CA1195691A - Phenyl-alkanoic acid derivative and preparation thereof - Google Patents
Phenyl-alkanoic acid derivative and preparation thereofInfo
- Publication number
- CA1195691A CA1195691A CA000368943A CA368943A CA1195691A CA 1195691 A CA1195691 A CA 1195691A CA 000368943 A CA000368943 A CA 000368943A CA 368943 A CA368943 A CA 368943A CA 1195691 A CA1195691 A CA 1195691A
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutically acceptable
- acceptable salts
- whenever prepared
- obvious chemical
- chemical equivalent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 100
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000005544 phthalimido group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- -1 cyano, amino Chemical group 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 50
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- ZFYXXQZNATZREN-UHFFFAOYSA-N 7-(2-methylphenoxy)-3h-1-benzofuran-2-one Chemical compound CC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2 ZFYXXQZNATZREN-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ZZWIUBRKIMTOEU-UHFFFAOYSA-N 2-[7-(2-methylphenoxy)-2-oxo-3h-1-benzofuran-3-yl]isoindole-1,3-dione Chemical compound CC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2N1C(=O)C2=CC=CC=C2C1=O ZZWIUBRKIMTOEU-UHFFFAOYSA-N 0.000 claims description 2
- YHOJOUSBZSAMGC-UHFFFAOYSA-N 7-(2-chlorophenoxy)-3-ethyl-3h-1-benzofuran-2-one Chemical compound CCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1Cl YHOJOUSBZSAMGC-UHFFFAOYSA-N 0.000 claims description 2
- XLNHMQZCSHRONP-UHFFFAOYSA-N 7-(3-chlorophenoxy)-3h-1-benzofuran-2-one Chemical compound ClC1=CC=CC(OC=2C=3OC(=O)CC=3C=CC=2)=C1 XLNHMQZCSHRONP-UHFFFAOYSA-N 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- CWDLYPSLHIFZFS-UHFFFAOYSA-N 3,3-dimethyl-7-(2-methylphenoxy)-1-benzofuran-2-one Chemical compound CC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2(C)C CWDLYPSLHIFZFS-UHFFFAOYSA-N 0.000 claims 1
- GXCOVSHYNNZZAV-UHFFFAOYSA-N 3-butyl-7-(2-methylphenoxy)-3h-1-benzofuran-2-one Chemical compound CCCCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C GXCOVSHYNNZZAV-UHFFFAOYSA-N 0.000 claims 1
- XFXDRAUHAUGFGN-UHFFFAOYSA-N 3-ethyl-7-(2-methylphenoxy)-3h-1-benzofuran-2-one Chemical compound CCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C XFXDRAUHAUGFGN-UHFFFAOYSA-N 0.000 claims 1
- HIZSVBMKQMMEKH-UHFFFAOYSA-N 3-heptyl-7-(2-methylphenoxy)-3h-1-benzofuran-2-one Chemical compound CCCCCCCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C HIZSVBMKQMMEKH-UHFFFAOYSA-N 0.000 claims 1
- PRNNHJOPSISIMS-UHFFFAOYSA-N 3-hexyl-7-(2-methylphenoxy)-3h-1-benzofuran-2-one Chemical compound CCCCCCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C PRNNHJOPSISIMS-UHFFFAOYSA-N 0.000 claims 1
- FXTGWXLGIKSPSU-UHFFFAOYSA-N 3-hexyl-7-(2-methylphenyl)sulfanyl-3h-1-benzofuran-2-one Chemical compound CCCCCCC1C(=O)OC2=C1C=CC=C2SC1=CC=CC=C1C FXTGWXLGIKSPSU-UHFFFAOYSA-N 0.000 claims 1
- HILPECHHQVBCKS-UHFFFAOYSA-N 3-methyl-7-(2-methylphenoxy)-3h-1-benzofuran-2-one Chemical compound CC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C HILPECHHQVBCKS-UHFFFAOYSA-N 0.000 claims 1
- NLPHCSZMQLWUCY-UHFFFAOYSA-N 3-methyl-7-(2-methylphenyl)sulfanyl-3h-1-benzofuran-2-one Chemical compound CC1C(=O)OC2=C1C=CC=C2SC1=CC=CC=C1C NLPHCSZMQLWUCY-UHFFFAOYSA-N 0.000 claims 1
- HSBFFHKOCOGATF-UHFFFAOYSA-N 5-(2-chlorophenoxy)-3-methyl-3h-1-benzofuran-2-one Chemical compound C1=C2C(C)C(=O)OC2=CC=C1OC1=CC=CC=C1Cl HSBFFHKOCOGATF-UHFFFAOYSA-N 0.000 claims 1
