AU2010236346B2 - 4-azetidinyl-1-phenyl-cyclohexane antagonists of CCR2 - Google Patents
4-azetidinyl-1-phenyl-cyclohexane antagonists of CCR2 Download PDFInfo
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- AU2010236346B2 AU2010236346B2 AU2010236346A AU2010236346A AU2010236346B2 AU 2010236346 B2 AU2010236346 B2 AU 2010236346B2 AU 2010236346 A AU2010236346 A AU 2010236346A AU 2010236346 A AU2010236346 A AU 2010236346A AU 2010236346 B2 AU2010236346 B2 AU 2010236346B2
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- Prior art keywords
- alkyl
- phenyl
- prepared
- compound
- azetidin
- 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.)
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- RVGRTRHVBFCARF-UHFFFAOYSA-N tert-butyl n-[3-[1-hydroxy-4-[3-[[2-[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]azetidin-1-yl]cyclohexyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(C2(O)CCC(CC2)N2CC(C2)NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 RVGRTRHVBFCARF-UHFFFAOYSA-N 0.000 description 1
- UTIHCTRYKUFLAC-UHFFFAOYSA-N tert-butyl n-[4-(4-oxocyclohexyl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1CCC(=O)CC1 UTIHCTRYKUFLAC-UHFFFAOYSA-N 0.000 description 1
- HVBXXWMWVBGLLZ-UHFFFAOYSA-N tert-butyl n-[4-[1-hydroxy-4-[3-[[2-[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]azetidin-1-yl]cyclohexyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1(O)CCC(N2CC(C2)NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 HVBXXWMWVBGLLZ-UHFFFAOYSA-N 0.000 description 1
- HFBIJLSEAJTCDR-UHFFFAOYSA-N tert-butyl n-[4-[4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]azetidin-1-yl]cyclohexyl]phenyl]carbamate Chemical compound C1C(NC(=O)OC(C)(C)C)CN1C1CCC(C=2C=CC(NC(=O)OC(C)(C)C)=CC=2)CC1 HFBIJLSEAJTCDR-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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Applications Claiming Priority (3)
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| US17030709P | 2009-04-17 | 2009-04-17 | |
| US61/170,307 | 2009-04-17 | ||
| PCT/US2010/031265 WO2010121046A1 (en) | 2009-04-17 | 2010-04-15 | 4-azetidinyl-1-phenyl-cyclohexane antagonists of ccr2 |
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| AU2010236346A1 AU2010236346A1 (en) | 2011-11-03 |
| AU2010236346B2 true AU2010236346B2 (en) | 2015-01-22 |
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| JP (1) | JP5675773B2 (https=) |
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| NZ (1) | NZ595432A (https=) |
| TW (1) | TW201102377A (https=) |
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| WO2010068663A1 (en) * | 2008-12-10 | 2010-06-17 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-heteroaryl-cyclohexanol antagonists of ccr2 |
| MX2011010919A (es) * | 2009-04-16 | 2011-11-02 | Janssen Pharmaceutica Nv | Antagonistas del receptor 2 de citocina quimioatrayente de 4-azetidinil-1-heteroaril-ciclohexano. |
| WO2010121036A1 (en) | 2009-04-17 | 2010-10-21 | Janssen Pharmaceutica Nv | 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2 |
| CN102459227B (zh) | 2009-04-17 | 2014-08-20 | 詹森药业有限公司 | Ccr2的4-氮杂环丁烷基-1-苯基-环己烷拮抗剂 |
| TW201211027A (en) * | 2010-06-09 | 2012-03-16 | Janssen Pharmaceutica Nv | Cyclohexyl-azetidinyl antagonists of CCR2 |
| TW201204717A (en) | 2010-06-17 | 2012-02-01 | Janssen Pharmaceutica Nv | Cyclohexyl-azetidinyl antagonists of CCR2 |
| CA2852160A1 (en) | 2011-10-28 | 2013-05-02 | Galderma Research & Development | New leukocyte infiltrate markers for rosacea and uses thereof |
