CS200231B2 - Process for preparing n-substituted lactames - Google Patents
Process for preparing n-substituted lactames Download PDFInfo
- Publication number
- CS200231B2 CS200231B2 CS776799A CS679977A CS200231B2 CS 200231 B2 CS200231 B2 CS 200231B2 CS 776799 A CS776799 A CS 776799A CS 679977 A CS679977 A CS 679977A CS 200231 B2 CS200231 B2 CS 200231B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- oxo
- compound
- yield
- methyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 150000003951 lactams Chemical class 0.000 claims abstract description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000005977 Ethylene Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- -1 nitrogenous compound Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 238000002844 melting Methods 0.000 description 5
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VKGDUWNNSTVCRJ-UHFFFAOYSA-N ethyl 2-[[2-(2-oxopyrrolidin-1-yl)acetyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)CN1CCCC1=O VKGDUWNNSTVCRJ-UHFFFAOYSA-N 0.000 description 4
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- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 241000906446 Theraps Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NPHPYZQBNHXQFJ-UHFFFAOYSA-N n-(2-anilino-2-oxoethyl)-n-methyl-2-(2-oxopyrrolidin-1-yl)acetamide Chemical compound C1CCC(=O)N1CC(=O)N(C)CC(=O)NC1=CC=CC=C1 NPHPYZQBNHXQFJ-UHFFFAOYSA-N 0.000 description 2
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- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
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- OHNMKQDTCXPESI-UHFFFAOYSA-N benzyl 2-[methyl-[2-(2-oxopyrrolidin-1-yl)acetyl]amino]acetate Chemical compound C1CCC(=O)N1CC(=O)N(C)CC(=O)OCC1=CC=CC=C1 OHNMKQDTCXPESI-UHFFFAOYSA-N 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VCBSMHZNRBWEIJ-UHFFFAOYSA-L trimethyl-[5-[5-(trimethylazaniumyl)pentoxy]pentyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCCCCOCCCCC[N+](C)(C)C VCBSMHZNRBWEIJ-UHFFFAOYSA-L 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43934/76A GB1539817A (en) | 1976-10-22 | 1976-10-22 | N-substituted lactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200231B2 true CS200231B2 (en) | 1980-08-29 |
Family
ID=10431009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776799A CS200231B2 (en) | 1976-10-22 | 1977-10-19 | Process for preparing n-substituted lactames |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4162325A (en, 2012) |
| JP (1) | JPS5839148B2 (en, 2012) |
| AT (1) | AT352742B (en, 2012) |
| BE (1) | BE859925A (en, 2012) |
| BG (1) | BG28413A3 (en, 2012) |
| CA (1) | CA1095040A (en, 2012) |
| CH (1) | CH625214A5 (en, 2012) |
| CS (1) | CS200231B2 (en, 2012) |
| CY (1) | CY1037A (en, 2012) |
| DD (1) | DD131930A5 (en, 2012) |
| DE (1) | DE2747369A1 (en, 2012) |
| DK (1) | DK461877A (en, 2012) |
| ES (1) | ES463424A1 (en, 2012) |
| FI (1) | FI66600C (en, 2012) |
| FR (1) | FR2368474B1 (en, 2012) |
| GB (1) | GB1539817A (en, 2012) |
| HK (1) | HK2380A (en, 2012) |
| HU (1) | HU174864B (en, 2012) |
| IL (1) | IL53171A (en, 2012) |
| KE (1) | KE3013A (en, 2012) |
| MY (1) | MY8000264A (en, 2012) |
| NL (1) | NL7711414A (en, 2012) |
| PL (1) | PL110679B1 (en, 2012) |
| SE (1) | SE425782B (en, 2012) |
| SU (2) | SU805945A3 (en, 2012) |
| YU (1) | YU251977A (en, 2012) |
| ZA (1) | ZA776260B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005689B1 (fr) * | 1978-05-08 | 1981-03-18 | U C B, S.A. | Nouveaux acides lactame-N-acétiques et leurs amides, leurs procédés de préparation et compositions thérapeutiques |
| EP0115473A3 (de) * | 1983-01-27 | 1987-01-21 | Ciba-Geigy Ag | Substituierte Pyrrolidinonderivate und Verfahren zu ihrer Herstellung |
| FI840260L (fi) * | 1983-01-27 | 1984-07-28 | Ciba Geigy Ag | Pyrrolidinonderivat och foerfarande foer deras framstaellning. |
| IT1190378B (it) * | 1985-06-21 | 1988-02-16 | Isf Spa | Derivati pirrolidonici |
| US5118811A (en) * | 1989-04-13 | 1992-06-02 | Japan Tobacco Inc. | Amino acid derivatives possessing prolyl endopeptidase-inhibitory activities |
| US5206386A (en) * | 1991-03-20 | 1993-04-27 | Isp Investments Inc. | Controlled release N-substituted pyrrolidone esters and process for the use thereof |
| DE4308034A1 (de) * | 1993-03-13 | 1994-09-15 | Cassella Ag | Neue Heterocyclen, ihre Herstellung und ihre Verwendung |
| US5658940A (en) * | 1995-10-06 | 1997-08-19 | Celgene Corporation | Succinimide and maleimide cytokine inhibitors |
| US5914332A (en) * | 1995-12-13 | 1999-06-22 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| CN114685342B (zh) * | 2020-12-25 | 2024-05-10 | 长沙博源医疗科技有限公司 | 一种左乙拉西坦衍生物、免疫原、抗左乙拉西坦特异性抗体及其制备方法与应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121723A (en) * | 1955-11-02 | 1964-02-18 | Sterling Drug Inc | Lower alkyl n-(tertiary-amino-lower-alkyl) lower alkamates and quaternary ammonium salts thereof |
| GB1039113A (en) * | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
| NL7407140A (nl) * | 1974-03-07 | 1975-09-09 | Jose Maria Espinos Taya En Jos | Werkwijze voor de bereiding van een n-gesub- stitueerd pyrrolidon. |
| AT360980B (de) * | 1976-01-14 | 1981-02-10 | Pliva Pharm & Chem Works | Verfahren zur herstellung von n-alkylamiden des 2-oxo-1-pyrrolidins |
-
1976
- 1976-10-22 GB GB43934/76A patent/GB1539817A/en not_active Expired
-
1977
- 1977-10-07 CA CA288,302A patent/CA1095040A/en not_active Expired
- 1977-10-17 SE SE7711667A patent/SE425782B/xx unknown
- 1977-10-17 DK DK461877A patent/DK461877A/da not_active Application Discontinuation
- 1977-10-17 FI FI773069A patent/FI66600C/fi not_active IP Right Cessation
- 1977-10-18 NL NL7711414A patent/NL7711414A/xx not_active Application Discontinuation
- 1977-10-19 CS CS776799A patent/CS200231B2/cs unknown
- 1977-10-19 PL PL1977201601A patent/PL110679B1/pl not_active IP Right Cessation
- 1977-10-19 IL IL53171A patent/IL53171A/xx unknown
- 1977-10-19 FR FR7731876A patent/FR2368474B1/fr not_active Expired
- 1977-10-19 BG BG037618A patent/BG28413A3/xx unknown
- 1977-10-19 US US05/843,692 patent/US4162325A/en not_active Expired - Lifetime
- 1977-10-20 HU HU77UE81A patent/HU174864B/hu unknown
- 1977-10-20 YU YU02519/77A patent/YU251977A/xx unknown
- 1977-10-20 CY CY1037A patent/CY1037A/xx unknown
- 1977-10-20 ZA ZA00776260A patent/ZA776260B/xx unknown
- 1977-10-20 BE BE1008460A patent/BE859925A/xx not_active IP Right Cessation
- 1977-10-20 CH CH1278777A patent/CH625214A5/fr not_active IP Right Cessation
- 1977-10-20 JP JP52126346A patent/JPS5839148B2/ja not_active Expired
- 1977-10-20 AT AT749677A patent/AT352742B/de not_active IP Right Cessation
- 1977-10-21 ES ES463424A patent/ES463424A1/es not_active Expired
- 1977-10-21 DE DE19772747369 patent/DE2747369A1/de active Granted
- 1977-10-21 SU SU772534301A patent/SU805945A3/ru active
- 1977-10-21 DD DD7700201648A patent/DD131930A5/xx unknown
-
1978
- 1978-06-13 SU SU782626702A patent/SU937450A1/ru active
-
1980
- 1980-01-11 KE KE3013A patent/KE3013A/xx unknown
- 1980-01-17 HK HK23/80A patent/HK2380A/xx unknown
- 1980-12-31 MY MY1980264A patent/MY8000264A/xx unknown
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