DES0028540MA - - Google Patents
Info
- Publication number
- DES0028540MA DES0028540MA DES0028540MA DE S0028540M A DES0028540M A DE S0028540MA DE S0028540M A DES0028540M A DE S0028540MA
- Authority
- DE
- Germany
- Prior art keywords
- ketone
- acetoxycyclohexyl
- ketocyclohexyl
- oxycyclohexyl
- phenyloxymethyl
- 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.)
- Active
Links
- -1 ketocyclohexyl Chemical group 0.000 claims description 59
- 150000002576 ketones Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 5
- GJXXDQBMNMSDNT-UHFFFAOYSA-N 1,3-diphenoxypropan-2-one Chemical compound C=1C=CC=CC=1OCC(=O)COC1=CC=CC=C1 GJXXDQBMNMSDNT-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- KQIBCUGTHWUJFR-UHFFFAOYSA-N (2-cyclohexylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C1CCCCC1 KQIBCUGTHWUJFR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 241001465754 Metazoa Species 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UHSRTRHXMOZQIM-UHFFFAOYSA-N [2-oxo-3-(2-phenylacetyl)oxypropyl] 2-phenylacetate Chemical compound C=1C=CC=CC=1CC(=O)OCC(=O)COC(=O)CC1=CC=CC=C1 UHSRTRHXMOZQIM-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 5
- 241000219198 Brassica Species 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003470 adrenal cortex hormone Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AKVJDXBLRZFJFZ-UHFFFAOYSA-N 1,3-dibromo-1,3-diphenylpropan-2-one Chemical class C=1C=CC=CC=1C(Br)C(=O)C(Br)C1=CC=CC=C1 AKVJDXBLRZFJFZ-UHFFFAOYSA-N 0.000 description 2
- LQQKDSXCDXHLLF-UHFFFAOYSA-N 1,3-dibromopropan-2-one Chemical class BrCC(=O)CBr LQQKDSXCDXHLLF-UHFFFAOYSA-N 0.000 description 2
- DRKBRDLMRBVZKV-UHFFFAOYSA-N 1,3-dichloro-1,3-diphenylpropan-2-one Chemical class C=1C=CC=CC=1C(Cl)C(=O)C(Cl)C1=CC=CC=C1 DRKBRDLMRBVZKV-UHFFFAOYSA-N 0.000 description 2
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical class ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
- MSDQNIRGPBARGC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanone Chemical class C1=CC(C(=O)C)=CC=C1C1CCCCC1 MSDQNIRGPBARGC-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OCJKSUSNMXDOGL-UHFFFAOYSA-N (2-phenylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C1=CC=CC=C1 OCJKSUSNMXDOGL-UHFFFAOYSA-N 0.000 description 1
- BPTLOURWNCPYTR-UHFFFAOYSA-N (4-phenylcyclohexyl) acetate Chemical compound C1CC(OC(=O)C)CCC1C1=CC=CC=C1 BPTLOURWNCPYTR-UHFFFAOYSA-N 0.000 description 1
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- XAUODTQFYKRDJT-UHFFFAOYSA-N 1,3-diiodo-1,3-diphenylpropan-2-one Chemical class C=1C=CC=CC=1C(I)C(=O)C(I)C1=CC=CC=C1 XAUODTQFYKRDJT-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- 244000178993 Brassica juncea Species 0.000 description 1
- TVWVYABGMFWAKM-UHFFFAOYSA-N C(C)(=O)OC1CCC(CC1)C1=CC=C(C=C1)C(Cl)C(=O)C(C1=CC=C(C=C1)C1CCC(CC1)OC(C)=O)Cl Chemical compound C(C)(=O)OC1CCC(CC1)C1=CC=C(C=C1)C(Cl)C(=O)C(C1=CC=C(C=C1)C1CCC(CC1)OC(C)=O)Cl TVWVYABGMFWAKM-UHFFFAOYSA-N 0.000 description 1
- MROZMRCKKCNECB-UHFFFAOYSA-N CC(=O)C.[I] Chemical class CC(=O)C.[I] MROZMRCKKCNECB-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 210000004404 adrenal cortex Anatomy 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 229940119740 deoxycorticosterone Drugs 0.000 description 1
- OKBPCTLSPGDQBO-UHFFFAOYSA-L disodium;dichloride Chemical compound [Na+].[Na+].[Cl-].[Cl-] OKBPCTLSPGDQBO-UHFFFAOYSA-L 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2228423B2 (de) | 3,4-Dihydro-t,23-oxathiazin-4-one und Verfahren zu ihrer Herstellung | |
| DE2755759A1 (de) | 4-(4-acyl-3-hydroxy-8-methyltridecyl)- benzoesaeuren | |
| DE1468201C2 (de) | (alpha Alkylidenacyl) phenoxy essig saure Verbindungen und Verfahren zu ihrer Herstellung | |
| DE3133583A1 (de) | Verfahren zur herstellung von hydroxyphenyl-aliphatischen saeurederivaten und katalysator dafuer | |
| DE1493912A1 (de) | Naphthylessigsaeuren und Verfahren zu deren Herstellung | |
| DE2108649C3 (de) | 2-Methyl-2-hepten-6-on-l-al und seine Acetale | |
| DE2530466C3 (de) | Xanthonverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen mit einem Gehalt dieser Verbindungen | |
| DE946445C (de) | Verfahren zur Herstellung von p-Cyclohexylphenylmethylketonen | |
| DES0028540MA (enrdf_load_stackoverflow) | ||
| DE946446C (de) | Verfahren zur Herstellung von p-Cyclohexylphenylmethylketonen | |
| DE2241680A1 (de) | 17-hydroxy-7-(niedr.alkoxy)carbonyl3-oxo-17alpha-pregn-4-en-21-carbonsaeuregamma-lactone, die ihnen zugrunde liegenden saeuren und ihre salze | |
| DE2560602C2 (de) | Sauerstoffhaltige Diarylamidine | |
| DE527714C (de) | Verfahren zur Darstellung von loeslichen Verbindungen der Oxydiphenylaether bzw. Oxydiphenylsulfide und deren Derivaten | |
| DES0041461MA (enrdf_load_stackoverflow) | ||
| DE2219455A1 (de) | Substituierte Acetaldehyde und Verfahren zu ihrer Herstellung | |
| CH513806A (de) | Verfahren zur Herstellung von tricyclischen Verbindungen | |
| DE2605650A1 (de) | Verfahren zur herstellung von para-isobutyl-phenylessigsaeurederivaten | |
| DE958844C (de) | Verfahren zur Herstellung von ª†-Acyl-buttersaeuren | |
| DE903212C (de) | Verfahren zur Herstellung von substituierten Cyclohexenonverbindungen zur Schaedlingsbekaempfung | |
| DE806458C (de) | Verfahren zur Herstellung von Cumarinen | |
| DE2626388A1 (de) | Alkoxy-substituierte thiophencarbonsaeure-verbindungen und verfahren zu ihrer herstellung | |
| DE939506C (de) | Verfahren zur Herstellung von stickstoffsubstituierten Derivaten des ªÏ-Phenyl-tert.-butylamins | |
| DE2335067A1 (de) | Substituierte geranylessigsaeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE1468517C (de) | Steroide der Ostranreihe und Ver fahren zu deren Herstellung | |
| DE890791C (de) | Verfahren zur Herstellung von Dioxyacetonverbmdungen |