JP2004526662A - プロテアーゼ阻害剤 - Google Patents

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Publication number

JP2004526662A

JP2004526662A JP2001585697A JP2001585697A JP2004526662A JP 2004526662 A JP2004526662 A JP 2004526662A JP 2001585697 A JP2001585697 A JP 2001585697A JP 2001585697 A JP2001585697 A JP 2001585697A JP 2004526662 A JP2004526662 A JP 2004526662A

Authority

JP

Japan

Prior art keywords

alkyl

carboxylic acid

azepan

ethyl

sulfonyl

Prior art date

2000-04-18

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.)

Withdrawn

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• 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 3
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 182
• 238000000034 method Methods 0.000 claims abstract description 97
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
• 108090000613 Cathepsin S Proteins 0.000 claims abstract description 20
• 102100035654 Cathepsin S Human genes 0.000 claims abstract description 20
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 230000028993 immune response Effects 0.000 claims abstract description 15
• 230000002265 prevention Effects 0.000 claims abstract description 11
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
• 230000000694 effects Effects 0.000 claims abstract description 10
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 10
• 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 8
• 208000037260 Atherosclerotic Plaque Diseases 0.000 claims abstract description 8
• 102000016387 Pancreatic elastase Human genes 0.000 claims abstract description 8
• 108010067372 Pancreatic elastase Proteins 0.000 claims abstract description 8
• 208000006673 asthma Diseases 0.000 claims abstract description 7
• 208000035475 disorder Diseases 0.000 claims abstract description 7
• 210000000056 organ Anatomy 0.000 claims abstract description 7
• 230000004044 response Effects 0.000 claims abstract description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
• 208000026935 allergic disease Diseases 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 115
• -1 Furo [3,2-b] -pyridin-2-yl Chemical group 0.000 claims description 99
• SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 93
• 150000001408 amides Chemical class 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 230000005764 inhibitory process Effects 0.000 claims description 18
• IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 14
• YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 claims description 13
• HQULGJDHOPDURG-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=N1 HQULGJDHOPDURG-UHFFFAOYSA-N 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 claims description 10
• JJWBLYNHZXZGIQ-UHFFFAOYSA-N 5-(2-morpholin-4-ylethoxy)-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)=CC2=CC=1OCCN1CCOCC1 JJWBLYNHZXZGIQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 230000001363 autoimmune Effects 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 8
• QFDHWPOPCNNAOI-UHFFFAOYSA-N 4-methyl-2-pyridin-2-yl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=CC=CC=N1 QFDHWPOPCNNAOI-UHFFFAOYSA-N 0.000 claims description 7
• VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 claims description 7
• KZCODYXMOKIMLT-GIVPXCGWSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]furan-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C=1OC=CC=1)C1CCCCC1 KZCODYXMOKIMLT-GIVPXCGWSA-N 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• FTKDCOINUAYGTC-UHFFFAOYSA-N 3-ethoxythiophene-2-carboxylic acid Chemical compound CCOC=1C=CSC=1C(O)=O FTKDCOINUAYGTC-UHFFFAOYSA-N 0.000 claims description 6
• XIPQHWUSDHTXOO-UHFFFAOYSA-N 5-(4-chlorophenyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 XIPQHWUSDHTXOO-UHFFFAOYSA-N 0.000 claims description 6
• ADRFTNFHVKVATK-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 ADRFTNFHVKVATK-UHFFFAOYSA-N 0.000 claims description 6
• 201000011152 Pemphigus Diseases 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 201000001976 pemphigus vulgaris Diseases 0.000 claims description 6
• WAQBFLCVNNZBQR-UHFFFAOYSA-N selenophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C[se]1 WAQBFLCVNNZBQR-UHFFFAOYSA-N 0.000 claims description 6
