KR20090087044A - TAFIa 억제제로서의 요소 및 설파미드 유도체 - Google Patents
TAFIa 억제제로서의 요소 및 설파미드 유도체 Download PDFInfo
- Publication number
- KR20090087044A KR20090087044A KR1020097011740A KR20097011740A KR20090087044A KR 20090087044 A KR20090087044 A KR 20090087044A KR 1020097011740 A KR1020097011740 A KR 1020097011740A KR 20097011740 A KR20097011740 A KR 20097011740A KR 20090087044 A KR20090087044 A KR 20090087044A
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- KR
- South Korea
- Prior art keywords
- alkylene
- alkyl
- phenyl
- amino
- substituted
- 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.)
- Abandoned
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- 239000004202 carbamide Substances 0.000 title claims description 4
- 239000003112 inhibitor Substances 0.000 title abstract description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
- 208000005189 Embolism Diseases 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 8
- 229940079593 drug Drugs 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 230000003176 fibrotic effect Effects 0.000 claims abstract description 7
- 206010020608 Hypercoagulation Diseases 0.000 claims abstract description 5
- 230000003027 hypercoagulation Effects 0.000 claims abstract description 5
- 230000009863 secondary prevention Effects 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 carboxyl radicals Chemical class 0.000 claims description 520
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 488
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 282
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 222
- 229910052736 halogen Inorganic materials 0.000 claims description 193
- 150000002367 halogens Chemical class 0.000 claims description 193
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 110
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 93
- 125000002947 alkylene group Chemical group 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 40
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 40
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 35
- 125000006413 ring segment Chemical group 0.000 claims description 35
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 34
- 150000001413 amino acids Chemical class 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 125000002619 bicyclic group Chemical group 0.000 claims description 32
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000005508 decahydronaphthalenyl group Chemical group 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims description 30
- 125000002950 monocyclic group Chemical group 0.000 claims description 29
- 125000001544 thienyl group Chemical group 0.000 claims description 27
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 150000002926 oxygen Chemical class 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 229910052717 sulfur Chemical class 0.000 claims description 21
- 239000011593 sulfur Chemical class 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 18
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- NGERQMAWGVKQNJ-UHFFFAOYSA-N 4-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1NCC2 NGERQMAWGVKQNJ-UHFFFAOYSA-N 0.000 claims description 17
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 17
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 17
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 229940124530 sulfonamide Drugs 0.000 claims description 11
- 238000001356 surgical procedure Methods 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 10
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 10
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 9
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 9
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 9
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 9
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 9
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 9
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 9
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 9
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 9
- 125000002785 azepinyl group Chemical group 0.000 claims description 9
- 125000002393 azetidinyl group Chemical group 0.000 claims description 9
- 125000004069 aziridinyl group Chemical group 0.000 claims description 9
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000005512 benztetrazolyl group Chemical group 0.000 claims description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 125000004623 carbolinyl group Chemical group 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 9
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 9
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 9
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 9
- 125000000532 dioxanyl group Chemical group 0.000 claims description 9
- 125000003838 furazanyl group Chemical group 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 9
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 9
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 9
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 9
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 9
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims description 9
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 9
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 9
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 9
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 9
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 9
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 9
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims description 9
- 229940125670 thienopyridine Drugs 0.000 claims description 9
- 239000002175 thienopyridine Substances 0.000 claims description 9
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
- 125000004306 triazinyl group Chemical group 0.000 claims description 9
- 102000009123 Fibrin Human genes 0.000 claims description 8
- 108010073385 Fibrin Proteins 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 8
- 229950003499 fibrin Drugs 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000005968 oxazolinyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 239000012991 xanthate Substances 0.000 claims description 7
- 230000005526 G1 to G0 transition Effects 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 238000005345 coagulation Methods 0.000 claims description 6
- 230000015271 coagulation Effects 0.000 claims description 6
- 230000008021 deposition Effects 0.000 claims description 6
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000001212 derivatisation Methods 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010051055 Deep vein thrombosis Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 208000012659 Joint disease Diseases 0.000 claims description 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 3
- 206010027476 Metastases Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 206010047249 Venous thrombosis Diseases 0.000 claims description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- 230000003412 degenerative effect Effects 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 210000003127 knee Anatomy 0.000 claims description 3
- 230000009401 metastasis Effects 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 230000000250 revascularization Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 3
- 230000004614 tumor growth Effects 0.000 claims description 3
- 208000019553 vascular disease Diseases 0.000 claims description 3
- 210000003462 vein Anatomy 0.000 claims description 3
- BYODFAIWNUGOEG-HKBOAZHASA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@@H](C(C)C)C(N)=O)CCCCNC(=O)OCC1=CC=CC=C1 BYODFAIWNUGOEG-HKBOAZHASA-N 0.000 claims description 2
- WOOPVCXLDZQZBY-VQTJNVASSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(2,4-difluorophenyl)methylamino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C(=CC(F)=CC=1)F)C1CCCCC1 WOOPVCXLDZQZBY-VQTJNVASSA-N 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
- 208000024659 Hemostatic disease Diseases 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 230000037390 scarring Effects 0.000 claims description 2
- 229960002684 aminocaproic acid Drugs 0.000 claims 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- ASUVGRQRVLPDIT-JRGCBEDISA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(1r)-1-phenylethyl]amino]propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@H](C)C=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 ASUVGRQRVLPDIT-JRGCBEDISA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- RIXNOHFAOYJMSZ-CIICBDETSA-N (2r)-3-(2-aminoethylsulfanyl)-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]propan-2-yl]carbamoylamino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)NC(=O)N[C@@H](CSCCN)C(O)=O)C1CCCCC1 RIXNOHFAOYJMSZ-CIICBDETSA-N 0.000 claims 1
- GDWHWWKAZILMHH-CIICBDETSA-N (2r)-3-(2-aminoethylsulfonyl)-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]propan-2-yl]carbamoylamino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)NC(=O)N[C@@H](CS(=O)(=O)CCN)C(O)=O)C1CCCCC1 GDWHWWKAZILMHH-CIICBDETSA-N 0.000 claims 1
- GMBWYAWMTMTQBC-QLOIWQOISA-N (2r)-3-(6-aminopyridin-3-yl)-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]propan-2-yl]carbamoylamino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)NC(=O)N[C@H](CC=1C=NC(N)=CC=1)C(O)=O)C1CCCCC1 GMBWYAWMTMTQBC-QLOIWQOISA-N 0.000 claims 1
- UCEGGLPSQBLVBB-QYKBZSJISA-N (2s)-2-[[(2r)-1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ylamino)-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]-6-aminohexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NC1CC2CCCCC2CC1)C1CCCCC1 UCEGGLPSQBLVBB-QYKBZSJISA-N 0.000 claims 1
- VKZAQVIYSIRHRU-LJHZMQABSA-N (2s)-2-[[(2r)-1-(1-adamantylamino)-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]-6-aminohexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NC12CC3CC(CC(C3)C1)C2)C1CCCCC1 VKZAQVIYSIRHRU-LJHZMQABSA-N 0.000 claims 1
- TZEBOPOLYUOKMZ-IHZBLBIESA-N (2s)-2-[[(2r)-3-cyclohexyl-1-[[(2s)-1-[[(2s)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]-5-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@H](CO)CC=1C=CC=CC=1)NC(=O)N[C@@H](CCCNC(=O)OCC=1C=CC=CC=1)C(O)=O)C1CCCCC1 TZEBOPOLYUOKMZ-IHZBLBIESA-N 0.000 claims 1
- OAYPFQQPQAHETG-QIFMEBFJSA-N (2s)-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]propan-2-yl]carbamoylamino]-4-(diaminomethylideneamino)oxybutanoic acid Chemical compound C([C@H](C(=O)N[C@@H]1[C@]2(C)CCC(C1)C2(C)C)NC(=O)N[C@@H](CCON=C(N)N)C(O)=O)C1CCCCC1 OAYPFQQPQAHETG-QIFMEBFJSA-N 0.000 claims 1
- GMBWYAWMTMTQBC-UVBRCTSRSA-N (2s)-3-(6-aminopyridin-3-yl)-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]propan-2-yl]carbamoylamino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)NC(=O)N[C@@H](CC=1C=NC(N)=CC=1)C(O)=O)C1CCCCC1 GMBWYAWMTMTQBC-UVBRCTSRSA-N 0.000 claims 1
- MZRFWFIFSUOFHJ-MCJVGQIASA-N (2s)-5-amino-2-[[(2r)-3-cyclohexyl-1-(3-methylbutylamino)-1-oxopropan-2-yl]carbamoylamino]pentanoic acid;hydrochloride Chemical compound Cl.NCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCCC(C)C)CC1CCCCC1 MZRFWFIFSUOFHJ-MCJVGQIASA-N 0.000 claims 1
- CQNSMAZPVAUNAU-AVFSDTQCSA-N (2s)-5-amino-2-[[1-cyclohexyl-4-oxo-4-[[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]butan-2-yl]carbamoylamino]pentanoic acid Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(=O)CC(NC(=O)N[C@@H](CCCN)C(O)=O)CC1CCCCC1 CQNSMAZPVAUNAU-AVFSDTQCSA-N 0.000 claims 1
- MSTLWUDFQHMEJM-DLBZAZTESA-N (2s)-6-amino-2-[[(2r)-1-(2-methylpropylamino)-1-oxo-3-phenylpropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCC(C)C)CC1=CC=CC=C1 MSTLWUDFQHMEJM-DLBZAZTESA-N 0.000 claims 1
- HKPGTWCJLYFZSN-AXGZHYKBSA-N (2s)-6-amino-2-[[(2r)-1-(3-bicyclo[2.2.1]heptanylamino)-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NC1C2CCC(C2)C1)C1CCCCC1 HKPGTWCJLYFZSN-AXGZHYKBSA-N 0.000 claims 1
- DHJKOJJNOXPCSU-ZWKOTPCHSA-N (2s)-6-amino-2-[[(2r)-1-(3-methylbutylamino)-1-oxo-3-phenylpropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCCC(C)C)CC1=CC=CC=C1 DHJKOJJNOXPCSU-ZWKOTPCHSA-N 0.000 claims 1
- CHTDAZARBWINCK-YADHBBJMSA-N (2s)-6-amino-2-[[(2r)-1-(3-methylbutylamino)-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCCC(C)C)CCCCNC(=O)OCC1=CC=CC=C1 CHTDAZARBWINCK-YADHBBJMSA-N 0.000 claims 1
- CMGFAPLRKUXFDR-CABCVRRESA-N (2s)-6-amino-2-[[(2r)-1-(3-methylbutylamino)-1-oxohexan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC(C)CCNC(=O)[C@@H](CCCC)NC(=O)N[C@@H](CCCCN)C(O)=O CMGFAPLRKUXFDR-CABCVRRESA-N 0.000 claims 1
- CLFUFGINFOBXTN-KGLIPLIRSA-N (2s)-6-amino-2-[[(2r)-1-(3-methylbutylamino)-1-oxopentan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC(C)CCNC(=O)[C@@H](CCC)NC(=O)N[C@@H](CCCCN)C(O)=O CLFUFGINFOBXTN-KGLIPLIRSA-N 0.000 claims 1
- DOPAUDNYDCEYJL-NEPJUHHUSA-N (2s)-6-amino-2-[[(2r)-1-(3-methylbutylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC(C)CCNC(=O)[C@@H](C)NC(=O)N[C@H](C(O)=O)CCCCN DOPAUDNYDCEYJL-NEPJUHHUSA-N 0.000 claims 1
- NJNGCIKHAZSESX-YADHBBJMSA-N (2s)-6-amino-2-[[(2r)-1-[(1-methoxycarbonylcyclopentyl)amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound O=C([C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)NC1(C(=O)OC)CCCC1 NJNGCIKHAZSESX-YADHBBJMSA-N 0.000 claims 1
- QZCYCDFEUPHRFV-GXYBFCANSA-N (2s)-6-amino-2-[[(2r)-1-[(2-methylcyclohexyl)amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC1CCCCC1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 QZCYCDFEUPHRFV-GXYBFCANSA-N 0.000 claims 1
- OJERXZIUSQLLLQ-YADHBBJMSA-N (2s)-6-amino-2-[[(2r)-1-[(3-methyl-1,2-oxazol-5-yl)methylamino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound O1N=C(C)C=C1CNC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 OJERXZIUSQLLLQ-YADHBBJMSA-N 0.000 claims 1
- RFNAJQKHWYWBFC-RPWUZVMVSA-N (2s)-6-amino-2-[[(2r)-1-[(4-chlorophenyl)methylamino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C=CC(Cl)=CC=1)CCCNC(=O)OCC1=CC=CC=C1 RFNAJQKHWYWBFC-RPWUZVMVSA-N 0.000 claims 1
- XWLUNSVBQCMZQN-VQTJNVASSA-N (2s)-6-amino-2-[[(2r)-1-[2-(1,3-benzodioxol-5-yl)ethylamino]-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCCC=1C=C2OCOC2=CC=1)C1CCCCC1 XWLUNSVBQCMZQN-VQTJNVASSA-N 0.000 claims 1
- LCCMZNPEYXGRQI-NIVHGDGRSA-N (2s)-6-amino-2-[[(2r)-1-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NC1[C@@]2([H])CC[C@](C2)(C1)[H])NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 LCCMZNPEYXGRQI-NIVHGDGRSA-N 0.000 claims 1
- BLAHYZRLRMLVGC-RCTAOEEJSA-N (2s)-6-amino-2-[[(2r)-1-[[(1s,2r)-2-ethoxycarbonylcyclohexyl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound CCOC(=O)[C@@H]1CCCC[C@@H]1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 BLAHYZRLRMLVGC-RCTAOEEJSA-N 0.000 claims 1
- NAUHSWLVSPZSJK-KWXIBIRDSA-N (2s)-6-amino-2-[[(2r)-1-[[(2r)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)OCC)NC(=O)[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1=CC=CC=C1 NAUHSWLVSPZSJK-KWXIBIRDSA-N 0.000 claims 1
- NIYRPIAOJKRJAU-RLLQIKCJSA-N (2s)-6-amino-2-[[(2r)-1-[[(2r)-1-methoxy-1-oxopropan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@H](C)C(=O)OC)CCCCNC(=O)OCC1=CC=CC=C1 NIYRPIAOJKRJAU-RLLQIKCJSA-N 0.000 claims 1
- XFHWGGOUBWYTSM-DSITVLBTSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-(2,2-dimethylpropylamino)-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@@H](C(C)C)C(=O)NCC(C)(C)C)CCCCNC(=O)OCC1=CC=CC=C1 XFHWGGOUBWYTSM-DSITVLBTSA-N 0.000 claims 1
- ZZFQPFZJGSEXEA-OLORSWDZSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-(3,3-dimethylbutan-2-ylamino)-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@@H](C(C)C)C(=O)NC(C)C(C)(C)C)CCCCNC(=O)OCC1=CC=CC=C1 ZZFQPFZJGSEXEA-OLORSWDZSA-N 0.000 claims 1
- NWXNQDHLMQUILK-SGNDLWITSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-(cyclopropylamino)-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)NC1CC1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 NWXNQDHLMQUILK-SGNDLWITSA-N 0.000 claims 1
- LIUGTCPGAFNONM-PKTNWEFCSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[(4-chlorophenyl)methylamino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)NCC=1C=CC(Cl)=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 LIUGTCPGAFNONM-PKTNWEFCSA-N 0.000 claims 1
- DZVRPSSVBDBPNZ-GXBVYBDKSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(1s)-1-(4-chlorophenyl)ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C=1C=CC(Cl)=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 DZVRPSSVBDBPNZ-GXBVYBDKSA-N 0.000 claims 1
- HIRBMMFKBYAZRK-LQBCTSRJSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(1s)-1-cyclohexylethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C1CCCCC1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 HIRBMMFKBYAZRK-LQBCTSRJSA-N 0.000 claims 1
- AEWYQEJGSLGUPB-WAKZHNDOSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@H](C(=O)N[C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C(C)C)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 AEWYQEJGSLGUPB-WAKZHNDOSA-N 0.000 claims 1
- YIGSOJAEIOSEPW-WOZUAGRISA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(2s)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(C)C)C(N)=O)C(C)C)CC1CCCCC1 YIGSOJAEIOSEPW-WOZUAGRISA-N 0.000 claims 1
- RMFOUMJHZRHSQS-BHSUFKTOSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(2s)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](C(=O)OCC)NC(=O)[C@@H](NC(=O)[C@@H](CCCCNC(=O)OCC=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)C(C)C)C1=CC=CC=C1 RMFOUMJHZRHSQS-BHSUFKTOSA-N 0.000 claims 1
- GTTHQPYILSKHPE-WKAQUBQDSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(2s)-1-ethoxy-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound CCOC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 GTTHQPYILSKHPE-WKAQUBQDSA-N 0.000 claims 1
- IQKNJEPFZBWSJP-ZLESDFJESA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-[[(2s)-3-(1h-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@H](C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)OC)C(C)C)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 IQKNJEPFZBWSJP-ZLESDFJESA-N 0.000 claims 1
- QHVXTZWTMAJUSO-VJBWXMMDSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-1-ethoxy-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@H](C(=O)OCC)C(C)C)CCCCNC(=O)OCC1=CC=CC=C1 QHVXTZWTMAJUSO-VJBWXMMDSA-N 0.000 claims 1
- HMUKXDNIUMCNEZ-HNLSKPFFSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-3-methyl-1-[(3-methylcyclohexyl)amino]-1-oxobutan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)NC1CC(C)CCC1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 HMUKXDNIUMCNEZ-HNLSKPFFSA-N 0.000 claims 1
- JXAOTDOTBBROQW-NGDRWEMDSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-3-methyl-1-oxo-1-(3-phenylpropylamino)butan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)NCCCC=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 JXAOTDOTBBROQW-NGDRWEMDSA-N 0.000 claims 1
- JYDRAYXXFUVQRZ-PCPRHZMTSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s)-3-methyl-1-oxo-1-[[(1r,2s)-2-phenylcyclopropyl]amino]butan-2-yl]amino]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@H]1[C@@H](C1)C=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 JYDRAYXXFUVQRZ-PCPRHZMTSA-N 0.000 claims 1
- GVLSFZGGBDHKNC-UMESGILHSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s,3r)-1-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H]([C@H](C)CC)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 GVLSFZGGBDHKNC-UMESGILHSA-N 0.000 claims 1
- HBVILXKIYOXJJQ-SPUZQDLCSA-N (2s)-6-amino-2-[[(2r)-1-[[(2s,3r)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@@H]([C@H](C)CC)C(N)=O)CC1CCCCC1 HBVILXKIYOXJJQ-SPUZQDLCSA-N 0.000 claims 1
- GCAITSKOIIQUDT-SDUSCBPUSA-N (2s)-6-amino-2-[[(2r)-1-oxo-1-[[(1r)-1-phenylethyl]amino]-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@H](C)C=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 GCAITSKOIIQUDT-SDUSCBPUSA-N 0.000 claims 1
- YDBFJYMNIYWBMG-DVSPJEKPSA-N (2s)-6-amino-2-[[(2r)-1-oxo-6-(phenylmethoxycarbonylamino)-1-(2-phenylpropylamino)hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NCC(C)C=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 YDBFJYMNIYWBMG-DVSPJEKPSA-N 0.000 claims 1
- WZQBRHIXFFKZSY-IHLOFXLRSA-N (2s)-6-amino-2-[[(2r)-1-oxo-6-(phenylmethoxycarbonylamino)-1-[(2-phenylphenyl)methylamino]hexan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C(=CC=CC=1)C=1C=CC=CC=1)CCCNC(=O)OCC1=CC=CC=C1 WZQBRHIXFFKZSY-IHLOFXLRSA-N 0.000 claims 1
- MAADCGOFVALXMT-RRPNLBNLSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(2,2-diphenylethylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC(C=1C=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 MAADCGOFVALXMT-RRPNLBNLSA-N 0.000 claims 1
- DYGJQKUVLFKUEQ-XSRYCBBQSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(2-methylbutylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCC(C)CC)CC1CCCCC1 DYGJQKUVLFKUEQ-XSRYCBBQSA-N 0.000 claims 1
- RUWUSBDCRNJOMS-DLBZAZTESA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(2-methylpropylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCC(C)C)CC1CCCCC1 RUWUSBDCRNJOMS-DLBZAZTESA-N 0.000 claims 1
- ISGJHRGZGUNOGI-XSRYCBBQSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(2-methylpyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC1CCCN1C(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 ISGJHRGZGUNOGI-XSRYCBBQSA-N 0.000 claims 1
