AU2010207507B2 - Amino-heterocyclic compounds used as PDE9 inhibitors - Google Patents
Amino-heterocyclic compounds used as PDE9 inhibitors Download PDFInfo
- Publication number
- AU2010207507B2 AU2010207507B2 AU2010207507A AU2010207507A AU2010207507B2 AU 2010207507 B2 AU2010207507 B2 AU 2010207507B2 AU 2010207507 A AU2010207507 A AU 2010207507A AU 2010207507 A AU2010207507 A AU 2010207507A AU 2010207507 B2 AU2010207507 B2 AU 2010207507B2
- Authority
- AU
- Australia
- Prior art keywords
- pyrazolo
- pyrimidin
- dihydro
- ethyl
- cyclopentyl
- 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.)
- Ceased
Links
- 229940076380 PDE9 inhibitor Drugs 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 186
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 101100407341 Drosophila melanogaster Pde9 gene Proteins 0.000 claims abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 135
- -1 cyano, carboxy Chemical group 0.000 claims description 121
- 239000000203 mixture Substances 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 125000001188 haloalkyl group Chemical group 0.000 claims description 39
- 241000124008 Mammalia Species 0.000 claims description 36
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 claims description 31
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 230000002708 enhancing effect Effects 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
- 230000001737 promoting effect Effects 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 210000004556 brain Anatomy 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 claims description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 208000028698 Cognitive impairment Diseases 0.000 claims description 3
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 230000019771 cognition Effects 0.000 claims description 3
- 150000003997 cyclic ketones Chemical class 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 229960004640 memantine Drugs 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 229960001685 tacrine Drugs 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 229960004136 rivastigmine Drugs 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- DXLLBBOOAFAHQM-GOEBONIOSA-N 6-[(1S)-1-[(3R)-3-(2-chlorophenoxy)pyrrolidin-1-yl]ethyl]-1-cyclopentyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound O([C@@H]1CCN(C1)[C@@H](C)C=1NC(=O)C=2C=NN(C=2N=1)C1CCCC1)C1=CC=CC=C1Cl DXLLBBOOAFAHQM-GOEBONIOSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- HJXAXXUTIBEZHT-GFCCVEGCSA-N chembl2180070 Chemical compound C1N([C@H](C)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)CC1C1=NC=CC=N1 HJXAXXUTIBEZHT-GFCCVEGCSA-N 0.000 claims 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 1
- 229960003530 donepezil Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229960003980 galantamine Drugs 0.000 claims 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims 1
- JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 claims 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 202
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
- 239000000243 solution Substances 0.000 description 115
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 104
- 238000005481 NMR spectroscopy Methods 0.000 description 98
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 53
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Classifications
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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Landscapes