- IQLWRKHSHUBPBE-UHFFFAOYSA-N 7-(2-chlorophenoxy)-3-propyl-3h-1-benzofuran-2-one Chemical compound CCCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1Cl IQLWRKHSHUBPBE-UHFFFAOYSA-N 0.000 claims 1
- SEFWGVFLRAYRDK-UHFFFAOYSA-N 7-(2-chlorophenoxy)-3h-1-benzofuran-2-one Chemical compound ClC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2 SEFWGVFLRAYRDK-UHFFFAOYSA-N 0.000 claims 1
- FUTOKHLICIFYDM-UHFFFAOYSA-N 7-(2-chlorophenyl)sulfanyl-3-methyl-3h-1-benzofuran-2-one Chemical compound CC1C(=O)OC2=C1C=CC=C2SC1=CC=CC=C1Cl FUTOKHLICIFYDM-UHFFFAOYSA-N 0.000 claims 1
- ZWQVJNPGRDIWPE-UHFFFAOYSA-N 7-(2-chlorophenyl)sulfanyl-3h-1-benzofuran-2-one Chemical compound ClC1=CC=CC=C1SC1=CC=CC2=C1OC(=O)C2 ZWQVJNPGRDIWPE-UHFFFAOYSA-N 0.000 claims 1
- JCGKGDMTJXXQHG-UHFFFAOYSA-N 7-(2-chlorophenyl)sulfinyl-3-methyl-3h-1-benzofuran-2-one Chemical compound CC1C(=O)OC2=C1C=CC=C2S(=O)C1=CC=CC=C1Cl JCGKGDMTJXXQHG-UHFFFAOYSA-N 0.000 claims 1
- GQONSSBYJRMZLB-UHFFFAOYSA-N 7-(2-fluorophenoxy)-3-methyl-3h-1-benzofuran-2-one Chemical compound CC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1F GQONSSBYJRMZLB-UHFFFAOYSA-N 0.000 claims 1
- RQTQKKGJWAKERY-UHFFFAOYSA-N 7-(2-fluorophenoxy)-3h-1-benzofuran-2-one Chemical compound FC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2 RQTQKKGJWAKERY-UHFFFAOYSA-N 0.000 claims 1
- AJZQLZQHAXSTML-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfanyl-3-methyl-3h-1-benzofuran-2-one Chemical compound CC1C(=O)OC2=C1C=CC=C2SC1=CC=CC=C1F AJZQLZQHAXSTML-UHFFFAOYSA-N 0.000 claims 1
- RCHBPLRQIYZIJA-UHFFFAOYSA-N 7-(2-hydroxyphenoxy)-3h-1-benzofuran-2-one Chemical compound OC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2 RCHBPLRQIYZIJA-UHFFFAOYSA-N 0.000 claims 1
- BFBNXNDJJOFDNY-UHFFFAOYSA-N 7-(2-methoxyphenoxy)-3h-1-benzofuran-2-one Chemical compound COC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)C2 BFBNXNDJJOFDNY-UHFFFAOYSA-N 0.000 claims 1
- PYIUSVHKXCEFLK-UHFFFAOYSA-N 7-(2-methylphenoxy)-3-pentyl-3h-1-benzofuran-2-one Chemical compound CCCCCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C PYIUSVHKXCEFLK-UHFFFAOYSA-N 0.000 claims 1
- IKGZIXMVLHIJMM-UHFFFAOYSA-N 7-(2-methylphenoxy)-3-propyl-3h-1-benzofuran-2-one Chemical compound CCCC1C(=O)OC2=C1C=CC=C2OC1=CC=CC=C1C IKGZIXMVLHIJMM-UHFFFAOYSA-N 0.000 claims 1
- KZMJQPJAZARMLS-UHFFFAOYSA-N 7-(2-methylphenyl)sulfanyl-3h-1-benzofuran-2-one Chemical compound CC1=CC=CC=C1SC1=CC=CC2=C1OC(=O)C2 KZMJQPJAZARMLS-UHFFFAOYSA-N 0.000 claims 1
- HJKBVJFQBOFGHA-UHFFFAOYSA-N 7-(4-chlorophenoxy)-3h-1-benzofuran-2-one Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC2=C1OC(=O)C2 HJKBVJFQBOFGHA-UHFFFAOYSA-N 0.000 claims 1
- YNCRVNAQKSZJNQ-UHFFFAOYSA-N 8-(2-chlorophenoxy)-3,4-dihydrochromen-2-one Chemical compound ClC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)CC2 YNCRVNAQKSZJNQ-UHFFFAOYSA-N 0.000 claims 1
- VJDHHNNHMZGPAU-UHFFFAOYSA-N 8-(2-methylphenoxy)-3,4-dihydrochromen-2-one Chemical compound CC1=CC=CC=C1OC1=CC=CC2=C1OC(=O)CC2 VJDHHNNHMZGPAU-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 88
- 230000000202 analgesic effect Effects 0.000 abstract description 5
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 283
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 171
- 239000000203 mixture Substances 0.000 description 150
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 149
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 123
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 104
- 239000000243 solution Substances 0.000 description 95
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 93
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
