CA2882386C - Substituted pyrido[1,2-a]pyrazines and their use in the treatment of neurodegenerative and/or neurological disorders - Google Patents
Substituted pyrido[1,2-a]pyrazines and their use in the treatment of neurodegenerative and/or neurological disorders Download PDFInfo
- Publication number
- CA2882386C CA2882386C CA2882386A CA2882386A CA2882386C CA 2882386 C CA2882386 C CA 2882386C CA 2882386 A CA2882386 A CA 2882386A CA 2882386 A CA2882386 A CA 2882386A CA 2882386 C CA2882386 C CA 2882386C
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- CA
- Canada
- Prior art keywords
- methyl
- mmol
- pharmaceutically acceptable
- acceptable salt
- phenyl
- 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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- 208000012902 Nervous system disease Diseases 0.000 title description 9
- 208000025966 Neurological disease Diseases 0.000 title description 8
- 208000015122 neurodegenerative disease Diseases 0.000 title description 7
- 230000000626 neurodegenerative effect Effects 0.000 title description 7
- PJEAHOHAPYWSEB-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrazine Chemical class C1=CC=CN2CC=NC=C21 PJEAHOHAPYWSEB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 219
- 150000003839 salts Chemical class 0.000 claims abstract description 64
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- -1 C3-C6cycloalkyl Chemical group 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000001153 fluoro group Chemical group F* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 208000024827 Alzheimer disease Diseases 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 208000020016 psychiatric disease Diseases 0.000 claims description 7
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims description 5
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- QOPCXWBRHZVEQH-SZFUDVHCSA-N 2-[(1s)-1-[(2s,5r)-5-(4-chloro-3,5-difluorophenyl)oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC(F)=C(Cl)C(F)=C1 QOPCXWBRHZVEQH-SZFUDVHCSA-N 0.000 claims 2
- PBCQGLLRQCGBRF-SZFUDVHCSA-N 2-[(1s)-1-[(2s,5r)-5-[3,5-difluoro-4-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC(F)=C(C(F)(F)F)C(F)=C1 PBCQGLLRQCGBRF-SZFUDVHCSA-N 0.000 claims 2
- KWLOJYBMOANZSC-JQOQJDEVSA-N 2-[(1s)-1-[(2s,5r)-5-[4,5-difluoro-2-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC(F)=C(F)C=C1C(F)(F)F KWLOJYBMOANZSC-JQOQJDEVSA-N 0.000 claims 2
- MUDLWRHYTYCFBR-UZQPLGKSSA-N 2-[(1s)-1-[(2s,5r)-5-[4-chloro-2-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC=C(Cl)C=C1C(F)(F)F MUDLWRHYTYCFBR-UZQPLGKSSA-N 0.000 claims 2
- AKCDDYGYIGPEKL-JQOQJDEVSA-N 2-[(1s)-1-[(2s,5r)-5-[4-chloro-5-fluoro-2-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC(F)=C(Cl)C=C1C(F)(F)F AKCDDYGYIGPEKL-JQOQJDEVSA-N 0.000 claims 2
- HDGHLFQAIWQFDC-UZQPLGKSSA-N 2-[(1s)-1-[(2s,5r)-5-[4-fluoro-2-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC=C(F)C=C1C(F)(F)F HDGHLFQAIWQFDC-UZQPLGKSSA-N 0.000 claims 2
- 208000007930 Type C Niemann-Pick Disease Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- SKHXUJLZBBPBLM-PNHOKKKMSA-N 2-[(1s)-1-[(2s,5r)-5-[4-chloro-3-fluoro-2-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC=C(Cl)C(F)=C1C(F)(F)F SKHXUJLZBBPBLM-PNHOKKKMSA-N 0.000 claims 1
- CZCJRJMKFMFGOG-WQTXXOFMSA-N 7-(4-methylimidazol-1-yl)-2-[(1s)-1-[(2s,5r)-5-[4-(trifluoromethyl)phenyl]oxolan-2-yl]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1([C@H]2CC[C@H](O2)[C@H](C)N2C(C=3N(C(C(N4C=C(C)N=C4)=CC=3)=O)CC2)=O)=CC=C(C(F)(F)F)C=C1 CZCJRJMKFMFGOG-WQTXXOFMSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 146
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- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- REZGGXNDEMKIQB-UHFFFAOYSA-N zaprinast Chemical compound CCCOC1=CC=CC=C1C1=NC(=O)C2=NNNC2=N1 REZGGXNDEMKIQB-UHFFFAOYSA-N 0.000 description 1
- 229950005371 zaprinast Drugs 0.000 description 1
- BPKIMPVREBSLAJ-QTBYCLKRSA-N ziconotide Chemical compound C([C@H]1C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]2C(=O)N[C@@H]3C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@H](C(N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC2)C(N)=O)=O)CSSC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CSSC3)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(N1)=O)CCSC)[C@@H](C)O)C1=CC=C(O)C=C1 BPKIMPVREBSLAJ-QTBYCLKRSA-N 0.000 description 1
- 229960002811 ziconotide Drugs 0.000 description 1
- 229950009086 zicronapine Drugs 0.000 description 1
- 229960002791 zimeldine Drugs 0.000 description 1
- OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
- 229950007059 zonampanel Drugs 0.000 description 1
- 229960002911 zonisamide Drugs 0.000 description 1
- UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1
- XZVHHLNLLVICFA-SNVBAGLBSA-N α-difluoromethyl-dopa Chemical compound FC(F)[C@](C(O)=O)(N)CC1=CC=C(O)C(O)=C1 XZVHHLNLLVICFA-SNVBAGLBSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261703969P | 2012-09-21 | 2012-09-21 | |
| US61/703,969 | 2012-09-21 | ||
| PCT/IB2013/058347 WO2014045156A1 (en) | 2012-09-21 | 2013-09-06 | Novel bicyclic pyridinones |
Publications (2)
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|---|---|
| CA2882386A1 CA2882386A1 (en) | 2014-03-27 |
| CA2882386C true CA2882386C (en) | 2017-11-28 |
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| CA2882386A Active CA2882386C (en) | 2012-09-21 | 2013-09-06 | Substituted pyrido[1,2-a]pyrazines and their use in the treatment of neurodegenerative and/or neurological disorders |
Country Status (46)
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| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| ES2608356T3 (es) | 2012-12-20 | 2017-04-10 | Janssen Pharmaceutica Nv | Novedosos derivados tricíclicos de 3,4-dihidro-2H-pirido[1,2-a]pirazin-1,6-diona como moduladores de la secretasa gamma |
| AU2014206834B2 (en) | 2013-01-17 | 2017-06-22 | Janssen Pharmaceutica Nv | Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| EP3052495B1 (en) * | 2013-10-04 | 2019-06-26 | Pfizer Inc | Novel bicyclic pyridinones as gamma-secretase modulators |
| US10562897B2 (en) | 2014-01-16 | 2020-02-18 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| AP2016009465A0 (en) * | 2014-04-01 | 2016-09-30 | Pfizer | Chromene and 1,1 a,2,7b-tetrahydrocyclopropa[c]chromene pyridopyrazinediones as gamma-secretase modulators |
| KR102000382B1 (ko) * | 2015-02-03 | 2019-07-15 | 화이자 인코포레이티드 | 신규 시클로프로파벤조푸라닐 피리도피라진디온 |
| WO2016201168A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmceuticals Inc. | Oxadiazine compounds and methods of use thereof |
| JP7018026B2 (ja) | 2016-06-16 | 2022-02-09 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | ヘテロアリールエストロゲン受容体モジュレーター及びその使用 |
| IL267253B2 (en) * | 2016-12-16 | 2023-04-01 | Pipeline Therapeutics Inc | Methods for treating cochlear synaptopathy |
| US20220192984A1 (en) | 2018-10-02 | 2022-06-23 | Frequency Therapeutics, Inc. | Pharmaceutical compositions comprising otic therapeutic agents and related methods |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CA3136424A1 (en) | 2019-04-08 | 2020-10-15 | Frequency Therapeutics, Inc. | Combination of chir99021 and valproic acid for treating hearing loss |
| FI4069691T3 (fi) | 2019-12-06 | 2024-11-13 | Vertex Pharma | Substituoituja tetrahydrofuraaneja natriumkanavien modulaattoreina |
| CN113402490B (zh) * | 2021-03-29 | 2023-01-03 | 白银京宇新药业有限公司 | 一种1，2，6，7-四氢-8H-茚并[5，4-b]呋喃-8-酮的制备方法 |
| CR20230586A (es) | 2021-06-04 | 2024-05-07 | Vertex Pharma | N-(hydroxyalquil (hetero)aril) tetrahidrofurano carboxamidas como moduladores de canales de sodio |
| CN114034792B (zh) * | 2021-11-09 | 2024-06-25 | 山东新华制药股份有限公司 | 检测氯酮含量的液相色谱分析方法 |
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