CA2657107C - Human protein tyrosine phosphatase inhibitors and methods of use - Google Patents

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Publication number

CA2657107C

CA2657107C CA2657107A CA2657107A CA2657107C CA 2657107 C CA2657107 C CA 2657107C CA 2657107 A CA2657107 A CA 2657107A CA 2657107 A CA2657107 A CA 2657107A CA 2657107 C CA2657107 C CA 2657107C

Authority

CA

Canada

Prior art keywords

ethyl

substituted

phenyl

thiazol

compound according

Prior art date

2006-06-27

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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• 238000000034 method Methods 0.000 title claims abstract description 72
• 239000003806 protein tyrosine phosphatase inhibitor Substances 0.000 title description 2
• 102000003839 Human Proteins Human genes 0.000 title 1
• 108090000144 Human Proteins Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 182
• 230000033115 angiogenesis Effects 0.000 claims abstract description 79
• 239000000203 mixture Substances 0.000 claims abstract description 74
• 230000001105 regulatory effect Effects 0.000 claims abstract description 33
• -1 1,2,3,4-tetrazol-1-yl Chemical group 0.000 claims description 440
• 229910052739 hydrogen Inorganic materials 0.000 claims description 234
• 239000001257 hydrogen Substances 0.000 claims description 232
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 204
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 202
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 156
• 150000002431 hydrogen Chemical class 0.000 claims description 132
• 125000001072 heteroaryl group Chemical group 0.000 claims description 92
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 78
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 63
• BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 claims description 51
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 49
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
• 210000001519 tissue Anatomy 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 41
• 201000010099 disease Diseases 0.000 claims description 36
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 34
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 33
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 31
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 31
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 24
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 239000007787 solid Substances 0.000 claims description 23
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 23
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 19
• 238000006467 substitution reaction Methods 0.000 claims description 19
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• 125000004429 atom Chemical group 0.000 claims description 17
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 17
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 16
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 16
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 16
• 230000017423 tissue regeneration Effects 0.000 claims description 16
• 230000012010 growth Effects 0.000 claims description 15
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 15
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 14
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 12
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 11
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
• 208000031953 Hereditary hemorrhagic telangiectasia Diseases 0.000 claims description 10
• 208000029078 coronary artery disease Diseases 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 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 9
