GB1476300A - Substituted ferrocene compounds and processes for their production - Google Patents
Substituted ferrocene compounds and processes for their productionInfo
- Publication number
- GB1476300A GB1476300A GB5400273A GB5400273A GB1476300A GB 1476300 A GB1476300 A GB 1476300A GB 5400273 A GB5400273 A GB 5400273A GB 5400273 A GB5400273 A GB 5400273A GB 1476300 A GB1476300 A GB 1476300A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- ferrocene
- ring
- choh
- 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
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006214 Clemmensen reduction reaction Methods 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960001138 acetylsalicylic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000004996 alkyl benzenes Chemical class 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 235000019152 folic acid Nutrition 0.000 abstract 1
- 229960000304 folic acid Drugs 0.000 abstract 1
- 239000011724 folic acid Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000005171 halobenzenes Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229940127234 oral contraceptive Drugs 0.000 abstract 1
- 239000003539 oral contraceptive agent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 235000019163 vitamin B12 Nutrition 0.000 abstract 1
- 239000011715 vitamin B12 Substances 0.000 abstract 1
- 235000019154 vitamin C Nutrition 0.000 abstract 1
- 239000011718 vitamin C Substances 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1476300 Ferrocene derivatives FISONS Ltd 12 Nov 1974 [21 Nov 1973 17 July 1974] 54002/73 and 31609/74 Heading C2J The invention comprises compounds of the general formula in which R is alkyl, Cl, Br, a thiophene ring, a ring, a furan ring, phenyl or alkyl. or halophenyl, one of X and Y is -CO-, -CHOH-, or -CH 2 - and the other is an exocyclic C-C bond and A is a C 5 -C 7 unsubstituted cyclic hydrocarbyl group which may be unsaturated at the C atom connected to X and, when saturated and when X is -CO-, may be substituted by -OH on the C atom to which Y is attached, X and Y being attached to adjacent C atoms on the A group. The compounds are prepared by the following processes: (a) when X is a direct bond, A is a cycloalkene group and Y is -CO- either by (1) reacting ferrocene with (usually in the presence of a Lewis acid such as AlCl 3 ) where n is 4, 5 or 6 and R<SP>1</SP> is -CN, -COOH or an acid halide or anhydride thereof and, when R<SP>1</SP> is -CN, hydrolysing the product, or (11) cyclizing and dehydrating under acidic conditions a ferrocene substituted by the group -CO(CH 2 ) n COR; (b) when X is -CO- and A is a saturated cyclic hydrocarbyl group substituted by an -OH group at the C atom to which Y (direct bond) is attached by cyclizing a ferrocene substituted by -CO(CH 2 ) n COR under basic conditions (e.g. ring NaH in dioxan or NaOH in ethanol); (c) when one of X and Y is -CHOH- or -CH 2 - by selective reduction of a compound of the invention obtained by process (a), (b) or (f), usually by using Pd on charcoal at 20-80‹ C. or by use of or a Clemmensen reduction; (d) when one of X and Y is -CO- by selective oxidation of a -CHOH- containing product of process (c), e.g. using CrO 3 .dipyridine complex; (e) when R is phenyl or halo- or alkylphenyl by reacting a ferrocene substituted by the group where R<SP>1</SP> and n are as defined under (a) (i) above with benzene or a halo- or alkylbenzene usually under Friedel-Crafts conditions; and (f) when X is -CO- and A is unsaturated by dehydrating a compound obtained by process (b) using similar conditions to that process but preferably lower reaction temperatures. The compounds have pharmacological properties and may be formulated into pharmaceutical compositions which may also include Vitamins B12 and C, folic acid, aspirin, an anthelmintic or an oral contraceptive.
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5400273A GB1476300A (en) | 1973-11-21 | 1973-11-21 | Substituted ferrocene compounds and processes for their production |
| US05/522,591 US3960911A (en) | 1973-11-21 | 1974-11-11 | Ferrocene compounds and preparation |
| ZA00747218A ZA747218B (en) | 1973-11-21 | 1974-11-11 | Ferrocene compounds |
| IL46027A IL46027A (en) | 1973-11-21 | 1974-11-11 | Organo-metallic compounds their preparation and pharmaceutical compositions containing them |
| BE150463A BE822144A (en) | 1973-11-21 | 1974-11-13 | ORGANOMETALLIC COMPOUNDS |
| DE19742453977 DE2453977A1 (en) | 1973-11-21 | 1974-11-14 | NEW FERROCEN COMPOUNDS AND PROCEDURES FOR THEIR PRODUCTION AND PHARMACEUTICAL COMPOSITIONS |
| FI3307/74A FI330774A (en) | 1973-11-21 | 1974-11-14 | |
| AT922274A AT331260B (en) | 1973-11-21 | 1974-11-18 | PROCESS FOR THE PRODUCTION OF NEW CYCLOALK-SUBSTITUTED FERROCENES |
| DD182456A DD116837A5 (en) | 1973-11-21 | 1974-11-19 | |
| IE2380/74A IE40260B1 (en) | 1973-11-21 | 1974-11-19 | Substituted ferrocene compounds and processes for their production |
| AU75530/74A AU487783B2 (en) | 1973-11-21 | 1974-11-19 | Ferrocene compounds |
| SE7414596A SE7414596L (en) | 1973-11-21 | 1974-11-20 | |
| ZM167/74A ZM16774A1 (en) | 1973-11-21 | 1974-11-20 | Compounds |
| ES432100A ES432100A1 (en) | 1973-11-21 | 1974-11-20 | Ferrocene compounds and preparation |
| NO744183A NO744183L (en) | 1973-11-21 | 1974-11-20 | |
| DK603474AA DK137277B (en) | 1973-11-21 | 1974-11-20 | Analogous process for the preparation of ferrocene compounds. |
| FR7438083A FR2251317B1 (en) | 1973-11-21 | 1974-11-20 | |
| JP49133225A JPS5093951A (en) | 1973-11-21 | 1974-11-21 | |
| CA214,322A CA1032549A (en) | 1973-11-21 | 1974-11-21 | Process for the production of ferrocene derivatives |
| NL7415174A NL7415174A (en) | 1973-11-21 | 1974-11-21 | PROCESS FOR THE PREPARATION OF NEW COMPOUNDS, PROCEDURE FOR MANUFACTURE OF PHARMACEUTICAL PREPARATIONS HEREBY, AND THE PRODUCTS THEREOF. |
| US05/664,280 US4038413A (en) | 1973-11-21 | 1976-03-05 | Treating iron deficiency anaemia |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5400273A GB1476300A (en) | 1973-11-21 | 1973-11-21 | Substituted ferrocene compounds and processes for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1476300A true GB1476300A (en) | 1977-06-10 |
Family
ID=10469651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5400273A Expired GB1476300A (en) | 1973-11-21 | 1973-11-21 | Substituted ferrocene compounds and processes for their production |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE822144A (en) |
| GB (1) | GB1476300A (en) |
| ZA (1) | ZA747218B (en) |
-
1973
- 1973-11-21 GB GB5400273A patent/GB1476300A/en not_active Expired
-
1974
- 1974-11-11 ZA ZA00747218A patent/ZA747218B/en unknown
- 1974-11-13 BE BE150463A patent/BE822144A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE822144A (en) | 1975-05-13 |
| ZA747218B (en) | 1975-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |