NO813828L - Tetrasubstituerte benzenderivater - Google Patents
Tetrasubstituerte benzenderivaterInfo
- Publication number
- NO813828L NO813828L NO813828A NO813828A NO813828L NO 813828 L NO813828 L NO 813828L NO 813828 A NO813828 A NO 813828A NO 813828 A NO813828 A NO 813828A NO 813828 L NO813828 L NO 813828L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- methoxyphenyl
- formula
- dimethoxy
- benzamide
- Prior art date
Links
- 239000000446 fuel Substances 0.000 title 1
- -1 hydroxyimino Chemical group 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- WJYQYFNXURDIKC-UHFFFAOYSA-N 1-(4-ethoxy-2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound COC1=CC(OCC)=CC(O)=C1C(=O)CCC1=CC=C(OC)C=C1 WJYQYFNXURDIKC-UHFFFAOYSA-N 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- HJSRRIKDASQDOU-UHFFFAOYSA-N 4-ethoxy-2-hydroxy-6-methoxy-n-[(4-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC(OCC)=CC(O)=C1C(=O)NCC1=CC=C(OC)C=C1 HJSRRIKDASQDOU-UHFFFAOYSA-N 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003051 glycosyloxy group Chemical group 0.000 claims description 8
- PBFRFGFAEAGUGA-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxy-n-[(4-methoxyphenyl)methyl]benzamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=C(O)C=C(OC)C=C1OC PBFRFGFAEAGUGA-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
- BAQNGLWGRXPMJZ-UHFFFAOYSA-N 2-[5-ethoxy-3-methoxy-2-[3-(4-methoxyphenyl)propanoyl]phenyl]acetic acid Chemical compound COC1=CC(OCC)=CC(CC(O)=O)=C1C(=O)CCC1=CC=C(OC)C=C1 BAQNGLWGRXPMJZ-UHFFFAOYSA-N 0.000 claims description 3
- RCANHDAHXKBJDR-UHFFFAOYSA-N 2-hydroxy-6-methoxy-n-[(4-methoxyphenyl)methyl]-4-propoxybenzamide Chemical compound COC1=CC(OCCC)=CC(O)=C1C(=O)NCC1=CC=C(OC)C=C1 RCANHDAHXKBJDR-UHFFFAOYSA-N 0.000 claims description 3
- YADJFRGSGWGMNH-UHFFFAOYSA-N [chloro(phenylmethoxy)phosphoryl]oxymethylbenzene Chemical compound C=1C=CC=CC=1COP(=O)(Cl)OCC1=CC=CC=C1 YADJFRGSGWGMNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002443 hydroxylamines Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- MFAYWKMQLIAVOW-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(5-methyloxolan-2-yl)propan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCC1OC(C)CC1 MFAYWKMQLIAVOW-UHFFFAOYSA-N 0.000 claims description 2
- JILWXSFQNFORLF-UHFFFAOYSA-N 1-(2-hydroxy-6-methoxy-4-methylsulfanylphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=CC(OC)=CC=C1CCC(=O)C1=C(O)C=C(SC)C=C1OC JILWXSFQNFORLF-UHFFFAOYSA-N 0.000 claims description 2
- WJUHQEPLDRULKN-UHFFFAOYSA-N 1-(4-ethoxy-2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)propane-1-thione Chemical compound C(C)OC1=CC(=C(C(=C1)OC)C(CCC1=CC=C(C=C1)OC)=S)O WJUHQEPLDRULKN-UHFFFAOYSA-N 0.000 claims description 2
- OKTXENOOXBXOOC-UHFFFAOYSA-N 2-[3,5-dimethoxy-2-[(4-methoxyphenyl)methylcarbamoyl]phenyl]ethyl hydrogen carbonate Chemical compound COC1=CC=C(C=C1)CNC(=O)C2=C(C=C(C=C2OC)OC)CCOC(=O)O OKTXENOOXBXOOC-UHFFFAOYSA-N 0.000 claims description 2
- MKRNUSBFCAQFSE-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxy-n-[(4-methylsulfanylphenyl)methyl]benzamide Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)NCC1=CC=C(SC)C=C1 MKRNUSBFCAQFSE-UHFFFAOYSA-N 0.000 claims description 2