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 9
• 230000001684 chronic effect Effects 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 201000000306 sarcoidosis Diseases 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 206010046851 Uveitis Diseases 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 8
• 208000014674 injury Diseases 0.000 claims description 8
• 230000000302 ischemic effect Effects 0.000 claims description 8
• 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 claims description 8
• 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 8
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 8
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 8
• 230000001737 promoting effect Effects 0.000 claims description 8
• 210000001367 artery Anatomy 0.000 claims description 7
• 239000008280 blood Substances 0.000 claims description 7
• 210000004369 blood Anatomy 0.000 claims description 7
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 7
• 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 claims description 7
• 239000011575 calcium Substances 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 210000002027 skeletal muscle Anatomy 0.000 claims description 6
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• 208000030507 AIDS Diseases 0.000 claims description 5
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
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• 208000031225 myocardial ischemia Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• 102100028187 ATP-binding cassette sub-family C member 6 Human genes 0.000 claims description 4
• 208000009137 Behcet syndrome Diseases 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 208000016974 Eales' disease Diseases 0.000 claims description 4
• 201000002563 Histoplasmosis Diseases 0.000 claims description 4
• 206010051151 Hyperviscosity syndrome Diseases 0.000 claims description 4
• 208000016604 Lyme disease Diseases 0.000 claims description 4
• 206010025412 Macular dystrophy congenital Diseases 0.000 claims description 4
• 206010062207 Mycobacterial infection Diseases 0.000 claims description 4
• 208000010191 Osteitis Deformans Diseases 0.000 claims description 4
• 208000027868 Paget disease Diseases 0.000 claims description 4
• 208000004788 Pars Planitis Diseases 0.000 claims description 4
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
• 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims description 4
• 201000004613 Pseudoxanthoma elasticum Diseases 0.000 claims description 4
• 206010038848 Retinal detachment Diseases 0.000 claims description 4
• 206010038910 Retinitis Diseases 0.000 claims description 4
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 4
• 206010038934 Retinopathy proliferative Diseases 0.000 claims description 4
• 208000027073 Stargardt disease Diseases 0.000 claims description 4
• 201000005485 Toxoplasmosis Diseases 0.000 claims description 4
• 206010047663 Vitritis Diseases 0.000 claims description 4
• VIYUQCGNYBLDBS-IBGZPJMESA-N [4-[(2s)-2-(benzylcarbamoylamino)-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)NCC=2C=CC=CC=2)=N1 VIYUQCGNYBLDBS-IBGZPJMESA-N 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 208000013653 hyalitis Diseases 0.000 claims description 4
• 208000002780 macular degeneration Diseases 0.000 claims description 4
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• 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims description 4
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• 230000006785 proliferative vitreoretinopathy Effects 0.000 claims description 4
• 208000023558 pseudoxanthoma elasticum (inherited or acquired) Diseases 0.000 claims description 4
• 230000004264 retinal detachment Effects 0.000 claims description 4
