ES2444370T3 - Antagonistas del receptor de histamina 3 - Google Patents
Antagonistas del receptor de histamina 3Info
- Publication number
- ES2444370T3 ES2444370T3 ES06809114.9T ES06809114T ES2444370T3 ES 2444370 T3 ES2444370 T3 ES 2444370T3 ES 06809114 T ES06809114 T ES 06809114T ES 2444370 T3 ES2444370 T3 ES 2444370T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrrolidin
- ylmethyl
- phenyl
- fluoro
- alkyl
- 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.)
- Active
Links
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 title claims description 30
- 229960001340 histamine Drugs 0.000 title claims description 15
- 229940044551 receptor antagonist Drugs 0.000 title description 7
- 239000002464 receptor antagonist Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 43
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 41
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 150000002367 halogens Chemical class 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- -1 Trans -3- (3-Fluoro-4-pyrrolidin-1-ylmethyl-phenyl) -cyclobutanecarboxylic acid diethylamide Chemical compound 0.000 claims description 73
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 16
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 15
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 11
- 208000010877 cognitive disease Diseases 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 208000019022 Mood disease Diseases 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 208000027744 congestion Diseases 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 206010028735 Nasal congestion Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 230000000172 allergic effect Effects 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
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- 206010015037 epilepsy Diseases 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 208000019116 sleep disease Diseases 0.000 claims description 5
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- XRMDMTCGEGVPTG-SHTZXODSSA-N C1[C@@H](C(=O)NC)C[C@@H]1C(C=C1Cl)=CC=C1CN1CCCC1 Chemical compound C1[C@@H](C(=O)NC)C[C@@H]1C(C=C1Cl)=CC=C1CN1CCCC1 XRMDMTCGEGVPTG-SHTZXODSSA-N 0.000 claims description 3
- OJRPDHQTDAAMDC-SHTZXODSSA-N C1[C@@H](C(=O)NC)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 Chemical compound C1[C@@H](C(=O)NC)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 OJRPDHQTDAAMDC-SHTZXODSSA-N 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 3
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 3
- 201000003152 motion sickness Diseases 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 2
- 206010014561 Emphysema Diseases 0.000 claims description 2
- 208000001953 Hypotension Diseases 0.000 claims description 2
- 230000009858 acid secretion Effects 0.000 claims description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 2
- 208000002173 dizziness Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000036543 hypotension Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 206010039083 rhinitis Diseases 0.000 claims description 2
- RIXGVBHJROIWQJ-HDJSIYSDSA-N C1[C@@H](C(=O)N(C)C)C[C@@H]1C(C(=C1Cl)Cl)=CC=C1CN1CCCC1 Chemical compound C1[C@@H](C(=O)N(C)C)C[C@@H]1C(C(=C1Cl)Cl)=CC=C1CN1CCCC1 RIXGVBHJROIWQJ-HDJSIYSDSA-N 0.000 claims 1
- YMADPMQZDGZXGA-QAQDUYKDSA-N C1[C@@H](C(=O)N(C)CC)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 Chemical compound C1[C@@H](C(=O)N(C)CC)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 YMADPMQZDGZXGA-QAQDUYKDSA-N 0.000 claims 1
- TXHMDZKZRUSEKH-IYARVYRRSA-N C1[C@@H](C(=O)NCC(C)C)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 Chemical compound C1[C@@H](C(=O)NCC(C)C)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 TXHMDZKZRUSEKH-IYARVYRRSA-N 0.000 claims 1
- AIRLEJUEYAYZHG-WKILWMFISA-N C1[C@@H](C(=O)NCC)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 Chemical compound C1[C@@H](C(=O)NCC)C[C@@H]1C(C=C1F)=CC=C1CN1CCCC1 AIRLEJUEYAYZHG-WKILWMFISA-N 0.000 claims 1
- CTFYCSIEHFVGBY-ATZDWAIDSA-N C[C@@H]1CCCN1Cc1ccc(cc1Cl)[C@H]1C[C@@H](C1)C(=O)N1CCCC1 Chemical compound C[C@@H]1CCCN1Cc1ccc(cc1Cl)[C@H]1C[C@@H](C1)C(=O)N1CCCC1 CTFYCSIEHFVGBY-ATZDWAIDSA-N 0.000 claims 1
- ONWPVDGOTPAEFA-RRQZDWCRSA-N FC1=CC([C@@H]2C[C@H](C2)C(=O)N2CC3CCC(CC3)C2)=CC=C1CN1CCCC1 Chemical compound FC1=CC([C@@H]2C[C@H](C2)C(=O)N2CC3CCC(CC3)C2)=CC=C1CN1CCCC1 ONWPVDGOTPAEFA-RRQZDWCRSA-N 0.000 claims 1
- LAVQTQXRZLRCQN-IYARVYRRSA-N Fc1cc(ccc1CN1CCCC1)[C@H]1C[C@@H](C1)C(=O)N1CCCC1 Chemical compound Fc1cc(ccc1CN1CCCC1)[C@H]1C[C@@H](C1)C(=O)N1CCCC1 LAVQTQXRZLRCQN-IYARVYRRSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 390
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 367
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 323
