NO881220L - Propiolofenonderivater. - Google Patents
Propiolofenonderivater.Info
- Publication number
- NO881220L NO881220L NO881220A NO881220A NO881220L NO 881220 L NO881220 L NO 881220L NO 881220 A NO881220 A NO 881220A NO 881220 A NO881220 A NO 881220A NO 881220 L NO881220 L NO 881220L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- hydroxy
- lower alkyl
- compound
- Prior art date
Links
- 239000001257 hydrogen Substances 0.000 claims description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- -1 N,N-diisopropyl-3-(2-hydroxy-5-methylbenzoyl)propiolamide Chemical compound 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000006239 protecting group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- DXGYNPZYNMZNFZ-UHFFFAOYSA-N 4-hydroxy-1-(3,4,5-trimethoxyphenyl)but-2-yn-1-one Chemical compound COC1=CC(C(=O)C#CCO)=CC(OC)=C1OC DXGYNPZYNMZNFZ-UHFFFAOYSA-N 0.000 claims description 6
- JITPLZPWKYUTDM-UHFFFAOYSA-N 1-phenylprop-2-yn-1-one Chemical class C#CC(=O)C1=CC=CC=C1 JITPLZPWKYUTDM-UHFFFAOYSA-N 0.000 claims description 5
- 150000007514 bases Chemical class 0.000 claims description 5
- VEIQXRUUKUMXBH-UHFFFAOYSA-N methyl 4-oxo-4-(2,3,4-trimethoxyphenyl)but-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(OC)C(OC)=C1OC VEIQXRUUKUMXBH-UHFFFAOYSA-N 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- SJSYSZDNFLDRJF-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-oxobut-2-ynoic acid Chemical compound COC1=CC=C(C(=O)C#CC(O)=O)C=C1 SJSYSZDNFLDRJF-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 210000001198 duodenum Anatomy 0.000 claims description 4
- ZRXFZIUWASCOSM-UHFFFAOYSA-N methyl 4-(2,5-dimethoxyphenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC(OC)=CC=C1OC ZRXFZIUWASCOSM-UHFFFAOYSA-N 0.000 claims description 4
- LUTPFTGLMDUTLN-UHFFFAOYSA-N methyl 4-(4-hydroxyphenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(O)C=C1 LUTPFTGLMDUTLN-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- LHLDLBINFPOOJM-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-(1,3-benzodioxol-5-yl)-4-oxobut-2-ynoate Chemical compound COCCOCCOC(=O)C#CC(=O)C1=CC=C2OCOC2=C1 LHLDLBINFPOOJM-UHFFFAOYSA-N 0.000 claims description 3
- ZBNKLKFXEUOMTH-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-(4-methoxyphenyl)-4-oxobut-2-ynoate Chemical compound COCCOCCOC(=O)C#CC(=O)C1=CC=C(OC)C=C1 ZBNKLKFXEUOMTH-UHFFFAOYSA-N 0.000 claims description 3
- TZJAKMDUPIVQGF-UHFFFAOYSA-N 4-(2,5-dimethoxyphenyl)-4-oxobut-2-ynoic acid Chemical compound COC1=CC=C(OC)C(C(=O)C#CC(O)=O)=C1 TZJAKMDUPIVQGF-UHFFFAOYSA-N 0.000 claims description 3
- DVYJGHJRGDKUOY-UHFFFAOYSA-N 4-methoxy-1-(3-methylphenyl)but-2-yn-1-one Chemical compound COCC#CC(=O)C1=CC=CC(C)=C1 DVYJGHJRGDKUOY-UHFFFAOYSA-N 0.000 claims description 3
- BDWYNRUHYHPGFU-UHFFFAOYSA-N 4-methoxy-4-methyl-1-(3-methylphenyl)pent-2-yn-1-one Chemical compound COC(C)(C)C#CC(=O)C1=CC=CC(C)=C1 BDWYNRUHYHPGFU-UHFFFAOYSA-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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- VXVIUEDPUSZPHL-UHFFFAOYSA-N methyl 4-(2,6-dimethoxyphenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=C(OC)C=CC=C1OC VXVIUEDPUSZPHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000005109 alkynylthio group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- FYLGRSWUSRVMHD-UHFFFAOYSA-N 4-methoxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one Chemical compound COC1=CC=C(C(=O)C#CC(C)(C)OC)C=C1 FYLGRSWUSRVMHD-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 366
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 241
