SU1072805A3 - Способ получени производных флавана или их солей - Google Patents
Способ получени производных флавана или их солей Download PDFInfo
- Publication number
- SU1072805A3 SU1072805A3 SU792740772A SU2740772A SU1072805A3 SU 1072805 A3 SU1072805 A3 SU 1072805A3 SU 792740772 A SU792740772 A SU 792740772A SU 2740772 A SU2740772 A SU 2740772A SU 1072805 A3 SU1072805 A3 SU 1072805A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxy
- methoxy
- methyl
- dimethoxy
- dioxo
- Prior art date
Links
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 239000011701 zinc Substances 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- -1 cyano, hydroxy Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 229910000497 Amalgam Inorganic materials 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims 1
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
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- 241000700605 Viruses Species 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 206010039105 Rhinoviral infections Diseases 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
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- 239000000203 mixture Substances 0.000 description 23
- 229960000583 acetic acid Drugs 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- SJERGDGMNSFZJB-UHFFFAOYSA-N 4,6-dichloro-2-phenyl-3,4-dihydro-2h-chromene Chemical compound O1C2=CC=C(Cl)C=C2C(Cl)CC1C1=CC=CC=C1 SJERGDGMNSFZJB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 230000009467 reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- RBTRZZQLGUWCOO-UHFFFAOYSA-N 4-chloro-2-phenyl-3,4-dihydro-2H-chromene Chemical compound ClC1CC(OC2=CC=CC=C12)C1=CC=CC=C1 RBTRZZQLGUWCOO-UHFFFAOYSA-N 0.000 description 2
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- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JYZJYCJGHCCJLZ-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-chromen-4-amine Chemical group O1C2=CC=CC=C2C(N)CC1C1=CC=CC=C1 JYZJYCJGHCCJLZ-UHFFFAOYSA-N 0.000 description 1
- VMITYLJHUKSVIC-UHFFFAOYSA-N 3-fluoro-1h-indole Chemical compound C1=CC=C2C(F)=CNC2=C1 VMITYLJHUKSVIC-UHFFFAOYSA-N 0.000 description 1
- XOOVSOZTYUPBIY-UHFFFAOYSA-N 4-chloro-2-phenyl-4H-chromen-3-one Chemical compound ClC1C(C(OC2=CC=CC=C12)C1=CC=CC=C1)=O XOOVSOZTYUPBIY-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- FEQVSCDUIDPJJD-UHFFFAOYSA-N 4-methyl-2-phenyl-3,4-dihydro-2h-chromene Chemical compound O1C2=CC=CC=C2C(C)CC1C1=CC=CC=C1 FEQVSCDUIDPJJD-UHFFFAOYSA-N 0.000 description 1
- 102100035475 Blood vessel epicardial substance Human genes 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VDAUBODBRFMTDQ-UHFFFAOYSA-N C1C(OC2=C(C1Cl)C(=CC=C2)Cl)C3=CC=CC=C3 Chemical compound C1C(OC2=C(C1Cl)C(=CC=C2)Cl)C3=CC=CC=C3 VDAUBODBRFMTDQ-UHFFFAOYSA-N 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- 101001094636 Homo sapiens Blood vessel epicardial substance Proteins 0.000 description 1
- 101000608194 Homo sapiens Pyrin domain-containing protein 1 Proteins 0.000 description 1
- 101000595404 Homo sapiens Ribonucleases P/MRP protein subunit POP1 Proteins 0.000 description 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 description 1
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- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- 235000003976 Ruta Nutrition 0.000 description 1
- 240000005746 Ruta graveolens Species 0.000 description 1
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000011543 agarose gel Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- 231100000673 dose–response relationship Toxicity 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
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- 210000004080 milk Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
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- 235000005806 ruta Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1025178 | 1978-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1072805A3 true SU1072805A3 (ru) | 1984-02-07 |
Family
ID=9964425
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792740772A SU1072805A3 (ru) | 1978-03-15 | 1979-03-14 | Способ получени производных флавана или их солей |
