HRP980480A2 - Ureido and thioureido derivatives of 4-amino-2(5h) -furanones and 4-amino-2(5h)-thiophenones as antitumor agents - Google Patents

Ureido and thioureido derivatives of 4-amino-2(5h) -furanones and 4-amino-2(5h)-thiophenones as antitumor agents

Info

Publication number: HRP980480A2
Authority: HR; Croatia
Prior art keywords: aminocarbonylamino; alkyl; compounds; phenyl; furanone
Prior art date: 1997-09-05

Application number

HR97115391.1A

Other languages

English (en)

Croatian (hr)

Inventor

Gerd Zimmermann

Original Assignee

Boehringer Mannheim Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-09-05

Filing date

1998-08-31

Publication date

1999-06-30

1998-08-31 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1999-06-30 Publication of HRP980480A2 publication Critical patent/HRP980480A2/hr

Links

239000002246 antineoplastic agent Substances 0.000 title claims description 3
SABBJFPNIAIRGR-UHFFFAOYSA-N 3-amino-2h-furan-5-one Chemical class NC1=CC(=O)OC1 SABBJFPNIAIRGR-UHFFFAOYSA-N 0.000 title description 3
ZAEATBXDRKDVDD-UHFFFAOYSA-N 3-amino-2h-thiophen-5-one Chemical class NC1=CC(=O)SC1 ZAEATBXDRKDVDD-UHFFFAOYSA-N 0.000 title description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 43
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 23
-1 (C1-C4)-hydroxyalkyl Chemical group 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 12
229910052717 sulfur Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
FMTQGSFFEZNCBH-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC(=O)OC1 FMTQGSFFEZNCBH-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
230000000259 anti-tumor effect Effects 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
XMUCDMOLAGBODC-UHFFFAOYSA-N 1-(3-chloro-4-ethylphenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound C1=C(Cl)C(CC)=CC=C1NC(=O)NC1=CC(=O)OC1 XMUCDMOLAGBODC-UHFFFAOYSA-N 0.000 claims description 3
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052757 nitrogen Chemical group 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
230000008569 process Effects 0.000 claims description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000001914 filtration Methods 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
206010009944 Colon cancer Diseases 0.000 description 5
208000029742 colonic neoplasm Diseases 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
208000001333 Colorectal Neoplasms Diseases 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
244000309464 bull Species 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
238000000825 ultraviolet detection Methods 0.000 description 3
CGOKYDVOQARPCI-UHFFFAOYSA-N (3-chloro-4-ethylphenyl)urea Chemical compound CCC1=CC=C(NC(N)=O)C=C1Cl CGOKYDVOQARPCI-UHFFFAOYSA-N 0.000 description 2
RECCURWJDVZHIH-UHFFFAOYSA-N (4-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 description 2
RSBADDDCEAEQPP-UHFFFAOYSA-N 1-(3-chloro-4-ethylphenyl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound C1=C(Cl)C(CC)=CC=C1NC(=O)NC1=CC(=O)SC1 RSBADDDCEAEQPP-UHFFFAOYSA-N 0.000 description 2
XWHJEWPCEMNVMV-UHFFFAOYSA-N 1-cyclohexyl-3-(5-oxo-2h-furan-3-yl)urea Chemical compound C=1C(=O)OCC=1NC(=O)NC1CCCCC1 XWHJEWPCEMNVMV-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229940043232 butyl acetate Drugs 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
238000007398 colorimetric assay Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
229960002949 fluorouracil Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000012265 solid product Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
QOQYLBCFHCBREM-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)urea Chemical compound COC1=CC(NC(N)=O)=CC(OC)=C1OC QOQYLBCFHCBREM-UHFFFAOYSA-N 0.000 description 1
KXFZOIMSGDTTMG-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound N=1C=CNC=1NC(=O)NC1=CC(=O)OC1 KXFZOIMSGDTTMG-UHFFFAOYSA-N 0.000 description 1
YGEWLTCLSSATJJ-UHFFFAOYSA-N 1-(1h-indol-3-yl)-3-(5-oxo-2h-furan-3-yl)thiourea Chemical compound O=C1OCC(NC(=S)NC=2C3=CC=CC=C3NC=2)=C1 YGEWLTCLSSATJJ-UHFFFAOYSA-N 0.000 description 1
SERSACYHGDDMHQ-UHFFFAOYSA-N 1-(1h-indol-3-yl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound C=1NC2=CC=CC=C2C=1NC(=O)NC1=CC(=O)OC1 SERSACYHGDDMHQ-UHFFFAOYSA-N 0.000 description 1
FMYDYBRZJOGLAN-UHFFFAOYSA-N 1-(1h-indol-3-yl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound C=1NC2=CC=CC=C2C=1NC(=O)NC1=CC(=O)SC1 FMYDYBRZJOGLAN-UHFFFAOYSA-N 0.000 description 1
MPMSXWPZTPWYRM-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound ClC1=CC=CC(NC(=O)NC=2COC(=O)C=2)=C1Cl MPMSXWPZTPWYRM-UHFFFAOYSA-N 0.000 description 1
ANCWDQPFOWUKGY-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2COC(=O)C=2)=C1C ANCWDQPFOWUKGY-UHFFFAOYSA-N 0.000 description 1
OSXBCSBDCLZGHK-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound FC1=CC(F)=CC=C1NC(=O)NC1=CC(=O)OC1 OSXBCSBDCLZGHK-UHFFFAOYSA-N 0.000 description 1
HMKNTZICKNCWAG-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound FC1=CC(F)=CC=C1NC(=O)NC1=CC(=O)SC1 HMKNTZICKNCWAG-UHFFFAOYSA-N 0.000 description 1
KULJPZDGMUJSQB-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound CC1=CC(C)=CC=C1NC(=O)NC1=CC(=O)OC1 KULJPZDGMUJSQB-UHFFFAOYSA-N 0.000 description 1
XTAVLAZRBFFFAJ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC(=O)OC1 XTAVLAZRBFFFAJ-UHFFFAOYSA-N 0.000 description 1
OGJRDIAFDGCKNG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC(=O)SC1 OGJRDIAFDGCKNG-UHFFFAOYSA-N 0.000 description 1
IARJWQRRAALQJH-UHFFFAOYSA-N 1-(2-chloro-4-ethylphenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound ClC1=CC(CC)=CC=C1NC(=O)NC1=CC(=O)OC1 IARJWQRRAALQJH-UHFFFAOYSA-N 0.000 description 1
NOHZNAAJTKSXOX-UHFFFAOYSA-N 1-(2-chloro-4-ethylphenyl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound ClC1=CC(CC)=CC=C1NC(=O)NC1=CC(=O)SC1 NOHZNAAJTKSXOX-UHFFFAOYSA-N 0.000 description 1
NXTUADPWMJXZNW-UHFFFAOYSA-N 1-(2-ethylphenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC(=O)OC1 NXTUADPWMJXZNW-UHFFFAOYSA-N 0.000 description 1
MDUMUVXYORRGNO-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC(=O)OC1 MDUMUVXYORRGNO-UHFFFAOYSA-N 0.000 description 1
VUJKVPFILIGWLY-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound FC1=CC=CC=C1NC(=O)NC1=CC(=O)SC1 VUJKVPFILIGWLY-UHFFFAOYSA-N 0.000 description 1
IOUCKRUDTQTJDK-UHFFFAOYSA-N 1-(2-methylphenyl)-3-(5-oxo-2h-thiophen-3-yl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC(=O)SC1 IOUCKRUDTQTJDK-UHFFFAOYSA-N 0.000 description 1
FCQYSBDKMMCUHT-UHFFFAOYSA-N 1-(2-oxo-3H-furan-3-yl)-3-phenylurea Chemical class C=1C=CC=CC=1NC(=O)NC1C=COC1=O FCQYSBDKMMCUHT-UHFFFAOYSA-N 0.000 description 1
XGKQGQQCSSHUFB-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(5-oxo-2h-furan-3-yl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC(=O)OC1 XGKQGQQCSSHUFB-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/58—One oxygen atom, e.g. butenolide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
- A—HUMAN NECESSITIES
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- 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
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/66—Nitrogen atoms
- 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
- 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Veterinary Medicine (AREA)
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Medicinal Chemistry (AREA)
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Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

