CH635812A5 - Cycloalcanones et cycloalcanols substitues en position 3 par un groupe 2-hydroxyphenyle substitue en position 4 et composition pharmaceutique les contenant. - Google Patents
Cycloalcanones et cycloalcanols substitues en position 3 par un groupe 2-hydroxyphenyle substitue en position 4 et composition pharmaceutique les contenant. Download PDFInfo
- Publication number
- CH635812A5 CH635812A5 CH955678A CH955678A CH635812A5 CH 635812 A5 CH635812 A5 CH 635812A5 CH 955678 A CH955678 A CH 955678A CH 955678 A CH955678 A CH 955678A CH 635812 A5 CH635812 A5 CH 635812A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- phenyl
- hydrogen atom
- benzyloxy
- compound
- Prior art date
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- -1 2-HYDROXYPHENYL Chemical group 0.000 title claims description 140
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 163
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000004043 oxo group Chemical group O=* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 230000000202 analgesic effect Effects 0.000 claims 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 claims description 6
- 239000000932 sedative agent Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 230000002936 tranquilizing effect Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 230000001773 anti-convulsant effect Effects 0.000 claims description 3
- 239000002249 anxiolytic agent Substances 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000001624 sedative effect Effects 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000000949 anxiolytic effect Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- ZWWRREXSUJTKNN-UHFFFAOYSA-N 2-(3-hydroxycyclohexyl)-5-(2-methyloctan-2-yl)phenol Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1CC(O)CCC1 ZWWRREXSUJTKNN-UHFFFAOYSA-N 0.000 claims 1
- INGQOZFXGZZCLO-UHFFFAOYSA-N 3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cycloheptan-1-ol Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1CC(O)CCCC1 INGQOZFXGZZCLO-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 273
- 238000001819 mass spectrum Methods 0.000 description 162
- 238000002329 infrared spectrum Methods 0.000 description 151
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
- 239000003921 oil Substances 0.000 description 86
- 235000019198 oils Nutrition 0.000 description 86
- 239000000203 mixture Substances 0.000 description 80
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 72
- 238000002844 melting Methods 0.000 description 72
- 230000008018 melting Effects 0.000 description 72
- 238000004458 analytical method Methods 0.000 description 63
- 239000000243 solution Substances 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
- 239000011541 reaction mixture Substances 0.000 description 53
- 239000000741 silica gel Substances 0.000 description 45
- 229910002027 silica gel Inorganic materials 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 41
- 238000001953 recrystallisation Methods 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 235000019341 magnesium sulphate Nutrition 0.000 description 36
- 238000012360 testing method Methods 0.000 description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 26
- 238000000605 extraction Methods 0.000 description 25
- 125000006239 protecting group Chemical group 0.000 description 25
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 22
- 238000011282 treatment Methods 0.000 description 22
- 238000004440 column chromatography Methods 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 241000699670 Mus sp. Species 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000012442 inert solvent Substances 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 239000013543 active substance Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 229910052763 palladium Inorganic materials 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000012279 sodium borohydride Substances 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- 239000005909 Kieselgur Substances 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- GVFZTTDMOBMNCH-UHFFFAOYSA-N 1-bromo-4-(2-methyloctan-2-yl)-2-phenylmethoxybenzene Chemical compound CCCCCCC(C)(C)C1=CC=C(Br)C(OCC=2C=CC=CC=2)=C1 GVFZTTDMOBMNCH-UHFFFAOYSA-N 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000730 antalgic agent Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- HTSABYAWKQAHBT-RNFRBKRXSA-N (1r,3r)-3-methylcyclohexan-1-ol Chemical compound C[C@@H]1CCC[C@@H](O)C1 HTSABYAWKQAHBT-RNFRBKRXSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 230000003040 nociceptive effect Effects 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- HJIQNULRLPDBIJ-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)cyclohexan-1-one Chemical compound OC1=CC(O)=CC=C1C1CC(=O)CCC1 HJIQNULRLPDBIJ-UHFFFAOYSA-N 0.000 description 4
