CH534688A - Verfahren zur Herstellung von Aminothiophen-Derivaten - Google Patents
Verfahren zur Herstellung von Aminothiophen-DerivatenInfo
- Publication number
- CH534688A CH534688A CH497666A CH497666A CH534688A CH 534688 A CH534688 A CH 534688A CH 497666 A CH497666 A CH 497666A CH 497666 A CH497666 A CH 497666A CH 534688 A CH534688 A CH 534688A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- alkyl
- anilino
- thiophene
- cyano
- Prior art date
Links
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 aminoalkyl halide Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 230000000875 corresponding effect Effects 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- WPCVVFYUHADPCA-UHFFFAOYSA-N 2,5-dihydrothiophen-3-amine Chemical class NC=1CSCC1 WPCVVFYUHADPCA-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005521 carbonamide group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 5
- 229960002895 phenylbutazone Drugs 0.000 abstract description 5
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 abstract description 5
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 abstract description 3
- 206010015150 Erythema Diseases 0.000 abstract description 3
- 241000700198 Cavia Species 0.000 abstract description 2
- 206010030113 Oedema Diseases 0.000 abstract description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract description 2
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- BYOASTMEXDDSMQ-UHFFFAOYSA-N 2,5-dihydrothiophene-3-carbonitrile Chemical class N#CC1=CCSC1 BYOASTMEXDDSMQ-UHFFFAOYSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- PQEGEBSTPQVBSW-UHFFFAOYSA-N 3-(2,3-dimethylanilino)thiophene-2-carboxylic acid Chemical compound CC1=C(NC2=C(SC=C2)C(=O)O)C=CC=C1C PQEGEBSTPQVBSW-UHFFFAOYSA-N 0.000 description 2
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 2
- CWEUKXMDWMAICX-UHFFFAOYSA-N 4-(2,6-dichloroanilino)thiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1NC1=C(Cl)C=CC=C1Cl CWEUKXMDWMAICX-UHFFFAOYSA-N 0.000 description 2
- MZZCNHHJVYCQRD-UHFFFAOYSA-N 4-(2-chloro-3-methylanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=CC=C1C MZZCNHHJVYCQRD-UHFFFAOYSA-N 0.000 description 2
- PSHCYDHEWNLNKF-UHFFFAOYSA-N 4-(2-chloroanilino)thiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1NC1=CC=CC=C1Cl PSHCYDHEWNLNKF-UHFFFAOYSA-N 0.000 description 2
- YTZRDPYRBNHGRR-UHFFFAOYSA-N 4-[3-(trifluoromethyl)anilino]-2,5-dihydrothiophene-3-carbonitrile Chemical compound FC(C=1C=C(NC=2CSCC2C#N)C=CC1)(F)F YTZRDPYRBNHGRR-UHFFFAOYSA-N 0.000 description 2
- LLSVPXMALQOPAA-UHFFFAOYSA-N 4-[3-(trifluoromethyl)anilino]thiophene-3-carbonitrile Chemical compound FC(C=1C=C(NC2=CSC=C2C#N)C=CC1)(F)F LLSVPXMALQOPAA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- RUEWFRBGWGXUEM-UHFFFAOYSA-N methyl 4-(2,6-dichloroanilino)-5-methylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(C)=C1NC1=C(Cl)C=CC=C1Cl RUEWFRBGWGXUEM-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- STOSPPMGXZPHKP-UHFFFAOYSA-N tetrachlorohydroquinone Chemical compound OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl STOSPPMGXZPHKP-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical class N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 1
