IE48676B1 - Phenyl-alkanoic acid derivatives,the preparation thereof and pharmaceutical compositions containing them - Google Patents
Phenyl-alkanoic acid derivatives,the preparation thereof and pharmaceutical compositions containing themInfo
- Publication number
- IE48676B1 IE48676B1 IE1490/79A IE149079A IE48676B1 IE 48676 B1 IE48676 B1 IE 48676B1 IE 1490/79 A IE1490/79 A IE 1490/79A IE 149079 A IE149079 A IE 149079A IE 48676 B1 IE48676 B1 IE 48676B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- give
- general formula
- phenyl
- mixture
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
- 239000002253 acid Substances 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title abstract description 122
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- -1 oxy, thio, sulfinyl Chemical group 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 40
- 230000002829 reductive effect Effects 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 241000282414 Homo sapiens Species 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 230000027950 fever generation Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000004371 toothache Diseases 0.000 claims 2
- 206010019233 Headaches Diseases 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 176
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 153
- 239000000203 mixture Substances 0.000 description 140
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 120
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 98
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 41
- 239000000706 filtrate Substances 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 29
- 238000010438 heat treatment Methods 0.000 description 29
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
- 235000019341 magnesium sulphate Nutrition 0.000 description 29
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 23
- 239000013078 crystal Substances 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 20
- 239000000284 extract Substances 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 235000019270 ammonium chloride Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 229960004643 cupric oxide Drugs 0.000 description 12
- 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 11
- 239000007868 Raney catalyst Substances 0.000 description 11
- 229910000564 Raney nickel Inorganic materials 0.000 description 11
- XJDQUPFWVIUWNZ-UHFFFAOYSA-N o-ethyl propanethioate Chemical compound CCOC(=S)CC XJDQUPFWVIUWNZ-UHFFFAOYSA-N 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 159000000000 sodium salts Chemical class 0.000 description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-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
- 238000004458 analytical method Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QKFCFMRCEYUIDT-UHFFFAOYSA-N ethyl 2-(3-chloro-2-nitrophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(Cl)=C1[N+]([O-])=O QKFCFMRCEYUIDT-UHFFFAOYSA-N 0.000 description 8
- 230000001376 precipitating effect Effects 0.000 description 8
- OCXGHAZGBIVTHJ-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenoxy)-2-nitrophenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1[N+]([O-])=O OCXGHAZGBIVTHJ-UHFFFAOYSA-N 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- OESQGNRWHZBZGF-UHFFFAOYSA-N 7-(2-chlorophenoxy)-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC=C1OC1=CC=CC2=C1NC(=O)C2 OESQGNRWHZBZGF-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000001754 anti-pyretic effect Effects 0.000 description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- MLNRZZPDQFBQSY-UHFFFAOYSA-N 2-[3-(2-fluorophenoxy)-2-nitrophenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)F)=C1[N+]([O-])=O MLNRZZPDQFBQSY-UHFFFAOYSA-N 0.000 description 5