• 208000007056 sickle cell anemia Diseases 0.000 claims description 4
• 239000011734 sodium Substances 0.000 claims description 4
• 208000006379 syphilis Diseases 0.000 claims description 4
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
• 210000003462 vein Anatomy 0.000 claims description 4
• 201000007790 vitelliform macular dystrophy Diseases 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
• 208000002691 Choroiditis Diseases 0.000 claims description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
• 208000003971 Posterior uveitis Diseases 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
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• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
• 229910019142 PO4 Inorganic materials 0.000 claims description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
• SOPFMLSUZYXTGB-AWEZNQCLSA-N [4-[(2s)-2-(2-ethyl-1,3-thiazol-4-yl)-2-[[4-[(2-methoxy-2-oxoethyl)carbamoyl]-1,3-thiazol-5-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound S1C(CC)=NC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC2=C(N=CS2)C(=O)NCC(=O)OC)=C1 SOPFMLSUZYXTGB-AWEZNQCLSA-N 0.000 claims description 2
• OYRLZGKRUDDGED-SFHVURJKSA-N [4-[(2s)-2-[[2-(2,3-difluorophenyl)acetyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C(=C(F)C=CC=2)F)=N1 OYRLZGKRUDDGED-SFHVURJKSA-N 0.000 claims description 2
• PEDLPKOPLGMCPC-FQEVSTJZSA-N [4-[(2s)-2-[[2-(3-methoxyphenyl)acetyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound COC1=CC=CC(CC(=O)N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C=2SC=CC=2)=C1 PEDLPKOPLGMCPC-FQEVSTJZSA-N 0.000 claims description 2
• JXQKQZIDKIUAQE-SFHVURJKSA-N [4-[(2s)-2-[[5-(2-methoxyphenyl)-1,3-oxazol-2-yl]amino]-2-(2-methyl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound COC1=CC=CC=C1C(O1)=CN=C1N[C@H](C=1N=C(C)SC=1)CC1=CC=C(NS(O)(=O)=O)C=C1 JXQKQZIDKIUAQE-SFHVURJKSA-N 0.000 claims description 2
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• OCOKWTQISJIFFE-FQEVSTJZSA-N [4-[(2s)-2-(2-cyclopropyl-1,3-thiazol-4-yl)-2-[[4-(3-methoxyphenyl)-1,3-thiazol-2-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound COC1=CC=CC(C=2N=C(N[C@@H](CC=3C=CC(NS(O)(=O)=O)=CC=3)C=3N=C(SC=3)C3CC3)SC=2)=C1 OCOKWTQISJIFFE-FQEVSTJZSA-N 0.000 claims 2
• FDLJNJWNVFUJKM-UHFFFAOYSA-N 2-(2,4-dimethyl-1,3-thiazol-5-yl)acetamide Chemical compound CC1=NC(C)=C(CC(N)=O)S1 FDLJNJWNVFUJKM-UHFFFAOYSA-N 0.000 claims 1
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• WAXKQVZCJRJMFJ-UHFFFAOYSA-N 2-(3-methyl-1,2,4-oxadiazol-5-yl)acetamide Chemical compound CC1=NOC(CC(N)=O)=N1 WAXKQVZCJRJMFJ-UHFFFAOYSA-N 0.000 claims 1
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
• RGFRRSOWKXIOLI-AMVUTOCUSA-N [4-[(2s)-2-(2,3-diphenylpropanoylamino)-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)C(CC=2C=CC=CC=2)C=2C=CC=CC=2)=N1 RGFRRSOWKXIOLI-AMVUTOCUSA-N 0.000 claims 1
• MTPVUXQTHJPPLV-IBGZPJMESA-N [4-[(2s)-2-(2-cyclopropyl-1,3-thiazol-4-yl)-2-[[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C1CC1)NC1=NC(C=2C(=CC(F)=CC=2)F)=CS1 MTPVUXQTHJPPLV-IBGZPJMESA-N 0.000 claims 1
• KAAQQKVWLKFFHB-IBGZPJMESA-N [4-[(2s)-2-(2-cyclopropyl-1,3-thiazol-4-yl)-2-[[4-(2-methoxyphenyl)-1,3-thiazol-2-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound COC1=CC=CC=C1C1=CSC(N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C2CC2)=N1 KAAQQKVWLKFFHB-IBGZPJMESA-N 0.000 claims 1
• PGAJAZQWFRIXKK-IBGZPJMESA-N [4-[(2s)-2-(2-cyclopropyl-1,3-thiazol-4-yl)-2-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C1CC1)NC1=NC(C=2C=CC(F)=CC=2)=CS1 PGAJAZQWFRIXKK-IBGZPJMESA-N 0.000 claims 1
