DE2449928A1 - Verfahren zur herstellung neuer carbocyclischer verbindungen - Google Patents
Verfahren zur herstellung neuer carbocyclischer verbindungenInfo
- Publication number
- DE2449928A1 DE2449928A1 DE19742449928 DE2449928A DE2449928A1 DE 2449928 A1 DE2449928 A1 DE 2449928A1 DE 19742449928 DE19742449928 DE 19742449928 DE 2449928 A DE2449928 A DE 2449928A DE 2449928 A1 DE2449928 A1 DE 2449928A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acid
- hydrogen
- lower alkyl
- compounds
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000001717 carbocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 93
- 239000002253 acid Substances 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 17
- 150000007513 acids Chemical class 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 100
- 239000000243 solution Substances 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- -1 for example Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 10
- 239000012259 ether extract Substances 0.000 description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CRVLWWKYIRLIAX-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1h-inden-5-yl)acetonitrile Chemical compound C1=C(CC#N)C=C2CC(CC)CC2=C1 CRVLWWKYIRLIAX-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- AVLCYTRBQULWGZ-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yl)acetic acid Chemical class OC(=O)CC1=CC=C2CCCC2=C1 AVLCYTRBQULWGZ-UHFFFAOYSA-N 0.000 description 2
- FZSXXUAESILITC-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yl)acetonitrile Chemical class N#CCC1=CC=C2CCCC2=C1 FZSXXUAESILITC-UHFFFAOYSA-N 0.000 description 2
- WJNBFERHVLTYOV-UHFFFAOYSA-N 2-ethyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2CC(CC)CC2=C1 WJNBFERHVLTYOV-UHFFFAOYSA-N 0.000 description 2
- SCSAVKHBLSDFHA-UHFFFAOYSA-N 2-ethyl-6-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(C)C=C2C(=O)C(CC)CC2=C1 SCSAVKHBLSDFHA-UHFFFAOYSA-N 0.000 description 2
- BEKNOGMQVKBMQN-UHFFFAOYSA-N 2-methyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(C)CC2=C1 BEKNOGMQVKBMQN-UHFFFAOYSA-N 0.000 description 2
- HOWRLXGUHZATCY-UHFFFAOYSA-N 2-propan-2-yl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2CC(C(C)C)CC2=C1 HOWRLXGUHZATCY-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- RMOPJLIMRSAIMD-UHFFFAOYSA-N methyl 2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OC)CC2=C1 RMOPJLIMRSAIMD-UHFFFAOYSA-N 0.000 description 2
- HQRRALFQIFEXHE-UHFFFAOYSA-N methyl 2-(2-ethyl-2-methyl-1,3-dihydroinden-5-yl)-2-oxoacetate Chemical compound C1=C(C(=O)C(=O)OC)C=C2CC(CC)(C)CC2=C1 HQRRALFQIFEXHE-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-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
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- FEOMBAAEXKNUPQ-UHFFFAOYSA-N 2,2,5-trimethyl-1,3-dihydroindene Chemical compound CC1=CC=C2CC(C)(C)CC2=C1 FEOMBAAEXKNUPQ-UHFFFAOYSA-N 0.000 description 1
- STDPPKPGKZRLBR-UHFFFAOYSA-N 2,2,6-trimethyl-3h-inden-1-one Chemical compound CC1=CC=C2CC(C)(C)C(=O)C2=C1 STDPPKPGKZRLBR-UHFFFAOYSA-N 0.000 description 1
- YGJGLASPUHXBJJ-UHFFFAOYSA-N 2,2-diethyl-1,3-dihydroindene Chemical compound C1=CC=C2CC(CC)(CC)CC2=C1 YGJGLASPUHXBJJ-UHFFFAOYSA-N 0.000 description 1