HR97115391.1A 1997-09-05 1998-08-31 Ureido and thioureido derivatives of 4-amino-2(5h) -furanones and 4-amino-2(5h)-thiophenones as antitumor agents HRP980480A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP97115391		1997-09-05

Publications (1)

Publication Number	Publication Date
HRP980480A2 true HRP980480A2 (en)	1999-06-30

Family

ID=8227318

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR97115391.1A HRP980480A2 (en)	1997-09-05	1998-08-31	Ureido and thioureido derivatives of 4-amino-2(5h) -furanones and 4-amino-2(5h)-thiophenones as antitumor agents

Country Status (16)

Country	Link
US (2)	US6333346B1 (xx)
EP (1)	EP1009747A1 (xx)
JP (1)	JP2001515894A (xx)
KR (1)	KR20010023549A (xx)
CN (1)	CN1278256A (xx)
AR (1)	AR014908A1 (xx)
AU (1)	AU748490B2 (xx)
BR (1)	BR9812629A (xx)
CA (1)	CA2302284A1 (xx)
CO (1)	CO4970714A1 (xx)
HR (1)	HRP980480A2 (xx)
MA (1)	MA24668A1 (xx)
PE (1)	PE107599A1 (xx)
TR (1)	TR200000589T2 (xx)
WO (1)	WO1999012917A1 (xx)
ZA (1)	ZA988096B (xx)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1309593B1 (it) *	1999-03-05	2002-01-24	Novuspharma Spa	Composti eterociclici ad attivita' antitumorale.
KR20010094519A (ko) *	2000-03-31	2001-11-01	서경배	2,2,4,5-사중 치환된 3(2ｈ)-퓨라논 유도체의 제조 방법
GB9928696D0 (en)	1999-12-03	2000-02-02	Swan Thomas & Co Ltd	Optical devices and methods of manufacture thereof
IT1315267B1 (it) *	1999-12-23	2003-02-03	Novuspharma Spa	Derivati di 2-(1h-indol-3-il)-2-oxo-acetammidi ad attivita'antitumorale
US20060211759A1 (en) *	2001-07-26	2006-09-21	Sigma-Tau Industrie Farmaceutiche Riunite S.P.A.	Bis-heterocyclic compounds with antitumour and chemosensitising activity
WO2003018575A1 (en) *	2001-08-24	2003-03-06	Wyeth Holdings Corporation	5-substituted-3(2h)-furanones useful for inhibition of farnesyl-protein transferase
US7649012B2 (en) *	2002-07-09	2010-01-19	Fasgen, Inc.	Compounds, pharmaceutical compositions containing same, and methods of use for same
KR20040018295A (ko) *	2002-08-22	2004-03-03	임철부	항암 활성을 갖는 티오우레이도 세라마이드 유도체 및 이화합물을 함유하는 약학적 조성물
KR100555655B1 (ko) *	2002-11-20	2006-03-03	임철부	항암 활성을 갖는 우레이도 또는 티오우레이도 유도체 및이 화합물을 함유하는 약학조성물
CN1301253C (zh) *	2003-07-31	2007-02-21	中国人民解放军军事医学科学院毒物药物研究所	五元硫杂环类化合物及其用于制备治疗和预防肥胖相关疾病的药物的用途
CN101161645B (zh) *	2007-11-27	2010-06-23	南京大学	尿素类衍生物及其制备方法与用途
CN101560175B (zh) *	2009-05-08	2012-10-10	南京大学	一类硫脲类衍生物及其制备方法与用途
CN106800544B (zh) *	2017-01-19	2019-09-06	华南师范大学	3-卤-4-联苯胺基-2(5h)-呋喃酮类化合物及其在制备抗肿瘤药物中的应用

