FI57933C - Foerfarande foer framstaellning av terapeutiskt aktiva olefina arylketoner - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva olefina arylketoner Download PDFInfo
- Publication number
- FI57933C FI57933C FI3573/72A FI357372A FI57933C FI 57933 C FI57933 C FI 57933C FI 3573/72 A FI3573/72 A FI 3573/72A FI 357372 A FI357372 A FI 357372A FI 57933 C FI57933 C FI 57933C
- Authority
- FI
- Finland
- Prior art keywords
- fluorophenyl
- hydroxypiperidine
- hydroxy
- halogen
- butynyl
- Prior art date
Links
- 230000004913 activation Effects 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 aryl ketones Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000000571 coke Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HXSQVGRXEPJLBA-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-4-hydroxybut-2-ynyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CC#CC(O)C=2C=CC(F)=CC=2)CC1 HXSQVGRXEPJLBA-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
- GNXYPUDHDRQNMM-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-2-yn-1-ol Chemical compound FC1=CC=C(C=C1)C(C#CCN1CCN(CC1)C1=C(C=CC=C1)OC)O GNXYPUDHDRQNMM-UHFFFAOYSA-N 0.000 description 1
- JZJFKHHTWIWOOH-UHFFFAOYSA-N 1-(4-fluorophenyl)prop-2-yn-1-ol Chemical compound C#CC(O)C1=CC=C(F)C=C1 JZJFKHHTWIWOOH-UHFFFAOYSA-N 0.000 description 1
- BAXJVOZRANIQNU-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-4-hydroxybut-2-ynyl]-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C=1C=C(F)C=CC=1C(O)C#CCN(CC1)CCC1(O)C1=CC=CC(C(F)(F)F)=C1 BAXJVOZRANIQNU-UHFFFAOYSA-N 0.000 description 1
- GOBQTRRVFRKTPO-UHFFFAOYSA-N 3-[1-[4-(4-fluorophenyl)-4-hydroxybut-2-ynyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1CC#CC(O)C1=CC=C(F)C=C1 GOBQTRRVFRKTPO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ICTZOWVELHATOU-UHFFFAOYSA-N 3-piperidin-1-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1N1CCCCC1 ICTZOWVELHATOU-UHFFFAOYSA-N 0.000 description 1
- GGKPLTGBLQSSAI-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(4-chlorophenyl)-4-hydroxybut-2-ynyl]piperidin-4-ol Chemical compound ClC1=CC=C(C=C1)C(C#CCN1CCC(CC1)(O)C1=CC=C(C=C1)Cl)O GGKPLTGBLQSSAI-UHFFFAOYSA-N 0.000 description 1
- DYGGZVARYGBQSK-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-hydroxybut-2-ynyl]piperidin-4-ol Chemical compound C=1C=C(F)C=CC=1C(O)C#CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 DYGGZVARYGBQSK-UHFFFAOYSA-N 0.000 description 1
- LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 description 1
- GSLAZICDVWAGFS-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)phenyl]-1-[4-(4-fluorophenyl)-4-hydroxybut-2-ynyl]piperidin-4-ol Chemical compound C=1C=C(F)C=CC=1C(O)C#CCN(CC1)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GSLAZICDVWAGFS-UHFFFAOYSA-N 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
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- USWDTSUBSWVNJL-UHFFFAOYSA-N CCC1=C(C=CC(=C1Cl)C)C2(CCN(CC2)CC#CC(C3=CC=C(C=C3)F)O)O Chemical compound CCC1=C(C=CC(=C1Cl)C)C2(CCN(CC2)CC#CC(C3=CC=C(C=C3)F)O)O USWDTSUBSWVNJL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003354 anti-apomorphinic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 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