• VZXKRKOTZBSHIZ-QFIPXVFZSA-N [4-[(2s)-2-(2-cyclopropyl-1,3-thiazol-4-yl)-2-[[4-[(3-methoxyphenyl)methyl]-1,3-thiazol-2-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound COC1=CC=CC(CC=2N=C(N[C@@H](CC=3C=CC(NS(O)(=O)=O)=CC=3)C=3N=C(SC=3)C3CC3)SC=2)=C1 VZXKRKOTZBSHIZ-QFIPXVFZSA-N 0.000 claims 1
• JDQZZSFRQXEIAN-AWEZNQCLSA-N [4-[(2s)-2-(2-ethyl-1,3-thiazol-4-yl)-2-[(1-methylimidazol-4-yl)sulfonylamino]ethyl]phenyl]sulfamic acid Chemical compound S1C(CC)=NC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NS(=O)(=O)C=2N=CN(C)C=2)=C1 JDQZZSFRQXEIAN-AWEZNQCLSA-N 0.000 claims 1
• BZWXLZQQSYELIZ-IBGZPJMESA-N [4-[(2s)-2-(2-ethyl-1,3-thiazol-4-yl)-2-[(4-methoxycarbonylphenyl)methylsulfonylamino]ethyl]phenyl]sulfamic acid Chemical compound S1C(CC)=NC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NS(=O)(=O)CC=2C=CC(=CC=2)C(=O)OC)=C1 BZWXLZQQSYELIZ-IBGZPJMESA-N 0.000 claims 1
• SDYIWVDHUFVKGU-ZDUSSCGKSA-N [4-[(2s)-2-(2-ethyl-1,3-thiazol-4-yl)-2-[[5-(methoxycarbonylamino)-1-methyl-1,2,4-triazol-3-yl]amino]ethyl]phenyl]sulfamic acid Chemical compound S1C(CC)=NC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC2=NN(C)C(NC(=O)OC)=N2)=C1 SDYIWVDHUFVKGU-ZDUSSCGKSA-N 0.000 claims 1
• RZKKDVFBXQXZTE-SFHVURJKSA-N [4-[(2s)-2-(2-methyl-1,3-thiazol-4-yl)-2-[(5-phenyl-1,3-oxazol-2-yl)amino]ethyl]phenyl]sulfamic acid Chemical compound S1C(C)=NC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC=2OC(=CN=2)C=2C=CC=CC=2)=C1 RZKKDVFBXQXZTE-SFHVURJKSA-N 0.000 claims 1
• NJSLTICVKXPNGT-QFIPXVFZSA-N [4-[(2s)-2-(2-phenyl-1,3-thiazol-4-yl)-2-[(4-phenyl-1,3-thiazol-2-yl)amino]ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C=1C=CC=CC=1)NC1=NC(C=2C=CC=CC=2)=CS1 NJSLTICVKXPNGT-QFIPXVFZSA-N 0.000 claims 1
• AHCRDMDVIAESCO-ZDUSSCGKSA-N [4-[(2s)-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)-2-(2,2,2-trifluoroethylsulfonylamino)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@H](NS(=O)(=O)CC(F)(F)F)C1=CSC(C=2SC=CC=2)=N1 AHCRDMDVIAESCO-ZDUSSCGKSA-N 0.000 claims 1
• CXVLJDZUNHLZTF-FQEVSTJZSA-N [4-[(2s)-2-(3-phenylpropanoylamino)-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C=1SC=CC=1)NC(=O)CCC1=CC=CC=C1 CXVLJDZUNHLZTF-FQEVSTJZSA-N 0.000 claims 1
• UIAZWGVZVAATRB-FQEVSTJZSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-(3-phenylpropanoylamino)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC=2C=CC=CC=2)=N1 UIAZWGVZVAATRB-FQEVSTJZSA-N 0.000 claims 1
• HTPBIOVOBBRRHY-FQEVSTJZSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[(4-oxo-4-phenylbutanoyl)amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC(=O)C=2C=CC=CC=2)=N1 HTPBIOVOBBRRHY-FQEVSTJZSA-N 0.000 claims 1
• LNRHTQGXFDEXCU-IBGZPJMESA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[(4-oxo-4-pyridin-2-ylbutanoyl)amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC(=O)C=2N=CC=CC=2)=N1 LNRHTQGXFDEXCU-IBGZPJMESA-N 0.000 claims 1
• FTVNMKDJBOHXJD-KRWDZBQOSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[(5-methyl-4-oxohexanoyl)amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC(=O)C(C)C)=N1 FTVNMKDJBOHXJD-KRWDZBQOSA-N 0.000 claims 1
• DPISVJDMXSOTLO-INIZCTEOSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[3-(1,3-thiazol-2-yl)propanoylamino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC=2SC=CN=2)=N1 DPISVJDMXSOTLO-INIZCTEOSA-N 0.000 claims 1
• INUIUGLCVCUBPQ-FQEVSTJZSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[3-(2-methoxyphenyl)propanoylamino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC=2C(=CC=CC=2)OC)=N1 INUIUGLCVCUBPQ-FQEVSTJZSA-N 0.000 claims 1
• GBLHRFSKNLGKOI-NRFANRHFSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[3-(3-methoxyphenyl)propanoylamino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC=2C=C(OC)C=CC=2)=N1 GBLHRFSKNLGKOI-NRFANRHFSA-N 0.000 claims 1