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| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| MY173229A (en) | 2008-11-19 | 2020-01-07 | Forum Pharmaceuticals Inc | Treatment of cognitive disorders with (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| RU2011150248A (ru) * | 2009-05-11 | 2013-06-20 | Энвиво Фармасьютикалз, Инк. | Лечение когнитивных расстройств с определенными рецепторами альфа-7 никотиновой кислоты в комбинации с ингибиторами ацетилхолинэстеразы |
| PT3029039T (pt) | 2010-05-17 | 2017-11-28 | Forum Pharmaceuticals Inc | Formulações farmacêuticas que compreendem formas cristalinas de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida mono-hidratado |
| CN103097383B (zh) | 2010-09-07 | 2015-09-16 | 安斯泰来制药株式会社 | 吡唑并喹啉化合物 |
| CN103097393B (zh) | 2010-09-07 | 2015-09-16 | 安斯泰来制药株式会社 | 喹喔啉化合物 |
| AU2012323085B2 (en) | 2011-10-10 | 2017-03-09 | H. Lundbeck A/S | PDE9i with imidazo pyrazinone backbone |
| AP2014007820A0 (en) | 2012-01-26 | 2014-07-31 | Lundbeck & Co As H | PDE9 inhibitors with imidazo triazinone backbone |
| JP2015505564A (ja) | 2012-02-03 | 2015-02-23 | テバ ファーマシューティカル インダストリーズ リミティド | 第一選択の抗ＴＮＥα療法に失敗したクローン病患者を治療するためのラキニモドの使用 |
| EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
| WO2014024125A1 (en) | 2012-08-08 | 2014-02-13 | Celon Pharma S.A. | Pyrazolo[4,3-d]pyrimidin-7(6h)-one derivatives as pde9 inhibitors |
| CN102786525B (zh) * | 2012-08-08 | 2014-12-17 | 中山大学 | N-取代吡唑并[3,4-d]嘧啶酮类化合物、其制备方法及其应用 |
| TW201410244A (zh) * | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| EP2908827A4 (en) * | 2012-10-19 | 2016-08-31 | Celus Pharmaceuticals Inc | VITAMIN D ANALOGUE FOR THE TREATMENT OF A NEUROLOGICAL DISEASE |
| CN103207246B (zh) * | 2012-12-21 | 2017-10-10 | 北京万全德众医药生物技术有限公司 | 一种用液相色谱法分离测定鲁拉西酮及其光学异构体的方法 |
| CA2944714C (en) * | 2014-05-06 | 2023-05-16 | Anthony G. Visco | Methods of treating or preventing preterm labor |
| BR112017000160A2 (pt) * | 2014-08-27 | 2017-10-31 | Hoffmann La Roche | derivados de azetidina substituidos como ligantes de taar |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| US10513524B2 (en) | 2015-07-07 | 2019-12-24 | H. Lundbeck A/S | PDE9 inhibitors with imidazo triazinone backbone and imidazo pyrazinone backbone for treatment of peripheral diseases |
| US10370337B2 (en) | 2015-07-29 | 2019-08-06 | Merck, Sharp & Dohme Corp. | Oxy-cyanoquinolinone PDE9 inhibitors |
| US10376504B2 (en) | 2015-07-29 | 2019-08-13 | Merck, Sharp & Dohme Corp. | Substituted quinolinones as PDE9 inhibitors |
| WO2017019724A1 (en) * | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Phenyl-cyanoquinolinone pde9 inhibitors |
| US10662146B2 (en) | 2015-09-15 | 2020-05-26 | Praxis Bioresearch, LLC | Prodrugs of fencamfamine |
| CN105467028A (zh) * | 2015-11-18 | 2016-04-06 | 北京万全德众医药生物技术有限公司 | 气相色谱法分离测定鲁拉西酮中间体光学异构体的方法 |
| CN105669680B (zh) * | 2016-03-24 | 2018-02-23 | 南京药捷安康生物科技有限公司 | 吡咯并[2,1‑f][1,2,4]三嗪‑4(1H)‑酮衍生物类PDE9A抑制剂 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| CA3025586A1 (en) | 2016-07-06 | 2018-01-11 | Imara, Inc. | Pde9 inhibitors for treatment of peripheral diseases |
| WO2018073251A1 (en) * | 2016-10-18 | 2018-04-26 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
| DK3532064T3 (da) | 2016-10-28 | 2020-08-24 | H Lundbeck As | Kombinationsbehandlinger omfattende imidazopyrazinoner til behandlingen af psykiatriske og/eller kognitive lidelser |
| EP3532053A1 (en) | 2016-10-28 | 2019-09-04 | H. Lundbeck A/S | Combination treatments comprising administration of imidazopyrazinones |
| CN109963834B (zh) | 2016-11-18 | 2023-04-14 | 综合研究实验室瑞典股份公司 | 可用作皮质儿茶酚胺能神经传递调节剂的新型氮杂环丁烷衍生物 |
| MX390582B (es) | 2016-12-28 | 2025-03-20 | Dart Neuroscience Llc Star | Compuestos de pirazolopirimidinona sustituida como inhibidores de fosfodiesterasas 2 (pde2) |
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