GB1352380A - Quinone derivatives - Google Patents
Quinone derivativesInfo
- Publication number
- GB1352380A GB1352380A GB2417671A GB2417671A GB1352380A GB 1352380 A GB1352380 A GB 1352380A GB 2417671 A GB2417671 A GB 2417671A GB 2417671 A GB2417671 A GB 2417671A GB 1352380 A GB1352380 A GB 1352380A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen atom
- general formula
- methyl
- resulting
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004059 quinone derivatives Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- XFWDWSKJNMQVAZ-UHFFFAOYSA-N 4-(2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid Chemical class CC=1C(C=CC(C1CCCC(=O)O)=O)=O XFWDWSKJNMQVAZ-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract 2
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 abstract 1
- GNCJLWPTDPAOPH-UHFFFAOYSA-N 4-(2-hydroxy-6-methylphenyl)-4-oxobutanoic acid Chemical compound OC1=C(C(=O)CCC(=O)O)C(=CC=C1)C GNCJLWPTDPAOPH-UHFFFAOYSA-N 0.000 abstract 1
- JTIQRBSKVBYEJL-UHFFFAOYSA-N 4-(2-hydroxy-6-methylphenyl)butanoic acid Chemical compound OC1=C(C(=CC=C1)C)CCCC(=O)O JTIQRBSKVBYEJL-UHFFFAOYSA-N 0.000 abstract 1
- 229930003427 Vitamin E Natural products 0.000 abstract 1
- 229930003448 Vitamin K Natural products 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000004973 alkali metal peroxides Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 abstract 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019165 vitamin E Nutrition 0.000 abstract 1
- 229940046009 vitamin E Drugs 0.000 abstract 1
- 239000011709 vitamin E Substances 0.000 abstract 1
- 235000019168 vitamin K Nutrition 0.000 abstract 1
- 239000011712 vitamin K Substances 0.000 abstract 1
- 150000003721 vitamin K derivatives Chemical class 0.000 abstract 1
- 229940046010 vitamin k Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C66/00—Quinone carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1352380 2 - Methyl - 3 - (3 - carboxypropyl)- 1,4-benzoquinones TAKEDA YAKUHIN KOGYO KK 19 April 1971 [17 March 1970 18 March 1970 30 July 1970] 24176/71 Heading C2C Novel 2 - methyl - 3 - (3 - carboxypropyl)- 1,4-benzoquinones of the general formula wherein each X is a methyl group or both Xs together form a -CH = CH-CH = CH- group, one of A and A<SP>1</SP> is a hydrogen atom and the other is a C 1-4 alkyl group and R is a hydrogen atom or an alkyl, alkenyl or cycloalkyl group, and when R is a hydrogen atom, pharmaceutically acceptable base addition salts thereof are prepared (a) by reaction of a 2-methyl-1,4- benzoquinone of the general formula with a peroxide of the general formula (b) when R is a hydrogen atom, by reaction of a m-phenol and succinic acid anhydride of the respective general formulae wherein R 1 is a hydrogen atom or a C 1-4 alkyl group and R 2 is a C 1-4 alkyl group corresponding to the C 1-4 alkyl group represented by A or A<SP>1</SP>, followed by reduction of the resulting 3-(2- hydroxy - 6 - methylbenzoyl) - propionic acid of the general formula and oxidation of the resulting 4-(2-hydroxy-6- methyl-phenyl)-butyric acid (the reduction and oxidation steps may also be effected in the reverse order); (c) when R is a hydrogen atom, by hydrolysis of the corresponding compound wherein R is other than a hydrogen atom; and (d) when R is other than a hydrogen atom, by esterification of the corresponding compound wherein R is a hydrogen atom; followed optionally, when R is a hydrogen atom, by salification of the product. Peroxides of the third general formula above are prepared by reaction of compounds of formulae ROOC-CHA<SP>1</SP>-CA=CH 2 and CN-CH 2 -COOR<SP>1</SP>, wherein R<SP>1</SP> is a lower alkyl group, hydrolysis of the resulting nitrile of the general formula halogenation of the resulting glutaric acid of the general formula and treatment of the resulting acid halide of the general formula wherein Y is a halogen atom, with an alkali metal peroxide. Pharmaceutical compositions having Vitamin E, Vitamin K and anti-inflammatory activity comprise, as active ingredient, a 2-methyl-3-(3- carboxypropyl)-1,4-benzoquinone of the first general formula above or, when R is a hydrogen atom, a pharmaceutically acceptable base addition salt thereof, together with a pharmaceutically acceptable carrier and/or diluent.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2249770A JPS4843106B1 (en) | 1970-03-17 | 1970-03-17 | |