- QESTYHACMRZORU-YVZJPGBNSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(3-methylpentan-2-ylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NC(C)C(C)CC)CC1CCCCC1 QESTYHACMRZORU-YVZJPGBNSA-N 0.000 claims 1
- PONLJKVPNOOICN-NGFYBIIMSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(4-methylpentan-2-ylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NC(C)CC(C)C)CC1CCCCC1 PONLJKVPNOOICN-NGFYBIIMSA-N 0.000 claims 1
- MKKJYQVIMAUBBS-JKSUJKDBSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-(cyclopropylamino)-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NC1CC1)C1CCCCC1 MKKJYQVIMAUBBS-JKSUJKDBSA-N 0.000 claims 1
- KRMAOZKMUIRYKA-DLBZAZTESA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(1-ethoxycarbonylcyclopropyl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound O=C([C@@H](CC1CCCCC1)NC(=O)N[C@@H](CCCCN)C(O)=O)NC1(C(=O)OCC)CC1 KRMAOZKMUIRYKA-DLBZAZTESA-N 0.000 claims 1
- DMVCVVLKRSBMED-JKSUJKDBSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(1-methoxy-2-methyl-1-oxopropan-2-yl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NC(C)(C)C(=O)OC)CC1CCCCC1 DMVCVVLKRSBMED-JKSUJKDBSA-N 0.000 claims 1
- VSGWYLBCTYJTHD-VQTJNVASSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(1-methylbenzimidazol-2-yl)methylamino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NCC=1N(C2=CC=CC=C2N=1)C)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 VSGWYLBCTYJTHD-VQTJNVASSA-N 0.000 claims 1
- ARPRNVUWWNGLSA-RBUKOAKNSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(1-methylpiperidin-4-yl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C1CN(C)CCC1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 ARPRNVUWWNGLSA-RBUKOAKNSA-N 0.000 claims 1
- VEVYNIACOXVJDA-YSYVIGEPSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(2,3-dimethylcyclohexyl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC1C(C)CCCC1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 VEVYNIACOXVJDA-YSYVIGEPSA-N 0.000 claims 1
- IDPIKFFIXVNIMR-FCHUYYIVSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(2,3-dimethylphenyl)methylamino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC1=CC=CC(CNC(=O)[C@@H](CC2CCCCC2)NC(=O)N[C@@H](CCCCN)C(O)=O)=C1C IDPIKFFIXVNIMR-FCHUYYIVSA-N 0.000 claims 1
- FKOXBDDJOZAVOK-DXBWTPJFSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(2-methylcyclohexyl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC1CCCCC1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 FKOXBDDJOZAVOK-DXBWTPJFSA-N 0.000 claims 1
- BUGBSBMOSNEBKD-VQTJNVASSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(3,5-difluorophenyl)methylamino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C=C(F)C=C(F)C=1)C1CCCCC1 BUGBSBMOSNEBKD-VQTJNVASSA-N 0.000 claims 1
- VMMJGBVHKXLULU-DXBWTPJFSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(3-methylcyclohexyl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C1C(C)CCCC1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 VMMJGBVHKXLULU-DXBWTPJFSA-N 0.000 claims 1
- VEDZNKIGSSHCLR-LEWJYISDSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(4-methoxyphenyl)methylamino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1CNC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 VEDZNKIGSSHCLR-LEWJYISDSA-N 0.000 claims 1
- ZUYRNRCIQPTMPP-DXBWTPJFSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[(4-methylcyclohexyl)amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C1CC(C)CCC1NC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 ZUYRNRCIQPTMPP-DXBWTPJFSA-N 0.000 claims 1
- PQVPFBJWSKJZQI-FCHUYYIVSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[2-(2-methylphenyl)ethylamino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC1=CC=CC=C1CCNC(=O)[C@H](NC(=O)N[C@@H](CCCCN)C(O)=O)CC1CCCCC1 PQVPFBJWSKJZQI-FCHUYYIVSA-N 0.000 claims 1
- ZGXFMFPAIIYCKE-TYCQWZJGSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(1r)-1-(4-fluorophenyl)ethyl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@H](C)C=1C=CC(F)=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 ZGXFMFPAIIYCKE-TYCQWZJGSA-N 0.000 claims 1
- AFPITHMSIWIQKS-DZFGPLHGSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(1s)-1-cyclohexylethyl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C)C1CCCCC1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 AFPITHMSIWIQKS-DZFGPLHGSA-N 0.000 claims 1