| AU2012338581B2 (en) | 2011-11-18 | 2016-12-08 | Nxera Pharma Uk Limited | Muscarinic M1 receptor agonists |
| DK2785710T3 (en) * | 2011-12-01 | 2017-12-04 | Chemocentryx Inc | SUBSTITUTED BENZIMIDAZOLES AND BENZOPYRAZOLES AS CCR (4) - ANTAGONISTS |
| ES2690315T3 (es) | 2012-06-15 | 2018-11-20 | Mitsubishi Tanabe Pharma Corporation | Compuestos de imidazol y triazol como inhibidores de DGAT-1 |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| KR20200087273A (ko) | 2014-10-24 | 2020-07-20 | 란도스 바이오파마, 인크. | 란티오닌 합성효소 c-유사 2-계 치료제 |
| ES2764840T3 (es) | 2015-01-28 | 2020-06-04 | Univ Bordeaux | Uso de plerixafor para tratar y/o prevenir exacerbaciones agudas de la enfermedad pulmonar obstructiva crónica |
| ES2904252T3 (es) | 2015-05-21 | 2022-04-04 | Chemocentryx Inc | Moduladores de CCR2 |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| US10259787B2 (en) | 2016-10-14 | 2019-04-16 | Heptares Therapeutics Limited | Substituted cyclohexanes as muscarinic M1 receptor and/or M4 receptor agonists |
| CN118267479A (zh) | 2017-09-25 | 2024-07-02 | 凯莫森特里克斯股份有限公司 | 使用趋化因子受体2(ccr2)拮抗剂和pd-1/pd-l1抑制剂的联合治疗 |
| BR112020010983A2 (pt) | 2017-11-30 | 2020-11-17 | Landos Biopharma, Inc | método in vitro para gerar células preparadas a partir de células precursoras, células isoladas e método para tratar uma afecção em um animal com as células isoladas |
| IL275898B2 (en) | 2018-01-08 | 2025-05-01 | Chemocentryx Inc | Methods for treating solid tumors with CCR2 antagonists |
| US20190269664A1 (en) | 2018-01-08 | 2019-09-05 | Chemocentryx, Inc. | Methods of treating solid tumors with ccr2 antagonists |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| CN110028395A (zh) * | 2019-05-29 | 2019-07-19 | 宁夏中星显示材料有限公司 | 一种4-(4-羟基苯基)环己酮的制备方法 |
| BR112022002387A2 (pt) | 2019-12-20 | 2022-09-06 | Landos Biopharma Inc | Composto da fórmula z-y-q-y' ou um sal ou éster farmaceuticamente aceitável do mesmo |
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- 2010-04-15 US US12/761,080 patent/US20100267689A1/en not_active Abandoned
- 2010-04-15 BR BRPI1016189A patent/BRPI1016189A2/pt not_active Application Discontinuation
- 2010-04-15 EP EP10714804.1A patent/EP2419419B1/en active Active
- 2010-04-15 AU AU2010236346A patent/AU2010236346B2/en not_active Ceased
- 2010-04-15 JP JP2012506232A patent/JP5675773B2/ja not_active Expired - Fee Related
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- 2010-04-15 NZ NZ595432A patent/NZ595432A/en not_active IP Right Cessation
- 2010-04-16 TW TW099111898A patent/TW201102377A/zh unknown
- 2010-04-19 AR ARP100101287A patent/AR076328A1/es unknown
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| WO2010121046A1 (en) | 2010-10-21 |
| US20120040960A1 (en) | 2012-02-16 |
| CA2758934A1 (en) | 2010-10-21 |
| AR076328A1 (es) | 2011-06-01 |
| EP2419419A1 (en) | 2012-02-22 |
| US20100267689A1 (en) | 2010-10-21 |
| MX2011010964A (es) | 2011-11-02 |
| EP2419419B1 (en) | 2014-12-03 |
| KR20120006544A (ko) | 2012-01-18 |
| TW201102377A (en) | 2011-01-16 |
| US8513229B2 (en) | 2013-08-20 |
| ES2528625T3 (es) | 2015-02-11 |
| CN102459227A (zh) | 2012-05-16 |
| JP2012524111A (ja) | 2012-10-11 |
| JP5675773B2 (ja) | 2015-02-25 |
| NZ595432A (en) | 2013-12-20 |
| BRPI1016189A2 (pt) | 2016-04-19 |
| AU2010236346A1 (en) | 2011-11-03 |
| CN102459227B (zh) | 2014-08-20 |
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