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USRE27894E (en)	1972-05-15	1974-01-22		Hydroxy-j-(j-phenylureido)crotonic acid, gamma lactone compounds
AR206143A1 (es) *	1974-04-17	1976-06-30	Du Pont	Procedimiento para la preparacion de compuestos de 1 - t - alquil - 3 - (2,5 - dihidro - 5 - oxo - 3 - furil) ureas
SE7702004L (sv) *	1976-03-24	1977-09-25	Du Pont	Antihypertensiva furylkarbamider
JPS63174983A (ja) *	1987-01-16	1988-07-19	Sumitomo Chem Co Ltd	アミノブテノリド誘導体、その製造法およびそれを有効成分とする除草剤

1998
- 1998-08-24 CO CO98048243A patent/CO4970714A1/es unknown
- 1998-08-31 HR HR97115391.1A patent/HRP980480A2/hr not_active Application Discontinuation
- 1998-09-01 JP JP2000510725A patent/JP2001515894A/ja active Pending
- 1998-09-01 PE PE1998000812A patent/PE107599A1/es not_active Application Discontinuation
- 1998-09-01 AU AU95350/98A patent/AU748490B2/en not_active Ceased
- 1998-09-01 EP EP98948889A patent/EP1009747A1/en not_active Withdrawn
- 1998-09-01 US US09/485,709 patent/US6333346B1/en not_active Expired - Fee Related
- 1998-09-01 TR TR2000/00589T patent/TR200000589T2/xx unknown
- 1998-09-01 MA MA25237A patent/MA24668A1/fr unknown
- 1998-09-01 BR BR9812629-6A patent/BR9812629A/pt not_active IP Right Cessation
- 1998-09-01 CN CN98810803A patent/CN1278256A/zh active Pending
- 1998-09-01 KR KR1020007002197A patent/KR20010023549A/ko not_active Application Discontinuation
- 1998-09-01 CA CA002302284A patent/CA2302284A1/en not_active Abandoned
- 1998-09-01 WO PCT/EP1998/005524 patent/WO1999012917A1/en not_active Application Discontinuation
- 1998-09-03 AR ARP980104400A patent/AR014908A1/es unknown
- 1998-09-04 ZA ZA9808096A patent/ZA988096B/xx unknown
2001
- 2001-11-08 US US09/986,310 patent/US20020058694A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US6333346B1 (en)	2001-12-25
WO1999012917A1 (en)	1999-03-18
PE107599A1 (es)	1999-11-03
BR9812629A (pt)	2000-08-22
AR014908A1 (es)	2001-04-11
CN1278256A (zh)	2000-12-27
AU748490B2 (en)	2002-06-06
ZA988096B (en)	2000-03-22
MA24668A1 (fr)	1999-07-01
CA2302284A1 (en)	1999-03-18
AU9535098A (en)	1999-03-29
TR200000589T2 (tr)	2000-07-21
CO4970714A1 (es)	2000-11-07
EP1009747A1 (en)	2000-06-21
JP2001515894A (ja)	2001-09-25
KR20010023549A (ko)	2001-03-26
US20020058694A1 (en)	2002-05-16

Legal Events

Date	Code	Title	Description
1999-06-30	A1OB	Publication of a patent application
1999-08-02	PNAN	Change of the applicant name, address/residence	Owner name: ROCHE DIAGNOSTICS GMBH, DE
1999-12-30	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2009-07-06	ODBC	Application rejected

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