HRP20161116T1 - NOVI DERIVATI CIKLOHEKSILAMINA KOJI DJELUJU KAO AGONISTI β2 ADRENERGIČKOG RECEPTORA I ANTAGONISTI MUSKARINSKOG ACETILKOLINSKOG RECEPTORA M3 - Google Patents
NOVI DERIVATI CIKLOHEKSILAMINA KOJI DJELUJU KAO AGONISTI β2 ADRENERGIČKOG RECEPTORA I ANTAGONISTI MUSKARINSKOG ACETILKOLINSKOG RECEPTORA M3 Download PDFInfo
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- HRP20161116T1 HRP20161116T1 HRP20161116TT HRP20161116T HRP20161116T1 HR P20161116 T1 HRP20161116 T1 HR P20161116T1 HR P20161116T T HRP20161116T T HR P20161116TT HR P20161116 T HRP20161116 T HR P20161116T HR P20161116 T1 HRP20161116 T1 HR P20161116T1
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- Croatia
- Prior art keywords
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- hydroxy
- methyl
- amino
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- 239000000048 adrenergic agonist Substances 0.000 title claims 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title 1
- 150000003946 cyclohexylamines Chemical class 0.000 title 1
- 230000000694 effects Effects 0.000 title 1
- 239000003149 muscarinic antagonist Substances 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 28
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- 125000005842 heteroatom Chemical group 0.000 claims 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 12
- -1 cyclohexyl hydroxy (di-2-thienyl)acetate dihydrofluoride Chemical compound 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- BRWJBQIGGNWUBO-IUEKTVKYSA-N O([C@H]1CC[C@@H](CC1)N(CCCN1C(OC2=CC(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound O([C@H]1CC[C@@H](CC1)N(CCCN1C(OC2=CC(CCNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 BRWJBQIGGNWUBO-IUEKTVKYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 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 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
- XOFMKTIZCDSXFR-UHFFFAOYSA-N 2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(C(=O)O)C1=CC=CS1 XOFMKTIZCDSXFR-UHFFFAOYSA-N 0.000 claims 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
- 229940121683 Acetylcholine receptor antagonist Drugs 0.000 claims 1
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 claims 1
- PRDDKBFOOBPSGA-IQHSNSCSSA-N C1([C@@H](O)CNCC=2C=C3C=CN(C3=CC=2)CCCN(C)[C@@H]2CC[C@H](CC2)OC(=O)C(O)(CC=2C=CC=CC=2)C=2SC=CC=2)=CC=C(O)C(NC=O)=C1 Chemical compound C1([C@@H](O)CNCC=2C=C3C=CN(C3=CC=2)CCCN(C)[C@@H]2CC[C@H](CC2)OC(=O)C(O)(CC=2C=CC=CC=2)C=2SC=CC=2)=CC=C(O)C(NC=O)=C1 PRDDKBFOOBPSGA-IQHSNSCSSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- QNRULQUMRQCKKD-MJKINOKDSA-N CC1(C(O)=O)C(C([C@H](CC2)CC[C@@H]2N(C)CCCN(C2=CC=C(CNC[C@@H](C(C(C=C3)=C4NC3=O)=CC=C4O)O)C=C2O2)C2=O)=CC=C2)=C2OC2=CC=CC=C12 Chemical compound CC1(C(O)=O)C(C([C@H](CC2)CC[C@@H]2N(C)CCCN(C2=CC=C(CNC[C@@H](C(C(C=C3)=C4NC3=O)=CC=C4O)O)C=C2O2)C2=O)=CC=C2)=C2OC2=CC=CC=C12 QNRULQUMRQCKKD-MJKINOKDSA-N 0.000 claims 1
- QFXZBDKZKZZXDD-HPSLPFNASA-N CN(CCCC1=NC(C2=CC=C(CNC[C@@H](C(C=C3)=C(C=CC(N4)=O)C4=C3O)O)C=C2)=NO1)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 Chemical compound CN(CCCC1=NC(C2=CC=C(CNC[C@@H](C(C=C3)=C(C=CC(N4)=O)C4=C3O)O)C=C2)=NO1)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 QFXZBDKZKZZXDD-HPSLPFNASA-N 0.000 claims 1
- FJQFIKJQGWOKFR-IUEKTVKYSA-N CN(CCCCN(C1=CC=C(CNC[C@@H](C(C(C=C2)=C3NC2=O)=CC=C3O)O)C=C1O1)C1=O)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 Chemical compound CN(CCCCN(C1=CC=C(CNC[C@@H](C(C(C=C2)=C3NC2=O)=CC=C3O)O)C=C1O1)C1=O)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 FJQFIKJQGWOKFR-IUEKTVKYSA-N 0.000 claims 1