- RXTJLDXSGNEJIT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-amine Chemical compound NC1=CC=CC2=C1CCC2 RXTJLDXSGNEJIT-UHFFFAOYSA-N 0.000 description 1
- LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 description 1
- WURYWHAKEJHAOV-UHFFFAOYSA-N 2,5-dihydrothiophene Chemical class C1SCC=C1 WURYWHAKEJHAOV-UHFFFAOYSA-N 0.000 description 1
- AYVZXDFCFQSWJD-UHFFFAOYSA-N 2,6-dichloro-3-methylaniline Chemical compound CC1=CC=C(Cl)C(N)=C1Cl AYVZXDFCFQSWJD-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- XGZLERCWRSOYGY-UHFFFAOYSA-N 3-(2,4,6-trichloro-3-methylanilino)thiophene-2-carboxylic acid Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C(=C(C(=C1)Cl)C)Cl XGZLERCWRSOYGY-UHFFFAOYSA-N 0.000 description 1
- SSSLIOXNADPBIC-UHFFFAOYSA-N 3-(2,4,6-trichloroanilino)thiophene-2-carboxylic acid Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C(=CC(=C1)Cl)Cl SSSLIOXNADPBIC-UHFFFAOYSA-N 0.000 description 1
- ZHYPJWHNBWHVTJ-UHFFFAOYSA-N 3-(2,4,6-trimethylanilino)thiophene-2-carboxylic acid Chemical compound CC1=C(NC2=C(SC=C2)C(=O)O)C(=CC(=C1)C)C ZHYPJWHNBWHVTJ-UHFFFAOYSA-N 0.000 description 1
- TYGSIIVEVSOBEY-UHFFFAOYSA-N 3-(2,6-dichloro-4-ethoxyanilino)thiophene-2-carboxylic acid Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C(=CC(=C1)OCC)Cl TYGSIIVEVSOBEY-UHFFFAOYSA-N 0.000 description 1
- GKBXCBJESPCPOH-UHFFFAOYSA-N 3-(2,6-dichloroanilino)-2-methyl-3H-thiophene-2-carboxylic acid Chemical compound CC1(SC=CC1NC1=C(C=CC=C1Cl)Cl)C(=O)O GKBXCBJESPCPOH-UHFFFAOYSA-N 0.000 description 1
- SLWLIBFEBFJIMY-UHFFFAOYSA-N 3-(2,6-dichloroanilino)thiophene-2-carboxylic acid Chemical compound S1C=CC(NC=2C(=CC=CC=2Cl)Cl)=C1C(=O)O SLWLIBFEBFJIMY-UHFFFAOYSA-N 0.000 description 1
- FOSQFGVKHUAVNE-UHFFFAOYSA-N 3-(2,6-dimethylanilino)thiophene-2-carboxylic acid Chemical compound CC1=C(NC2=C(SC=C2)C(=O)O)C(=CC=C1)C FOSQFGVKHUAVNE-UHFFFAOYSA-N 0.000 description 1
- MGKNOLWSFIPVRY-UHFFFAOYSA-N 3-(2-chloro-3-methylanilino)thiophene-2-carboxylic acid Chemical compound CC1=CC=CC(NC2=C(SC=C2)C(O)=O)=C1Cl MGKNOLWSFIPVRY-UHFFFAOYSA-N 0.000 description 1
- JQGVDMHNXRQCJT-UHFFFAOYSA-N 3-(2-chloro-5-methylanilino)thiophene-2-carboxylic acid Chemical compound CC1=CC=C(Cl)C(NC2=C(SC=C2)C(O)=O)=C1 JQGVDMHNXRQCJT-UHFFFAOYSA-N 0.000 description 1
- NNHXRUDOPLVTMS-UHFFFAOYSA-N 3-(2-chloroanilino)thiophene-2-carboxylic acid Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C=CC=C1 NNHXRUDOPLVTMS-UHFFFAOYSA-N 0.000 description 1
- YUGHWVNGFOVRSV-UHFFFAOYSA-N 3-(4-ethoxyanilino)thiophene-2-carboxylic acid Chemical compound C(C)OC1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 YUGHWVNGFOVRSV-UHFFFAOYSA-N 0.000 description 1