- HXMACSGVHWDXAS-UHFFFAOYSA-N 3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohex-2-en-1-one Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1=CC(=O)CCC1 HXMACSGVHWDXAS-UHFFFAOYSA-N 0.000 description 4
- OXIROJJENLMQSQ-UHFFFAOYSA-N 3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1C1CC(=O)CCC1 OXIROJJENLMQSQ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000003747 Grignard reaction Methods 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000764238 Isis Species 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000007239 Wittig reaction Methods 0.000 description 4
- LQCYIQBYFCQMCH-UHFFFAOYSA-N [Li].C[Cu]C Chemical compound [Li].C[Cu]C LQCYIQBYFCQMCH-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 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
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- KJKTVIZLIDCMEC-VAVYLYDRSA-N (3r,4s)-3-[4-(2-methyloctan-2-yl)-2-phenylmethoxyphenyl]-4-prop-2-enylcyclohexan-1-one Chemical compound C=1C=CC=CC=1COC1=CC(C(C)(C)CCCCCC)=CC=C1[C@@H]1CC(=O)CC[C@H]1CC=C KJKTVIZLIDCMEC-VAVYLYDRSA-N 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- LOZPYEHYCGBIRZ-UHFFFAOYSA-N 3-[4-(2-methyldecan-2-yl)-2-phenylmethoxyphenyl]cyclohexan-1-one Chemical compound C=1C=CC=CC=1COC1=CC(C(C)(C)CCCCCCCC)=CC=C1C1CCCC(=O)C1 LOZPYEHYCGBIRZ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
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- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
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- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
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- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
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- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
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- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
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- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/95—Esters of quinone carboxylic acids
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- C—CHEMISTRY; METALLURGY
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (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)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83310277A | 1977-09-13 | 1977-09-13 | |
US92668778A | 1978-07-25 | 1978-07-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH635812A5 true CH635812A5 (fr) | 1983-04-29 |
Family
ID=27125579
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH955678A CH635812A5 (fr) | 1977-09-13 | 1978-09-13 | Cycloalcanones et cycloalcanols substitues en position 3 par un groupe 2-hydroxyphenyle substitue en position 4 et composition pharmaceutique les contenant. |
Country Status (27)
Country | Link |
---|---|
JP (1) | JPS5448741A (no) |
AR (1) | AR224618A1 (no) |
AT (1) | AT361455B (no) |
AU (1) | AU513523B2 (no) |
CA (1) | CA1110261A (no) |
CH (1) | CH635812A5 (no) |
DE (1) | DE2839836C2 (no) |
DK (1) | DK400878A (no) |
ES (3) | ES473288A1 (no) |
FI (1) | FI66584C (no) |
FR (1) | FR2402639A1 (no) |
GB (1) | GB2004870B (no) |
GR (1) | GR74134B (no) |
HK (1) | HK13284A (no) |
IE (1) | IE47187B1 (no) |
IL (1) | IL55556A (no) |
IN (1) | IN150334B (no) |
IT (1) | IT1099054B (no) |
KE (1) | KE3352A (no) |
LU (1) | LU80220A1 (no) |
MX (1) | MX5306E (no) |
MY (1) | MY8500094A (no) |
NL (2) | NL7809274A (no) |
NO (2) | NO149426C (no) |
NZ (1) | NZ188391A (no) |
PH (2) | PH15252A (no) |
SE (1) | SE431085B (no) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IN162851B (no) * | 1980-09-19 | 1988-07-16 | Pfizer | |
