NO123389B - - Google Patents
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- Publication number
- NO123389B NO123389B NO168402A NO16840267A NO123389B NO 123389 B NO123389 B NO 123389B NO 168402 A NO168402 A NO 168402A NO 16840267 A NO16840267 A NO 16840267A NO 123389 B NO123389 B NO 123389B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- aniline
- piperidyl
- methyl
- hours
- Prior art date
Links
- -1 arylmercapto Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000003053 piperidines Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 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
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 235000019270 ammonium chloride Nutrition 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229940072033 potash Drugs 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 235000015320 potassium carbonate Nutrition 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 239000008096 xylene Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012491 analyte Substances 0.000 description 8
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 7
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- GKLFDWGXDPXYFM-UHFFFAOYSA-N 3-benzylsulfanyl-N-phenylaniline Chemical compound C(SC1=CC=CC(NC2=CC=CC=C2)=C1)C1=CC=CC=C1 GKLFDWGXDPXYFM-UHFFFAOYSA-N 0.000 description 2
- YNHGMBTXSRJGLC-UHFFFAOYSA-N 3-ethylsulfanyl-n-phenylaniline Chemical compound CCSC1=CC=CC(NC=2C=CC=CC=2)=C1 YNHGMBTXSRJGLC-UHFFFAOYSA-N 0.000 description 2
- MILDLALYTVTBLU-UHFFFAOYSA-N 3-phenoxy-n-phenylaniline Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1NC1=CC=CC=C1 MILDLALYTVTBLU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- DBVMVLJJUKDKPU-UHFFFAOYSA-N N-phenyl-3-propan-2-ylsulfanylaniline Chemical compound CC(C)SC1=CC=CC(NC2=CC=CC=C2)=C1 DBVMVLJJUKDKPU-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JFDYNLNAMOSAQH-UHFFFAOYSA-N n-phenyl-3-phenylmethoxyaniline Chemical compound C=1C=CC=CC=1COC(C=1)=CC=CC=1NC1=CC=CC=C1 JFDYNLNAMOSAQH-UHFFFAOYSA-N 0.000 description 2
- BXSGWVKHMJIWNI-UHFFFAOYSA-N n-phenyl-3-propoxyaniline Chemical compound CCCOC1=CC=CC(NC=2C=CC=CC=2)=C1 BXSGWVKHMJIWNI-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ISVGOYORMPENJM-UHFFFAOYSA-N 2-(3-benzylsulfanylanilino)benzoic acid Chemical compound C(C1=CC=CC=C1)SC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 ISVGOYORMPENJM-UHFFFAOYSA-N 0.000 description 1
- LIWNFNNKPBGCFM-UHFFFAOYSA-N 2-(3-ethylsulfanylanilino)benzoic acid Chemical compound CCSC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 LIWNFNNKPBGCFM-UHFFFAOYSA-N 0.000 description 1
- JLVZKULKBLUFIY-UHFFFAOYSA-N 2-(3-methylsulfanylanilino)benzoic acid Chemical compound CSC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1 JLVZKULKBLUFIY-UHFFFAOYSA-N 0.000 description 1
- ACFBDJYMPSIKOW-UHFFFAOYSA-N 2-(3-phenoxyanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(OC=2C=CC=CC=2)=C1 ACFBDJYMPSIKOW-UHFFFAOYSA-N 0.000 description 1
- DPBZMTSEJAIAHE-UHFFFAOYSA-N 2-(3-propan-2-yloxyanilino)benzoic acid Chemical compound C(C)(C)OC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 DPBZMTSEJAIAHE-UHFFFAOYSA-N 0.000 description 1
- RMMIRCPZDWCSMD-UHFFFAOYSA-N 2-(3-propan-2-ylsulfanylanilino)benzoic acid Chemical compound C(C)(C)SC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 RMMIRCPZDWCSMD-UHFFFAOYSA-N 0.000 description 1
- VNWIKUXZNUBJRL-UHFFFAOYSA-N 2-(3-propoxyanilino)benzoic acid Chemical compound C(CC)OC=1C=C(C=CC1)NC=1C(C(=O)O)=CC=CC1 VNWIKUXZNUBJRL-UHFFFAOYSA-N 0.000 description 1
- RCMQHFPLNQIFCX-UHFFFAOYSA-N 2-chlorobenzoic acid;potassium Chemical compound [K].OC(=O)C1=CC=CC=C1Cl RCMQHFPLNQIFCX-UHFFFAOYSA-N 0.000 description 1
- ZIZHOYOBASUITD-UHFFFAOYSA-N 3-butoxyaniline Chemical compound CCCCOC1=CC=CC(N)=C1 ZIZHOYOBASUITD-UHFFFAOYSA-N 0.000 description 1
