CH419172A - Verfahren zur Herstellung basischer Dibenzooxepin- bzw. Dibenzo-thiepin-Derivate - Google Patents
Verfahren zur Herstellung basischer Dibenzooxepin- bzw. Dibenzo-thiepin-DerivateInfo
- Publication number
- CH419172A CH419172A CH1167562A CH1167562A CH419172A CH 419172 A CH419172 A CH 419172A CH 1167562 A CH1167562 A CH 1167562A CH 1167562 A CH1167562 A CH 1167562A CH 419172 A CH419172 A CH 419172A
- Authority
- CH
- Switzerland
- Prior art keywords
- dibenzo
- formula
- thiepin
- oxepin
- propylidene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000008510 dibenzothiepins Chemical class 0.000 title description 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- -1 acyl radicals Chemical class 0.000 description 19
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 description 9
- 150000003840 hydrochlorides Chemical class 0.000 description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- YKNORODREYVARM-UHFFFAOYSA-N 2-(phenoxymethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1COC1=CC=CC=C1 YKNORODREYVARM-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- JEVCFPPYJUBGIO-UHFFFAOYSA-N 2-(phenoxymethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1COC1=CC=CC=C1 JEVCFPPYJUBGIO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- IQMZULGMADGDLC-UHFFFAOYSA-N 2-benzylsulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SCC1=CC=CC=C1 IQMZULGMADGDLC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NPBUOQARVHNKAK-UHFFFAOYSA-N 1-[3-(6H-benzo[c][1]benzoxepin-11-ylidene)propyl]piperidine Chemical compound N1(CCCCC1)CCC=C1C2=C(OCC3=C1C=CC=C3)C=CC=C2 NPBUOQARVHNKAK-UHFFFAOYSA-N 0.000 description 1
- GIGQDDWBWCUOFZ-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-6h-benzo[c][1]benzothiepin-11-ol Chemical compound C1SC2=CC=CC=C2C(CCCN(C)C)(O)C2=CC=CC=C21 GIGQDDWBWCUOFZ-UHFFFAOYSA-N 0.000 description 1
- QXPRAGVOCILNHG-UHFFFAOYSA-N 2-(phenylsulfanylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CSC1=CC=CC=C1 QXPRAGVOCILNHG-UHFFFAOYSA-N 0.000 description 1
- MHNSPTUQQIYJOT-UHFFFAOYSA-N 3-(6h-benzo[c][1]benzoxepin-11-ylidene)propyl-dimethylazanium;chloride Chemical compound Cl.C1OC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 MHNSPTUQQIYJOT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical compound [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- XUPZAARQDNSRJB-UHFFFAOYSA-N dothiepin hydrochloride Chemical compound [Cl-].C1SC2=CC=CC=C2C(=CCC[NH+](C)C)C2=CC=CC=C21 XUPZAARQDNSRJB-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB64294A DE1232161B (de) | 1961-10-07 | 1961-10-07 | Verfahren zur Herstellung von basisch substituierten Dibenzo-oxepinen und deren Salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH419172A true CH419172A (de) | 1966-08-31 |
Family
ID=6974332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1167562A CH419172A (de) | 1961-10-07 | 1962-10-04 | Verfahren zur Herstellung basischer Dibenzooxepin- bzw. Dibenzo-thiepin-Derivate |
Country Status (7)
| Country | Link |
|---|---|
| CH (1) | CH419172A (da) |
| CY (1) | CY396A (da) |
| DK (3) | DK111033B (da) |
| GB (1) | GB950717A (da) |
| LU (1) | LU42476A1 (da) |
| MY (1) | MY6700116A (da) |
| NL (4) | NL6508317A (da) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0409406A3 (en) * | 1989-06-19 | 1991-04-03 | The Wellcome Foundation Limited | Aryl-substituted amine derivatives useful in cancer therapy |
| US5208238A (en) * | 1989-06-19 | 1993-05-04 | Burroughs Wellcome Company | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5300282A (en) * | 1989-06-19 | 1994-04-05 | Burroughs-Wellcome Company | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5346897A (en) * | 1989-06-19 | 1994-09-13 | Burroughs Wellcome Co. | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5364843A (en) * | 1989-06-19 | 1994-11-15 | Burroughs Wellcome Co. | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101234B1 (en) * | 1982-08-06 | 1986-10-29 | The Boots Company PLC | Therapeutic agent |
| DE19848200A1 (de) * | 1998-10-20 | 2000-04-27 | Basf Ag | Verfahren zur Trocknung von Phenoxymethylbenzoesäuren |
-
0
- NL NL121414D patent/NL121414C/xx active
- NL NL284002D patent/NL284002A/xx unknown
-
1962
- 1962-09-27 GB GB3672462A patent/GB950717A/en not_active Expired
- 1962-10-04 DK DK430462A patent/DK111033B/da unknown
- 1962-10-04 CH CH1167562A patent/CH419172A/de unknown
- 1962-10-04 DK DK476164A patent/DK105767C/da active
- 1962-10-04 DK DK476064A patent/DK106861C/da active
- 1962-10-05 LU LU42476D patent/LU42476A1/xx unknown
-
1965
- 1965-06-29 NL NL6508317A patent/NL6508317A/xx unknown
- 1965-06-29 NL NL6508318A patent/NL6508318A/xx unknown
-
1967
- 1967-05-30 CY CY39667A patent/CY396A/xx unknown
- 1967-12-31 MY MY6700116A patent/MY6700116A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0409406A3 (en) * | 1989-06-19 | 1991-04-03 | The Wellcome Foundation Limited | Aryl-substituted amine derivatives useful in cancer therapy |
| EP0487502A3 (en) * | 1989-06-19 | 1992-06-24 | The Wellcome Foundation Limited | Pharmaceutically active aryl-substituted amine derivatives |
| US5208238A (en) * | 1989-06-19 | 1993-05-04 | Burroughs Wellcome Company | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5300282A (en) * | 1989-06-19 | 1994-04-05 | Burroughs-Wellcome Company | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5346897A (en) * | 1989-06-19 | 1994-09-13 | Burroughs Wellcome Co. | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5364843A (en) * | 1989-06-19 | 1994-11-15 | Burroughs Wellcome Co. | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
| US5395610A (en) * | 1989-06-19 | 1995-03-07 | Burroughs-Wellcome Co. | Agents for potentiating the effects of antitumor agents and combating multiple drug resistance |
Also Published As
| Publication number | Publication date |
|---|---|
| CY396A (en) | 1967-05-30 |
| GB950717A (en) | 1964-02-26 |
| NL6508318A (da) | 1965-08-25 |
| NL284002A (da) | |
| NL6508317A (da) | 1965-08-25 |
| MY6700116A (en) | 1967-12-31 |
| LU42476A1 (da) | 1962-12-11 |
| DK106861C (da) | 1967-03-28 |
| DK111033B (da) | 1968-05-13 |
| DK105767C (da) | 1966-11-07 |
| NL121414C (da) |
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