FI58636C - Foerfarande foer framstaellning av butyrofenonderivat - Google Patents
Foerfarande foer framstaellning av butyrofenonderivat Download PDFInfo
- Publication number
- FI58636C FI58636C FI82473A FI82473A FI58636C FI 58636 C FI58636 C FI 58636C FI 82473 A FI82473 A FI 82473A FI 82473 A FI82473 A FI 82473A FI 58636 C FI58636 C FI 58636C
- Authority
- FI
- Finland
- Prior art keywords
- group
- yield
- fluorobutyrophenone
- formula
- piperidin
- Prior art date
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229940054053 antipsychotics butyrophenone derivative Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 102100027373 Melanin-concentrating hormone receptor 2 Human genes 0.000 claims 1
- 101710089759 Melanin-concentrating hormone receptor 2 Proteins 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 analgesic Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000010779 crude oil Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VHRFPUMAKVIABM-UHFFFAOYSA-N 2-(benzylamino)-4-fluoro-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-1-phenylbutan-1-one Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1C(F)CC(C(=O)C=1C=CC=CC=1)NCC1=CC=CC=C1 VHRFPUMAKVIABM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LZEZXTQEZRUGDD-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,4-difluoro-1-phenylbutan-1-one;hydrochloride Chemical compound Cl.C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(F)CC(F)C(=O)C1=CC=CC=C1 LZEZXTQEZRUGDD-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000000506 psychotropic effect Effects 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VOMBUHFEHUDBJX-UHFFFAOYSA-N 1-[3-[2-(2,4-difluorophenyl)-1,3-dioxolan-2-yl]propyl]-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCC1(C=2C(=CC(F)=CC=2)F)OCCO1 VOMBUHFEHUDBJX-UHFFFAOYSA-N 0.000 description 1
- DZGASGXWWSJZFV-UHFFFAOYSA-N 1-[3-[2-(2,4-difluorophenyl)-1,3-dioxolan-2-yl]propyl]-4-phenylpiperazine Chemical compound FC1=CC(F)=CC=C1C1(CCCN2CCN(CC2)C=2C=CC=CC=2)OCCO1 DZGASGXWWSJZFV-UHFFFAOYSA-N 0.000 description 1
- QWBOXEXAVBYYFU-UHFFFAOYSA-N 2,4-difluoro-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-1-phenylbutan-1-one Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1C(F)CC(F)C(=O)C1=CC=CC=C1 QWBOXEXAVBYYFU-UHFFFAOYSA-N 0.000 description 1
- INKXUVDVFWOIBB-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(2,4-difluorophenyl)-1,3-dioxolane Chemical compound FC1=CC(F)=CC=C1C1(CCCCl)OCCO1 INKXUVDVFWOIBB-UHFFFAOYSA-N 0.000 description 1
- ATWGMBJUFXEASY-UHFFFAOYSA-N 2-(benzylamino)-4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-fluoro-1-phenylbutan-1-one Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(F)CC(C(=O)C=1C=CC=CC=1)NCC1=CC=CC=C1 ATWGMBJUFXEASY-UHFFFAOYSA-N 0.000 description 1
- KOSJOVHMKCBKIY-UHFFFAOYSA-N 2-(benzylamino)-4-fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]-1-phenylbutan-1-one Chemical compound COC1=CC=CC=C1N1CCN(C(F)CC(NCC=2C=CC=CC=2)C(=O)C=2C=CC=CC=2)CC1 KOSJOVHMKCBKIY-UHFFFAOYSA-N 0.000 description 1
- OWDQWGXSOHSNHO-UHFFFAOYSA-N 2-(dimethylamino)-4-fluoro-1-phenylbutan-1-one Chemical compound CN(C(C(=O)C1=CC=CC=C1)CCF)C OWDQWGXSOHSNHO-UHFFFAOYSA-N 0.000 description 1
