ZA200106849B - Heteroaryl amidines, methylamidines and guanidines as protease inhibitors. - Google Patents

Info

Publication number

ZA200106849B

ZA200106849B ZA200106849A ZA200106849A ZA200106849B ZA 200106849 B ZA200106849 B ZA 200106849B ZA 200106849 A ZA200106849 A ZA 200106849A ZA 200106849 A ZA200106849 A ZA 200106849A ZA 200106849 B ZA200106849 B ZA 200106849B

Authority

ZA

South Africa

Prior art keywords

carboxamidine

amino

methylthiothiophene

methylthio

thiophene

Prior art date

1999-02-09

Links

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• -1 Heteroaryl amidines Chemical class 0.000 title claims description 252
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title description 4
• 150000002357 guanidines Chemical class 0.000 title description 4
• 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 120
• 125000000217 alkyl group Chemical group 0.000 claims description 89
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
• 125000003118 aryl group Chemical group 0.000 claims description 64
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 50
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims description 37
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• 125000003282 alkyl amino group Chemical group 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 31
• 102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims description 30
• 229960005356 urokinase Drugs 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 23
• 102000035195 Peptidases Human genes 0.000 claims description 21
• 108091005804 Peptidases Proteins 0.000 claims description 21
• 125000004104 aryloxy group Chemical group 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000004414 alkyl thio group Chemical group 0.000 claims description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 18
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 108010088842 Fibrinolysin Proteins 0.000 claims description 16
• 125000001769 aryl amino group Chemical group 0.000 claims description 16
• 229940012957 plasmin Drugs 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 239000004365 Protease Substances 0.000 claims description 14
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 239000000651 prodrug Substances 0.000 claims description 13
• 229940002612 prodrug Drugs 0.000 claims description 13
• 125000004442 acylamino group Chemical group 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 206010027476 Metastases Diseases 0.000 claims description 11
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 11
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 230000009401 metastasis Effects 0.000 claims description 11
• LKDMKWNDBAVNQZ-UHFFFAOYSA-N 4-[[1-[[1-[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC(C)C(=O)NC(C)C(=O)N1CCCC1C(=O)NC(C(=O)NC=1C=CC(=CC=1)[N+]([O-])=O)CC1=CC=CC=C1 LKDMKWNDBAVNQZ-UHFFFAOYSA-N 0.000 claims description 10
• 108090000617 Cathepsin G Proteins 0.000 claims description 10
• 108090000317 Chymotrypsin Proteins 0.000 claims description 10
• 206010060862 Prostate cancer Diseases 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 229960002376 chymotrypsin Drugs 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 108090000190 Thrombin Proteins 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
• 210000000265 leukocyte Anatomy 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 8
• 108010067372 Pancreatic elastase Proteins 0.000 claims description 8
• 102000016387 Pancreatic elastase Human genes 0.000 claims description 8
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 108090000631 Trypsin Proteins 0.000 claims description 8
• 102000004142 Trypsin Human genes 0.000 claims description 8
• 230000033115 angiogenesis Effects 0.000 claims description 8
• 125000005239 aroylamino group Chemical group 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 208000037803 restenosis Diseases 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• QSELGEUCFNFITD-UHFFFAOYSA-N thiophene-2-carboximidamide Chemical compound NC(=N)C1=CC=CS1 QSELGEUCFNFITD-UHFFFAOYSA-N 0.000 claims description 8
• 229960004072 thrombin Drugs 0.000 claims description 8
• 239000012588 trypsin Substances 0.000 claims description 8
• 206010014561 Emphysema Diseases 0.000 claims description 7
• 108010074860 Factor Xa Proteins 0.000 claims description 7
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 7
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 7
• 102100033174 Neutrophil elastase Human genes 0.000 claims description 6
