DK2262364T3 - Oxadiazoanthracenforbindelser for the treatment of diabetes - Google Patents

Info

Publication number

DK2262364T3

DK2262364T3 DK09718287.7T DK09718287T DK2262364T3 DK 2262364 T3 DK2262364 T3 DK 2262364T3 DK 09718287 T DK09718287 T DK 09718287T DK 2262364 T3 DK2262364 T3 DK 2262364T3

Authority

DK

Denmark

Prior art keywords

phenyl

diaza

oxo

oxa

hexahydro

Prior art date

2008-03-07

Links

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• 238000011282 treatment Methods 0.000 title claims description 19
• 206010012601 diabetes mellitus Diseases 0.000 title claims description 7
• 150000001875 compounds Chemical class 0.000 claims description 310
• -1 benzothiopheneyl Chemical group 0.000 claims description 260
• 239000000203 mixture Substances 0.000 claims description 181
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 151
• 125000000217 alkyl group Chemical group 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 150000002148 esters Chemical class 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 41
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 38
• 125000000304 alkynyl group Chemical group 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 229910052717 sulfur Chemical group 0.000 claims description 18
• 239000011593 sulfur Chemical group 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 239000003085 diluting agent Substances 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 13
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• 125000005275 alkylenearyl group Chemical group 0.000 claims description 9
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
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• 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 7
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
• 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims description 6
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 6
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
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• 102000004877 Insulin Human genes 0.000 claims description 4
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• 208000008589 Obesity Diseases 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 206010022489 Insulin Resistance Diseases 0.000 claims description 3
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
• 201000001421 hyperglycemia Diseases 0.000 claims description 3
• 229940125396 insulin Drugs 0.000 claims description 3
• 208000030159 metabolic disease Diseases 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 208000011580 syndromic disease Diseases 0.000 claims description 3
• 206010070901 Diabetic dyslipidaemia Diseases 0.000 claims description 2
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 2
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 2
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
• 206010020772 Hypertension Diseases 0.000 claims description 2
• 235000021229 appetite regulation Nutrition 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
• 230000008991 intestinal motility Effects 0.000 claims description 2
• 229940095574 propionic acid Drugs 0.000 claims 59
• 235000019260 propionic acid Nutrition 0.000 claims 5
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
• CZAQFGAZHXFBLY-IKABJYOBSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(2,6-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C(=CC=CC=2Cl)Cl)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 CZAQFGAZHXFBLY-IKABJYOBSA-N 0.000 claims 1
• VVWHOJKGVMHWRR-UXEWHZQTSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-7-(1,3-thiazol-2-ylmethyl)-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)CC=1SC=CN=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 VVWHOJKGVMHWRR-UXEWHZQTSA-N 0.000 claims 1
• MYTKCZRCSJLNLN-HSFMBMOHSA-N (3s)-8-[[(1s)-1-carboxy-2-[4-(4-cyanophenyl)phenyl]ethyl]carbamoyl]-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-7-carboxylic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(O)=O)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 MYTKCZRCSJLNLN-HSFMBMOHSA-N 0.000 claims 1
• 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
• FSQOYVXHBRURAA-UHFFFAOYSA-N 2-methylsulfanylpyridine-3-carbonitrile Chemical compound CSC1=NC=CC=C1C#N FSQOYVXHBRURAA-UHFFFAOYSA-N 0.000 claims 1
• 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• 238000005265 energy consumption Methods 0.000 claims 1
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• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
• 102220209838 rs1057520382 Human genes 0.000 claims 1
• 238000000034 method Methods 0.000 description 230
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 186
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 163
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• 239000000243 solution Substances 0.000 description 103
• 239000000543 intermediate Substances 0.000 description 95
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
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• 229910052796 boron Inorganic materials 0.000 description 39
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• PKYBIBOHBIYAAU-XJRLVATOSA-N methyl (2s)-2-[[(3s)-3-[4-[[4-chloro-3-(trifluoromethyl)phenyl]methoxy]phenyl]-2-oxo-6,7,8,9-tetrahydro-1h-pyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C1NCC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(C(Cl)=CC=2)C(F)(F)F)=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 PKYBIBOHBIYAAU-XJRLVATOSA-N 0.000 description 2
• QBUJULDFKRVZBW-QGONPRBCSA-N methyl (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-(4-pyridin-4-ylphenyl)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=NC=C1 QBUJULDFKRVZBW-QGONPRBCSA-N 0.000 description 2
• GLGPKPQQVWBNHT-UTLKBRERSA-N methyl (2s)-2-amino-3-(4-pyridin-4-yloxyphenyl)propanoate;dihydrochloride Chemical compound Cl.Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1OC1=CC=NC=C1 GLGPKPQQVWBNHT-UTLKBRERSA-N 0.000 description 2
• YJEMPXNNDQRUNK-TUYUPMGOSA-N methyl (2s)-2-amino-3-[(2s)-2-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-4-methyl-3-oxo-1,4-benzoxazin-6-yl]propanoate;hydrochloride Chemical compound Cl.C1=CC([C@@H]2OC3=CC=C(C=C3N(C)C2=O)C[C@H](N)C(=O)OC)=CC=C1OCC1=CC=C(Cl)C(Cl)=C1 YJEMPXNNDQRUNK-TUYUPMGOSA-N 0.000 description 2
• QWJMMNXUOBFQLN-RSAXXLAASA-N methyl (2s)-2-amino-3-[4-(4-chlorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(Cl)C=C1 QWJMMNXUOBFQLN-RSAXXLAASA-N 0.000 description 2
• FDFQRJWLHKSHPZ-LBPRGKRZSA-N methyl (2s)-3-(4-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CC1=CC=C(Br)C=C1 FDFQRJWLHKSHPZ-LBPRGKRZSA-N 0.000 description 2
• NQIFXJSLCUJHBB-LBPRGKRZSA-N methyl (2s)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CC1=CC=C(O)C=C1 NQIFXJSLCUJHBB-LBPRGKRZSA-N 0.000 description 2
• AGWKPQQUZAALHO-IBGZPJMESA-N methyl (2s)-3-(4-hydroxyphenyl)-2-methyl-2-(phenylmethoxycarbonylamino)propanoate Chemical compound C([C@@](C)(C(=O)OC)NC(=O)OCC=1C=CC=CC=1)C1=CC=C(O)C=C1 AGWKPQQUZAALHO-IBGZPJMESA-N 0.000 description 2
• IHOFASRDFCCYKZ-AHWVRZQESA-N methyl (2s)-3-[(2s)-2-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-3-oxo-4h-1,4-benzoxazin-6-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC([C@@H]2OC3=CC=C(C=C3NC2=O)C[C@@H](C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OCC1=CC=C(Cl)C(Cl)=C1 IHOFASRDFCCYKZ-AHWVRZQESA-N 0.000 description 2
• LPZBAKRLDQQOJI-IGKIAQTJSA-N methyl (2s)-3-[(2s)-2-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-4-methyl-3-oxo-1,4-benzoxazin-6-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC([C@@H]2OC3=CC=C(C=C3N(C)C2=O)C[C@@H](C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OCC1=CC=C(Cl)C(Cl)=C1 LPZBAKRLDQQOJI-IGKIAQTJSA-N 0.000 description 2
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• XVWNPJLPYBSCFI-IKABJYOBSA-N methyl (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-chlorophenyl)phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 XVWNPJLPYBSCFI-IKABJYOBSA-N 0.000 description 1
• OOVDEPZODSXAMU-MERQFXBCSA-N methyl (2s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@](C)(N)CC1=CC=C(O)C=C1 OOVDEPZODSXAMU-MERQFXBCSA-N 0.000 description 1
• RYYDMSMPNITDHP-RSAXXLAASA-N methyl (2s)-2-amino-3-(4-phenylphenyl)propanoate;hydrochloride Chemical compound Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=CC=C1 RYYDMSMPNITDHP-RSAXXLAASA-N 0.000 description 1
• KUYHWWRTSRRQBZ-AWEZNQCLSA-N methyl (2s)-2-amino-3-(4-pyridin-4-ylphenyl)propanoate Chemical compound C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=NC=C1 KUYHWWRTSRRQBZ-AWEZNQCLSA-N 0.000 description 1
• RHZGSWPGNNKTAM-UTLKBRERSA-N methyl (2s)-2-amino-3-(4-pyridin-4-ylphenyl)propanoate;dihydrochloride Chemical compound Cl.Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=NC=C1 RHZGSWPGNNKTAM-UTLKBRERSA-N 0.000 description 1
• SWJBPEXDUCZVHQ-HNNXBMFYSA-N methyl (2s)-2-amino-3-[4-(4-chlorophenyl)phenyl]propanoate Chemical compound C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(Cl)C=C1 SWJBPEXDUCZVHQ-HNNXBMFYSA-N 0.000 description 1
• SEXYDEKFJLXIME-INIZCTEOSA-N methyl (2s)-2-amino-3-[4-(4-cyanophenyl)phenyl]propanoate Chemical compound C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(C#N)C=C1 SEXYDEKFJLXIME-INIZCTEOSA-N 0.000 description 1
• NMCROLOVMHXPSL-HNNXBMFYSA-N methyl (2s)-2-amino-3-[4-(4-fluorophenyl)phenyl]propanoate Chemical compound C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(F)C=C1 NMCROLOVMHXPSL-HNNXBMFYSA-N 0.000 description 1
• VRRRLQSVWDNHDW-RSAXXLAASA-N methyl (2s)-2-amino-3-[4-(4-fluorophenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(F)C=C1 VRRRLQSVWDNHDW-RSAXXLAASA-N 0.000 description 1
• ZXBQZVMJOHLRPQ-INIZCTEOSA-N methyl (2s)-2-amino-3-[4-(4-methoxyphenyl)phenyl]propanoate Chemical compound C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(OC)C=C1 ZXBQZVMJOHLRPQ-INIZCTEOSA-N 0.000 description 1
• HNAUTRSQBWZHGJ-NTISSMGPSA-N methyl (2s)-2-amino-3-[4-(4-methoxyphenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(OC)C=C1 HNAUTRSQBWZHGJ-NTISSMGPSA-N 0.000 description 1
• BOZVHPFMZPKTRE-INIZCTEOSA-N methyl (2s)-2-amino-3-[4-(4-methylphenyl)phenyl]propanoate Chemical compound C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(C)C=C1 BOZVHPFMZPKTRE-INIZCTEOSA-N 0.000 description 1
• NCIPTOKUHQWFBY-NTISSMGPSA-N methyl (2s)-2-amino-3-[4-(4-methylphenyl)phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=CC=C(C)C=C1 NCIPTOKUHQWFBY-NTISSMGPSA-N 0.000 description 1
• NAFOVHMALJGPPY-JTQLQIEISA-N methyl (2s)-3-(4-hydroxy-3-nitrophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CC1=CC=C(O)C([N+]([O-])=O)=C1 NAFOVHMALJGPPY-JTQLQIEISA-N 0.000 description 1
• RKDDZFJGFDOCGH-XJRLVATOSA-N methyl (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(2,5-dichlorophenyl)methoxy]phenyl]-2-oxo-6,7,8,9-tetrahydro-1h-pyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C1NCC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C(=CC=C(Cl)C=2)Cl)=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 RKDDZFJGFDOCGH-XJRLVATOSA-N 0.000 description 1
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