFFFAOYSA-N 0.000 description 3
- QJDKEKAREQSWGS-UHFFFAOYSA-N 3-amino-4-methyl-2h-furan-5-one Chemical compound CC1=C(N)COC1=O QJDKEKAREQSWGS-UHFFFAOYSA-N 0.000 description 3
- VEJKNMIKSYFETD-UHFFFAOYSA-N 4-methyl-3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound C1OC(=O)C(C)=C1NNC1=CC=CC=C1 VEJKNMIKSYFETD-UHFFFAOYSA-N 0.000 description 3
- ZIQFRNVCLDSOAB-UHFFFAOYSA-N 5-methyloxolane-2,4-dione Chemical compound CC1OC(=O)CC1=O ZIQFRNVCLDSOAB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- AWGPWASAORSKKR-UHFFFAOYSA-N 3-methyloxolane-2,4-dione Chemical compound CC1C(=O)COC1=O AWGPWASAORSKKR-UHFFFAOYSA-N 0.000 description 2
- DZMHRWJWFDJBHD-UHFFFAOYSA-N 5-ethyloxolane-2,4-dione Chemical compound CCC1OC(=O)CC1=O DZMHRWJWFDJBHD-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- IAODRFIZLKITMK-UHFFFAOYSA-N furan-2,3-dione Chemical compound O=C1OC=CC1=O IAODRFIZLKITMK-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006894 reductive elimination reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- XTCXPTOMXXOPLA-UHFFFAOYSA-N 2-isocyanato-2-methylbutane Chemical compound CCC(C)(C)N=C=O XTCXPTOMXXOPLA-UHFFFAOYSA-N 0.000 description 1
- FOTOFVUOURYGNI-UHFFFAOYSA-N 3-amino-2-ethyl-2h-furan-5-one Chemical compound CCC1OC(=O)C=C1N FOTOFVUOURYGNI-UHFFFAOYSA-N 0.000 description 1
- FHSUFDYFOHSYHI-UHFFFAOYSA-N 3-oxopentanoic acid Chemical compound CCC(=O)CC(O)=O FHSUFDYFOHSYHI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 239000012044 organic layer 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
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67007876A | 1976-03-24 | 1976-03-24 | |
| US670,078 | 1976-03-24 | ||
| US76227377A | 1977-01-25 | 1977-01-25 | |
| US762,273 | 1977-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097365A true CA1097365A (en) | 1981-03-10 |
Family
ID=27100248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA274,514A Expired CA1097365A (en) | 1976-03-24 | 1977-03-22 | Process for preparing 1-tertiary-alkyl-3-(substituted furyl)-urea antihypertensives |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS52139056A (cs) |
| AR (1) | AR211956A1 (cs) |
| AT (1) | AT354460B (cs) |
| CA (1) | CA1097365A (cs) |
| CH (1) | CH626081A5 (cs) |
| DD (1) | DD130480A5 (cs) |
| DK (1) | DK143274C (cs) |
| ES (1) | ES457102A1 (cs) |
| FI (1) | FI770929A7 (cs) |
| GR (1) | GR62563B (cs) |
| HU (1) | HU173840B (cs) |
| LU (1) | LU77009A1 (cs) |
| NL (1) | NL7703155A (cs) |
| NO (1) | NO771021L (cs) |
| PT (1) | PT66336B (cs) |
| SE (1) | SE7702004L (cs) |
| SU (1) | SU625609A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO4970714A1 (es) * | 1997-09-05 | 2000-11-07 | Boehringer Mannheim Gmbh | Derivados ureido y tioureido de 4-amino-2(5h)-furanonas y 4-amino-2(5h) tiofenonas como agentes antitumorales |
-
1977
- 1977-02-23 SE SE7702004A patent/SE7702004L/xx not_active Application Discontinuation
- 1977-03-22 CA CA274,514A patent/CA1097365A/en not_active Expired
- 1977-03-22 AT AT199577A patent/AT354460B/de not_active IP Right Cessation
- 1977-03-22 ES ES457102A patent/ES457102A1/es not_active Expired
- 1977-03-22 PT PT66336A patent/PT66336B/pt unknown
- 1977-03-23 GR GR53079A patent/GR62563B/el unknown
- 1977-03-23 HU HU77DU263A patent/HU173840B/hu unknown
- 1977-03-23 NL NL7703155A patent/NL7703155A/xx not_active Application Discontinuation
- 1977-03-23 DK DK127977A patent/DK143274C/da active
- 1977-03-23 NO NO771021A patent/NO771021L/no unknown
- 1977-03-23 SU SU772463803A patent/SU625609A3/ru active
- 1977-03-23 CH CH364777A patent/CH626081A5/de not_active IP Right Cessation
- 1977-03-24 AR AR269971D patent/AR211956A1/es active
- 1977-03-24 FI FI770929A patent/FI770929A7/fi not_active Application Discontinuation
- 1977-03-24 JP JP3166277A patent/JPS52139056A/ja active Pending
- 1977-03-24 DD DD7700198044A patent/DD130480A5/xx unknown
- 1977-03-24 LU LU77009A patent/LU77009A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU625609A3 (ru) | 1978-09-25 |
| AT354460B (de) | 1979-01-10 |
| PT66336B (en) | 1978-08-16 |
| AR211956A1 (es) | 1978-04-14 |
| SE7702004L (sv) | 1977-09-25 |
| JPS52139056A (en) | 1977-11-19 |
| LU77009A1 (cs) | 1977-10-03 |
| GR62563B (en) | 1979-05-10 |
| DK143274B (da) | 1981-08-03 |
| NO771021L (no) | 1977-09-27 |
| DK143274C (da) | 1981-12-07 |
| FI770929A7 (cs) | 1977-09-25 |
| DK127977A (da) | 1977-09-25 |
| DD130480A5 (de) | 1978-04-05 |
| ES457102A1 (es) | 1978-08-16 |
| PT66336A (en) | 1977-04-01 |
| HU173840B (hu) | 1979-09-28 |
| NL7703155A (nl) | 1977-09-27 |
| ATA199577A (de) | 1979-06-15 |
| CH626081A5 (en) | 1981-10-30 |
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