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 217
- 239000000243 solution Substances 0.000 description 204
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 188
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 128
- 239000011541 reaction mixture Substances 0.000 description 97
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 95
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 94
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 86
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 82
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 74
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 64
- 235000019341 magnesium sulphate Nutrition 0.000 description 64
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
- 239000000741 silica gel Substances 0.000 description 59
- 229910002027 silica gel Inorganic materials 0.000 description 59
- 239000012074 organic phase Substances 0.000 description 56
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 50
- 239000003480 eluent Substances 0.000 description 50
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 47
- 239000000203 mixture Substances 0.000 description 47
- 239000003921 oil Substances 0.000 description 47
- 235000019198 oils Nutrition 0.000 description 47
- 239000012071 phase Substances 0.000 description 46
- 238000003818 flash chromatography Methods 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 239000000725 suspension Substances 0.000 description 37
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 33
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- 238000002425 crystallisation Methods 0.000 description 28
- 230000008025 crystallization Effects 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- 235000002639 sodium chloride Nutrition 0.000 description 26
- 229960000583 acetic acid Drugs 0.000 description 25
- 229910052786 argon Inorganic materials 0.000 description 25
- 239000002585 base Substances 0.000 description 21
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 18
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 15
- 239000000052 vinegar Substances 0.000 description 13
- 235000021419 vinegar Nutrition 0.000 description 13
- 239000007903 gelatin capsule Substances 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- QKBBTQJLUGADEG-UHFFFAOYSA-N 3-(1-ethoxyethoxy)prop-1-yne Chemical compound CCOC(C)OCC#C QKBBTQJLUGADEG-UHFFFAOYSA-N 0.000 description 10
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 239000003791 organic solvent mixture Substances 0.000 description 8
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- OEPXZDSQDDXJOA-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl prop-2-ynoate Chemical compound COCCOCCOC(=O)C#C OEPXZDSQDDXJOA-UHFFFAOYSA-N 0.000 description 5
- CMWWOLASCZJNCX-UHFFFAOYSA-N 3-methylbut-2-enyl prop-2-ynoate Chemical compound CC(C)=CCOC(=O)C#C CMWWOLASCZJNCX-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 5
- UALZRFRMEYMLCQ-UHFFFAOYSA-N 3-methyl-1-prop-2-ynoxybut-2-ene Chemical compound CC(C)=CCOCC#C UALZRFRMEYMLCQ-UHFFFAOYSA-N 0.000 description 4
- QNTUJJNRKASIKH-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-4-oxobut-2-ynoic acid Chemical compound OC(=O)C#CC(=O)C1=CC=C2OCOC2=C1 QNTUJJNRKASIKH-UHFFFAOYSA-N 0.000 description 4
- KXVPKRFLLJHURF-UHFFFAOYSA-N 4-(1-ethoxyethoxy)-1-(2,3,4-trimethoxyphenyl)but-2-yn-1-one Chemical compound CCOC(C)OCC#CC(=O)C1=CC=C(OC)C(OC)=C1OC KXVPKRFLLJHURF-UHFFFAOYSA-N 0.000 description 4
