NZ506507A - Heteroaryl amidine, methylamidine or guanidine derivatives useful as urokinase inhibitors - Google Patents

Info

Publication number

NZ506507A

NZ506507A NZ506507A NZ50650799A NZ506507A NZ 506507 A NZ506507 A NZ 506507A NZ 506507 A NZ506507 A NZ 506507A NZ 50650799 A NZ50650799 A NZ 50650799A NZ 506507 A NZ506507 A NZ 506507A

Authority

NZ

New Zealand

Prior art keywords

thiazol

carboxamidine

methylthiothiophene

phenyl

amino

Prior art date

1998-02-09

Links

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• Global Dossier
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• -1 Heteroaryl amidine Chemical class 0.000 title claims abstract description 443
• 239000002797 plasminogen activator inhibitor Substances 0.000 title description 9
• 150000002357 guanidines Chemical class 0.000 title description 7
• 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 211
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 148
• 239000001257 hydrogen Substances 0.000 claims abstract description 92
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 92
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 73
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 65
• 125000003118 aryl group Chemical group 0.000 claims abstract description 62
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 56
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 51
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 48
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 47
• 150000003839 salts Chemical class 0.000 claims abstract description 42
• 150000002367 halogens Chemical group 0.000 claims abstract description 39
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 38
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
• 125000000266 alpha-aminoacyl group Chemical group 0.000 claims abstract description 25
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims abstract description 25
• 125000005110 aryl thio group Chemical group 0.000 claims abstract description 25
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 25
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
• 239000012453 solvate Substances 0.000 claims abstract description 23
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 17
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 17
• 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims abstract description 15
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
• 206010027476 Metastases Diseases 0.000 claims abstract description 11
• 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 11
• 230000009401 metastasis Effects 0.000 claims abstract description 11
• 206010060862 Prostate cancer Diseases 0.000 claims abstract description 9
• 125000002252 acyl group Chemical group 0.000 claims abstract description 9
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims abstract description 8
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims abstract description 8
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 8
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 8
• 208000037803 restenosis Diseases 0.000 claims abstract description 8
• 206010014561 Emphysema Diseases 0.000 claims abstract description 7
• 125000006501 nitrophenyl group Chemical group 0.000 claims abstract description 7
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims abstract description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
• 206010033645 Pancreatitis Diseases 0.000 claims abstract description 4
• 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 4
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims abstract description 4
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims abstract description 4
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims abstract description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 4
• 125000003441 thioacyl group Chemical group 0.000 claims abstract description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 3
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 3
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims abstract description 3
• 230000009826 neoplastic cell growth Effects 0.000 claims abstract description 3
• 230000029663 wound healing Effects 0.000 claims abstract description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 14
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 188
• 235000011468 Albizia julibrissin Nutrition 0.000 claims description 116
• 241001070944 Mimosa Species 0.000 claims description 116
• 230000015572 biosynthetic process Effects 0.000 claims description 103
• 239000007787 solid Substances 0.000 claims description 66
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 238000010992 reflux Methods 0.000 claims description 57
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 54
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 47
• 125000003282 alkyl amino group Chemical group 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 44
