DE2553708C2 - Neue Benzophenonderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen - Google Patents
Neue Benzophenonderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische ZusammensetzungenInfo
- Publication number
- DE2553708C2 DE2553708C2 DE2553708A DE2553708A DE2553708C2 DE 2553708 C2 DE2553708 C2 DE 2553708C2 DE 2553708 A DE2553708 A DE 2553708A DE 2553708 A DE2553708 A DE 2553708A DE 2553708 C2 DE2553708 C2 DE 2553708C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- methyl
- preparation
- compound
- methylbenzophenone
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 150000008366 benzophenones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- -1 arabic Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- BJICOYSAVCSVPU-UHFFFAOYSA-N 2-[3-(4-chlorobenzoyl)-2-methylphenyl]acetaldehyde Chemical compound CC1=C(CC=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 BJICOYSAVCSVPU-UHFFFAOYSA-N 0.000 description 3
- IJTNTCVBWVYIFR-UHFFFAOYSA-N 2-[3-(4-chlorobenzoyl)-2-methylphenyl]acetic acid Chemical compound CC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 IJTNTCVBWVYIFR-UHFFFAOYSA-N 0.000 description 3
- FYDDFXWWSSESLF-UHFFFAOYSA-N 2-[3-(4-chlorobenzoyl)-2-methylphenyl]acetyl chloride Chemical compound CC1=C(CC(Cl)=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 FYDDFXWWSSESLF-UHFFFAOYSA-N 0.000 description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- XTEWICOOHAZOQN-UHFFFAOYSA-N (3-butyl-2-methylphenyl)-(4-fluorophenyl)methanone Chemical compound CCCCC1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1C XTEWICOOHAZOQN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 description 1
- HCQKNVOWAHKZKH-UHFFFAOYSA-N 2-[3-(4-chlorobenzoyl)-2-methylphenyl]propanal Chemical compound O=CC(C)C1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1C HCQKNVOWAHKZKH-UHFFFAOYSA-N 0.000 description 1
- LGDLXKGSWNDDJQ-UHFFFAOYSA-N 3-(4-chlorobenzoyl)-2-methylbenzoic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 LGDLXKGSWNDDJQ-UHFFFAOYSA-N 0.000 description 1
- HPEKETAQZBJZOJ-UHFFFAOYSA-N 3-(4-chlorobenzoyl)-2-methylbenzoyl chloride Chemical compound CC1=C(C(Cl)=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 HPEKETAQZBJZOJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241001237754 Algia Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101150043532 CISH gene Proteins 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 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
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- NSQDXDMFAYCVFH-UHFFFAOYSA-M hexyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCC)C1=CC=CC=C1 NSQDXDMFAYCVFH-UHFFFAOYSA-M 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- HOODBVGAOFXXCW-UHFFFAOYSA-M pentyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC)C1=CC=CC=C1 HOODBVGAOFXXCW-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 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
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- MPNQDJZRGAOBPW-UHFFFAOYSA-M triphenyl(propyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 MPNQDJZRGAOBPW-UHFFFAOYSA-M 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7438981A FR2292467A1 (fr) | 1974-11-28 | 1974-11-28 | Nouveaux derives de la benzophenone, leur procede de preparation et leur application comme medicament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2553708A1 DE2553708A1 (de) | 1976-06-10 |
| DE2553708C2 true DE2553708C2 (de) | 1984-10-25 |
Family
