JP2005538953A5 - - Google Patents
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- JP2005538953A5 JP2005538953A5 JP2004507462A JP2004507462A JP2005538953A5 JP 2005538953 A5 JP2005538953 A5 JP 2005538953A5 JP 2004507462 A JP2004507462 A JP 2004507462A JP 2004507462 A JP2004507462 A JP 2004507462A JP 2005538953 A5 JP2005538953 A5 JP 2005538953A5
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- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- phenyl
- amino
- hydrogen
- Prior art date
- Legal status (The legal status 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 status listed.)
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- -1 benzylthio Chemical group 0.000 claims 228
- 125000000217 alkyl group Chemical group 0.000 claims 61
- 150000001875 compounds Chemical class 0.000 claims 53
- 229910052739 hydrogen Inorganic materials 0.000 claims 40
- 239000001257 hydrogen Substances 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 32
- 150000002431 hydrogen Chemical class 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 239000004305 biphenyl Substances 0.000 claims 3
- 235000010290 biphenyl Nutrition 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 125000005108 alkenylthio group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 claims 1
- STTQUORLVKVXEA-UHFFFAOYSA-N 1-[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)-3-methylphenyl]-3-(4-methylsulfonylbutyl)urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)NC(=O)NCCCCS(C)(=O)=O)=C1SC STTQUORLVKVXEA-UHFFFAOYSA-N 0.000 claims 1
- ZZDRVTPUEMSIAM-UHFFFAOYSA-N 12-[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)-3-methylanilino]-12-oxododecanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)NC(=O)CCCCCCCCCCC(O)=O)=C1SC ZZDRVTPUEMSIAM-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- XNFSBPZYTHFLAW-UHFFFAOYSA-N 3-[2-[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)-3-methylanilino]-2-oxoethyl]sulfanylpropanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)NC(=O)CSCCC(O)=O)=C1SC XNFSBPZYTHFLAW-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- UHAYFACGPOOBAS-UHFFFAOYSA-N 4-[3-[2-amino-4-(diaminomethylideneamino)-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)N)=C1SC UHAYFACGPOOBAS-UHFFFAOYSA-N 0.000 claims 1
- FNIDUWHWPHMNRS-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(2-phenylethyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCC=3C=CC=CC=3)=CC=2)C)=C1SC FNIDUWHWPHMNRS-UHFFFAOYSA-N 0.000 claims 1
- PWFBQFCROCFGLJ-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(3-methylbutyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCC(C)C)=CC=2)C)=C1SC PWFBQFCROCFGLJ-UHFFFAOYSA-N 0.000 claims 1
- ULNALTNISMRENO-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(3-methylsulfonylpropyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCCS(C)(=O)=O)=CC=2)C)=C1SC ULNALTNISMRENO-UHFFFAOYSA-N 0.000 claims 1
- ULTLMBJOYDIJFK-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(3-phenylpropyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCCC=3C=CC=CC=3)=CC=2)C)=C1SC ULTLMBJOYDIJFK-UHFFFAOYSA-N 0.000 claims 1
- AWHRWYRCIPVDOL-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(4-methylsulfonylbutyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCCCS(C)(=O)=O)=CC=2)C)=C1SC AWHRWYRCIPVDOL-UHFFFAOYSA-N 0.000 claims 1
- KXXBWLKFVKCEEN-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(5-methylsulfonylpentyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCCCCS(C)(=O)=O)=CC=2)C)=C1SC KXXBWLKFVKCEEN-UHFFFAOYSA-N 0.000 claims 1
- RHCQKAINXNIPEA-UHFFFAOYSA-N 4-[3-[2-methyl-4-[[n'-(6-methylsulfonylhexyl)carbamimidoyl]amino]phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NCCCCCCS(C)(=O)=O)=CC=2)C)=C1SC RHCQKAINXNIPEA-UHFFFAOYSA-N 0.000 claims 1
- ZGFQBDHEAYUVPJ-UHFFFAOYSA-N 4-[3-[4-(4,5-dihydro-1h-imidazol-2-ylamino)-2-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC=3NCCN=3)=CC=2)C)=C1SC ZGFQBDHEAYUVPJ-UHFFFAOYSA-N 0.000 claims 1
- ICBXYKUKGFATIC-UHFFFAOYSA-N 4-[3-[4-(diaminomethylideneamino)-2-methyl-6-nitrophenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)[N+]([O-])=O)=C1SC ICBXYKUKGFATIC-UHFFFAOYSA-N 0.000 claims 1
- OWXGMXITAWITJA-UHFFFAOYSA-N 4-[3-[4-(diaminomethylideneamino)-2-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2)N=C(N)N)C)=C1SC OWXGMXITAWITJA-UHFFFAOYSA-N 0.000 claims 1
- ZUBDHEJDDVQTSH-UHFFFAOYSA-N 4-[3-[4-[(n'-hexylcarbamimidoyl)amino]-2-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC(NC(N)=NCCCCCC)=CC=C1C1=CC=CC(S(=O)(=O)C2=C(SC(=C2)C(N)=N)SC)=C1 ZUBDHEJDDVQTSH-UHFFFAOYSA-N 0.000 claims 1
- RQYMUSGXRSGQLW-UHFFFAOYSA-N 4-[3-[4-[carbamimidoyl(methyl)amino]-2-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2)N(C)C(N)=N)C)=C1SC RQYMUSGXRSGQLW-UHFFFAOYSA-N 0.000 claims 1
- MZFRLCUWJONGTF-UHFFFAOYSA-N 4-[5-[[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)-3-methylphenyl]carbamoylamino]pentoxy]benzoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)NC(=O)NCCCCCOC=2C=CC(=CC=2)C(O)=O)=C1SC MZFRLCUWJONGTF-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- KEUAXKSEFCKGDL-UHFFFAOYSA-N 6-[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)-3-methylanilino]-6-oxohexanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)NC(=O)CCCCC(O)=O)=C1SC KEUAXKSEFCKGDL-UHFFFAOYSA-N 0.000 claims 1
