NO881221L - Styrylketoner. - Google Patents
Styrylketoner.Info
- Publication number
- NO881221L NO881221L NO881221A NO881221A NO881221L NO 881221 L NO881221 L NO 881221L NO 881221 A NO881221 A NO 881221A NO 881221 A NO881221 A NO 881221A NO 881221 L NO881221 L NO 881221L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- residue
- lower alkyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 239000001257 hydrogen Substances 0.000 claims abstract description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 88
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 64
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 3
- 125000005109 alkynylthio group Chemical group 0.000 claims abstract description 3
- -1 styryl ketones Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 208000025865 Ulcer Diseases 0.000 claims description 8
- 210000001198 duodenum Anatomy 0.000 claims description 8
- 150000004702 methyl esters Chemical class 0.000 claims description 8
- 231100000397 ulcer Toxicity 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 150000007514 bases Chemical class 0.000 claims description 5
- JTVLIFCENLZXFQ-WVNGBEFXSA-N (2e,5e)-6-(4-methoxyphenyl)-4-oxohexa-2,5-dienoic acid Chemical compound COC1=CC=C(\C=C\C(=O)\C=C\C(O)=O)C=C1 JTVLIFCENLZXFQ-WVNGBEFXSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- BTMWCMREWGREPW-ZMDKPMJNSA-N methyl (2z,5e)-6-(4-methoxyphenyl)-4-oxohexa-2,5-dienoate Chemical compound COC(=O)\C=C/C(=O)/C=C/C1=CC=C(OC)C=C1 BTMWCMREWGREPW-ZMDKPMJNSA-N 0.000 claims description 4
- MJINYLAISWCCSV-BSWSSELBSA-N (2e,5e)-6-(3-methoxyphenyl)-4-oxohexa-2,5-dienoic acid Chemical compound COC1=CC=CC(\C=C\C(=O)\C=C\C(O)=O)=C1 MJINYLAISWCCSV-BSWSSELBSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 5
- YPYJVJLDMPNYAL-GORDUTHDSA-N (e)-6-(4-methoxyphenyl)-4-oxohex-5-en-2-ynoic acid Chemical compound COC1=CC=C(\C=C\C(=O)C#CC(O)=O)C=C1 YPYJVJLDMPNYAL-GORDUTHDSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 106
- 239000000243 solution Substances 0.000 description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000012074 organic phase Substances 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 239000002585 base Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 18
- 239000003480 eluent Substances 0.000 description 17
- 238000003818 flash chromatography Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 239000007903 gelatin capsule Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000052 vinegar Substances 0.000 description 12
- 235000021419 vinegar Nutrition 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 6
- 239000003791 organic solvent mixture Substances 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 4
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-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
- 230000002378 acidificating effect Effects 0.000 description 4
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 230000006806 disease prevention Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QKBBTQJLUGADEG-UHFFFAOYSA-N 3-(1-ethoxyethoxy)prop-1-yne Chemical compound CCOC(C)OCC#C QKBBTQJLUGADEG-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- UALZRFRMEYMLCQ-UHFFFAOYSA-N 3-methyl-1-prop-2-ynoxybut-2-ene Chemical compound CC(C)=CCOCC#C UALZRFRMEYMLCQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000009835 boiling Methods 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
- 239000008298 dragée Substances 0.000 description 3
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 3
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000003285 pharmacodynamic effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- XSZOHWKCBFYVCW-ZICOWINBSA-N (2e,5e)-6-(4-fluorophenyl)-4-oxohexa-2,5-dienoic acid Chemical compound OC(=O)\C=C\C(=O)\C=C\C1=CC=C(F)C=C1 XSZOHWKCBFYVCW-ZICOWINBSA-N 0.000 description 2
- JTVLIFCENLZXFQ-VPVKMTRZSA-N (2z,5e)-6-(4-methoxyphenyl)-4-oxohexa-2,5-dienoic acid Chemical compound COC1=CC=C(\C=C\C(=O)\C=C/C(O)=O)C=C1 JTVLIFCENLZXFQ-VPVKMTRZSA-N 0.000 description 2
- XYKCZTUFYUYBNB-AATRIKPKSA-N (e)-1-bromo-4-(3-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=CC(\C=C\C(=O)CBr)=C1 XYKCZTUFYUYBNB-AATRIKPKSA-N 0.000 description 2
- CDWROTZMPJSYFY-AATRIKPKSA-N (e)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(\C=C\C(C)=O)C(OC)=C1OC CDWROTZMPJSYFY-AATRIKPKSA-N 0.000 description 2
- YGGXEEJZKRLTGV-SNAWJCMRSA-N (e)-4-(2,5-dimethoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(OC)C(\C=C\C(C)=O)=C1 YGGXEEJZKRLTGV-SNAWJCMRSA-N 0.000 description 2
- RFSHGORINKEBNU-RMKNXTFCSA-N (e)-6,6-diethoxy-1-(4-methoxyphenyl)hex-1-en-4-yn-3-ol Chemical compound CCOC(OCC)C#CC(O)\C=C\C1=CC=C(OC)C=C1 RFSHGORINKEBNU-RMKNXTFCSA-N 0.000 description 2
