SU578000A3 - Способ получени производных 3-нитрокумарина или их солей - Google Patents
Способ получени производных 3-нитрокумарина или их солейInfo
- Publication number
- SU578000A3 SU578000A3 SU7402021264A SU2021264A SU578000A3 SU 578000 A3 SU578000 A3 SU 578000A3 SU 7402021264 A SU7402021264 A SU 7402021264A SU 2021264 A SU2021264 A SU 2021264A SU 578000 A3 SU578000 A3 SU 578000A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- added
- hydroxy
- room temperature
- nitrocoumarin
- product
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 4
- YTCVPEZECJYZRK-UHFFFAOYSA-N 3-nitrochromen-2-one Chemical class C1=CC=C2OC(=O)C([N+](=O)[O-])=CC2=C1 YTCVPEZECJYZRK-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 239000000725 suspension Substances 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 21
- 238000001914 filtration Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 7
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- -1 7-ethoxy-4-nitrocoumarin Chemical compound 0.000 description 4
- 229960000956 coumarin Drugs 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- ZLDUKGHXYIMWJP-UHFFFAOYSA-N 7-bromo-4-hydroxy-3-nitrochromen-2-one Chemical compound C1=C(Br)C=CC2=C1OC(=O)C([N+]([O-])=O)=C2O ZLDUKGHXYIMWJP-UHFFFAOYSA-N 0.000 description 3
- 235000001671 coumarin Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VOBWYJZFRGXBFE-UHFFFAOYSA-N 4-hydroxy-3-nitro-7-propoxychromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(OCCC)=CC=C21 VOBWYJZFRGXBFE-UHFFFAOYSA-N 0.000 description 2
- CPMOVDXRQYGPSF-UHFFFAOYSA-N 4-hydroxy-6-methoxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=CC(OC)=CC=C21 CPMOVDXRQYGPSF-UHFFFAOYSA-N 0.000 description 2
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 2
- RASGTZZGBPNBLH-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-nitrochromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O RASGTZZGBPNBLH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- LFFCJEOKCYTBDD-UHFFFAOYSA-N 4-hydroxy-5-methoxychromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=CC=C2OC LFFCJEOKCYTBDD-UHFFFAOYSA-N 0.000 description 1
- WOZQGVWTWZLETB-UHFFFAOYSA-N 4-hydroxy-6,7-dimethyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(C)C(C)=C2 WOZQGVWTWZLETB-UHFFFAOYSA-N 0.000 description 1
- AYHZQBMBPNZPEY-UHFFFAOYSA-N 4-hydroxy-6,7-dimethylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(C)C(C)=C2 AYHZQBMBPNZPEY-UHFFFAOYSA-N 0.000 description 1
- HVHIQQVTLCUBKA-UHFFFAOYSA-N 4-hydroxy-6,8-dimethylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=CC(C)=CC(C)=C21 HVHIQQVTLCUBKA-UHFFFAOYSA-N 0.000 description 1
- KFXXRRQBVLINPH-UHFFFAOYSA-N 4-hydroxy-6-methoxychromen-2-one Chemical compound O1C(=O)C=C(O)C2=CC(OC)=CC=C21 KFXXRRQBVLINPH-UHFFFAOYSA-N 0.000 description 1
- WXTJBTOJTWUFOR-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-nitro-7-propoxychromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(OCCC)C(C)=C2 WXTJBTOJTWUFOR-UHFFFAOYSA-N 0.000 description 1
- DZGDYAJCQWPAKE-UHFFFAOYSA-N 4-hydroxy-7,8-dimethylchromen-2-one Chemical compound OC1=CC(=O)OC2=C(C)C(C)=CC=C21 DZGDYAJCQWPAKE-UHFFFAOYSA-N 0.000 description 1
- MJBHLQMPKBMZSF-UHFFFAOYSA-N 4-hydroxy-7-methoxychromen-2-one Chemical compound OC1=CC(=O)OC2=CC(OC)=CC=C21 MJBHLQMPKBMZSF-UHFFFAOYSA-N 0.000 description 1
- NFFPEZYDUVHXIU-UHFFFAOYSA-N 4-hydroxy-8-methyl-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C=CC=C2C NFFPEZYDUVHXIU-UHFFFAOYSA-N 0.000 description 1
