HRP20050212A2 - N-substituted-1h-indol-5-propionic acid compounds as ppar agonists useful for the treatment of diabetes - Google Patents

Info

Publication number

HRP20050212A2

HRP20050212A2 HR20050212A HRP20050212A HRP20050212A2 HR P20050212 A2 HRP20050212 A2 HR P20050212A2 HR 20050212 A HR20050212 A HR 20050212A HR P20050212 A HRP20050212 A HR P20050212A HR P20050212 A2 HRP20050212 A2 HR P20050212A2

Authority

HR

Croatia

Prior art keywords

methyl

indol

phenyl

ethoxy

propanoic acid

Prior art date

2002-09-12

Links

• Espacenet
• Global Dossier
• Discuss

• -1 N-substituted-1h-indol-5-propionic acid compounds Chemical class 0.000 title claims description 69
• 238000011282 treatment Methods 0.000 title claims description 45
• 206010012601 diabetes mellitus Diseases 0.000 title claims description 16
• 239000000556 agonist Substances 0.000 title claims description 12
• 101150014691 PPARA gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 238
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 150000002148 esters Chemical class 0.000 claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 238000000034 method Methods 0.000 claims description 79
• 238000002360 preparation method Methods 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 238000006243 chemical reaction Methods 0.000 claims description 40
• 239000002253 acid Substances 0.000 claims description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 150000002431 hydrogen Chemical class 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 26
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 22
• 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 22
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 19
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 19
• 102000023984 PPAR alpha Human genes 0.000 claims description 18
• 102000000536 PPAR gamma Human genes 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 108010016731 PPAR gamma Proteins 0.000 claims description 17
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 17
• 238000011321 prophylaxis Methods 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 15
• 229960001243 orlistat Drugs 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 239000001301 oxygen Substances 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 239000011593 sulfur Substances 0.000 claims description 14
• 229940079593 drug Drugs 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 150000002632 lipids Chemical class 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 102000004877 Insulin Human genes 0.000 claims description 11
• 108090001061 Insulin Proteins 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 230000036772 blood pressure Effects 0.000 claims description 11
• 150000002367 halogens Chemical group 0.000 claims description 11
• 229940125396 insulin Drugs 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 10
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 10
• 230000003143 atherosclerotic effect Effects 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
• PAWOPJKHTZCKMT-QFIPXVFZSA-N (2s)-3-(1-{[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}-1h-indol-5-yl)-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1Cl PAWOPJKHTZCKMT-QFIPXVFZSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• ZYXIXLCLHFATLN-QFIPXVFZSA-N (2s)-2-ethoxy-3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 ZYXIXLCLHFATLN-QFIPXVFZSA-N 0.000 claims description 5
• PMZZWDLQGMUYFU-DEOSSOPVSA-N (2s)-3-[1-[[2-(3,5-dimethoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC(OC)=CC(OC)=C1 PMZZWDLQGMUYFU-DEOSSOPVSA-N 0.000 claims description 5
• HNJWXXUWEWHCGB-UHFFFAOYSA-N 2-but-3-enoxy-3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound N=1C(CN2C3=CC=C(CC(OCCC=C)C(O)=O)C=C3C=C2)=C(C)OC=1C1=CC=C(C(F)(F)F)C=C1 HNJWXXUWEWHCGB-UHFFFAOYSA-N 0.000 claims description 5
• BAGMLPPSRATBGO-UHFFFAOYSA-N 2-ethoxy-3-[4-methyl-1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=C(C)C(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(C)C)C=C1 BAGMLPPSRATBGO-UHFFFAOYSA-N 0.000 claims description 5
• 241000282414 Homo sapiens Species 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 238000005984 hydrogenation reaction Methods 0.000 claims description 5
• MMOLYSUHEKSQBL-QHCPKHFHSA-N (2s)-2-ethoxy-3-[1-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=CC2=CC(C[C@H](OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(F)C(C)=C1 MMOLYSUHEKSQBL-QHCPKHFHSA-N 0.000 claims description 4
• KWGGIRZLUSNBCK-UHFFFAOYSA-N 2-ethoxy-3-[3-methyl-1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 KWGGIRZLUSNBCK-UHFFFAOYSA-N 0.000 claims description 4
• HWGSDOIOQSFRBG-UHFFFAOYSA-N 3-[1-[[2-(2-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl]-3-methylindol-5-yl]-2-ethoxypropanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=CC=C1Cl HWGSDOIOQSFRBG-UHFFFAOYSA-N 0.000 claims description 4
• SNELYVVCHDOVFP-UHFFFAOYSA-N 3-[1-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]indol-5-yl]-2-propoxypropanoic acid Chemical compound C1=CC2=CC(CC(OCCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 SNELYVVCHDOVFP-UHFFFAOYSA-N 0.000 claims description 4
• 239000013543 active substance Substances 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 239000001294 propane Substances 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
• 239000007787 solid Substances 0.000 description 67
• 239000002904 solvent Substances 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 47
• 239000000203 mixture Substances 0.000 description 46
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• 125000004494 ethyl ester group Chemical group 0.000 description 37
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 239000003921 oil Substances 0.000 description 34
• 235000019198 oils Nutrition 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• XINZHRGAVPPNEM-UHFFFAOYSA-N ethyl 2-ethoxy-3-(1h-indol-5-yl)propanoate Chemical compound CCOC(=O)C(OCC)CC1=CC=C2NC=CC2=C1 XINZHRGAVPPNEM-UHFFFAOYSA-N 0.000 description 28
• 239000000243 solution Substances 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 235000019439 ethyl acetate Nutrition 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
• 238000010992 reflux Methods 0.000 description 22
• SBNOTUDDIXOFSN-UHFFFAOYSA-N 1h-indole-2-carbaldehyde Chemical compound C1=CC=C2NC(C=O)=CC2=C1 SBNOTUDDIXOFSN-UHFFFAOYSA-N 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 20
• 239000000741 silica gel Substances 0.000 description 20
• 229910002027 silica gel Inorganic materials 0.000 description 20
• 230000002349 favourable effect Effects 0.000 description 19
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• 239000003480 eluent Substances 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
• 238000004587 chromatography analysis Methods 0.000 description 17
• 239000012074 organic phase Substances 0.000 description 17
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 239000011575 calcium Substances 0.000 description 15
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 14
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• 238000003756 stirring Methods 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 229910052740 iodine Inorganic materials 0.000 description 13
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 13
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• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 11
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
• 239000012230 colorless oil Substances 0.000 description 11
• VPTSNEVSXPLIOD-UHFFFAOYSA-N ethyl 2-ethoxy-3-(2-methyl-1h-indol-5-yl)propanoate Chemical compound CCOC(=O)C(OCC)CC1=CC=C2NC(C)=CC2=C1 VPTSNEVSXPLIOD-UHFFFAOYSA-N 0.000 description 11
• 150000002475 indoles Chemical class 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• ADZUEEUKBYCSEY-UHFFFAOYSA-N 1h-indole-5-carbaldehyde Chemical class O=CC1=CC=C2NC=CC2=C1 ADZUEEUKBYCSEY-UHFFFAOYSA-N 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• HDACOSTZHYDFHU-ZDUSSCGKSA-N methyl (2s)-2-ethoxy-3-(1h-indol-5-yl)propanoate Chemical compound CCO[C@H](C(=O)OC)CC1=CC=C2NC=CC2=C1 HDACOSTZHYDFHU-ZDUSSCGKSA-N 0.000 description 10
• 150000003556 thioamides Chemical class 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
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• MMJCDOWKUCLEQX-UHFFFAOYSA-M (1,2-diethoxy-2-oxoethyl)-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C(=O)OCC)OCC)C1=CC=CC=C1 MMJCDOWKUCLEQX-UHFFFAOYSA-M 0.000 description 8
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• 150000003138 primary alcohols Chemical class 0.000 description 8
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
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• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 6
• SRGMASRXXKNDLX-UHFFFAOYSA-N 2-ethoxy-3-[3-methyl-1-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methyl]indol-5-yl]propanoic acid Chemical compound C1=C(C)C2=CC(CC(OCC)C(O)=O)=CC=C2N1CC(=C(O1)C)N=C1C1=CC=C(C(C)C)C=C1 SRGMASRXXKNDLX-UHFFFAOYSA-N 0.000 description 6
• HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 6
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