- 241001669680 Dormitator maculatus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- XZCLACZNHONQFB-UHFFFAOYSA-N 7-(2-chlorophenoxy)-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound CSC1C(=O)NC2=C1C=CC=C2OC1=CC=CC=C1Cl XZCLACZNHONQFB-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 206010015150 Erythema Diseases 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 231100000321 erythema Toxicity 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- OYPNVQIVICSZCO-UHFFFAOYSA-M sodium;2-[2-amino-3-(2-chlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=CC=CC=C1Cl OYPNVQIVICSZCO-UHFFFAOYSA-M 0.000 description 4
- 208000011580 syndromic disease Diseases 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000002221 antipyretic Substances 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000004590 computer program Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- JQJLTEVTDTWBQT-UHFFFAOYSA-N ethyl 2-[3-(2-fluorophenoxy)-2-nitrophenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)F)=C1[N+]([O-])=O JQJLTEVTDTWBQT-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- TZIYHCRTWKWCHK-UHFFFAOYSA-N 1-(bromomethyl)-3-(2-chlorophenoxy)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(CBr)C=CC=C1OC1=CC=CC=C1Cl TZIYHCRTWKWCHK-UHFFFAOYSA-N 0.000 description 2
- KSDCPEXSRBLIRA-UHFFFAOYSA-N 2-(2-chlorophenoxy)aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1Cl KSDCPEXSRBLIRA-UHFFFAOYSA-N 0.000 description 2
- HIVNAQYUIBLEHZ-UHFFFAOYSA-N 2-(2-methoxyphenoxy)aniline Chemical compound COC1=CC=CC=C1OC1=CC=CC=C1N HIVNAQYUIBLEHZ-UHFFFAOYSA-N 0.000 description 2
- KITPQBRWJSNMQX-UHFFFAOYSA-N 2-(2-nitro-3-phenoxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1[N+]([O-])=O KITPQBRWJSNMQX-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CMBDOKTXQBCUMD-UHFFFAOYSA-N 2-[2-amino-3-(2,3-dichlorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1OC1=CC=CC(Cl)=C1Cl CMBDOKTXQBCUMD-UHFFFAOYSA-N 0.000 description 2
- DIZFBXXHQNXOPF-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1OC1=CC=C(Cl)C=C1Cl DIZFBXXHQNXOPF-UHFFFAOYSA-N 0.000 description 2
- XJOPWORZQVFHIH-UHFFFAOYSA-N 2-[2-amino-3-(2-methylphenoxy)phenyl]acetic acid Chemical compound CC1=CC=CC=C1OC1=CC=CC(CC(O)=O)=C1N XJOPWORZQVFHIH-UHFFFAOYSA-N 0.000 description 2
- YEBMCOHYKLBMPO-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-(2-chlorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1OC1=CC=CC=C1Cl YEBMCOHYKLBMPO-UHFFFAOYSA-N 0.000 description 2
- IGZFWAOWWIRLHA-UHFFFAOYSA-N 2-[3-(2,4-dichlorophenoxy)-2-nitrophenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1[N+]([O-])=O IGZFWAOWWIRLHA-UHFFFAOYSA-N 0.000 description 2
- FQWLHGGNAZWACC-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)-2-nitrophenyl]acetonitrile Chemical compound [O-][N+](=O)C1=C(CC#N)C=CC=C1OC1=CC=CC=C1Cl FQWLHGGNAZWACC-UHFFFAOYSA-N 0.000 description 2
- IHTQCRNCVIZSEX-UHFFFAOYSA-N 2-[3-(2-fluorophenoxy)-2-nitrophenyl]-1-(4-hydroxypiperidin-1-yl)ethanone Chemical compound C1CC(O)CCN1C(=O)CC1=CC=CC(OC=2C(=CC=CC=2)F)=C1[N+]([O-])=O IHTQCRNCVIZSEX-UHFFFAOYSA-N 0.000 description 2
