NO780576L - Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivater - Google Patents
Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivaterInfo
- Publication number
- NO780576L NO780576L NO780576A NO780576A NO780576L NO 780576 L NO780576 L NO 780576L NO 780576 A NO780576 A NO 780576A NO 780576 A NO780576 A NO 780576A NO 780576 L NO780576 L NO 780576L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- formula
- isopropyl
- alkyl
- triazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 15
- 150000003918 triazines Chemical class 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 21
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 29
- 239000002585 base Substances 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 9
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
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- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 208000007106 menorrhagia Diseases 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- USJMGSDXAXHGLS-UHFFFAOYSA-N n-(4,6-dioxo-5-propan-2-yl-1,3,5-triazinan-2-yl)-n-pentan-3-ylacetamide Chemical compound CCC(CC)N(C(C)=O)C1NC(=O)N(C(C)C)C(=O)N1 USJMGSDXAXHGLS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7183/77A GB1599518A (en) | 1977-02-21 | 1977-02-21 | 1,3,5-triazine-2,6-diones and pharmaceutical compositions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780576L true NO780576L (no) | 1978-08-22 |
Family
ID=9828208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780576A NO780576L (no) | 1977-02-21 | 1978-02-20 | Analogifremgangsmaate for fremstilling av farmakologisk aktive triazinderivater |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4156002A (sv) |
| JP (1) | JPS53105487A (sv) |
| AR (1) | AR220120A1 (sv) |
| AT (1) | AT358592B (sv) |
| AU (1) | AU519803B2 (sv) |
| BE (1) | BE864124A (sv) |
| CA (1) | CA1117867A (sv) |
| CH (1) | CH637646A5 (sv) |
| CS (2) | CS208463B2 (sv) |
| DD (1) | DD134091A5 (sv) |
| DE (1) | DE2807381A1 (sv) |
| DK (1) | DK67978A (sv) |
| ES (3) | ES467170A1 (sv) |
| FI (1) | FI64152C (sv) |
| FR (1) | FR2381034A1 (sv) |
| GB (1) | GB1599518A (sv) |
| GR (1) | GR62157B (sv) |
| HU (2) | HU176980B (sv) |
| IE (1) | IE46650B1 (sv) |
| IL (1) | IL54026A (sv) |
| IT (1) | IT1158652B (sv) |
| LU (1) | LU79092A1 (sv) |
| MW (1) | MW478A1 (sv) |
| NL (1) | NL7801921A (sv) |
| NO (1) | NO780576L (sv) |
| NZ (1) | NZ186406A (sv) |
| PL (2) | PL109995B1 (sv) |
| PT (1) | PT67668B (sv) |
| SE (1) | SE440775B (sv) |
| SU (2) | SU890976A3 (sv) |
| ZA (1) | ZA78671B (sv) |
| ZM (1) | ZM1878A1 (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE698T1 (de) * | 1978-05-26 | 1982-03-15 | Imperial Chemical Industries Plc | Analgetische 6-acylaminot etrahydro-1,3,5-triazin-2,4-dion-derivate, sie enthaltende pharmazeutische zusammensetzungen und verfahren zu ihrer herstellung. |
| GB8629567D0 (en) * | 1986-12-10 | 1987-01-21 | Boots Co Plc | Therapeutic agents |
| US6348216B1 (en) * | 1996-06-10 | 2002-02-19 | Knoll Pharmaceutical Company | Ibuprofen and narcotic analgesic compositions |
| US6361794B1 (en) | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
| PL2399910T3 (pl) * | 2009-02-13 | 2014-09-30 | Shionogi & Co | Pochodne triazyny jako antagoniści receptora p2x3 i/albo p2x2/3 i kompozycja farmaceutyczna zawierająca je |
| EP2604595B1 (en) * | 2010-08-10 | 2016-03-16 | Shionogi&Co., Ltd. | Triazine derivative and pharmaceutical compound that contains same and exhibits analgesic activity |
| CN103140221A (zh) | 2010-08-10 | 2013-06-05 | 盐野义制药株式会社 | 新型杂环衍生物和含有其的药物组合物 |
| US9550763B2 (en) | 2012-02-09 | 2017-01-24 | Shionogi & Co., Ltd. | Heterocyclic ring and carbocyclic derivative |
| TWI637949B (zh) | 2013-06-14 | 2018-10-11 | 塩野義製藥股份有限公司 | 胺基三衍生物及含有其等之醫藥組合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE357200B (sv) * | 1965-07-21 | 1973-06-18 | Takeda Chemical Industries Ltd | |
| US4035365A (en) * | 1973-11-01 | 1977-07-12 | Imperial Chemical Industries Limited | Triazinediones |
| GB1543037A (en) * | 1975-02-05 | 1979-03-28 | Ici Ltd | Selective herbicidal triazine-diones |
| JPS5623425B2 (sv) * | 1973-11-09 | 1981-05-30 |
-
1977
- 1977-02-21 GB GB7183/77A patent/GB1599518A/en not_active Expired
-
1978
- 1978-02-02 IE IE217/78A patent/IE46650B1/en unknown
- 1978-02-03 ZA ZA00780671A patent/ZA78671B/xx unknown
- 1978-02-07 NZ NZ186406A patent/NZ186406A/en unknown
- 1978-02-07 CA CA000296415A patent/CA1117867A/en not_active Expired
- 1978-02-08 AU AU33112/78A patent/AU519803B2/en not_active Expired
- 1978-02-09 ZM ZM18/78A patent/ZM1878A1/xx unknown
- 1978-02-12 IL IL54026A patent/IL54026A/xx unknown
- 1978-02-13 US US05/877,391 patent/US4156002A/en not_active Expired - Lifetime
- 1978-02-15 HU HU78IE826A patent/HU176980B/hu unknown
- 1978-02-15 PL PL1978211162A patent/PL109995B1/pl unknown
- 1978-02-15 DK DK67978A patent/DK67978A/da not_active Application Discontinuation
- 1978-02-15 HU HU78IE836A patent/HU182653B/hu unknown
- 1978-02-15 PL PL1978204641A patent/PL107871B1/pl unknown
- 1978-02-16 GR GR55469A patent/GR62157B/el unknown
- 1978-02-16 PT PT67668A patent/PT67668B/pt unknown
- 1978-02-17 CS CS781045A patent/CS208463B2/cs unknown
- 1978-02-17 FI FI780529A patent/FI64152C/fi not_active IP Right Cessation
- 1978-02-20 SU SU782587045A patent/SU890976A3/ru active
- 1978-02-20 SE SE7801930A patent/SE440775B/sv not_active IP Right Cessation
- 1978-02-20 BE BE185309A patent/BE864124A/xx not_active IP Right Cessation
- 1978-02-20 FR FR7804760A patent/FR2381034A1/fr active Granted
- 1978-02-20 NO NO780576A patent/NO780576L/no unknown
- 1978-02-20 LU LU79092A patent/LU79092A1/xx unknown
- 1978-02-21 AT AT127178A patent/AT358592B/de not_active IP Right Cessation
- 1978-02-21 DD DD78203776A patent/DD134091A5/xx unknown
- 1978-02-21 AR AR271164A patent/AR220120A1/es active
- 1978-02-21 MW MW4/78A patent/MW478A1/xx unknown
- 1978-02-21 DE DE19782807381 patent/DE2807381A1/de not_active Ceased
- 1978-02-21 JP JP1898978A patent/JPS53105487A/ja active Pending
- 1978-02-21 NL NL7801921A patent/NL7801921A/xx not_active Application Discontinuation
- 1978-02-21 IT IT20500/78A patent/IT1158652B/it active
- 1978-02-21 ES ES467170A patent/ES467170A1/es not_active Expired
- 1978-02-21 CH CH186378A patent/CH637646A5/de not_active IP Right Cessation
- 1978-12-28 ES ES476428A patent/ES476428A1/es not_active Expired
- 1978-12-28 ES ES476427A patent/ES476427A1/es not_active Expired
-
1979
- 1979-02-13 SU SU792723300A patent/SU867303A3/ru active
-
1980
- 1980-05-22 CS CS803610A patent/CS208464B2/cs unknown
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