- DPBDOUSDHLHDRA-UHFFFAOYSA-N 3-(4-propan-2-ylanilino)thiophene-2-carboxylic acid Chemical compound C(C)(C)C1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 DPBDOUSDHLHDRA-UHFFFAOYSA-N 0.000 description 1
- DTPVHHHYUHDVLY-UHFFFAOYSA-N 3-[2-(trifluoromethyl)anilino]thiophene-2-carboxylic acid Chemical compound S1C=CC(NC=2C(=CC=CC=2)C(F)(F)F)=C1C(=O)O DTPVHHHYUHDVLY-UHFFFAOYSA-N 0.000 description 1
- FRKPCXYPIHAOFI-UHFFFAOYSA-N 3-methylaniline Chemical compound [CH2]C1=CC=CC(N)=C1 FRKPCXYPIHAOFI-UHFFFAOYSA-N 0.000 description 1
- ULQFPGOVDGGDDX-UHFFFAOYSA-N 4-(2,3-dichloroanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound ClC1=C(NC=2CSCC=2C#N)C=CC=C1Cl ULQFPGOVDGGDDX-UHFFFAOYSA-N 0.000 description 1
- WYQDLENRCGHSPX-UHFFFAOYSA-N 4-(2,3-dichloroanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=CC=C1Cl WYQDLENRCGHSPX-UHFFFAOYSA-N 0.000 description 1
- GYYMVVULHOGBSH-UHFFFAOYSA-N 4-(2,3-dimethylanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound CC1=C(NC=2CSCC=2C#N)C=CC=C1C GYYMVVULHOGBSH-UHFFFAOYSA-N 0.000 description 1
- WXHIHVGMTKXUAU-UHFFFAOYSA-N 4-(2,3-dimethylanilino)thiophene-3-carbonitrile Chemical compound CC1=C(NC2=CSC=C2C#N)C=CC=C1C WXHIHVGMTKXUAU-UHFFFAOYSA-N 0.000 description 1
- VBYQGFVYASOKSL-UHFFFAOYSA-N 4-(2,4,6-trimethylanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound CC1=C(NC=2CSCC=2C#N)C(=CC(=C1)C)C VBYQGFVYASOKSL-UHFFFAOYSA-N 0.000 description 1
- WCYVGOMGUCKGFX-UHFFFAOYSA-N 4-(2,4-dichloro-5-methylanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=C(C(=C1)Cl)C WCYVGOMGUCKGFX-UHFFFAOYSA-N 0.000 description 1
- ZQSQEBFJYFANAM-UHFFFAOYSA-N 4-(2,6-dichloroanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound ClC1=CC=CC(Cl)=C1NC1=C(C#N)CSC1 ZQSQEBFJYFANAM-UHFFFAOYSA-N 0.000 description 1
- SGGWYLXMEYVDOE-UHFFFAOYSA-N 4-(2,6-dichloroanilino)thiophene-3-carbonitrile Chemical compound ClC1=CC=CC(Cl)=C1NC1=CSC=C1C#N SGGWYLXMEYVDOE-UHFFFAOYSA-N 0.000 description 1
- VJIBENZYQWSMHS-UHFFFAOYSA-N 4-(2,6-dimethylanilino)thiophene-3-carbonitrile Chemical compound CC1=C(NC2=CSC=C2C#N)C(=CC=C1)C VJIBENZYQWSMHS-UHFFFAOYSA-N 0.000 description 1
- SBTOIPCXKHBWKA-UHFFFAOYSA-N 4-(2-chloro-3-methylanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound ClC1=C(NC=2CSCC=2C#N)C=CC=C1C SBTOIPCXKHBWKA-UHFFFAOYSA-N 0.000 description 1
- RWCWGKQEAGPFOE-UHFFFAOYSA-N 4-(2-chloro-6-methylanilino)-2,5-dihydrothiophene-3-carbonitrile Chemical compound ClC1=C(NC=2CSCC=2C#N)C(=CC=C1)C RWCWGKQEAGPFOE-UHFFFAOYSA-N 0.000 description 1
- MAGMHVGCLSZEIT-UHFFFAOYSA-N 4-(2-chloroanilino)thiophene-3-carbonitrile Chemical compound ClC1=C(NC2=CSC=C2C#N)C=CC=C1 MAGMHVGCLSZEIT-UHFFFAOYSA-N 0.000 description 1
- VEFUBIQEJIFCRQ-UHFFFAOYSA-N 4-(3,4-dimethylanilino)thiophene-3-carbonitrile Chemical compound CC=1C=C(NC2=CSC=C2C#N)C=CC=1C VEFUBIQEJIFCRQ-UHFFFAOYSA-N 0.000 description 1
- RBIIWWZZORODKE-UHFFFAOYSA-N 4-(4-ethoxyanilino)thiophene-3-carbonitrile Chemical compound C(C)OC1=CC=C(NC2=CSC=C2C#N)C=C1 RBIIWWZZORODKE-UHFFFAOYSA-N 0.000 description 1