- PSADZENFJWPVLG-UHFFFAOYSA-N 4-(1-ethoxyethoxy)-1-(4-fluorophenyl)but-2-yn-1-one Chemical compound CCOC(C)OCC#CC(=O)C1=CC=C(F)C=C1 PSADZENFJWPVLG-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XKRFYHLGVUSROY-BJUDXGSMSA-N argon-39 atom Chemical compound [39Ar] XKRFYHLGVUSROY-BJUDXGSMSA-N 0.000 description 4
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 208000000718 duodenal ulcer Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- ZJIYVBNWDDZRMJ-UHFFFAOYSA-N methyl 4-oxo-4-(3,4,5-trimethoxyphenyl)but-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZJIYVBNWDDZRMJ-UHFFFAOYSA-N 0.000 description 4
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BYLJURYDPKPQBZ-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-4-hydroxybut-2-yn-1-one Chemical compound OCC#CC(=O)C1=CC=C2OCOC2=C1 BYLJURYDPKPQBZ-UHFFFAOYSA-N 0.000 description 3
- JIYGMAWCIHEHSW-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(1-ethoxyethoxy)but-2-yn-1-ol Chemical compound CCOC(C)OCC#CC(O)C1=CC=C(Cl)C=C1 JIYGMAWCIHEHSW-UHFFFAOYSA-N 0.000 description 3
- LBGDMCMFZUWEQZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-hydroxybut-2-yn-1-one Chemical compound OCC#CC(=O)C1=CC=C(Cl)C=C1 LBGDMCMFZUWEQZ-UHFFFAOYSA-N 0.000 description 3
- FGFCHQLDHPBBHA-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-hydroxybut-2-yn-1-one Chemical compound OCC#CC(=O)C1=CC=C(F)C=C1 FGFCHQLDHPBBHA-UHFFFAOYSA-N 0.000 description 3
- ZKASIXNQCZVAAX-UHFFFAOYSA-N 4-hydroxy-1-(2,3,4-trimethoxyphenyl)but-2-yn-1-one Chemical compound COC1=CC=C(C(=O)C#CCO)C(OC)=C1OC ZKASIXNQCZVAAX-UHFFFAOYSA-N 0.000 description 3
- BFVVMRRQWCJBAY-UHFFFAOYSA-N 4-hydroxy-1-(4-methoxyphenyl)but-2-yn-1-one Chemical compound COC1=CC=C(C(=O)C#CCO)C=C1 BFVVMRRQWCJBAY-UHFFFAOYSA-N 0.000 description 3
- NYDSATNBJPHNRB-UHFFFAOYSA-N 4-hydroxy-1-(4-methylphenyl)but-2-yn-1-one Chemical compound CC1=CC=C(C(=O)C#CCO)C=C1 NYDSATNBJPHNRB-UHFFFAOYSA-N 0.000 description 3
- FCWQANOICITUEK-UHFFFAOYSA-N 4-hydroxy-1-(4-methylsulfanylphenyl)but-2-yn-1-one Chemical compound CSC1=CC=C(C(=O)C#CCO)C=C1 FCWQANOICITUEK-UHFFFAOYSA-N 0.000 description 3
- OLQUVDZOUKFEMY-UHFFFAOYSA-N 4-oxo-4-(2,3,4-trimethoxyphenyl)but-2-ynoic acid Chemical compound COC1=CC=C(C(=O)C#CC(O)=O)C(OC)=C1OC OLQUVDZOUKFEMY-UHFFFAOYSA-N 0.000 description 3
- LKMYKSYOKPXSLX-UHFFFAOYSA-N 4-oxo-4-(3,4,5-trimethoxyphenyl)but-2-ynoic acid Chemical compound COC1=CC(C(=O)C#CC(O)=O)=CC(OC)=C1OC LKMYKSYOKPXSLX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000002378 acidificating effect Effects 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
- 239000012043 crude product Substances 0.000 description 3
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- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
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- QPVWAEJSMHLHLA-UHFFFAOYSA-N methyl 4-(2,3-dihydro-1h-inden-5-yl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C2CCCC2=C1 QPVWAEJSMHLHLA-UHFFFAOYSA-N 0.000 description 1
- ALNNWERTFHBQFA-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(Cl)C=C1 ALNNWERTFHBQFA-UHFFFAOYSA-N 0.000 description 1
- JKGUUADORVKPOJ-UHFFFAOYSA-N methyl 4-(4-methoxyphenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(OC)C=C1 JKGUUADORVKPOJ-UHFFFAOYSA-N 0.000 description 1
- KZEPKSJCKHRDKP-UHFFFAOYSA-N methyl 4-(4-methylphenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(C)C=C1 KZEPKSJCKHRDKP-UHFFFAOYSA-N 0.000 description 1
- YCQYGKFFXDWHFM-UHFFFAOYSA-N methyl 4-(4-methylsulfanylphenyl)-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(SC)C=C1 YCQYGKFFXDWHFM-UHFFFAOYSA-N 0.000 description 1
