DE2453936A1 - Neue ferrocenderivate und ihre herstellung - Google Patents
Neue ferrocenderivate und ihre herstellungInfo
- Publication number
- DE2453936A1 DE2453936A1 DE19742453936 DE2453936A DE2453936A1 DE 2453936 A1 DE2453936 A1 DE 2453936A1 DE 19742453936 DE19742453936 DE 19742453936 DE 2453936 A DE2453936 A DE 2453936A DE 2453936 A1 DE2453936 A1 DE 2453936A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- group
- halogen
- alkyl
- 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
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 11
- -1 benzene compound Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- XZHVCVARDQGDNW-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)CCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound C(C1=CC=CC=C1)(=O)CCCC(=O)[C-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] XZHVCVARDQGDNW-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- UTSNARDLQGCIMM-UHFFFAOYSA-N O=C(CCCCC(=O)[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound O=C(CCCCC(=O)[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2] UTSNARDLQGCIMM-UHFFFAOYSA-N 0.000 claims description 2
- DPSBEOMZLUIDDU-UHFFFAOYSA-N O=C(CCCCCC(=O)[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound O=C(CCCCCC(=O)[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2] DPSBEOMZLUIDDU-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 14
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000012223 aqueous fraction Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AOTRJVGJTAEDHF-UHFFFAOYSA-N FC1=C(C(=O)CCCCC(=O)[C-]2C=CC=C2)C=CC=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound FC1=C(C(=O)CCCCC(=O)[C-]2C=CC=C2)C=CC=C1.[CH-]1C=CC=C1.[Fe+2] AOTRJVGJTAEDHF-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 208000015710 Iron-Deficiency Anemia Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002085 enols Chemical group 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 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 description 2
- 125000000879 imine group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 1
- PBFJJSOMGRSORQ-UHFFFAOYSA-N 2-(2-fluorobenzoyl)pentanoic acid Chemical compound CCCC(C(O)=O)C(=O)C1=CC=CC=C1F PBFJJSOMGRSORQ-UHFFFAOYSA-N 0.000 description 1
- HSLPGPIOOHGFDI-UHFFFAOYSA-N 2-(thiophene-2-carbonyl)pentanoic acid Chemical compound CCCC(C(O)=O)C(=O)C1=CC=CS1 HSLPGPIOOHGFDI-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- IZOQMUVIDMLRDC-UHFFFAOYSA-N 5-aceto valeric acid Chemical compound CC(=O)CCCCC(O)=O IZOQMUVIDMLRDC-UHFFFAOYSA-N 0.000 description 1
- SHKWSBAVRQZYLE-UHFFFAOYSA-N 5-oxo-5-phenylpentanoic acid Chemical compound OC(=O)CCCC(=O)C1=CC=CC=C1 SHKWSBAVRQZYLE-UHFFFAOYSA-N 0.000 description 1
- OICMCVXBSRBNGJ-UHFFFAOYSA-N 5-oxo-5-phenylpentanoyl chloride Chemical compound ClC(=O)CCCC(=O)C1=CC=CC=C1 OICMCVXBSRBNGJ-UHFFFAOYSA-N 0.000 description 1
- WTAIFOPOCXTVCX-UHFFFAOYSA-N 6-(4-chlorophenyl)-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)C1=CC=C(Cl)C=C1 WTAIFOPOCXTVCX-UHFFFAOYSA-N 0.000 description 1
- WLDBSYWPZJIASN-UHFFFAOYSA-N 6-(4-chlorophenyl)-6-oxohexanoyl chloride Chemical compound ClC(=O)CCCCC(=O)C1=CC=C(Cl)C=C1 WLDBSYWPZJIASN-UHFFFAOYSA-N 0.000 description 1
- IOWKEASJENDYLT-UHFFFAOYSA-N 6-oxo-6-thiophen-2-ylhexanoic acid Chemical compound OC(=O)CCCCC(=O)C1=CC=CS1 IOWKEASJENDYLT-UHFFFAOYSA-N 0.000 description 1
- RNOOCFGBFIPUMQ-UHFFFAOYSA-N 6-oxoheptanoyl chloride Chemical compound CC(=O)CCCCC(Cl)=O RNOOCFGBFIPUMQ-UHFFFAOYSA-N 0.000 description 1
- VREAMNSKDRPUTE-UHFFFAOYSA-N 7,7-dimethyl-6-oxooctanoyl chloride Chemical compound CC(C)(C)C(=O)CCCCC(Cl)=O VREAMNSKDRPUTE-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- OSAHCBHKCKPJGI-UHFFFAOYSA-N 7-keto-n-caprylic acid Chemical compound CC(=O)CCCCCC(O)=O OSAHCBHKCKPJGI-UHFFFAOYSA-N 0.000 description 1
