SU508185A3 - Способ получени -замещенных лактамов - Google Patents
Способ получени -замещенных лактамовInfo
- Publication number
- SU508185A3 SU508185A3 SU1621307A SU1621307A SU508185A3 SU 508185 A3 SU508185 A3 SU 508185A3 SU 1621307 A SU1621307 A SU 1621307A SU 1621307 A SU1621307 A SU 1621307A SU 508185 A3 SU508185 A3 SU 508185A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxopyrrolidino
- dimethyl
- acetamide
- methyl
- ethanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000003951 lactams Chemical class 0.000 title claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 230000004071 biological effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 21
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 14
- -1 2-oxopyrrolidino Chemical group 0.000 claims 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 4
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 238000002955 isolation Methods 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims 1
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims 1
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 claims 1
- GWVUNSZJQQHRRB-UHFFFAOYSA-N 3-methyl-2-(2-oxopyrrolidin-1-yl)butanamide Chemical compound CC(C)C(C(N)=O)N1CCCC1=O GWVUNSZJQQHRRB-UHFFFAOYSA-N 0.000 claims 1
- QAVODDLLBLKACG-UHFFFAOYSA-N 4,5-dimethyl-1,3-dihydropyrrol-2-one Chemical class CC1=C(C)NC(=O)C1 QAVODDLLBLKACG-UHFFFAOYSA-N 0.000 claims 1
- IIUCUFMCFVESRB-UHFFFAOYSA-N C(C)(=O)NN1C(CC(C1)C)=O Chemical compound C(C)(=O)NN1C(CC(C1)C)=O IIUCUFMCFVESRB-UHFFFAOYSA-N 0.000 claims 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 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- MXJMAXBTCAEHIM-UHFFFAOYSA-N N-(3,5-dimethyl-2-oxopyrrolidin-1-yl)acetamide Chemical compound CC1CC(C)C(=O)N1NC(C)=O MXJMAXBTCAEHIM-UHFFFAOYSA-N 0.000 claims 1
- 229940125585 NDV-HXP-S Drugs 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000004922 lacquer Substances 0.000 claims 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- SNWQKAWITMVCQW-UHFFFAOYSA-N phthalylsulfacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1C(O)=O SNWQKAWITMVCQW-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 230000003716 rejuvenation Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB697870A GB1309692A (en) | 1970-02-13 | 1970-02-13 | N-substituted lactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU508185A3 true SU508185A3 (ru) | 1976-03-25 |
Family
ID=9824325
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1621307A SU508185A3 (ru) | 1970-02-13 | 1971-02-12 | Способ получени -замещенных лактамов |
| SU1893858A SU508186A3 (ru) | 1970-02-13 | 1971-02-12 | Способ получени -замещенных лактамов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1893858A SU508186A3 (ru) | 1970-02-13 | 1971-02-12 | Способ получени -замещенных лактамов |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2663899C1 (ru) * | 2017-07-19 | 2018-08-13 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Способ получения 1-карбамоилметил-4-фенил-2-пирролидона |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1045043B (it) * | 1975-08-13 | 1980-04-21 | Isf Spa | Derivati pirrolidinici |
| GB1583871A (en) | 1976-10-19 | 1981-02-04 | Ucb Sa | Anti-aggregants |
| BE864269A (fr) * | 1977-03-03 | 1978-06-16 | Parke Davis & Co | Nouveaux n-(aminoalkyl substitue)-2-oxo-1-pyrrolidine-acetamides et procedes pour les produire |
| ATE27T1 (de) * | 1978-05-08 | 1981-04-15 | Ucb Sa | Lactam-n-essigsaeuren und ihre amide, verfahren zu ihrer herstellung und heilmittel, die sie enthalten |