- WUMKSBNWCCTRQY-UHFFFAOYSA-N 2-amino-4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-fluoro-1-phenylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(N)CC(F)N(CC1)CCC1(O)C1=CC=C(Cl)C=C1 WUMKSBNWCCTRQY-UHFFFAOYSA-N 0.000 description 1
- HKNLLLWBJYYFPO-UHFFFAOYSA-N 2-amino-4-[4-[(4-chlorophenyl)methyl]-4-hydroxypiperidin-1-yl]-4-fluoro-1-phenylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(N)CC(F)N(CC1)CCC1(O)CC1=CC=C(Cl)C=C1 HKNLLLWBJYYFPO-UHFFFAOYSA-N 0.000 description 1
- KBBXAWKSOHWBEE-UHFFFAOYSA-N 2-amino-4-fluoro-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-1-phenylbutan-1-one;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)C(N)CC(F)N(CC1)CCC1(O)C1=CC=CC(C(F)(F)F)=C1 KBBXAWKSOHWBEE-UHFFFAOYSA-N 0.000 description 1
- MBNBAODMHRPUKN-UHFFFAOYSA-N 2-fluoro-1-phenylbutan-1-one Chemical class CCC(F)C(=O)C1=CC=CC=C1 MBNBAODMHRPUKN-UHFFFAOYSA-N 0.000 description 1
- JIKWKFDKRLIYOB-UHFFFAOYSA-N 3-[1-(1,3-difluoro-4-oxo-4-phenylbutyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(F)CC(F)C(=O)C1=CC=CC=C1 JIKWKFDKRLIYOB-UHFFFAOYSA-N 0.000 description 1
- WPZXKMJNOGOGGK-UHFFFAOYSA-N 3-[1-(3-amino-1-fluoro-4-oxo-4-phenylbutyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(F)CC(N)C(=O)C1=CC=CC=C1 WPZXKMJNOGOGGK-UHFFFAOYSA-N 0.000 description 1
- UZWQSBWCIGCAFW-UHFFFAOYSA-N 3-[1-[3-(benzylamino)-1-fluoro-4-oxo-4-phenylbutyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(F)CC(C(=O)C=1C=CC=CC=1)NCC1=CC=CC=C1 UZWQSBWCIGCAFW-UHFFFAOYSA-N 0.000 description 1
- VBQZHLJGWSZPJU-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)-1-fluoro-4-oxo-4-phenylbutyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(F)CC(N(C)C)C(=O)C1=CC=CC=C1 VBQZHLJGWSZPJU-UHFFFAOYSA-N 0.000 description 1
- XEEXELMYYFQEEX-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-2,4-difluoro-1-phenylbutan-1-one Chemical compound C1CC2=CC=CC=C2CN1C(F)CC(F)C(=O)C1=CC=CC=C1 XEEXELMYYFQEEX-UHFFFAOYSA-N 0.000 description 1
- JQKGQYGCPCTZRY-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[3-[2-(2,4-difluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC1(C=2C(=CC(F)=CC=2)F)OCCO1 JQKGQYGCPCTZRY-UHFFFAOYSA-N 0.000 description 1
- BRBSASXSSNZAOK-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-1-[3-[2-(2,4-difluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol Chemical compound C1CN(CCCC2(OCCO2)C=2C(=CC(F)=CC=2)F)CCC1(O)CC1=CC=C(Cl)C=C1 BRBSASXSSNZAOK-UHFFFAOYSA-N 0.000 description 1
- XYIZMESTMQRVBG-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,4-difluoro-1-phenylbutan-1-one Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(F)CC(F)C(=O)C1=CC=CC=C1 XYIZMESTMQRVBG-UHFFFAOYSA-N 0.000 description 1
- JWQCIJZKMDSZTR-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2-(dimethylamino)-4-fluoro-1-phenylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(N(C)C)CC(F)N(CC1)CCC1(O)C1=CC=C(Cl)C=C1 JWQCIJZKMDSZTR-UHFFFAOYSA-N 0.000 description 1
- HICHDFKJIQBLMN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2-(ethylamino)-4-fluoro-1-phenylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(NCC)CC(F)N(CC1)CCC1(O)C1=CC=C(Cl)C=C1 HICHDFKJIQBLMN-UHFFFAOYSA-N 0.000 description 1
- NPQDNPUMNRKPLH-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-fluoro-1-phenyl-2-piperidin-1-ylbutan-1-one;hydrochloride Chemical compound Cl.C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1C(F)CC(C(=O)C=1C=CC=CC=1)N1CCCCC1 NPQDNPUMNRKPLH-UHFFFAOYSA-N 0.000 description 1
