JP2015509510A5 - - Google Patents

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Publication number

JP2015509510A5

JP2015509510A5 JP2014560224A JP2014560224A JP2015509510A5 JP 2015509510 A5 JP2015509510 A5 JP 2015509510A5 JP 2014560224 A JP2014560224 A JP 2014560224A JP 2014560224 A JP2014560224 A JP 2014560224A JP 2015509510 A5 JP2015509510 A5 JP 2015509510A5

Authority

JP

Japan

Prior art keywords

ethyl

hydroxypyrrolidin

methyl

oxo

acetamide

Prior art date

2013-03-05

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.)

Granted

Links

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• -1 cyano, hydroxyl Chemical group 0.000 claims description 136
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 80
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 73
• 150000001875 compounds Chemical class 0.000 claims description 55
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 150000003839 salts Chemical class 0.000 claims description 38
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 102000048260 kappa Opioid Receptors Human genes 0.000 claims description 14
• 108020001588 κ-opioid receptors Proteins 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
• 210000003169 central nervous system Anatomy 0.000 claims description 8
• 102000003840 Opioid Receptors Human genes 0.000 claims description 6
• 108090000137 Opioid Receptors Proteins 0.000 claims description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 239000005711 Benzoic acid Substances 0.000 claims description 5
• 239000000556 agonist Substances 0.000 claims description 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 230000007160 gastrointestinal dysfunction Effects 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 4
• 208000003243 intestinal obstruction Diseases 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• SGVZPNMDWMVUNW-GHTZIAJQSA-N 2-(2,2-dimethyl-3-oxo-4h-1,4-benzothiazin-6-yl)-n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)C(C)(C)SC2=CC=1)C=1C=C(OC(F)(F)F)C=CC=1)N1CC[C@H](O)C1 SGVZPNMDWMVUNW-GHTZIAJQSA-N 0.000 claims description 2
• BLZPUFHLMOHBHZ-GOSISDBHSA-N 2-(2-oxo-3h-1,3-benzothiazol-5-yl)-n-[(1s)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide Chemical compound C([C@@H](NC(CC=1C=C2NC(=O)SC2=CC=1)=O)C=1C=CC=CC=1)N1CCCC1 BLZPUFHLMOHBHZ-GOSISDBHSA-N 0.000 claims description 2
• LYTSGCDUWUHESO-FXAWDEMLSA-N 2-(3,3-difluoro-2-oxo-1h-indol-6-yl)-n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2C(C(C(=O)N2)(F)F)=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 LYTSGCDUWUHESO-FXAWDEMLSA-N 0.000 claims description 2
• OIPIMWKUTPLWFW-AREMUKBSSA-N 2-(3-benzyl-2-oxo-1,3-benzoxazol-5-yl)-n-[(1s)-1-(3-hydroxyphenyl)-2-pyrrolidin-1-ylethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC=3C=CC=CC=3)C(=O)OC2=CC=1)C=1C=C(O)C=CC=1)N1CCCC1 OIPIMWKUTPLWFW-AREMUKBSSA-N 0.000 claims description 2
• ACUMPGYAITXCPN-AHKZPQOWSA-N 2-[3-[(3-cyanophenyl)methyl]-2-oxo-1,3-benzoxazol-5-yl]-n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC=3C=C(C=CC=3)C#N)C(=O)OC2=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 ACUMPGYAITXCPN-AHKZPQOWSA-N 0.000 claims description 2
• QAWDILRRYNWRLE-AZUAARDMSA-N 2-[5-[2-[[(1s)-1-cyclohexyl-2-[(3s)-3-hydroxypyrrolidin-1-yl]ethyl]-methylamino]-2-oxoethyl]-2-oxo-1,3-benzoxazol-3-yl]acetic acid Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC(O)=O)C(=O)OC2=CC=1)C1CCCCC1)N1CC[C@H](O)C1 QAWDILRRYNWRLE-AZUAARDMSA-N 0.000 claims description 2
• LOMPUFLEYCRGRB-PZJWPPBQSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(2-oxo-1,3-dihydroindol-6-yl)acetyl]amino]ethyl]benzoic acid Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CC2=CC=1)C=1C=C(C=CC=1)C(O)=O)N1CC[C@H](O)C1 LOMPUFLEYCRGRB-PZJWPPBQSA-N 0.000 claims description 2
• BOJYGVJQAMBGOA-AZUAARDMSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(3-oxo-4h-1,4-benzothiazin-6-yl)acetyl]amino]ethyl]benzamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CSC2=CC=1)C=1C=C(C=CC=1)C(N)=O)N1CC[C@H](O)C1 BOJYGVJQAMBGOA-AZUAARDMSA-N 0.000 claims description 2
• QVOROBUQQZCPSM-AZUAARDMSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(3-oxo-4h-1,4-benzothiazin-6-yl)acetyl]amino]ethyl]benzoic acid Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CSC2=CC=1)C=1C=C(C=CC=1)C(O)=O)N1CC[C@H](O)C1 QVOROBUQQZCPSM-AZUAARDMSA-N 0.000 claims description 2
• KLJYDDBOUQSYMT-XUZZJYLKSA-N CCN(CC)C(=O)COc1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2sc(=O)[nH]c2c1 Chemical compound CCN(CC)C(=O)COc1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2sc(=O)[nH]c2c1 KLJYDDBOUQSYMT-XUZZJYLKSA-N 0.000 claims description 2
• UCTICLYUGDQTDK-JTHBVZDNSA-N CN(C)C(=O)c1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN(C)C(=O)c1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2CC(=O)Nc2c1 UCTICLYUGDQTDK-JTHBVZDNSA-N 0.000 claims description 2
• BYJFNCGTFBQSSE-MGBGTMOVSA-N CN([C@H](CN1CCCC1)c1cccc(OCc2ccccc2)c1)C(=O)Cc1ccc2oc(=O)n(Cc3ccccc3)c2c1 Chemical compound CN([C@H](CN1CCCC1)c1cccc(OCc2ccccc2)c1)C(=O)Cc1ccc2oc(=O)n(Cc3ccccc3)c2c1 BYJFNCGTFBQSSE-MGBGTMOVSA-N 0.000 claims description 2
• FLBURDBXWCXKHW-YLJYHZDGSA-N CN([C@H](CN1CC[C@@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2oc(=O)[nH]c2c1 Chemical compound CN([C@H](CN1CC[C@@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2oc(=O)[nH]c2c1 FLBURDBXWCXKHW-YLJYHZDGSA-N 0.000 claims description 2
• WEEAIRCTYSPLGL-SIKLNZKXSA-N CN([C@H](CN1CC[C@H](F)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](F)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 WEEAIRCTYSPLGL-SIKLNZKXSA-N 0.000 claims description 2
• YLWCSTGKLCPTPI-PZJWPPBQSA-N CN([C@H](CN1CC[C@H](F)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](F)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2CC(=O)Nc2c1 YLWCSTGKLCPTPI-PZJWPPBQSA-N 0.000 claims description 2
• HIKJOZMEOICVPB-SIKLNZKXSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 HIKJOZMEOICVPB-SIKLNZKXSA-N 0.000 claims description 2
• QDPYEFQBGAUFDH-SIKLNZKXSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2NC(=O)Cc2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2NC(=O)Cc2c1 QDPYEFQBGAUFDH-SIKLNZKXSA-N 0.000 claims description 2
• GDNKHKZTQMVGCK-AZUAARDMSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2OCC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2OCC(=O)Nc2c1 GDNKHKZTQMVGCK-AZUAARDMSA-N 0.000 claims description 2
• IFOUKQQRZCJINU-AZUAARDMSA-N CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(CC(O)=O)c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(CC(O)=O)c2c1 IFOUKQQRZCJINU-AZUAARDMSA-N 0.000 claims description 2
• HPLCKHUKWVLQLI-AZGAKELHSA-N CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(Cc3cccc(c3)-c3nn[nH]n3)c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(Cc3cccc(c3)-c3nn[nH]n3)c2c1 HPLCKHUKWVLQLI-AZGAKELHSA-N 0.000 claims description 2
• MJDXDYJOADNCJR-UHFFFAOYSA-N Cl.CN(C(CN1CCCC1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound Cl.CN(C(CN1CCCC1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 MJDXDYJOADNCJR-UHFFFAOYSA-N 0.000 claims description 2
• NGUMEXYEHGUXDT-FSRHSHDFSA-N Cl.OC(=O)COc1cccc(c1)[C@@H](CN1CCCC1)NC(=O)Cc1ccc2oc(=O)[nH]c2c1 Chemical compound Cl.OC(=O)COc1cccc(c1)[C@@H](CN1CCCC1)NC(=O)Cc1ccc2oc(=O)[nH]c2c1 NGUMEXYEHGUXDT-FSRHSHDFSA-N 0.000 claims description 2
• CWTCHUFBPAOJFU-GMUIIQOCSA-N Cl.OC(=O)Cn1c2cc(CC(=O)N[C@H](CN3CCCC3)c3ccccc3)ccc2oc1=O Chemical compound Cl.OC(=O)Cn1c2cc(CC(=O)N[C@H](CN3CCCC3)c3ccccc3)ccc2oc1=O CWTCHUFBPAOJFU-GMUIIQOCSA-N 0.000 claims description 2
• IKEWDDJBOFQKQK-UHFFFAOYSA-N OC(=O)COc1cccc(c1)C(CN1CCCC1)NC(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound OC(=O)COc1cccc(c1)C(CN1CCCC1)NC(=O)Cc1ccc2CC(=O)Nc2c1 IKEWDDJBOFQKQK-UHFFFAOYSA-N 0.000 claims description 2
• IKKGXDNOHGKYEX-LZAGWAHOSA-N [O-]C(=O)C(F)(F)F.CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2[NH2+]S(=O)(=O)Cc2c1 Chemical compound [O-]C(=O)C(F)(F)F.CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2[NH2+]S(=O)(=O)Cc2c1 IKKGXDNOHGKYEX-LZAGWAHOSA-N 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• BMBANPOHPFKVTA-UHFFFAOYSA-N benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CC=CC=C1 BMBANPOHPFKVTA-UHFFFAOYSA-N 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 2
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• OPCUHICXVGFAAO-PZJWPPBQSA-N n-[(1s)-1-(3-ethynylphenyl)-2-[(3s)-3-hydroxypyrrolidin-1-yl]ethyl]-n-methyl-2-(2-oxo-3h-1,3-benzothiazol-5-yl)acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)SC2=CC=1)C=1C=C(C=CC=1)C#C)N1CC[C@H](O)C1 OPCUHICXVGFAAO-PZJWPPBQSA-N 0.000 claims description 2
• AVYAYWUTODIOFY-AZGAKELHSA-N n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methyl-2-[2-oxo-3-[[4-(2h-tetrazol-5-yl)phenyl]methyl]-1,3-benzoxazol-5-yl]acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC=3C=CC(=CC=3)C3=NNN=N3)C(=O)OC2=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 AVYAYWUTODIOFY-AZGAKELHSA-N 0.000 claims description 2
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 2
• FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
• 239000000203 mixture Substances 0.000 claims 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• SMXZZNJEHDKCKX-PZJWPPBQSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(2-oxo-1,3-dihydroindol-6-yl)acetyl]amino]ethyl]benzamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CC2=CC=1)C=1C=C(C=CC=1)C(N)=O)N1CC[C@H](O)C1 SMXZZNJEHDKCKX-PZJWPPBQSA-N 0.000 claims 1
• 230000021615 conjugation Effects 0.000 claims 1
• XAVBRHQYBNDKED-PZJWPPBQSA-N n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methyl-2-(2-oxo-1,3-dihydroindol-6-yl)acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CC2=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 XAVBRHQYBNDKED-PZJWPPBQSA-N 0.000 claims 1
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
• 125000001107 pteroylglutamyl group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 description 18
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
• 0 CCC(CCN(C[C@](*)C(C)N(*)C(C(*)(*)*)=O)C1)[C@@]1O Chemical compound CCC(CCN(C[C@](*)C(C)N(*)C(C(*)(*)*)=O)C1)[C@@]1O 0.000 description 1
• JKTYNWTVBPFVDU-PGRDOPGGSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2ncc(=O)[nH]c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2ncc(=O)[nH]c2c1 JKTYNWTVBPFVDU-PGRDOPGGSA-N 0.000 description 1
• YAVDEXADPNAAAM-PKOBYXMFSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2oc(=O)[nH]c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2oc(=O)[nH]c2c1 YAVDEXADPNAAAM-PKOBYXMFSA-N 0.000 description 1
• LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 1