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
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- 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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| AU2011336217B2 (en) | 2010-12-01 | 2015-10-01 | Pfizer Inc. | KAT II inhibitors |
| HK1215170A1 (zh) | 2012-11-14 | 2016-08-19 | The Johns Hopkins University | 治療精神分裂症的方法和組合物 |
| MX381182B (es) * | 2014-04-23 | 2025-03-12 | Mitsubishi Tanabe Pharma Corp | Compuesto heterociclico biciclico o triciclico novedoso. |
| 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 |
| US10793582B2 (en) | 2015-10-22 | 2020-10-06 | Mitsubishi Tanabe Pharma Corporation | Bicyclic heterocyclic compound |
| WO2020257790A1 (en) * | 2019-06-20 | 2020-12-24 | University Of Kentucky Research Foundation | Pharmaceutically active pyrazolo-pyridone modulators of dcn1/2-mediated cullin neddylation |
| PH12022551052A1 (en) | 2019-11-22 | 2023-05-29 | Incyte Corp | Combination therapy comprising an alk2 inhibitor and a jak2 inhibitor |
| KR102698413B1 (ko) | 2020-05-05 | 2024-08-26 | 뉴베일런트, 아이엔씨. | 헤테로방향족 거대환식 에터 화학치료제 |
| CA3179700A1 (en) | 2020-05-05 | 2021-11-11 | Nuvalent, Inc. | Heteroaromatic macrocyclic ether chemotherapeutic agents |
| WO2022165382A1 (en) * | 2021-01-29 | 2022-08-04 | Neurawell Therapeutics | Phenylethylidenehydrazine combination therapies |
| WO2023056405A1 (en) | 2021-10-01 | 2023-04-06 | 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 |
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| US5519055A (en) * | 1993-08-06 | 1996-05-21 | University Of Maryland At Baltimore | Substituted kynurenines and process for their preparation |
| US20050014786A1 (en) * | 2003-07-11 | 2005-01-20 | Chongqing Sun | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
| GT200500186A (es) | 2004-07-07 | 2006-03-02 | Regimenes anticonceptivos con antagonistas del receptor de progesterona y kits | |
| WO2006046135A2 (en) | 2004-10-28 | 2006-05-04 | Pharmacia & Upjohn Company Llc | Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors |
| EP1945617B1 (en) | 2005-11-03 | 2012-12-26 | Merck Sharp & Dohme Corp. | Histone deacetylase inhibitors with aryl-pyrazolyl motifs |
| CA2635209A1 (en) | 2006-01-12 | 2007-08-02 | Merck & Co., Inc. | Fluorinated arylamide derivatives |
| EP2049548A1 (en) | 2006-07-27 | 2009-04-22 | 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 |
| US9293849B2 (en) | 2008-07-30 | 2016-03-22 | Bal Seal Engineering, Inc. | Electrical connector using a canted coil multi-metallic wire |
| KR101390023B1 (ko) * | 2009-06-18 | 2014-04-29 | 화이자 인코포레이티드 | 키누레닌 아미노트랜스퍼라제 ｉｉ 억제제로서 이환식 및 삼환식 화합물 |
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