| IT1141287B (it) * | 1979-06-13 | 1986-10-01 | Nattermann A & Cie | Ammidi di acidi pirrolidin-(2)-on-(1)-ilalchil-carbossilici,procedimento per la loro preparazione e prodotti medicinali che le contengono |
| FR2515179A1 (fr) * | 1981-07-24 | 1983-04-29 | Hoffmann La Roche | Derives de pyrrolidine, leur procede de preparation, les intermediaires pour leur synthese et leur application therapeutique |
| EP0089900B1 (en) * | 1982-03-24 | 1985-12-27 | Prodes S.A. | New n-((2-oxo-1-pyrrolidinyl)acetyl)piperazines, the methods of producing such new compounds and their salts as well as pharmaceutical preparations for therapeutic use containing these compounds or salts |
| GB8412358D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
| GB8412357D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
| DE3420193A1 (de) * | 1984-05-30 | 1985-12-05 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel |
| US4804400A (en) * | 1986-09-12 | 1989-02-14 | Ciba-Geigy Corporation | N-phenyl-maleimides and herbicidal and plant growth regulating methods of use thereof |
| GB8827389D0 (en) * | 1988-11-23 | 1988-12-29 | Ucb Sa | Process for preparation of(s)alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| AR020115A1 (es) * | 1998-08-06 | 2002-04-10 | Daiichi Seiyaku Co | Agente terapeutico o preventivo para epilepsias rebeldes y uso del compuesto para la produccion de los mismos |
| GB0004297D0 (en) * | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
| US6686477B2 (en) | 2000-09-29 | 2004-02-03 | Eastman Chemical Company | Highly enantiomerically pure lactam-substituted propanoic acid derivatives and methods of making and using same |
| EP1395560A1 (en) * | 2001-05-23 | 2004-03-10 | Ucb, S.A. | 2-oxo-piperidinyl- and 2-oxo-azepanyl alkanoic acid derivativ es for the treatment of epilepsy and other neurological disorders |
| ES2314090T3 (es) | 2001-08-10 | 2009-03-16 | Ucb Pharma S.A. | Compuestos de oxopirrolidina, preparacion de dichos compuestos y uso de los mismos en la fabricacion de levetiracetam y sus analogos. |
| ATE353645T1 (de) * | 2001-10-08 | 2007-03-15 | Ucb Sa | Verwendung von 2-oxo-1-pyrrolidin-derivaten zur herstellung eines arzneimittels zur behandlung von dyskinesia |
| CN1802352A (zh) | 2003-02-03 | 2006-07-12 | 特瓦制药工业有限公司 | 制备左乙拉西坦的方法 |
| ES2214147B1 (es) * | 2003-02-28 | 2005-10-01 | Farma-Lepori S.A. | Procedimiento de obtencion de un agente antiepileptico. |
| CA2497062A1 (en) | 2004-02-18 | 2005-08-18 | Dr. Reddy's Laboratories Limited | Preparation of amino acid amides |
| CA2488325C (en) | 2004-11-22 | 2010-08-24 | Apotex Pharmachem Inc. | Improved process for the preparation of (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide and (r)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| US20080146819A1 (en) * | 2005-03-10 | 2008-06-19 | Rubamin Limited | Process for Preparing Levetiracetam |
| ES2441178T3 (es) | 2005-06-01 | 2014-02-03 | Ucb Pharma, S.A. | Derivados de 2-oxo-1-pirrolidina, procedimientos para prepararlos y el uso terapéutico de los mismos sobre el sistema nervioso central |
| EP2147911A1 (en) | 2008-07-24 | 2010-01-27 | ZaCh System S.p.A. | Process for the preparation of levetiracetam |
| DK2346500T3 (en) | 2008-10-16 | 2017-07-17 | Univ Johns Hopkins | Methods and compositions for improving cognitive function |
| US8785661B2 (en) | 2009-05-13 | 2014-07-22 | Nektar Therapeutics | Oligome-containing pyrrolidine compounds |
| US7939676B2 (en) | 2009-09-17 | 2011-05-10 | Zach System S.P.A. | Process for the preparation of levetiracetam |
| JP6082250B2 (ja) | 2010-02-09 | 2017-02-15 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 認知機能を改善するための方法および組成物 |
| WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| WO2014144801A1 (en) | 2013-03-15 | 2014-09-18 | Agenebio Inc. | Methods and compositions for improving cognitive function |
| US10806717B2 (en) | 2013-03-15 | 2020-10-20 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| MY203464A (en) | 2014-01-21 | 2024-06-28 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| KR20200126026A (ko) | 2014-01-21 | 2020-11-05 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| CN104059010A (zh) * | 2014-06-12 | 2014-09-24 | 浙江华海药业股份有限公司 | 一种制备2-(2-氧代吡咯烷-1-基)-丁酸酯的方法 |
| CN106591179B (zh) * | 2016-12-05 | 2018-07-03 | 长兴制药股份有限公司 | 甲基包囊菌及其在选择性拆分制备(S)-α-乙基-2-氧-1-吡咯烷乙酸盐上的应用 |
| US11384050B1 (en) | 2021-02-03 | 2022-07-12 | Vitaworks Ip, Llc | Method for preparing levetiracetam and intermediates thereof |
| CN113979911A (zh) * | 2021-11-12 | 2022-01-28 | 汤斌 | 一种从大鲵肽中提取乙拉西坦的方法 |
| EP4572852A1 (en) | 2022-08-19 | 2025-06-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1039113A (en) * | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
-
1970
- 1970-02-13 GB GB697870A patent/GB1309692A/en not_active Expired
-
1971
- 1971-02-08 FR FR7104195A patent/FR2081508B2/fr not_active Expired
- 1971-02-09 NL NLAANVRAGE7101697,A patent/NL168830C/xx not_active IP Right Cessation
- 1971-02-10 DK DK59571AA patent/DK137451B/da not_active IP Right Cessation
- 1971-02-10 CS CS987A patent/CS167911B2/cs unknown
- 1971-02-10 YU YU306/71A patent/YU34876B/xx unknown
- 1971-02-10 ES ES388135A patent/ES388135A2/es not_active Expired
- 1971-02-10 BE BE762728A patent/BE762728R/xx active
- 1971-02-10 FI FI383/71A patent/FI54916C/fi active
- 1971-02-11 ZA ZA710877A patent/ZA71877B/xx unknown
- 1971-02-11 DE DE2106418A patent/DE2106418C2/de not_active Expired
- 1971-02-11 CH CH200171A patent/CH530395A/fr not_active IP Right Cessation
- 1971-02-12 SU SU1621307A patent/SU508185A3/ru active
- 1971-02-12 SU SU1893858A patent/SU508186A3/ru active
- 1971-02-12 JP JP612471A patent/JPS535301B1/ja active Pending
- 1971-12-10 CS CS140674A patent/CS167912B2/cs unknown
-
1974
- 1974-12-31 MY MY197472A patent/MY7400072A/xx unknown
-
1977
- 1977-11-07 JP JP13335277A patent/JPS53130656A/ja active Granted
-
1978
- 1978-06-19 YU YU01445/78A patent/YU144578A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2663899C1 (ru) * | 2017-07-19 | 2018-08-13 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Способ получения 1-карбамоилметил-4-фенил-2-пирролидона |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5420491B2 (enrdf_load_stackoverflow) | 1979-07-23 |
| BE762728R (fr) | 1971-08-10 |
| FI54916B (fi) | 1978-12-29 |
| FI54916C (fi) | 1979-04-10 |
| DE2106418C2 (de) | 1983-12-22 |
| DE2106418A1 (de) | 1971-08-19 |
| FR2081508B2 (enrdf_load_stackoverflow) | 1975-06-06 |
| YU34876B (en) | 1980-04-30 |
| DK137451C (enrdf_load_stackoverflow) | 1978-07-24 |
| MY7400072A (en) | 1974-12-31 |
| GB1309692A (en) | 1973-03-14 |
| NL7101697A (enrdf_load_stackoverflow) | 1971-08-17 |
| ES388135A2 (es) | 1973-05-01 |
| JPS535301B1 (enrdf_load_stackoverflow) | 1978-02-25 |
| ZA71877B (en) | 1971-10-27 |
| NL168830C (nl) | 1982-05-17 |
| YU30671A (en) | 1979-10-31 |
| FR2081508A2 (enrdf_load_stackoverflow) | 1971-12-03 |
| YU144578A (en) | 1982-10-31 |
| NL168830B (nl) | 1981-12-16 |
| SU508186A3 (ru) | 1976-03-25 |
| CH530395A (fr) | 1972-11-15 |
| CS167912B2 (enrdf_load_stackoverflow) | 1976-05-28 |
| JPS53130656A (en) | 1978-11-14 |
| CS167911B2 (enrdf_load_stackoverflow) | 1976-05-28 |
| DK137451B (da) | 1978-03-06 |
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