- DOQWHEUDAHLEPT-UHFFFAOYSA-N 7-oxo-7-phenylheptanoic acid Chemical compound OC(=O)CCCCCC(=O)C1=CC=CC=C1 DOQWHEUDAHLEPT-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- JXZYDCXHRDLMKK-UHFFFAOYSA-N C1(=C(C(=CC(=C1)C)C)C(=O)C1C(CC1)C(=O)[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound C1(=C(C(=CC(=C1)C)C)C(=O)C1C(CC1)C(=O)[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2] JXZYDCXHRDLMKK-UHFFFAOYSA-N 0.000 description 1
- FDZVLBDSKRSYAG-UHFFFAOYSA-N CC(C(CCCCC(=O)[C-]1C=CC=C1)=O)(C)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound CC(C(CCCCC(=O)[C-]1C=CC=C1)=O)(C)C.[CH-]1C=CC=C1.[Fe+2] FDZVLBDSKRSYAG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KXKHSTAYZOCKDR-UHFFFAOYSA-N ClC1=CC=C(C(=O)CCCCC(=O)[C-]2C=CC=C2)C=C1.[CH-]1C=CC=C1.[Fe+2] Chemical compound ClC1=CC=C(C(=O)CCCCC(=O)[C-]2C=CC=C2)C=C1.[CH-]1C=CC=C1.[Fe+2] KXKHSTAYZOCKDR-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 102000008857 Ferritin Human genes 0.000 description 1
- 238000008416 Ferritin Methods 0.000 description 1
- 108050000784 Ferritin Proteins 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 206010022971 Iron Deficiencies Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 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 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- AYNFBLPVIMCKKQ-UHFFFAOYSA-N [Fe].c1cccc1.C=CC(=O)c1cccc1 Chemical compound [Fe].c1cccc1.C=CC(=O)c1cccc1 AYNFBLPVIMCKKQ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000003173 antianemic agent Substances 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- FDJOLVPMNUYSCM-UVKKECPRSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7, Chemical compound [Co+3].N#[C-].C1([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)[N-]\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O FDJOLVPMNUYSCM-UVKKECPRSA-L 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LXGKRVAPVVIDQW-UHFFFAOYSA-N cyclopenta-1,3-diene;1-cyclopenta-1,3-dien-1-ylbutan-1-one;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.CCCC(=O)C1=CC=C[CH-]1 LXGKRVAPVVIDQW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000039 preparative column chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 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 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5400373 | 1973-11-21 | ||
| GB3160874 | 1974-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2453936A1 true DE2453936A1 (de) | 1975-05-28 |
Family
ID=26260995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742453936 Pending DE2453936A1 (de) | 1973-11-21 | 1974-11-14 | Neue ferrocenderivate und ihre herstellung |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3966783A (enExample) |
| JP (1) | JPS5093950A (enExample) |
| DE (1) | DE2453936A1 (enExample) |
| FR (1) | FR2251318A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377986A1 (fr) * | 1977-01-22 | 1978-08-18 | Bayer Ag | Engrais pour l'apport de fer aux vegetaux |
| DE2711546A1 (de) | 1977-03-17 | 1978-09-21 | Bayer Ag | Insektizide und akarizide mittel |
| EP0004894A1 (de) * | 1978-04-13 | 1979-10-31 | Bayer Ag | Düngemittel zur Versorgung von Pflanzen mit Eisen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2623487A1 (de) * | 1976-05-26 | 1977-12-15 | Hoechst Ag | Ferrocenderivate und verfahren zu ihrer herstellung |
| DE2623486C2 (de) * | 1976-05-26 | 1982-12-30 | Hoechst Ag, 6000 Frankfurt | 3.5.5-Trimethylhexanoyl-ferrocen, Verfahren zu seiner Herstellung und pharmazeutische Präparate |
| US4794226A (en) * | 1983-05-26 | 1988-12-27 | Metcal, Inc. | Self-regulating porous heater device |
| US5073625A (en) * | 1983-05-26 | 1991-12-17 | Metcal, Inc. | Self-regulating porous heating device |