- WGIDNZKCSLCSJE-UHFFFAOYSA-N 4-chloro-1-phenylpiperidin-4-ol Chemical compound C1CC(O)(Cl)CCN1C1=CC=CC=C1 WGIDNZKCSLCSJE-UHFFFAOYSA-N 0.000 description 1
- GXWMHDATZPZISW-UHFFFAOYSA-N 4-fluoro-2-[[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-propan-2-ylamino]-1-phenylbutan-1-one Chemical compound OC1(CCN(CC1)N(C(C(=O)C1=CC=CC=C1)CCF)C(C)C)C1=CC(=CC=C1)C(F)(F)F GXWMHDATZPZISW-UHFFFAOYSA-N 0.000 description 1
- WCMDCJJRWHPVBX-UHFFFAOYSA-N 4-fluoro-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]-2-(methylamino)-1-phenylbutan-1-one Chemical compound OC1(CCN(CC1)C(CC(C(=O)C1=CC=CC=C1)NC)F)C1=CC(=CC=C1)C(F)(F)F WCMDCJJRWHPVBX-UHFFFAOYSA-N 0.000 description 1
- KUSDIZXILPWUHA-UHFFFAOYSA-N 8-[1-fluoro-3-(methylamino)-4-oxo-4-phenylbutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C=1C=CC=CC=1C(=O)C(NC)CC(F)N(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 KUSDIZXILPWUHA-UHFFFAOYSA-N 0.000 description 1
- ALVVSKXZHKHWOD-UHFFFAOYSA-N 8-[3-(dimethylamino)-1-fluoro-4-oxo-4-phenylbutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C=1C=CC=CC=1C(=O)C(N(C)C)CC(F)N(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 ALVVSKXZHKHWOD-UHFFFAOYSA-N 0.000 description 1
- AYPMLNIOQGRDFS-UHFFFAOYSA-N 8-[3-(ethylamino)-1-fluoro-4-oxo-4-phenylbutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C=1C=CC=CC=1C(=O)C(NCC)CC(F)N(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 AYPMLNIOQGRDFS-UHFFFAOYSA-N 0.000 description 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- AMOYLRHLBNNESR-UHFFFAOYSA-N Cl.Cl.Cl.COC1=C(C=CC=C1)N1CCN(CC1)C(CC(C(=O)C1=CC=CC=C1)N(C)C)F Chemical compound Cl.Cl.Cl.COC1=C(C=CC=C1)N1CCN(CC1)C(CC(C(=O)C1=CC=CC=C1)N(C)C)F AMOYLRHLBNNESR-UHFFFAOYSA-N 0.000 description 1
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- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- HSDZNCJUZBPKRS-UHFFFAOYSA-N O=C1NCN(C12CCN(CC2)C(CC(C(=O)C2=CC=CC=C2)N(C)CC2=CC=CC=C2)F)C2=CC=CC=C2 Chemical compound O=C1NCN(C12CCN(CC2)C(CC(C(=O)C2=CC=CC=C2)N(C)CC2=CC=CC=C2)F)C2=CC=CC=C2 HSDZNCJUZBPKRS-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940049920 malate Drugs 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
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 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 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
-
- 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
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
-
- 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI803812A FI803812L (fi) | 1972-03-18 | 1980-12-08 | Foerfarande foer framstaellning av butyrofenonderivat |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47027610A JPS5755714B2 (enrdf_load_stackoverflow) | 1972-03-18 | 1972-03-18 | |
| JP2761072 | 1972-03-18 | ||
| JP47057249A JPS4914476A (enrdf_load_stackoverflow) | 1972-06-07 | 1972-06-07 | |
| JP5724972 | 1972-06-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58636B FI58636B (fi) | 1980-11-28 |
| FI58636C true FI58636C (fi) | 1981-03-10 |
Family
ID=26365557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI82473A FI58636C (fi) | 1972-03-18 | 1973-03-16 | Foerfarande foer framstaellning av butyrofenonderivat |
Country Status (10)
| Country | Link |
|---|---|
| AU (1) | AU470114B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1024984A (enrdf_load_stackoverflow) |
| CH (2) | CH599939A5 (enrdf_load_stackoverflow) |
| FI (1) | FI58636C (enrdf_load_stackoverflow) |
| FR (1) | FR2183683B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1423576A (enrdf_load_stackoverflow) |
| HU (1) | HU167671B (enrdf_load_stackoverflow) |
| NL (1) | NL7303854A (enrdf_load_stackoverflow) |
| NO (2) | NO144068C (enrdf_load_stackoverflow) |
| SE (1) | SE419441B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS595587B2 (ja) * | 1974-04-18 | 1984-02-06 | 住友化学工業株式会社 | シンキナブチロフエノンユウドウタイ オヨビ ソノエン ノ セイホウ |
| JPS5116677A (ja) * | 1974-07-29 | 1976-02-10 | Sumitomo Chemical Co | Shinkinabuchirofuenonjudotai oyobi sonosanfukaennoseiho |
| FR2530632A1 (fr) * | 1982-07-26 | 1984-01-27 | Bouchara Emile | Nouveaux derives substitues du 2,5-diamino 1,4-diazole, leurs procedes de preparation et les compositions pharmaceutiques en renfermant |
| US4569933A (en) * | 1984-04-13 | 1986-02-11 | Cornu Pierre Jean | Antihypertensive substituted derivatives of 2,5-diamino 1,4-diazole |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI52216C (fi) * | 1969-07-16 | 1977-07-11 | Sumitomo Chemical Co | Menetelmä gamma-piperidinobutyrofenonijohdannaisten valmistamiseksi. |
| FR2081493B1 (enrdf_load_stackoverflow) * | 1970-02-06 | 1975-04-18 | Sumitomo Chemical Co | |
| DE2110534C3 (de) * | 1970-03-06 | 1979-03-08 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | γ-Piperazinobutyrophenonderivate, Verfahren zu ihrer Herstellung und Arzneipräparate |
| US3799932A (en) * | 1970-03-20 | 1974-03-26 | Sumitomo Chemical Co | Gamma-piperidinobutyrophenones |
-
1973
- 1973-03-16 SE SE7303729A patent/SE419441B/xx unknown
- 1973-03-16 NO NO107273A patent/NO144068C/no unknown
- 1973-03-16 GB GB1280473A patent/GB1423576A/en not_active Expired
- 1973-03-16 HU HUSU000807 patent/HU167671B/hu unknown
- 1973-03-16 CH CH514476A patent/CH599939A5/xx not_active IP Right Cessation
- 1973-03-16 CA CA166,245A patent/CA1024984A/en not_active Expired
- 1973-03-16 CH CH389373A patent/CH589626A5/xx not_active IP Right Cessation
- 1973-03-16 FI FI82473A patent/FI58636C/fi active
- 1973-03-16 FR FR7309598A patent/FR2183683B1/fr not_active Expired
- 1973-03-19 AU AU53468/73A patent/AU470114B2/en not_active Expired
- 1973-03-19 NL NL7303854A patent/NL7303854A/xx not_active Application Discontinuation
- 1973-08-15 NO NO324273A patent/NO144069C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7303854A (enrdf_load_stackoverflow) | 1973-09-20 |
| NO144068C (no) | 1981-06-17 |
| CH599939A5 (enrdf_load_stackoverflow) | 1978-06-15 |
| FR2183683B1 (enrdf_load_stackoverflow) | 1976-12-31 |
| HU167671B (enrdf_load_stackoverflow) | 1975-11-28 |
| FI58636B (fi) | 1980-11-28 |
| NO144068B (no) | 1981-03-09 |
| CH589626A5 (enrdf_load_stackoverflow) | 1977-07-15 |
| NO144069C (no) | 1981-06-17 |
| FR2183683A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| SE419441B (sv) | 1981-08-03 |
| NO144069B (no) | 1981-03-09 |
| AU470114B2 (en) | 1976-03-04 |
| GB1423576A (en) | 1976-02-04 |
| CA1024984A (en) | 1978-01-24 |
| AU5346873A (en) | 1974-09-19 |
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