- NKGZQQSGOMGCJP-UHFFFAOYSA-N 2,2-diethyl-3h-inden-1-one Chemical compound C1=CC=C2C(=O)C(CC)(CC)CC2=C1 NKGZQQSGOMGCJP-UHFFFAOYSA-N 0.000 description 1
- VAMWEVQXIHGFHY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dihydroindene Chemical compound C1=CC=C2CC(C)(C)CC2=C1 VAMWEVQXIHGFHY-UHFFFAOYSA-N 0.000 description 1
- XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 description 1
- STNFIASCZZDOMJ-UHFFFAOYSA-N 2-(1-methyl-2,3-dihydro-1H-inden-5-yl)acetic acid Chemical compound CC1CCC2=CC(=CC=C12)CC(=O)O STNFIASCZZDOMJ-UHFFFAOYSA-N 0.000 description 1
- IUFKLFPCCHIDPO-UHFFFAOYSA-N 2-(2-ethyl-2,6-dimethyl-1,3-dihydroinden-5-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C=C2CC(CC)(C)CC2=C1 IUFKLFPCCHIDPO-UHFFFAOYSA-N 0.000 description 1
- LKLMTWABCIFGBB-UHFFFAOYSA-N 2-(4,7-dichloro-2-ethyl-2,3-dihydro-1h-inden-5-yl)acetic acid Chemical compound ClC1=C(CC(O)=O)C=C(Cl)C2=C1CC(CC)C2 LKLMTWABCIFGBB-UHFFFAOYSA-N 0.000 description 1
- LJWXBSNLVNLGIL-UHFFFAOYSA-N 2-(6-chloro-2-ethyl-2-methyl-1,3-dihydroinden-5-yl)acetic acid Chemical compound ClC1=C(CC(O)=O)C=C2CC(CC)(C)CC2=C1 LJWXBSNLVNLGIL-UHFFFAOYSA-N 0.000 description 1
- MXJOOOORBCLBJW-UHFFFAOYSA-N 2-(7-chloro-2-ethyl-4-methyl-2,3-dihydro-1h-inden-5-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C=C(Cl)C2=C1CC(CC)C2 MXJOOOORBCLBJW-UHFFFAOYSA-N 0.000 description 1
- NJBBYJQMQSQQSS-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylidene]butanoic acid Chemical compound CCC(C(O)=O)=CC1=CC=C(Cl)C=C1 NJBBYJQMQSQQSS-UHFFFAOYSA-N 0.000 description 1
- ZORCKUHKWCGHCK-UHFFFAOYSA-N 2-[(4-methylphenyl)methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=C(C)C=C1 ZORCKUHKWCGHCK-UHFFFAOYSA-N 0.000 description 1
- BDQWJOXTVXTACJ-UHFFFAOYSA-N 2-benzyl-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)CC1=CC=CC=C1 BDQWJOXTVXTACJ-UHFFFAOYSA-N 0.000 description 1
- RTGUTAJFTGYOFV-UHFFFAOYSA-N 2-ethyl-2,5-dimethyl-1,3-dihydroindene Chemical compound C1=C(C)C=C2CC(CC)(C)CC2=C1 RTGUTAJFTGYOFV-UHFFFAOYSA-N 0.000 description 1
- LOGOBHZWZUMITB-UHFFFAOYSA-N 2-ethyl-2,6-dimethyl-3h-inden-1-one Chemical compound C1=C(C)C=C2C(=O)C(CC)(C)CC2=C1 LOGOBHZWZUMITB-UHFFFAOYSA-N 0.000 description 1
- AEEVXLYZMMRYGH-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-dihydroindene Chemical compound C1=CC=C2CC(CC)(C)CC2=C1 AEEVXLYZMMRYGH-UHFFFAOYSA-N 0.000 description 1
- RQCBOHYRIIMTQB-UHFFFAOYSA-N 2-ethyl-2-methyl-3h-inden-1-one Chemical compound C1=CC=C2C(=O)C(CC)(C)CC2=C1 RQCBOHYRIIMTQB-UHFFFAOYSA-N 0.000 description 1
- TUICGGIVQMFOTI-UHFFFAOYSA-N 2-ethyl-5-methyl-2,3-dihydro-1h-indene Chemical compound C1=C(C)C=C2CC(CC)CC2=C1 TUICGGIVQMFOTI-UHFFFAOYSA-N 0.000 description 1
- LJMSAUILRDVXCA-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.COC(=O)C(O)=O LJMSAUILRDVXCA-UHFFFAOYSA-N 0.000 description 1
- MWGYLUXMIMSOTM-UHFFFAOYSA-N 2-methyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2CC(C)CC2=C1 MWGYLUXMIMSOTM-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WVZKEIVGAZKERI-UHFFFAOYSA-N 5-(chloromethyl)-2-ethyl-2,3-dihydro-1h-indene Chemical compound C1=C(CCl)C=C2CC(CC)CC2=C1 WVZKEIVGAZKERI-UHFFFAOYSA-N 0.000 description 1
