CH351588A - Verfahren zur Herstellung von Sulfonylharnstoffen - Google Patents
Verfahren zur Herstellung von SulfonylharnstoffenInfo
- Publication number
- CH351588A CH351588A CH351588DA CH351588A CH 351588 A CH351588 A CH 351588A CH 351588D A CH351588D A CH 351588DA CH 351588 A CH351588 A CH 351588A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzenesulfonyl
- alkyl
- carbon atoms
- sulfonylureas
- amines
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 17
- -1 phenoxyphenyl Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 235000013877 carbamide Nutrition 0.000 description 8
- 150000003672 ureas Chemical group 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- JTDKEDJPCUTMJL-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JTDKEDJPCUTMJL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 5
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl n-(benzenesulfonyl)carbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- QOCVOOWVZVIZEO-UHFFFAOYSA-N benzene;sulfamide Chemical class NS(N)(=O)=O.C1=CC=CC=C1 QOCVOOWVZVIZEO-UHFFFAOYSA-N 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- XBJPGFREXQDWPN-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylcarbamoyl]benzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC(=O)C1=CC=CC=C1 XBJPGFREXQDWPN-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NWIFRSJMWOEKNP-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylcarbamoyl]acetamide Chemical compound CC(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NWIFRSJMWOEKNP-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 1
- JPADSMQGSZGYPE-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-1-(2-methylpropyl)urea Chemical compound CC1=CC=C(C=C1)S(=O)(=O)N(C(=O)N)CC(C)C JPADSMQGSZGYPE-UHFFFAOYSA-N 0.000 description 1
- BBQLCKFJEDETJU-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-phenylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1 BBQLCKFJEDETJU-UHFFFAOYSA-N 0.000 description 1
- AMWRPZQZUUYQHN-UHFFFAOYSA-N 1-cyclohexyl-1-(4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(C=C1)S(=O)(=O)N(C(=O)N)C1CCCCC1 AMWRPZQZUUYQHN-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OCARDKJCRWODPA-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)N(C(=O)N)CCCC Chemical compound C(C1=CC=CC=C1)S(=O)(=O)N(C(=O)N)CCCC OCARDKJCRWODPA-UHFFFAOYSA-N 0.000 description 1
- BOAAZJCANBJWST-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(C1CCCCC1)=O Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(C1CCCCC1)=O BOAAZJCANBJWST-UHFFFAOYSA-N 0.000 description 1
- KGINXYFISQQUQW-UHFFFAOYSA-N N-(benzenesulfonyl)carbamoyl chloride Chemical class C1(=CC=CC=C1)S(=O)(=O)NC(=O)Cl KGINXYFISQQUQW-UHFFFAOYSA-N 0.000 description 1
- LOWQEDSQFHBDHF-UHFFFAOYSA-N N-(benzenesulfonylcarbamoyl)acetamide Chemical compound C(C)(=O)NC(=O)NS(=O)(=O)C1=CC=CC=C1 LOWQEDSQFHBDHF-UHFFFAOYSA-N 0.000 description 1
- FTUZUVASIBBRPH-UHFFFAOYSA-N N-[(4-methylphenyl)sulfonylcarbamoyl]butanamide Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(CCC)=O FTUZUVASIBBRPH-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BNEBFAXBFRAIGF-UHFFFAOYSA-N ethyl N-acetamido-N-(benzenesulfonyl)carbamate Chemical compound C(C)OC(N(S(=O)(=O)C1=CC=CC=C1)NC(C)=O)=O BNEBFAXBFRAIGF-UHFFFAOYSA-N 0.000 description 1
- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- KNVDHKOSDVFZTO-UHFFFAOYSA-N methyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 KNVDHKOSDVFZTO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- ITHCVNUFCWSLGQ-UHFFFAOYSA-N n-(benzenesulfonylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC(=O)C1=CC=CC=C1 ITHCVNUFCWSLGQ-UHFFFAOYSA-N 0.000 description 1
- 150000003941 n-butylamines Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20751A DE1043318B (de) | 1956-07-10 | 1956-07-10 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH351588A true CH351588A (de) | 1961-01-31 |
Family
ID=7089800
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351588D CH351588A (de) | 1956-07-10 | 1957-01-07 | Verfahren zur Herstellung von Sulfonylharnstoffen |
| CH351589D CH351589A (de) | 1956-07-10 | 1957-01-07 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351589D CH351589A (de) | 1956-07-10 | 1957-01-07 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT195436B (da) |
| CH (2) | CH351588A (da) |
| DE (1) | DE1043318B (da) |
| DK (1) | DK89984C (da) |
| FR (1) | FR1172148A (da) |
-
1956
- 1956-07-10 DE DEF20751A patent/DE1043318B/de active Pending
- 1956-12-15 AT AT195436D patent/AT195436B/de active
-
1957
- 1957-01-07 CH CH351588D patent/CH351588A/de unknown
- 1957-01-07 CH CH351589D patent/CH351589A/de unknown
- 1957-01-26 DK DK32057A patent/DK89984C/da active
- 1957-01-29 FR FR1172148D patent/FR1172148A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT195436B (de) | 1958-02-10 |
| DK89984C (da) | 1960-11-14 |
| FR1172148A (fr) | 1959-02-05 |
| CH351589A (de) | 1961-01-31 |
| DE1043318B (de) | 1958-11-13 |
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