ES2775674T3 - Compuestos de 6,7-dihidro-5H-pirazolo[5,1-b][1,3]oxazina-2-carboxamida - Google Patents
Compuestos de 6,7-dihidro-5H-pirazolo[5,1-b][1,3]oxazina-2-carboxamida Download PDFInfo
- Publication number
- ES2775674T3 ES2775674T3 ES17711330T ES17711330T ES2775674T3 ES 2775674 T3 ES2775674 T3 ES 2775674T3 ES 17711330 T ES17711330 T ES 17711330T ES 17711330 T ES17711330 T ES 17711330T ES 2775674 T3 ES2775674 T3 ES 2775674T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrazolo
- dihydro
- optionally substituted
- carboxamide
- oxazin
- 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.)
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- VYMFHYCOVQSQTL-UHFFFAOYSA-N 6,7-dihydro-5h-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical class O1CCCN2N=C(C(=O)N)C=C21 VYMFHYCOVQSQTL-UHFFFAOYSA-N 0.000 title description 2
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 211
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 68
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 125000001424 substituent group Chemical group 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 65
- 102100029168 cAMP-specific 3',5'-cyclic phosphodiesterase 4B Human genes 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- PHRSCPGZAINQTD-UHFFFAOYSA-N 2H-1,3-oxazine-2-carboxamide Chemical compound O1C(N=CC=C1)C(=O)N PHRSCPGZAINQTD-UHFFFAOYSA-N 0.000 claims description 39
- 238000011282 treatment Methods 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 15
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 101001098805 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4A Proteins 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 102100037092 cAMP-specific 3',5'-cyclic phosphodiesterase 4A Human genes 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 101000988423 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4C Proteins 0.000 claims description 5
- 102100029169 cAMP-specific 3',5'-cyclic phosphodiesterase 4C Human genes 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- JROPBYGZSRBHDV-UHFFFAOYSA-N oxazine-2-carboxamide Chemical compound NC(=O)N1OC=CC=C1 JROPBYGZSRBHDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000011117 substance-related disease Diseases 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
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- 206010013663 drug dependence Diseases 0.000 claims description 4
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- 208000006673 asthma Diseases 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- YNTJKQDWYXUTLZ-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC(Cl)=C1 YNTJKQDWYXUTLZ-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 101000988424 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4B Proteins 0.000 claims 1
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- 230000007815 allergy Effects 0.000 claims 1
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- PUPFATUGTIQBQA-UZQPLGKSSA-N fluorophen Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@H]2[C@@H]1C)CN2CCC1=CC=C(F)C=C1 PUPFATUGTIQBQA-UZQPLGKSSA-N 0.000 claims 1
- BKXVVCILCIUCLG-UHFFFAOYSA-N raloxifene hydrochloride Chemical class [H+].[Cl-].C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 BKXVVCILCIUCLG-UHFFFAOYSA-N 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 23
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 208000035475 disorder Diseases 0.000 description 50
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- 108010029485 Protein Isoforms Proteins 0.000 description 48
- 102000001708 Protein Isoforms Human genes 0.000 description 48
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 45
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 238000005160 1H NMR spectroscopy Methods 0.000 description 40
- 239000007787 solid Substances 0.000 description 40
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- 102100029170 cAMP-specific 3',5'-cyclic phosphodiesterase 4D Human genes 0.000 description 35
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
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- 125000006413 ring segment Chemical group 0.000 description 22
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 229910052801 chlorine Inorganic materials 0.000 description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
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Landscapes
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| SI1481992T1 (sl) | 2000-02-24 | 2017-01-31 | Washington University St. Louis | Humanizirana protitelesa, ki vežejo amiloidni peptid beta |
| DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
| JP4708675B2 (ja) | 2000-11-03 | 2011-06-22 | プロテオテック・インコーポレーテッド | ウンカリア・トメントーサおよび関連植物からアミロイド阻害化合物を単離する方法ならびに単離した化合物の使用 |
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| HRP20120174T1 (hr) * | 2006-03-09 | 2012-03-31 | Eisai R&D Management Co. | Derivat policikličnog cinamida |
| EP2007749A2 (en) | 2006-03-13 | 2008-12-31 | Pfizer Products Inc. | Tetralines antagonists of the h-3 receptor |
| CA2649775C (en) | 2006-04-21 | 2011-05-31 | Pfizer Products Inc. | Pyridine[3,4-b]pyrazinones |
| WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
| WO2008090429A1 (en) | 2007-01-22 | 2008-07-31 | Pfizer Products Inc. | Tosylate salt of a therapeutic compound and pharmaceutical compositions thereof |
| AU2009252938B2 (en) * | 2008-05-27 | 2012-04-26 | Astrazeneca Ab | Phenoxypyridinylamide derivatives and their use in the treatment of PDE4 mediated disease states |
| TW201102387A (en) * | 2009-06-08 | 2011-01-16 | Medicinova Inc | Substituted pyrazolo[1,5-a]pyridine compounds having multi-target activity |
| TWI532725B (zh) | 2010-01-26 | 2016-05-11 | 賽諾菲阿凡提斯公司 | 經氧取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| MA38333A1 (fr) * | 2013-02-19 | 2017-02-28 | Pfizer | Composés d'azabenzimidazole en tant qu'inhibiteurs d'isozymes pde4 pour le traitement de troubles du snc et d'autres affections |
| US9879009B2 (en) * | 2014-07-30 | 2018-01-30 | Mochida Pharmaceutical Co., Ltd. | Pyrazole derivative manufacturing method |
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| ZA201804619B (en) | 2020-12-23 |
| CN113332292A (zh) | 2021-09-03 |
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| US20190055262A1 (en) | 2019-02-21 |
| PL3419979T3 (pl) | 2020-06-29 |
| EP3419979B1 (en) | 2020-01-29 |
| RU2018128781A (ru) | 2020-03-24 |
| MX379704B (es) | 2025-03-11 |
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| CA3015166A1 (en) | 2018-08-31 |
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| IL260536B (en) | 2020-10-29 |
| RU2719599C2 (ru) | 2020-04-21 |
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| KR102148587B1 (ko) | 2020-08-26 |
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| SG11201806383TA (en) | 2018-09-27 |
| AU2017223132A1 (en) | 2018-07-26 |
| MX2018010177A (es) | 2019-01-21 |
| CN108699080A (zh) | 2018-10-23 |
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