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10285471 | 1971-12-18 | ||
| JP10285571 | 1971-12-18 | ||
| JP46102854A JPS5820956B2 (ja) | 1971-12-18 | 1971-12-18 | シンキナル アセチレンケトンユウドウタイ ノ シンキセイゾウホウ |
| JP46102855A JPS5812273B2 (ja) | 1971-12-18 | 1971-12-18 | シンキ アセチレンアルコ−ルユウドウタイ ノ シンキセイゾウホウ |
| JP1616972 | 1972-02-15 | ||
| JP1616972A JPS5544749B2 (enrdf_load_stackoverflow) | 1971-12-18 | 1972-02-15 | |
| JP1675272A JPS5535390B2 (enrdf_load_stackoverflow) | 1971-12-18 | 1972-02-17 | |
| JP1675272 | 1972-02-17 | ||
| JP47043125A JPS491530A (enrdf_load_stackoverflow) | 1971-12-18 | 1972-04-28 | |
| JP4312572 | 1972-04-28 | ||
| JP47065208A JPS4924932A (enrdf_load_stackoverflow) | 1971-12-18 | 1972-06-28 | |
| JP6520872 | 1972-06-28 | ||
| JP47070266A JPS5839826B2 (ja) | 1971-12-18 | 1972-07-12 | シンキナルオレフイニツクアミノケトンユウドウタイ ノ シンキセイゾウホウ |
| JP47070265A JPS5820957B2 (ja) | 1971-12-18 | 1972-07-12 | シンキ ナル ブテノ−ルアミンユウドウタイ ノ シンキセイゾウホウ |
| JP7026672 | 1972-07-12 | ||
| JP7026572 | 1972-07-12 | ||
| JP9572072 | 1972-09-22 | ||
| JP47095720A JPS4961130A (enrdf_load_stackoverflow) | 1971-12-18 | 1972-09-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57933B FI57933B (fi) | 1980-07-31 |
| FI57933C true FI57933C (fi) | 1980-11-10 |
Family
ID=27576674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3573/72A FI57933C (fi) | 1971-12-18 | 1972-12-15 | Foerfarande foer framstaellning av terapeutiskt aktiva olefina arylketoner |
Country Status (9)
| Country | Link |
|---|---|
| JP (7) | JPS5544749B2 (enrdf_load_stackoverflow) |
| AU (1) | AU470861B2 (enrdf_load_stackoverflow) |
| BE (1) | BE792906A (enrdf_load_stackoverflow) |
| CH (2) | CH593296A5 (enrdf_load_stackoverflow) |
| FI (1) | FI57933C (enrdf_load_stackoverflow) |
| FR (1) | FR2163717B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1407706A (enrdf_load_stackoverflow) |
| NL (1) | NL7217236A (enrdf_load_stackoverflow) |
| SE (1) | SE399707B (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50140451A (enrdf_load_stackoverflow) * | 1974-04-16 | 1975-11-11 | ||
| JPS5116677A (ja) * | 1974-07-29 | 1976-02-10 | Sumitomo Chemical Co | Shinkinabuchirofuenonjudotai oyobi sonosanfukaennoseiho |
| JPS5283863U (enrdf_load_stackoverflow) * | 1975-12-13 | 1977-06-22 | ||
| JPS5324020A (en) * | 1976-08-14 | 1978-03-06 | Kumiai Chem Ind Co Ltd | Composition for herbicide |
| JPS5498755A (en) * | 1978-01-13 | 1979-08-03 | Sumitomo Chem Co Ltd | Novel butenophenone derivative |
| CA1151164A (en) * | 1978-01-13 | 1983-08-02 | Atsuyuki Kojima | Conjugated ketone compounds and their production and use |
| JPS55116000U (enrdf_load_stackoverflow) * | 1979-02-10 | 1980-08-15 | ||
| US4728659A (en) * | 1984-06-27 | 1988-03-01 | Ss Pharmaceutical Co., Ltd. | Aminomethyl derivatives and preparation process thereof as well as platelet aggregation inhibitors containing same |
| US5703088A (en) * | 1989-08-21 | 1997-12-30 | Beth Israel Deaconess Medical Center, Inc. | Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses |
| US5244902A (en) * | 1989-08-21 | 1993-09-14 | Beth Israel Hospital Association | Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses |
| CA2077907C (en) * | 1990-03-16 | 1998-06-09 | Richard J. Sharpe | Use of spiperone as an immunosuppressant and anti-inflammatory agent |
| US5693645A (en) * | 1992-12-23 | 1997-12-02 | Beth Israel Deaconess Medical Center, Inc. | Use of spiperone or spiperone derivatives as immunosuppressant agents |
| US11707027B2 (en) | 2019-12-02 | 2023-07-25 | Fork Farms Holdings, Llc | Hydroponic grow assembly |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK131147B (da) * | 1969-10-27 | 1975-06-02 | Sumitomo Chemical Co | Fremgangsmåde til fremstilling af butyrophenonderivater eller syreadditionssalte deraf. |
| BE758380A (fr) * | 1969-11-04 | 1971-04-16 | Sumitomo Chemical Co | Procede de preparation de derives d'aryl-cetones |
-
0
- BE BE792906D patent/BE792906A/xx unknown
-
1972
- 1972-02-15 JP JP1616972A patent/JPS5544749B2/ja not_active Expired
- 1972-02-17 JP JP1675272A patent/JPS5535390B2/ja not_active Expired
- 1972-04-28 JP JP47043125A patent/JPS491530A/ja active Pending
- 1972-06-28 JP JP47065208A patent/JPS4924932A/ja active Pending
- 1972-07-12 JP JP47070265A patent/JPS5820957B2/ja not_active Expired
- 1972-07-12 JP JP47070266A patent/JPS5839826B2/ja not_active Expired
- 1972-09-22 JP JP47095720A patent/JPS4961130A/ja active Pending
- 1972-12-15 FR FR7244857A patent/FR2163717B1/fr not_active Expired
- 1972-12-15 GB GB5810472A patent/GB1407706A/en not_active Expired
- 1972-12-15 FI FI3573/72A patent/FI57933C/fi active
- 1972-12-15 SE SE7216411A patent/SE399707B/xx unknown
- 1972-12-18 CH CH578076A patent/CH593296A5/xx not_active IP Right Cessation
- 1972-12-18 CH CH1839372A patent/CH589661A5/xx not_active IP Right Cessation
- 1972-12-18 NL NL7217236A patent/NL7217236A/xx not_active Application Discontinuation
- 1972-12-18 AU AU50231/72A patent/AU470861B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4961130A (enrdf_load_stackoverflow) | 1974-06-13 |
| FI57933B (fi) | 1980-07-31 |
| CH593296A5 (enrdf_load_stackoverflow) | 1977-11-30 |
| JPS5820957B2 (ja) | 1983-04-26 |
| JPS5544749B2 (enrdf_load_stackoverflow) | 1980-11-13 |
| CH589661A5 (enrdf_load_stackoverflow) | 1977-07-15 |
| GB1407706A (en) | 1975-09-24 |
| AU5023172A (en) | 1974-06-20 |
| FR2163717B1 (enrdf_load_stackoverflow) | 1977-07-15 |
| FR2163717A1 (enrdf_load_stackoverflow) | 1973-07-27 |
| JPS4924932A (enrdf_load_stackoverflow) | 1974-03-05 |
| JPS4881854A (enrdf_load_stackoverflow) | 1973-11-01 |
| JPS5839826B2 (ja) | 1983-09-01 |
| SE399707B (sv) | 1978-02-27 |
| JPS4930335A (enrdf_load_stackoverflow) | 1974-03-18 |
| JPS5535390B2 (enrdf_load_stackoverflow) | 1980-09-12 |
| AU470861B2 (en) | 1974-06-20 |
| NL7217236A (enrdf_load_stackoverflow) | 1973-06-20 |
| JPS4930336A (enrdf_load_stackoverflow) | 1974-03-18 |
| JPS4885569A (enrdf_load_stackoverflow) | 1973-11-13 |
| BE792906A (fr) | 1973-06-18 |
| JPS491530A (enrdf_load_stackoverflow) | 1974-01-08 |
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