• 239000000203 mixture Substances 0.000 claims description 35
• 108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims description 32
• 150000002148 esters Chemical class 0.000 claims description 32
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 239000003814 drug Substances 0.000 claims description 30
• 229960005356 urokinase Drugs 0.000 claims description 27
• 102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims description 26
• 238000003756 stirring Methods 0.000 claims description 26
• 125000000335 thiazolyl group Chemical group 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 125000004442 acylamino group Chemical group 0.000 claims description 23
• 235000019270 ammonium chloride Nutrition 0.000 claims description 23
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 239000000725 suspension Substances 0.000 claims description 22
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
• 102000035195 Peptidases Human genes 0.000 claims description 20
• 108091005804 Peptidases Proteins 0.000 claims description 20
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 20
• 125000001544 thienyl group Chemical group 0.000 claims description 20
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
• 125000002971 oxazolyl group Chemical group 0.000 claims description 19
• QSELGEUCFNFITD-UHFFFAOYSA-N thiophene-2-carboximidamide Chemical compound NC(=N)C1=CC=CS1 QSELGEUCFNFITD-UHFFFAOYSA-N 0.000 claims description 19
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 18
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 16
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 16
• 125000001769 aryl amino group Chemical group 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 108010088842 Fibrinolysin Proteins 0.000 claims description 14
• 239000004365 Protease Substances 0.000 claims description 14
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 229940012957 plasmin Drugs 0.000 claims description 14
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 13
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 230000017854 proteolysis Effects 0.000 claims description 11
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
• 239000007789 gas Substances 0.000 claims description 10
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 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 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 108090000617 Cathepsin G Proteins 0.000 claims description 9
• 239000002841 Lewis acid Substances 0.000 claims description 9
• 230000033115 angiogenesis Effects 0.000 claims description 9
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 150000007517 lewis acids Chemical class 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 108090000317 Chymotrypsin Proteins 0.000 claims description 8
• 108090000190 Thrombin Proteins 0.000 claims description 8
• 229960002376 chymotrypsin Drugs 0.000 claims description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 210000000265 leukocyte Anatomy 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 7
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 7
• 108010067372 Pancreatic elastase Proteins 0.000 claims description 7
• 102000016387 Pancreatic elastase Human genes 0.000 claims description 7
• 210000002744 extracellular matrix Anatomy 0.000 claims description 7
• 238000010438 heat treatment Methods 0.000 claims description 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
• 125000005968 oxazolinyl group Chemical group 0.000 claims description 7
• 239000000651 prodrug Substances 0.000 claims description 7
• 229940002612 prodrug Drugs 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 229960004072 thrombin Drugs 0.000 claims description 7
• OMMIMDGHTTXEFT-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1SC OMMIMDGHTTXEFT-UHFFFAOYSA-N 0.000 claims description 6
• 108010074860 Factor Xa Proteins 0.000 claims description 6
• 108090000631 Trypsin Proteins 0.000 claims description 6
• 102000004142 Trypsin Human genes 0.000 claims description 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 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
• 201000011510 cancer Diseases 0.000 claims description 6
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
• 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 239000012588 trypsin Substances 0.000 claims description 6
• 102100033174 Neutrophil elastase Human genes 0.000 claims description 5
• 206010038923 Retinopathy Diseases 0.000 claims description 5
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 5
• 229960001322 trypsin Drugs 0.000 claims description 5
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
• WHGZPVSQCGFYBQ-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C(=CC(Cl)=CC=2)Cl)=C1SC WHGZPVSQCGFYBQ-UHFFFAOYSA-N 0.000 claims description 4
• GARVNVZOSLSGOA-UHFFFAOYSA-N 4-[4-(2-chloropyridin-3-yl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C(=NC=CC=2)Cl)=C1SC GARVNVZOSLSGOA-UHFFFAOYSA-N 0.000 claims description 4