- PGKTWPKLTNYPMW-BPQIPLTHSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(2r)-3-methylbutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@H](C)C(C)C)CC1CCCCC1 PGKTWPKLTNYPMW-BPQIPLTHSA-N 0.000 claims 1
- IXUFJIXQMMKHEV-OTWHNJEPSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(2s)-1-(ethylamino)-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC)C(C)C)CC1CCCCC1 IXUFJIXQMMKHEV-OTWHNJEPSA-N 0.000 claims 1
- KKYSFOBZVLEFGF-QYOOZWMWSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(2s)-1-[[(2s)-3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](C(=O)OC)NC(=O)[C@@H](NC(=O)[C@@H](CC1CCCCC1)NC(=O)N[C@@H](CCCCN)C(O)=O)C(C)C)C1=CC=C(O)C=C1 KKYSFOBZVLEFGF-QYOOZWMWSA-N 0.000 claims 1
- ZUZNAMMEBUGMMN-ZRBLBEILSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(2s)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](C(=O)OCC)NC(=O)[C@@H](CC1CCCCC1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1=CC=CC=C1 ZUZNAMMEBUGMMN-ZRBLBEILSA-N 0.000 claims 1
- XYNZYKIVZSVBOE-OTWHNJEPSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(2s)-1-ethoxy-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@H](C(=O)OCC)C(C)C)CC1CCCCC1 XYNZYKIVZSVBOE-OTWHNJEPSA-N 0.000 claims 1
- NNJRKAXGAYFSMV-LULLPPNCSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[(2s,3r)-1-methoxy-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@@H]([C@H](C)CC)C(=O)OC)CC1CCCCC1 NNJRKAXGAYFSMV-LULLPPNCSA-N 0.000 claims 1
- ZZGIXTIOLKNBBS-FVNVNRQCSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-[[1-[[(2s)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NC(C(C)C)C(=O)N[C@H](CO)CC=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 ZZGIXTIOLKNBBS-FVNVNRQCSA-N 0.000 claims 1
- ASEMKOPIZGXBNF-ATTQYFOMSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(1,2,3,4-tetrahydronaphthalen-2-ylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NC1CC2=CC=CC=C2CC1)C1CCCCC1 ASEMKOPIZGXBNF-ATTQYFOMSA-N 0.000 claims 1
- JEAKSEPJFOONBE-LFZQMPOYSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(2-phenylpropylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NCC(C)C=1C=CC=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 JEAKSEPJFOONBE-LFZQMPOYSA-N 0.000 claims 1
- SGPRILNHYWHWBL-LSDHHAIUSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(3,3,3-trifluoropropylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)NCCC(F)(F)F)CC1CCCCC1 SGPRILNHYWHWBL-LSDHHAIUSA-N 0.000 claims 1
- UXPLRHGBJCAHHN-FCHUYYIVSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(3-phenylpropylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCCCC=1C=CC=CC=1)C1CCCCC1 UXPLRHGBJCAHHN-FCHUYYIVSA-N 0.000 claims 1
- MOTJWHVGDSWUDZ-RBUKOAKNSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(pyridin-2-ylmethylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1N=CC=CC=1)C1CCCCC1 MOTJWHVGDSWUDZ-RBUKOAKNSA-N 0.000 claims 1
- YKNDFHKHEMQIRT-RBUKOAKNSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(pyridin-3-ylmethylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C=NC=CC=1)C1CCCCC1 YKNDFHKHEMQIRT-RBUKOAKNSA-N 0.000 claims 1
- UPKXTXVXXINMPZ-RBUKOAKNSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(pyridin-4-ylmethylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C=CN=CC=1)C1CCCCC1 UPKXTXVXXINMPZ-RBUKOAKNSA-N 0.000 claims 1
- ICFMWOIEAALHLR-ZWKOTPCHSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(thiophen-2-ylmethylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1SC=CC=1)C1CCCCC1 ICFMWOIEAALHLR-ZWKOTPCHSA-N 0.000 claims 1
- FMZGIGXVQFRBQJ-ZWKOTPCHSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-(thiophen-3-ylmethylamino)propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC1=CSC=C1)C1CCCCC1 FMZGIGXVQFRBQJ-ZWKOTPCHSA-N 0.000 claims 1
- SSFSNJSPMNRENT-IZZNHLLZSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-[(2-phenylphenyl)methylamino]propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)NCC=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 SSFSNJSPMNRENT-IZZNHLLZSA-N 0.000 claims 1
- YSWQKZLGVCEJAT-XVQIHIMPSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(1r)-2-phenylcyclopropyl]amino]propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@@H](NC(=O)N[C@@H](CCCCN)C(O)=O)C(=O)N[C@H]1C(C1)C=1C=CC=CC=1)C1CCCCC1 YSWQKZLGVCEJAT-XVQIHIMPSA-N 0.000 claims 1
- AUFLFYNRNWZZKB-OGDMEQELSA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]amino]propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NC1[C@@]2(C)CCC(C1)C2(C)C)NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 AUFLFYNRNWZZKB-OGDMEQELSA-N 0.000 claims 1
- QUUSJRRLGYKBRS-BBUZFYHESA-N (2s)-6-amino-2-[[(2r)-3-cyclohexyl-1-oxo-1-[[(4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]methylamino]propan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)NCC1CC2C[C@@]([C@@H]1C)(C2(C)C)[H])NC(=O)N[C@@H](CCCCN)C(O)=O)C1CCCCC1 QUUSJRRLGYKBRS-BBUZFYHESA-N 0.000 claims 1
- KULRESXLHOIMCE-LSDHHAIUSA-N (2s)-6-amino-2-[[(2r)-4-methyl-1-(3-methylbutylamino)-1-oxopentan-2-yl]carbamoylamino]hexanoic acid Chemical compound CC(C)CCNC(=O)[C@@H](CC(C)C)NC(=O)N[C@H](C(O)=O)CCCCN KULRESXLHOIMCE-LSDHHAIUSA-N 0.000 claims 1
- PDOXRYBUHNJFJM-UTVGCEEQSA-N (2s)-6-amino-2-[[(2r)-6-amino-1-[[(1s)-1-(4-chlorophenyl)ethyl]amino]-1,7-dioxo-7-phenylmethoxyheptan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C)C=1C=CC(Cl)=CC=1)NC(=O)N[C@@H](CCCCN)C(O)=O)CCC(N)C(=O)OCC1=CC=CC=C1 PDOXRYBUHNJFJM-UTVGCEEQSA-N 0.000 claims 1
- LXCJPPPVHJBDNK-FDQAQLRPSA-N (2s)-6-amino-2-[[(2r)-6-amino-1-[[(2s)-1-[[(1r,4s)-3-bicyclo[2.2.1]heptanyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,7-dioxo-7-phenylmethoxyheptan-2-yl]carbamoylamino]hexanoic acid Chemical compound C([C@H](C(=O)N[C@H](C(=O)NC1[C@@]2([H])CC[C@](C2)(C1)[H])C(C)C)NC(=O)N[C@@H](CCCCN)C(O)=O)CCC(N)C(=O)OCC1=CC=CC=C1 LXCJPPPVHJBDNK-FDQAQLRPSA-N 0.000 claims 1
- RNBKSLUMLDKSFU-CSRKEZGKSA-N (2s)-6-amino-2-[[(2r)-6-amino-1-[[(2s,3s)-1-methoxy-3-methyl-1-oxopentan-2-yl]amino]-1,7-dioxo-7-phenylmethoxyheptan-2-yl]carbamoylamino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)N[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)OC)CCCC(N)C(=O)OCC1=CC=CC=C1 RNBKSLUMLDKSFU-CSRKEZGKSA-N 0.000 claims 1
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| ES2494390T3 (es) | 2008-06-06 | 2014-09-15 | Sanofi | Derivados macrocíclicos de urea y de sulfamida como inhibidores de TAFIa |
| AU2009263076B2 (en) | 2008-06-23 | 2012-07-26 | Astrazeneca Ab | New heterocyclic carboxamides for use as thrombin inhibitors |
| US8354444B2 (en) | 2008-09-18 | 2013-01-15 | Hoffmann-La Roche Inc. | Substituted pyrrolidine-2-carboxamides |
| AU2009310841A1 (en) * | 2008-10-29 | 2010-05-06 | Taisho Pharmaceutical Co., Ltd. | Compounds having TAFIa inhibitory activity |
| EP3027611B1 (en) * | 2013-06-10 | 2017-07-26 | Sanofi | Macrocyclic urea derivatives as inhibitors of tafi a, their preparation and their use as pharmaceuticals |
| CN104529859B (zh) * | 2015-01-13 | 2016-08-17 | 佛山市赛维斯医药科技有限公司 | 含苯胺和二烯氟代金刚烷结构的化合物、其制备方法和用途 |
| RU2687254C1 (ru) * | 2018-10-03 | 2019-05-08 | Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) | N-гетероциклические производные борниламина в качестве ингибиторов ортопоксвирусов |
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| TW394760B (en) * | 1993-09-07 | 2000-06-21 | Hoffmann La Roche | Novel Carboxamides, process for their preparation and pharmaceutical composition containing the same |
| CA2298601A1 (en) * | 1997-08-28 | 1999-03-11 | Pharmacia & Upjohn Company | Inhibitors of protein tyrosine phosphatase |
| US6482921B1 (en) * | 1999-01-28 | 2002-11-19 | Essential Therapeutics, Inc. | Uridyl peptide antibiotic (UPA) derivatives, their synthesis and use |
| WO2000056725A1 (en) * | 1999-03-19 | 2000-09-28 | Du Pont Pharmaceuticals Company | N-adamant-1-yl-n'-[4-chlorobenzothiazol-2-yl] urea useful in the treatment of inflammation and as an anticancer radiosensitizing agent |
| US6359129B1 (en) * | 2000-08-15 | 2002-03-19 | University Of Kansas | Amino acid-derived, 7-membered cyclic sulfamides and methods of synthesizing the same |
| ATE447557T1 (de) * | 2000-08-17 | 2009-11-15 | Pfizer Ltd | Substitutuierte imidazole als tafia inhibitoren |
| DE102004020186A1 (de) * | 2004-04-22 | 2005-11-17 | Aventis Pharma Deutschland Gmbh | Heterocyclylessigsäuren als Inhibitoren von TAFla |
| CA2583089A1 (en) * | 2004-10-05 | 2006-04-20 | Bayer Schering Pharma Aktiengesellschaft | Tafi inhibitors and their use to treat pulmonary fibrosis |
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