DE2224706A1 - - Google Patents
Info
- Publication number
- DE2224706A1 DE2224706A1 DE19722224706 DE2224706A DE2224706A1 DE 2224706 A1 DE2224706 A1 DE 2224706A1 DE 19722224706 DE19722224706 DE 19722224706 DE 2224706 A DE2224706 A DE 2224706A DE 2224706 A1 DE2224706 A1 DE 2224706A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- trimethyl
- halides
- phosphorus
- retinyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- -1 Retinyl bromide Chemical compound 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000019155 vitamin A Nutrition 0.000 description 3
- 239000011719 vitamin A Substances 0.000 description 3
- 229940045997 vitamin a Drugs 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/04—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR717118167A FR2138211B1 (enrdf_load_stackoverflow) | 1971-05-19 | 1971-05-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2224706A1 true DE2224706A1 (enrdf_load_stackoverflow) | 1972-12-14 |
| DE2224706B2 DE2224706B2 (de) | 1974-10-31 |
Family
ID=9077310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2224706A Pending DE2224706B2 (de) | 1971-05-19 | 1972-05-19 | Herstellung von Retinylhalogeniden |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010209A1 (de) * | 1978-10-07 | 1980-04-30 | BASF Aktiengesellschaft | N-Benzoyl-retinylamine, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Mittel und die Verwendung dieser Verbindungen bei der Therapie und Prophylaxe von Praekanzerosen und Karzinomen der Haut |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2234284B1 (enrdf_load_stackoverflow) * | 1973-06-25 | 1978-01-13 | Hoffmann La Roche | |
| DE2717737A1 (de) * | 1977-04-21 | 1978-10-26 | Basf Ag | Derivate von 8-dehydro-vitamin-a sowie verfahren zu deren herstellung |
| AU3459300A (en) * | 1999-04-08 | 2000-11-14 | Sumitomo Chemical Company, Limited | Process for the preparation of halogenated compounds |
| US10226536B2 (en) | 2011-11-28 | 2019-03-12 | Case Western Reserve University | Polysaccharide therapeutic conjugates |
| WO2015184453A1 (en) | 2014-05-30 | 2015-12-03 | Case Western Reserve University | Retinylamine derivitives for treatment of ocular disorders |
| US11129845B2 (en) | 2014-06-18 | 2021-09-28 | Case Western Reserve University | Compositions and methods for the delivery of nucleic acids |
| US10925980B2 (en) | 2014-08-04 | 2021-02-23 | Case Western Reserve University | Molecular probes and methods of use |
| US11407786B2 (en) | 2015-06-18 | 2022-08-09 | Case Western Reserve University | Compositions and methods for the delivery of nucleic acids |
| US12060318B2 (en) | 2015-10-09 | 2024-08-13 | Case Western Reserve University | Compositions and methods for the delivery of nucleic acids |
-
1971
- 1971-05-19 FR FR717118167A patent/FR2138211B1/fr not_active Expired
- 1971-05-19 ES ES402985A patent/ES402985A1/es not_active Expired
-
1972
- 1972-05-10 NL NL7206337A patent/NL7206337A/xx unknown
- 1972-05-17 IL IL39462A patent/IL39462A/xx unknown
- 1972-05-17 JP JP47049018A patent/JPS5233628B1/ja active Pending
- 1972-05-18 GB GB2336872A patent/GB1334980A/en not_active Expired
- 1972-05-18 BE BE783671A patent/BE783671A/xx unknown
- 1972-05-18 CH CH739672A patent/CH532567A/fr not_active IP Right Cessation
- 1972-05-19 IT IT24601/72A patent/IT1043881B/it active
- 1972-05-19 DE DE2224706A patent/DE2224706B2/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010209A1 (de) * | 1978-10-07 | 1980-04-30 | BASF Aktiengesellschaft | N-Benzoyl-retinylamine, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Mittel und die Verwendung dieser Verbindungen bei der Therapie und Prophylaxe von Praekanzerosen und Karzinomen der Haut |
Also Published As
| Publication number | Publication date |
|---|---|
| ES402985A1 (es) | 1975-04-16 |
| FR2138211A1 (enrdf_load_stackoverflow) | 1973-01-05 |
| NL7206337A (enrdf_load_stackoverflow) | 1972-11-21 |
| DE2224706B2 (de) | 1974-10-31 |
| IT1043881B (it) | 1980-02-29 |
| IL39462A0 (en) | 1972-07-26 |
| JPS5233628B1 (enrdf_load_stackoverflow) | 1977-08-30 |
| IL39462A (en) | 1974-11-29 |
| FR2138211B1 (enrdf_load_stackoverflow) | 1973-05-11 |
| BE783671A (fr) | 1972-11-20 |
| CH532567A (fr) | 1973-01-15 |
| GB1334980A (en) | 1973-10-24 |
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