GB1136214A - Thebaine and oripavine derivatives - Google Patents
Thebaine and oripavine derivativesInfo
- Publication number
- GB1136214A GB1136214A GB25289/65A GB2528965A GB1136214A GB 1136214 A GB1136214 A GB 1136214A GB 25289/65 A GB25289/65 A GB 25289/65A GB 2528965 A GB2528965 A GB 2528965A GB 1136214 A GB1136214 A GB 1136214A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- derivative
- thebaine
- oripavine
- followed
- 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.)
- Expired
Links
- ZKLXUUYLEHCAMF-UUWFMWQGSA-N Oripavine Chemical class C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ZKLXUUYLEHCAMF-UUWFMWQGSA-N 0.000 title abstract 9
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 title abstract 7
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 title abstract 7
- 229930003945 thebaine Natural products 0.000 title abstract 7
- 229940051808 oripavine derivative analgesics Drugs 0.000 title abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- -1 nicotinoyl Chemical group 0.000 abstract 4
- 238000005917 acylation reaction Methods 0.000 abstract 3
- 125000002723 alicyclic group Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 230000009467 reduction Effects 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 238000007126 N-alkylation reaction Methods 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 2
- 238000010520 demethylation reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- VQJMAIZOEPPELO-KYGIZGOZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-(2-hydroxy-5-methylhexan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol hydrochloride Chemical compound Cl.CO[C@]12CC[C@@]3(C[C@@H]1C(C)(O)CCC(C)C)[C@H]1Cc4ccc(O)c5O[C@@H]2[C@]3(CCN1CC1CC1)c45 VQJMAIZOEPPELO-KYGIZGOZSA-N 0.000 abstract 1
- QKQQEIVDLRUZRP-UUWFMWQGSA-N (4r,7ar,12bs)-7,9-dimethoxy-1,2,3,4,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline Chemical class C([C@@H](NCC1)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 QKQQEIVDLRUZRP-UUWFMWQGSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- FRLKJAAPFJROFZ-UHFFFAOYSA-N N-nororipavine Chemical class COC1=CC=C2C(NCC3)CC4=CC=C(O)C5=C4C23C1O5 FRLKJAAPFJROFZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 abstract 1
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- QKQQEIVDLRUZRP-UHFFFAOYSA-N northebaine Natural products COC1=CC=C2C(NCC3)CC4=CC=C(OC)C5=C4C23C1O5 QKQQEIVDLRUZRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25289/65A GB1136214A (en) | 1965-06-15 | 1965-06-15 | Thebaine and oripavine derivatives |
| US478738A US3474101A (en) | 1960-09-05 | 1965-08-10 | Thebaine and oripavine derivatives |
| NO163395A NO119590B (enrdf_load_stackoverflow) | 1965-06-15 | 1966-06-10 | |
| LU51306A LU51306A1 (enrdf_load_stackoverflow) | 1965-06-15 | 1966-06-13 | |
| FI661555A FI49724C (fi) | 1965-06-15 | 1966-06-13 | Menetelmä valmistaa farmakologisesti vaikuttavia N-syklopropyyli-metyy li-6,14-endoetano-tetrahydronororipaviineja. |
| SE08101/66A SE325276B (enrdf_load_stackoverflow) | 1965-06-15 | 1966-06-14 | |
| ES0327925A ES327925A1 (es) | 1965-06-15 | 1966-06-14 | Un procedimiento para la produccion de derivados hidrogenados de tebaina y oripavina. |
| BR180359/66A BR6680359D0 (pt) | 1965-06-15 | 1966-06-14 | Um processo para a producao de derivados hidrogenados de tebaina e oripavina |