- JGXKOGOFQNBIOQ-UHFFFAOYSA-N methyl 4-[4-(dimethylamino)phenyl]-4-oxobut-2-ynoate Chemical compound COC(=O)C#CC(=O)C1=CC=C(N(C)C)C=C1 JGXKOGOFQNBIOQ-UHFFFAOYSA-N 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 125000004043 oxo group Chemical group O=* 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 210000001187 pylorus Anatomy 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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Classifications
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- 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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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- 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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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
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- 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
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- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
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- 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
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
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- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
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- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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- 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
- C07D317/54—Radicals substituted by oxygen atoms
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- 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
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH107287 | 1987-03-20 |
Publications (2)
| Publication Number | Publication Date |
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| NO881220D0 NO881220D0 (no) | 1988-03-18 |
| NO881220L true NO881220L (no) | 1988-09-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO881220A NO881220L (no) | 1987-03-20 | 1988-03-18 | Propiolofenonderivater. |
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| Country | Link |
|---|---|
| US (1) | US4929741A (da) |
| EP (1) | EP0282898A3 (da) |
| KR (1) | KR880011063A (da) |
| AU (1) | AU1307688A (da) |
| DK (1) | DK49688A (da) |
| FI (1) | FI880812A7 (da) |
| HU (1) | HUT46644A (da) |
| IL (1) | IL85722A0 (da) |
| MC (1) | MC1916A1 (da) |
| NO (1) | NO881220L (da) |
| PT (1) | PT87024B (da) |
| YU (1) | YU55088A (da) |
| ZA (1) | ZA881808B (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8712200D0 (en) * | 1987-05-21 | 1987-07-22 | Research Corp Ltd | Substituted phenone |
| US4847303A (en) * | 1987-11-23 | 1989-07-11 | The Procter & Gamble Company | Tert-butylphenyl compounds useful as anti-inflammatory agents |
| MTP1031B (en) * | 1987-12-24 | 1990-10-04 | Orion Yhtymae Oy | New use of cathecol-o-methyl transferase (comt) inhibitors and their physiologically acceptable salts and esters |
| US5217981A (en) * | 1989-12-18 | 1993-06-08 | G. D. Searle & Co. | LTB4 synthesis inhibitors |
| AU653957B2 (en) * | 1990-09-20 | 1994-10-20 | Merrell Dow Pharmaceuticals Inc. | 1-aryl-3-pyridinyl-2-propene-1-ones |
| US5248825A (en) * | 1990-09-20 | 1993-09-28 | Merrell Dow Pharmaceuticals Inc. | Calcium uptake inhibitors |
| US5223518A (en) * | 1990-09-20 | 1993-06-29 | Merrell Dow Pharmaceuticals Inc. | 1-phenyl-3-aryl-2-propyne-1-one useful as calcium uptake inhibitors |
