HU184114B - Process for preparing phenyl-alkanecarboxylic acid derivatives - Google Patents
Process for preparing phenyl-alkanecarboxylic acid derivatives Download PDFInfo
- Publication number
- HU184114B HU184114B HU79FU371A HUFU000371A HU184114B HU 184114 B HU184114 B HU 184114B HU 79FU371 A HU79FU371 A HU 79FU371A HU FU000371 A HUFU000371 A HU FU000371A HU 184114 B HU184114 B HU 184114B
- Authority
- HU
- Hungary
- Prior art keywords
- preparation
- formula
- phenyl
- compound
- amino
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 238000002360 preparation method Methods 0.000 claims abstract description 96
- -1 oxy, thio, sulfinyl Chemical group 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- KSDCPEXSRBLIRA-UHFFFAOYSA-N 2-(2-chlorophenoxy)aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1Cl KSDCPEXSRBLIRA-UHFFFAOYSA-N 0.000 claims description 3
- DIDNCFGRWMVVDF-UHFFFAOYSA-N 2-[2-amino-3-(2-chlorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1OC1=CC=CC=C1Cl DIDNCFGRWMVVDF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 6
- 206010029897 Obsessive thoughts Diseases 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 125000004442 acylamino 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- 239000000203 mixture Substances 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 30
- 235000011121 sodium hydroxide Nutrition 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- 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 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 235000019270 ammonium chloride Nutrition 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 10
- 239000005751 Copper oxide Substances 0.000 description 10
- 229910000431 copper oxide Inorganic materials 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 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
- 239000011780 sodium chloride Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 7
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 7
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 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 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 229920000609 methyl cellulose Polymers 0.000 description 6
- 239000001923 methylcellulose Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- SANAOPCPUIVECT-UHFFFAOYSA-N ethyl 2-[2-amino-3-(2-chlorophenoxy)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1N SANAOPCPUIVECT-UHFFFAOYSA-N 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 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 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MDIAKIHKBBNYHF-UHFFFAOYSA-N Ethyl 2-(methylthio)acetate Chemical compound CCOC(=O)CSC MDIAKIHKBBNYHF-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004590 computer program Methods 0.000 description 3
- 231100000673 dose–response relationship Toxicity 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
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 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 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 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
- 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
- GDHDXFISRZEJIM-UHFFFAOYSA-N 2-[2-amino-3-(2-fluorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1OC1=CC=CC=C1F GDHDXFISRZEJIM-UHFFFAOYSA-N 0.000 description 2
- DQJFBAKCNDQFCD-UHFFFAOYSA-N 2-[2-amino-3-(3,4-dichlorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1OC1=CC=C(Cl)C(Cl)=C1 DQJFBAKCNDQFCD-UHFFFAOYSA-N 0.000 description 2
- VQQWRUJQVHBMRJ-UHFFFAOYSA-N 2-[2-amino-3-(3,4-dimethylphenoxy)phenyl]acetic acid Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=CC(CC(O)=O)=C1N VQQWRUJQVHBMRJ-UHFFFAOYSA-N 0.000 description 2
- ZAVQAGFQYUSGLH-UHFFFAOYSA-N 2-[2-amino-3-(3,5-dichlorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ZAVQAGFQYUSGLH-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
- JIWBIHDOWBMYTN-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-(2-fluorophenoxy)phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=C(Cl)C=C1OC1=CC=CC=C1F JIWBIHDOWBMYTN-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
- NIUVVEPVGFSHQV-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)-2-nitrophenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1[N+]([O-])=O NIUVVEPVGFSHQV-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
- 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
- UVWYCILNUYYCBG-UHFFFAOYSA-N 5-chloro-7-(2-chlorophenoxy)-1,3-dihydroindol-2-one Chemical compound C=1C(Cl)=CC=2CC(=O)NC=2C=1OC1=CC=CC=C1Cl UVWYCILNUYYCBG-UHFFFAOYSA-N 0.000 description 2