| SU802912758A SU986296A3 (ru) | 1978-03-15 | 1980-04-25 | Способ получени производных флавана или их солей |
| SU802912759A SU991948A3 (ru) | 1978-03-15 | 1980-04-25 | Способ получени производных флавана или их солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802912758A SU986296A3 (ru) | 1978-03-15 | 1980-04-25 | Способ получени производных флавана или их солей |
| SU802912759A SU991948A3 (ru) | 1978-03-15 | 1980-04-25 | Способ получени производных флавана или их солей |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4461907A (enExample) |
| EP (2) | EP0051061A3 (enExample) |
| JP (1) | JPS54130575A (enExample) |
| AR (2) | AR223478A1 (enExample) |
| AT (1) | AT366681B (enExample) |
| AU (1) | AU529313B2 (enExample) |
| CA (1) | CA1193273A (enExample) |
| CS (1) | CS231964B2 (enExample) |
| DD (1) | DD142340A5 (enExample) |
| DK (1) | DK105379A (enExample) |
| EG (1) | EG14189A (enExample) |
| ES (3) | ES478605A1 (enExample) |
| FI (1) | FI790863A7 (enExample) |
| GR (1) | GR67250B (enExample) |
| HU (2) | HU187755B (enExample) |
| IL (1) | IL56871A (enExample) |
| IN (2) | IN150229B (enExample) |
| IT (1) | IT1116848B (enExample) |
| MC (1) | MC1254A1 (enExample) |
| MY (1) | MY8500223A (enExample) |
| NO (3) | NO154167C (enExample) |
| NZ (1) | NZ189906A (enExample) |
| OA (1) | OA06289A (enExample) |
| PH (1) | PH18415A (enExample) |
| PL (3) | PL122049B1 (enExample) |
| PT (1) | PT69349A (enExample) |
| RO (4) | RO82173B (enExample) |
| SU (3) | SU1072805A3 (enExample) |
| YU (3) | YU61679A (enExample) |
| ZA (1) | ZA791198B (enExample) |
| ZM (1) | ZM2479A1 (enExample) |
| ZW (1) | ZW5979A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ193316A (en) * | 1979-04-10 | 1984-07-31 | Hoffmann La Roche | 3-alkoxyflavone derivatives and pharmaceutical compositions |
| US4588733A (en) * | 1984-10-19 | 1986-05-13 | Merrell Dow Pharmaceuticals Inc. | 2-phenylpyrano[2,3-b]pyridines and their use in inhibiting viruses |
| US4758679A (en) * | 1986-07-18 | 1988-07-19 | Pennwalt Corporation | Preparation of 7-(3-(propylamino)-2-hydroxypropoxy)flavone |
| LU86715A1 (fr) * | 1986-12-16 | 1988-07-14 | Oreal | Composition cosmetique contenant des derives hydroxyles de chalcone et son utilisation pour la protection de la peau et des cheveux contre les radiations lumineuses,nouveaux derives hydroxyles de chalcone utilises et leur procede de preparation |
| KR0139296B1 (ko) * | 1988-11-21 | 1998-05-15 | 가와무라 시게꾸니 | 칼콘 유도체 및 그 제조 방법 |
| US5063244A (en) * | 1990-07-30 | 1991-11-05 | Development Center For Biotechnology | Process for the isolation of antifungal agents (5-methoxy-7-hydroxyflavan) from dragon's blood resin and its use in agriculture |
| US5276058A (en) * | 1993-06-09 | 1994-01-04 | Nippon Hypox Laboratories Incorporated | 3,4-dihydroxychalcone derivatives |
| IL118657A0 (en) * | 1996-06-14 | 1996-10-16 | Arad Dorit | Inhibitors for picornavirus proteases |
| IL122591A0 (en) | 1997-12-14 | 1998-06-15 | Arad Dorit | Pharmaceutical compositions comprising cystein protease inhibitors |
| AU6174900A (en) | 1999-07-08 | 2001-01-30 | Patrick T. Prendergast | Use of flavones, coumarins and related compounds to treat infections |
| US6677350B1 (en) | 1999-09-22 | 2004-01-13 | Advanced Life Sciences, Inc. | Beta-fluoroethyl thiourea compounds and use |
| JP4742215B2 (ja) * | 2003-06-23 | 2011-08-10 | Ｊｎｃ株式会社 | クロマン化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 |
| ATE342950T1 (de) * | 2003-06-23 | 2006-11-15 | Chisso Petrochemical Corp | Chromanverbindung, flüssigkristallzusammensetzung enthaltend die verbindung und flüssigkristallanzeigeelement enthaltend die flüssigkristallzusammensetzung |
| JP5128277B2 (ja) | 2004-05-28 | 2013-01-23 | ユニジェン・インコーポレーテッド | 二核酵素の強力な阻害剤としてのジアリールアルカン類 |
| KR101233223B1 (ko) * | 2004-12-21 | 2013-02-14 | 제이엔씨 석유 화학 주식회사 | 크로만환을 가지는 액정 화합물, 액정 조성물 및 이 액정조성물을 함유하는 액정 표시소자 |
| JP5126942B2 (ja) * | 2006-12-26 | 2013-01-23 | 静岡県公立大学法人 | ５，７−ジデオキシエピガロカテキンガレート、その製法及び抗インフルエンザウイルス剤 |
| EP2981260B1 (en) * | 2013-04-04 | 2021-01-13 | Sphaera Pharma Pvt. Ltd. | Novel analogues of epicatechin and related polyphenols |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1518006A1 (de) * | 1951-01-28 | 1969-01-16 | Merck Ag E | Verfahren zur Herstellung von wasserloeslichen Flavanoidderivaten |