- DTCWDLNXXVWGPI-RMKNXTFCSA-N (e)-6,6-diethoxy-1-(4-methoxyphenyl)hex-1-en-4-yn-3-one Chemical compound CCOC(OCC)C#CC(=O)\C=C\C1=CC=C(OC)C=C1 DTCWDLNXXVWGPI-RMKNXTFCSA-N 0.000 description 2
- LCDAHMFCPGOBQH-MDZDMXLPSA-N (e)-6-(1-ethoxyethoxy)-1-(3,4,5-trimethoxyphenyl)hex-1-en-4-yn-3-one Chemical compound CCOC(C)OCC#CC(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1 LCDAHMFCPGOBQH-MDZDMXLPSA-N 0.000 description 2
- NXDDOSKRXDWDJM-JXMROGBWSA-N (e)-6-(1-ethoxyethoxy)-1-(4-methoxyphenyl)hex-1-en-4-yn-3-one Chemical compound CCOC(C)OCC#CC(=O)\C=C\C1=CC=C(OC)C=C1 NXDDOSKRXDWDJM-JXMROGBWSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- AJUFIDDKYVJRKD-BLHCBFLLSA-N 2-(2-methoxyethoxy)ethyl (2e,5e)-6-(3-methoxyphenyl)-4-oxohexa-2,5-dienoate Chemical compound COCCOCCOC(=O)\C=C\C(=O)\C=C\C1=CC=CC(OC)=C1 AJUFIDDKYVJRKD-BLHCBFLLSA-N 0.000 description 2
- CRDPVTSLDONUDT-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCCOCCOC)C1=CC=CC=C1 CRDPVTSLDONUDT-UHFFFAOYSA-N 0.000 description 2
- XUWBNDYKSQEEMS-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-bromoacetate Chemical compound COCCOCCOC(=O)CBr XUWBNDYKSQEEMS-UHFFFAOYSA-N 0.000 description 2
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 2
- YTFVRYKNXDADBI-SNAWJCMRSA-N 3,4,5-trimethoxycinnamic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-SNAWJCMRSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- AMATXUCYHHHHHB-UHFFFAOYSA-N 5,5-dibromo-1,3-diazinane-2,4,6-trione Chemical compound BrC1(Br)C(=O)NC(=O)NC1=O AMATXUCYHHHHHB-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YTFVRYKNXDADBI-UHFFFAOYSA-N O-Methylsinapic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FGABGYHLPYZJNG-UHFFFAOYSA-M [2-[2-(2-methoxyethoxy)ethoxy]-2-oxoethyl]-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)OCCOCCOC)C1=CC=CC=C1 FGABGYHLPYZJNG-UHFFFAOYSA-M 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 2
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- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/603—Unsaturated compounds containing a keto groups being part of a ring of a six-membered ring, e.g. quinone methides
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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
- C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
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- 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
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH107187 | 1987-03-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO881221D0 NO881221D0 (no) | 1988-03-18 |
| NO881221L true NO881221L (no) | 1988-09-21 |
Family
ID=4201771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO881221A NO881221L (no) | 1987-03-20 | 1988-03-18 | Styrylketoner. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4927958A (da) |
| EP (1) | EP0282897A3 (da) |
| KR (1) | KR880011064A (da) |
| AU (1) | AU1307588A (da) |
| DK (1) | DK59688A (da) |
| FI (1) | FI880811A7 (da) |
| HU (1) | HUT46643A (da) |
| IL (1) | IL85723A0 (da) |
| MC (1) | MC1917A1 (da) |
| NO (1) | NO881221L (da) |
| PT (1) | PT87023B (da) |
| ZA (1) | ZA881809B (da) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2276204A (en) * | 1940-01-02 | 1942-03-10 | Kilgore Dev Corp | Chemical light filter |
| US4304728A (en) * | 1979-04-05 | 1981-12-08 | Lilly Industries Limited | 6-Substituted pyranone compounds and their use as pharmaceuticals |
-
1988
- 1988-02-05 DK DK059688A patent/DK59688A/da not_active Application Discontinuation
- 1988-02-22 FI FI880811A patent/FI880811A7/fi not_active Application Discontinuation
- 1988-03-09 EP EP88103735A patent/EP0282897A3/de not_active Withdrawn
- 1988-03-14 ZA ZA881809A patent/ZA881809B/xx unknown
- 1988-03-14 IL IL85723A patent/IL85723A0/xx unknown
- 1988-03-14 AU AU13075/88A patent/AU1307588A/en not_active Abandoned
- 1988-03-16 HU HU881242A patent/HUT46643A/hu unknown
- 1988-03-17 US US07/169,570 patent/US4927958A/en not_active Expired - Fee Related
- 1988-03-17 MC MC881961A patent/MC1917A1/fr unknown
- 1988-03-18 PT PT87023A patent/PT87023B/pt not_active IP Right Cessation
- 1988-03-18 NO NO881221A patent/NO881221L/no unknown
- 1988-03-19 KR KR1019880002923A patent/KR880011064A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ZA881809B (en) | 1988-09-20 |
| PT87023A (pt) | 1988-04-01 |
| PT87023B (pt) | 1992-06-30 |
| NO881221D0 (no) | 1988-03-18 |
| EP0282897A2 (de) | 1988-09-21 |
| FI880811A7 (fi) | 1988-09-21 |
| FI880811A0 (fi) | 1988-02-22 |
| US4927958A (en) | 1990-05-22 |
| KR880011064A (ko) | 1988-10-26 |
| AU1307588A (en) | 1988-09-22 |
| IL85723A0 (en) | 1988-08-31 |
| MC1917A1 (fr) | 1989-04-06 |
| HUT46643A (en) | 1988-11-28 |
| DK59688D0 (da) | 1988-02-05 |
| DK59688A (da) | 1988-09-21 |
| EP0282897A3 (de) | 1989-10-04 |
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