| NL6608255A NL6608255A (enrdf_load_stackoverflow) | 1965-06-15 | 1966-06-14 | |
| DK307766AA DK115926B (da) | 1965-06-15 | 1966-06-15 | Fremgangsmåde til fremstilling af thebain- eller oripavinderivater eller salte deraf. |
| FR65560A FR6395M (enrdf_load_stackoverflow) | 1965-06-15 | 1966-06-15 | |
| DE19661795642 DE1795642A1 (de) | 1965-06-15 | 1966-06-15 | N-Cyclopropylmethyl-6,14-endo-aethano-7-(2-hydroxy-2-propyl)-tetrahydronororipavin,seine Salze,Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel |
| DE19661620206 DE1620206A1 (de) | 1965-06-15 | 1966-06-15 | In 7-Stellung substituierte 6,14-endo-AEthanotetrahydrothebain-,-tetrahydronorthebain- und -tetrahydronororipavinverbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CH359670A CH551415A (de) | 1965-06-15 | 1966-06-15 | Verfahren zur herstellung von heterocyclischen verbindungen. |
| AT571566A AT272530B (de) | 1965-06-15 | 1966-06-15 | Verfahren zur Herstellung von neuen Thebain- und Oripavinderivaten |
| CH861766A CH558362A (de) | 1965-06-15 | 1966-06-15 | Verfahren zur herstellung von endoaethano-tetrahydrothebainen bzw. -oripavinen. |
| BE682551D BE682551A (enrdf_load_stackoverflow) | 1965-06-15 | 1966-06-15 | |
| US726591A US3433791A (en) | 1960-09-05 | 1968-05-03 | Endoethano nor oripavines and nor thebaines |
| US726592A US3442900A (en) | 1960-09-05 | 1968-05-03 | Endoetheno thebaines and oripavines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25289/65A GB1136214A (en) | 1965-06-15 | 1965-06-15 | Thebaine and oripavine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1136214A true GB1136214A (en) | 1968-12-11 |
Family
ID=10225305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25289/65A Expired GB1136214A (en) | 1960-09-05 | 1965-06-15 | Thebaine and oripavine derivatives |
Country Status (14)
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2313596A (en) * | 1996-05-28 | 1997-12-03 | Dong Kook Pharm Co Ltd | Novel buprenorphine analgesic analogues |
| RU2138502C1 (ru) * | 1999-03-29 | 1999-09-27 | Закрытое акционерное общество "РМА-Фарм" | Способ получения 17-циклопропилметил-6,14-эндо-этано-7-(2-гидрокси-3,3-диметилбут-2-ил)тетр агидро-17-норорипавина |
| US7405301B2 (en) | 2000-08-25 | 2008-07-29 | Glaxowellcome Australia Ltd. | Chemical methods |
| WO2010014229A1 (en) * | 2008-07-30 | 2010-02-04 | Purdue Pharma L.P. | Buprenorphine analogs |
| WO2010039216A1 (en) * | 2008-09-30 | 2010-04-08 | Mallinckrodt Inc. | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| WO2010121369A1 (en) | 2009-04-24 | 2010-10-28 | Brock University | Processes for the preparation of morphinane and morphinone compounds |
| US8119803B2 (en) | 2004-09-30 | 2012-02-21 | Johnson Matthey Public Limited Company | Preparation of opiate analgesics by reductive alkylation |
| WO2013007986A1 (en) | 2011-07-08 | 2013-01-17 | The University Of Bath | Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse |
| US8703099B2 (en) | 2005-02-24 | 2014-04-22 | Dr Pharma Nova, Llc | Registry method and control system for DEA schedule II-V medicines |
| JP2016503754A (ja) * | 2012-12-07 | 2016-02-08 | パーデュー、ファーマ、リミテッド、パートナーシップ | オピオイド受容体モジュレーターとしてのブプレノルフィン類似体 |