ID=9145337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2553708A Expired DE2553708C2 (de) | 1974-11-28 | 1975-11-28 | Neue Benzophenonderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
Country Status (20)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2278331A1 (fr) * | 1974-01-24 | 1976-02-13 | Roussel Uclaf | Nouveaux acides carboxyliques et leurs derives, leur application comme medicaments et leur procede de preparation |
| JPS5946205B2 (ja) * | 1976-01-01 | 1984-11-10 | 科研製薬株式会社 | ベンゾイル誘導体を有効成分とする消炎鎮痛剤 |
| US4145444A (en) * | 1976-01-01 | 1979-03-20 | Kaken Chemical Co., Ltd. | Anti-inflammatory agent of benzoyl derivative |
| GB1585962A (en) * | 1976-10-14 | 1981-03-11 | Lilly Industries Ltd | Benzophenone derivatives |
| YU39085B (en) * | 1976-10-18 | 1984-04-30 | Lek Tovarna Farmacevtskih | Process for preparing 1-(3-benzoylphenyl)-propin |
| FR2371195A1 (fr) | 1976-11-22 | 1978-06-16 | Roussel Uclaf | Nouveaux derives de la (3-ethynyl phenyl) phenyl methanone, leur procede de preparation et leur application comme medicament |
| DE3411326A1 (de) * | 1984-03-28 | 1985-10-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von mit fluor enthaltenden gruppen substituierten, symmetrischen benzophenonen, deren verwendung und neue, mit fluor enthaltenden gruppen substituierte, symmetrische benzophenone |
| US5990056A (en) * | 1997-06-04 | 1999-11-23 | Mobil Oil Corporation | Compositions containing an organo-substituted benzophenone |
| GB9827855D0 (en) * | 1998-12-17 | 1999-02-10 | Wright Pugson Limited | Methods and apparatus for cutting cheese |
| EP1630600A3 (en) * | 2004-07-29 | 2006-03-22 | Rohm and Haas Electronic Materials, L.L.C. | Hot melt composition and method involving forming a masking pattern |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671016A (en) * | 1951-10-23 | 1954-03-02 | Monsanto Chemicals | Herbicidal compositions |
| US2802032A (en) * | 1955-06-22 | 1957-08-06 | Monsanto Chemicals | 3, 4-dimethylbenzophenone |
| US3924002A (en) * | 1969-07-17 | 1975-12-02 | Ciba Geigy Ag | Method for combatting harmful microorganisms |
| US3898275A (en) * | 1970-11-20 | 1975-08-05 | Sandoz Ag | M-Substituted benzophenones |
| BE787938A (fr) * | 1971-08-24 | 1973-02-26 | Nippon Kayaku Kk | Regulateurs de la croissance de vegetaux |
| BE788316A (fr) * | 1971-09-03 | 1973-03-01 | Roussel Uclaf | Nouveaux derives de l'acide butyrique et procede de preparation |
-
1974
- 1974-11-28 FR FR7438981A patent/FR2292467A1/fr active Granted
-
1975
- 1975-10-20 SE SE7511741A patent/SE7511741L/xx not_active Application Discontinuation
- 1975-10-31 IL IL48394A patent/IL48394A/xx unknown
- 1975-11-04 CA CA239,012A patent/CA1045159A/fr not_active Expired
- 1975-11-06 AT AT845575A patent/AT340901B/de not_active IP Right Cessation
- 1975-11-07 US US05/629,706 patent/US4027040A/en not_active Expired - Lifetime
- 1975-11-11 ES ES442517A patent/ES442517A1/es not_active Expired
- 1975-11-20 NL NL7513565A patent/NL7513565A/xx not_active Application Discontinuation
- 1975-11-20 ZA ZA7301A patent/ZA757301B/xx unknown
- 1975-11-20 JP JP50138779A patent/JPS606932B2/ja not_active Expired
- 1975-11-26 LU LU73868A patent/LU73868A1/xx unknown
- 1975-11-26 DD DD189699A patent/DD122070A5/xx unknown
- 1975-11-26 BE BE162199A patent/BE835971A/xx not_active IP Right Cessation
- 1975-11-27 CH CH1537575A patent/CH611259A5/xx not_active IP Right Cessation
- 1975-11-27 HU HURO870A patent/HU170501B/hu unknown
- 1975-11-27 SU SU752193205A patent/SU733515A3/ru active
- 1975-11-27 GB GB4875475A patent/GB1466657A/en not_active Expired
- 1975-11-28 DE DE2553708A patent/DE2553708C2/de not_active Expired
