IL302219A

IL302219A - Modulators of the integrated stress response pathway

Modulators of the integrated stress response pathway

Info

Publication number: IL302219A
Authority: IL; Israel
Prior art keywords: oxadiazol; ethoxy; trifluoromethoxy; piperidine; tert
Prior art date: 2020-10-22

Application number

IL302219A

Other languages

English (en)

Hebrew (he)

Original Assignee

Evotec Int Gmbh

Priority date

2020-10-22

Filing date

2021-10-21

Publication date

2023-06-01

2021-10-21 Application filed by Evotec Int Gmbh filed Critical Evotec Int Gmbh

2023-06-01 Publication of IL302219A publication Critical patent/IL302219A/en

Links

230000009221 stress response pathway Effects 0.000 title description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 200
150000001875 compounds Chemical class 0.000 claims description 157
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 133
-1 C2-alkenyl Chemical group 0.000 claims description 101
150000003839 salts Chemical class 0.000 claims description 56
238000000034 method Methods 0.000 claims description 52
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 52
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 48
BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims description 46
239000012453 solvate Substances 0.000 claims description 43
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical group 0.000 claims description 36
229910052799 carbon Inorganic materials 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 34
125000006413 ring segment Chemical group 0.000 claims description 33
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
201000010099 disease Diseases 0.000 claims description 31
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 29
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 23
239000008194 pharmaceutical composition Substances 0.000 claims description 22
230000003938 response to stress Effects 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 17
208000015122 neurodegenerative disease Diseases 0.000 claims description 17
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
230000004770 neurodegeneration Effects 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 14
125000003368 amide group Chemical group 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
230000001684 chronic effect Effects 0.000 claims description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
208000030090 Acute Disease Diseases 0.000 claims description 9
208000017667 Chronic Disease Diseases 0.000 claims description 9
230000001613 neoplastic effect Effects 0.000 claims description 9
201000006347 Intellectual Disability Diseases 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
208000036546 leukodystrophy Diseases 0.000 claims description 6
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
208000011580 syndromic disease Diseases 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
150000001602 bicycloalkyls Chemical group 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
210000003734 kidney Anatomy 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
206010016654 Fibrosis Diseases 0.000 claims description 3
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206010003119 arrhythmia Diseases 0.000 claims description 3
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230000000975 bioactive effect Effects 0.000 claims description 3
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208000027866 inflammatory disease Diseases 0.000 claims description 3
210000004185 liver Anatomy 0.000 claims description 3
210000004072 lung Anatomy 0.000 claims description 3
208000030159 metabolic disease Diseases 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
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125000001624 naphthyl group Chemical group 0.000 claims description 3
208000004296 neuralgia Diseases 0.000 claims description 3
208000021722 neuropathic pain Diseases 0.000 claims description 3
210000000056 organ Anatomy 0.000 claims description 3
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 3
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 3
125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
208000020431 spinal cord injury Diseases 0.000 claims description 3
VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 2
208000035473 Communicable disease Diseases 0.000 claims description 2
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 2
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
208000019423 liver disease Diseases 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
239000000243 solution Substances 0.000 description 120
239000000543 intermediate Substances 0.000 description 115
238000005160 1H NMR spectroscopy Methods 0.000 description 91
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235000019439 ethyl acetate Nutrition 0.000 description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
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IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 35
239000007832 Na2SO4 Substances 0.000 description 34
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
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