| US9308202B2 (en) | 2006-11-21 | 2016-04-12 | Purdue Pharma L.P. | Transdermal therapeutic system for administering the active substance buprenorphine |
| US9549903B2 (en) | 2011-12-12 | 2017-01-24 | Purdue Pharma L.P. | Transdermal delivery system comprising buprenorphine |
| US9937164B2 (en) | 2012-07-26 | 2018-04-10 | Camurus Ab | Opioid formulations |
| US11529345B2 (en) | 2013-06-04 | 2022-12-20 | Lts Lohmann Therapie-Systeme Ag | Buprenorphine transdermal delivery system |
| WO2023111125A1 (en) | 2021-12-16 | 2023-06-22 | Arevipharma Gmbh | Method of making buprenorphine and precursor compounds thereof |
| US12161640B2 (en) | 2012-07-26 | 2024-12-10 | Camurus Ab | Opioid formulations |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2554816B1 (fr) * | 1983-11-16 | 1986-09-26 | Sanofi Sa | Nouveau derive de la nororipavine presentant a la fois une activite agoniste et antagoniste des recepteurs morphiniques |
| GB2388369B (en) * | 2002-05-10 | 2004-05-05 | Reckitt Benckiser Healthcare | Demethylation of thebaine derivative |
-
1965
- 1965-06-15 GB GB25289/65A patent/GB1136214A/en not_active Expired
-
1966
- 1966-06-10 NO NO163395A patent/NO119590B/no unknown
- 1966-06-13 LU LU51306A patent/LU51306A1/xx unknown
- 1966-06-13 FI FI661555A patent/FI49724C/fi active
- 1966-06-14 NL NL6608255A patent/NL6608255A/xx unknown
- 1966-06-14 SE SE08101/66A patent/SE325276B/xx unknown
- 1966-06-14 BR BR180359/66A patent/BR6680359D0/pt unknown
- 1966-06-14 ES ES0327925A patent/ES327925A1/es not_active Expired
- 1966-06-15 AT AT571566A patent/AT272530B/de active
- 1966-06-15 FR FR65560A patent/FR6395M/fr not_active Expired
- 1966-06-15 CH CH861766A patent/CH558362A/de not_active IP Right Cessation
- 1966-06-15 BE BE682551D patent/BE682551A/xx not_active IP Right Cessation
- 1966-06-15 DK DK307766AA patent/DK115926B/da unknown
- 1966-06-15 DE DE19661620206 patent/DE1620206A1/de active Pending
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2313596B (en) * | 1996-05-28 | 1998-08-05 | Dong Kook Pharm Co Ltd | Novel buprenorphine analgesic analogues |
| GB2313596A (en) * | 1996-05-28 | 1997-12-03 | Dong Kook Pharm Co Ltd | Novel buprenorphine analgesic analogues |
| RU2138502C1 (ru) * | 1999-03-29 | 1999-09-27 | Закрытое акционерное общество "РМА-Фарм" | Способ получения 17-циклопропилметил-6,14-эндо-этано-7-(2-гидрокси-3,3-диметилбут-2-ил)тетр агидро-17-норорипавина |
| US7405301B2 (en) | 2000-08-25 | 2008-07-29 | Glaxowellcome Australia Ltd. | Chemical methods |
| US8318937B2 (en) | 2004-09-30 | 2012-11-27 | Johnson Matthey Public Limited Company | Preparation of opiate analgesics by reductive alkylation |
| EP1794165B2 (en) † | 2004-09-30 | 2020-04-29 | Johnson Matthey Public Limited Company | Preparation of opiate analgesics by reductive alkylation |
| US8119803B2 (en) | 2004-09-30 | 2012-02-21 | Johnson Matthey Public Limited Company | Preparation of opiate analgesics by reductive alkylation |
| US8703099B2 (en) | 2005-02-24 | 2014-04-22 | Dr Pharma Nova, Llc | Registry method and control system for DEA schedule II-V medicines |
| US9308202B2 (en) | 2006-11-21 | 2016-04-12 | Purdue Pharma L.P. | Transdermal therapeutic system for administering the active substance buprenorphine |
| AU2009277095B2 (en) * | 2008-07-30 | 2012-09-06 | Purdue Pharma L.P. | Buprenorphine analogs |
| US8530494B2 (en) | 2008-07-30 | 2013-09-10 | Purdue Pharma Lp | Buprenophine analogs |
| EP2703404A1 (en) * | 2008-07-30 | 2014-03-05 | Purdue Pharma L.P. | Buprenorphine analogs |
| RU2520222C2 (ru) * | 2008-07-30 | 2014-06-20 | Пэдью Фарма Л.П. | Аналоги бупренорфина |
| WO2010014229A1 (en) * | 2008-07-30 | 2010-02-04 | Purdue Pharma L.P. | Buprenorphine analogs |
| US8293906B2 (en) | 2008-09-30 | 2012-10-23 | Mallinckrodt Llc | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| WO2010039216A1 (en) * | 2008-09-30 | 2010-04-08 | Mallinckrodt Inc. | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| EP2342207B1 (en) | 2008-09-30 | 2015-11-11 | Mallinckrodt LLC | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| WO2010121369A1 (en) | 2009-04-24 | 2010-10-28 | Brock University | Processes for the preparation of morphinane and morphinone compounds |
| US9051334B2 (en) | 2011-07-08 | 2015-06-09 | The University Of Bath | Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse |
| US10030031B2 (en) | 2011-07-08 | 2018-07-24 | The University Of Bath | Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse, depression, anxiety, or a compulsive disorder |
| WO2013007986A1 (en) | 2011-07-08 | 2013-01-17 | The University Of Bath | Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse |
| US9480684B2 (en) | 2011-07-08 | 2016-11-01 | The University Of Bath | Orvinol and thevinol derivatives useful in the treatment of anxiety or a compulsive disorder |
| US9259422B2 (en) | 2011-07-08 | 2016-02-16 | The University Of Bath | Orvinol and thevinol derivatives useful in the treatment of depression |
| US9549903B2 (en) | 2011-12-12 | 2017-01-24 | Purdue Pharma L.P. | Transdermal delivery system comprising buprenorphine |
| US9937164B2 (en) | 2012-07-26 | 2018-04-10 | Camurus Ab | Opioid formulations |
| US10912772B2 (en) | 2012-07-26 | 2021-02-09 | Camurus Ab | Opioid formulations |
| US11110084B2 (en) | 2012-07-26 | 2021-09-07 | Camurus Ab | Opioid formulations |
| US12161640B2 (en) | 2012-07-26 | 2024-12-10 | Camurus Ab | Opioid formulations |
| US12318379B2 (en) | 2012-07-26 | 2025-06-03 | Camurus Ab | Opioid formulations |
| JP2016503754A (ja) * | 2012-12-07 | 2016-02-08 | パーデュー、ファーマ、リミテッド、パートナーシップ | オピオイド受容体モジュレーターとしてのブプレノルフィン類似体 |
| US11529345B2 (en) | 2013-06-04 | 2022-12-20 | Lts Lohmann Therapie-Systeme Ag | Buprenorphine transdermal delivery system |
| WO2023111125A1 (en) | 2021-12-16 | 2023-06-22 | Arevipharma Gmbh | Method of making buprenorphine and precursor compounds thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| SE325276B (enrdf_load_stackoverflow) | 1970-06-29 |
| FR6395M (enrdf_load_stackoverflow) | 1968-10-21 |
| FI49724C (fi) | 1975-09-10 |
| DK115926B (da) | 1969-11-24 |
| BR6680359D0 (pt) | 1973-12-26 |
| BE682551A (enrdf_load_stackoverflow) | 1966-11-14 |
| FI49724B (enrdf_load_stackoverflow) | 1975-06-02 |
| LU51306A1 (enrdf_load_stackoverflow) | 1966-08-16 |
| NL6608255A (enrdf_load_stackoverflow) | 1966-12-16 |
| DE1620206A1 (de) | 1970-03-19 |
| NO119590B (enrdf_load_stackoverflow) | 1970-06-08 |
| AT272530B (de) | 1969-07-10 |
| CH558362A (de) | 1975-01-31 |
| ES327925A1 (es) | 1967-04-01 |
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