NO134337B - - Google Patents
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- Publication number
- NO134337B NO134337B NO495/70A NO49570A NO134337B NO 134337 B NO134337 B NO 134337B NO 495/70 A NO495/70 A NO 495/70A NO 49570 A NO49570 A NO 49570A NO 134337 B NO134337 B NO 134337B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- benzene
- water
- yield
- reaction
- Prior art date
Links
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000011592 zinc chloride Substances 0.000 claims description 15
- 235000005074 zinc chloride Nutrition 0.000 claims description 15
- -1 1,4-butylene Chemical group 0.000 claims description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- GOLHZPOXCLTFRB-UHFFFAOYSA-N furan-3-carboxamide Chemical class NC(=O)C=1C=COC=1 GOLHZPOXCLTFRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 36
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- IHCCAYCGZOLTEU-UHFFFAOYSA-M 3-furoate Chemical compound [O-]C(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-M 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NRNCYKJWCUYOBK-UHFFFAOYSA-N ethyl 2,4,5-trimethylfuran-3-carboxylate Chemical compound CCOC(=O)C1=C(C)OC(C)=C1C NRNCYKJWCUYOBK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 2
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 2
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- RWENMRVLTSDEIS-UHFFFAOYSA-N 2,4,5-trimethylfuran-3-carboxamide Chemical class CC=1OC(C)=C(C(N)=O)C=1C RWENMRVLTSDEIS-UHFFFAOYSA-N 0.000 description 1
- BAZBYDHOWMSZBD-UHFFFAOYSA-N 2,4,5-trimethylfuran-3-carboxylic acid Chemical compound CC=1OC(C)=C(C(O)=O)C=1C BAZBYDHOWMSZBD-UHFFFAOYSA-N 0.000 description 1
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 description 1
- VCCNAPAOKUSZGC-UHFFFAOYSA-N 3-oxo-n-(2-phenylphenyl)butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C1=CC=CC=C1 VCCNAPAOKUSZGC-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- PCGMZJHAOYYUHF-UHFFFAOYSA-N n-(4-fluorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(F)C=C1 PCGMZJHAOYYUHF-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000008096 xylene Substances 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79910969A | 1969-02-13 | 1969-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134337B true NO134337B (ro) | 1976-06-14 |
| NO134337C NO134337C (ro) | 1976-09-22 |
Family
ID=25175061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO495/70A NO134337C (ro) | 1969-02-13 | 1970-02-12 |
Country Status (20)
| Country | Link |
|---|---|
| AT (1) | AT294060B (ro) |
| BE (1) | BE745863A (ro) |
| CA (1) | CA932334A (ro) |
| CH (2) | CH567495A5 (ro) |
| CS (1) | CS188869B2 (ro) |
| DE (1) | DE2006472C2 (ro) |
| DK (1) | DK134176B (ro) |
| EG (1) | EG12357A (ro) |
| ES (1) | ES376539A1 (ro) |
| FR (1) | FR2068181A5 (ro) |
| GB (1) | GB1303844A (ro) |
| IL (1) | IL33880A (ro) |
| LU (1) | LU60345A1 (ro) |
| NL (1) | NL172061C (ro) |
| NO (1) | NO134337C (ro) |
| PL (1) | PL80863B1 (ro) |
| RO (1) | RO57890A (ro) |
| SE (1) | SE393985C (ro) |
| TR (1) | TR16671A (ro) |
| ZA (1) | ZA70828B (ro) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
| DE2019535B2 (de) * | 1970-04-23 | 1973-04-05 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | 2,5-dimethylfuran-3-carbonsaeurecycloalkylamide und diese verbindungen enthaltende fungizide mittel |