- RLDUKHIHNRMEMF-UHFFFAOYSA-N 4-ethoxy-2-hydroxy-6-methoxy-N-[(4-methoxyphenyl)methyl]benzenecarbothioamide Chemical compound C(C)OC1=CC(=C(C(=S)NCC2=CC=C(C=C2)OC)C(=C1)OC)O RLDUKHIHNRMEMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- KKOJMPPOKRFWPO-UHFFFAOYSA-N [5-ethoxy-3-methoxy-2-[(4-methoxyphenyl)methylcarbamoyl]phenyl] dihydrogen phosphate Chemical compound OP(=O)(O)OC1=CC(OCC)=CC(OC)=C1C(=O)NCC1=CC=C(OC)C=C1 KKOJMPPOKRFWPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- HSXHGGPYKJEZGQ-UHFFFAOYSA-N 2-[N-hydroxy-C-[2-(4-methoxyphenyl)ethyl]carbonimidoyl]-3,5-dimethoxyphenol Chemical compound OC1=C(C(=CC(=C1)OC)OC)C(CCC1=CC=C(C=C1)OC)=NO HSXHGGPYKJEZGQ-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-M octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 claims 2
- KMINZJBFUHKSFJ-UHFFFAOYSA-N 1-(2-ethoxy-6-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound CCOC1=CC(OC)=CC(O)=C1C(=O)CCC1=CC=C(OC)C=C1 KMINZJBFUHKSFJ-UHFFFAOYSA-N 0.000 claims 1
- HUDRDIQVKUPHHC-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylphenyl)propan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCC1=CC=C(C)C=C1 HUDRDIQVKUPHHC-UHFFFAOYSA-N 0.000 claims 1
- VJEUOFVJRFFKJX-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylsulfanylphenyl)propan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCC1=CC=C(SC)C=C1 VJEUOFVJRFFKJX-UHFFFAOYSA-N 0.000 claims 1
- LDLORMSLOWXLNR-UHFFFAOYSA-N 1-(2-hydroxy-6-methoxy-4-propan-2-yloxyphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=CC(OC)=CC=C1CCC(=O)C1=C(O)C=C(OC(C)C)C=C1OC LDLORMSLOWXLNR-UHFFFAOYSA-N 0.000 claims 1
- VYCIWQJCVPFLML-UHFFFAOYSA-N 1-(2-hydroxy-6-methoxy-4-propoxyphenyl)-3-(4-methoxyphenyl)propan-1-one Chemical compound COC1=CC(OCCC)=CC(O)=C1C(=O)CCC1=CC=C(OC)C=C1 VYCIWQJCVPFLML-UHFFFAOYSA-N 0.000 claims 1
- SDYIZAANGZBOSO-UHFFFAOYSA-N 2,3-dimethoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1OC SDYIZAANGZBOSO-UHFFFAOYSA-N 0.000 claims 1
- WEWFRBFPXRXHOL-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxy-n-[(3-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC=CC(CNC(=O)C=2C(=CC(OC)=CC=2O)OC)=C1 WEWFRBFPXRXHOL-UHFFFAOYSA-N 0.000 claims 1
- DWQHSPXIZVVYGD-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxy-n-[(4-methylphenyl)methyl]benzamide Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)NCC1=CC=C(C)C=C1 DWQHSPXIZVVYGD-UHFFFAOYSA-N 0.000 claims 1
- BBBFJGMZWNSBDG-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxy-n-methylbenzamide Chemical compound CNC(=O)C1=C(O)C=C(OC)C=C1OC BBBFJGMZWNSBDG-UHFFFAOYSA-N 0.000 claims 1
- HMOGNLACHPYKOO-UHFFFAOYSA-N 2-hydroxy-N-[(3-hydroxy-4-methoxyphenyl)methyl]-4,6-dimethoxybenzamide Chemical compound OC1=C(C(=O)NCC2=CC(=C(C=C2)OC)O)C(=CC(=C1)OC)OC HMOGNLACHPYKOO-UHFFFAOYSA-N 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- VZGPJZMPOYMGMB-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-1-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCC1=CC=C(OCO2)C2=C1 VZGPJZMPOYMGMB-UHFFFAOYSA-N 0.000 claims 1
- LIWHIYLVGPLVKR-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCC1=CC=C(Cl)C=C1 LIWHIYLVGPLVKR-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 claims 1
- UOJQBPOLHKFCGL-UHFFFAOYSA-N [5-ethoxy-3-methoxy-2-[3-(4-methoxyphenyl)propanoyl]phenyl] dihydrogen phosphate Chemical compound OP(=O)(O)OC1=CC(OCC)=CC(OC)=C1C(=O)CCC1=CC=C(OC)C=C1 UOJQBPOLHKFCGL-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 claims 1
- KYVCXTDNSZRIPK-UHFFFAOYSA-N n-benzyl-2-hydroxy-4,6-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)NCC1=CC=CC=C1 KYVCXTDNSZRIPK-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 39
- 238000002844 melting Methods 0.000 description 38
- 230000008018 melting Effects 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 230000000840 anti-viral effect Effects 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- TXWSSNZBPALBMO-UHFFFAOYSA-N 2,4-dimethoxy-6-phenylmethoxybenzoic acid Chemical compound COC1=CC(OC)=C(C(O)=O)C(OCC=2C=CC=CC=2)=C1 TXWSSNZBPALBMO-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 3
- ZWJIJEOIENYKPK-UHFFFAOYSA-N 1-phenyl-3-(2-propoxyphenyl)prop-2-en-1-one Chemical compound CCCOC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 ZWJIJEOIENYKPK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- 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
- 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
-
- 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
- C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/42—Y being a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
- C07C325/02—Thioketones; Oxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
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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
- C07C45/68—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
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- 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
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
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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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- C—CHEMISTRY; METALLURGY
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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
- C07D317/58—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (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 (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8036223 | 1980-11-12 | ||
GB8130001 | 1981-10-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO813828L true NO813828L (no) | 1982-05-13 |
Family
ID=26277482
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO813828A NO813828L (no) | 1980-11-12 | 1981-11-11 | Tetrasubstituerte benzenderivater |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP0051819B1 (xx) |
AU (1) | AU543311B2 (xx) |
BR (1) | BR8107320A (xx) |
CA (1) | CA1206964A (xx) |
CS (1) | CS270551B2 (xx) |
CU (1) | CU21424A (xx) |
DE (1) | DE3168951D1 (xx) |
DK (1) | DK465581A (xx) |
ES (3) | ES516194A0 (xx) |
FI (1) | FI813543L (xx) |
GR (1) | GR81318B (xx) |
HU (1) | HU189991B (xx) |
IL (1) | IL64266A (xx) |
MC (1) | MC1417A1 (xx) |
NO (1) | NO813828L (xx) |
NZ (1) | NZ198879A (xx) |
PT (1) | PT73973B (xx) |
YU (1) | YU266481A (xx) |
ZW (1) | ZW26281A1 (xx) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2094786B (en) * | 1981-03-04 | 1985-09-11 | Ici Plc | Herbicidal and fungicidal amide derivatives |
CH653670A5 (de) * | 1983-03-03 | 1986-01-15 | Hoffmann La Roche | Benzamid-derivate. |
US5098613A (en) * | 1987-01-12 | 1992-03-24 | Eli Lilly And Company | Anti-inflammatory agents |
US4945099A (en) * | 1987-01-12 | 1990-07-31 | Eli Lilly And Company | Anti-inflammatory agents |
US5294613A (en) * | 1987-01-12 | 1994-03-15 | Eli Lilly And Company | Method of treating endotoxic shock in mammals |
CA1315279C (en) * | 1987-01-12 | 1993-03-30 | Nancy Grace Bollinger | Anti-inflammatory agents |
US5045239A (en) * | 1987-07-23 | 1991-09-03 | Nippon Oil And Fats Co., Ltd. | Non-linear optical material |
JPH01190663A (ja) * | 1988-01-22 | 1989-07-31 | Terumo Corp | システアミン誘導体及びこれを含有する抗リウマチ剤 |
DE4201942A1 (de) * | 1991-02-26 | 1992-09-24 | Plantamed Arzneimittel Gmbh | Phenonverbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
IL111613A0 (en) * | 1993-11-12 | 1995-01-24 | Rhone Poulenc Rorer Ltd | Substituted phenyl compounds, their preparation and pharmaceutical compositions containing them |
US5801195A (en) * | 1994-12-30 | 1998-09-01 | Celgene Corporation | Immunotherapeutic aryl amides |
IL118657A0 (en) * | 1996-06-14 | 1996-10-16 | Arad Dorit | Inhibitors for picornavirus proteases |
IL122591A0 (en) | 1997-12-14 | 1998-06-15 | Arad Dorit | Pharmaceutical compositions comprising cystein protease inhibitors |
EP1175425A2 (en) | 1999-01-21 | 2002-01-30 | The Board Of Regents, The University Of Texas System | Inhibitors of intestinal apical membrane na/phosphate co-transportation |
US6653309B1 (en) | 1999-04-26 | 2003-11-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme technical field of the invention |
CN103755732B (zh) | 2014-01-23 | 2016-06-08 | 中山大学 | 邻苯基查尔酮类化合物及其制备方法和应用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3087821A (en) * | 1961-11-28 | 1963-04-30 | Robert M Horowitz | Dihydrochalcone derivatives and their use as sweetening agents |
JPS51146432A (en) * | 1975-06-12 | 1976-12-16 | Microbial Chem Res Found | Process for preparation of benzanilide derivatives having therapeutic action to immunological disease |
US4219569A (en) * | 1978-10-10 | 1980-08-26 | The Upjohn Company | Process for treating inflammation |
NZ192641A (en) * | 1979-01-26 | 1984-10-19 | Hoffmann La Roche | Substituted acetophenones and pharmaceutical compositions |
DD146295A1 (de) * | 1979-10-01 | 1981-02-04 | Konrad Schwabe | Verfahren zur herstellung von salizylanilid-o-glykosiden |
-
1981
- 1981-10-20 CA CA000388364A patent/CA1206964A/en not_active Expired
- 1981-10-21 DK DK465581A patent/DK465581A/da not_active Application Discontinuation
- 1981-10-29 EP EP81109200A patent/EP0051819B1/de not_active Expired
- 1981-10-29 DE DE8181109200T patent/DE3168951D1/de not_active Expired
- 1981-10-30 ZW ZW262/81A patent/ZW26281A1/xx unknown
- 1981-11-05 NZ NZ198879A patent/NZ198879A/en unknown
- 1981-11-09 HU HU813337A patent/HU189991B/hu unknown
- 1981-11-09 AU AU77305/81A patent/AU543311B2/en not_active Ceased
- 1981-11-10 CU CU8135555A patent/CU21424A/es unknown
- 1981-11-10 GR GR66485A patent/GR81318B/el unknown
- 1981-11-10 MC MC811561A patent/MC1417A1/xx unknown
- 1981-11-10 CS CS818260A patent/CS270551B2/cs unknown
- 1981-11-10 FI FI813543A patent/FI813543L/fi not_active Application Discontinuation
- 1981-11-11 YU YU02664/81A patent/YU266481A/xx unknown
- 1981-11-11 IL IL64266A patent/IL64266A/xx unknown
- 1981-11-11 BR BR8107320A patent/BR8107320A/pt unknown
- 1981-11-11 PT PT73973A patent/PT73973B/pt unknown
- 1981-11-11 NO NO813828A patent/NO813828L/no unknown
-
1982
- 1982-10-04 ES ES516194A patent/ES516194A0/es active Granted
- 1982-10-04 ES ES516198A patent/ES516198A0/es active Granted
- 1982-10-04 ES ES516193A patent/ES8308839A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES516193A0 (es) | 1983-10-01 |
MC1417A1 (fr) | 1982-10-18 |
ZW26281A1 (en) | 1982-06-02 |
YU266481A (en) | 1983-12-31 |
ES8308841A1 (es) | 1983-10-01 |
DE3168951D1 (en) | 1985-03-28 |
CU21424A (es) | 1983-05-05 |
CS826081A2 (en) | 1989-09-12 |
EP0051819B1 (de) | 1985-02-13 |
GR81318B (xx) | 1984-12-11 |
HU189991B (en) | 1986-08-28 |
FI813543L (fi) | 1982-05-13 |
PT73973A (en) | 1981-12-01 |
ES516198A0 (es) | 1983-10-01 |
AU7730581A (en) | 1982-05-20 |
BR8107320A (pt) | 1982-08-03 |
ES8308839A1 (es) | 1983-10-01 |
EP0051819A2 (de) | 1982-05-19 |
CS270551B2 (en) | 1990-07-12 |
NZ198879A (en) | 1985-02-28 |
PT73973B (en) | 1983-11-23 |
EP0051819A3 (en) | 1982-08-11 |
CA1206964A (en) | 1986-07-02 |
ES8308840A1 (es) | 1983-10-01 |
ES516194A0 (es) | 1983-10-01 |
DK465581A (da) | 1982-05-13 |
AU543311B2 (en) | 1985-04-18 |
IL64266A (en) | 1985-12-31 |
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