- QFTOEJKXJKAMNK-UHFFFAOYSA-N 6,7-diethyl-4-hydroxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(CC)C(CC)=C2 QFTOEJKXJKAMNK-UHFFFAOYSA-N 0.000 description 1
- KNMCTCABMSGXGR-UHFFFAOYSA-N 6-bromo-4-hydroxychromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C=C2O KNMCTCABMSGXGR-UHFFFAOYSA-N 0.000 description 1
- LVZTYKPCDIGFBZ-UHFFFAOYSA-N 7-ethoxy-6-ethyl-4-hydroxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(OCC)C(CC)=C2 LVZTYKPCDIGFBZ-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/54—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 substituted in the carbocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
- C07D311/50—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring with elements other than carbon and hydrogen in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1887673A GB1432809A (en) | 1973-04-19 | 1973-04-19 | Coumarin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU578000A3 true SU578000A3 (ru) | 1977-10-25 |
Family
ID=10119952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402021264A SU578000A3 (ru) | 1973-04-19 | 1974-04-19 | Способ получени производных 3-нитрокумарина или их солей |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3974289A (enExample) |
| JP (1) | JPS5035170A (enExample) |
| BE (1) | BE813919A (enExample) |
| CH (1) | CH593964A5 (enExample) |
| CS (1) | CS187414B2 (enExample) |
| DD (1) | DD111375A5 (enExample) |
| DE (1) | DE2418344A1 (enExample) |
| ES (1) | ES425514A1 (enExample) |
| FR (1) | FR2226177B1 (enExample) |
| GB (1) | GB1432809A (enExample) |
| HU (1) | HU166816B (enExample) |
| IE (1) | IE39359B1 (enExample) |
| IL (1) | IL44628A (enExample) |
| IN (1) | IN139069B (enExample) |
| MW (1) | MW1474A1 (enExample) |
| NL (1) | NL7405383A (enExample) |
| PL (1) | PL96047B1 (enExample) |
| SU (1) | SU578000A3 (enExample) |
| ZA (1) | ZA742469B (enExample) |
| ZM (1) | ZM6374A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136192A (en) * | 1975-09-23 | 1979-01-23 | Beecham Group Limited | 4-hydroxy-3-nitro (cyano) coumarins |
| US4200577A (en) * | 1975-09-23 | 1980-04-29 | Beecham Group Limited | Coumarin derivatives |
| EP0050396B1 (en) * | 1978-10-20 | 1984-12-27 | Beecham Group Plc | Coumarin intermediates |
| US4380649A (en) * | 1981-11-23 | 1983-04-19 | The Dow Chemical Company | Isophorone derivatives |
| US5484951A (en) * | 1990-10-19 | 1996-01-16 | Octamer, Incorporated | 5-iodo-6-amino-6-nitroso-1,2-benzopyrones useful as cytostatic and antiviral agents |
| WO1992013852A1 (fr) * | 1991-01-31 | 1992-08-20 | Dainippon Ink & Chemicals, Inc. | Derive de benzopyranne et agent anti-allergique le contenant a titre d'ingredient actif |
| US5482975A (en) * | 1991-10-22 | 1996-01-09 | Octamer, Inc. | Adenosine diphosphoribose polymerase binding nitroso aromatic compounds useful as retroviral inactivating agents, anti-retroviral agents and anti-tumor agents |
| US5877185A (en) * | 1991-10-22 | 1999-03-02 | Octamer, Inc. | Synergistic compositions useful as anti-tumor agents |
| US5783599A (en) * | 1993-02-24 | 1998-07-21 | Octamer Inc | Methods of treating cancer and viral infections with 5-iodo-6-amino-and 5-iodo-6-nitroso-1 2-benzopyrones |
| DE4323409A1 (de) * | 1993-07-13 | 1995-01-19 | Boehringer Mannheim Gmbh | Verwendung von Cumarinen und Carbostyrilen als PLA¶2¶-Inhibitoren, neue Cumarine und Carbostyrile, Verfahren zu ihrer Herstellung und Arzneimittel |
| US20110028350A1 (en) * | 1995-12-15 | 2011-02-03 | Affymetrix, Inc. | Photocleavable protecting groups |