- RYTNLIUXOGYZHW-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-nitrophenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1[N+]([O-])=O RYTNLIUXOGYZHW-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- DLRNAMNCNBXPCI-UHFFFAOYSA-N 3-(2-chlorophenoxy)-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1[N+]([O-])=O DLRNAMNCNBXPCI-UHFFFAOYSA-N 0.000 description 2
- LELYKEJLFARUHO-UHFFFAOYSA-N 5-(2-chlorophenoxy)-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC=C1OC1=CC=C(NC(=O)C2)C2=C1 LELYKEJLFARUHO-UHFFFAOYSA-N 0.000 description 2
- YJDDOZAKOXSNDC-UHFFFAOYSA-N 5-(4-chlorophenoxy)-1,3-dihydroindol-2-one Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(NC(=O)C2)C2=C1 YJDDOZAKOXSNDC-UHFFFAOYSA-N 0.000 description 2
- RPFXSFOTGUMSDP-UHFFFAOYSA-N 5-chloro-7-(2-fluorophenoxy)-1,3-dihydroindol-2-one Chemical compound FC1=CC=CC=C1OC1=CC(Cl)=CC2=C1NC(=O)C2 RPFXSFOTGUMSDP-UHFFFAOYSA-N 0.000 description 2
- SNDNITDFJZJLCT-UHFFFAOYSA-N 5-phenoxy-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1OC1=CC=CC=C1 SNDNITDFJZJLCT-UHFFFAOYSA-N 0.000 description 2
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- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- CMUAEPZITCKQGD-UHFFFAOYSA-N ethyl 2-[2-amino-3-(2-methylphenoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)C)=C1N CMUAEPZITCKQGD-UHFFFAOYSA-N 0.000 description 1
- APEVNCHLHYBPRA-UHFFFAOYSA-N ethyl 2-[2-amino-3-(3,4-dichlorophenoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C=C(Cl)C(Cl)=CC=2)=C1N APEVNCHLHYBPRA-UHFFFAOYSA-N 0.000 description 1
- LNHGSVKERUIQGJ-UHFFFAOYSA-N ethyl 2-[2-amino-3-(3-chlorophenoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C=C(Cl)C=CC=2)=C1N LNHGSVKERUIQGJ-UHFFFAOYSA-N 0.000 description 1
- NGVQCZCWMFVUEA-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenoxy)-2-(dimethylamino)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1N(C)C NGVQCZCWMFVUEA-UHFFFAOYSA-N 0.000 description 1
- JCUFRNSLLXFJPS-UHFFFAOYSA-N ethyl 2-[3-(3,4-dichlorophenoxy)-2-nitrophenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C=C(Cl)C(Cl)=CC=2)=C1[N+]([O-])=O JCUFRNSLLXFJPS-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- PJQBFQAGKGMKQW-UHFFFAOYSA-N ethyl 3-(2-chlorophenoxy)-2-nitrobenzoate Chemical compound CCOC(=O)C1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1[N+]([O-])=O PJQBFQAGKGMKQW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical class C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 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 1
- 210000000664 rectum Anatomy 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 125000003607 serino group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- HDOAEFSMMMUKGP-UHFFFAOYSA-M sodium;2-(2-amino-3-chloro-6-phenoxyphenyl)acetate Chemical compound [Na+].NC1=C(Cl)C=CC(OC=2C=CC=CC=2)=C1CC([O-])=O HDOAEFSMMMUKGP-UHFFFAOYSA-M 0.000 description 1
- FRVVSNPMKCPGPH-UHFFFAOYSA-M sodium;2-(2-amino-3-phenoxyphenyl)acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=CC=CC=C1 FRVVSNPMKCPGPH-UHFFFAOYSA-M 0.000 description 1
- ILTCDXDVQVIZGG-UHFFFAOYSA-M sodium;2-(2-amino-5-phenoxyphenyl)acetate Chemical compound [Na+].C1=C(CC([O-])=O)C(N)=CC=C1OC1=CC=CC=C1 ILTCDXDVQVIZGG-UHFFFAOYSA-M 0.000 description 1
- SNSJXVJIOOVGJZ-UHFFFAOYSA-M sodium;2-[2-amino-3-(2,4-dichlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=CC=C(Cl)C=C1Cl SNSJXVJIOOVGJZ-UHFFFAOYSA-M 0.000 description 1
- RNZODVOBWSVNPZ-UHFFFAOYSA-M sodium;2-[2-amino-3-(2,6-dichlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=C(Cl)C=CC=C1Cl RNZODVOBWSVNPZ-UHFFFAOYSA-M 0.000 description 1