- ZZZQPNICTIZSQR-UHFFFAOYSA-N 3-ethoxy-n-phenylaniline Chemical compound CCOC1=CC=CC(NC=2C=CC=CC=2)=C1 ZZZQPNICTIZSQR-UHFFFAOYSA-N 0.000 description 1
- DBQWEIGOXKOQAG-UHFFFAOYSA-N 3-ethylsulfanylaniline Chemical compound CCSC1=CC=CC(N)=C1 DBQWEIGOXKOQAG-UHFFFAOYSA-N 0.000 description 1
- NGTRZJDYCCOXBA-UHFFFAOYSA-N 3-methylsulfanyl-n-phenylaniline Chemical compound CSC1=CC=CC(NC=2C=CC=CC=2)=C1 NGTRZJDYCCOXBA-UHFFFAOYSA-N 0.000 description 1
- KCHLDNLIJVSRPK-UHFFFAOYSA-N 3-methylsulfanylaniline Chemical compound CSC1=CC=CC(N)=C1 KCHLDNLIJVSRPK-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- QMGBIPKOKCSUCL-UHFFFAOYSA-N 3-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=CC(N)=C1 QMGBIPKOKCSUCL-UHFFFAOYSA-N 0.000 description 1
- VPAHCDXFLUSULH-UHFFFAOYSA-N 3-propoxyaniline Chemical compound CCCOC1=CC=CC(N)=C1 VPAHCDXFLUSULH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000250507 Gigaspora candida Species 0.000 description 1
- 244000185238 Lophostemon confertus Species 0.000 description 1
- RUEJFLRIFUSIPM-UHFFFAOYSA-N N-(3-propan-2-ylphenyl)thiohydroxylamine Chemical compound C(C)(C)C=1C=C(NS)C=CC1 RUEJFLRIFUSIPM-UHFFFAOYSA-N 0.000 description 1
- 235000013234 Rhus glabra Nutrition 0.000 description 1
- 235000013831 Rhus typhina Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJEOAHXVAXYSHE-UHFFFAOYSA-N n-phenyl-3-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=CC(NC=2C=CC=CC=2)=C1 IJEOAHXVAXYSHE-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3802466 | 1966-06-14 | ||
| JP3802666 | 1966-06-14 | ||
| JP3802566 | 1966-06-14 | ||
| JP4763866A JPS4413952B1 (https=) | 1966-07-22 | 1966-07-22 | |
| JP7865866 | 1966-12-02 | ||
| JP7931466 | 1966-12-05 | ||
| JP7955466 | 1966-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123389B true NO123389B (https=) | 1971-11-08 |
Family
ID=27564462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO168402A NO123389B (https=) | 1966-06-14 | 1967-05-31 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3567716A (https=) |
| BE (1) | BE699872A (https=) |
| CH (1) | CH489525A (https=) |
| DE (1) | DE1670565A1 (https=) |
| ES (1) | ES341746A1 (https=) |
| FR (1) | FR7095M (https=) |
| GB (1) | GB1152788A (https=) |
| NL (1) | NL6708021A (https=) |
| NO (1) | NO123389B (https=) |
| SE (1) | SE324576B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7961100A (en) * | 1999-10-28 | 2001-05-08 | Daiichi Pharmaceutical Co., Ltd. | Drug discharge pump inhibitors |
| JPWO2002087589A1 (ja) * | 2001-04-26 | 2004-08-12 | 第一製薬株式会社 | 薬剤排出ポンプ阻害薬 |
| JP2002322054A (ja) * | 2001-04-26 | 2002-11-08 | Dai Ichi Seiyaku Co Ltd | 薬剤排出ポンプ阻害薬 |
| US7282532B2 (en) * | 2003-06-06 | 2007-10-16 | M Management-Tex, Ltd. | Flexible bakeware |
-
1967
- 1967-05-31 US US642303A patent/US3567716A/en not_active Expired - Lifetime
- 1967-05-31 NO NO168402A patent/NO123389B/no unknown
- 1967-06-05 CH CH793167A patent/CH489525A/de not_active IP Right Cessation
- 1967-06-07 GB GB26227/67A patent/GB1152788A/en not_active Expired
- 1967-06-09 NL NL6708021A patent/NL6708021A/xx unknown
- 1967-06-12 DE DE19671670565 patent/DE1670565A1/de active Pending
- 1967-06-13 ES ES341746A patent/ES341746A1/es not_active Expired
- 1967-06-13 BE BE699872D patent/BE699872A/xx unknown
- 1967-06-13 SE SE8300/67A patent/SE324576B/xx unknown
- 1967-11-24 FR FR129642A patent/FR7095M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR7095M (https=) | 1969-07-07 |
| DE1670565A1 (de) | 1972-02-24 |
| SE324576B (https=) | 1970-06-08 |
| US3567716A (en) | 1971-03-02 |
| BE699872A (https=) | 1967-11-16 |
| CH489525A (de) | 1970-04-30 |
| NL6708021A (https=) | 1967-12-15 |
| ES341746A1 (es) | 1968-10-16 |
| GB1152788A (en) | 1969-05-21 |
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