• ZKHCEGCYHCMNNC-NRFANRHFSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[3-(4-methoxyphenyl)propanoylamino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC=2C=CC(OC)=CC=2)=N1 ZKHCEGCYHCMNNC-NRFANRHFSA-N 0.000 claims 1
• XUJJNTYWZAVJHS-IBGZPJMESA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(2-fluorophenyl)acetyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C(=CC=CC=2)F)=N1 XUJJNTYWZAVJHS-IBGZPJMESA-N 0.000 claims 1
• CSGSBSHXLABUFG-AMVUTOCUSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(2-methoxyphenyl)-3-phenylpropanoyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)C(CC=2C=CC=CC=2)C=2C(=CC=CC=2)OC)=N1 CSGSBSHXLABUFG-AMVUTOCUSA-N 0.000 claims 1
• FZLZQVMBGLZHJE-IBGZPJMESA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(2-methoxyphenyl)acetyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C(=CC=CC=2)OC)=N1 FZLZQVMBGLZHJE-IBGZPJMESA-N 0.000 claims 1
• UGDACKDRXGUMIE-AMVUTOCUSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(3-fluorophenyl)-3-phenylpropanoyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)C(CC=2C=CC=CC=2)C=2C=C(F)C=CC=2)=N1 UGDACKDRXGUMIE-AMVUTOCUSA-N 0.000 claims 1
• OWQRDPCPQKJXGQ-IBGZPJMESA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(3-fluorophenyl)acetyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C=C(F)C=CC=2)=N1 OWQRDPCPQKJXGQ-IBGZPJMESA-N 0.000 claims 1
• VUBRJZVWXOODGV-IBGZPJMESA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(3-hydroxyphenyl)acetyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C=C(O)C=CC=2)=N1 VUBRJZVWXOODGV-IBGZPJMESA-N 0.000 claims 1
• UWXTZGOAPALKPA-GEVKEYJPSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(3-methoxyphenyl)-3-phenylpropanoyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)C(CC=2C=CC=CC=2)C=2C=C(OC)C=CC=2)=N1 UWXTZGOAPALKPA-GEVKEYJPSA-N 0.000 claims 1
• RCKIITSHDNZSIP-FQEVSTJZSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(3-methoxyphenyl)acetyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C=C(OC)C=CC=2)=N1 RCKIITSHDNZSIP-FQEVSTJZSA-N 0.000 claims 1
• LJVOECHBYHMFNG-KEKNWZKVSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenylpropanoyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)C(CC=2C=CC=CC=2)C=2ON=C(C)N=2)=N1 LJVOECHBYHMFNG-KEKNWZKVSA-N 0.000 claims 1
• LJYGCZBQGVHPQD-KRWDZBQOSA-N [4-[(2s)-2-(4-ethyl-1,3-thiazol-2-yl)-2-[[4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC(=O)OC(C)(C)C)=N1 LJYGCZBQGVHPQD-KRWDZBQOSA-N 0.000 claims 1
• JRSUKSWTUCRNEX-IBGZPJMESA-N [4-[(2s)-2-(benzylcarbamoylamino)-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C=1SC=CC=1)NC(=O)NCC1=CC=CC=C1 JRSUKSWTUCRNEX-IBGZPJMESA-N 0.000 claims 1
• JQRZASYIJJKHSD-KRWDZBQOSA-N [4-[(2s)-2-[(2-methyl-1,3-thiazol-4-yl)methylsulfonylamino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound S1C(C)=NC(CS(=O)(=O)N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C=2SC=CC=2)=C1 JQRZASYIJJKHSD-KRWDZBQOSA-N 0.000 claims 1
• OMRMEYUBCDJARQ-FQEVSTJZSA-N [4-[(2s)-2-[(4-acetamidophenyl)sulfonylamino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)N[C@H](C=1N=C(SC=1)C=1SC=CC=1)CC1=CC=C(NS(O)(=O)=O)C=C1 OMRMEYUBCDJARQ-FQEVSTJZSA-N 0.000 claims 1
• TYRWQYRBFXZGRH-INIZCTEOSA-N [4-[(2s)-2-[(4-ethoxy-4-oxobutanoyl)amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound C([C@H](NC(=O)CCC(=O)OCC)C=1SC=C(CC)N=1)C1=CC=C(NS(O)(=O)=O)C=C1 TYRWQYRBFXZGRH-INIZCTEOSA-N 0.000 claims 1
• UPCSBXDKHHXFFM-SFHVURJKSA-N [4-[(2s)-2-[(4-ethoxycarbonyl-1,3-thiazol-2-yl)amino]-2-(2-phenyl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound CCOC(=O)C1=CSC(N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C=2C=CC=CC=2)=N1 UPCSBXDKHHXFFM-SFHVURJKSA-N 0.000 claims 1