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 192
- 235000019439 ethyl acetate Nutrition 0.000 description 180
- 239000000203 mixture Substances 0.000 description 147
- 239000000243 solution Substances 0.000 description 144
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 118
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 110
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 85
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 56
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 55
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- 102000004384 Histamine H3 receptors Human genes 0.000 description 22
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- KKGRJTTXRRMYJD-UHFFFAOYSA-N 3-[3-chloro-4-(pyrrolidin-1-ylmethyl)phenyl]-3-hydroxycyclobutane-1-carboxylic acid Chemical compound C1C(C(=O)O)CC1(O)C(C=C1Cl)=CC=C1CN1CCCC1 KKGRJTTXRRMYJD-UHFFFAOYSA-N 0.000 description 16
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- XNGFKGOUEXMDQK-UHFFFAOYSA-N [3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]-pyrrolidin-1-ylmethanone Chemical compound FC1=CC(C2(F)CC(C2)C(=O)N2CCCC2)=CC=C1CN1CCCC1 XNGFKGOUEXMDQK-UHFFFAOYSA-N 0.000 description 7
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- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
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Landscapes
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- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73099605P | 2005-10-27 | 2005-10-27 | |
| US730996P | 2005-10-27 | ||
| PCT/IB2006/002977 WO2007049123A1 (en) | 2005-10-27 | 2006-10-16 | Histamine-3 receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2444370T3 true ES2444370T3 (es) | 2014-02-24 |
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|---|---|---|---|
| ES06809114.9T Active ES2444370T3 (es) | 2005-10-27 | 2006-10-16 | Antagonistas del receptor de histamina 3 |
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| US8158673B2 (en) * | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| KR101108109B1 (ko) * | 2007-01-22 | 2012-02-06 | 화이자 프로덕츠 인코포레이티드 | 치료 화합물의 토실레이트 염 및 이의 약학 조성물 |
| EP2123644B1 (en) | 2007-03-07 | 2014-12-17 | Takeda Pharmaceutical Company Limited | Benzoxazepine derivatives and use thereof |
| BRPI0815591B8 (pt) | 2007-08-22 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, e, uso de um composto. |
| CN101939306A (zh) * | 2007-12-07 | 2011-01-05 | 美国辉瑞有限公司 | 反式-n-异丁基-3-氟-3-[3-氟-4-(吡咯烷-1-基-甲基)-苯基]环丁烷甲酰胺的甲苯磺酸盐 |
| CA2721303C (en) * | 2008-05-08 | 2016-06-28 | Evotec Ag | Azetidines and cyclobutanes as histamine h3 receptor antagonists |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| AU2011218492B2 (en) | 2010-02-18 | 2014-11-13 | Astrazeneca Ab | New crystalline form of a cyclopropyl benzamide derivative |
| WO2012131539A1 (en) | 2011-03-31 | 2012-10-04 | Pfizer Inc. | Novel bicyclic pyridinones |
| WO2012172449A1 (en) | 2011-06-13 | 2012-12-20 | Pfizer Inc. | Lactams as beta secretase inhibitors |
| WO2013030713A1 (en) | 2011-08-31 | 2013-03-07 | Pfizer Inc. | Hexahydropyrano [3,4-d][1,3] thiazin-2-amine compounds |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| CA2872154C (en) | 2012-05-04 | 2016-08-23 | Pfizer Inc. | Heterocyclic substituted hexahydropyrano [3,4-d] [1,3] thiazin-2-amine compounds as inhibitors of app, bace1 and bace2 |
| MD20140130A2 (ro) | 2012-06-29 | 2015-04-30 | Pfizer Inc. | 4-(amino-substituite)-7H-pirolo[2,3-d]pirimidine noi ca inhibitori de LRRK2 |
| WO2014045162A1 (en) | 2012-09-20 | 2014-03-27 | Pfizer Inc. | ALKYL-SUBSTITUTED HEXAHYDROPYRANO[3,4-d] [1,3]THIAZIN-2-ANIME COMPOUNDS |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| EP2931731A1 (en) | 2012-12-11 | 2015-10-21 | Pfizer Inc. | Hexahydropyrano [3,4-d][1,3]thiazin-2-amine compounds as inhibitors of bace1 |
| JP6162820B2 (ja) | 2012-12-19 | 2017-07-12 | ファイザー・インク | 炭素環式および複素環式置換ヘキサヒドロピラノ[3,4−d][1,3]チアジン−2−アミン化合物 |
| WO2014125394A1 (en) | 2013-02-13 | 2014-08-21 | Pfizer Inc. | HETEROARYL-SUBSTITUTED HEXAHYDROPYRANO [3,4-d][1,3] THIAZIN-2-AMINE COMPOUNDS |
| US9233981B1 (en) | 2013-02-15 | 2016-01-12 | Pfizer Inc. | Substituted phenyl hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
| EA201591360A1 (ru) | 2013-02-19 | 2016-03-31 | Пфайзер Инк. | Азабензимидазолы в качестве ингибиторов изозимов фдэ4 для лечения цнс и других расстройств |
| JP6425717B2 (ja) | 2013-10-04 | 2018-11-21 | ファイザー・インク | ガンマセクレターゼモジュレーターとしての新規二環式ピリジノン |
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| US8158673B2 (en) * | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| KR101108109B1 (ko) * | 2007-01-22 | 2012-02-06 | 화이자 프로덕츠 인코포레이티드 | 치료 화합물의 토실레이트 염 및 이의 약학 조성물 |
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