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 230000001419 dependent effect Effects 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 229960001322 trypsin Drugs 0.000 claims description 6
• 201000005569 Gout Diseases 0.000 claims description 5
• 108010028275 Leukocyte Elastase Proteins 0.000 claims description 5
• 206010038923 Retinopathy Diseases 0.000 claims description 5
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
• 230000006378 damage Effects 0.000 claims description 5
• 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 108090000107 Acrosin Proteins 0.000 claims description 4
• 102100026041 Acrosin Human genes 0.000 claims description 4
• 108010067641 Complement C3-C5 Convertases Proteins 0.000 claims description 4
• 102000016574 Complement C3-C5 Convertases Human genes 0.000 claims description 4
• 108060005987 Kallikrein Proteins 0.000 claims description 4
• 102000001399 Kallikrein Human genes 0.000 claims description 4
• 206010033645 Pancreatitis Diseases 0.000 claims description 4
• 239000004305 biphenyl Substances 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 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 description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 108010028774 Complement C1 Proteins 0.000 claims description 3
• 102000016917 Complement C1 Human genes 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 3
• 102000057297 Pepsin A Human genes 0.000 claims description 3
• 108090000284 Pepsin A Proteins 0.000 claims description 3
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
• 108090001109 Thermolysin Proteins 0.000 claims description 3
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 3
• 125000004986 diarylamino group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000009826 neoplastic cell growth Effects 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 238000007911 parenteral administration Methods 0.000 claims description 3
• 229940111202 pepsin Drugs 0.000 claims description 3
• 230000029663 wound healing Effects 0.000 claims description 3
• MRKWDSIRHKAISE-BQYQJAHWSA-N (e)-n-(5-carbamimidoyl-2-methylsulfanylthiophen-3-yl)-3-phenylprop-2-enamide Chemical compound S1C(C(N)=N)=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1SC MRKWDSIRHKAISE-BQYQJAHWSA-N 0.000 claims description 2
• QTWSWLPXQSFSQL-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-5-ylamino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C3CCOC3=CC=2)=C1SC QTWSWLPXQSFSQL-UHFFFAOYSA-N 0.000 claims description 2
• TZKHKBSJNUTTPZ-UHFFFAOYSA-N 4-(3-fluoro-4-phenylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(F)C(=CC=2)C=2C=CC=CC=2)=C1SC TZKHKBSJNUTTPZ-UHFFFAOYSA-N 0.000 claims description 2
• URKJMGUACMQENB-UHFFFAOYSA-N 4-(4-chloroanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=CC(Cl)=CC=2)=C1SC URKJMGUACMQENB-UHFFFAOYSA-N 0.000 claims description 2
• QYFIZVJCBMQDSR-UHFFFAOYSA-N 4-(benzenesulfonyl)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1SC QYFIZVJCBMQDSR-UHFFFAOYSA-N 0.000 claims description 2
• GYUNLHSSTCHEKA-UHFFFAOYSA-N 5-methylsulfanyl-4-(3-nitroanilino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(C=CC=2)[N+]([O-])=O)=C1SC GYUNLHSSTCHEKA-UHFFFAOYSA-N 0.000 claims description 2
• QEQXIJSAOGILRW-UHFFFAOYSA-N 5-methylsulfanyl-4-(4-phenylmethoxyanilino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1SC QEQXIJSAOGILRW-UHFFFAOYSA-N 0.000 claims description 2
• VYLPMIZNOYJAPD-UHFFFAOYSA-N 5-methylsulfanyl-4-(naphthalen-1-ylsulfonylamino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=C1SC VYLPMIZNOYJAPD-UHFFFAOYSA-N 0.000 claims description 2
• NGDRPGQBBCJWPB-UHFFFAOYSA-N 5-methylsulfanyl-4-(naphthalen-2-ylamino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C3C=CC=CC3=CC=2)=C1SC NGDRPGQBBCJWPB-UHFFFAOYSA-N 0.000 claims description 2
• BJLYGHBEBNHEJK-UHFFFAOYSA-N 5-methylsulfanyl-4-(quinolin-6-ylamino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C3C=CC=NC3=CC=2)=C1SC BJLYGHBEBNHEJK-UHFFFAOYSA-N 0.000 claims description 2
• 206010063837 Reperfusion injury Diseases 0.000 claims description 2
• 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 2
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
• 125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
• 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 2
• 238000007918 intramuscular administration Methods 0.000 claims description 2
• 238000007912 intraperitoneal administration Methods 0.000 claims description 2