• KLVFDMVKNCAXRG-UHFFFAOYSA-N 4-[4-(3-hydroxyphenyl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=C(O)C=CC=2)=C1SC KLVFDMVKNCAXRG-UHFFFAOYSA-N 0.000 claims description 4
• UZGWXXYKZGJHJY-UHFFFAOYSA-N 5-methylsulfanyl-4-(4-methyl-1,3-thiazol-2-yl)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(C)N=2)=C1SC UZGWXXYKZGJHJY-UHFFFAOYSA-N 0.000 claims description 4
• CKYREKXNBZFCFF-UHFFFAOYSA-N 5-methylsulfanyl-4-(4-naphthalen-2-yl-1,3-thiazol-2-yl)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=C3C=CC=CC3=CC=2)=C1SC CKYREKXNBZFCFF-UHFFFAOYSA-N 0.000 claims description 4
• NPTFSUUZGYDTPV-UHFFFAOYSA-N 5-methylsulfanyl-4-phenylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2C=CC=CC=2)=C1SC NPTFSUUZGYDTPV-UHFFFAOYSA-N 0.000 claims description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
• 108010073385 Fibrin Proteins 0.000 claims description 4
• 102000009123 Fibrin Human genes 0.000 claims description 4
• BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 4
• 201000005569 Gout Diseases 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 108010028275 Leukocyte Elastase Proteins 0.000 claims description 4
• 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 4
• 125000003368 amide group Chemical group 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• 239000012298 atmosphere Substances 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 239000004305 biphenyl Substances 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 230000010261 cell growth Effects 0.000 claims description 4
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 4
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
• 229950003499 fibrin Drugs 0.000 claims description 4
• 238000009472 formulation Methods 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• SVVUBLUORZHCSW-UHFFFAOYSA-N n'-amino-5-methylsulfanyl-4-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboximidamide Chemical compound S1C(C(=N)NN)=CC(C=2SC=C(N=2)C=2C=CC=CC=2)=C1SC SVVUBLUORZHCSW-UHFFFAOYSA-N 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• HNTSNHYPGXXIFN-UHFFFAOYSA-N 4-[2-(2,3-dichloroanilino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(NC=3C(=C(Cl)C=CC=3)Cl)SC=2)=C1SC HNTSNHYPGXXIFN-UHFFFAOYSA-N 0.000 claims description 3
• ZUWAYNCFFNVIBJ-UHFFFAOYSA-N 4-[2-(2-fluoroanilino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(NC=3C(=CC=CC=3)F)SC=2)=C1SC ZUWAYNCFFNVIBJ-UHFFFAOYSA-N 0.000 claims description 3
• LIRPGSNQMOFUBQ-UHFFFAOYSA-N 4-[2-(3-chloro-2-methylanilino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(NC=3C(=C(Cl)C=CC=3)C)SC=2)=C1SC LIRPGSNQMOFUBQ-UHFFFAOYSA-N 0.000 claims description 3
• FDRDCAYYXVHESU-UHFFFAOYSA-N 4-[2-(3-methoxyanilino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound COC1=CC=CC(NC=2SC=C(N=2)C2=C(SC(=C2)C(N)=N)SC)=C1 FDRDCAYYXVHESU-UHFFFAOYSA-N 0.000 claims description 3
• KSJUFIPSZGIVLF-UHFFFAOYSA-N 4-[2-(4-chloro-2-methylanilino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(NC=3C(=CC(Cl)=CC=3)C)SC=2)=C1SC KSJUFIPSZGIVLF-UHFFFAOYSA-N 0.000 claims description 3
• QJRTVZFPEDJWOS-UHFFFAOYSA-N 4-[2-(4-methoxyanilino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound C1=CC(OC)=CC=C1NC1=NC(C2=C(SC(=C2)C(N)=N)SC)=CS1 QJRTVZFPEDJWOS-UHFFFAOYSA-N 0.000 claims description 3
• ABEISAYFSWNEFB-UHFFFAOYSA-N 4-[2-(benzhydrylamino)-1,3-thiazol-4-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(NC(C=3C=CC=CC=3)C=3C=CC=CC=3)SC=2)=C1SC ABEISAYFSWNEFB-UHFFFAOYSA-N 0.000 claims description 3
• IQHIAMAAHJGYDK-UHFFFAOYSA-N 4-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=C3OCCOC3=CC=2)=C1SC IQHIAMAAHJGYDK-UHFFFAOYSA-N 0.000 claims description 3
• HFUGBKCICWUZIJ-UHFFFAOYSA-N 4-[4-(3-methoxyphenyl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound COC1=CC=CC(C=2N=C(SC=2)C2=C(SC(=C2)C(N)=N)SC)=C1 HFUGBKCICWUZIJ-UHFFFAOYSA-N 0.000 claims description 3
• QCNAOMPLQHHHTO-UHFFFAOYSA-N 4-[4-(4-chloro-3-methylphenyl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=C(C)C(Cl)=CC=2)=C1SC QCNAOMPLQHHHTO-UHFFFAOYSA-N 0.000 claims description 3
• IOEIVKCJGQEFIB-UHFFFAOYSA-N 4-phenyl-5-(trifluoromethyl)thiophene-2-carboximidamide Chemical compound S1C(C(=N)N)=CC(C=2C=CC=CC=2)=C1C(F)(F)F IOEIVKCJGQEFIB-UHFFFAOYSA-N 0.000 claims description 3
• CABMYWJUHPNDIO-UHFFFAOYSA-N 5-methylsulfanyl-4-(3-phenylphenyl)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1SC CABMYWJUHPNDIO-UHFFFAOYSA-N 0.000 claims description 3
• QJBLOXHRGXCQHF-UHFFFAOYSA-N 5-methylsulfanyl-4-(6-phenylpyridin-2-yl)thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(C=CC=2)C=2C=CC=CC=2)=C1SC QJBLOXHRGXCQHF-UHFFFAOYSA-N 0.000 claims description 3
• YCMAPLMAEQZHAF-UHFFFAOYSA-N 5-methylsulfanyl-4-[2-(2,4,5-trimethylanilino)-1,3-thiazol-4-yl]thiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2N=C(NC=3C(=CC(C)=C(C)C=3)C)SC=2)=C1SC YCMAPLMAEQZHAF-UHFFFAOYSA-N 0.000 claims description 3
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