DE1922702A1 - Verfahren zur Herstellung von 1-Glykosyl-5-azacytosinen - Google Patents
Verfahren zur Herstellung von 1-Glykosyl-5-azacytosinenInfo
- Publication number
- DE1922702A1 DE1922702A1 DE19691922702 DE1922702A DE1922702A1 DE 1922702 A1 DE1922702 A1 DE 1922702A1 DE 19691922702 DE19691922702 DE 19691922702 DE 1922702 A DE1922702 A DE 1922702A DE 1922702 A1 DE1922702 A1 DE 1922702A1
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- carbon atoms
- dihydro
- triazin
- glycosyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 114
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003147 glycosyl group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 9
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 9
- 229960002756 azacitidine Drugs 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- NZHIQLMXOZSBEU-WCTZXXKLSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(dimethylamino)-1,3,5-triazin-2-one Chemical compound O=C1N=C(N(C)C)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NZHIQLMXOZSBEU-WCTZXXKLSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000000526 Experimental Leukemia Diseases 0.000 description 1
- 241000243320 Hydrozoa Species 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
- 241000124008 Mammalia Species 0.000 description 1
- 206010028400 Mutagenic effect Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- NONVMYDWLSJWRI-ZGFBMJKBSA-N [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-methylsulfanyl-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound CSc1ncn([C@@H]2O[C@H](COC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)[C@H]2OC(=O)c2ccccc2)c(=O)n1 NONVMYDWLSJWRI-ZGFBMJKBSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000002759 chromosomal effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- -1 glycosyl cyanates Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/12—Triazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS339968 | 1968-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1922702A1 true DE1922702A1 (de) | 1969-11-20 |
Family
ID=5373920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691922702 Pending DE1922702A1 (de) | 1968-05-08 | 1969-05-03 | Verfahren zur Herstellung von 1-Glykosyl-5-azacytosinen |
Country Status (12)
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6887855B2 (en) | 2003-03-17 | 2005-05-03 | Pharmion Corporation | Forms of 5-azacytidine |
| US6943249B2 (en) | 2003-03-17 | 2005-09-13 | Ash Stevens, Inc. | Methods for isolating crystalline Form I of 5-azacytidine |
| US7038038B2 (en) | 2003-03-17 | 2006-05-02 | Pharmion Corporation | Synthesis of 5-azacytidine |
| US7135464B2 (en) | 2002-06-05 | 2006-11-14 | Supergen, Inc. | Method of administering decitabine |
| US7250416B2 (en) | 2005-03-11 | 2007-07-31 | Supergen, Inc. | Azacytosine analogs and derivatives |
| US7276228B2 (en) | 2001-04-24 | 2007-10-02 | Supergen, Inc. | Methods for treating hematological disorders through inhibition of DNA methylation and histone deacetylase |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US7700567B2 (en) | 2005-09-29 | 2010-04-20 | Supergen, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| US8212021B2 (en) | 2008-08-08 | 2012-07-03 | Scinopharm Taiwan, Ltd. | Process for making 5-azacytosine nucleosides and their derivatives |
| US9381207B2 (en) | 2011-08-30 | 2016-07-05 | Astex Pharmaceuticals, Inc. | Drug formulations |
| WO2017090275A1 (ja) | 2015-11-27 | 2017-06-01 | 大原薬品工業株式会社 | ５－アザシチジン又は其の２'－デオキシ体の５'位ジベンジル燐酸エステル |
| WO2017183217A1 (ja) | 2016-04-21 | 2017-10-26 | 大原薬品工業株式会社 | ５－アザシチジン類の糖部シリルエーテル誘導体 |
