NZ549716A - Pyrimidin-dione derivatives as dipeptidyl peptidase inhibitors - Google Patents

Info

Publication number

NZ549716A

NZ549716A NZ549716A NZ54971604A NZ549716A NZ 549716 A NZ549716 A NZ 549716A NZ 549716 A NZ549716 A NZ 549716A NZ 54971604 A NZ54971604 A NZ 54971604A NZ 549716 A NZ549716 A NZ 549716A

Authority

NZ

New Zealand

Prior art keywords

alkyl

phenyl

amino

group

piperidin

Prior art date

2004-03-15

Links

• Espacenet
• Global Dossier
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• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title claims description 19
• 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 title description 9
• 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 title description 9
• 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 344
• 238000004519 manufacturing process Methods 0.000 claims abstract description 27
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
• 201000011510 cancer Diseases 0.000 claims abstract description 7
• 210000004698 lymphocyte Anatomy 0.000 claims abstract description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
• 230000020411 cell activation Effects 0.000 claims abstract description 6
• 208000031886 HIV Infections Diseases 0.000 claims abstract description 4
• 208000024891 symptom Diseases 0.000 claims abstract description 4
• 208000037357 HIV infectious disease Diseases 0.000 claims abstract description 3
• 206010061598 Immunodeficiency Diseases 0.000 claims abstract description 3
• 208000029462 Immunodeficiency disease Diseases 0.000 claims abstract description 3
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 3
• 230000007813 immunodeficiency Effects 0.000 claims abstract description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 596
• -1 (C9-i2)bicycloaryl Chemical group 0.000 claims description 321
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 290
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 197
• 125000001072 heteroaryl group Chemical group 0.000 claims description 163
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 162
• 125000003118 aryl group Chemical group 0.000 claims description 153
• 239000000203 mixture Substances 0.000 claims description 146
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 143
• 125000005842 heteroatom Chemical group 0.000 claims description 137
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 130
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 122
• 125000003545 alkoxy group Chemical group 0.000 claims description 97
• 238000000034 method Methods 0.000 claims description 92
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 89
• 125000004104 aryloxy group Chemical group 0.000 claims description 88
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 79
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 74
• 239000001257 hydrogen Substances 0.000 claims description 70
• 229910052739 hydrogen Inorganic materials 0.000 claims description 70
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 69
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 69
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 54
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 54
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 53
• 201000010099 disease Diseases 0.000 claims description 53
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 52
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 125000004429 atom Chemical group 0.000 claims description 43
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 33
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 32
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 32
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 32
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 31
• 230000008569 process Effects 0.000 claims description 31
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• 238000009472 formulation Methods 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 238000000926 separation method Methods 0.000 claims description 23
• 239000002904 solvent Substances 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
• 125000005647 linker group Chemical group 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 125000001475 halogen functional group Chemical group 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 239000003960 organic solvent Substances 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 239000005022 packaging material Substances 0.000 claims description 13
• 125000006413 ring segment Chemical group 0.000 claims description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 108090000623 proteins and genes Proteins 0.000 claims description 12
• 102000004169 proteins and genes Human genes 0.000 claims description 12
• 150000003335 secondary amines Chemical class 0.000 claims description 12
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
• 239000007787 solid Substances 0.000 claims description 10
• 150000003512 tertiary amines Chemical class 0.000 claims description 10
• 230000015572 biosynthetic process Effects 0.000 claims description 9
• 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 9
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
• 238000003860 storage Methods 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 claims description 7
• 238000007911 parenteral administration Methods 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
• 238000000746 purification Methods 0.000 claims description 6
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
• WKSHWJJTTMKYRY-UHFFFAOYSA-N 2-[[6-(3-aminopiperidin-1-yl)-3-(1h-benzimidazol-2-ylmethyl)-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1C(N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=NC2=CC=CC=C2N1 WKSHWJJTTMKYRY-UHFFFAOYSA-N 0.000 claims description 5
• RTNHKNRRDBDENT-GFCCVEGCSA-N 6-[(3r)-3-aminopiperidin-1-yl]-1-[(2-bromophenyl)methyl]pyrimidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=CC(=O)NC(=O)N1CC1=CC=CC=C1Br RTNHKNRRDBDENT-GFCCVEGCSA-N 0.000 claims description 5
• PKUFNWPSFCOSLU-UHFFFAOYSA-N 6-chloro-1h-pyrimidine-2,4-dione Chemical compound ClC1=CC(=O)NC(=O)N1 PKUFNWPSFCOSLU-UHFFFAOYSA-N 0.000 claims description 5
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
• JTRLDOQRNPDZPC-XMMPIXPASA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-2,4-dioxo-3-[(3-pyrrol-1-ylphenyl)methyl]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=CC(N2C=CC=C2)=C1 JTRLDOQRNPDZPC-XMMPIXPASA-N 0.000 claims description 4
• KVIRZRAVCGZEMX-JOCHJYFZSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-[(2-cyanophenyl)methyl]-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=CC=C1C#N KVIRZRAVCGZEMX-JOCHJYFZSA-N 0.000 claims description 4
• OYCQUHWGCMEPNI-JOCHJYFZSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-[(4-cyanophenyl)methyl]-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=C(C#N)C=C1 OYCQUHWGCMEPNI-JOCHJYFZSA-N 0.000 claims description 4
• DRSHNENJAZVBLE-CQSZACIVSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-5-chloro-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C(Cl)=C1N1CCC[C@@H](N)C1 DRSHNENJAZVBLE-CQSZACIVSA-N 0.000 claims description 4
• GZBXRROZKDWTHE-CYBMUJFWSA-N 6-[(3r)-3-aminopiperidin-1-yl]-1-[(2-bromo-5-fluorophenyl)methyl]-3-methylpyrimidine-2,4-dione Chemical compound C=1C(F)=CC=C(Br)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 GZBXRROZKDWTHE-CYBMUJFWSA-N 0.000 claims description 4
• ZOZBXLMDTJHPKM-CYBMUJFWSA-N 6-[(3r)-3-aminopiperidin-1-yl]-1-[(2-bromophenyl)methyl]-3-methylpyrimidine-2,4-dione Chemical compound C=1C=CC=C(Br)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZOZBXLMDTJHPKM-CYBMUJFWSA-N 0.000 claims description 4
• MTYQPWCBXKEMEF-CYBMUJFWSA-N 6-[(3r)-3-aminopiperidin-1-yl]-1-[(2-chloro-4-fluorophenyl)methyl]-3-methylpyrimidine-2,4-dione Chemical compound C=1C=C(F)C=C(Cl)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 MTYQPWCBXKEMEF-CYBMUJFWSA-N 0.000 claims description 4
• SHWTVSFPUGCFIH-GFCCVEGCSA-N 6-[(3r)-3-aminopiperidin-1-yl]-1-[(2-iodophenyl)methyl]pyrimidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C1=CC(=O)NC(=O)N1CC1=CC=CC=C1I SHWTVSFPUGCFIH-GFCCVEGCSA-N 0.000 claims description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
• 238000004587 chromatography analysis Methods 0.000 claims description 4
• 238000004440 column chromatography Methods 0.000 claims description 4
• 239000012669 liquid formulation Substances 0.000 claims description 4
• LOMSDFFGKJNOEH-JOCHJYFZSA-N methyl 3-[[4-[(3r)-3-aminopiperidin-1-yl]-3-[(2-cyanophenyl)methyl]-2,6-dioxopyrimidin-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C(N(CC=3C(=CC=CC=3)C#N)C(N3C[C@H](N)CCC3)=CC2=O)=O)=C1 LOMSDFFGKJNOEH-JOCHJYFZSA-N 0.000 claims description 4
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
• 238000005406 washing Methods 0.000 claims description 4
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 3
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
• JTRLDOQRNPDZPC-UHFFFAOYSA-N 2-[[6-(3-aminopiperidin-1-yl)-2,4-dioxo-3-[(3-pyrrol-1-ylphenyl)methyl]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1C(N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=CC(N2C=CC=C2)=C1 JTRLDOQRNPDZPC-UHFFFAOYSA-N 0.000 claims description 3
• GMTUWIWFYIFDEX-UHFFFAOYSA-N 2-[[6-(3-aminopiperidin-1-yl)-2,4-dioxo-3-[(4-pyrazol-1-ylphenyl)methyl]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1C(N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=C(N2N=CC=C2)C=C1 GMTUWIWFYIFDEX-UHFFFAOYSA-N 0.000 claims description 3
• KYXUNUKTHMZSLE-UHFFFAOYSA-N 2-[[6-(3-aminopiperidin-1-yl)-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1C(N)CCCN1C1=CC(=O)NC(=O)N1CC1=CC=CC=C1C#N KYXUNUKTHMZSLE-UHFFFAOYSA-N 0.000 claims description 3
• JJTMVXIGKYTDHI-UHFFFAOYSA-N 2-[[6-(3-aminopiperidin-1-yl)-3-[(3-cyanophenyl)methyl]-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1C(N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=CC(C#N)=C1 JJTMVXIGKYTDHI-UHFFFAOYSA-N 0.000 claims description 3
• DRSHNENJAZVBLE-UHFFFAOYSA-N 2-[[6-(3-aminopiperidin-1-yl)-5-chloro-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C(Cl)=C1N1CCCC(N)C1 DRSHNENJAZVBLE-UHFFFAOYSA-N 0.000 claims description 3
• GMTUWIWFYIFDEX-HSZRJFAPSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-2,4-dioxo-3-[(4-pyrazol-1-ylphenyl)methyl]pyrimidin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=C(N2N=CC=C2)C=C1 GMTUWIWFYIFDEX-HSZRJFAPSA-N 0.000 claims description 3
• NOKFOTRWCQJAKB-MRXNPFEDSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-ethyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(CC)C(=O)C=C1N1CCC[C@@H](N)C1 NOKFOTRWCQJAKB-MRXNPFEDSA-N 0.000 claims description 3
• QWCRMWNCTSFODM-CYBMUJFWSA-N 2-[[6-[(3r)-3-aminopiperidin-1-yl]-5-chloro-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C1[C@H](N)CCCN1C1=C(Cl)C(=O)NC(=O)N1CC1=CC=CC=C1C#N QWCRMWNCTSFODM-CYBMUJFWSA-N 0.000 claims description 3
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 3
• UZCQJGIZQLXZPF-UHFFFAOYSA-N 3-[[4-(3-aminopiperidin-1-yl)-3-[(2-cyanophenyl)methyl]-2,6-dioxopyrimidin-1-yl]methyl]benzoic acid Chemical compound C1C(N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=CC(C(O)=O)=C1 UZCQJGIZQLXZPF-UHFFFAOYSA-N 0.000 claims description 3
• UZCQJGIZQLXZPF-OAQYLSRUSA-N 3-[[4-[(3r)-3-aminopiperidin-1-yl]-3-[(2-cyanophenyl)methyl]-2,6-dioxopyrimidin-1-yl]methyl]benzoic acid Chemical compound C1[C@H](N)CCCN1C(N(C1=O)CC=2C(=CC=CC=2)C#N)=CC(=O)N1CC1=CC=CC(C(O)=O)=C1 UZCQJGIZQLXZPF-OAQYLSRUSA-N 0.000 claims description 3
• ZOZBXLMDTJHPKM-UHFFFAOYSA-N 6-(3-aminopiperidin-1-yl)-1-[(2-bromophenyl)methyl]-3-methylpyrimidine-2,4-dione Chemical compound C=1C=CC=C(Br)C=1CN1C(=O)N(C)C(=O)C=C1N1CCCC(N)C1 ZOZBXLMDTJHPKM-UHFFFAOYSA-N 0.000 claims description 3
• RTNHKNRRDBDENT-UHFFFAOYSA-N 6-(3-aminopiperidin-1-yl)-1-[(2-bromophenyl)methyl]pyrimidine-2,4-dione Chemical compound C1C(N)CCCN1C1=CC(=O)NC(=O)N1CC1=CC=CC=C1Br RTNHKNRRDBDENT-UHFFFAOYSA-N 0.000 claims description 3
• MTYQPWCBXKEMEF-UHFFFAOYSA-N 6-(3-aminopiperidin-1-yl)-1-[(2-chloro-4-fluorophenyl)methyl]-3-methylpyrimidine-2,4-dione Chemical compound C=1C=C(F)C=C(Cl)C=1CN1C(=O)N(C)C(=O)C=C1N1CCCC(N)C1 MTYQPWCBXKEMEF-UHFFFAOYSA-N 0.000 claims description 3
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
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