- 1975-11-28 IE IE2600/75A patent/IE42361B1/en unknown
- 1975-11-28 DK DK538175A patent/DK538175A/da not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA845575A (de) | 1977-05-15 |
| CH611259A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-31 |
| US4027040A (en) | 1977-05-31 |
| FR2292467B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-28 |
| DK538175A (da) | 1976-05-29 |
| IL48394A0 (en) | 1975-12-31 |
| CA1045159A (fr) | 1978-12-26 |
| NL7513565A (nl) | 1976-06-01 |
| BE835971A (fr) | 1976-05-26 |
| FR2292467A1 (fr) | 1976-06-25 |
| LU73868A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-06 |
| IE42361B1 (en) | 1980-07-30 |
| IL48394A (en) | 1978-09-29 |
| HU170501B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-28 |
| ES442517A1 (es) | 1977-04-16 |
| JPS606932B2 (ja) | 1985-02-21 |
| IE42361L (en) | 1976-05-28 |
| SE7511741L (sv) | 1976-05-31 |
| GB1466657A (en) | 1977-03-09 |
| JPS5175051A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-06-29 |
| DD122070A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-12 |
| AT340901B (de) | 1978-01-10 |
| AU8685075A (en) | 1977-05-26 |
| SU733515A3 (ru) | 1980-05-05 |
| DE2553708A1 (de) | 1976-06-10 |
| ZA757301B (en) | 1977-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2553708C2 (de) | Neue Benzophenonderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2902699B2 (de) | 15-Deoxy-16-hydroxy-prostaglandlne und Verfahren zu deren Herstellung | |
| DE2437607A1 (de) | Polyenverbindungen | |
| EP0263492A1 (de) | Neue Retinoide, deren Herstellung und Verwendung als Pharmazeutika | |
| DE3317107A1 (de) | Immunomodulierendes mittel | |
| DE2205732A1 (de) | Neue 4-(4-biphenylyl)-butensaeurederivate | |
| WO1988002746A1 (en) | Medicaments containing alpha-halogenated dicarboxylic acids | |
| DE2202727A1 (de) | Substituierte Indenylessigsaeuren | |
| AT390054B (de) | Verfahren zur herstellung von neuen benzoylderivaten von aliphatischen carbonsaeuren | |
| DE2304284C2 (de) | 1,1-Diphenyläthylen-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2542366A1 (de) | Kosmetisches haar- bzw. kopfhautpflegemittel | |
| DE2831761A1 (de) | 2,3,6-substituierte-4-pyronderivate und ihre verwendung | |
| DE2346706A1 (de) | Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung | |
| DE2318001B2 (de) | Dienische Sulfone | |
| DE2323193A1 (de) | Pyrazolidinone | |
| DE2542611A1 (de) | Benzofuranderivate | |
| DE2843811A1 (de) | Retinsaeure- und 7,8-dehydro-retinsaeure-n-(carboxy)-phenylamide | |
| DE2428200A1 (de) | Essigsaeurederivate, verfahren zu deren herstellung und diese derivate enthaltende arzneimittel | |
| DE2039426B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE1949987B2 (de) | Neue alpha-phenylfettsaeureverbindungen | |
| DE2303822C2 (de) | 1-Cyclopropyl-1-phenyl-&omega;-amino-1-alkanol-Derivate und deren Ester, Verfahren zu ihrer Herstellung und pharmazeutische Präparate auf deren Basis | |
| DE2438884A1 (de) | Neue derivate des 5-hydroxymethylthiazols, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen | |
| DE2364706C2 (de) | Prostansäurederivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| DE2603172A1 (de) | Prostaglandinantagonisten, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE3214081C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C 49/813 |
|
| 8181 | Inventor (new situation) |
Free format text: DERAEDT, ROGER, PAVILLONS-SOUS-BOIS, FR MARCHANDEAU, CHRISTIAN, ANNET-SUR-MARNE, FR MEIER, JEAN, DR., LA VARENNE SAINT-HILAIRE, FR |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |