TW202140424A

TW202140424A - Gpr40激動劑

Gpr40激動劑 Download PDF

Info

Publication number: TW202140424A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; compound; pharmaceutically acceptable; formula
Prior art date: 2020-02-28

Application number

TW110106878A

Other languages

English (en)

Chinese (zh)

Inventor

伊亞蘇沙伯哈特

何恕文

西蒙馬弟厄

Original Assignee

美商克力歐普股份有限公司

Priority date

2020-02-28

Filing date

2021-02-26

Publication date

2021-11-01

2021-02-26 Application filed by 美商克力歐普股份有限公司 filed Critical 美商克力歐普股份有限公司

2021-11-01 Publication of TW202140424A publication Critical patent/TW202140424A/zh

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239000000556 agonist Substances 0.000 title claims abstract description 92
101150108864 Ffar1 gene Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 385
102100026148 Free fatty acid receptor 1 Human genes 0.000 claims abstract description 94
101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 claims abstract description 92
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
230000007149 gut brain axis pathway Effects 0.000 claims abstract description 27
208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims abstract description 12
206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims abstract description 12
208000008589 Obesity Diseases 0.000 claims abstract description 9
208000030159 metabolic disease Diseases 0.000 claims abstract description 9
235000020824 obesity Nutrition 0.000 claims abstract description 9
206010049416 Short-bowel syndrome Diseases 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims description 297
239000012453 solvate Substances 0.000 claims description 254
229940002612 prodrug Drugs 0.000 claims description 251
239000000651 prodrug Substances 0.000 claims description 251
125000000217 alkyl group Chemical group 0.000 claims description 197
125000001424 substituent group Chemical group 0.000 claims description 185
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125000001072 heteroaryl group Chemical group 0.000 claims description 143
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 138
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239000001257 hydrogen Substances 0.000 claims description 130
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
-1 -OH Chemical group 0.000 claims description 94
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 90
125000000753 cycloalkyl group Chemical group 0.000 claims description 88
125000003118 aryl group Chemical group 0.000 claims description 87
150000002367 halogens Chemical group 0.000 claims description 81
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 71
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 65
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 62
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125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 49
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239000003814 drug Substances 0.000 claims description 40
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238000000034 method Methods 0.000 claims description 38
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
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230000000694 effects Effects 0.000 claims description 21
238000006467 substitution reaction Methods 0.000 claims description 20
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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 18
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
229940124597 therapeutic agent Drugs 0.000 claims description 15
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230000009885 systemic effect Effects 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
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125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 claims description 7
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229910052794 bromium Inorganic materials 0.000 claims description 7
125000002837 carbocyclic group Chemical group 0.000 claims description 7
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150000001335 aliphatic alkanes Chemical group 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 5
229940090124 dipeptidyl peptidase 4 (dpp-4) inhibitors for blood glucose lowering Drugs 0.000 claims description 5
229940125425 inverse agonist Drugs 0.000 claims description 5
229960003105 metformin Drugs 0.000 claims description 5
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 5
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 5
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
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201000001421 hyperglycemia Diseases 0.000 claims description 4
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 3
AJJISMLYIMQAKP-OAHLLOKOSA-N 5-[4-[(2r)-4-(3-fluoro-4-methylsulfonylphenoxy)butan-2-yl]piperidin-1-yl]-3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C1=NOC(N2CCC(CC2)[C@H](C)CCOC=2C=C(F)C(=CC=2)S(C)(=O)=O)=N1 AJJISMLYIMQAKP-OAHLLOKOSA-N 0.000 claims description 3
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150000002431 hydrogen Chemical class 0.000 claims 8
125000003226 pyrazolyl group Chemical group 0.000 claims 1
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GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 69
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 58
230000002829 reductive effect Effects 0.000 description 52
DGENZVKCTGIDRZ-UHFFFAOYSA-N 3-[4-[(3-phenoxyphenyl)methylamino]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1NCC1=CC=CC(OC=2C=CC=CC=2)=C1 DGENZVKCTGIDRZ-UHFFFAOYSA-N 0.000 description 47
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DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](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=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 8
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
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CAHISRVKQBZLDQ-UHFFFAOYSA-N ethoxyphosphinous acid Chemical compound CCOPO CAHISRVKQBZLDQ-UHFFFAOYSA-N 0.000 description 7
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BBSVTLVUCQRPKU-UHFFFAOYSA-N cyclopropyl-(3-phenylmethoxyphenyl)methanone Chemical compound O=C(C1CC1)c1cccc(OCc2ccccc2)c1 BBSVTLVUCQRPKU-UHFFFAOYSA-N 0.000 description 6
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 6
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