- VQKAQKOHQUHGTN-UHFFFAOYSA-N 4-chloro-N,N-diethoxyaniline Chemical compound CCON(OCC)C1=CC=C(Cl)C=C1 VQKAQKOHQUHGTN-UHFFFAOYSA-N 0.000 description 1
- SLMYAIGAJWJBKI-UHFFFAOYSA-N 4-cyclohexyl-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C2CCCCC2)=C1 SLMYAIGAJWJBKI-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 1
- MOXOFSFWYLTCFU-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-2-amine Chemical compound C1CCCC2=CC(N)=CC=C21 MOXOFSFWYLTCFU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DJQVGQNLOQVRGF-UHFFFAOYSA-N C(C)(C)C1=CC=C(NC2=CSC=C2C#N)C=C1 Chemical compound C(C)(C)C1=CC=C(NC2=CSC=C2C#N)C=C1 DJQVGQNLOQVRGF-UHFFFAOYSA-N 0.000 description 1
- PLNOERBGMKDTBI-UHFFFAOYSA-N C(C)OC(=O)C=1C(=CSC=1)NC1=C(C=CC=C1Cl)Cl Chemical compound C(C)OC(=O)C=1C(=CSC=1)NC1=C(C=CC=C1Cl)Cl PLNOERBGMKDTBI-UHFFFAOYSA-N 0.000 description 1
- PGUODAXRIRBPAO-UHFFFAOYSA-N C1(CCCCC1)C1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 Chemical compound C1(CCCCC1)C1=CC=C(NC2=C(SC=C2)C(=O)O)C=C1 PGUODAXRIRBPAO-UHFFFAOYSA-N 0.000 description 1
- YDFAYSIZBKGBJD-UHFFFAOYSA-N C1(CCCCC1)C1=CC=C(NC2=CSC=C2C#N)C=C1 Chemical compound C1(CCCCC1)C1=CC=C(NC2=CSC=C2C#N)C=C1 YDFAYSIZBKGBJD-UHFFFAOYSA-N 0.000 description 1
- ZTNHSLGYTSKQFE-UHFFFAOYSA-N CC(C(Cl)=C(C=C1)NC2=CSC=C2C#N)=C1Cl Chemical compound CC(C(Cl)=C(C=C1)NC2=CSC=C2C#N)=C1Cl ZTNHSLGYTSKQFE-UHFFFAOYSA-N 0.000 description 1
- PZPBWAVBYJPOHL-UHFFFAOYSA-N CC(C=C1NC2=C(C(O)=O)SC=C2)=CC=C1OCC1=CC=CC=C1 Chemical compound CC(C=C1NC2=C(C(O)=O)SC=C2)=CC=C1OCC1=CC=CC=C1 PZPBWAVBYJPOHL-UHFFFAOYSA-N 0.000 description 1
- ZFJDUFGIOGVEKX-UHFFFAOYSA-N CC(C=C1NC2=CSC=C2C#N)=CC=C1OCC1=CC=CC=C1 Chemical compound CC(C=C1NC2=CSC=C2C#N)=CC=C1OCC1=CC=CC=C1 ZFJDUFGIOGVEKX-UHFFFAOYSA-N 0.000 description 1
- STACAJVSXFEKQD-UHFFFAOYSA-N CC1=C(NC=2CSCC2C#N)C(=CC=C1)C Chemical compound CC1=C(NC=2CSCC2C#N)C(=CC=C1)C STACAJVSXFEKQD-UHFFFAOYSA-N 0.000 description 1
- QNHAMNFIEMUZIS-UHFFFAOYSA-N ClC1=C(NC2=C(SC=C2)C(=O)O)C(=C(C(=C1)OCC)C)Cl Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C(=C(C(=C1)OCC)C)Cl QNHAMNFIEMUZIS-UHFFFAOYSA-N 0.000 description 1
- SSLBLYBNAHUHLA-UHFFFAOYSA-N ClC1=C(NC2=C(SC=C2)C(=O)O)C(=CC=C1)C Chemical compound ClC1=C(NC2=C(SC=C2)C(=O)O)C(=CC=C1)C SSLBLYBNAHUHLA-UHFFFAOYSA-N 0.000 description 1
- SKPJYPYPGNKSAB-UHFFFAOYSA-N ClC1=C(NC2=CSC=C2C#N)C(=C(C(=C1)OCC)C)Cl Chemical compound ClC1=C(NC2=CSC=C2C#N)C(=C(C(=C1)OCC)C)Cl SKPJYPYPGNKSAB-UHFFFAOYSA-N 0.000 description 1
- HECFTSDIFBOZNQ-UHFFFAOYSA-N ClC1=C(NC2=CSC=C2C#N)C(=CC(=C1)Cl)Cl Chemical compound ClC1=C(NC2=CSC=C2C#N)C(=CC(=C1)Cl)Cl HECFTSDIFBOZNQ-UHFFFAOYSA-N 0.000 description 1
- KLKKNDAXUPRGKT-UHFFFAOYSA-N ClC1=C(NC2=CSC=C2C#N)C(=CC=C1)C Chemical compound ClC1=C(NC2=CSC=C2C#N)C(=CC=C1)C KLKKNDAXUPRGKT-UHFFFAOYSA-N 0.000 description 1
- XEMVYXLZOQKOGA-UHFFFAOYSA-N ClC1=C(NC2=CSC=C2C#N)C=C(C=C1)C Chemical compound ClC1=C(NC2=CSC=C2C#N)C=C(C=C1)C XEMVYXLZOQKOGA-UHFFFAOYSA-N 0.000 description 1
- JUYUHFQMTHCVGE-UHFFFAOYSA-N ClC1=C(NC2=CSC=C2C(=O)N)C=CC=C1C Chemical compound ClC1=C(NC2=CSC=C2C(=O)N)C=CC=C1C JUYUHFQMTHCVGE-UHFFFAOYSA-N 0.000 description 1
- OBKRUJNEJCOXQP-UHFFFAOYSA-N ClC1=C(NC=2CSCC=2C#N)C=C(C=C1)C Chemical compound ClC1=C(NC=2CSCC=2C#N)C=C(C=C1)C OBKRUJNEJCOXQP-UHFFFAOYSA-N 0.000 description 1
- AHTLSMZOCZYZDW-UHFFFAOYSA-N ClC1=C(NC=2CSCC=2C#N)C=CC(=C1C)Cl Chemical compound ClC1=C(NC=2CSCC=2C#N)C=CC(=C1C)Cl AHTLSMZOCZYZDW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MMXHWCKMEVVPBO-UHFFFAOYSA-N FC(C=1C=C(NC2=C(SC=C2)C(=O)O)C=CC1)(F)F Chemical compound FC(C=1C=C(NC2=C(SC=C2)C(=O)O)C=CC1)(F)F MMXHWCKMEVVPBO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- XAOPHVUFVAHMIL-UHFFFAOYSA-N N#CC(CSC1)=C1NC(C(Cl)=CC(Cl)=C1)=C1Cl Chemical compound N#CC(CSC1)=C1NC(C(Cl)=CC(Cl)=C1)=C1Cl XAOPHVUFVAHMIL-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- WBCVLKGXSJBSET-UHFFFAOYSA-M [Na+].ClC1=C(NC2=CSC=C2C(=O)[O-])C(=CC=C1)Cl Chemical compound [Na+].ClC1=C(NC2=CSC=C2C(=O)[O-])C(=CC=C1)Cl WBCVLKGXSJBSET-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N alpha-mercaptoacetic acid Natural products OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
- KUVIRDUPAGKTER-UHFFFAOYSA-N n-phenylmethoxyaniline Chemical compound C=1C=CC=CC=1CONC1=CC=CC=C1 KUVIRDUPAGKTER-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical class N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- 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
- C07D333/26—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 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1780268A CH508647A (de) | 1965-04-10 | 1966-04-05 | Verfahren zur Herstellung von Aminothiophen-Derivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0045788 | 1965-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH534688A true CH534688A (de) | 1973-03-15 |
Family
ID=7100669
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH497666A CH534688A (de) | 1965-04-10 | 1966-04-05 | Verfahren zur Herstellung von Aminothiophen-Derivaten |
| CH1780368A CH547816A (de) | 1965-04-10 | 1966-04-05 | Verfahren zur herstellung von aminothiophen-derivaten. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1780368A CH547816A (de) | 1965-04-10 | 1966-04-05 | Verfahren zur herstellung von aminothiophen-derivaten. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3445473A (OSRAM) |
| AT (3) | AT260919B (OSRAM) |
| BE (1) | BE679374A (OSRAM) |
| BR (1) | BR6678492D0 (OSRAM) |
| CH (2) | CH534688A (OSRAM) |
| DK (1) | DK121127B (OSRAM) |
| ES (1) | ES325278A1 (OSRAM) |
| FR (1) | FR5539M (OSRAM) |
| GB (1) | GB1133850A (OSRAM) |
| IL (1) | IL25505A (OSRAM) |
| NL (1) | NL6604742A (OSRAM) |
| NO (1) | NO118669B (OSRAM) |
| SE (1) | SE316489B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005559A1 (de) * | 1978-05-24 | 1979-11-28 | Byk Gulden Lomberg Chemische Fabrik GmbH | Phenylaminothiophenessigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4360681A (en) * | 1973-12-03 | 1982-11-23 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
| US4299968A (en) * | 1973-12-03 | 1981-11-10 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
| US4317915A (en) * | 1976-08-23 | 1982-03-02 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
| US4428963A (en) | 1976-08-23 | 1984-01-31 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
| DE3861268D1 (de) * | 1987-07-07 | 1991-01-24 | Shell Int Research | Verfahren zur herstellung von thiophenderivaten. |
| US5166346A (en) * | 1987-12-11 | 1992-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides |
| US5811447A (en) | 1993-01-28 | 1998-09-22 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| US6515009B1 (en) | 1991-09-27 | 2003-02-04 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| US6251920B1 (en) | 1993-05-13 | 2001-06-26 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies |
| US6491938B2 (en) | 1993-05-13 | 2002-12-10 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| ATE406909T1 (de) * | 1993-05-13 | 2008-09-15 | Poniard Pharmaceuticals Inc | Prävention und behandlung von pathologien, die mit einer abnormalen proliferationglatter muskelzellen verbunden sind |
| US6136984A (en) * | 1996-04-22 | 2000-10-24 | Novo Nordisk A/S | Solid phase and combinatorial synthesis of substituted thiophenes and of arrays of substituted thiophenes |
| AU6959898A (en) * | 1997-04-11 | 1998-11-11 | David J. Grainger | Compounds and therapies for the prevention of vascular and non-vascular pathol ogies |
| US6613083B2 (en) | 2001-05-02 | 2003-09-02 | Eckhard Alt | Stent device and method |
| JP7323913B2 (ja) * | 2019-04-12 | 2023-08-09 | 国立大学法人 筑波大学 | 睡眠誘導剤である複素環化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097206A (en) * | 1962-03-19 | 1963-07-09 | Smith Kline French Lab | Aminomethylthienyl and furyl alcohol derivatives |
-
1966
- 1966-03-30 US US538569A patent/US3445473A/en not_active Expired - Lifetime
- 1966-03-31 IL IL25505A patent/IL25505A/en unknown
- 1966-04-05 CH CH497666A patent/CH534688A/de not_active IP Right Cessation
- 1966-04-05 CH CH1780368A patent/CH547816A/xx not_active IP Right Cessation
- 1966-04-05 BR BR178492/66A patent/BR6678492D0/pt unknown
- 1966-04-06 NO NO162507A patent/NO118669B/no unknown
- 1966-04-06 DK DK184666AA patent/DK121127B/da unknown
- 1966-04-06 ES ES0325278A patent/ES325278A1/es not_active Expired
- 1966-04-06 SE SE4666/66A patent/SE316489B/xx unknown
- 1966-04-07 NL NL6604742A patent/NL6604742A/xx unknown
- 1966-04-08 AT AT338466A patent/AT260919B/de active
- 1966-04-08 AT AT142167A patent/AT263761B/de active
- 1966-04-08 AT AT142067A patent/AT263760B/de active
- 1966-04-12 BE BE679374D patent/BE679374A/xx unknown
- 1966-04-12 GB GB15940/66A patent/GB1133850A/en not_active Expired
- 1966-07-08 FR FR68769A patent/FR5539M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005559A1 (de) * | 1978-05-24 | 1979-11-28 | Byk Gulden Lomberg Chemische Fabrik GmbH | Phenylaminothiophenessigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| AT260919B (de) | 1968-03-25 |
| FR5539M (OSRAM) | 1967-11-13 |
| SE316489B (OSRAM) | 1969-10-27 |
| BR6678492D0 (pt) | 1973-09-18 |
| GB1133850A (en) | 1968-11-20 |
| AT263761B (de) | 1968-08-12 |
| CH547816A (de) | 1974-04-11 |
| IL25505A (en) | 1970-02-19 |
| DK121127B (da) | 1971-09-13 |
| NL6604742A (OSRAM) | 1966-10-11 |
| BE679374A (OSRAM) | 1966-10-12 |
| US3445473A (en) | 1969-05-20 |
| AT263760B (de) | 1968-08-12 |
| NO118669B (OSRAM) | 1970-01-26 |
| ES325278A1 (es) | 1967-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH534688A (de) | Verfahren zur Herstellung von Aminothiophen-Derivaten | |
| CH619209A5 (OSRAM) | ||
| AT262274B (de) | Verfahren zur Herstellung neuer Indolderivate | |
| DE2537070C2 (OSRAM) | ||
| DE2655009C2 (OSRAM) | ||
| EP0021207B1 (de) | Alphacarbamoyl-pyrrolpropionitrile, Verfahren zu ihrer Herstellung, sowie pharmazeutische Präparate die diese Verbindungen enthalten | |
| DE1815802A1 (de) | Verfahren zur Herstellung von substituierten Phenylessigsaeuren | |
| DE1618465C3 (de) | Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2149070B2 (de) | Phenoxyalkylcarbonsaeurederivate und deren salze, verfahren zu deren herstellung und arzneimittel | |
| AT209895B (de) | Verfahren zur Herstellung von 3-Amino-2,4,6-trijodbenzoylverbindungen | |
| DE2007700C2 (de) | Substituierte o-Anilino-phenäthylalkohole, Verfahren zu ihrer Herstellung und therapeutische Präparate | |
| DE3247454A1 (de) | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2144641C3 (de) | Phenylacethydroxamsäuren und Verfahren zu ihrer Herstellung | |
| DE1493705C2 (de) | 3-Phenylamino thiophen -4-carbonsäuren und Verfahren zu ihrer Herstellung | |
| EP0012435A2 (de) | Isoxazolderivate, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und bei dem Verfahren benötigte Zwischenprodukte | |
| DE3641907A1 (de) | 4h-benzo(4,5)cyclohepta(1,2-b)thiophen derivate | |
| CH452528A (de) | Verfahren zur Herstellung von neuen Derivaten eines Pyrido-oxazins | |
| AT354432B (de) | Verfahren zur herstellung von 3-indolylessig- saeuren | |
| AT209894B (de) | Verfahren zur Herstellung von neuen Anthranilsäurederivaten | |
| AT330779B (de) | Verfahren zur herstellung von neuen chinolinessigsaurederivaten und ihren salzen | |
| AT211296B (de) | Verfahren zur Herstellung von neuen Sulfamylanthranilsäuren | |
| AT216495B (de) | Verfahren zur Herstellung von neuen Phenylalaninderivaten und deren Salzen | |
| AT267503B (de) | Verfahren zur Herstellung von neuen o-Aroylaminoaryloxy- bzw. -arylthioessigsäuren | |
| CH508647A (de) | Verfahren zur Herstellung von Aminothiophen-Derivaten | |
| DE1595911C (de) | IH 2,3 Benzoxazin 4(3H) one und Ver fahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |