CA2703477C - Pyridinyl substituted tropane compounds and uses thereof - Google Patents
Pyridinyl substituted tropane compounds and uses thereof Download PDFInfo
- Publication number
- CA2703477C CA2703477C CA2703477A CA2703477A CA2703477C CA 2703477 C CA2703477 C CA 2703477C CA 2703477 A CA2703477 A CA 2703477A CA 2703477 A CA2703477 A CA 2703477A CA 2703477 C CA2703477 C CA 2703477C
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- CA
- Canada
- Prior art keywords
- optionally substituted
- alkyl
- amino
- endo
- azabicyclo
- Prior art date
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- 150000003813 tropane derivatives Chemical class 0.000 title abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 title description 4
- 230000000694 effects Effects 0.000 claims abstract description 478
- 150000001875 compounds Chemical class 0.000 claims abstract description 243
- 101710113864 Heat shock protein 90 Proteins 0.000 claims abstract description 111
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims abstract description 7
- -1 alkylaminoalkylamino Chemical group 0.000 claims description 612
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 341
- 125000000217 alkyl group Chemical group 0.000 claims description 270
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 187
- 229910052736 halogen Inorganic materials 0.000 claims description 142
- 150000002367 halogens Chemical class 0.000 claims description 142
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 131
- 150000003839 salts Chemical class 0.000 claims description 128
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 113
- 125000003545 alkoxy group Chemical group 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 70
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 68
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
- 201000010099 disease Diseases 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 39
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims description 38
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 37
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 210000004027 cell Anatomy 0.000 claims description 27
- 125000003386 piperidinyl group Chemical group 0.000 claims description 27
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
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- 241001465754 Metazoa Species 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 15
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 15
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 15
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 230000001594 aberrant effect Effects 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000003944 tolyl group Chemical group 0.000 claims description 14
- 230000004906 unfolded protein response Effects 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
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- 125000004043 oxo group Chemical group O=* 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
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
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- 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
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 206010044412 transitional cell carcinoma Diseases 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical class C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 description 1
- 208000022271 tubular adenoma Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 208000009540 villous adenoma Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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Landscapes
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Applications Claiming Priority (3)
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| US68707P | 2007-10-25 | 2007-10-25 | |
| US61/000,687 | 2007-10-25 | ||
| PCT/US2008/012221 WO2009055077A1 (en) | 2007-10-25 | 2008-10-27 | Tropane compounds |
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| CA2703477A1 CA2703477A1 (en) | 2009-04-30 |
| CA2703477C true CA2703477C (en) | 2016-10-11 |
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| CA2703477A Active CA2703477C (en) | 2007-10-25 | 2008-10-27 | Pyridinyl substituted tropane compounds and uses thereof |
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| EP2231666B1 (en) * | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| 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 |
| CN108136055A (zh) * | 2015-07-16 | 2018-06-08 | 阿库鲁制药公司 | 用连接有标记、细胞毒或免疫调节基团的slc6a3配体检测与治疗肾细胞癌 |
| 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 |
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| 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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