CA2629402A1 - Modulateurs de beta-secretase et procedes d'utilisation associes - Google Patents
Modulateurs de beta-secretase et procedes d'utilisation associes Download PDFInfo
- Publication number
- CA2629402A1 CA2629402A1 CA002629402A CA2629402A CA2629402A1 CA 2629402 A1 CA2629402 A1 CA 2629402A1 CA 002629402 A CA002629402 A CA 002629402A CA 2629402 A CA2629402 A CA 2629402A CA 2629402 A1 CA2629402 A1 CA 2629402A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- acetamide
- methyl
- dihydrospiro
- pyridin
- Prior art date
- 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.)
- Granted
Links
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 title claims abstract 5
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 33
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 732
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 270
- -1 C2-10-alkynyl Chemical group 0.000 claims 164
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 146
- 125000005842 heteroatom Chemical group 0.000 claims 78
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 57
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 55
- 125000004122 cyclic group Chemical group 0.000 claims 50
- 229910020008 S(O) Inorganic materials 0.000 claims 48
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 46
- 125000001188 haloalkyl group Chemical group 0.000 claims 45
- 125000001424 substituent group Chemical group 0.000 claims 44
- 125000002950 monocyclic group Chemical group 0.000 claims 40
- 229910052760 oxygen Inorganic materials 0.000 claims 39
- 125000002619 bicyclic group Chemical group 0.000 claims 37
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 34
- 125000004432 carbon atom Chemical group C* 0.000 claims 31
- 125000005843 halogen group Chemical group 0.000 claims 30
- 125000004043 oxo group Chemical group O=* 0.000 claims 29
- 108091008648 NR7C Proteins 0.000 claims 28
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 27
- 229910052757 nitrogen Inorganic materials 0.000 claims 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 25
- 229920006395 saturated elastomer Polymers 0.000 claims 25
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 24
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 17
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 17
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 16
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 16
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 claims 15
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 206010012289 Dementia Diseases 0.000 claims 8
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims 8
- 125000003971 isoxazolinyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 8
- 125000005968 oxazolinyl group Chemical group 0.000 claims 8
- 125000002971 oxazolyl group Chemical group 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 8
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 8
- 125000002769 thiazolinyl group Chemical group 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000004306 triazinyl group Chemical group 0.000 claims 8
- 125000001425 triazolyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 6
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 125000001041 indolyl group Chemical group 0.000 claims 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 3
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- 150000003852 triazoles Chemical class 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 101100160255 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YLR154C-H gene Proteins 0.000 claims 2
- 206010048327 Supranuclear palsy Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 2
- 206010002022 amyloidosis Diseases 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000001054 cortical effect Effects 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 230000003412 degenerative effect Effects 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 210000004558 lewy body Anatomy 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- KIFUPYQGMFVLPJ-UGIQSDBZSA-N (3s)-n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]-1-cyclobutyl-5-oxopyrrolidine-3-carboxamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(C=CC=2)C#N)NC(=O)[C@H]2CC(=O)N(C3CCC3)C2)C2)=CC(CC)=CC=C1OC12CCC1 KIFUPYQGMFVLPJ-UGIQSDBZSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- VQGHMDXJFVFTGK-XZLNYOFQSA-N (e)-3-(4-bromofuran-2-yl)-n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]prop-2-enamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)\C=C\C=2OC=C(Br)C=2)C2)=CC(CC)=CC=C1OC12CCC1 VQGHMDXJFVFTGK-XZLNYOFQSA-N 0.000 claims 1
- ZUTJTMUOWJGQBF-HZFUHODCSA-N 2-(1,3-benzothiazol-2-yloxy)-n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2SC3=CC=CC=C3N=2)C2)=CC(CC)=CC=C1OC12CCC1 ZUTJTMUOWJGQBF-HZFUHODCSA-N 0.000 claims 1
- JRDCYXKZYKGTNK-YTCPBCGMSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound CC1=NOC(C)=C1CC(=O)N[C@H]([C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)CC1=CC=CC=C1 JRDCYXKZYKGTNK-YTCPBCGMSA-N 0.000 claims 1
- YGYAGJFOMUUTBI-YTCPBCGMSA-N 2-(3-chloro-2-methylphenyl)sulfanyl-n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)CSC=2C(=C(Cl)C=CC=2)C)C2)=CC(CC)=CC=C1OC12CCC1 YGYAGJFOMUUTBI-YTCPBCGMSA-N 0.000 claims 1
- XDASZKNLEKIPAS-XQTSOSNCSA-N 3-(benzimidazol-1-yl)-n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C(C)CN2C3=CC=CC=C3N=C2)C2)=CC(CC)=CC=C1OC12CCC1 XDASZKNLEKIPAS-XQTSOSNCSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- NOEBJLGZGKXWLU-DSITVLBTSA-N n-[(2r,3s)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-[3-fluoro-4-(trifluoromethyl)phenyl]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@@H](NC(=O)C)[C@@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC=C(C(F)(F)F)C(F)=C1 NOEBJLGZGKXWLU-DSITVLBTSA-N 0.000 claims 1
- FOQIMCMQAHVRSZ-CCIHKAHMSA-N n-[(2s,3r)-1-(1-acetylpiperidin-3-yl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC2CN(CCC2)C(C)=O)NC(C)=O)C2)=CC(CC)=CC=C1OC12CCC1 FOQIMCMQAHVRSZ-CCIHKAHMSA-N 0.000 claims 1
- FOOVOKYFKXNBED-KKUQBAQOSA-N n-[(2s,3r)-1-(1-benzofuran-2-yl)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@@H](C1=CC(CC(C)(C)C)=CN=C1O1)NC[C@@H](O)[C@H](CC=2OC3=CC=CC=C3C=2)NC(=O)C)C21CCC2 FOOVOKYFKXNBED-KKUQBAQOSA-N 0.000 claims 1
- CDDAJJUYPLMFFO-CCDWMCETSA-N n-[(2s,3r)-1-(2,6-difluorophenyl)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=C(F)C=CC=C1F CDDAJJUYPLMFFO-CCDWMCETSA-N 0.000 claims 1
- BNXIACZNQPTSSD-KMDXXIMOSA-N n-[(2s,3r)-1-(2-chloro-6-methylpyridin-4-yl)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC(C)=NC(Cl)=C1 BNXIACZNQPTSSD-KMDXXIMOSA-N 0.000 claims 1
- UAMUISNPBXPDJP-CCDWMCETSA-N n-[(2s,3r)-1-(2-chlorophenyl)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1Cl UAMUISNPBXPDJP-CCDWMCETSA-N 0.000 claims 1
- RZVBZFXUKAEOIB-JIMJEQGWSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[(1r)-7-(2,2-dimethylpropyl)-3,3-dimethyl-4-oxo-1,2-dihydronaphthalen-1-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@H]1C2=CC(CC(C)(C)C)=CC=C2C(=O)C(C)(C)C1)C1=CC(F)=CC(F)=C1 RZVBZFXUKAEOIB-JIMJEQGWSA-N 0.000 claims 1
- DMSRCGAVUVUKMW-FQJHJXCSSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[(2r,4r)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,3'-oxolane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@H]1C2=CC(CC(C)(C)C)=CN=C2O[C@]2(COCC2)C1)C1=CC(F)=CC(F)=C1 DMSRCGAVUVUKMW-FQJHJXCSSA-N 0.000 claims 1
- DMSRCGAVUVUKMW-CDILPITASA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[(2r,4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,3'-oxolane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2O[C@]2(COCC2)C1)C1=CC(F)=CC(F)=C1 DMSRCGAVUVUKMW-CDILPITASA-N 0.000 claims 1
- UDTZUCALHYIIIT-HPUZDQILSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[(2s,4s)-6-ethylspiro[3,4-dihydrochromene-2,3'-oxolane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)C2)=CC(CC)=CC=C1O[C@@]12CCOC1 UDTZUCALHYIIIT-HPUZDQILSA-N 0.000 claims 1
- OMAIZYGPTREULJ-GMQQYTKMSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[(4s)-6-(2,2-dimethylpropyl)-8-propan-2-yloxyspiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@@H](C=1C=C(CC(C)(C)C)N=C(C=1O1)OC(C)C)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)C21CCC2 OMAIZYGPTREULJ-GMQQYTKMSA-N 0.000 claims 1
- NOZZVOJNQTZIPP-RJGXRXQPSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)C2)=CC(CC)=CN=C1OC12CCC1 NOZZVOJNQTZIPP-RJGXRXQPSA-N 0.000 claims 1
- BQLRKQYKBHSHRU-CCDWMCETSA-N n-[(2s,3r)-1-(3-bromo-4-fluorophenyl)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC=C(F)C(Br)=C1 BQLRKQYKBHSHRU-CCDWMCETSA-N 0.000 claims 1
- KAPLIPXREPVYPH-KMDXXIMOSA-N n-[(2s,3r)-1-(3-chloro-5-fluorophenyl)-3-hydroxy-4-[[(4s)-6-(2-hydroxy-2-methylpropyl)spiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]butan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)O)=NC=C2OC2(CCC2)C1)C1=CC(F)=CC(Cl)=C1 KAPLIPXREPVYPH-KMDXXIMOSA-N 0.000 claims 1
- ZNHPLLVKRFJFLT-RBZQAINGSA-N n-[(2s,3r)-1-(3-cyanophenyl)-3-hydroxy-4-[[(1r)-7-methoxy-3,3-dimethyl-4-oxo-1,2-dihydronaphthalen-1-yl]amino]butan-2-yl]-2-methoxyacetamide Chemical compound C([C@H](NC(=O)COC)[C@H](O)CN[C@H]1C2=CC(OC)=CC=C2C(=O)C(C)(C)C1)C1=CC=CC(C#N)=C1 ZNHPLLVKRFJFLT-RBZQAINGSA-N 0.000 claims 1
- NMJUOWGWEULNHY-RBZQAINGSA-N n-[(2s,3r)-1-(3-cyanophenyl)-3-hydroxy-4-[[(1r)-7-methoxy-3,3-dimethyl-4-oxo-1,2-dihydronaphthalen-1-yl]amino]butan-2-yl]acetamide Chemical compound C([C@@H]([C@H](O)CN[C@@H]1CC(C)(C)C(=O)C2=CC=C(C=C21)OC)NC(C)=O)C1=CC=CC(C#N)=C1 NMJUOWGWEULNHY-RBZQAINGSA-N 0.000 claims 1
- WUSBKIIPHRACDX-KKUQBAQOSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC=CC(C#N)=C1 WUSBKIIPHRACDX-KKUQBAQOSA-N 0.000 claims 1
- GSSLCFLHVNRVIG-KKUQBAQOSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]-2-(2-oxo-1,3-oxazolidin-3-yl)acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(C=CC=2)C#N)NC(=O)CN2C(OCC2)=O)C2)=CC(CC)=CC=C1OC12CCC1 GSSLCFLHVNRVIG-KKUQBAQOSA-N 0.000 claims 1
- BDUKFURARPTELL-CCDWMCETSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]-2-methoxyacetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(C=CC=2)C#N)NC(=O)COC)C2)=CC(CC)=CC=C1OC12CCC1 BDUKFURARPTELL-CCDWMCETSA-N 0.000 claims 1
- DRNVFBXXOGITRL-OIFRRMEBSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]-2-phenoxyacetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(C=CC=2)C#N)NC(=O)COC=2C=CC=CC=2)C2)=CC(CC)=CC=C1OC12CCC1 DRNVFBXXOGITRL-OIFRRMEBSA-N 0.000 claims 1
- XYLJFRJPLIJCKC-CCDWMCETSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(C=CC=2)C#N)NC(C)=O)C2)=CC(CC)=CC=C1OC12CCC1 XYLJFRJPLIJCKC-CCDWMCETSA-N 0.000 claims 1
- CZOPXKQMSNLYKH-CCDWMCETSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]propanamide Chemical compound C([C@H](NC(=O)CC)[C@H](O)CN[C@@H]1C2=CC(CC)=CC=C2OC2(CCC2)C1)C1=CC=CC(C#N)=C1 CZOPXKQMSNLYKH-CCDWMCETSA-N 0.000 claims 1
- IAPFLLDNGSEQJC-KMDXXIMOSA-N n-[(2s,3r)-1-(3-cyanophenyl)-4-[[(4s)-6-ethylspiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]-2-methoxyacetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(C=CC=2)C#N)NC(=O)COC)C2)=CC(CC)=CN=C1OC12CCC1 IAPFLLDNGSEQJC-KMDXXIMOSA-N 0.000 claims 1
- OAXMWLBSWJPLPK-GGFLZPDSSA-N n-[(2s,3r)-1-(3-fluorophenyl)-3-hydroxy-4-[[(4s)-6-[(2s)-3,3,3-trifluoro-2-methylpropyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]butan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(F)C=CC=2)NC(C)=O)C2)=CC(C[C@H](C)C(F)(F)F)=CN=C1OC12CCC1 OAXMWLBSWJPLPK-GGFLZPDSSA-N 0.000 claims 1
- ZPZXFRAHZVMTJS-FQJHJXCSSA-N n-[(2s,3r)-1-(4-chlorophenyl)-4-[[(2r,4r)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,3'-oxolane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@H]1C2=CC(CC(C)(C)C)=CN=C2O[C@]2(COCC2)C1)C1=CC=C(Cl)C=C1 ZPZXFRAHZVMTJS-FQJHJXCSSA-N 0.000 claims 1
- ZPZXFRAHZVMTJS-CDILPITASA-N n-[(2s,3r)-1-(4-chlorophenyl)-4-[[(2r,4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,3'-oxolane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2O[C@]2(COCC2)C1)C1=CC=C(Cl)C=C1 ZPZXFRAHZVMTJS-CDILPITASA-N 0.000 claims 1
- WFLXNGWTEYYRAX-KKUQBAQOSA-N n-[(2s,3r)-1-(4-chlorophenyl)-4-[[(4s)-6-(2,2-dimethylbut-3-ynyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C#C)=CN=C2OC2(CCC2)C1)C1=CC=C(Cl)C=C1 WFLXNGWTEYYRAX-KKUQBAQOSA-N 0.000 claims 1
- DYVCXXGYOURUSA-KKUQBAQOSA-N n-[(2s,3r)-1-(4-chlorophenyl)-4-[[(4s)-6-(2,2-dimethylbutyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC(Cl)=CC=2)NC(C)=O)C2)=CC(CC(C)(C)CC)=CN=C1OC12CCC1 DYVCXXGYOURUSA-KKUQBAQOSA-N 0.000 claims 1
- ODDWWSJGPLLKFI-CXSMSNRLSA-N n-[(2s,3r)-1-(4-chlorophenyl)-4-[[(4s)-6-[(1s)-1-fluoro-2,2-dimethylpropyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(=CN=C2OC2(CCC2)C1)[C@@H](F)C(C)(C)C)C1=CC=C(Cl)C=C1 ODDWWSJGPLLKFI-CXSMSNRLSA-N 0.000 claims 1
- DAKKPMHNILAGSU-CCDWMCETSA-N n-[(2s,3r)-1-(4-fluoro-3-methylphenyl)-4-[[(4s)-6-(2-fluoro-2-methylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)F)=CN=C2OC2(CCC2)C1)C1=CC=C(F)C(C)=C1 DAKKPMHNILAGSU-CCDWMCETSA-N 0.000 claims 1
- AMBXNGPAQJZTIH-CCDWMCETSA-N n-[(2s,3r)-1-(4-fluorophenyl)-3-hydroxy-4-[[(4s)-6-(2-methylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]butan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(C)=O)C2)=CC(CC(C)C)=CN=C1OC12CCC1 AMBXNGPAQJZTIH-CCDWMCETSA-N 0.000 claims 1
- IGPZIUUUAOWIIW-KMDXXIMOSA-N n-[(2s,3r)-1-(4-fluorophenyl)-3-hydroxy-4-[[(4s)-6-propylspiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]butan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(C)=O)C2)=CC(CCC)=CN=C1OC12CCC1 IGPZIUUUAOWIIW-KMDXXIMOSA-N 0.000 claims 1
- UTERZPGUGZHCAR-PCCBWWKXSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[(4s)-2,6,6-trimethyl-5,7-dihydro-4h-1-benzofuran-4-yl]amino]butan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C=2C=C(C)OC=2CC(C)(C)C1)C1=CC=CC=C1 UTERZPGUGZHCAR-PCCBWWKXSA-N 0.000 claims 1
- DWYZIQWQHNIECY-ISJGIBHGSA-N n-[(2s,3r)-3-hydroxy-4-[[(1r)-7-(2-methoxyethylamino)-3,3-dimethyl-4-oxo-1,2-dihydronaphthalen-1-yl]amino]-1-phenylbutan-2-yl]acetamide Chemical compound C([C@@H]([C@H](O)CN[C@@H]1CC(C)(C)C(=O)C2=CC=C(C=C21)NCCOC)NC(C)=O)C1=CC=CC=C1 DWYZIQWQHNIECY-ISJGIBHGSA-N 0.000 claims 1
- GMHCBOGSXGMCIF-KKUQBAQOSA-N n-[(2s,3r)-3-hydroxy-4-[[(4s)-6-(3-methylbutyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-phenylbutan-2-yl]-2-methoxyacetamide Chemical compound C([C@H](NC(=O)COC)[C@H](O)CN[C@@H]1C2=CC(CCC(C)C)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1 GMHCBOGSXGMCIF-KKUQBAQOSA-N 0.000 claims 1
- OYXTXWNYHMNFEP-SSUZURRFSA-N n-[(2s,3r)-3-hydroxy-4-[[(4s)-6-[(2s)-oxolan-2-yl]spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(=CC=C2OC2(CCC2)C1)[C@H]1OCCC1)C1=CC=CC=C1 OYXTXWNYHMNFEP-SSUZURRFSA-N 0.000 claims 1
- UUQAXOVTDUHVNH-WDTRASESSA-N n-[(2s,3r)-3-hydroxy-4-[[(4s)-6-[[(2r)-2-methyloxolan-2-yl]methyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(C[C@]3(C)OCCC3)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1 UUQAXOVTDUHVNH-WDTRASESSA-N 0.000 claims 1
- YNHWCLFEEDJTNJ-GYUKIKGESA-N n-[(2s,3r)-3-hydroxy-4-[[(4s)-6-[[(2r)-oxolan-2-yl]methyl]spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(C[C@@H]3OCCC3)=CC=C2OC2(CCC2)C1)C1=CC=CC=C1 YNHWCLFEEDJTNJ-GYUKIKGESA-N 0.000 claims 1
- AFNUOMRXRGRYLK-HMNRDNJPSA-N n-[(2s,3r)-3-hydroxy-4-[[(4s)-6-[[(2r)-oxolan-2-yl]methyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(C[C@@H]3OCCC3)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1 AFNUOMRXRGRYLK-HMNRDNJPSA-N 0.000 claims 1
- KGBBCOHRANKVDH-ZCLKUGBOSA-N n-[(2s,3r)-3-hydroxy-4-[[(4s)-6-[[(2s)-oxolan-2-yl]methyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-phenylbutan-2-yl]-2-methoxyacetamide Chemical compound C([C@H](NC(=O)COC)[C@H](O)CN[C@@H]1C2=CC(C[C@H]3OCCC3)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1 KGBBCOHRANKVDH-ZCLKUGBOSA-N 0.000 claims 1
- ZDOVUIOQKZPCLW-GMQQYTKMSA-N n-[(2s,3r)-4-[[(1s)-7-(cyclopentylamino)-3,3-dimethyl-4-oxo-1,2-dihydronaphthalen-1-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(NC3CCCC3)=CC=C2C(=O)C(C)(C)C1)C1=CC=CC=C1 ZDOVUIOQKZPCLW-GMQQYTKMSA-N 0.000 claims 1
- YXXSUWYLMCDEAZ-XWZVPRMZSA-N n-[(2s,3r)-4-[[(2r,4s)-6-chloro-8-morpholin-4-ylspiro[3,4-dihydrochromene-2,3'-oxolane]-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=C(C(=CC(Cl)=C2)N2CCOCC2)O[C@]2(COCC2)C1)C1=CC(F)=CC(F)=C1 YXXSUWYLMCDEAZ-XWZVPRMZSA-N 0.000 claims 1
- BIHRVTGDRMCRBV-QXUYBEEESA-N n-[(2s,3r)-4-[[(2r,4s)-6-chlorospiro[3,4-dihydropyrano[2,3-b]pyridine-2,3'-oxolane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(Cl)=CN=C2O[C@]2(COCC2)C1)C1=CC=CC=C1 BIHRVTGDRMCRBV-QXUYBEEESA-N 0.000 claims 1
- LTKKNMVAMBUECM-NAVOWQOKSA-N n-[(2s,3r)-4-[[(2s,4s)-1'-acetyl-6-ethylspiro[3,4-dihydrochromene-2,3'-pyrrolidine]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(C)=O)C2)=CC(CC)=CC=C1O[C@]12CCN(C(C)=O)C1 LTKKNMVAMBUECM-NAVOWQOKSA-N 0.000 claims 1
- OAPVYUJRXSHJFV-RGYUWNBKSA-N n-[(2s,3r)-4-[[(2s,4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,3'-oxolane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-methoxyacetamide Chemical compound C([C@H](NC(=O)COC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2O[C@@]2(COCC2)C1)C1=CC=CC=C1 OAPVYUJRXSHJFV-RGYUWNBKSA-N 0.000 claims 1
- RPLRVPIJGAVSFX-KEZQHZCBSA-N n-[(2s,3r)-4-[[(2s,4s)-6-bromo-2-methyl-2-(trifluoromethyl)-3,4-dihydrochromen-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(Br)=CC=C2O[C@@](C)(C1)C(F)(F)F)C1=CC=CC=C1 RPLRVPIJGAVSFX-KEZQHZCBSA-N 0.000 claims 1
- CLMFBRCNMBGVJX-OYUWMTPXSA-N n-[(2s,3r)-4-[[(4r)-6-(2,2-dimethylpropyl)-8-propan-2-yloxyspiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](C=1C=C(CC(C)(C)C)N=C(C=1O1)OC(C)C)NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(C)=O)C21CCC2 CLMFBRCNMBGVJX-OYUWMTPXSA-N 0.000 claims 1
- WEFKDLDYYSHQRC-JBRSBNLGSA-N n-[(2s,3r)-4-[[(4r)-8-(dimethylamino)-6-ethyl-2,2-dimethyl-3,4-dihydrochromen-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@@H]([C@H](O)CN[C@H]1C=2C=C(C=C(C=2OC(C)(C)C1)N(C)C)CC)NC(C)=O)C1=CC=CC=C1 WEFKDLDYYSHQRC-JBRSBNLGSA-N 0.000 claims 1
- RJEWKGNHSJODHQ-WPFOTENUSA-N n-[(2s,3r)-4-[[(4s)-1-acetyl-6-bromo-2,2-dimethyl-3,4-dihydroquinolin-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(Br)=CC=C2N(C(C)=O)C(C)(C)C1)C1=CC=CC=C1 RJEWKGNHSJODHQ-WPFOTENUSA-N 0.000 claims 1
- OUCWEAFTVAXJCV-KMDXXIMOSA-N n-[(2s,3r)-4-[[(4s)-2-ethyl-6,6-dimethyl-5,7-dihydro-4h-1-benzothiophen-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(2-oxopyrrolidin-1-yl)acetamide Chemical compound C([C@@H]([C@H](O)CN[C@@H]1C=2C=C(SC=2CC(C)(C)C1)CC)NC(=O)CN1C(CCC1)=O)C1=CC=CC=C1 OUCWEAFTVAXJCV-KMDXXIMOSA-N 0.000 claims 1
- ZQWWGBZQRZMGBQ-KKUQBAQOSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-2,2-dimethyl-3,4-dihydro-1h-quinolin-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CC=C2NC(C)(C)C1)C1=CC=CC=C1 ZQWWGBZQRZMGBQ-KKUQBAQOSA-N 0.000 claims 1
- XYYAANNCGMZRRC-KMDXXIMOSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-2,2-dimethyl-3,4-dihydropyrano[2,3-b]pyridin-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC(C)(C)C1)C1=CC=C(F)C=C1 XYYAANNCGMZRRC-KMDXXIMOSA-N 0.000 claims 1
- JJKXIZRLMNHXMH-KMDXXIMOSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-2,2-dimethyl-3,4-dihydropyrano[2,3-c]pyridin-4-yl]amino]-1-(3-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=NC=C2OC(C)(C)C1)C1=CC=CC(F)=C1 JJKXIZRLMNHXMH-KMDXXIMOSA-N 0.000 claims 1
- HPDATYCGMJPNRR-CCDWMCETSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-8-methoxyspiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(3-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@@H](C=1C=C(CC(C)(C)C)N=C(C=1O1)OC)NC[C@@H](O)[C@H](CC=2C=C(F)C=CC=2)NC(C)=O)C21CCC2 HPDATYCGMJPNRR-CCDWMCETSA-N 0.000 claims 1
- CRMCZCFMTGEBJC-HZFUHODCSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-8-morpholin-4-ylspiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=C(C(=NC(CC(C)(C)C)=C2)N2CCOCC2)OC2(CCC2)C1)C1=CC=CC=C1 CRMCZCFMTGEBJC-HZFUHODCSA-N 0.000 claims 1
- ZTDPMDMKRAIUPD-GMQQYTKMSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-8-propan-2-yloxyspiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(3-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@@H](C=1C=C(CC(C)(C)C)N=C(C=1O1)OC(C)C)NC[C@@H](O)[C@H](CC=2C=C(F)C=CC=2)NC(C)=O)C21CCC2 ZTDPMDMKRAIUPD-GMQQYTKMSA-N 0.000 claims 1
- CLMFBRCNMBGVJX-GMQQYTKMSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)-8-propan-2-yloxyspiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@@H](C=1C=C(CC(C)(C)C)N=C(C=1O1)OC(C)C)NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(C)=O)C21CCC2 CLMFBRCNMBGVJX-GMQQYTKMSA-N 0.000 claims 1
- ZAJKCLUZHUAIIX-CCDWMCETSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(2-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1F ZAJKCLUZHUAIIX-CCDWMCETSA-N 0.000 claims 1
- FGETYKYHLUCWPV-RJGXRXQPSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]-2,2-difluoroacetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(=O)C(F)F)C2)=CC(CC(C)(C)C)=CN=C1OC12CCC1 FGETYKYHLUCWPV-RJGXRXQPSA-N 0.000 claims 1
- FYUUNYNZWADHLV-CCDWMCETSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(trifluoromethyl)phenyl]butan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C1=CC=CC(C(F)(F)F)=C1 FYUUNYNZWADHLV-CCDWMCETSA-N 0.000 claims 1
- FKUSUFVBJLHBPS-HZFUHODCSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(5-methylpyrazol-1-yl)acetamide Chemical compound CC1=CC=NN1CC(=O)N[C@H]([C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)CC1=CC=CC=C1 FKUSUFVBJLHBPS-HZFUHODCSA-N 0.000 claims 1
- CMQTXZOXZRICDX-CCDWMCETSA-N n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=NC=C2OC2(CCC2)C1)C1=CC=CC=C1 CMQTXZOXZRICDX-CCDWMCETSA-N 0.000 claims 1
- XEFTVFYBIIOHLH-KMDXXIMOSA-N n-[(2s,3r)-4-[[(4s)-6-(2-fluoro-2-methylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)F)=CN=C2OC2(CCC2)C1)C1=CC=CC=C1 XEFTVFYBIIOHLH-KMDXXIMOSA-N 0.000 claims 1
- RVHAZHOLYWGIHZ-CXSMSNRLSA-N n-[(2s,3r)-4-[[(4s)-6-[(1r)-1-fluoro-2-methylpropyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(C)=O)C2)=CC([C@H](F)C(C)C)=CN=C1OC12CCC1 RVHAZHOLYWGIHZ-CXSMSNRLSA-N 0.000 claims 1
- NSFNRHDXSOQIKI-CXSMSNRLSA-N n-[(2s,3r)-4-[[(4s)-6-[(1s)-1-fluoro-2,2-dimethylpropyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(=CN=C2OC2(CCC2)C1)[C@@H](F)C(C)(C)C)C1=CC=C(F)C=C1 NSFNRHDXSOQIKI-CXSMSNRLSA-N 0.000 claims 1
- HCSAUHXMCQXWJH-XLRUWRGTSA-N n-[(2s,3r)-4-[[(4s)-6-[(2r)-3-fluoro-2-methylpropyl]spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC(F)=CC=2)NC(C)=O)C2)=CC(C[C@H](CF)C)=CN=C1OC12CCC1 HCSAUHXMCQXWJH-XLRUWRGTSA-N 0.000 claims 1
- BNKKNNRDNAMWKW-FDFHNCONSA-N n-[(2s,3r)-4-[[(4s)-6-bromo-2,2-dimethyl-3,4-dihydro-1h-quinolin-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(Br)=CC=C2NC(C)(C)C1)C1=CC=CC=C1 BNKKNNRDNAMWKW-FDFHNCONSA-N 0.000 claims 1
- UYIYYVXNBPPUFP-FDFHNCONSA-N n-[(2s,3r)-4-[[(4s)-6-bromospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(Br)=CC=C2OC2(CCC2)C1)C1=CC(F)=CC(F)=C1 UYIYYVXNBPPUFP-FDFHNCONSA-N 0.000 claims 1
- YDIVXCZMBDZKOK-PCCBWWKXSA-N n-[(2s,3r)-4-[[(4s)-6-bromospiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(Br)=CN=C2OC2(CCC2)C1)C1=CC=C(F)C=C1 YDIVXCZMBDZKOK-PCCBWWKXSA-N 0.000 claims 1
- PUWMOTSQDRSSHT-OHSXHVKISA-N n-[(2s,3r)-4-[[(4s)-6-chloro-8-morpholin-4-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-1-(3-cyanophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=C(C(=CC(Cl)=C2)N2CCOCC2)OC2(CCC2)C1)C1=CC=CC(C#N)=C1 PUWMOTSQDRSSHT-OHSXHVKISA-N 0.000 claims 1
- XCDLZZNRQMUGRN-OHSXHVKISA-N n-[(2s,3r)-4-[[(4s)-6-ethyl-2,2-dimethyl-8-pyrrolidin-1-yl-3,4-dihydrochromen-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide Chemical compound C([C@@H](C=1C=C(C=2)CC)NC[C@@H](O)[C@H](CC=3C=CC=CC=3)NC(C)=O)C(C)(C)OC=1C=2N1CCCC1 XCDLZZNRQMUGRN-OHSXHVKISA-N 0.000 claims 1
- KNUQXNGMAGESQG-RWSKJCERSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-(3-prop-2-enylphenyl)butan-2-yl]hept-6-enamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=C(CC=C)C=CC=2)NC(=O)CCCCC=C)C2)=CC(CC)=CC=C1OC12CCC1 KNUQXNGMAGESQG-RWSKJCERSA-N 0.000 claims 1
- FZRDGNVMKBNQIT-CCDWMCETSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(2-oxo-1,3-oxazolidin-3-yl)acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)CN2C(OCC2)=O)C2)=CC(CC)=CC=C1OC12CCC1 FZRDGNVMKBNQIT-CCDWMCETSA-N 0.000 claims 1
- BZDINFCSPPULSF-OIFRRMEBSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(3-oxo-1h-isoindol-2-yl)acetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)CN2C(C3=CC=CC=C3C2)=O)C2)=CC(CC)=CC=C1OC12CCC1 BZDINFCSPPULSF-OIFRRMEBSA-N 0.000 claims 1
- WOWRZGXTDDGJCI-HZFUHODCSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(4-propyltriazol-1-yl)acetamide Chemical compound N1=NC(CCC)=CN1CC(=O)N[C@H]([C@H](O)CN[C@@H]1C2=CC(CC)=CC=C2OC2(CCC2)C1)CC1=CC=CC=C1 WOWRZGXTDDGJCI-HZFUHODCSA-N 0.000 claims 1
- YHACHHURHPYYGI-OIFRRMEBSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-phthalazin-1-ylsulfanylacetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)CSC=2C3=CC=CC=C3C=NN=2)C2)=CC(CC)=CC=C1OC12CCC1 YHACHHURHPYYGI-OIFRRMEBSA-N 0.000 claims 1
- IMIVZZHWYHXNBD-YTCPBCGMSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-pyrrolo[2,3-b]pyridin-1-ylacetamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)CN2C3=NC=CC=C3C=C2)C2)=CC(CC)=CC=C1OC12CCC1 IMIVZZHWYHXNBD-YTCPBCGMSA-N 0.000 claims 1
- IWLFPJWTXSHWFV-SSNGLDLMSA-N n-[(2s,3r)-4-[[(4s)-6-ethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]-2-thiophen-2-ylsulfanylpropanamide Chemical compound C1([C@@H](NC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C(C)SC=2SC=CC=2)C2)=CC(CC)=CC=C1OC12CCC1 IWLFPJWTXSHWFV-SSNGLDLMSA-N 0.000 claims 1
- NOXDMGCXAAVHAI-HZFUHODCSA-N n-[(2s,3r)-4-[[(4s)-8-(dimethylamino)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-[4-(dimethylamino)phenyl]-3-hydroxybutan-2-yl]acetamide Chemical compound C1=CC(N(C)C)=CC=C1C[C@H](NC(C)=O)[C@H](O)CN[C@@H]1C(C=C(CC(C)(C)C)N=C2N(C)C)=C2OC2(CCC2)C1 NOXDMGCXAAVHAI-HZFUHODCSA-N 0.000 claims 1
- FCTGWYSVAGSHCI-KMDXXIMOSA-N n-[(2s,3r)-4-[[(4s)-8-chloro-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(3-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=NC(Cl)=C2OC2(CCC2)C1)C1=CC=CC(F)=C1 FCTGWYSVAGSHCI-KMDXXIMOSA-N 0.000 claims 1
- RDNVORBKZVZOMD-KMDXXIMOSA-N n-[(2s,3r)-4-[[(4s)-8-chloro-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-c]pyridine-2,1'-cyclobutane]-4-yl]amino]-1-(4-fluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=NC(Cl)=C2OC2(CCC2)C1)C1=CC=C(F)C=C1 RDNVORBKZVZOMD-KMDXXIMOSA-N 0.000 claims 1
- HQOAUESNWDRKPT-KMDXXIMOSA-N n-[(4s)-4-[[(2r,3s)-3-acetamido-4-(3,5-difluorophenyl)-2-hydroxybutyl]amino]spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@H]1C2=CC(NC(C)=O)=CC=C2OC2(CCC2)C1)C1=CC(F)=CC(F)=C1 HQOAUESNWDRKPT-KMDXXIMOSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- KNEPBZMJMJUNQX-UHFFFAOYSA-N pent-4-ynamide Chemical compound NC(=O)CCC#C KNEPBZMJMJUNQX-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73910805P | 2005-11-21 | 2005-11-21 | |
| US60/739,108 | 2005-11-21 | ||
| US85482406P | 2006-10-27 | 2006-10-27 | |
| US60/854,824 | 2006-10-27 | ||
| PCT/US2006/044058 WO2007061670A1 (fr) | 2005-11-21 | 2006-11-13 | Modulateurs de beta-secretase et procedes d'utilisation associes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2629402A1 true CA2629402A1 (fr) | 2007-05-31 |
| CA2629402C CA2629402C (fr) | 2011-07-26 |
Family
ID=39708735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2629402A Expired - Fee Related CA2629402C (fr) | 2005-11-21 | 2006-11-13 | Modulateurs de beta-secretase et procedes d'utilisation associes |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1971598A1 (fr) |
| JP (1) | JP5274258B2 (fr) |
| AR (1) | AR057985A1 (fr) |
| AU (1) | AU2006316620B2 (fr) |
| CA (1) | CA2629402C (fr) |
| PE (1) | PE20070645A1 (fr) |
| TW (1) | TW200800966A (fr) |
| WO (1) | WO2007061670A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7763609B2 (en) | 2003-12-15 | 2010-07-27 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| MX2009012608A (es) * | 2007-05-25 | 2009-12-07 | Amgen Inc | Compuestos de hidroxietil amina substituidos como moduladores de beta-secretasa y metodos de uso. |
| TW200901991A (en) * | 2007-05-25 | 2009-01-16 | Amgen Inc | Substituted hydroxyethyl amine compounds as beta-secretase modulators and methods of use |
| CN103687839B (zh) | 2011-07-21 | 2016-06-08 | 通用电气健康护理有限公司 | 前体化合物及其制备方法 |
| JP2015514073A (ja) * | 2012-03-20 | 2015-05-18 | エラン ファーマシューティカルズ， リミテッド・ライアビリティ・カンパニー | スピロ環式ジヒドロ−チアジンおよびジヒドロ−オキサジンｂａｃｅ阻害剤、ならびにその組成物および使用 |
| US9932333B2 (en) | 2014-07-16 | 2018-04-03 | Japan Science And Technology Agency | Benzothiazole compound and medicine containing same |
| JP7413346B2 (ja) | 2019-03-06 | 2024-01-15 | 第一三共株式会社 | ピロロピラゾール誘導体 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY138097A (en) | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
| ATE314343T1 (de) | 2000-06-30 | 2006-01-15 | Elan Pharm Inc | Verbindungen zur behandlung der alzheimerischen krankheit |
| US7196163B2 (en) | 2001-05-22 | 2007-03-27 | Merk & Co., Inc. | Assays using amyloid precursor proteins with modified β-secretase cleavage sites to monitor β-secretase activity |
| MXPA04000140A (es) | 2001-06-27 | 2004-06-03 | Elan Pharm Inc | Derivados de beta-hidroxiamina utiles en el tratamiento de enfermedad de alzheimer. |
| KR100713137B1 (ko) | 2001-06-28 | 2007-05-02 | 동화약품공업주식회사 | 신규의 2,4-디플루오로벤즈아미드 유도체 |
| MXPA04000328A (es) | 2001-07-10 | 2004-07-23 | Pharmacia & Upjohn Comapny | Derivados de alfa-hidroxiamida estatina para tratamiento de enfermedad de alzheimer. |
| MXPA04000338A (es) | 2001-07-10 | 2004-07-23 | Upjohn Co | Diamindioles para tratamiento de enfermedad de alzheimer. |
| AP2004002952A0 (en) | 2001-07-11 | 2004-03-31 | Elan Pharm Inc | N-(3-amino-2-hydroxy-propyl) substituted alkylamide compounds. |
| AU2002343483A1 (en) | 2001-10-04 | 2003-04-14 | Elan Pharmaceuticals, Inc. | Hydroxypropylamines |
| BR0213138A (pt) | 2001-10-05 | 2004-08-24 | Elan Pharm Inc | Métodos de tratar ou prevenir mal de alzheimer e uma doença distinguida por depósito de beta-amilóide no cérebro, de tratar um paciente que tenha, ou de prevenir um paciente de contrair uma doença ou condição, de produzir um complexo de beta-secretase e de inibir a produção de placa beta-amilóide em um animal, composição e uso de um composto |
| WO2003037325A1 (fr) | 2001-10-29 | 2003-05-08 | Elan Pharmaceuticals, Inc. | Amides a substitution hydroxy pour le traitement de la maladie d'alzheimer |
| AR039555A1 (es) | 2001-11-08 | 2005-02-23 | Upjohn Co | Derivados n,n'-sustituidos de 1,3-diamino-2-hidroxipropano |
| AR037460A1 (es) | 2001-11-30 | 2004-11-10 | Smithkline Beecham Plc | Compuesto de hidroxietileno, composicion farmaceutica que lo comprende, uso del mismo para la fabricacion de un medicamento y procedimiento para su preparacion |
| JP2005511735A (ja) | 2001-12-06 | 2005-04-28 | イーラン ファーマスーティカルズ、インコーポレイテッド | 置換ヒドロキシエチルアミン |
| EP1458745A2 (fr) | 2002-01-04 | 2004-09-22 | Elan Pharmaceuticals, Inc. | Amino carboxamides substitues destines au traitement de la maladie d'alzheimer |
| EP1471910A2 (fr) | 2002-01-17 | 2004-11-03 | Neurogen Corporation | Analogues de quinazoline-4-ylamine substitues comme modulateurs de receptors de la capsaicin |
| US7132568B2 (en) | 2002-06-17 | 2006-11-07 | Sunesis Pharmaceuticals, Inc. | Aspartyl protease inhibitors |
| US7115747B2 (en) | 2002-06-20 | 2006-10-03 | Pharmacia & Upjohn Company | Process for preparing oxazole intermediates |
| UY27967A1 (es) | 2002-09-10 | 2004-05-31 | Pfizer | Acetil 2-hindroxi-1,3-diaminoalcanos |
| US7362070B2 (en) | 2002-11-04 | 2008-04-22 | Hamilton Sundstrand Corporation | Electric motor control system including position determination and error correction |
| ATE443043T1 (de) | 2002-11-12 | 2009-10-15 | Merck & Co Inc | Phenylcarboxamide als beta-sekretase-hemmer zur behandlung von alzheimer |
| CA2507484A1 (fr) * | 2002-11-27 | 2004-06-17 | Elan Pharmaceuticals, Inc. | Urees et carbamates substitues |
| GB0228410D0 (en) | 2002-12-05 | 2003-01-08 | Glaxo Group Ltd | Novel Compounds |
| CA2512111A1 (fr) | 2003-01-07 | 2004-07-29 | Merck And Co., Inc. | Inhibiteurs de beta-secretase macrocyclique pour traiter la maladie d'alzheimer |
| BRPI0408295A (pt) | 2003-03-14 | 2006-03-07 | Merck Sharp & Dohme | uso de um composto |
| GB0305918D0 (en) | 2003-03-14 | 2003-04-23 | Glaxo Group Ltd | Novel compounds |
| BRPI0409627A (pt) | 2003-04-21 | 2006-04-25 | Elan Pharm Inc | 2-hidróxi-3-diaminoalcanos de fenacila |
| CL2004000849A1 (es) | 2003-04-21 | 2005-01-28 | Elan Pharmaceuticals Inc Pharm | Compuestos derivados de benzamidas-2-hidroxi-3-diaminoalcanos, utiles para el tratamiento o la prevencion de alzheimer, sindrome de down, hemorragia cerebral hereditaria, demencias degenerativas y otras. |
| GB0309221D0 (en) * | 2003-04-23 | 2003-06-04 | Glaxo Group Ltd | Novel compounds |
| WO2005005374A1 (fr) | 2003-06-16 | 2005-01-20 | Sunesis Pharmaceuticals, Inc. | Inhibiteurs d'aspartyl-protease |
| JP2007516207A (ja) | 2003-06-30 | 2007-06-21 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病の治療のためのＮ−アルキルフェニルカルボキサミドβ−セクレターゼ阻害剤 |
| CA2530006A1 (fr) | 2003-07-01 | 2005-01-20 | Merck & Co., Inc. | Inhibiteurs de la beta-secretase de phenylcarboxylate destines au traitement de la maladie d'alzheimer |
| GB0317491D0 (en) * | 2003-07-25 | 2003-08-27 | Novartis Ag | Organic compounds |
| US20060014790A1 (en) * | 2004-01-21 | 2006-01-19 | Varghese John | Methods of treatment of amyloidosis using spirocyclohexane aspartyl-protease inhibitors |
| JP2007528403A (ja) * | 2004-03-09 | 2007-10-11 | エラン ファーマシューティカルズ，インコーポレイテッド | 二環式アスパラギン酸プロテアーゼ阻害薬を用いるアミロイドーシスの処置方法 |
| MXPA06010899A (es) * | 2004-03-25 | 2006-12-15 | Elan Pharm Inc | 1,3-diaminopropanos substituidos con 2-amino y 2-tio. |
-
2006
- 2006-11-13 CA CA2629402A patent/CA2629402C/fr not_active Expired - Fee Related
- 2006-11-13 AU AU2006316620A patent/AU2006316620B2/en not_active Ceased
- 2006-11-13 EP EP06837478A patent/EP1971598A1/fr not_active Withdrawn
- 2006-11-13 WO PCT/US2006/044058 patent/WO2007061670A1/fr active Application Filing
- 2006-11-13 JP JP2008541258A patent/JP5274258B2/ja not_active Expired - Fee Related
- 2006-11-20 PE PE2006001476A patent/PE20070645A1/es not_active Application Discontinuation
- 2006-11-21 AR ARP060105083A patent/AR057985A1/es unknown
- 2006-11-21 TW TW095143035A patent/TW200800966A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006316620B2 (en) | 2011-03-03 |
| EP1971598A1 (fr) | 2008-09-24 |
| WO2007061670A1 (fr) | 2007-05-31 |
| JP2009516684A (ja) | 2009-04-23 |
| JP5274258B2 (ja) | 2013-08-28 |
| AU2006316620A1 (en) | 2007-05-31 |
| TW200800966A (en) | 2008-01-01 |
| PE20070645A1 (es) | 2007-08-24 |
| CA2629402C (fr) | 2011-07-26 |
| AR057985A1 (es) | 2008-01-09 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20151113 |