- DSRDRBBKJQRSTR-UHFFFAOYSA-N 5-chloro-2,2-dimethyl-1,3-dihydroindene Chemical compound C1=C(Cl)C=C2CC(C)(C)CC2=C1 DSRDRBBKJQRSTR-UHFFFAOYSA-N 0.000 description 1
- RDGAHJVYMGGBSP-UHFFFAOYSA-N 5-chloro-2-ethyl-2,3-dihydro-1h-indene Chemical compound C1=C(Cl)C=C2CC(CC)CC2=C1 RDGAHJVYMGGBSP-UHFFFAOYSA-N 0.000 description 1
- JMJWRBGRURZMBU-UHFFFAOYSA-N 5-chloro-2-ethyl-2-methyl-1,3-dihydroindene Chemical compound C1=C(Cl)C=C2CC(CC)(C)CC2=C1 JMJWRBGRURZMBU-UHFFFAOYSA-N 0.000 description 1
- XFZYJZIKQGZVES-UHFFFAOYSA-N 6-chloro-2,2-dimethyl-3h-inden-1-one Chemical compound C1=C(Cl)C=C2C(=O)C(C)(C)CC2=C1 XFZYJZIKQGZVES-UHFFFAOYSA-N 0.000 description 1
- IRURELYZMSFEPX-UHFFFAOYSA-N 6-chloro-2-ethyl-2,3-dihydroinden-1-one Chemical compound C1=C(Cl)C=C2C(=O)C(CC)CC2=C1 IRURELYZMSFEPX-UHFFFAOYSA-N 0.000 description 1
- UVUBHIAEEMUZAS-UHFFFAOYSA-N 6-chloro-2-ethyl-2-methyl-3h-inden-1-one Chemical compound C1=C(Cl)C=C2C(=O)C(CC)(C)CC2=C1 UVUBHIAEEMUZAS-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QZUFFONNAZZTRS-UHFFFAOYSA-N CCOC(=O)CC1=CC=C2CCCC2=C1 Chemical compound CCOC(=O)CC1=CC=C2CCCC2=C1 QZUFFONNAZZTRS-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 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
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical group [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 230000002579 anti-swelling effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons 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
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003459 chloroalkylation reaction Methods 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- GYUCVQSNZFRDRL-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylbutanoate Chemical compound CCOC(=O)C(CC)P(=O)(OCC)OCC GYUCVQSNZFRDRL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- PDYABGLFTKVEGV-UHFFFAOYSA-N methyl 2-(6-chloro-2-ethyl-2-methyl-1,3-dihydroinden-5-yl)-2-oxoacetate Chemical compound ClC1=C(C(=O)C(=O)OC)C=C2CC(CC)(C)CC2=C1 PDYABGLFTKVEGV-UHFFFAOYSA-N 0.000 description 1
- IRJWMXMPICMUOO-UHFFFAOYSA-N methyl 2-(6-chloro-2-ethyl-2-methyl-1,3-dihydroinden-5-yl)acetate Chemical compound ClC1=C(CC(=O)OC)C=C2CC(CC)(C)CC2=C1 IRJWMXMPICMUOO-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1525173A CH592598A5 (en, 2012) | 1973-10-30 | 1973-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2449928A1 true DE2449928A1 (de) | 1975-05-07 |
Family
ID=4407595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742449928 Withdrawn DE2449928A1 (de) | 1973-10-30 | 1974-10-21 | Verfahren zur herstellung neuer carbocyclischer verbindungen |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4166131A (en, 2012) |
| JP (3) | JPS5756460B2 (en, 2012) |
| BE (1) | BE821557A (en, 2012) |
| CA (1) | CA1061362A (en, 2012) |
| CH (1) | CH592598A5 (en, 2012) |
| CS (2) | CS183796B2 (en, 2012) |
| DD (1) | DD114058A5 (en, 2012) |
| DE (1) | DE2449928A1 (en, 2012) |
| DK (1) | DK550774A (en, 2012) |
| ES (5) | ES431432A1 (en, 2012) |
| FI (1) | FI59984C (en, 2012) |
| FR (1) | FR2248831B1 (en, 2012) |
| GB (1) | GB1484088A (en, 2012) |
| HU (1) | HU168104B (en, 2012) |
| IE (1) | IE40194B1 (en, 2012) |
| IL (1) | IL45945A (en, 2012) |
| NL (1) | NL7413981A (en, 2012) |