- 229960004132 diethyl ether Drugs 0.000 description 79
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
- 238000010438 heat treatment Methods 0.000 description 61
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 60
- 229960000583 acetic acid Drugs 0.000 description 59
- 239000000284 extract Substances 0.000 description 59
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- 235000011054 acetic acid Nutrition 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 51
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 44
- 239000000460 chlorine Substances 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- 235000011167 hydrochloric acid Nutrition 0.000 description 40
- 229960000443 hydrochloric acid Drugs 0.000 description 40
- 238000004458 analytical method Methods 0.000 description 38
- 238000001816 cooling Methods 0.000 description 38
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 31
- 101150041968 CDC13 gene Proteins 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- 229960003390 magnesium sulfate Drugs 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000007864 aqueous solution Substances 0.000 description 26
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 25
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- 229910052708 sodium Inorganic materials 0.000 description 24
- 239000011734 sodium Substances 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 229940022663 acetate Drugs 0.000 description 20
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000019260 propionic acid Nutrition 0.000 description 17
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 15
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 15
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229960001407 sodium bicarbonate Drugs 0.000 description 12
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000011591 potassium Substances 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 10
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 9
- 235000019445 benzyl alcohol Nutrition 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 229940095076 benzaldehyde Drugs 0.000 description 6
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 239000012286 potassium permanganate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NEMNPWINWMHUMR-UHFFFAOYSA-N rafoxanide Chemical compound OC1=C(I)C=C(I)C=C1C(=O)NC(C=C1Cl)=CC=C1OC1=CC=C(Cl)C=C1 NEMNPWINWMHUMR-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000012085 test solution Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
-
- 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
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- 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
- C07C45/70—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 with functional groups containing oxygen only in singly bound form
- C07C45/71—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 with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings 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
- C07C59/58—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8002790 | 1980-01-28 | ||
GB8002790 | 1980-01-28 | ||
GB8039308 | 1980-12-08 | ||
GB8039308 | 1980-12-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1195691A true CA1195691A (en) | 1985-10-22 |
Family
ID=26274313
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000368943A Expired CA1195691A (en) | 1980-01-28 | 1981-01-21 | Phenyl-alkanoic acid derivative and preparation thereof |
Country Status (10)
Country | Link |
---|---|
US (1) | US4367238A (en, 2012) |
EP (1) | EP0033614B1 (en, 2012) |