• 238000001990 intravenous administration Methods 0.000 claims description 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
• 238000007920 subcutaneous administration Methods 0.000 claims description 2
• VSEYFSFCFPSWLO-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-5-ylamino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C3CCCC3=CC=2)=C1SC VSEYFSFCFPSWLO-UHFFFAOYSA-N 0.000 claims 2
• 102000004173 Cathepsin G Human genes 0.000 claims 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
• 208000017442 Retinal disease Diseases 0.000 claims 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• DTQDQYGEEZKSIP-UHFFFAOYSA-N 4-(2-methoxyanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound COC1=CC=CC=C1NC1=C(SC)SC(C(N)=N)=C1 DTQDQYGEEZKSIP-UHFFFAOYSA-N 0.000 claims 1
• SRBKKOUPKMSIII-UHFFFAOYSA-N 4-(2-methylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C(=CC=CC=2)C)=C1SC SRBKKOUPKMSIII-UHFFFAOYSA-N 0.000 claims 1
• JUIOWLSPPWHFFF-UHFFFAOYSA-N 4-(3,4-dimethylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(C)C(C)=CC=2)=C1SC JUIOWLSPPWHFFF-UHFFFAOYSA-N 0.000 claims 1
• PXKSAJGGZCEZTA-UHFFFAOYSA-N 4-(3-chloroanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(Cl)C=CC=2)=C1SC PXKSAJGGZCEZTA-UHFFFAOYSA-N 0.000 claims 1
• VPYDDUZUWVGEQU-UHFFFAOYSA-N 4-(3-fluoro-4-methylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(F)C(C)=CC=2)=C1SC VPYDDUZUWVGEQU-UHFFFAOYSA-N 0.000 claims 1
• OTAZQKDXSOLYQM-UHFFFAOYSA-N 4-(3-methoxyanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound COC1=CC=CC(NC2=C(SC(=C2)C(N)=N)SC)=C1 OTAZQKDXSOLYQM-UHFFFAOYSA-N 0.000 claims 1
• AVVPHKPFNDZRHS-UHFFFAOYSA-N 4-(3-methylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(C)C=CC=2)=C1SC AVVPHKPFNDZRHS-UHFFFAOYSA-N 0.000 claims 1
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• AXBSYUUDZIYUJN-UHFFFAOYSA-N 4-(4-cyclohexylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=CC(=CC=2)C2CCCCC2)=C1SC AXBSYUUDZIYUJN-UHFFFAOYSA-N 0.000 claims 1
• JYDLPVRDTCGKSY-UHFFFAOYSA-N 4-(4-ethylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound C1=CC(CC)=CC=C1NC1=C(SC)SC(C(N)=N)=C1 JYDLPVRDTCGKSY-UHFFFAOYSA-N 0.000 claims 1
• NFAIGUBPWLYGOC-UHFFFAOYSA-N 4-(4-methoxyanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound C1=CC(OC)=CC=C1NC1=C(SC)SC(C(N)=N)=C1 NFAIGUBPWLYGOC-UHFFFAOYSA-N 0.000 claims 1
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• VCGYRIKZQIZKTQ-UHFFFAOYSA-N 4-(n-methylanilino)-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(N(C)C=2C=CC=CC=2)=C1SC VCGYRIKZQIZKTQ-UHFFFAOYSA-N 0.000 claims 1
• GPZIUVHBHVGMPS-UHFFFAOYSA-N 4-[(2-chlorophenyl)sulfonylamino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=C1SC GPZIUVHBHVGMPS-UHFFFAOYSA-N 0.000 claims 1
• NYPYHDAEXJLQHD-UHFFFAOYSA-N 4-[(2-methylphenyl)sulfonylamino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NS(=O)(=O)C=2C(=CC=CC=2)C)=C1SC NYPYHDAEXJLQHD-UHFFFAOYSA-N 0.000 claims 1
• RUVCRFPPXVWFMM-UHFFFAOYSA-N 4-[(4-chlorophenyl)sulfonylamino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1SC RUVCRFPPXVWFMM-UHFFFAOYSA-N 0.000 claims 1
• WIYIXQDGDVDQSQ-UHFFFAOYSA-N 4-[(4-methylphenyl)sulfonylamino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NS(=O)(=O)C=2C=CC(C)=CC=2)=C1SC WIYIXQDGDVDQSQ-UHFFFAOYSA-N 0.000 claims 1
• ADXZXWZFGQXOHF-UHFFFAOYSA-N 4-[(9-ethylcarbazol-3-yl)amino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC=1C=C(C(N)=N)SC=1SC ADXZXWZFGQXOHF-UHFFFAOYSA-N 0.000 claims 1
• PBMQYAUDVLEUAK-UHFFFAOYSA-N 4-[[4-hydroxy-4-(trifluoromethyl)-5h-1,3-thiazol-2-yl]amino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2SCC(O)(N=2)C(F)(F)F)=C1SC PBMQYAUDVLEUAK-UHFFFAOYSA-N 0.000 claims 1
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• HSMCANUCHIESPE-UHFFFAOYSA-N 4-[bis(naphthalen-2-ylsulfonyl)amino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=C1SC HSMCANUCHIESPE-UHFFFAOYSA-N 0.000 claims 1
• GYUVUMIGEGSIGB-UHFFFAOYSA-N 4-[bis[(4-phenylphenyl)sulfonyl]amino]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1SC GYUVUMIGEGSIGB-UHFFFAOYSA-N 0.000 claims 1
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
• CBAPNKIEGJESHT-UHFFFAOYSA-N 5-methylsulfanyl-4-(3-phenoxyanilino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(OC=3C=CC=CC=3)C=CC=2)=C1SC CBAPNKIEGJESHT-UHFFFAOYSA-N 0.000 claims 1
• OZKWFVITHFYNOB-UHFFFAOYSA-N 5-methylsulfanyl-4-(3-phenylanilino)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(NC=2C=C(C=CC=2)C=2C=CC=CC=2)=C1SC OZKWFVITHFYNOB-UHFFFAOYSA-N 0.000 claims 1
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