ES2342348T3 - Compuestos de tropano. - Google Patents
Compuestos de tropano. Download PDFInfo
- Publication number
- ES2342348T3 ES2342348T3 ES08832769T ES08832769T ES2342348T3 ES 2342348 T3 ES2342348 T3 ES 2342348T3 ES 08832769 T ES08832769 T ES 08832769T ES 08832769 T ES08832769 T ES 08832769T ES 2342348 T3 ES2342348 T3 ES 2342348T3
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- Spain
- Prior art keywords
- optionally substituted
- alkyl
- amino
- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 294
- 238000000034 method Methods 0.000 claims abstract description 306
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- -1 alkylaminoalkylamino Chemical group 0.000 claims description 797
- 125000000217 alkyl group Chemical group 0.000 claims description 262
- 229910052736 halogen Inorganic materials 0.000 claims description 150
- 150000002367 halogens Chemical group 0.000 claims description 143
- 150000003839 salts Chemical class 0.000 claims description 133
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 122
- 101710113864 Heat shock protein 90 Proteins 0.000 claims description 101
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 94
- 125000003545 alkoxy group Chemical group 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 74
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 33
- 150000002431 hydrogen Chemical group 0.000 claims description 31
- 210000004027 cell Anatomy 0.000 claims description 30
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000003386 piperidinyl group Chemical group 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 230000005764 inhibitory process Effects 0.000 claims description 25
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 102000013498 tau Proteins Human genes 0.000 claims description 24
- 108010026424 tau Proteins Proteins 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 17
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 17
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 17
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 17
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 230000001594 aberrant effect Effects 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical group N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 12
- 230000004906 unfolded protein response Effects 0.000 claims description 12
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 125000002393 azetidinyl group Chemical group 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 8
- 206010018338 Glioma Diseases 0.000 claims description 7
- 238000009825 accumulation Methods 0.000 claims description 7
- 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 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
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- 206010040047 Sepsis Diseases 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 5
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- 102000001253 Protein Kinase Human genes 0.000 claims description 5
- 241001493065 dsRNA viruses Species 0.000 claims description 5
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 5
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 108060006633 protein kinase Proteins 0.000 claims description 5
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 4
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 4
- 108020005544 Antisense RNA Proteins 0.000 claims description 4
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
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- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 4
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 4
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 4
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- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 3
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- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 3
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- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
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Landscapes
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| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| UY32940A (es) | 2009-10-27 | 2011-05-31 | Bayer Cropscience Ag | Amidas sustituidas con halogenoalquilo como insecticidas y acaricidas |
| RU2012146986A (ru) | 2010-04-05 | 2014-05-20 | Сионоги Энд Ко., Лтд. | Цефемовые соединения, содержащие катехольную группу |