• 210000001519 tissue Anatomy 0.000 claims description 6
• DBOYFDWWHUOJED-VDZZXDNDSA-N (2r)-n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]oxolane-2-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)[C@@H]1OCCC1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 DBOYFDWWHUOJED-VDZZXDNDSA-N 0.000 claims description 5
• DBOYFDWWHUOJED-BXBRYHBFSA-N (2s)-n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]oxolane-2-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)[C@H]1OCCC1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 DBOYFDWWHUOJED-BXBRYHBFSA-N 0.000 claims description 5
• RJGMFNINUDKFJE-WCSIJFPASA-N 4-bromo-n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)N[C@H](C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)CC1CCCCC1 RJGMFNINUDKFJE-WCSIJFPASA-N 0.000 claims description 5
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• URSVVFCNNILESZ-LBAQZLPGSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]-3-ethoxythiophene-2-carboxamide Chemical compound C1=CSC(C(=O)N[C@@H](CC2CCCCC2)C(=O)NC2C(CN(CCC2)S(=O)(=O)C=2N=CC=CC=2)=O)=C1OCC URSVVFCNNILESZ-LBAQZLPGSA-N 0.000 claims description 5
• FGPFDDZGYPCICV-LBAQZLPGSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]-3-methylthiophene-2-carboxamide Chemical compound C1=CSC(C(=O)N[C@@H](CC2CCCCC2)C(=O)NC2C(CN(CCC2)S(=O)(=O)C=2N=CC=CC=2)=O)=C1C FGPFDDZGYPCICV-LBAQZLPGSA-N 0.000 claims description 5
• IIGUCKATGIQWSD-GITCGBDTSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]-4-methyl-2-pyridin-2-yl-1,3-thiazole-5-carboxamide Chemical compound C([C@H](NC(=O)C=1SC(=NC=1C)C=1N=CC=CC=1)C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)C1CCCCC1 IIGUCKATGIQWSD-GITCGBDTSA-N 0.000 claims description 5
• OQQOFIYYWYDXTB-LBAQZLPGSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]-5-methylthiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)N[C@H](C(=O)NC1C(CN(CCC1)S(=O)(=O)C=1N=CC=CC=1)=O)CC1CCCCC1 OQQOFIYYWYDXTB-LBAQZLPGSA-N 0.000 claims description 5
• GPIKRAJOPWBFKP-LBAQZLPGSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]cyclobutanecarboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C1CCC1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 GPIKRAJOPWBFKP-LBAQZLPGSA-N 0.000 claims description 5
• SQHAFDFRPJWBET-ANYOKISRSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]furan-2-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C=1OC=CC=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 SQHAFDFRPJWBET-ANYOKISRSA-N 0.000 claims description 5
• YXESHRFQRNZWFC-LBAQZLPGSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]thiophene-3-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C1=CSC=C1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 YXESHRFQRNZWFC-LBAQZLPGSA-N 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• AWGCBUDAZSSMQT-UHFFFAOYSA-N 5,6-dimethoxy-1-benzofuran-2-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1OC(C(O)=O)=C2 AWGCBUDAZSSMQT-UHFFFAOYSA-N 0.000 claims description 4
• 208000026872 Addison Disease Diseases 0.000 claims description 4
• 208000004300 Atrophic Gastritis Diseases 0.000 claims description 4
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 4
• 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 4
• 206010008909 Chronic Hepatitis Diseases 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 206010016654 Fibrosis Diseases 0.000 claims description 4
• 208000036495 Gastritis atrophic Diseases 0.000 claims description 4
• 208000024869 Goodpasture syndrome Diseases 0.000 claims description 4
• 208000015023 Graves' disease Diseases 0.000 claims description 4
• 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 4
• 206010020850 Hyperthyroidism Diseases 0.000 claims description 4
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims description 4
• 208000003250 Mixed connective tissue disease Diseases 0.000 claims description 4
• 206010028665 Myxoedema Diseases 0.000 claims description 4
• 208000031845 Pernicious anaemia Diseases 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 4
• 206010039710 Scleroderma Diseases 0.000 claims description 4
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 4
• 206010072148 Stiff-Person syndrome Diseases 0.000 claims description 4
• 206010042742 Sympathetic ophthalmia Diseases 0.000 claims description 4
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 208000016644 chronic atrophic gastritis Diseases 0.000 claims description 4
• 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 4
• 230000007882 cirrhosis Effects 0.000 claims description 4
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
• 201000001981 dermatomyositis Diseases 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 208000006454 hepatitis Diseases 0.000 claims description 4
• 201000002364 leukopenia Diseases 0.000 claims description 4
• 231100001022 leukopenia Toxicity 0.000 claims description 4
• 206010025135 lupus erythematosus Diseases 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 206010028417 myasthenia gravis Diseases 0.000 claims description 4
• 208000003786 myxedema Diseases 0.000 claims description 4
• FDRDFLBEJPBZRA-COPCDDAFSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C1=CSC=C1)C1CCCCC1 FDRDFLBEJPBZRA-COPCDDAFSA-N 0.000 claims description 4
• OAGUTUZNQIDKFF-WCSIJFPASA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C=1OC2=CC=CC=C2C=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 OAGUTUZNQIDKFF-WCSIJFPASA-N 0.000 claims description 4
• XSBUJVWUWZIEAX-KEKNWZKVSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]cyclopentanecarboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C1CCCC1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 XSBUJVWUWZIEAX-KEKNWZKVSA-N 0.000 claims description 4
• GVBVQIBCGQKGMR-LBAQZLPGSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]furan-3-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C1=COC=C1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 GVBVQIBCGQKGMR-LBAQZLPGSA-N 0.000 claims description 4
• ZRKKWOQQKZGXCH-ANYOKISRSA-N n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]thiophene-2-carboxamide Chemical compound O=C([C@H](CC1CCCCC1)NC(=O)C=1SC=CC=1)NC(C(C1)=O)CCCN1S(=O)(=O)C1=CC=CC=N1 ZRKKWOQQKZGXCH-ANYOKISRSA-N 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• GVZXSZWCZGKLRS-UHFFFAOYSA-N thieno[3,2-b]thiophene-5-carboxylic acid Chemical compound S1C=CC2=C1C=C(C(=O)O)S2 GVZXSZWCZGKLRS-UHFFFAOYSA-N 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 208000023328 Basedow disease Diseases 0.000 claims description 3
• 208000001204 Hashimoto Disease Diseases 0.000 claims description 3
• 230000003143 atherosclerotic effect Effects 0.000 claims description 3
• STPXQTSZFAJCCI-OIBXWCBGSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC1CCCCC1 STPXQTSZFAJCCI-OIBXWCBGSA-N 0.000 claims description 3
• JXHNSRQLBAFBHR-HOJAQTOUSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]furan-2-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@@H](NC(=O)C=1OC=CC=1)CC1CCCCC1 JXHNSRQLBAFBHR-HOJAQTOUSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• MCVQGZSYZFFKFH-BBMPLOMVSA-N 5-(4-chlorophenyl)-n-[(2s)-3-cyclohexyl-1-oxo-1-[(3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl)amino]propan-2-yl]furan-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N[C@@H](CC2CCCCC2)C(=O)NC2C(CN(CCC2)S(=O)(=O)C=2N=CC=CC=2)=O)O1 MCVQGZSYZFFKFH-BBMPLOMVSA-N 0.000 claims description 2
• MLKCGPSEGXNYGE-BBMPLOMVSA-N FC(F)(F)C1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H](CC2CCCCC2)C(=O)NC2C(CN(CCC2)S(=O)(=O)C=2N=CC=CC=2)=O)=C1 Chemical compound FC(F)(F)C1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H](CC2CCCCC2)C(=O)NC2C(CN(CCC2)S(=O)(=O)C=2N=CC=CC=2)=O)=C1 MLKCGPSEGXNYGE-BBMPLOMVSA-N 0.000 claims description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• IWXKVAKADOQHIQ-QMMLZNLJSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-propylazepan-4-yl]amino]-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C1C[C@@H](C)N(CCC)CC(=O)[C@H]1NC(=O)[C@@H](NC(=O)C1=CSC=C1)CC1CCCCC1 IWXKVAKADOQHIQ-QMMLZNLJSA-N 0.000 claims description 2
• VPVGADBLERRTAG-QDSKXPNFSA-N n-[(2s)-3-cyclohexyl-1-[[(4s,7r)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopropan-2-yl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C(=O)N[C@H]1CC[C@H](N(CC1=O)S(=O)(=O)C=1N=CC=CC=1)C)NC(=O)C=1OC2=CC=CC=C2C=1)C1CCCCC1 VPVGADBLERRTAG-QDSKXPNFSA-N 0.000 claims description 2
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