GB1424004A - Production of hydroquinone derivatives - Google Patents
Production of hydroquinone derivativesInfo
- Publication number
- GB1424004A GB1424004A GB5774072A GB5774072A GB1424004A GB 1424004 A GB1424004 A GB 1424004A GB 5774072 A GB5774072 A GB 5774072A GB 5774072 A GB5774072 A GB 5774072A GB 1424004 A GB1424004 A GB 1424004A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- methyl
- hydroquinone
- phytyl
- dimethoxy
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 abstract 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 229930003448 Vitamin K Natural products 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001649 bromium compounds Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000006196 deacetylation Effects 0.000 abstract 1
- 238000003381 deacetylation reaction Methods 0.000 abstract 1
- -1 geranyl bromides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 150000002815 nickel Chemical class 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000006699 reductive acetylation reaction Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1424004 Hydroquinone derivatives; vitamin K EISAI CO Ltd 14 Dec 1972 [16 Feb 1972 18 Feb 1972] 57740/72 Headings C2C and C2V A process for preparing a hydroquinone derivative of the Formula I wherein R<SP>1</SP> and R<SP>2</SP> are methoxy groups or, together with the carbon atoms to which they are attached, constitute a benzene ring; A and B are hydrogen atoms or together a direct bond and n is 0 or an integer from 1 to 9 comprises condensing a 2-halo-3-methyl-1,4-hydroquinone diacetate of the Formula II wherein R<SP>1</SP> and R<SP>2</SP> have the meanings already given and X is a halogen atom with an allyl halonickel #-complex of the Formula III where A, B, X and n have the meanings already given. The invention also comprises the compounds of Formula II defined above. The product of Formula I may be converted to the corresponding benzoquinone derivative by deacetylation and oxidation. The examples describe the preparation of the diacetates of dihydrovitamins K 1 , K 2(20) and K 2(5) , and of 2,3-dimethoxy-5-methyl-6-prenyl-, -6-geranyl-, - 6 - nonoprenyl -, - 6 - decaprenyl - and - 6 - phytyl-1,4-hydroquinones. The compound of Formula II may be prepared by reductive acetylation from the corresponding benzoquinone, e.g. 2,3-dimethoxy-5-methyl-6-bromo- 1,4-dihydroquinone diacetate is obtained by reacting the corresponding benzoquinone with acetic anhydride and zinc dust. Nickel complexes used in the process are obtained by reacting appropriate bromides, e.g. phytyl and geranyl bromides, with a benzene solution of nickel carbonyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1558372A JPS5029468B2 (en) | 1972-02-16 | 1972-02-16 | |
| JP1644972A JPS507063B2 (en) | 1972-02-18 | 1972-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1424004A true GB1424004A (en) | 1976-02-04 |
Family
ID=26351760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5774072A Expired GB1424004A (en) | 1972-02-16 | 1972-12-14 | Production of hydroquinone derivatives |
Country Status (8)
| Country | Link |
|---|---|
| AR (2) | AR197481A1 (en) |
| CH (1) | CH575904A5 (en) |
| DE (1) | DE2258520A1 (en) |
| ES (2) | ES409092A1 (en) |
| FR (1) | FR2172087B1 (en) |
| GB (1) | GB1424004A (en) |
| HU (1) | HU165681B (en) |
| NL (1) | NL7217109A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015018858A1 (en) * | 2013-08-08 | 2015-02-12 | Kappa Bioscience As | Compositions comprising vitamin k derivatives and salts |
| US10159687B2 (en) | 2012-03-02 | 2018-12-25 | Kappa Bioscience As | Prodrugs of vitamin K |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4466981A (en) * | 1982-10-27 | 1984-08-21 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
| IT1284873B1 (en) * | 1996-07-26 | 1998-05-22 | Idi Farmaceutici Spa | STABLE DERIVATIVES OF UBIQUINOL PROCEDURES FOR THEIR PRODUCTION AND PHARMACEUTICAL USE |
-
1972
- 1972-11-23 CH CH1706872A patent/CH575904A5/xx not_active IP Right Cessation
- 1972-11-29 DE DE19722258520 patent/DE2258520A1/en not_active Ceased
- 1972-11-29 ES ES409092A patent/ES409092A1/en not_active Expired
- 1972-11-30 FR FR7242671A patent/FR2172087B1/fr not_active Expired
- 1972-12-14 GB GB5774072A patent/GB1424004A/en not_active Expired
- 1972-12-15 NL NL7217109A patent/NL7217109A/xx not_active Application Discontinuation
- 1972-12-15 AR AR24568972A patent/AR197481A1/en active
- 1972-12-20 HU HUEI000449 patent/HU165681B/hu unknown
-
1974
- 1974-03-27 AR AR25300174A patent/AR199334A1/en active
-
1975
- 1975-04-30 ES ES437353A patent/ES437353A1/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10159687B2 (en) | 2012-03-02 | 2018-12-25 | Kappa Bioscience As | Prodrugs of vitamin K |
| WO2015018858A1 (en) * | 2013-08-08 | 2015-02-12 | Kappa Bioscience As | Compositions comprising vitamin k derivatives and salts |
| CN105492073A (en) * | 2013-08-08 | 2016-04-13 | 卡帕生物科学研究院 | Provitamins |
| AU2014304510B2 (en) * | 2013-08-08 | 2017-03-16 | Kappa Bioscience As | Compositions comprising vitamin K derivatives and salts |
| CN105492073B (en) * | 2013-08-08 | 2019-06-28 | 卡帕生物科学研究院 | Provitamin |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2172087B1 (en) | 1977-01-28 |
| AR197481A1 (en) | 1974-04-15 |
| DE2258520A1 (en) | 1973-08-23 |
| CH575904A5 (en) | 1976-05-31 |
| FR2172087A1 (en) | 1973-09-28 |
| AR199334A1 (en) | 1974-08-23 |
| ES409092A1 (en) | 1976-03-01 |
| NL7217109A (en) | 1973-08-20 |
| HU165681B (en) | 1974-10-28 |
| ES437353A1 (en) | 1977-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19921213 |