| BE795524A (fr) * | 1972-02-16 | 1973-08-16 | Basf Ag | Procede de preparation d'esters de l'acide dimethyl-2,5-furanne-carboxylique-3 |
| GB1387652A (en) * | 1972-05-10 | 1975-03-19 | Shell Int Research | Process for preparing furan carboxamides |
| DE2703023A1 (de) * | 1977-01-26 | 1978-07-27 | Basf Ag | Furanderivate |
| DE2826013A1 (de) * | 1978-06-14 | 1980-01-03 | Basf Ag | Verfahren zur herstellung von 2,5-dimethylfuran-3-carbonsaeurealkylestern |
| DE10222884A1 (de) * | 2002-05-23 | 2003-12-04 | Bayer Cropscience Ag | Furancarboxamide |
| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| DE102004005786A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| DE102004005785A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004005787A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Carboxamide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1215066A (en) * | 1968-03-25 | 1970-12-09 | Shell Int Research | Acrylamides and their use as fungicides |
| DE1768686B1 (de) * | 1968-06-19 | 1971-05-27 | Basf Ag | Furan-3-carbonsaeureanilide und deren Verwendung als Fungizid |
-
1969
- 1969-10-28 CA CA066031A patent/CA932334A/en not_active Expired
-
1970
- 1970-02-06 ZA ZA700828A patent/ZA70828B/xx unknown
- 1970-02-09 GB GB608370A patent/GB1303844A/en not_active Expired
- 1970-02-10 IL IL33880A patent/IL33880A/xx unknown
- 1970-02-11 SE SE7001749A patent/SE393985C/xx unknown
- 1970-02-12 CS CS70991A patent/CS188869B2/cs unknown
- 1970-02-12 NL NLAANVRAGE7002030,A patent/NL172061C/xx not_active IP Right Cessation
- 1970-02-12 PL PL1970138768A patent/PL80863B1/pl unknown
- 1970-02-12 FR FR7005054A patent/FR2068181A5/fr not_active Expired
- 1970-02-12 NO NO495/70A patent/NO134337C/no unknown
- 1970-02-12 BE BE745863D patent/BE745863A/xx not_active IP Right Cessation
- 1970-02-12 DK DK68870AA patent/DK134176B/da unknown
- 1970-02-12 DE DE2006472A patent/DE2006472C2/de not_active Expired
- 1970-02-13 AT AT133670A patent/AT294060B/de not_active IP Right Cessation
- 1970-02-13 TR TR16671A patent/TR16671A/xx unknown
- 1970-02-13 ES ES376539A patent/ES376539A1/es not_active Expired
- 1970-02-13 CH CH1666673A patent/CH567495A5/xx not_active IP Right Cessation
- 1970-02-13 RO RO62460A patent/RO57890A/ro unknown
- 1970-02-13 CH CH211370A patent/CH558349A/xx not_active IP Right Cessation
- 1970-02-13 LU LU60345D patent/LU60345A1/xx unknown
-
1976
- 1976-09-04 EG EG547/76A patent/EG12357A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| SE393985C (sv) | 1980-12-11 |
| FR2068181A5 (ro) | 1971-08-20 |
| ZA70828B (en) | 1971-09-29 |
| DE2006472A1 (de) | 1970-08-27 |
| CA932334A (en) | 1973-08-21 |
| NL172061B (nl) | 1983-02-01 |
| ES376539A1 (es) | 1972-04-16 |
| LU60345A1 (ro) | 1971-06-21 |
| NL7002030A (ro) | 1970-08-17 |
| IL33880A (en) | 1984-09-30 |
| GB1303844A (ro) | 1973-01-24 |
| RO57890A (ro) | 1975-08-15 |
| EG12357A (en) | 1978-09-30 |
| DK134176C (ro) | 1977-02-28 |
| NL172061C (nl) | 1983-07-01 |
| NO134337C (ro) | 1976-09-22 |
| BE745863A (fr) | 1970-08-12 |
| DE2006472C2 (de) | 1983-12-22 |
| TR16671A (tr) | 1973-03-01 |
| CH558349A (de) | 1975-01-31 |
| SE393985B (sv) | 1977-05-31 |
| DK134176B (da) | 1976-09-27 |
| CH567495A5 (ro) | 1975-10-15 |
| IL33880A0 (en) | 1970-04-20 |
| AT294060B (de) | 1971-11-10 |
| CS188869B2 (en) | 1979-03-30 |
| PL80863B1 (ro) | 1975-08-30 |
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