JP2019182869A5 - - Google Patents
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- Publication number
- JP2019182869A5 JP2019182869A5 JP2019104161A JP2019104161A JP2019182869A5 JP 2019182869 A5 JP2019182869 A5 JP 2019182869A5 JP 2019104161 A JP2019104161 A JP 2019104161A JP 2019104161 A JP2019104161 A JP 2019104161A JP 2019182869 A5 JP2019182869 A5 JP 2019182869A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- pyrrolidin
- propan
- dioxin
- dihydrobenzo
- 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.)
- Pending
Links
- -1 nitro, cyano, amino Chemical group 0.000 claims 91
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 58
- 150000001875 compounds Chemical class 0.000 claims 32
- 239000000203 mixture Substances 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 229930186217 Glycolipid Natural products 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims 4
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical group O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- BARFJUJHHGUHGZ-DNQXCXABSA-N C1(CC1)OC1=CC=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(C(=O)C1=CC=C(C=C1)C#C)=O)O Chemical compound C1(CC1)OC1=CC=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(C(=O)C1=CC=C(C=C1)C#C)=O)O BARFJUJHHGUHGZ-DNQXCXABSA-N 0.000 claims 2
- NQIAOBUVSQRBEP-VSGBNLITSA-N ClC=1C=C2C=CC(=CC2=CC=1)CCC(C(=O)N[C@@H]([C@H](O)C1=CC=C(C=C1)OC1CC1)CN1CCCC1)(F)F Chemical compound ClC=1C=C2C=CC(=CC2=CC=1)CCC(C(=O)N[C@@H]([C@H](O)C1=CC=C(C=C1)OC1CC1)CN1CCCC1)(F)F NQIAOBUVSQRBEP-VSGBNLITSA-N 0.000 claims 2
- VZEKRPWDBJDJSZ-ZJSXRUAMSA-N ClC=1C=CC2=C(SC(=C2)C(C(=O)N[C@@H]([C@H](O)C2=CC=C(C=C2)OC2CC2)CN2CCCC2)=O)C=1 Chemical compound ClC=1C=CC2=C(SC(=C2)C(C(=O)N[C@@H]([C@H](O)C2=CC=C(C=C2)OC2CC2)CN2CCCC2)=O)C=1 VZEKRPWDBJDJSZ-ZJSXRUAMSA-N 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- 206010038468 Renal hypertrophy Diseases 0.000 claims 2
- DSZIYURTTGVYOD-ZJSXRUAMSA-N S1C2=C(C=C1C(C(=O)N[C@@H]([C@H](O)C1=CC=C(C=C1)OC1CC1)CN1CCCC1)=O)C=CC=C2 Chemical compound S1C2=C(C=C1C(C(=O)N[C@@H]([C@H](O)C1=CC=C(C=C1)OC1CC1)CN1CCCC1)=O)C=CC=C2 DSZIYURTTGVYOD-ZJSXRUAMSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 201000008627 kidney hypertrophy Diseases 0.000 claims 2
- 230000001537 neural effect Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 208000030761 polycystic kidney disease Diseases 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- MCSDYGRIDDNDHG-VRUKGCPNSA-N 2-(5-chloro-1-benzofuran-2-yl)-2,2-dideuterio-N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]acetamide Chemical compound ClC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@H](O)C2=CC3=C(OCCO3)C=C2)CN2CCCC2)([2H])[2H])C=1 MCSDYGRIDDNDHG-VRUKGCPNSA-N 0.000 claims 1
- QDNHPVQKJZVCKI-KGACXCFTSA-N 2-(5-chloro-1-benzofuran-2-yl)-N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(2,2,5,5-tetradeuteriopyrrolidin-1-yl)propan-2-yl]-2,2-difluoroacetamide Chemical compound ClC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@H](O)C2=CC3=C(OCCO3)C=C2)CN2C(CCC2([2H])[2H])([2H])[2H])(F)F)C=1 QDNHPVQKJZVCKI-KGACXCFTSA-N 0.000 claims 1
- QDNHPVQKJZVCKI-WZONZLPQSA-N 2-(5-chloro-1-benzofuran-2-yl)-N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2,2-difluoroacetamide Chemical compound ClC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@H](O)C2=CC3=C(OCCO3)C=C2)CN2CCCC2)(F)F)C=1 QDNHPVQKJZVCKI-WZONZLPQSA-N 0.000 claims 1
- NOQURHLSURANJE-AUSIDOKSSA-N 2-(5-chloro-1-benzofuran-2-yl)-N-[(1R,2R)-1-(6-cyclopropyloxypyridin-3-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2-oxoacetamide Chemical compound ClC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@H](O)C=2C=NC(=CC=2)OC2CC2)CN2CCCC2)=O)C=1 NOQURHLSURANJE-AUSIDOKSSA-N 0.000 claims 1
- BNTFFRJCZUOBIK-YKSBVNFPSA-N 2-(5-chloro-1-benzofuran-2-yl)-N-[(1S,2R)-1-[3-chloro-4-(2-hydroxy-2-methylpropoxy)phenyl]-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2,2-difluoroacetamide Chemical compound ClC=1C=C(C=CC=1OCC(C)(C)O)[C@@H]([C@@H](CN1CCCC1)NC(C(F)(F)C=1OC2=C(C=1)C=C(C=C2)Cl)=O)O BNTFFRJCZUOBIK-YKSBVNFPSA-N 0.000 claims 1
- QDNHPVQKJZVCKI-UDOHKGTISA-N 2-(5-chloro-1-benzofuran-2-yl)-N-[(1S,2R)-1-deuterio-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2,2-difluoroacetamide Chemical compound ClC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@](O)([2H])C2=CC3=C(OCCO3)C=C2)CN2CCCC2)(F)F)C=1 QDNHPVQKJZVCKI-UDOHKGTISA-N 0.000 claims 1
- DGRUACDYDOCSJR-ZJSXRUAMSA-N 2-(5-chloro-1-benzothiophen-2-yl)-N-[(1R,2R)-1-(4-cyclopropyloxyphenyl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2-oxoacetamide Chemical compound ClC1=CC2=C(SC(=C2)C(C(=O)N[C@@H]([C@H](O)C2=CC=C(C=C2)OC2CC2)CN2CCCC2)=O)C=C1 DGRUACDYDOCSJR-ZJSXRUAMSA-N 0.000 claims 1
- OHKCCUULRFUCTD-JNKRKRSOSA-N 2-(5-chloro-2,3-dihydro-1H-inden-2-yl)-N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2,2-difluoroacetamide Chemical compound ClC=1C=C2CC(CC2=CC=1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C=C1)CN1CCCC1)(F)F OHKCCUULRFUCTD-JNKRKRSOSA-N 0.000 claims 1
- UUIZJYOQYAYVIS-JNKRKRSOSA-N 2-(5-chloro-2,3-dihydro-1H-inden-2-yl)-N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2-oxoacetamide Chemical compound ClC=1C=C2CC(CC2=CC=1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C=C1)CN1CCCC1)=O UUIZJYOQYAYVIS-JNKRKRSOSA-N 0.000 claims 1
- WFOOXDJHXKGNPD-WXEBLKNKSA-N 2-(5-chloro-2,3-dihydro-1H-inden-2-yl)-N-[(1R,2R)-1-(6-cyclopropyloxypyridin-3-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2-oxoacetamide Chemical compound ClC=1C=C2CC(CC2=CC=1)C(C(=O)N[C@@H]([C@H](O)C=1C=NC(=CC=1)OC1CC1)CN1CCCC1)=O WFOOXDJHXKGNPD-WXEBLKNKSA-N 0.000 claims 1
- QGBSUBCOOMHZCK-GGXMVOPNSA-N 2-[4-(1,3-dimethylindazol-5-yl)phenyl]-N-[(1R,2R)-1-(5-fluoro-2,3-dihydro-1,4-benzodioxin-7-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-2-oxoacetamide Chemical compound CN1N=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O)C QGBSUBCOOMHZCK-GGXMVOPNSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 102100022548 Beta-hexosaminidase subunit alpha Human genes 0.000 claims 1
- PZVSDNDODSUBOX-WZONZLPQSA-N BrC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@H](O)C2=CC3=C(OCCO3)C=C2)CN2CCCC2)(F)F)C=1 Chemical compound BrC=1C=CC2=C(C=C(O2)C(C(=O)N[C@@H]([C@H](O)C2=CC3=C(OCCO3)C=C2)CN2CCCC2)(F)F)C=1 PZVSDNDODSUBOX-WZONZLPQSA-N 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- DNOPTJGAFSUSHT-XRKRLSELSA-N C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O DNOPTJGAFSUSHT-XRKRLSELSA-N 0.000 claims 1
- FBPSOIAWTBNWHH-XRKRLSELSA-N C1(CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O Chemical compound C1(CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O FBPSOIAWTBNWHH-XRKRLSELSA-N 0.000 claims 1
- GMKNBHRFPGFKNV-AOYPEHQESA-N C1(CC1)N1N=C(C=C1)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O Chemical compound C1(CC1)N1N=C(C=C1)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O GMKNBHRFPGFKNV-AOYPEHQESA-N 0.000 claims 1
- JJLIXUIDEGFQSH-POURPWNDSA-N C1(CC1)N1N=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O Chemical compound C1(CC1)N1N=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O JJLIXUIDEGFQSH-POURPWNDSA-N 0.000 claims 1
- MCGZPNYXBJJOLH-IXCJQBJRSA-N C1(CC1)OC1=C(C=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)=O)O)C(F)(F)F Chemical compound C1(CC1)OC1=C(C=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)=O)O)C(F)(F)F MCGZPNYXBJJOLH-IXCJQBJRSA-N 0.000 claims 1
- FJUOAIGYXQOSQR-VSGBNLITSA-N C1(CC1)OC1=CC=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)=O)O Chemical compound C1(CC1)OC1=CC=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)=O)O FJUOAIGYXQOSQR-VSGBNLITSA-N 0.000 claims 1
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- YVNMDIOWYDBFSO-AZZTXQJBSA-N C12N(CC(CC1)C2)C[C@H]([C@H](O)C1=CC2=C(OCCO2)C=C1)NC(C(F)(F)C=1OC2=C(C=1)C=C(C=C2)Cl)=O Chemical compound C12N(CC(CC1)C2)C[C@H]([C@H](O)C1=CC2=C(OCCO2)C=C1)NC(C(F)(F)C=1OC2=C(C=1)C=C(C=C2)Cl)=O YVNMDIOWYDBFSO-AZZTXQJBSA-N 0.000 claims 1
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- OXFAVUXNALHHNE-IXCJQBJRSA-N CC(C)(C)OC1=C(Cl)C=C(C=C1)[C@@H](O)[C@@H](CN1CCCC1)NC(=O)C(=O)C1=CC=C(C=C1)C1=CC=C(F)C=C1 Chemical compound CC(C)(C)OC1=C(Cl)C=C(C=C1)[C@@H](O)[C@@H](CN1CCCC1)NC(=O)C(=O)C1=CC=C(C=C1)C1=CC=C(F)C=C1 OXFAVUXNALHHNE-IXCJQBJRSA-N 0.000 claims 1
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- IFBJSXGXFLOYGZ-GGXMVOPNSA-N CN1N=C(C2=CC=C(C=C12)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O)C Chemical compound CN1N=C(C2=CC=C(C=C12)C1=CC=C(C=C1)C(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)=O)C IFBJSXGXFLOYGZ-GGXMVOPNSA-N 0.000 claims 1
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| RU2578947C2 (ru) | 2008-10-03 | 2016-03-27 | Джензайм Корпорейшн | Ингибиторы глюкозилцерамидсинтазы 2-ациламинопропанольного типа |
| MX381242B (es) * | 2009-11-27 | 2025-03-12 | Genzyme Corp | Una forma amorfa y una cristalina de hemitartrato de genz 112638 como inhibidor de glucosilceramida sintasa. |
| US20110144081A1 (en) * | 2009-12-15 | 2011-06-16 | Henner Knust | Pyrrolidine derivatives |
| US8961959B2 (en) * | 2011-10-17 | 2015-02-24 | The Regents Of The University Of Michigan | Glucosylceramide synthase inhibitors and therapeutic methods using the same |
| EP2968268B1 (en) * | 2013-03-15 | 2020-07-29 | Concert Pharmaceuticals Inc. | Inhibitors of the enzyme udp-glucose: n-acyl-sphingosine glucosyltransferase |
| MX374452B (es) * | 2013-09-20 | 2025-03-06 | Biomarin Pharm Inc | Inhibidores de glucosilceramida sintasa para el tratamiento de enfermedades. |
-
2014
- 2014-09-19 MX MX2016003486A patent/MX374452B/es active IP Right Grant
- 2014-09-19 US US15/023,337 patent/US10227323B2/en active Active
- 2014-09-19 CA CA2924545A patent/CA2924545C/en active Active
- 2014-09-19 EP EP21177756.0A patent/EP3912977A1/en active Pending
- 2014-09-19 WO PCT/US2014/056555 patent/WO2015042397A1/en not_active Ceased
- 2014-09-19 CN CN201910659073.4A patent/CN110372636B/zh active Active
- 2014-09-19 TW TW103132529A patent/TWI690511B/zh active
- 2014-09-19 TW TW108108615A patent/TW201945337A/zh unknown
- 2014-09-19 CN CN201480063521.XA patent/CN105745206B/zh active Active
- 2014-09-19 JP JP2016515409A patent/JP6537500B2/ja active Active
- 2014-09-19 EP EP14789439.8A patent/EP3046920B1/en active Active
- 2014-09-19 AU AU2014321397A patent/AU2014321397C1/en active Active
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2016
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2019
- 2019-01-31 US US16/264,505 patent/US10927092B2/en active Active
- 2019-05-06 AU AU2019203155A patent/AU2019203155A1/en not_active Abandoned
- 2019-06-04 JP JP2019104161A patent/JP2019182869A/ja active Pending
- 2019-07-29 IL IL268340A patent/IL268340A/en unknown
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