JP2013526494A5 - - Google Patents
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- JP2013526494A5 JP2013526494A5 JP2013509473A JP2013509473A JP2013526494A5 JP 2013526494 A5 JP2013526494 A5 JP 2013526494A5 JP 2013509473 A JP2013509473 A JP 2013509473A JP 2013509473 A JP2013509473 A JP 2013509473A JP 2013526494 A5 JP2013526494 A5 JP 2013526494A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- amino
- methyl
- group
- ethyl
- 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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- -1 8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl Chemical group 0.000 claims description 71
- GUTQMBQKTSGBPQ-UHFFFAOYSA-N dithiophen-2-ylmethanone Chemical group C=1C=CSC=1C(=O)C1=CC=CS1 GUTQMBQKTSGBPQ-UHFFFAOYSA-N 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- WIUHYQBOXHNHLG-UHFFFAOYSA-N acetic acid hydrofluoride Chemical compound F.C(C)(=O)O WIUHYQBOXHNHLG-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 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 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- MFDRXDAELXCWCB-OXVIYWBMSA-N [4-[9-[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]nonyl-methylamino]cyclohexyl] 2-hydroxy-2,2-dithiophen-2-ylacetate Chemical compound C([C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)NCCCCCCCCCN(C)C(CC1)CCC1OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 MFDRXDAELXCWCB-OXVIYWBMSA-N 0.000 claims description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 2
- RWWDBINLIXRDCK-UHFFFAOYSA-N cyclohexyl 9-methylxanthene-9-carboxylate Chemical compound C1(CCCCC1)OC(=O)C1(C2=CC=CC=C2OC=2C=CC=CC1=2)C RWWDBINLIXRDCK-UHFFFAOYSA-N 0.000 claims description 2
- 229940049953 phenylacetate Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 claims 1
- 239000013066 combination product Substances 0.000 claims 1
- 229940127555 combination product Drugs 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000001079 digestive effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000003149 muscarinic antagonist Substances 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QRMKTNANRJCRCY-UHFFFAOYSA-N ethylammonium acetate Chemical compound CC[NH3+].CC([O-])=O QRMKTNANRJCRCY-UHFFFAOYSA-N 0.000 description 1
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10382118.7 | 2010-05-13 | ||
| EP10382118A EP2386555A1 (en) | 2010-05-13 | 2010-05-13 | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| US36504510P | 2010-07-16 | 2010-07-16 | |
| US61/365,045 | 2010-07-16 | ||
| PCT/EP2011/002376 WO2011141180A1 (en) | 2010-05-13 | 2011-05-13 | NEW CYCLOHEXYLAMINE DERIVATIVES HAVING β2 ADRENERGIC AGONIST AND M3 MUSCARINIC ANTAGONIST ACTIVITIES |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013526494A JP2013526494A (ja) | 2013-06-24 |
| JP2013526494A5 true JP2013526494A5 (https=) | 2013-11-14 |
| JP5851489B2 JP5851489B2 (ja) | 2016-02-03 |
Family
ID=42646365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013509473A Expired - Fee Related JP5851489B2 (ja) | 2010-05-13 | 2011-05-13 | β２アドレナリンアゴニスト活性およびＭ３ムスカリンアンタゴニスト活性を有する新規シクロヘキシルアミン誘導体 |
Country Status (38)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| ITRM20110083U1 (it) | 2010-05-13 | 2011-11-14 | De La Cruz Jose Antonio Freire | Piastra per la costruzione di carrelli per aeroplani |
| EP2592077A1 (en) * | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2592078A1 (en) * | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2925336B1 (en) | 2012-11-30 | 2022-10-12 | Harmonic Pharma | Natural compounds for use in the treatment of beta-2 adrenergic receptor related diseases |
| MA38260B1 (fr) | 2012-12-18 | 2018-04-30 | Almirall Sa | Nouveaux dérivés de cyclohexyl et quinuclidinyl carbamate ayant une activité d'agoniste adrénergique beta2 et une activité d'antagoniste muscarinique m3 |
| TWI643853B (zh) * | 2013-02-27 | 2018-12-11 | 阿爾米雷爾有限公司 | 同時具有β2腎上腺素受體促效劑和M3毒蕈鹼受體拮抗劑活性之2-氨基-1-羥乙基-8-羥基喹啉-2(1H)-酮衍生物之鹽類 |
| TW201440768A (zh) * | 2013-02-27 | 2014-11-01 | Almirall Sa | 雙毒蕈鹼拮抗劑-β2腎上腺素促效劑複合物及皮質類固醇之組合物 |
| TW201517906A (zh) | 2013-07-25 | 2015-05-16 | Almirall Sa | 含有ｍａｂａ化合物和皮質類固醇之組合 |
| TWI641373B (zh) | 2013-07-25 | 2018-11-21 | 阿爾米雷爾有限公司 | 具有蕈毒鹼受體拮抗劑和β２腎上腺素受體促效劑二者之活性的２－胺基－１－羥乙基－８－羥基喹啉－２（１Ｈ）－酮衍生物之鹽 |
| US9133185B2 (en) | 2013-12-05 | 2015-09-15 | Chiesi Farmaceutici S.P.A | Heteroaryl derivatives |
| RU2016121852A (ru) * | 2013-12-05 | 2017-12-07 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Производные бензгидрила для лечения респираторных заболеваний |
| EP3139924A4 (en) * | 2014-05-06 | 2018-03-07 | Anthony G. Visco | Methods of treating or preventing preterm labor |
| US11175268B2 (en) | 2014-06-09 | 2021-11-16 | Biometry Inc. | Mini point of care gas chromatographic test strip and method to measure analytes |
| CN106537128B (zh) | 2014-06-09 | 2021-06-18 | 生物统计股份有限公司 | 用于测量分析物的低成本测试条和方法 |
| TW201617343A (zh) * | 2014-09-26 | 2016-05-16 | 阿爾米雷爾有限公司 | 具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物 |
| TWI703138B (zh) * | 2015-02-12 | 2020-09-01 | 義大利商吉斯藥品公司 | 具有蕈毒鹼受體拮抗劑及β２腎上腺素受體促效劑活性之化合物 |
| CN114859028A (zh) | 2016-07-19 | 2022-08-05 | 生物统计股份有限公司 | 使用批量可校准测试条测量分析物的方法和系统 |
| WO2020244452A1 (zh) * | 2019-06-06 | 2020-12-10 | 中国医药研究开发中心有限公司 | 具有β 2受体激动及M受体拮抗活性的杂环衍生物及其医药用途 |
| WO2022172296A1 (en) * | 2021-02-12 | 2022-08-18 | Gbr Laboratories Private Limited | A process for preparing navafenterol and intermediates thereof |
| WO2025245591A1 (en) * | 2024-05-31 | 2025-12-04 | Aché Laboratórios Farmacêuticos S.A. | Compounds, process for obtaining the compounds, intermediate compounds, reagent compounds, pharmaceutical compositions, pharmaceutical combinations, medicaments, uses and methods of treatment |
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