| EP2640366A2 (en) | 2010-11-15 | 2013-09-25 | Exelixis, Inc. | Benzoxazepines as inhibitors of pi3k/mtor and methods of their use and manufacture |
| EP2740474A1 (en) | 2012-12-05 | 2014-06-11 | Instituto Europeo di Oncologia S.r.l. | Cyclopropylamine derivatives useful as inhibitors of histone demethylases kdm1a |
| US20150352086A1 (en) * | 2013-01-07 | 2015-12-10 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Heat shock protein (hsp) inhibition and monitoring effectiveness thereof |
| MX2016002199A (es) | 2013-08-21 | 2016-07-13 | Alios Biopharma Inc | Compuestos antivirales. |
| AU2014348232A1 (en) * | 2013-11-18 | 2016-06-30 | Del Mar Pharmaceuticals | HPLC analysis of impurities in dianhydrogalactitol |
| EP2949648A1 (en) | 2014-05-30 | 2015-12-02 | IEO - Istituto Europeo di Oncologia Srl | Cyclopropylamine derivatives as histone demethylase inhibitors |
| JP6320570B2 (ja) | 2014-05-30 | 2018-05-09 | イエオ−イスティトゥート・エウロペオ・ディ・オンコロジア・エッセ・エッレ・エッレ | ヒストンデメチラーゼ阻害剤としてのシクロプロピルアミン化合物 |
| TW201625243A (zh) | 2014-10-14 | 2016-07-16 | 艾克塞里克斯公司 | 用於治療黑素瘤之藥物組合 |
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| EP3588064B1 (en) * | 2017-02-23 | 2022-09-07 | IHI Corporation | Oh radical detection probe, oh radical measurement device, and oh radical measurement method |
| CN108164529B (zh) * | 2017-12-25 | 2020-04-24 | 三峡大学 | 一种小分子抑制剂sld9059及其在制药中的应用 |
| US11466012B2 (en) | 2018-01-10 | 2022-10-11 | Allinky Biopharma | Tetrahydroisoquinoline compounds |
| CN111825702A (zh) * | 2019-04-22 | 2020-10-27 | 成都科岭源医药技术有限公司 | 一种氮杂*并吲唑类衍生物及其制备方法和用途 |
| CN110698395B (zh) * | 2019-10-22 | 2021-05-25 | 杭州百诚医药科技股份有限公司 | 一种托吡司特的中间体的制备方法 |
| CN112920078A (zh) * | 2019-12-05 | 2021-06-08 | 武汉珈汇精化科技有限公司 | 一种制备4-氰基苯甲酸甲酯的方法和一种制备4-氰基苯甲酸的方法 |
| TW202136238A (zh) * | 2020-01-06 | 2021-10-01 | 大陸商廣東東陽光藥業有限公司 | RORγt抑制劑及其製備方法和用途 |
| CN116615422A (zh) * | 2020-10-14 | 2023-08-18 | 珃诺生物医药科技(杭州)有限公司 | 用于靶向蛋白降解的方法和组合物 |
| CN114591192B (zh) * | 2020-12-04 | 2024-06-21 | 江西仰立新材料有限公司 | 一种n-环丙甲基苯胺类化合物的制备方法 |
| US20240083910A1 (en) * | 2020-12-18 | 2024-03-14 | Merck Sharp & Dohme Llc | Amido-substituted pyridyl compounds and methods of use thereof for the treatment of herpesviruses |
| CN112707809B (zh) * | 2020-12-30 | 2023-08-29 | 丽珠集团新北江制药股份有限公司 | 一种制备噁唑啉杀虫剂氟雷拉纳中间体的方法 |
| CA3226271A1 (en) | 2021-07-26 | 2023-02-02 | Zoetis Services Llc | Serotonin 5-ht2b inhibitory compounds |
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| EP0101641A3 (en) | 1982-07-22 | 1984-03-28 | Beecham Group Plc | Sulfonylamino-aza-bicyclo-alkyl derivatives |
| FR2738569B1 (fr) | 1995-09-12 | 1997-11-28 | Pf Medicament | Nouveaux derives naphtamide de 3 beta-amino azabicyclo octane ou nonane, leur procede de preparation, leur utilisation a titre de medicament antipsychotique |
| CN1104430C (zh) | 1996-01-15 | 2003-04-02 | 詹森药业有限公司 | 抑制血管生成的哒嗪胺 |
| HUP0202001A2 (hu) * | 2002-06-14 | 2005-08-29 | Sanofi-Aventis | DDP-IV gátló hatású azabiciklooktán- és nonánszármazékok |
| EP1626970B1 (en) | 2003-05-28 | 2009-07-08 | Theravance, Inc. | Azabicycloalkane compounds as muscarinic receptor antagonists |
| CA2530023A1 (en) * | 2003-06-24 | 2004-12-29 | Neurosearch A/S | Novel 8-aza-bicyclo[3.2.1]octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| EA009941B1 (ru) * | 2003-10-03 | 2008-04-28 | Пфайзер Инк. | Имидазопиридинзамещённые тропановые производные, обладающие активностью антагониста ccr5 рецептора, для лечения вируса иммунодефицита человека (вич) и воспаления |
| GB0323236D0 (en) * | 2003-10-03 | 2003-11-05 | Pfizer Ltd | Chemical compounds |
| CN1938292B (zh) * | 2004-03-31 | 2011-10-05 | 日本曹达株式会社 | 环胺化合物和有害生物防除剂 |
| FR2873693B1 (fr) * | 2004-07-29 | 2006-09-15 | Sanofi Synthelabo | Derives d'amino-tropane, leur preparation et leur application en therapeutique |
| US7713990B2 (en) | 2005-01-13 | 2010-05-11 | Neurosearch A/S | 3,8-substituted 8-AZA-bicyclo[3.2.1]octane derivatives and their use as monomine neurotransmitter re-uptake inhibitors |
| CN102127078A (zh) * | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| EA014057B1 (ru) * | 2005-10-06 | 2010-08-30 | Ниппон Сода Ко., Лтд. | Поперечно связанные соединения циклических аминов и средства для борьбы с вредителями |
| CN101511818B (zh) * | 2006-09-01 | 2013-05-08 | 大塚农业科技株式会社 | N-吡啶基哌啶化合物、其制备方法及有害生物防治剂 |
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