UA79448C2 - Derivatives of 3-aryl-2,5-dihydroxy-1,4-benzoquinone, method for synthesis and pharmaceutical composition - Google Patents
Derivatives of 3-aryl-2,5-dihydroxy-1,4-benzoquinone, method for synthesis and pharmaceutical composition Download PDFInfo
- Publication number
- UA79448C2 UA79448C2 UA20040907252A UA20040907252A UA79448C2 UA 79448 C2 UA79448 C2 UA 79448C2 UA 20040907252 A UA20040907252 A UA 20040907252A UA 20040907252 A UA20040907252 A UA 20040907252A UA 79448 C2 UA79448 C2 UA 79448C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- branched
- linear
- benzoquinone
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 45
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 229940005561 1,4-benzoquinone Drugs 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- -1 benzhydryl group Chemical group 0.000 claims abstract description 15
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 15
- 125000002252 acyl group Chemical group 0.000 claims abstract description 13
- IIBSKZLEQXFSRM-UHFFFAOYSA-N 2,5-dihydroxy-3-(4-methoxyphenyl)-6-naphthalen-2-ylcyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(OC)=CC=C1C1=C(O)C(=O)C(C=2C=C3C=CC=CC3=CC=2)=C(O)C1=O IIBSKZLEQXFSRM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- HEMZKGQLXULANP-UHFFFAOYSA-N 2,5-dihydroxy-3-naphthalen-2-yl-6-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(O)=C(C=2C=C3C=CC=CC3=CC=2)C(=O)C(O)=C1C1=CC=CC=C1 HEMZKGQLXULANP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- VTFRCXNKWWTVCR-UHFFFAOYSA-N 2,5-dihydroxy-3-(4-methoxyphenyl)-6-(2-phenylethenyl)cyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(OC)=CC=C1C1=C(O)C(=O)C(C=CC=2C=CC=CC=2)=C(O)C1=O VTFRCXNKWWTVCR-UHFFFAOYSA-N 0.000 claims description 4
- DCBQNQJIQLNPOO-UHFFFAOYSA-N 2-(4-chlorophenyl)-3,6-dihydroxy-5-naphthalen-2-ylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(O)=C(C=2C=C3C=CC=CC3=CC=2)C(=O)C(O)=C1C1=CC=C(Cl)C=C1 DCBQNQJIQLNPOO-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- UYGHUZALAJWNDW-UHFFFAOYSA-N 2-(4-bromophenyl)-3,6-dihydroxy-5-naphthalen-2-ylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(O)=C(C=2C=C3C=CC=CC3=CC=2)C(=O)C(O)=C1C1=CC=C(Br)C=C1 UYGHUZALAJWNDW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000003831 deregulation Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- PCMWVXNZRQRPBY-UHFFFAOYSA-N 2-(4-bromophenyl)-3,6-dihydroxy-5-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(O)=C(C=2C=CC=CC=2)C(=O)C(O)=C1C1=CC=C(Br)C=C1 PCMWVXNZRQRPBY-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 239000003472 antidiabetic agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 29
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- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 15
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- 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
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0201409A FR2835523B1 (fr) | 2002-02-06 | 2002-02-06 | Nouveaux derives de 3-aryl-2,5-dihydroxy-1,4-benzoquinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2003/000331 WO2003066561A1 (fr) | 2002-02-06 | 2003-02-04 | Nouveaux derives de 3-aryl-2,5-dihydroxy-1,4-benzoquinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79448C2 true UA79448C2 (en) | 2007-06-25 |
Family
ID=27619936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040907252A UA79448C2 (en) | 2002-02-06 | 2003-04-02 | Derivatives of 3-aryl-2,5-dihydroxy-1,4-benzoquinone, method for synthesis and pharmaceutical composition |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20050085644A1 (es) |
| EP (1) | EP1472208A1 (es) |
| JP (1) | JP4098248B2 (es) |
| KR (1) | KR100605805B1 (es) |
| CN (1) | CN1274655C (es) |
| AR (1) | AR038397A1 (es) |
| AU (1) | AU2003226860B9 (es) |
| BR (1) | BR0307465A (es) |
| CA (1) | CA2474533A1 (es) |
| EA (1) | EA006775B1 (es) |
| FR (1) | FR2835523B1 (es) |
| GE (1) | GEP20063900B (es) |
| HK (1) | HK1078566A1 (es) |
| MA (1) | MA27103A1 (es) |
| MX (1) | MXPA04007684A (es) |
| NO (1) | NO20043532L (es) |
| NZ (1) | NZ534099A (es) |
| PL (1) | PL370773A1 (es) |
| UA (1) | UA79448C2 (es) |
| WO (1) | WO2003066561A1 (es) |
| ZA (1) | ZA200405446B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058846B (zh) * | 2013-01-17 | 2014-07-30 | 福州大学 | 一种源于棘孢曲霉的苯醌衍生物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3586910T2 (de) * | 1984-01-26 | 1993-05-19 | Otsuka Pharma Co Ltd | 1,4-benzochinon-derivate und benzol-derivate und verfahren zu ihrer herstellung. |
| US7057052B2 (en) * | 2002-09-26 | 2006-06-06 | Duke University | Heterocyclic quinones as pharmaceutical agents |
-
2002
- 2002-02-06 FR FR0201409A patent/FR2835523B1/fr not_active Expired - Fee Related
-
2003
- 2003-02-04 KR KR1020047012152A patent/KR100605805B1/ko not_active IP Right Cessation
- 2003-02-04 EP EP03737340A patent/EP1472208A1/fr not_active Withdrawn
- 2003-02-04 WO PCT/FR2003/000331 patent/WO2003066561A1/fr active Application Filing
- 2003-02-04 PL PL03370773A patent/PL370773A1/xx unknown
- 2003-02-04 MX MXPA04007684A patent/MXPA04007684A/es not_active Application Discontinuation
- 2003-02-04 GE GEAP8395A patent/GEP20063900B/en unknown
- 2003-02-04 CN CNB038031779A patent/CN1274655C/zh not_active Expired - Fee Related
- 2003-02-04 US US10/503,527 patent/US20050085644A1/en not_active Abandoned
- 2003-02-04 CA CA002474533A patent/CA2474533A1/fr not_active Abandoned
- 2003-02-04 JP JP2003565937A patent/JP4098248B2/ja not_active Expired - Fee Related
- 2003-02-04 BR BR0307465-0A patent/BR0307465A/pt not_active IP Right Cessation
- 2003-02-04 NZ NZ534099A patent/NZ534099A/en unknown
- 2003-02-04 EA EA200400992A patent/EA006775B1/ru not_active IP Right Cessation
- 2003-02-04 AU AU2003226860A patent/AU2003226860B9/en not_active Ceased
- 2003-02-06 AR ARP030100368A patent/AR038397A1/es not_active Application Discontinuation
- 2003-04-02 UA UA20040907252A patent/UA79448C2/uk unknown
-
2004
- 2004-07-08 ZA ZA200405446A patent/ZA200405446B/en unknown
- 2004-07-21 MA MA27795A patent/MA27103A1/fr unknown
- 2004-08-24 NO NO20043532A patent/NO20043532L/no not_active Application Discontinuation
-
2005
- 2005-11-21 HK HK05110489A patent/HK1078566A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100605805B1 (ko) | 2006-08-01 |
| EA200400992A1 (ru) | 2005-02-24 |
| CN1628088A (zh) | 2005-06-15 |
| FR2835523A1 (fr) | 2003-08-08 |
| FR2835523B1 (fr) | 2004-04-16 |
| CN1274655C (zh) | 2006-09-13 |
| AR038397A1 (es) | 2005-01-12 |
| GEP20063900B (en) | 2006-08-10 |
| HK1078566A1 (en) | 2006-03-17 |
| AU2003226860A1 (en) | 2003-09-02 |
| JP4098248B2 (ja) | 2008-06-11 |
| AU2003226860B9 (en) | 2008-08-14 |
| CA2474533A1 (fr) | 2003-08-14 |
| MXPA04007684A (es) | 2005-07-13 |
| PL370773A1 (en) | 2005-05-30 |
| JP2005517001A (ja) | 2005-06-09 |
| US20050085644A1 (en) | 2005-04-21 |
| KR20040086352A (ko) | 2004-10-08 |
| NO20043532L (no) | 2004-08-24 |
| EP1472208A1 (fr) | 2004-11-03 |
| AU2003226860B8 (en) | 2008-07-10 |
| MA27103A1 (fr) | 2004-12-20 |
| WO2003066561A1 (fr) | 2003-08-14 |
| BR0307465A (pt) | 2004-11-09 |
| EA006775B1 (ru) | 2006-04-28 |
| AU2003226860B2 (en) | 2008-06-26 |
| ZA200405446B (en) | 2005-07-08 |
| NZ534099A (en) | 2006-09-29 |
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