| JP2280570A JPS4843342B1 (en) | 1970-03-18 | 1970-03-18 | |
| JP6693870A JPS5010574B1 (en) | 1970-07-30 | 1970-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1352380A true GB1352380A (en) | 1974-05-08 |
Family
ID=27283868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2417671A Expired GB1352380A (en) | 1970-03-17 | 1971-04-19 | Quinone derivatives |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE764384A (en) |
| DE (1) | DE2112147A1 (en) |
| FR (1) | FR2085716B1 (en) |
| GB (1) | GB1352380A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3957836A (en) * | 1973-07-02 | 1976-05-18 | Takeda Chemical Industries, Ltd. | Quinone derivatives |
| JPS5919930B2 (en) * | 1974-05-02 | 1984-05-09 | 武田薬品工業株式会社 | Method for producing quinonic acid derivatives |
| MX9203040A (en) * | 1984-08-01 | 1992-07-31 | Takeda Chemical Industries Ltd | DERIVATIVES OF QUINONA AND PHARMACEUTICAL COMPOSITION THAT CONTAINS THEM. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398418A (en) * | 1943-08-27 | 1946-04-16 | Louis F Fieser | Introduction of organic radicals into quinones |
-
1971
- 1971-03-13 DE DE19712112147 patent/DE2112147A1/en active Pending
- 1971-03-16 FR FR7109165A patent/FR2085716B1/fr not_active Expired
- 1971-03-17 BE BE764384A patent/BE764384A/en not_active IP Right Cessation
- 1971-04-19 GB GB2417671A patent/GB1352380A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2085716B1 (en) | 1975-06-06 |
| DE2112147A1 (en) | 1971-09-30 |
| FR2085716A1 (en) | 1971-12-31 |
| BE764384A (en) | 1971-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1307205A (en) | Isoindoline derivatives | |
| GB1301431A (en) | ||
| IE35424B1 (en) | Cyclopropane derivatives | |
| GB1352380A (en) | Quinone derivatives | |
| GB1513320A (en) | N-propargyl-2-phenylamino-2-imidazolines | |
| GB1228736A (en) | ||
| GB1265279A (en) | ||
| GB1530074A (en) | Rho-acetamidophenol derivatives the preparation thereof and the use of such derivatives as therapeutic agents | |
| GB1252329A (en) | ||
| GB1418172A (en) | 5-haloalkyl- picolinic acid and process of production thereof | |
| GB1500962A (en) | Furo(2,3-d)pyrimidine derivatives | |
| GB1334693A (en) | Acenaphthene derivatives | |
| GB1299247A (en) | Benzofuran derivatives and process for preparing the same | |
| IE36485L (en) | Benzothiophenes. | |
| GB1431279A (en) | Thiazole derivatives and their use as cardiovascular agents | |
| GB1289227A (en) | ||
| SE7408868L (en) | ||
| GB1158264A (en) | Substituted 1,2-Dihydroquinoline-N-Carboxylic Acids and -Thioncarboxylic Acids | |
| GB1467761A (en) | Phenoxypropylamine derivatives and preparation thereof | |
| GB1503626A (en) | Substituted piperazine derivative its preparation and compositions containing it | |
| GB1245155A (en) | NOVEL 5-SUBSTITUTED-gamma-CARBOLINE DERIVATIVES AND THE SALTS THEREOF | |
| GB1382438A (en) | Adamantane and substituted adamantane carboxylic acid esters of chloramphenicol | |
| GB1382586A (en) | 5,11-dihydrodibenzoxa -or thia- zepine derivatives | |
| GB1350645A (en) | Phenylacetic acid derivatives a method for their preparation and the applications thereof | |
| GB1504683A (en) | Pharmaceutical compositions containing substituted pyrimido-quinoline derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |