AU2011237775A1 - Modulators of the GPR119 receptor and the treatment of disorders related thereto - Google Patents

Info

Publication number

AU2011237775A1

AU2011237775A1 AU2011237775A AU2011237775A AU2011237775A1 AU 2011237775 A1 AU2011237775 A1 AU 2011237775A1 AU 2011237775 A AU2011237775 A AU 2011237775A AU 2011237775 A AU2011237775 A AU 2011237775A AU 2011237775 A1 AU2011237775 A1 AU 2011237775A1

Authority

AU

Australia

Prior art keywords

group

cyclohexyloxy

methylsulfonyl

alkyl

yloxy

Prior art date

2010-04-06

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 135
• 238000011282 treatment Methods 0.000 title claims abstract description 26
• 208000035475 disorder Diseases 0.000 title description 75
• 102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 title description 7
• 101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 302
• 150000003839 salts Chemical class 0.000 claims abstract description 97
• 239000012453 solvate Substances 0.000 claims abstract description 92
• 150000004677 hydrates Chemical class 0.000 claims abstract description 89
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 46
• 208000008589 Obesity Diseases 0.000 claims abstract description 45
• 235000020824 obesity Nutrition 0.000 claims abstract description 44
• 210000004369 blood Anatomy 0.000 claims abstract description 39
• 239000008280 blood Substances 0.000 claims abstract description 39
• 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims abstract description 35
• 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims abstract description 35
• 239000000859 incretin Substances 0.000 claims abstract description 34
• 239000003112 inhibitor Substances 0.000 claims abstract description 33
• MGXWVYUBJRZYPE-YUGYIWNOSA-N incretin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=C(O)C=C1 MGXWVYUBJRZYPE-YUGYIWNOSA-N 0.000 claims abstract description 32
• 230000002503 metabolic effect Effects 0.000 claims abstract description 24
• 229940123208 Biguanide Drugs 0.000 claims abstract description 22
• 230000001668 ameliorated effect Effects 0.000 claims abstract description 21
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims abstract description 20
• 239000003888 alpha glucosidase inhibitor Substances 0.000 claims abstract description 20
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims abstract description 19
• 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 claims abstract description 19
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 989
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 259
• 125000000217 alkyl group Chemical group 0.000 claims description 233
• 229910052799 carbon Inorganic materials 0.000 claims description 157
• 229910052739 hydrogen Inorganic materials 0.000 claims description 155
• 125000001424 substituent group Chemical group 0.000 claims description 155
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 143
• 125000000623 heterocyclic group Chemical group 0.000 claims description 126
• 229910052736 halogen Inorganic materials 0.000 claims description 114
• 150000002367 halogens Chemical class 0.000 claims description 114
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 112
• 239000008177 pharmaceutical agent Substances 0.000 claims description 111
• 125000001072 heteroaryl group Chemical group 0.000 claims description 106
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 102
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 102
• 239000000203 mixture Substances 0.000 claims description 90
• 125000001188 haloalkyl group Chemical group 0.000 claims description 87
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 73
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 65
• 238000000034 method Methods 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 57
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 50
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 48
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 47
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 47
• 229940127557 pharmaceutical product Drugs 0.000 claims description 47
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• 238000002360 preparation method Methods 0.000 claims description 42
• 102100021198 Chemerin-like receptor 2 Human genes 0.000 claims description 40
• 101000750094 Homo sapiens Chemerin-like receptor 2 Proteins 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 102000005962 receptors Human genes 0.000 claims description 39
• 108020003175 receptors Proteins 0.000 claims description 39
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
• 125000001153 fluoro group Chemical group F* 0.000 claims description 35
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims description 31
• 239000002552 dosage form Substances 0.000 claims description 28
• 210000000988 bone and bone Anatomy 0.000 claims description 27
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
• 238000009472 formulation Methods 0.000 claims description 26
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 24
• 239000003937 drug carrier Substances 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 22
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 22
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 21
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 21
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 20
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 19
• 208000012902 Nervous system disease Diseases 0.000 claims description 19
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 19
• 238000004519 manufacturing process Methods 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 18
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 17
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 17
• 229940100389 Sulfonylurea Drugs 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 229950004994 meglitinide Drugs 0.000 claims description 17
• 241001465754 Metazoa Species 0.000 claims description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 14
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 13
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims description 13
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 13
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 12
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 11
• 238000002560 therapeutic procedure Methods 0.000 claims description 11
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 11
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 10
• ZMLHBBXPXZXTSP-UHFFFAOYSA-N 2-fluoropropane Chemical group C[C](C)F ZMLHBBXPXZXTSP-UHFFFAOYSA-N 0.000 claims description 8
• 150000007942 carboxylates Chemical class 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 claims description 4
• FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims description 4
• XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 claims description 4
• 229960004111 buformin Drugs 0.000 claims description 4
• PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 claims description 4
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
• ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 claims description 4
• JVHXJTBJCFBINQ-ADAARDCZSA-N Dapagliflozin Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=C1Cl JVHXJTBJCFBINQ-ADAARDCZSA-N 0.000 claims description 3
• LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 claims description 3
• 150000004283 biguanides Chemical class 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 claims description 3
• ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims description 3
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 3
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims description 3
• 102000004366 Glucosidases Human genes 0.000 claims description 2
• 108010056771 Glucosidases Proteins 0.000 claims description 2
• SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 2
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 2
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 33
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
• 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 2
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
• NVVSPGQEXMJZIR-BMIGLBTASA-N (1s,6r)-3-{[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]carbonyl}-6-(2,4,5-trifluorophenyl)cyclohex-3-en-1-amine Chemical compound C1([C@H]2CC=C(C[C@@H]2N)C(=O)N2CC=3N(C(=NN=3)C(F)(F)F)CC2)=CC(F)=C(F)C=C1F NVVSPGQEXMJZIR-BMIGLBTASA-N 0.000 claims 1
• OELFLUMRDSZNSF-OFLPRAFFSA-N (2R)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid Chemical compound C1CC(C(C)C)CCC1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-OFLPRAFFSA-N 0.000 claims 1
• QYRWMYNQCXSWLV-INIZCTEOSA-N (2s)-1-[2-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCNCC(=O)N1CCC[C@H]1C#N QYRWMYNQCXSWLV-INIZCTEOSA-N 0.000 claims 1
• AEOKIJDXJROCJQ-KRWDZBQOSA-N (2s)-1-[2-[[2-methyl-4-(4-pyridin-3-ylimidazol-1-yl)butan-2-yl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC(C)(C)CCN(C=1)C=NC=1C1=CC=CN=C1 AEOKIJDXJROCJQ-KRWDZBQOSA-N 0.000 claims 1
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
• UOCHFMVPMIYRHJ-QWRGUYRKSA-N 1-[(3s,4s)-4-amino-1-[4-(3,3-difluoropyrrolidin-1-yl)-1,3,5-triazin-2-yl]pyrrolidin-3-yl]-5,5-difluoropiperidin-2-one Chemical compound N1([C@H]2CN(C[C@@H]2N)C=2N=C(N=CN=2)N2CC(F)(F)CC2)CC(F)(F)CCC1=O UOCHFMVPMIYRHJ-QWRGUYRKSA-N 0.000 claims 1
• LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims 1
• GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 claims 1
• BZGNTNQTQLGDMX-UHFFFAOYSA-N 2-methyl-6-methylsulfonylpyridine Chemical compound CC1=CC=CC(S(C)(=O)=O)=N1 BZGNTNQTQLGDMX-UHFFFAOYSA-N 0.000 claims 1
• WIGIZIANZCJQQY-UHFFFAOYSA-N 4-ethyl-3-methyl-N-[2-[4-[[[(4-methylcyclohexyl)amino]-oxomethyl]sulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCC(C)CC2)C=C1 WIGIZIANZCJQQY-UHFFFAOYSA-N 0.000 claims 1
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