- IEWCNLUGNWUAEL-UHFFFAOYSA-N 7-(2,6-dichlorophenoxy)-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC(Cl)=C1OC1=CC=CC2=C1NC(=O)C2 IEWCNLUGNWUAEL-UHFFFAOYSA-N 0.000 description 2
- LLUCYDFRSQDQOX-UHFFFAOYSA-N 7-(2-chlorophenoxy)-3-methyl-1,3-dihydroindol-2-one Chemical compound CC1C(=O)NC2=C1C=CC=C2OC1=CC=CC=C1Cl LLUCYDFRSQDQOX-UHFFFAOYSA-N 0.000 description 2
- 206010020843 Hyperthermia Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- RPTYMYZCBFFWRB-UHFFFAOYSA-N ethyl 2-(2-acetamido-3-phenoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1NC(C)=O RPTYMYZCBFFWRB-UHFFFAOYSA-N 0.000 description 2
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- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isopropylhexane Natural products CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002739 metals Chemical class 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
- 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
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-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
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- VJNPIVICUFNXGB-UHFFFAOYSA-M sodium;2-[3-(2-chlorophenoxy)-2-nitrophenyl]acetate Chemical compound [Na+].[O-]C(=O)CC1=CC=CC(OC=2C(=CC=CC=2)Cl)=C1[N+]([O-])=O VJNPIVICUFNXGB-UHFFFAOYSA-M 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000007619 statistical method 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
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension 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
- 229940095064 tartrate Drugs 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
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7832609 | 1978-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184114B true HU184114B (en) | 1984-07-30 |
Family
ID=10498927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79FU371A HU184114B (en) | 1978-08-08 | 1979-08-08 | Process for preparing phenyl-alkanecarboxylic acid derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4472433A (en, 2012) |
| EP (1) | EP0008226B1 (en, 2012) |
| JP (1) | JPS5551041A (en, 2012) |
| AR (2) | AR228019A1 (en, 2012) |
| AT (1) | ATE5188T1 (en, 2012) |
| AU (1) | AU526877B2 (en, 2012) |
| CA (1) | CA1127160A (en, 2012) |
| DE (1) | DE2966364D1 (en, 2012) |
| DK (1) | DK331679A (en, 2012) |
| ES (3) | ES483252A1 (en, 2012) |
| GR (1) | GR68102B (en, 2012) |
| HU (1) | HU184114B (en, 2012) |
| IE (1) | IE48676B1 (en, 2012) |
| PH (1) | PH22340A (en, 2012) |
| SU (2) | SU1199197A3 (en, 2012) |
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. |
| JPH08511011A (ja) * | 1993-06-07 | 1996-11-19 | ゼネカ・リミテッド | アニリン誘導体 |
| AU2001285311B2 (en) | 2000-08-29 | 2005-09-15 | Biocon, Ltd | Immunoregulatory compounds, derivatives thereof and their use |
| JP2004529110A (ja) | 2001-03-06 | 2004-09-24 | アストラゼネカ アクチボラグ | 脈管損傷活性を有するインドール誘導体 |
| 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 |
| WO2017139414A1 (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 (en, 2012) * | 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 (en, 2012) * | 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 DE DE7979301600T patent/DE2966364D1/de not_active Expired
- 1979-08-07 AT AT79301600T patent/ATE5188T1/de active
- 1979-08-07 CA CA333,296A patent/CA1127160A/en not_active Expired
- 1979-08-07 DK DK331679A patent/DK331679A/da not_active Application Discontinuation
- 1979-08-07 SU SU792802251A patent/SU1199197A3/ru active
- 1979-08-07 EP EP79301600A patent/EP0008226B1/en not_active Expired
- 1979-08-08 AR AR277639A patent/AR228019A1/es active
- 1979-08-08 PH PH22880A patent/PH22340A/en 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 HU HU79FU371A patent/HU184114B/hu unknown
-
1980
- 1980-06-30 ES ES492954A patent/ES8105690A1/es not_active Expired
- 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 |
|---|---|
| SU1199197A3 (ru) | 1985-12-15 |
| SU1053743A3 (ru) | 1983-11-07 |
| ES483252A1 (es) | 1980-09-01 |
| AR228019A1 (es) | 1983-01-14 |
| EP0008226A3 (en) | 1980-03-05 |
| ATE5188T1 (de) | 1983-11-15 |
| EP0008226A2 (en) | 1980-02-20 |
| US4472433A (en) | 1984-09-18 |
| IE48676B1 (en) | 1985-04-17 |
| DK331679A (da) | 1980-02-09 |
| CA1127160A (en) | 1982-07-06 |
| IE791490L (en) | 1980-02-08 |
| JPS5551041A (en) | 1980-04-14 |
| ES8106482A1 (es) | 1981-07-01 |
| ES492954A0 (es) | 1981-06-16 |
| JPS6256861B2 (en, 2012) | 1987-11-27 |
| AU4946179A (en) | 1981-02-05 |
| ES492955A0 (es) | 1981-07-01 |
| AU526877B2 (en) | 1983-02-03 |
| EP0008226B1 (en) | 1983-11-02 |
| AR226446A1 (es) | 1982-07-15 |
| DE2966364D1 (en) | 1983-12-08 |
| GR68102B (en, 2012) | 1981-10-30 |
| PH22340A (en) | 1988-08-12 |
| ES8105690A1 (es) | 1981-06-16 |
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