MX2013005773A - Inhibidores de kat ii. - Google Patents
Inhibidores de kat ii.Info
- Publication number
- MX2013005773A MX2013005773A MX2013005773A MX2013005773A MX2013005773A MX 2013005773 A MX2013005773 A MX 2013005773A MX 2013005773 A MX2013005773 A MX 2013005773A MX 2013005773 A MX2013005773 A MX 2013005773A MX 2013005773 A MX2013005773 A MX 2013005773A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- aryl
- compound
- mmol
- cycloalkyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 196
- 150000003839 salts Chemical class 0.000 claims abstract description 63
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- 208000025966 Neurological disease Diseases 0.000 claims abstract description 6
- 230000006735 deficit Effects 0.000 claims abstract description 4
- -1 heterocycloalkyloxy Chemical group 0.000 claims description 127
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
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- 208000010877 cognitive disease Diseases 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 230000007278 cognition impairment Effects 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 208000028698 Cognitive impairment Diseases 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
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- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 9
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
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- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 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 description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 238000007917 intracranial administration Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
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- 208000029578 Muscle disease Diseases 0.000 claims description 3
- 208000021642 Muscular disease Diseases 0.000 claims description 3
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
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- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 3
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 3
- 208000009205 Tinnitus Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 201000004810 Vascular dementia Diseases 0.000 claims description 3
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- 230000001154 acute effect Effects 0.000 claims description 3
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- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
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- 208000006752 brain edema Diseases 0.000 claims description 3
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- 230000007882 cirrhosis Effects 0.000 claims description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
- 230000036461 convulsion Effects 0.000 claims description 3
- 231100000868 delusion Toxicity 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 231100000040 eye damage Toxicity 0.000 claims description 3
- 230000010370 hearing loss Effects 0.000 claims description 3
- 231100000888 hearing loss Toxicity 0.000 claims description 3
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- 230000002218 hypoglycaemic effect Effects 0.000 claims description 3
- 230000028993 immune response Effects 0.000 claims description 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
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- 208000019116 sleep disease Diseases 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 210000000278 spinal cord Anatomy 0.000 claims description 3
- 231100000886 tinnitus Toxicity 0.000 claims description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- YEHNWRNMGIYLAL-NSHDSACASA-N (5s)-5-amino-2-benzyl-7-hydroxy-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound C([C@@H](C(N(O)C1=N2)=O)N)C1=CN2CC1=CC=CC=C1 YEHNWRNMGIYLAL-NSHDSACASA-N 0.000 claims 1
- VRCGFKBFAAAERR-LBPRGKRZSA-N (5s)-5-amino-3-benzyl-2-ethyl-7-hydroxy-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound C([C@H](N)C(=O)N(O)C1=NN2CC)C1=C2CC1=CC=CC=C1 VRCGFKBFAAAERR-LBPRGKRZSA-N 0.000 claims 1
- ABBLRYAESUTTSD-NSHDSACASA-N (5s)-5-amino-3-benzyl-7-hydroxy-1-methyl-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound O=C([C@@H](N)CC=12)N(O)C=1N(C)N=C2CC1=CC=CC=C1 ABBLRYAESUTTSD-NSHDSACASA-N 0.000 claims 1
- AUAOKUNOKVGYJP-JTQLQIEISA-N (5s)-5-amino-7-hydroxy-2-phenyl-4,5-dihydropyrazolo[3,4-b]pyridin-6-one Chemical compound C([C@@H](C(N(O)C1=N2)=O)N)C1=CN2C1=CC=CC=C1 AUAOKUNOKVGYJP-JTQLQIEISA-N 0.000 claims 1
- YAYRMUVEORJPCX-UHFFFAOYSA-N pyrazolo[3,4-b]pyridin-3-one Chemical compound C1=CC=C2C(=O)N=NC2=N1 YAYRMUVEORJPCX-UHFFFAOYSA-N 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 3
- 230000000626 neurodegenerative effect Effects 0.000 abstract description 3
- 230000001149 cognitive effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- 230000015572 biosynthetic process Effects 0.000 description 99
- 238000003786 synthesis reaction Methods 0.000 description 98
- 238000006243 chemical reaction Methods 0.000 description 75
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 54
- 239000007787 solid Substances 0.000 description 49
- 239000000203 mixture Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 42
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
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- 238000000746 purification Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
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- 238000003756 stirring Methods 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 150000001721 carbon Chemical group 0.000 description 16
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 16
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
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- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 8
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- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 8
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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Landscapes
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Applications Claiming Priority (2)
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| US41880210P | 2010-12-01 | 2010-12-01 | |
| PCT/IB2011/055158 WO2012073143A1 (en) | 2010-12-01 | 2011-11-17 | Kat ii inhibitors |
Publications (1)
| Publication Number | Publication Date |
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| MX2013005773A true MX2013005773A (es) | 2013-06-18 |
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| Application Number | Title | Priority Date | Filing Date |
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| MX2013005773A MX2013005773A (es) | 2010-12-01 | 2011-11-17 | Inhibidores de kat ii. |
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| SG190246A1 (en) | 2010-12-01 | 2013-06-28 | Pfizer | Kat ii inhibitors |
| EP2919788A4 (en) | 2012-11-14 | 2016-05-25 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR TREATING SCHIZOPHRENIA |
| EP3683222B1 (en) | 2014-04-23 | 2021-10-06 | Mitsubishi Tanabe Pharma Corporation | Novel bicyclic or tricyclic heterocyclic compound |
| WO2016164703A1 (en) | 2015-04-09 | 2016-10-13 | Eisai R & D Management Co., Ltd. | Fgfr4 inhibitors |
| WO2016164754A1 (en) | 2015-04-09 | 2016-10-13 | Eisai R&D Management Co., Ltd. | Fgfr4 inhibitors |
| JP6853782B2 (ja) * | 2015-10-22 | 2021-03-31 | 田辺三菱製薬株式会社 | 新規二環性複素環化合物 |
| WO2020257790A1 (en) * | 2019-06-20 | 2020-12-24 | University Of Kentucky Research Foundation | Pharmaceutically active pyrazolo-pyridone modulators of dcn1/2-mediated cullin neddylation |
| WO2021102258A1 (en) | 2019-11-22 | 2021-05-27 | Incyte Corporation | Combination therapy comprising an alk2 inhibitor and a jak2 inhibitor |
| BR112022022530A2 (pt) | 2020-05-05 | 2023-02-23 | Nuvalent Inc | Composto, composição farmacêutica, método de tratamento de câncer, método de inibição seletiva, método de redução de um nível de ros1 ou alk |
| EP4146626A4 (en) | 2020-05-05 | 2024-05-29 | Nuvalent, Inc. | CHEMOTHERAPEUTIC AGENTS BASED ON HETEROAROMATIC MACROCYCLIC ETHERS |
| WO2022165382A1 (en) * | 2021-01-29 | 2022-08-04 | Neurawell Therapeutics | Phenylethylidenehydrazine combination therapies |
| IL311444A (en) | 2021-10-01 | 2024-05-01 | Nuvalent Inc | Solid forms, pharmaceutical compositions and preparation of heteroaromatic macrocyclic ether compounds |
| US12435087B2 (en) | 2023-11-03 | 2025-10-07 | Cellarity, Inc. | Modulators of DCN-1 and methods of use thereof |
| WO2025096956A1 (en) | 2023-11-03 | 2025-05-08 | Cellarity, Inc. | Dcn-1 modulating compounds and methods of use thereof |
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| US5519055A (en) * | 1993-08-06 | 1996-05-21 | University Of Maryland At Baltimore | Substituted kynurenines and process for their preparation |
| EP1644335A4 (en) * | 2003-07-11 | 2008-06-04 | Bristol Myers Squibb Co | TETRAHYDROQUINOLINE DERIVATIVES COMPRISING MODULATORS OF CANNABINOID RECEPTORS |
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| CA2585557C (en) | 2004-10-28 | 2009-08-18 | Pharmacia & Upjohn Company Llc | Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors |
| CA2626897A1 (en) | 2005-11-03 | 2007-05-18 | Joshua Close | Histone deacetylase inhibitors with aryl-pyrazolyl motifs |
| US20090012075A1 (en) | 2006-01-12 | 2009-01-08 | Miller Thomas A | Fluorinated Arylamide Derivatives |
| US20100009969A1 (en) | 2006-07-27 | 2010-01-14 | Ucb Pharma, S.A. | Fused Oxazoles & Thiazoles As Histamine H3- Receptor Ligands |
| US20100273787A1 (en) * | 2007-11-15 | 2010-10-28 | Robert Schwarcz | Kynurenine-aminotransferase inhibitors |
| WO2009095752A1 (en) * | 2008-01-29 | 2009-08-06 | Glenmark Pharmaceuticals, S.A. | Fused pyrazole derivatives as cannabinoid receptor modulators |
| WO2010014688A2 (en) | 2008-07-30 | 2010-02-04 | Bal Seal Engineering | Canted coil multi-metallic wire |
| AP2012006071A0 (en) * | 2009-06-18 | 2012-02-29 | Pfizer | Bicyclic and tricyclic compounds as kat II inhibitors. |
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| WO2012073143A1 (en) | 2012-06-07 |
| US20140057938A1 (en) | 2014-02-27 |
| JP2013544277A (ja) | 2013-12-12 |
| EP2646443A1 (en) | 2013-10-09 |
| DK2646443T3 (en) | 2014-11-17 |
| US8598200B2 (en) | 2013-12-03 |
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