- VUYMZSKQUKGFAJ-UHFFFAOYSA-N 6-[[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)phenyl]carbamoylamino]hexanoic acid Chemical compound S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=N)=CC=2)NC(=O)NCCCCCC(O)=O)=C1SC VUYMZSKQUKGFAJ-UHFFFAOYSA-N 0.000 claims 1
- KWGOJCHCWDGJPD-UHFFFAOYSA-N 6-[[amino-[4-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-3-methylanilino]methylidene]amino]hexanoic acid Chemical compound S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2)N=C(N)NCCCCCC(O)=O)C)=C1SC KWGOJCHCWDGJPD-UHFFFAOYSA-N 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 229940017219 methyl propionate Drugs 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- SAWAQEQRAFIORS-UHFFFAOYSA-N n-[2-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-5-(diaminomethylideneamino)-3-methylphenyl]-4-methylsulfonylbutanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(=CC=2C)N=C(N)N)NC(=O)CCCS(C)(=O)=O)=C1SC SAWAQEQRAFIORS-UHFFFAOYSA-N 0.000 claims 1
- BJZFIIHWUDDQQD-UHFFFAOYSA-N n-[amino-[4-[3-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)sulfonylphenyl]-3-methylanilino]methylidene]acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(N)=N)=CC(S(=O)(=O)C=2C=C(C=CC=2)C=2C(=CC(NC(N)=NC(C)=O)=CC=2)C)=C1SC BJZFIIHWUDDQQD-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
Applications Claiming Priority (2)
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|---|---|---|---|
| US38313002P | 2002-05-28 | 2002-05-28 | |
| PCT/US2003/016888 WO2003099805A1 (en) | 2002-05-28 | 2003-05-28 | Novel thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions |
Publications (2)
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| JP2005538953A JP2005538953A (ja) | 2005-12-22 |
| JP2005538953A5 true JP2005538953A5 (https=) | 2006-07-13 |
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| EP (1) | EP1549632A4 (https=) |
| JP (1) | JP2005538953A (https=) |
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| AU (1) | AU2003251384B2 (https=) |
| BR (1) | BR0311419A (https=) |
| CA (1) | CA2484822A1 (https=) |
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| HR (1) | HRP20041220A2 (https=) |
| IL (1) | IL164890A0 (https=) |
| MX (1) | MX249034B (https=) |
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| RU (1) | RU2359967C2 (https=) |
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| US8410277B2 (en) | 2007-12-26 | 2013-04-02 | Eisai R&D Managment Co., Ltd. | Method for manufacturing heterocycle substituted pyridine derivatives |
| PL2315756T3 (pl) | 2008-07-08 | 2015-02-27 | Incyte Holdings Corp | 1,2,5-oksadiazole jako inhibitory 2,3-dioksygenazy indoloaminy |
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| JP6251749B2 (ja) | 2012-09-27 | 2017-12-20 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 置換されていても良いフェニルおよびピリジルピロリジン類の製造方法 |
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| SI3259253T1 (sl) | 2015-02-16 | 2020-07-31 | The University Of Queensland | Sulfonilsečnine in sorodne spojine ter njihova uporaba |
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-
2003
- 2003-05-28 HR HR20041220A patent/HRP20041220A2/hr not_active Application Discontinuation
- 2003-05-28 US US10/445,817 patent/US7109354B2/en not_active Expired - Fee Related
- 2003-05-28 AR ARP030101873A patent/AR039891A1/es unknown
- 2003-05-28 US US10/515,554 patent/US7138530B2/en not_active Expired - Fee Related
- 2003-05-28 ZA ZA200408711A patent/ZA200408711B/en unknown
- 2003-05-28 UA UA20041209867A patent/UA80131C2/uk unknown
- 2003-05-28 WO PCT/US2003/016888 patent/WO2003099805A1/en not_active Ceased
- 2003-05-28 CN CNB038161168A patent/CN100412073C/zh not_active Expired - Fee Related
- 2003-05-28 CA CA002484822A patent/CA2484822A1/en not_active Abandoned
- 2003-05-28 RU RU2004138787/04A patent/RU2359967C2/ru not_active IP Right Cessation
- 2003-05-28 KR KR10-2004-7019227A patent/KR20050009720A/ko not_active Ceased
- 2003-05-28 JP JP2004507462A patent/JP2005538953A/ja active Pending
- 2003-05-28 NZ NZ537346A patent/NZ537346A/en not_active IP Right Cessation
- 2003-05-28 AU AU2003251384A patent/AU2003251384B2/en not_active Ceased
- 2003-05-28 MY MYPI20031975A patent/MY137509A/en unknown
- 2003-05-28 EP EP03755527A patent/EP1549632A4/en not_active Withdrawn
- 2003-05-28 BR BR0311419-8A patent/BR0311419A/pt not_active IP Right Cessation
- 2003-05-28 MX MXPA04011671 patent/MX249034B/es active IP Right Grant
- 2003-05-28 TW TW092114404A patent/TW200406395A/zh unknown
- 2003-05-28 PL PL03372246A patent/PL372246A1/xx not_active Application Discontinuation
-
2004
- 2004-10-17 IL IL16489004A patent/IL164890A0/xx unknown
- 2004-12-10 NO NO20045403A patent/NO20045403L/no not_active Application Discontinuation
- 2004-12-20 CO CO04126948A patent/CO5640081A2/es not_active Application Discontinuation
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