• WRKKLLDUNAVQMR-HNNXBMFYSA-N [4-[(2s)-2-[(4-ethoxycarbonyl-1,3-thiazol-2-yl)amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound CCOC(=O)C1=CSC(N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C=2SC=CC=2)=N1 WRKKLLDUNAVQMR-HNNXBMFYSA-N 0.000 claims 1
• HDNKEDKQVAHIKV-KRWDZBQOSA-N [4-[(2s)-2-[(4-methoxycarbonyl-1,3-thiazol-5-yl)amino]-2-(2-phenyl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound N1=CSC(N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C=2C=CC=CC=2)=C1C(=O)OC HDNKEDKQVAHIKV-KRWDZBQOSA-N 0.000 claims 1
• BVXOVRYBMVNXNO-IBGZPJMESA-N [4-[(2s)-2-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfonylamino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C([C@H](NS(=O)(=O)C=1C=C2OCCN(C2=CC=1)C)C=1N=C(SC=1)C=1SC=CC=1)C1=CC=C(NS(O)(=O)=O)C=C1 BVXOVRYBMVNXNO-IBGZPJMESA-N 0.000 claims 1
• ULRGLQXEKCSVMQ-AWEZNQCLSA-N [4-[(2s)-2-[(6-methyl-4-oxo-1h-pyrimidin-2-yl)amino]-2-(2-methyl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound S1C(C)=NC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC=2N=C(O)C=C(C)N=2)=C1 ULRGLQXEKCSVMQ-AWEZNQCLSA-N 0.000 claims 1
• OAXJUUOBPQKZHJ-FQEVSTJZSA-N [4-[(2s)-2-[3-(3-chlorophenyl)propanoylamino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C=1SC=CC=1)NC(=O)CCC1=CC=CC(Cl)=C1 OAXJUUOBPQKZHJ-FQEVSTJZSA-N 0.000 claims 1
• STTNVVHPOLOFHV-FQEVSTJZSA-N [4-[(2s)-2-[3-(3-chlorophenyl)propanoylamino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC=2C=C(Cl)C=CC=2)=N1 STTNVVHPOLOFHV-FQEVSTJZSA-N 0.000 claims 1
• OMEARSOPYMXZCH-IBGZPJMESA-N [4-[(2s)-2-[[2-(2,3-dimethoxyphenyl)acetyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C(=C(OC)C=CC=2)OC)=N1 OMEARSOPYMXZCH-IBGZPJMESA-N 0.000 claims 1
• RXNNYAMSKLUJSV-IBGZPJMESA-N [4-[(2s)-2-[[2-(2-chlorophenyl)acetyl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C=1SC=CC=1)NC(=O)CC1=CC=CC=C1Cl RXNNYAMSKLUJSV-IBGZPJMESA-N 0.000 claims 1
• VLWFEBRQUXEKDY-IBGZPJMESA-N [4-[(2s)-2-[[2-(2-chlorophenyl)acetyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C(=CC=CC=2)Cl)=N1 VLWFEBRQUXEKDY-IBGZPJMESA-N 0.000 claims 1
• AGKCTKMOEMXUNB-IBGZPJMESA-N [4-[(2s)-2-[[2-(3,4-difluorophenyl)acetyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C=C(F)C(F)=CC=2)=N1 AGKCTKMOEMXUNB-IBGZPJMESA-N 0.000 claims 1
• UMEVMMJAIZFKAX-IBGZPJMESA-N [4-[(2s)-2-[[2-(3,4-dimethoxyphenyl)acetyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C=C(OC)C(OC)=CC=2)=N1 UMEVMMJAIZFKAX-IBGZPJMESA-N 0.000 claims 1
• CFBAFWZBQFEGBW-IBGZPJMESA-N [4-[(2s)-2-[[2-(3-chlorophenyl)acetyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CC=2C=C(Cl)C=CC=2)=N1 CFBAFWZBQFEGBW-IBGZPJMESA-N 0.000 claims 1
• YHKHPIGWVBNMPO-FQEVSTJZSA-N [4-[(2s)-2-[[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-oxobutanoyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC(=O)C=2C=C3OCCOC3=CC=2)=N1 YHKHPIGWVBNMPO-FQEVSTJZSA-N 0.000 claims 1
• FFYRKUNZJVNFMA-FQEVSTJZSA-N [4-[(2s)-2-[[4-(2,3-dimethoxyphenyl)-4-oxobutanoyl]amino]-2-(4-ethyl-1,3-thiazol-2-yl)ethyl]phenyl]sulfamic acid Chemical compound CCC1=CSC([C@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)NC(=O)CCC(=O)C=2C(=C(OC)C=CC=2)OC)=N1 FFYRKUNZJVNFMA-FQEVSTJZSA-N 0.000 claims 1
• MWCHDRNCGYRZOV-IBGZPJMESA-N [4-[(2s)-2-[[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]amino]-2-(2-thiophen-2-yl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound C1=CC(NS(=O)(=O)O)=CC=C1C[C@@H](C=1N=C(SC=1)C=1SC=CC=1)NC1=NC(C=2C(=CC(F)=CC=2)F)=CS1 MWCHDRNCGYRZOV-IBGZPJMESA-N 0.000 claims 1
• SXEJIWMUFRXLJZ-FQEVSTJZSA-N [4-[(2s)-2-[[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]amino]-2-(2-phenyl-1,3-thiazol-4-yl)ethyl]phenyl]sulfamic acid Chemical compound CCOC(=O)CC1=CSC(N[C@@H](CC=2C=CC(NS(O)(=O)=O)=CC=2)C=2N=C(SC=2)C=2C=CC=CC=2)=N1 SXEJIWMUFRXLJZ-FQEVSTJZSA-N 0.000 claims 1
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