- GHXLFJONRZDLOP-UHFFFAOYSA-M sodium;2-[2-amino-3-(2-chlorophenoxy)phenyl]propanoate Chemical compound [Na+].[O-]C(=O)C(C)C1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1N GHXLFJONRZDLOP-UHFFFAOYSA-M 0.000 description 1
- OMGWTQJQSOEVIB-UHFFFAOYSA-M sodium;2-[2-amino-3-(2-methoxyphenoxy)phenyl]acetate Chemical compound [Na+].COC1=CC=CC=C1OC1=CC=CC(CC([O-])=O)=C1N OMGWTQJQSOEVIB-UHFFFAOYSA-M 0.000 description 1
- KPPLGYVMYPXYMB-UHFFFAOYSA-M sodium;2-[2-amino-3-(2-methylphenoxy)phenyl]acetate Chemical compound [Na+].CC1=CC=CC=C1OC1=CC=CC(CC([O-])=O)=C1N KPPLGYVMYPXYMB-UHFFFAOYSA-M 0.000 description 1
- KJVJLCAUQZUJPE-UHFFFAOYSA-M sodium;2-[2-amino-3-(3,4,5-trimethoxyphenoxy)phenyl]acetate Chemical compound [Na+].COC1=C(OC)C(OC)=CC(OC=2C(=C(CC([O-])=O)C=CC=2)N)=C1 KJVJLCAUQZUJPE-UHFFFAOYSA-M 0.000 description 1
- TXYBGCMFDLCPQT-UHFFFAOYSA-M sodium;2-[2-amino-3-(3,4-dichlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=CC=C(Cl)C(Cl)=C1 TXYBGCMFDLCPQT-UHFFFAOYSA-M 0.000 description 1
- ARVWPIAPCFYOLX-UHFFFAOYSA-M sodium;2-[2-amino-3-(3,5-dichlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ARVWPIAPCFYOLX-UHFFFAOYSA-M 0.000 description 1
- RJGSCLQKLVGNQJ-UHFFFAOYSA-M sodium;2-[2-amino-3-(3-chlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1OC1=CC=CC(Cl)=C1 RJGSCLQKLVGNQJ-UHFFFAOYSA-M 0.000 description 1
- GRDRVEWJLKABQA-UHFFFAOYSA-M sodium;2-[2-amino-5-(2-chlorophenoxy)phenyl]acetate Chemical compound [Na+].C1=C(CC([O-])=O)C(N)=CC=C1OC1=CC=CC=C1Cl GRDRVEWJLKABQA-UHFFFAOYSA-M 0.000 description 1
- JFKQXASPNRTURI-UHFFFAOYSA-M sodium;2-[2-amino-5-chloro-3-(2-chlorophenoxy)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=C(Cl)C=C1OC1=CC=CC=C1Cl JFKQXASPNRTURI-UHFFFAOYSA-M 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Toxicology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7832609 | 1978-08-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE791490L IE791490L (en) | 1980-02-08 |
| IE48676B1 true IE48676B1 (en) | 1985-04-17 |
Family
ID=10498927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1490/79A IE48676B1 (en) | 1978-08-08 | 1979-08-08 | Phenyl-alkanoic acid derivatives,the preparation thereof and pharmaceutical compositions containing them |
Country Status (15)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4333951A (en) * | 1977-11-15 | 1982-06-08 | A. H. Robins Company, Inc. | 2-Amino-6-biphenylacetic acids |
| US4477556A (en) * | 1982-08-18 | 1984-10-16 | E. I. Du Pont De Nemours And Company | Acidic o-nitroaromatics as photoinhibitors of polymerization in positive working films |
| JPS61206716A (ja) * | 1985-03-12 | 1986-09-13 | Sato Hisao | 搬送ロ−ル |
| US4911754A (en) * | 1987-07-16 | 1990-03-27 | American Cyanamid Company | Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds |
| ES2058024B1 (es) * | 1992-11-10 | 1995-05-01 | Menarini Lab | Nuevo derivado arilpropionico, procedimiento de fabricacion del mismo y su utilizacion como analgesico. |
| EP0702678A1 (en) * | 1993-06-07 | 1996-03-27 | Zeneca Limited | Aniline derivatives |
| ATE448194T1 (de) | 2000-08-29 | 2009-11-15 | Biocon Ltd | Verwendung einer pharmazeutischen zusammensetzung mit einem para-aminophenylessigsäurederivat für die behandlung von entzündlichen erkrankungen des magen-darmtrakts |
| US7186745B2 (en) | 2001-03-06 | 2007-03-06 | Astrazeneca Ab | Indolone derivatives having vascular damaging activity |
| US8048924B2 (en) | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
| HUE028158T2 (en) | 2004-07-07 | 2016-12-28 | Biocon Ltd | Synthesis of bound immunoregulatory compounds |
| CA3012133A1 (en) | 2016-02-09 | 2017-08-17 | Inventisbio Inc. | Inhibitor of indoleamine-2,3-dioxygenase (ido) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1072998B (de) * | 1960-01-14 | Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brüning, Frankfurt/M | Verfahren zur Herstellung von substituierten Diphenyläthern | |
| FR1657M (fr) * | 1961-01-14 | 1963-02-15 | Merck Ag E | 5-aleoxy-oxindoles |
| FR1516142A (fr) * | 1967-01-24 | 1968-03-08 | Rhone Poulenc Sa | Nouveau procédé de préparation de dérivés de la phénothiazine |
| US3981905A (en) * | 1970-03-16 | 1976-09-21 | Boots Pure Drug Company Limited | 2-(Substituted phenyl) propionic acids |
| JPS512358Y2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-05-08 | 1976-01-23 | ||
| BE795159A (fr) * | 1972-02-08 | 1973-08-08 | Thomae Gmbh Dr K | Nouveaux acides butendiques, sels et derives de ces acides et procedes pour les preparer |
| CH569013A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-07-21 | 1975-11-14 | Hoffmann La Roche | |
| US4006161A (en) * | 1973-12-26 | 1977-02-01 | Eli Lilly And Company | Thio-substituted 2-oxo-indolines |
| JPS511442A (ja) * | 1974-06-19 | 1976-01-08 | Fujisawa Pharmaceutical Co | Fuenokishifuenirusakusanruino seizoho |
| JPS5487136A (en) * | 1977-12-23 | 1979-07-11 | Fujitsu Ltd | Coupler between channels |
-
1979
- 1979-07-28 GR GR59719A patent/GR68102B/el unknown
- 1979-08-01 AU AU49461/79A patent/AU526877B2/en not_active Ceased
- 1979-08-07 AT AT79301600T patent/ATE5188T1/de active
- 1979-08-07 SU SU792802251A patent/SU1199197A3/ru active
- 1979-08-07 EP EP79301600A patent/EP0008226B1/en not_active Expired
- 1979-08-07 DE DE7979301600T patent/DE2966364D1/de not_active Expired
- 1979-08-07 DK DK331679A patent/DK331679A/da not_active Application Discontinuation
- 1979-08-07 CA CA333,296A patent/CA1127160A/en not_active Expired
- 1979-08-08 HU HU79FU371A patent/HU184114B/hu unknown
- 1979-08-08 JP JP10173879A patent/JPS5551041A/ja active Granted
- 1979-08-08 IE IE1490/79A patent/IE48676B1/en unknown
- 1979-08-08 ES ES483252A patent/ES483252A1/es not_active Expired
- 1979-08-08 AR AR277639A patent/AR228019A1/es active
- 1979-08-08 PH PH22880A patent/PH22340A/en unknown
-
1980
- 1980-06-30 ES ES492954A patent/ES492954A0/es active Granted
- 1980-06-30 ES ES492955A patent/ES492955A0/es active Granted
-
1981
- 1981-01-26 AR AR284073A patent/AR226446A1/es active
- 1981-03-13 SU SU813256798A patent/SU1053743A3/ru active
- 1981-08-10 US US06/291,498 patent/US4472433A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES483252A1 (es) | 1980-09-01 |
| ES8106482A1 (es) | 1981-07-01 |
| DK331679A (da) | 1980-02-09 |
| HU184114B (en) | 1984-07-30 |
| ES8105690A1 (es) | 1981-06-16 |
| ES492955A0 (es) | 1981-07-01 |
| SU1053743A3 (ru) | 1983-11-07 |
| US4472433A (en) | 1984-09-18 |
| JPS6256861B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-11-27 |
| AU526877B2 (en) | 1983-02-03 |
| EP0008226B1 (en) | 1983-11-02 |
| EP0008226A2 (en) | 1980-02-20 |
| AR228019A1 (es) | 1983-01-14 |
| IE791490L (en) | 1980-02-08 |
| EP0008226A3 (en) | 1980-03-05 |
| AR226446A1 (es) | 1982-07-15 |
| AU4946179A (en) | 1981-02-05 |
| ATE5188T1 (de) | 1983-11-15 |
| SU1199197A3 (ru) | 1985-12-15 |
| GR68102B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-10-30 |
| PH22340A (en) | 1988-08-12 |
| JPS5551041A (en) | 1980-04-14 |
| ES492954A0 (es) | 1981-06-16 |
| DE2966364D1 (en) | 1983-12-08 |
| CA1127160A (en) | 1982-07-06 |
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