- LDZUYQLPZKDMSJ-SECNDIFOSA-N CN(CCCN1C(C=CC(CNC[C@@H](C(C=C2)=C(C=CC(N3)=O)C3=C2O)O)=C2)=C2N=C1)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 Chemical compound CN(CCCN1C(C=CC(CNC[C@@H](C(C=C2)=C(C=CC(N3)=O)C3=C2O)O)=C2)=C2N=C1)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 LDZUYQLPZKDMSJ-SECNDIFOSA-N 0.000 claims 1
- IPYNABQGQLVYAI-DRVYDUGISA-N CN(CCCN1N=CC2=CC(CNC[C@@H](C(C(C=C3)=C4NC3=O)=CC=C4O)O)=CC=C12)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 Chemical compound CN(CCCN1N=CC2=CC(CNC[C@@H](C(C(C=C3)=C4NC3=O)=CC=C4O)O)=CC=C12)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 IPYNABQGQLVYAI-DRVYDUGISA-N 0.000 claims 1
- 208000020446 Cardiac disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- DFXBODPZJFVBHK-BCIIBWNXSA-N F.F.CN(CCCn1ccc2cc(CNC[C@H](O)c3ccc(O)c4[nH]c(=O)ccc34)ccc12)[C@H]1CC[C@@H](CC1)OOC(=O)C(c1cccs1)c1cccs1 Chemical compound F.F.CN(CCCn1ccc2cc(CNC[C@H](O)c3ccc(O)c4[nH]c(=O)ccc34)ccc12)[C@H]1CC[C@@H](CC1)OOC(=O)C(c1cccs1)c1cccs1 DFXBODPZJFVBHK-BCIIBWNXSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- OPRQRGHVAAWHMO-LNFMTQTQSA-N O([C@H]1CC[C@@H](CC1)N(CCCN1C(OC2=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound O([C@H]1CC[C@@H](CC1)N(CCCN1C(OC2=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 OPRQRGHVAAWHMO-LNFMTQTQSA-N 0.000 claims 1
- XJHGFZGUOALOCT-LNFMTQTQSA-N O([C@H]1CC[C@@H](CC1)N(CCCN1C(SC2=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound O([C@H]1CC[C@@H](CC1)N(CCCN1C(SC2=CC(CNC[C@H](O)C=3C=4C=CC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 XJHGFZGUOALOCT-LNFMTQTQSA-N 0.000 claims 1
- IXSRYCOADDLCDH-QEMZJVQQSA-N O([C@H]1CC[C@@H](CC1)N(CCCN1C(SC2=CC(CNC[C@H](O)C=3C=4OCC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound O([C@H]1CC[C@@H](CC1)N(CCCN1C(SC2=CC(CNC[C@H](O)C=3C=4OCC(=O)NC=4C(O)=CC=3)=CC=C21)=O)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 IXSRYCOADDLCDH-QEMZJVQQSA-N 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
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- FFVJAVUSCJCRPT-UHFFFAOYSA-N thiophen-2-yl acetate Chemical compound CC(=O)OC1=CC=CS1 FFVJAVUSCJCRPT-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
-
- A—HUMAN NECESSITIES
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Claims (15)
1. Spoj formule (I) ili njegove farmaceutski prihvatljive soli ili N-oksidi ili solvati ili deuterirani derivati:
[image]
naznačen time, što
• B predstavlja grupu formule (IB):
[image]
naznačen time, što
o R7 je odabran iz grupe koja se sastoji od atoma vodika, linearne ili razgranate C1-4 alkilne grupe i linearne ili razgranate C1-4 alkoksi grupe,
o Ar je odabran iz grupe koja se sastoji od C3-10 zasićene ili nezasićene, monocikličke ili bicikličke cikloalkilne grupe, C5-C10 monocikličke ili bicikličke arilne grupe, zasićene ili nezasićene monocikličke ili bicikličke heterociklilne grupe od 3 do 14 članova s jednim ili više heteroatoma odabranih iz N, S i O, monocikličke ili bicikličke heteroarilne grupe od 5 do 14 članova s jednim ili više heteroatoma odabranih iz N, S i O, pri čemu su cikličke grupe opcijski zasebno supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, cijano grupe, nitro grupe, okso grupe, karboksi grupe, C1-4 alkilne grupe, C1-4 alkoksi grupe, -CF3, –OCF3, -NReRf, -(CH2)p-OH, -NRe(CO)Rf, -NRe-SO2-Rg, -SO2-NReRf, -OC(O)Rh i NRe(CH2)(0-2)-Ri, pri čemu p ima vrijednost 0, 1 ili 2 i pri čemu:
o Re i Rf zasebno predstavljaju atom vodika ili linearnu ili razgranatu C1-4 alkilnu grupu,
o Rg je odabran iz grupe koja se sastoji od linearne ili razgranate C1-4 alkilne grupe, C6-5 arilne grupe, zasićene ili nezasićene C3-8 cikloalkilne grupe, pri čemu su ciklične grupe zasebno opcijski supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, C1-4 alkilne grupe i C1-4 alkoksi grupe.
o Rh je odabran iz atoma vodika, -NReRf i C5-6 arilne grupe koja je opcijski supstituirana s jednim ili više supstituenata odabranih iz C1-4 alkilne grupe i C1-4 alkoksi grupe,
o Ri je odabran iz grupe koja se sastoji od C5-6 arilne grupe, C3-8 cikloalkilne grupe i zasićene ili nezasićene heterociklilne grupe s 3 do 8 članova, pri čemu su te grupe zasebno opcijski supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, C1-4 alkilne grupe i C1-4 alkoksi grupe,
• R1 i R2 zasebno su odabrani iz grupe koja se sastoji od atoma vodika i linearne ili razgranate C1-4 alkilne grupe,
• R3 predstavlja grupu formule:
[image]
naznačenu time, što
o R4 predstavlja atom vodika, hidroksi grupu, hidroksimetilnu grupu ili linearnu ili razgranatu C1-4 alkilnu grupu,
o R5 predstavlja zasićenu ili nezasićenu C3-8 cikloalkilnu grupu, C5-6 arilnu grupu, heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O; (C1-4 alkilnu)-(C5-6 arilnu) grupu, (C1-4 alkilnu)-(C3-8 cikloalkilnu) grupu ili (C1-4 alkilnu)-(heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O) grupu, pri čemu su te grupe zasebno opcijski supstituirane s jednim ili više supstituenata Ra,
o R6 predstavlja C5-6 arilnu grupu, heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O, zasićenu ili nezasićenu C3-8 cikloalkilnu grupu, C1-8 alkilnu grupu, C2-8 alkenilnu grupu, C2-8 alkinilnu grupu, (C1-4 alkilnu)-(C5-6 arilnu) grupu, (C1-4 alkilnu)-(C3-8 cikloalkilnu) grupu ili (C1-4 alkilnu)-(heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O) grupu, pri čemu su te grupe zasebno opcijski supstituirane s jednim ili više supstituenata Rb,
o Ra i Rb zasebno predstavljaju atom halogena, hidroksi grupu, C1-4 alkilnu grupu, C1-4 alkoksi grupu, -SH, C1-4 alkiltio grupu, nitro grupu, cijano grupu, -CO2R', -NR'R'', -C(O)NR'R'', -N(R''')C(O)-R', -N(R''')-C(O)NR'R'', pri čemu R', R'' i R''' svaki zasebno predstavljaju atom vodika, ili C1-4 alkilnu grupu ili R' i R'' zajedno s atomom dušika za koji su vezani formiraju heterociklički prsten od 3 do 6 članova.