| NO (1) | NO143499C (en, 2012) |
| PH (1) | PH12417A (en, 2012) |
| PL (2) | PL92094B1 (en, 2012) |
| SE (1) | SE418176B (en, 2012) |
| SU (1) | SU843732A3 (en, 2012) |
| ZA (1) | ZA746984B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50111057A (en, 2012) * | 1974-02-14 | 1975-09-01 | ||
| DK470875A (da) * | 1974-10-29 | 1976-04-30 | Sandoz Ag | Fremgangsmade til fremstilling af benzenderivater |
| FR2379511A1 (fr) * | 1977-02-02 | 1978-09-01 | Hexachimie | Sel de lysine de l'acide a-methyl (isopropyl-2 indanyl-5) acetique |
| LU77254A1 (en, 2012) * | 1977-05-04 | 1979-01-18 | ||
| US5179229A (en) * | 1992-04-24 | 1993-01-12 | Hoechst Celanese Corporation | Preparation of 2,2-diorgano-3-arylpropionic acids and esters thereof |
| JP2003083822A (ja) * | 2001-09-10 | 2003-03-19 | Nichiyo Engineering Kk | 締め付けトルク測定方法および装置 |
| US7888381B2 (en) * | 2005-06-14 | 2011-02-15 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity, and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4058622A (en) * | 1972-07-11 | 1977-11-15 | Sumitomo Chemical Company, Limited | Substituted phenyl acetate, insecticidal composition and method of use |
-
1973
- 1973-10-30 CH CH1525173A patent/CH592598A5/xx not_active IP Right Cessation
-
1974
- 1974-10-21 FI FI3073/74A patent/FI59984C/fi active
- 1974-10-21 DE DE19742449928 patent/DE2449928A1/de not_active Withdrawn
- 1974-10-21 NO NO743788A patent/NO143499C/no unknown
- 1974-10-21 DK DK550774A patent/DK550774A/da unknown
- 1974-10-23 SE SE7413366A patent/SE418176B/xx unknown
- 1974-10-24 US US05/517,531 patent/US4166131A/en not_active Expired - Lifetime
- 1974-10-24 GB GB46116/74A patent/GB1484088A/en not_active Expired
- 1974-10-25 NL NL7413981A patent/NL7413981A/xx not_active Application Discontinuation
- 1974-10-25 DD DD181934A patent/DD114058A5/xx unknown
- 1974-10-28 PL PL1974185104A patent/PL92094B1/pl unknown
- 1974-10-28 CA CA212,355A patent/CA1061362A/en not_active Expired
- 1974-10-28 ES ES431432A patent/ES431432A1/es not_active Expired
- 1974-10-28 BE BE149946A patent/BE821557A/xx unknown
- 1974-10-28 IL IL45945A patent/IL45945A/en unknown
- 1974-10-28 PH PH16458A patent/PH12417A/en unknown
- 1974-10-28 IE IE2217/74A patent/IE40194B1/xx unknown
- 1974-10-28 PL PL1974185105A patent/PL92438B1/pl unknown
- 1974-10-29 JP JP49124022A patent/JPS5756460B2/ja not_active Expired
- 1974-10-29 CS CS7500007942A patent/CS183796B2/cs unknown
- 1974-10-29 HU HUSE1668A patent/HU168104B/hu unknown
- 1974-10-29 CS CS7400007369A patent/CS183767B2/cs unknown
- 1974-10-29 FR FR7436068A patent/FR2248831B1/fr not_active Expired
- 1974-10-30 ZA ZA00746984A patent/ZA746984B/xx unknown
-
1975
- 1975-12-10 SU SU752197008A patent/SU843732A3/ru active
-
1976
- 1976-08-02 ES ES450381A patent/ES450381A1/es not_active Expired
- 1976-08-02 ES ES450379A patent/ES450379A1/es not_active Expired
- 1976-08-02 ES ES450382A patent/ES450382A1/es not_active Expired
- 1976-08-02 ES ES450380A patent/ES450380A1/es not_active Expired
-
1981
- 1981-05-08 JP JP6846881A patent/JPS56164138A/ja active Granted
- 1981-05-08 JP JP6846781A patent/JPS56164137A/ja active Granted
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