AR (1) | AR228586A1 (en, 2012) |
AT (1) | ATE7782T1 (en, 2012) |
AU (1) | AU537560B2 (en, 2012) |
CA (1) | CA1195691A (en, 2012) |
DE (1) | DE3162626D1 (en, 2012) |
DK (1) | DK34781A (en, 2012) |
ES (2) | ES508806A0 (en, 2012) |
GR (1) | GR73505B (en, 2012) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3110009A1 (de) * | 1981-03-11 | 1982-09-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue benzofuran-derivate, ihre herstellung und verwendung |
US4857455A (en) * | 1982-11-26 | 1989-08-15 | Syntex (U.S.A) Inc. | Method for the determination of peroxidase using fluorogenic substrates |
GB8328253D0 (en) * | 1983-10-21 | 1983-11-23 | Shell Int Research | Substituted azetidine derivatives |
US4911754A (en) * | 1987-07-16 | 1990-03-27 | American Cyanamid Company | Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds |
US5256686A (en) * | 1989-06-27 | 1993-10-26 | Ono Pharmaceutical Co., Ltd. | Phenylalkan(en)oic acid |
US6001877A (en) * | 1989-06-27 | 1999-12-14 | Ono Pharmaceutical Co., Ltd. | Phenylalkan(en)oic acid |
ES2163986B1 (es) * | 1999-07-13 | 2003-02-16 | Menarini Lab | Acidos-alfa-arilpropionicos y arilaceticos como inhibidores de la ciclooxigenasa-ii. |
DE60006289D1 (de) * | 2000-01-04 | 2003-12-04 | Korea Res Inst Chem Tech | Herstellungs verfahren von 2-phenylalkan-säure derivaten |
EP1366763A1 (en) * | 2002-05-28 | 2003-12-03 | Ciba SC Holding AG | Hydroxy diphenyl ether compounds as anti-inflammatory agents |
EP1481959A1 (de) * | 2003-05-22 | 2004-12-01 | DSM Fine Chemicals Austria Nfg GmbH & Co KG | Verfahren zur Herstellung von Lactonen und von aromatischen Hydroxycarbonsäuren |
GB201118876D0 (en) * | 2011-11-01 | 2011-12-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
EP3036222A2 (en) * | 2013-08-23 | 2016-06-29 | Virginia Commonwealth University | Ester nitrates derivatives of aromatic aldehydes with multiple pharmalogic properties to treat sickle cell disease |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2838522A (en) * | 1956-04-30 | 1958-06-10 | Dow Chemical Co | Phthalides |
SE363818B (en, 2012) * | 1968-08-15 | 1974-02-04 | Lilly Co Eli | |
US4120871A (en) * | 1975-05-06 | 1978-10-17 | Fisons Limited | 5-Organosulfonyl, 5-organosulfinyl or 5-haloalkanoyl-benzofuran-2-ones |
-
1981
- 1981-01-21 US US06/226,908 patent/US4367238A/en not_active Expired - Fee Related
- 1981-01-21 CA CA000368943A patent/CA1195691A/en not_active Expired
- 1981-01-22 AT AT81300283T patent/ATE7782T1/de active
- 1981-01-22 DE DE8181300283T patent/DE3162626D1/de not_active Expired
- 1981-01-22 EP EP81300283A patent/EP0033614B1/en not_active Expired
- 1981-01-26 DK DK34781A patent/DK34781A/da not_active Application Discontinuation
- 1981-01-27 GR GR63972A patent/GR73505B/el unknown
- 1981-01-28 AR AR284092A patent/AR228586A1/es active
- 1981-01-28 AU AU66687/81A patent/AU537560B2/en not_active Ceased
-
1982
- 1982-01-15 ES ES508806A patent/ES508806A0/es active Granted
- 1982-01-15 ES ES82508805A patent/ES508805A0/es active Granted
Also Published As
Publication number | Publication date |
---|---|
AU6668781A (en) | 1981-08-06 |
ES8300735A1 (es) | 1982-11-16 |
GR73505B (en, 2012) | 1984-03-06 |
EP0033614B1 (en) | 1984-06-06 |
ES508806A0 (es) | 1982-11-16 |
DK34781A (da) | 1981-07-29 |
EP0033614A1 (en) | 1981-08-12 |
AR228586A1 (es) | 1983-03-30 |
AU537560B2 (en) | 1984-06-28 |
ATE7782T1 (de) | 1984-06-15 |
ES8300734A1 (es) | 1982-11-16 |
US4367238A (en) | 1983-01-04 |
ES508805A0 (es) | 1982-11-16 |
DE3162626D1 (en) | 1984-07-12 |
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