| FR1221869A (fr) * | 1959-01-15 | 1960-06-07 | Coupin Lab | Procédé de préparation de dérivés solubles dans l'eau à partir des glucosides flavanoniques |
| ES265050A1 (es) * | 1960-02-23 | 1961-06-16 | Orsymonde Ltd | Procedimiento de preparación de derivados insaturados de la trihidroxiacetofenona |
| CH473114A (de) * | 1963-08-28 | 1969-05-31 | Merck Ag E | Verfahren zur Herstellung von substituierten Flavanoiden |
| DE1493976C3 (de) * | 1964-01-18 | 1973-09-13 | Merck Patent Gmbh, 6100 Darmstadt | Substituierte Flavandenvate sowie Verfahren zu ihrer Herstellung |
| US3499763A (en) * | 1967-05-01 | 1970-03-10 | Ibm | Bis phenols as high opacity diazotype couplers |
| FR1583930A (enExample) * | 1968-06-27 | 1969-12-05 | ||
| GB1283981A (en) * | 1969-03-05 | 1972-08-02 | Orsymonde | 2,4,6-trihydroxy chalcone derivatives |
| US3678044A (en) * | 1970-10-22 | 1972-07-18 | Chevron Res | Substituted flavanones |
| NZ192641A (en) * | 1979-01-26 | 1984-10-19 | Hoffmann La Roche | Substituted acetophenones and pharmaceutical compositions |
-
1979
- 1979-03-14 GR GR58604A patent/GR67250B/el unknown
- 1979-03-14 CA CA000323442A patent/CA1193273A/en not_active Expired
- 1979-03-14 YU YU00616/79A patent/YU61679A/xx unknown
- 1979-03-14 DD DD79211585A patent/DD142340A5/de unknown
- 1979-03-14 AR AR275805A patent/AR223478A1/es active
- 1979-03-14 PL PL1979226122A patent/PL122049B1/pl unknown
- 1979-03-14 DK DK105379A patent/DK105379A/da not_active Application Discontinuation
- 1979-03-14 NZ NZ189906A patent/NZ189906A/en unknown
- 1979-03-14 IN IN248/CAL/79A patent/IN150229B/en unknown
- 1979-03-14 RO RO104246A patent/RO82173B/ro unknown
- 1979-03-14 ZA ZA791198A patent/ZA791198B/xx unknown
- 1979-03-14 NO NO790871A patent/NO154167C/no unknown
- 1979-03-14 PT PT69349A patent/PT69349A/pt unknown
- 1979-03-14 JP JP2984079A patent/JPS54130575A/ja active Pending
- 1979-03-14 FI FI790863A patent/FI790863A7/fi not_active Application Discontinuation
- 1979-03-14 SU SU792740772A patent/SU1072805A3/ru active
- 1979-03-14 RO RO7996886A patent/RO78419A/ro unknown
- 1979-03-14 ZM ZM24/79A patent/ZM2479A1/xx unknown
- 1979-03-14 PL PL1979226121A patent/PL121969B1/pl unknown
- 1979-03-14 AT AT0191879A patent/AT366681B/de not_active IP Right Cessation
- 1979-03-14 CS CS791690A patent/CS231964B2/cs unknown
- 1979-03-14 ZW ZW59/79A patent/ZW5979A1/xx unknown
- 1979-03-14 PH PH22283A patent/PH18415A/en unknown
- 1979-03-14 MC MC791370A patent/MC1254A1/fr unknown
- 1979-03-14 ES ES478605A patent/ES478605A1/es not_active Expired
- 1979-03-14 IT IT48347/79A patent/IT1116848B/it active
- 1979-03-14 RO RO111323A patent/RO86258B/ro unknown
- 1979-03-14 EP EP82100169A patent/EP0051061A3/en not_active Ceased
- 1979-03-14 PL PL21411579A patent/PL214115A1/xx unknown
- 1979-03-14 EP EP79100768A patent/EP0004579B1/en not_active Expired
- 1979-03-14 EG EG166/79A patent/EG14189A/xx active
- 1979-03-14 AU AU45108/79A patent/AU529313B2/en not_active Ceased
- 1979-03-14 RO RO104245A patent/RO82526B/ro unknown
- 1979-03-14 HU HU79WE595A patent/HU187755B/hu unknown
- 1979-03-14 HU HU832536A patent/HUT35173A/hu unknown
- 1979-03-14 IL IL56871A patent/IL56871A/xx unknown
- 1979-07-07 OA OA56842A patent/OA06289A/xx unknown
- 1979-07-24 ES ES482788A patent/ES482788A1/es not_active Expired
- 1979-07-24 ES ES482787A patent/ES482787A1/es not_active Expired
-
1980
- 1980-04-25 SU SU802912758A patent/SU986296A3/ru active
- 1980-04-25 SU SU802912759A patent/SU991948A3/ru active
- 1980-06-10 AR AR281366A patent/AR225175A1/es active
-
1981
- 1981-06-29 IN IN708/CAL/81A patent/IN151598B/en unknown
-
1982
- 1982-07-14 US US06/398,211 patent/US4461907A/en not_active Expired - Fee Related
- 1982-12-08 YU YU02714/82A patent/YU271482A/xx unknown
- 1982-12-08 YU YU02715/82A patent/YU271582A/xx unknown
-
1984
- 1984-02-20 NO NO840627A patent/NO840627L/no unknown
- 1984-02-20 NO NO840626A patent/NO840626L/no unknown
-
1985
- 1985-12-30 MY MY223/85A patent/MY8500223A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| 1. Эльдерфильд Р, Те:героциклические соединени . М., ИЛ, 1954, т. 2, с. 272. * |
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