| US9901641B2 (en) | 2016-04-21 | 2018-02-27 | Ohara Pharmaceutical Co., Ltd. | Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety |
| US9951098B2 (en) | 2011-03-31 | 2018-04-24 | Pharmion Llc | Synthesis of 5-azacytidine |
| US10227374B2 (en) | 2016-04-21 | 2019-03-12 | Ohara Pharmaceutical Co., Ltd. | Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety |
| US10485764B2 (en) | 2015-07-02 | 2019-11-26 | Otsuka Pharmaceutical Co., Ltd. | Lyophilized pharmaceutical compositions |
| US10519190B2 (en) | 2017-08-03 | 2019-12-31 | Otsuka Pharmaceutical Co., Ltd. | Drug compound and purification methods thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2012888C3 (de) * | 1970-03-14 | 1981-04-02 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von 5-Azapyrimidinnucleosiden |
| US20060014949A1 (en) * | 2004-07-13 | 2006-01-19 | Supergen Inc. | Compositions and formulations of decitabine polymorphs and methods of use thereof |
| DK3782612T3 (da) | 2008-05-15 | 2024-01-15 | Celgene Corp | Orale formuleringer af cytidinanaloger og fremgangsmåder til anvendelse deraf |
-
1969
- 1969-04-23 CH CH619669A patent/CH527207A/de not_active IP Right Cessation
- 1969-04-24 GB GB1227691D patent/GB1227691A/en not_active Expired
- 1969-04-29 BE BE732268D patent/BE732268A/xx unknown
- 1969-04-29 IT IT1620369A patent/IT1037009B/it active
- 1969-05-03 DE DE19691922702 patent/DE1922702A1/de active Pending
- 1969-05-06 NL NL6906909A patent/NL6906909A/xx unknown
- 1969-05-07 ES ES366910A patent/ES366910A1/es not_active Expired
- 1969-05-07 FR FR6914547A patent/FR2008048A1/fr active Pending
- 1969-05-07 BR BR20860069A patent/BR6908600D0/pt unknown
- 1969-05-07 AT AT439269A patent/AT306930B/de not_active IP Right Cessation
- 1969-05-08 CA CA050902A patent/CA921904A/en not_active Expired
- 1969-05-08 JP JP3545969A patent/JPS4916435B1/ja active Pending
Cited By (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7276228B2 (en) | 2001-04-24 | 2007-10-02 | Supergen, Inc. | Methods for treating hematological disorders through inhibition of DNA methylation and histone deacetylase |
| US7135464B2 (en) | 2002-06-05 | 2006-11-14 | Supergen, Inc. | Method of administering decitabine |
| US7144873B2 (en) | 2002-06-05 | 2006-12-05 | Supergen, Inc. | Kit for delivering decitabine in vivo |
| US9192620B2 (en) | 2003-03-17 | 2015-11-24 | Pharmion Llc | Pharmaceutical compositions comprising forms of 5-azacytidine |
| US6887855B2 (en) | 2003-03-17 | 2005-05-03 | Pharmion Corporation | Forms of 5-azacytidine |
| US7038038B2 (en) | 2003-03-17 | 2006-05-02 | Pharmion Corporation | Synthesis of 5-azacytidine |
| US8481715B2 (en) | 2003-03-17 | 2013-07-09 | Pharmion Llc | Methods for isolating crystalline form I of 5-azacytidine |
| US6943249B2 (en) | 2003-03-17 | 2005-09-13 | Ash Stevens, Inc. | Methods for isolating crystalline Form I of 5-azacytidine |
| US8513406B2 (en) | 2003-03-17 | 2013-08-20 | Pharmion Llc | Pharmaceutical compositions comprising forms of 5-azacytidine |
| US8975392B2 (en) | 2003-03-17 | 2015-03-10 | Pharmion Llc | Methods for isolating crystalline form I of 5-azacytidine |
| US7078518B2 (en) | 2003-03-17 | 2006-07-18 | Pharmion Corporation | Forms of 5-Azacytidine |
| US7700770B2 (en) | 2003-03-17 | 2010-04-20 | Celgene Corporation | Methods for isolating crystalline form I of 5-azacytidine |
| US7772199B2 (en) | 2003-03-17 | 2010-08-10 | Celgene Corporation | Forms of 5-azacytidine |
| US7858774B2 (en) | 2003-03-17 | 2010-12-28 | Pharmion Llc | Synthesis of 5-azacytidine |