| EP0336538A1 (en) * | 1988-02-24 | 1989-10-11 | The British Petroleum Company p.l.c. | Process for preparing chiral sulphoxides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2988562A (en) * | 1953-04-29 | 1961-06-13 | Du Pont | Process for preparing a monoacyl dicyclopentadienyl iron |
| US2810737A (en) * | 1953-07-01 | 1957-10-22 | Du Pont | Dicyclopentadienyl group viii metal compounds having an alpha-hydroxyalkyl substituent on one or both of the cyclopentadienyl rings |
| US2875223A (en) * | 1954-08-18 | 1959-02-24 | Du Pont | Dicyclopentadienyliron derivatives |
| GB864197A (en) * | 1959-01-07 | 1961-03-29 | Ici Ltd | An improved process for the manufacture of monopivalylferrocene derivatives |
-
1974
- 1974-11-11 US US05/522,593 patent/US3966783A/en not_active Expired - Lifetime
- 1974-11-14 DE DE19742453936 patent/DE2453936A1/de active Pending
- 1974-11-20 FR FR7438084A patent/FR2251318A1/fr not_active Withdrawn
- 1974-11-21 JP JP49133223A patent/JPS5093950A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377986A1 (fr) * | 1977-01-22 | 1978-08-18 | Bayer Ag | Engrais pour l'apport de fer aux vegetaux |
| DE2711546A1 (de) | 1977-03-17 | 1978-09-21 | Bayer Ag | Insektizide und akarizide mittel |
| EP0004894A1 (de) * | 1978-04-13 | 1979-10-31 | Bayer Ag | Düngemittel zur Versorgung von Pflanzen mit Eisen |
Also Published As
| Publication number | Publication date |
|---|---|
| US3966783A (en) | 1976-06-29 |
| JPS5093950A (enExample) | 1975-07-26 |
| FR2251318A1 (enExample) | 1975-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT395714B (de) | Verfahren zur herstellung von neuen aromatischen heterocyclischen verbindungen | |
| DE2408409A1 (de) | Aroylsubstituierte naphthalinessigsaeuren | |
| CH624936A5 (enExample) | ||
| DE2334425A1 (de) | Aethinylbenzol-verbindungen und derivate derselben | |
| DE2453977A1 (de) | Neue ferrocen verbindungen und verfahren zu deren herstellung sowie pharmazeutische zusammensetzungen | |
| DE3851584T2 (de) | Gegen Allergie wirkende Benzothiophene und neue und andere ausgewählte Benzothiophene, beide mit Wirkung zur Behandlung von akuten Atmungsangstanzeichen. | |
| DE2463219C2 (enExample) | ||
| EP0258729A2 (de) | Dihydropyridinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE3537207A1 (de) | Chalkonderivate | |
| DE2337068A1 (de) | 1-benzylindenylsaeuren | |
| DE2449205A1 (de) | Diaromatische o-(aminoalkyl)-oxime, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen | |
| US3966783A (en) | Compounds | |
| DE2004038A1 (de) | Chemische Verfahren und Produkte | |
| DE2039426C3 (de) | 1-Benzyliden-indenyl-(3)-essigsäuren, deren nicht-toxische, pharmakologisch verträgliche Salze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| CH634839A5 (de) | Pyranochromonderivate und ihre verwendung in arzneimitteln zur behandlung von allergien. | |
| DE2748466A1 (de) | 4a-aryloctahydro-1h-2-pyrindine | |
| DE2725932A1 (de) | Substituierte 2-vinylchromone und verfahren zu ihrer herstellung | |
| DE3641907A1 (de) | 4h-benzo(4,5)cyclohepta(1,2-b)thiophen derivate | |
| WO1994006748A1 (de) | Neue in 10-stellung substituierte anthron- und anthracen-derivate, verfahren zu deren herstellung, diese verbindungen enthaltende pharmazeutische oder kosmetische mittel und deren verwendung | |
| DE2721021A1 (de) | Neue pharmazeutisch verwendbare verbindungen | |
| DE2819215A1 (de) | Neue pyranochinolinonderivate, ihre herstellung und verwendung | |
| EP0039814B1 (de) | Imidazolyl-indeno-thiophene, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE1927786A1 (de) | Neue organische Verbindungen und Verfahren zu ihrer Herstellung | |
| DE2321151A1 (de) | Inden-acetaldehyde | |
| DE2021747A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |