JP2017510611A5 - - Google Patents
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- JP2017510611A5 JP2017510611A5 JP2016561780A JP2016561780A JP2017510611A5 JP 2017510611 A5 JP2017510611 A5 JP 2017510611A5 JP 2016561780 A JP2016561780 A JP 2016561780A JP 2016561780 A JP2016561780 A JP 2016561780A JP 2017510611 A5 JP2017510611 A5 JP 2017510611A5
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- Prior art keywords
- compound
- aryl
- pharmaceutical composition
- alkyl
- cry
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 64
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 64
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 201000010099 disease Diseases 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 32
- 230000001404 mediated effect Effects 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 108010037139 Cryptochromes Proteins 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 20
- 101150078024 CRY2 gene Proteins 0.000 claims description 18
- 101150102464 Cry1 gene Proteins 0.000 claims description 18
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 16
- KCYOZNARADAZIZ-CWBQGUJCSA-N 2-[(2e,4e,6e,8e,10e,12e,14e)-15-(4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol Chemical compound O1C2(C)CC(O)CC(C)(C)C2=CC1C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C1C=C2C(C)(C)CCCC2(C)O1 KCYOZNARADAZIZ-CWBQGUJCSA-N 0.000 claims description 14
- KCYOZNARADAZIZ-PPBBKLJYSA-N Cryptochrome Natural products O[C@@H]1CC(C)(C)C=2[C@@](C)(O[C@H](/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(\C)/[C@H]3O[C@@]4(C)C(C(C)(C)CCC4)=C3)/C)\C)/C)C=2)C1 KCYOZNARADAZIZ-PPBBKLJYSA-N 0.000 claims description 14
- KCYOZNARADAZIZ-XZOHMNSDSA-N beta-cryptochrome Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C1OC2(C)CC(O)CC(C)(C)C2=C1)C=CC=C(/C)C3OC4(C)CCCC(C)(C)C4=C3 KCYOZNARADAZIZ-XZOHMNSDSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 208000010412 Glaucoma Diseases 0.000 claims description 8
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 8
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000012544 monitoring process Methods 0.000 claims description 8
- 230000003247 decreasing effect Effects 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 101150008094 per1 gene Proteins 0.000 claims description 6
- 108700005075 Regulator Genes Proteins 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 4
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- USUZGMWDZDXMDG-CYBMUJFWSA-N 4-[(5r)-6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl]-3-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC=C1[C@@H]1N2C=NC=C2CC1 USUZGMWDZDXMDG-CYBMUJFWSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000002177 Cataract Diseases 0.000 claims description 4
- JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 108010009911 Cytochrome P-450 CYP11B2 Proteins 0.000 claims description 4
- 102100024329 Cytochrome P450 11B2, mitochondrial Human genes 0.000 claims description 4
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- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims description 4
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- 108010049356 Steroid 11-beta-Hydroxylase Proteins 0.000 claims description 4
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- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 201000009101 diabetic angiopathy Diseases 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 201000002249 diabetic peripheral angiopathy Diseases 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims description 4
- 229960001690 etomidate Drugs 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229960004125 ketoconazole Drugs 0.000 claims description 4
- 229940038098 korlym Drugs 0.000 claims description 4
- 208000002780 macular degeneration Diseases 0.000 claims description 4
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
- 229960003105 metformin Drugs 0.000 claims description 4
- FJLBFSROUSIWMA-UHFFFAOYSA-N metyrapone Chemical compound C=1C=CN=CC=1C(C)(C)C(=O)C1=CC=CN=C1 FJLBFSROUSIWMA-UHFFFAOYSA-N 0.000 claims description 4
- 229960004465 metyrapone Drugs 0.000 claims description 4
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 claims description 4
- 229960000350 mitotane Drugs 0.000 claims description 4
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- NEEFMPSSNFRRNC-HQUONIRXSA-N pasireotide aspartate Chemical compound OC(=O)[C@@H](N)CC(O)=O.OC(=O)[C@@H](N)CC(O)=O.C([C@H]1C(=O)N2C[C@@H](C[C@H]2C(=O)N[C@H](C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@H](C(N[C@@H](CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(=O)N1)=O)CCCCN)C=1C=CC=CC=1)OC(=O)NCCN)C1=CC=CC=C1 NEEFMPSSNFRRNC-HQUONIRXSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000011477 surgical intervention Methods 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- FJVWQOQSMAKEAY-OXJNMPFZSA-N C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@](CN1C([C@H](CC1)F)=O)(C)O Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@](CN1C([C@H](CC1)F)=O)(C)O FJVWQOQSMAKEAY-OXJNMPFZSA-N 0.000 claims description 3
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- CTLHGLZELHMPOK-UHFFFAOYSA-N FC=1C=CC=2N(C3=CC=C(C=C3C2C1)F)CC(CN1C(C(CC1)F)=O)O Chemical compound FC=1C=CC=2N(C3=CC=C(C=C3C2C1)F)CC(CN1C(C(CC1)F)=O)O CTLHGLZELHMPOK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- -1 azido, hydroxyl Chemical group 0.000 claims description 3
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 3
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- MUVYYQQLOKRDQS-UHFFFAOYSA-N 1-[3-(3,6-difluorocarbazol-9-yl)-2-hydroxypropyl]imidazolidin-2-one Chemical compound FC=1C=CC=2N(C3=CC=C(C=C3C2C1)F)CC(CN1C(NCC1)=O)O MUVYYQQLOKRDQS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
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- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
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- WIBSYPXJJKRRRB-UHFFFAOYSA-N 3,6-difluoro-9h-carbazole Chemical compound C1=C(F)C=C2C3=CC(F)=CC=C3NC2=C1 WIBSYPXJJKRRRB-UHFFFAOYSA-N 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N ethyl-n-butyl-ketone Natural products CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims 1
- VLYOSQYVOMGGDB-MRTQMZDGSA-N (3S)-1-[(2S)-3-carbazol-9-yl-2-hydroxy-2-methylpropyl]-3-fluoropyrrolidin-2-one (4R)-1-[(2R)-3-carbazol-9-yl-2-hydroxypropyl]-4-methylimidazolidin-2-one Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@H](CN1C(N[C@@H](C1)C)=O)O.C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@](CN1C([C@H](CC1)F)=O)(C)O VLYOSQYVOMGGDB-MRTQMZDGSA-N 0.000 description 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461976350P | 2014-04-07 | 2014-04-07 | |
| US61/976,350 | 2014-04-07 | ||
| PCT/US2015/024537 WO2015157182A1 (en) | 2014-04-07 | 2015-04-06 | Carbazole-containing amides, carbamates, and ureas as cryptochrome modulators |
Related Child Applications (1)
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| CN111285793B (zh) * | 2019-03-01 | 2022-04-22 | 广州中医药大学(广州中医药研究院) | 氟取代双分子咔唑衍生物、其制备方法及应用 |
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