JP2016505582A5 - - Google Patents
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- JP2016505582A5 JP2016505582A5 JP2015548459A JP2015548459A JP2016505582A5 JP 2016505582 A5 JP2016505582 A5 JP 2016505582A5 JP 2015548459 A JP2015548459 A JP 2015548459A JP 2015548459 A JP2015548459 A JP 2015548459A JP 2016505582 A5 JP2016505582 A5 JP 2016505582A5
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- JP
- Japan
- Prior art keywords
- group
- hydroxy
- amino
- oxo
- methyl
- 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 3-bromoisoxazol-5-yl Chemical group 0.000 claims 85
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 33
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 125000002950 monocyclic group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002619 bicyclic group Chemical group 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 10
- 229920006395 saturated elastomer Polymers 0.000 claims 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 9
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 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 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000004419 alkynylene group Chemical group 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 150000001408 amides Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 claims 1
- WESNIBJUEFXARC-AQGBOPFGSA-N C(N)(OC1=C(C=CC(=C1)CCC(=O)N[C@@H]1CC[C@H](CC1)CNC[C@@H](C1=C2C=CC(NC2=C(C=C1)O)=O)O)C1=CC=CC=C1)=O Chemical compound C(N)(OC1=C(C=CC(=C1)CCC(=O)N[C@@H]1CC[C@H](CC1)CNC[C@@H](C1=C2C=CC(NC2=C(C=C1)O)=O)O)C1=CC=CC=C1)=O WESNIBJUEFXARC-AQGBOPFGSA-N 0.000 claims 1
- DKPOBCUZPDDHGX-PMERELPUSA-N C(N)(OC1=C(C=CC(=C1)CCCC(=O)NC1=C(C=C(C(=C1)OC)CNC[C@@H](C1=C2C=CC(NC2=C(C=C1)O)=O)O)Cl)C1=CC=CC=C1)=O Chemical compound C(N)(OC1=C(C=CC(=C1)CCCC(=O)NC1=C(C=C(C(=C1)OC)CNC[C@@H](C1=C2C=CC(NC2=C(C=C1)O)=O)O)Cl)C1=CC=CC=C1)=O DKPOBCUZPDDHGX-PMERELPUSA-N 0.000 claims 1
- 208000020446 Cardiac disease Diseases 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
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- GALAHBSBWJKUAV-LJAQVGFWSA-N [5-[3-[2-chloro-4-[[[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1H-quinolin-5-yl)ethyl]amino]methyl]-5-methoxyanilino]-3-oxopropyl]-2-phenylphenyl] carbamate Chemical compound C(N)(OC1=C(C=CC(=C1)CCC(=O)NC1=C(C=C(C(=C1)OC)CNC[C@@H](C1=C2C=CC(NC2=C(C=C1)O)=O)O)Cl)C1=CC=CC=C1)=O GALAHBSBWJKUAV-LJAQVGFWSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000001800 adrenalinergic effect Effects 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 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
- 230000027455 binding Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
- 230000001079 digestive effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000000034 method Methods 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12382513 | 2012-12-18 | ||
| EP12382513.5 | 2012-12-18 | ||
| US201361750959P | 2013-01-10 | 2013-01-10 | |
| US61/750,959 | 2013-01-10 | ||
| PCT/EP2013/076973 WO2014095920A1 (en) | 2012-12-18 | 2013-12-17 | New cyclohexyl and quinuclidinyl carbamate derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016505582A JP2016505582A (ja) | 2016-02-25 |
| JP2016505582A5 true JP2016505582A5 (cg-RX-API-DMAC7.html) | 2017-01-26 |
| JP6307091B2 JP6307091B2 (ja) | 2018-04-04 |
Family
ID=47458807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015548459A Expired - Fee Related JP6307091B2 (ja) | 2012-12-18 | 2013-12-17 | 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のシクロヘキシルおよびキヌクリジニルカルバメート誘導体 |
Country Status (27)
Families Citing this family (11)
| 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 |
| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| BR112015013628A2 (pt) | 2012-12-18 | 2017-07-11 | Almirall Sa | derivados de carbamato de ciclo-hexila e quinuclidinila tendo atividades agonista adrenérgica de beta2 e antagonista muscarínica de 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 |
| 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 |
| 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 |
| AU2015274801B2 (en) | 2014-06-09 | 2020-10-15 | Biometry Inc. | Low cost test strip and method to measure analyte |
| US11175268B2 (en) | 2014-06-09 | 2021-11-16 | Biometry Inc. | Mini point of care gas chromatographic test strip and method to measure analytes |
| 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 |
| EP4464772A3 (en) | 2016-07-19 | 2024-12-04 | Biometry Inc. | Methods of and systems for measuring analytes using batch calibratable test strips |
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