CA2893333C - Carbocyclic-and heterocyclic-substituted hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds - Google Patents
Carbocyclic-and heterocyclic-substituted hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds Download PDFInfo
- Publication number
- CA2893333C CA2893333C CA2893333A CA2893333A CA2893333C CA 2893333 C CA2893333 C CA 2893333C CA 2893333 A CA2893333 A CA 2893333A CA 2893333 A CA2893333 A CA 2893333A CA 2893333 C CA2893333 C CA 2893333C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- tautomer
- hexahydropyrano
- thiazin
- mmol
- 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.)
- Expired - Fee Related
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- QRXWUHYBXASSFN-UHFFFAOYSA-N 1,2,4,4a,5,6-hexahydropyrano[3,4-d][1,3]thiazin-2-amine Chemical class O1CCC2CSC(N)NC2=C1 QRXWUHYBXASSFN-UHFFFAOYSA-N 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 236
- 238000011282 treatment Methods 0.000 claims abstract description 40
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- 101000894883 Homo sapiens Beta-secretase 2 Proteins 0.000 claims abstract description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 17
- 102100021277 Beta-secretase 2 Human genes 0.000 claims abstract description 16
- 230000000694 effects Effects 0.000 claims abstract description 13
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
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- 230000004770 neurodegeneration Effects 0.000 claims abstract description 9
- 208000037765 diseases and disorders Diseases 0.000 claims abstract description 4
- 238000011321 prophylaxis Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 97
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- WADGHWKXQZVKFK-UHFFFAOYSA-N thiazin-2-amine Chemical compound NN1SC=CC=C1 WADGHWKXQZVKFK-UHFFFAOYSA-N 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- YUFWDCBIDOXDCY-VAHXTSCQSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,4,6-trifluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC(F)=CC=2F)F)CC1 YUFWDCBIDOXDCY-VAHXTSCQSA-N 0.000 claims 1
- RHJJDGACVHKXNA-JJMVLAAESA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC(F)=CC=2)F)CC1 RHJJDGACVHKXNA-JJMVLAAESA-N 0.000 claims 1
- WAKCJWZQPHOJBN-JJMVLAAESA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,5-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC=C(F)C=2)F)CC1 WAKCJWZQPHOJBN-JJMVLAAESA-N 0.000 claims 1
- CEUHNOFRRAIAQB-WNMQOVRZSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,6-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC=CC=2F)F)CC1 CEUHNOFRRAIAQB-WNMQOVRZSA-N 0.000 claims 1
- JRBPZKILTJVDPX-MJEQTWJJSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2-fluoro-4-methylphenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound FC1=CC(C)=CC=C1[C@@]1(N=C(N)SC2)[C@H]2C[C@H](C2CC2)OC1 JRBPZKILTJVDPX-MJEQTWJJSA-N 0.000 claims 1
- FHXGFQTXPUMEKT-PEYYIBSZSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2-fluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC=CC=2)F)CC1 FHXGFQTXPUMEKT-PEYYIBSZSA-N 0.000 claims 1
- AZAGZNAIHZPHML-YSVLISHTSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(3-fluoro-4-methylphenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1=C(F)C(C)=CC=C1[C@@]1(N=C(N)SC2)[C@H]2C[C@H](C2CC2)OC1 AZAGZNAIHZPHML-YSVLISHTSA-N 0.000 claims 1
- FTTYFEBEIFPZEG-JGGQBBKZSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(4-fluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C=CC(F)=CC=2)CC1 FTTYFEBEIFPZEG-JGGQBBKZSA-N 0.000 claims 1
- DXFOXQOXOOZOFO-SQWLQELKSA-N (4ar,6r,8as)-6-cyclopropyl-8a-phenyl-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C=CC=CC=2)CC1 DXFOXQOXOOZOFO-SQWLQELKSA-N 0.000 claims 1
- DZPLYXXEXZWQOK-WRASPQICSA-N (4ar,6r,8as)-8a-(2,4-difluorophenyl)-6-(oxetan-2-yl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC(F)=CC=2)F)CCO1 DZPLYXXEXZWQOK-WRASPQICSA-N 0.000 claims 1
- AYIXLNDRJRRIAH-FKXQQNEVSA-N (4ar,6r,8as)-8a-(2,4-difluorophenyl)-6-(oxolan-2-yl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC(F)=CC=2)F)CCCO1 AYIXLNDRJRRIAH-FKXQQNEVSA-N 0.000 claims 1
- PUQDUPUSQUJKLG-BNLOLNQZSA-N (4ar,6s,8as)-6-(cyclopropylmethyl)-8a-(2,4-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C([C@@H]1OC[C@@]2(N=C(SC[C@@H]2C1)N)C=1C(=CC(F)=CC=1)F)C1CC1 PUQDUPUSQUJKLG-BNLOLNQZSA-N 0.000 claims 1
- HENOYKTZLIYYIJ-URNHKWKMSA-N (4r,4ar,6r,8as)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4-methyl-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(N)S[C@@H]([C@@H]3C2)C)C=2C(=CC(F)=CC=2)F)CC1 HENOYKTZLIYYIJ-URNHKWKMSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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| US201261739053P | 2012-12-19 | 2012-12-19 | |
| US61/739,053 | 2012-12-19 | ||
| PCT/IB2013/060633 WO2014097038A1 (en) | 2012-12-19 | 2013-12-04 | CARBOCYCLIC- AND HETEROCYCLIC-SUBSTITUTED HEXAHYDROPYRANO[3,4-d][1,3]THIAZIN-2-AMINE COMPOUNDS |
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| JP6374889B2 (ja) | 2013-03-08 | 2018-08-15 | アムジエン・インコーポレーテツド | β−セクレターゼ阻害剤としての過フッ素化シクロプロピル縮合１，３−オキサジン−２−アミン化合物、及び使用方法 |
| CA2944971C (en) | 2014-04-10 | 2019-05-07 | Pfizer Inc. | 2-amino-6-methyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8h)-yl-1,3-thiazol-4-yl amides |
| US9550762B2 (en) | 2014-08-08 | 2017-01-24 | Amgen, Inc. | Cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| WO2017024180A1 (en) | 2015-08-06 | 2017-02-09 | Amgen Inc. | Vinyl fluoride cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| EP3353183A1 (en) | 2015-09-24 | 2018-08-01 | Pfizer Inc | N-[2-(2-amino-6,6-disubstituted-4, 4a, 5, 6-tetrahydropyrano [3,4-d][1,3]thiazin-8a (8h)-yl) -1, 3-thiazol-4-yl]amides |
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| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | 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 |
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2013
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- 2013-12-04 US US14/653,549 patent/US9403846B2/en not_active Expired - Fee Related
- 2013-12-04 EP EP13817734.0A patent/EP2935282A1/en not_active Withdrawn
Also Published As
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| EP2935282A1 (en) | 2015-10-28 |
| WO2014097038A1 (en) | 2014-06-26 |
| US9403846B2 (en) | 2016-08-02 |
| JP2016503785A (ja) | 2016-02-08 |
| CA2893333A1 (en) | 2014-06-26 |
| US20160002264A1 (en) | 2016-01-07 |
| JP6162820B2 (ja) | 2017-07-12 |
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