| US5112864A (en) * | 1991-05-30 | 1992-05-12 | G. D. Searle & Co. | PLA2 inhibitors as antiinflammatories |
| US5356919A (en) * | 1991-05-30 | 1994-10-18 | G. D. Searle & Co. | Leukotriene B4 synthesis inhibitors |
| TW312688B (da) * | 1993-08-02 | 1997-08-11 | Mitsubishi Chem Corp | |
| KR19990015054A (ko) * | 1997-08-01 | 1999-03-05 | 구광시 | 페닐프로피온산 유도체의 제조방법 |
| EP2320878B1 (de) * | 2008-09-04 | 2015-02-25 | Maria Clementine Martin Klosterfrau Vertriebsgesellschaft mbH | Monoterpene für die behandlung von atemwegserkrankungen, insbesondere bronchopulmonalen erkrankungen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3754021A (en) * | 1968-05-29 | 1973-08-21 | Merck & Co Inc | 4-keto-4-(3-chloro-4'-cyclohexyl)phenylbutyric acid and related compounds |
| BE758735A (fr) * | 1969-11-14 | 1971-05-10 | Hoffmann La Roche | Composes acetyleniques |
| EP0022321A1 (en) * | 1979-07-10 | 1981-01-14 | Beecham Group Plc | Benzene derivatives, their preparation and use in pharmaceutical compositions |
| FR2481118A1 (fr) * | 1980-04-24 | 1981-10-30 | Roussel Uclaf | Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique |
| FR2504127B1 (fr) * | 1981-04-17 | 1985-07-19 | Roussel Uclaf | Nouveaux derives d'acides phenyl aliphatique carboxyliques, procede pour leur preparation et leur application comme medicaments |
| IT1171604B (it) * | 1981-10-22 | 1987-06-10 | Roussel Maestretti Spa | Derivati di acido 4-fenil-4-ossobuten-2-oico dotati di proprieta' farmacologiche e loro procedimento di preparazione |
| IT1169783B (it) * | 1983-08-25 | 1987-06-03 | Roussel Maestretti Spa | Derivati dell' acido 4-fenil 4-osso-buten 2-oico, loro procedimento di preparazione e loro applicazione come prodotti medicinali |
| EP0157740B1 (de) * | 1984-04-04 | 1990-06-27 | Ciba-Geigy Ag | Glycidyloxydiketone |
| US4624964A (en) * | 1985-03-27 | 1986-11-25 | E. I. Du Pont De Nemours And Company | Aryl oxo-alkynoates as 5-lipoxygenase inhibitors |
| US4708966A (en) * | 1986-06-27 | 1987-11-24 | The Procter & Gamble Company | Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation |
-
1988
- 1988-02-01 DK DK049688A patent/DK49688A/da not_active Application Discontinuation
- 1988-02-22 FI FI880812A patent/FI880812A7/fi not_active Application Discontinuation
- 1988-03-09 EP EP88103738A patent/EP0282898A3/de not_active Withdrawn
- 1988-03-14 AU AU13076/88A patent/AU1307688A/en not_active Abandoned
- 1988-03-14 IL IL85722A patent/IL85722A0/xx unknown
- 1988-03-14 ZA ZA881808A patent/ZA881808B/xx unknown
- 1988-03-16 HU HU881241A patent/HUT46644A/hu unknown
- 1988-03-17 US US07/169,643 patent/US4929741A/en not_active Expired - Fee Related
- 1988-03-17 MC MC881960A patent/MC1916A1/fr unknown
- 1988-03-18 PT PT87024A patent/PT87024B/pt not_active IP Right Cessation
- 1988-03-18 YU YU00550/88A patent/YU55088A/xx unknown
- 1988-03-18 NO NO881220A patent/NO881220L/no unknown
- 1988-03-18 KR KR1019880002846A patent/KR880011063A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PT87024B (pt) | 1992-07-31 |
| NO881220D0 (no) | 1988-03-18 |
| YU55088A (en) | 1990-02-28 |
| US4929741A (en) | 1990-05-29 |
| EP0282898A3 (de) | 1989-10-18 |
| MC1916A1 (fr) | 1989-04-06 |
| PT87024A (pt) | 1988-04-01 |
| DK49688A (da) | 1988-09-21 |
| FI880812A7 (fi) | 1988-09-21 |
| ZA881808B (en) | 1988-09-20 |
| IL85722A0 (en) | 1988-08-31 |
| DK49688D0 (da) | 1988-02-01 |
| AU1307688A (en) | 1988-09-22 |
| HUT46644A (en) | 1988-11-28 |
| FI880812A0 (fi) | 1988-02-22 |
| EP0282898A2 (de) | 1988-09-21 |
| KR880011063A (ko) | 1988-10-26 |
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