| US6147205A (en) * | 1995-12-15 | 2000-11-14 | Affymetrix, Inc. | Photocleavable protecting groups and methods for their use |
| WO2002020150A2 (en) * | 2000-09-11 | 2002-03-14 | Affymetrix, Inc. | Photocleavable protecting groups |
| US7547775B2 (en) * | 2004-12-31 | 2009-06-16 | Affymetrix, Inc. | Parallel preparation of high fidelity probes in an array format |
| US8338093B2 (en) * | 2004-12-31 | 2012-12-25 | Affymetrix, Inc. | Primer array synthesis and validation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1049289A (en) * | 1962-08-18 | 1966-11-23 | Benger Lab Ltd | Chromone derivatives and pharmaceutical compositions containing them |
| GB1147976A (en) * | 1965-12-21 | 1969-04-10 | Fisons Pharmaceuticals Ltd | Chromone derivatives |
| US3864493A (en) * | 1967-08-17 | 1975-02-04 | Fisons Ltd Felixstowe | Compositions and methods for the prevention of asthmatic symptoms |
| FR7513M (enExample) * | 1967-11-20 | 1969-12-15 | ||
| US3885038A (en) * | 1971-08-23 | 1975-05-20 | Syntex Inc | Method of using substituted xanthone carboxylic acid |
| US3883653A (en) * | 1972-10-24 | 1975-05-13 | Pfizer | Method of preventing asthmatic symptoms |
| US3879544A (en) * | 1973-05-09 | 1975-04-22 | Carter Wallace | Method for suppressing histamine release |
-
1973
- 1973-04-19 GB GB1887673A patent/GB1432809A/en not_active Expired
-
1974
- 1974-04-05 IE IE743/74A patent/IE39359B1/xx unknown
- 1974-04-10 ES ES425514A patent/ES425514A1/es not_active Expired
- 1974-04-10 ZM ZM63/74A patent/ZM6374A1/xx unknown
- 1974-04-11 MW MW14/74*UA patent/MW1474A1/xx unknown
- 1974-04-12 IL IL44628A patent/IL44628A/en unknown
- 1974-04-15 US US05/461,267 patent/US3974289A/en not_active Expired - Lifetime
- 1974-04-16 DE DE2418344A patent/DE2418344A1/de active Pending
- 1974-04-16 JP JP49043233A patent/JPS5035170A/ja active Pending
- 1974-04-17 CS CS742754A patent/CS187414B2/cs unknown
- 1974-04-18 FR FR7413487A patent/FR2226177B1/fr not_active Expired
- 1974-04-18 BE BE143381A patent/BE813919A/xx unknown
- 1974-04-18 HU HUBE1196A patent/HU166816B/hu unknown
- 1974-04-18 ZA ZA00742469A patent/ZA742469B/xx unknown
- 1974-04-18 IN IN888/CAL/74A patent/IN139069B/en unknown
- 1974-04-18 DD DD177992A patent/DD111375A5/xx unknown
- 1974-04-19 CH CH547174A patent/CH593964A5/xx not_active IP Right Cessation
- 1974-04-19 SU SU7402021264A patent/SU578000A3/ru active
- 1974-04-19 NL NL7405383A patent/NL7405383A/xx not_active Application Discontinuation
- 1974-04-19 PL PL1974170492A patent/PL96047B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL44628A0 (en) | 1974-06-30 |
| ZM6374A1 (en) | 1974-12-20 |
| ZA742469B (en) | 1975-04-30 |
| CS187414B2 (en) | 1979-01-31 |
| BE813919A (fr) | 1974-10-18 |
| NL7405383A (enExample) | 1974-10-22 |
| DD111375A5 (enExample) | 1975-02-12 |
| MW1474A1 (en) | 1975-05-13 |
| GB1432809A (en) | 1976-04-22 |
| PL96047B1 (pl) | 1977-11-30 |
| US3974289A (en) | 1976-08-10 |
| HU166816B (enExample) | 1975-06-28 |
| FR2226177A1 (enExample) | 1974-11-15 |
| DE2418344A1 (de) | 1974-11-07 |
| FR2226177B1 (enExample) | 1977-11-10 |
| IE39359B1 (en) | 1978-09-27 |
| JPS5035170A (enExample) | 1975-04-03 |
| CH593964A5 (enExample) | 1977-12-30 |
| AU6805974A (en) | 1975-10-23 |
| IL44628A (en) | 1976-12-31 |
| ES425514A1 (es) | 1976-09-01 |
| IN139069B (enExample) | 1976-05-01 |
| IE39359L (en) | 1974-10-19 |
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