| US8058424B2 (en) | 2003-03-17 | 2011-11-15 | Pharmion Llc | Synthesis of 5-azacytidine |
| US8211862B2 (en) | 2003-03-17 | 2012-07-03 | Pharmion Llc | Pharmaceutical compositions comprising crystal forms of 5-azacytidine |
| US8779117B2 (en) | 2003-03-17 | 2014-07-15 | Pharmion Llc | Pharmaceutical compositions comprising 5-azacytidine monohydrate |
| US8614313B2 (en) | 2003-03-17 | 2013-12-24 | Pharmion Llc | Pharmaceutical compositions comprising forms of 5-azacytidine |
| US7250416B2 (en) | 2005-03-11 | 2007-07-31 | Supergen, Inc. | Azacytosine analogs and derivatives |
| US7700567B2 (en) | 2005-09-29 | 2010-04-20 | Supergen, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| US10933079B2 (en) | 2005-09-29 | 2021-03-02 | Astex Pharmaceuticals, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| US9358248B2 (en) | 2005-09-29 | 2016-06-07 | Astex Pharmaceuticals, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| US10456415B2 (en) | 2005-09-29 | 2019-10-29 | Astex Pharmaceuticals, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| US9480698B2 (en) | 2005-09-29 | 2016-11-01 | Astex Pharmaceuticals, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| US8461123B2 (en) | 2005-09-29 | 2013-06-11 | Astex Pharmaceuticals, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8212021B2 (en) | 2008-08-08 | 2012-07-03 | Scinopharm Taiwan, Ltd. | Process for making 5-azacytosine nucleosides and their derivatives |
| US9951098B2 (en) | 2011-03-31 | 2018-04-24 | Pharmion Llc | Synthesis of 5-azacytidine |
| US9913856B2 (en) | 2011-08-30 | 2018-03-13 | Astex Pharmaceuticals, Inc. | Drug formulations |
| US9381207B2 (en) | 2011-08-30 | 2016-07-05 | Astex Pharmaceuticals, Inc. | Drug formulations |
| US10517886B2 (en) | 2011-08-30 | 2019-12-31 | Astex Pharmaceuticals, Inc. | Drug formulations |
| US10485764B2 (en) | 2015-07-02 | 2019-11-26 | Otsuka Pharmaceutical Co., Ltd. | Lyophilized pharmaceutical compositions |
| US9670238B1 (en) | 2015-11-27 | 2017-06-06 | Ohara Pharmaceutical Co., Ltd. | 5′-dibenzyl phosphates of 5-azacytidine or 2′-deoxy-5-azacytidine |
| WO2017090275A1 (ja) | 2015-11-27 | 2017-06-01 | 大原薬品工業株式会社 | ５－アザシチジン又は其の２'－デオキシ体の５'位ジベンジル燐酸エステル |
| KR20180088664A (ko) | 2015-11-27 | 2018-08-06 | 오하라 야꾸힝 고교 가부시키가이샤 | 5-아자사이티딘 또는 그 2'-데옥시체의 5’-위치 인산 디벤질 에스테르 |
| US9901641B2 (en) | 2016-04-21 | 2018-02-27 | Ohara Pharmaceutical Co., Ltd. | Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety |
| EP3543249A1 (en) | 2016-04-21 | 2019-09-25 | Ohara Pharmaceutical Co., Ltd. | Sugar moiety silyl ether derivative of 5-azacytidine |
| US10227374B2 (en) | 2016-04-21 | 2019-03-12 | Ohara Pharmaceutical Co., Ltd. | Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety |
| WO2017183217A1 (ja) | 2016-04-21 | 2017-10-26 | 大原薬品工業株式会社 | ５－アザシチジン類の糖部シリルエーテル誘導体 |
| US10519190B2 (en) | 2017-08-03 | 2019-12-31 | Otsuka Pharmaceutical Co., Ltd. | Drug compound and purification methods thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2008048A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-01-16 |
| BR6908600D0 (pt) | 1973-02-22 |
| ES366910A1 (es) | 1971-03-16 |
| IT1037009B (it) | 1979-11-10 |
| CA921904A (en) | 1973-02-27 |
| BE732268A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-01 |
| JPS4916435B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-22 |
| NL6906909A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-11-11 |
| CH527207A (de) | 1972-08-31 |
| AT306930B (de) | 1973-04-25 |
| GB1227691A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-07 |
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