US4285867A (en) * | 1980-09-19 | 1981-08-25 | Pfizer Inc. | Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor |
US5650270A (en) * | 1982-02-01 | 1997-07-22 | Northeastern University | Molecular analytical release tags and their use in chemical analysis |
US4709016A (en) * | 1982-02-01 | 1987-11-24 | Northeastern University | Molecular analytical release tags and their use in chemical analysis |
JPS58201737A (ja) * | 1982-05-18 | 1983-11-24 | Mitsui Toatsu Chem Inc | 新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
GB8330099D0 (en) * | 1983-11-11 | 1983-12-21 | Ici Plc | Cycloalkane derivatives |
IL75480A0 (en) * | 1985-06-11 | 1985-10-31 | Yissum Res Dev Co | Alkoxyphenol derivatives and pharmaceutical compositions containing them |
US4623657A (en) * | 1985-09-05 | 1986-11-18 | Hoechst-Roussel Pharmaceuticals Inc. | Spiro [benzofuran-2(3H),1'-cycloheptane]s and their therapeutic use |
IE70521B1 (en) * | 1989-02-28 | 1996-12-11 | Zeneca Pharma Sa | Heterocycles with inhibitory activity of 5-lipoxygenase |
US6828460B2 (en) | 1999-03-22 | 2004-12-07 | Pfizer Inc. | Resorcinol derivatives |
ES2238993T3 (es) * | 1999-03-22 | 2005-09-16 | Pfizer Inc. | Derivados de resorcinol. |
US7612101B2 (en) | 2006-04-24 | 2009-11-03 | Allergan, Inc. | Abnormal cannabidiols as agents for lowering intraocular pressure |
US7718830B2 (en) | 2006-04-24 | 2010-05-18 | Allergan, Inc. | Abnormal cannabidiols as agents for lowering intraocular pressure |
US7618966B2 (en) | 2006-04-24 | 2009-11-17 | Allergan, Inc. | Abnormal Cannabidiols as agents for lowering intraocular pressure |
WO2007127711A2 (en) * | 2006-04-24 | 2007-11-08 | Allergan, Inc. | Abnormal cannabidiols as agents for lowering intraocular pressure |
CN109369514B (zh) * | 2018-12-10 | 2021-10-26 | 天津科技大学 | 一种六元碳环衍生物的合成方法 |
EP3997098A4 (en) * | 2019-07-12 | 2023-10-11 | Canopy Growth Corporation | CANNABINOIDS DERIVATIVES |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU487907A1 (ru) * | 1973-09-21 | 1975-10-15 | Полоцкий Химический Комбинат Им. 50-Летия Белор.Сср | Полимерна композици |
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1978
- 1978-08-28 SE SE7809060A patent/SE431085B/sv unknown
- 1978-09-01 IN IN649/DEL/78A patent/IN150334B/en unknown
- 1978-09-06 CA CA310,713A patent/CA1110261A/en not_active Expired
- 1978-09-11 GR GR57203A patent/GR74134B/el unknown
- 1978-09-12 AT AT658778A patent/AT361455B/de not_active IP Right Cessation
- 1978-09-12 ES ES473288A patent/ES473288A1/es not_active Expired
- 1978-09-12 FI FI782794A patent/FI66584C/fi not_active IP Right Cessation
- 1978-09-12 GB GB7836418A patent/GB2004870B/en not_active Expired
- 1978-09-12 JP JP11217078A patent/JPS5448741A/ja active Granted
- 1978-09-12 IL IL55556A patent/IL55556A/xx unknown
- 1978-09-12 NL NL7809274A patent/NL7809274A/xx not_active Application Discontinuation
- 1978-09-12 LU LU80220A patent/LU80220A1/fr unknown
- 1978-09-12 NZ NZ188391A patent/NZ188391A/en unknown
- 1978-09-12 NO NO783087A patent/NO149426C/no unknown
- 1978-09-12 DK DK400878A patent/DK400878A/da not_active Application Discontinuation
- 1978-09-12 FR FR7826194A patent/FR2402639A1/fr not_active Withdrawn
- 1978-09-12 IE IE1841/78A patent/IE47187B1/en unknown
- 1978-09-12 IT IT27558/78A patent/IT1099054B/it active
- 1978-09-13 AR AR273693A patent/AR224618A1/es active
- 1978-09-13 CH CH955678A patent/CH635812A5/fr not_active IP Right Cessation
- 1978-09-13 AU AU39818/78A patent/AU513523B2/en not_active Expired
- 1978-09-13 DE DE2839836A patent/DE2839836C2/de not_active Expired
- 1978-09-13 MX MX787390U patent/MX5306E/es unknown
- 1978-09-13 PH PH21596A patent/PH15252A/en unknown
-
1979
- 1979-05-02 ES ES480150A patent/ES480150A1/es not_active Expired
- 1979-05-02 ES ES480149A patent/ES8100795A1/es not_active Expired
- 1979-09-03 NO NO792840A patent/NO792840L/no unknown
- 1979-10-09 PH PH23144A patent/PH16597A/en unknown
-
1983
- 1983-09-30 NL NL8303358A patent/NL8303358A/nl not_active Application Discontinuation
- 1983-11-22 KE KE3352A patent/KE3352A/xx unknown
-
1984
- 1984-02-16 HK HK132/84A patent/HK13284A/xx unknown
-
1985
- 1985-12-30 MY MY94/85A patent/MY8500094A/xx unknown
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