o Q predstavlja direktnu vezu, –CH2-, -CH2-CH2-, -O-, -O-CH2-, -S-, -S-CH2- ili –CH=CH-,
o predstavlja točku vezivanja R3 na ostatak molekule iz formule (I),
• A1 i A2 zasebno su odabrani iz grupe koja se sastoji od C1-10 alkilenske grupe, C2-10 alkenilenske grupe i C2-10 alkinilenske grupe, pri čemu su spomenute grupe opcijski supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, hidroksi grupe, linearne ili razgranate C1-4 alkilne grupe, linearne ili razgranate C1-4 alkoksi grupe, C5-6 arilne grupe i C3-7 cikloalkilne grupe,
• L1 je odabran iz direktne veze, -O-, NRc-, -S-, -S(O)-, -SO2-, -NRc(CO)-, -(CO)NRc-, –NRc(CO)(CH2)qO-, -O(CH2)q(CO)NRc-, –NRc(CH2)qO-, –O(CH2)qNRc-, –NRc(CO)NRd-, -C(O)-, -C(O)O-, -OC(O)-, -S(O)2NRc-, -NRcS(O)2-, -NRcS(O)2NRd-, –C(O)NRcS(O)2- i –S(O)2NRcC(O)-, pri čemu su Rc i Rd zasebno odabrani iz atoma vodika i linearne ili razgranate C1-4 alkilne grupe, a q ima vrijednost 0, 1 ili 2,
• G je odabran iz grupe koja se sastoji od C3-10 monocikličke ili bicikličke cikloalkilne grupe, C5-C14 monocikličke ili bicikličke arilne grupe, zasićene ili nezasićene monocikličke ili bicikličke heterociklilne grupe od 3 do 14 članova s jednim ili više heteroatoma odabranih iz N, S i O, monocikličke ili bicikličke heteroarilne grupe od 5 do 14 članova s jednim ili više heteroatoma odabranih iz N, S i O te bicikličkog prstenastog sustava koji se sastoji od dva monociklička prstenasta sustava međusobno povezana kovalentnom vezom, pri čemu su spomenuti monociklički prstenasti sustavi zasebno odabrani iz C3-8 cikloalkilne grupe, C5-C6 arilne grupe, zasićene ili nezasićene heterocikličke grupe od 3 do 8 članova s jednim ili više heteroatoma odabranih iz N, S i O te heterocikličke grupe od 5 do 6 članova s jednim ili više heteroatoma odabranih iz N, S i O,
pri čemu su cikličke grupe zasebno opcijski supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, C1-4 alkilne grupe, C1-4alkoksi grupe, karboksi grupe, cijano grupe, nitro grupe, hidroksi grupe, okso grupe, trifluoreometilne grupe i trifluorometoksi grupe,
pod uvjetom da je G fenilna grupa, da L1 nije jedna od grupa odabranih iz direktne veze, -O-, -NHC(O)-, -C(O)NH- i -NH(CO)O- grupe.
2. Spoj prema zahtjevu 1, naznačen time, što:
a) G je odabran iz grupe koja se sastoji od C5-C6 arilne grupe, zasićene ili nezasićene bicikličke heterociklilne grupe od 8 do 10 članova s jednim ili više heteroatoma odabranih iz N, S i O, bicikličke heteroarilne grupe od 8 do 10 članova s jednim ili više heteroatoma odabranih iz N, S i O te C5-C6 arilne grupe povezane s prstenastim sustavom odabranim iz C5-6 arilne grupe, C3-7 cikloalkilne grupe i heteroarilne grupe od 5 do 6 članova s dva ili tri heteroatoma odabrana iz N, S i O, pri čemu su cikličke grupe zasebno opcijski supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, C1-4 alkilne grupe, C1-4 alkoksi grupe, cijano grupe, nitro grupe, hidroksi grupe i okso grupe, poželjno je G odabran iz fenilne grupe, nezasićene bicikličke heterociklilne grupe od 9 do 10 članova s jednim ili više heteroatoma odabranih iz N, S i O, bicikličke heteroarilne grupe od 9 do 10 članova s jednim ili više heteroatoma odabranih iz N, S i O te C5-C6 arilne grupe povezane s prstenastim sustavom odabranim iz C5-6 arilne grupe i heteroarilne grupe od 5 do 6 članova s dva ili tri heteroatoma odabrana iz N, S i O, pri čemu su cikličke grupe zasebno opcijski supstituirane s jednim ili više supstituenata odabranih iz atoma halogena, metilne grupe, metoksi grupe, cijano grupe, hidroksi grupe i okso grupe; i/ili
b) L1 je odabran iz grupe koja se sastoji od direktne veze, -NRc-, -S-, -SO2-, -C(O)-, -C(O)O-, -S(O)2NRc-, -NRcS(O)2-, –NRc(CO)(CH2)O-, –O(CH2)(CO)NRc-, -NRc(CO)NRd- i -CONRcS(O)2-, pri čemu su Rc i Rd zasebno odabrani iz atoma vodika i metilne grupe, poželjno je L1 odabran iz direktne veze, -NH-, -S-, -SO2-, -C(O)-, -NRc(CO)NRd- i –O(CH2)(CO)NRc- grupe.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, naznačen time, što -G-L1- ima sljedeću formulu:
[image]
naznačenu time, što
- V, W, i Z su zasebno odabrani iz –N-, -C-, -S-, -O- i –C(O)-
- Lx predstavlja heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O ili Lx predstavlja –O-CH2-CO-NRc-, pri čemu Rc predstavlja atom vodika ili metilnu grupu.
- predstavlja točku vezivanja s A2 i
- ● predstavlja točku vezivanja s A1.
4. Spoj prema bilo kojem zahtjevu od 1 do 3, sa sljedećom formulom (IA):
[image]
naznačen time, što su R1, R2, R3, A1, A2, V, W i B kako je definirano u bilo kojem zahtjevu od 1 do 3.
5. Spoj prema bilo kojem zahtjevu od 1 do 4, naznačen time, što A1 i A2 zasebno predstavljaju C1-6 alkilensku grupu opcijski supstituiranu s jednim ili više supstituenata odabranih iz C1-2 alkilne grupe, C1-2 alkoksi grupe i fenilne grupe, poželjno supstituiranu s jednim ili dva supstituenta odabrana iz metilne grupe i metoksi grupe, poželjnije iz metilne grupe.
6. Spoj prema zahtjevu 1, naznačen time, što Ar predstavlja grupu formule
[image]
naznačenu time, što
• Ga i Gb su zasebno odabrani iz atoma dušika i atoma ugljika,
• r ima vrijednost 0, 1, 2 ili 3 i
• R je odabran iz grupe koja se sastoji od atoma halogena, amino grupe, cijano grupe, nitro grupe, okso grupe, karboksi grupe, C1-4 alkilne grupe, C1-4 alkoksi grupe, -CF3, –OCF3, -(CH2)p-OH, -NH(CO)H, -NH-SO2-Rg, -SO2NH2, -OC(O)H, –O(CO)-(4-metil)fenil, –O(CO)-N(CH3)2, -OC(O)NH2 i –NH(CH2)(1-2)-Ri grupe, pri čemu je p kako je definirano u zahtjevu 1, a Rg i Ri su zasebno odabrani iz fenilne grupe opcijski supstituirane supstituentom odabranim iz metilne grupe ili metoksi grupe.
• Rj predstavlja atom halogena,
• T je odabran iz grupe koja se sastoji od –CH2- i –NH-,
• X i Y svaki predstavljaju atom vodika ili X zajedno s Y formira grupu –CH2-CH2-, -CH=CH-, -CH2-O- ili -S-, pri čemu je u slučaju -CH2-O- metilenska grupa vezana za karbonilnu grupu koja drži X, a atom kisika je vezan za atom ugljika u fenilnom prstenu koji drži Y.
7. Spoj prema bilo kojem zahtjevu od 1 do 6, sa sljedećom formulom (IC):
[image]
naznačenom time, što
• R3 predstavlja grupu formule:
[image]
naznačenu time, što
o R4 predstavlja atom vodika, hidroksi grupu, hidroksimetilnu grupu ili linearnu ili razgranatu C1-4 alkilnu grupu,
o R5 i R6 zasebno predstavljaju C5-6 arilnu grupu, heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O; (C1-4 alkilnu)-(C5-6 arilnu) grupu ili C3-8 cikloalkilnu grupu,
o Q predstavlja direktnu vezu ili –CH2-, -CH2-CH2-, -O-, -O-CH2-, -S-, -S-CH2- ili –CH=CH-,
o predstavlja točku vezivanja R3 na ostatak molekule iz formule (I),
• X i Y svaki predstavljaju atom vodika ili Y zajedno s Y formira grupu –CH2-CH2-, -CH=CH-, -CH2-O- ili -S-, pri čemu je u slučaju -CH2-O- metilenska grupa vezana za atom ugljika u amido supstituentu koji drži X, a atom kisika je vezan za atom ugljika u fenilnom prstenu koji drži Y
• n ima vrijednost 0, 1 ili 2,
• m ima vrijednost 2, 3 ili 4,
• R8, R9 i R10 zasebno predstavljaju atom vodika ili linearnu ili razgranatu C1-4 alkilnu grupu,
• -G-L1 predstavlja grupu formule:
[image]
naznačenu time, što
- V, W, i Z su zasebno odabrani iz –N-, -C-, -S-, -O- i –C(O)-,
- Lx predstavlja heteroarilnu grupu od 5 do 6 članova s najmanje jednim heteroatomom odabranim iz N, S i O ili Lx predstavlja –O-CH2-CO-NRd-, pri čemu Rd predstavlja atom vodika ili metilnu grupu.
- predstavlja točku vezivanja s grupom koja sadrži cikloheksilnu grupu i
- ● predstavlja točku vezivanja s grupom koja sadrži aminoetilfenolnu grupu.
8. Spoj prema zahtjevu 7, naznačen time, što ima sljedeću formulu (ID):
[image]
naznačenu time, što
• R3 predstavlja grupu formule:
[image]
naznačenu time, što
o R4 predstavlja atom vodika, hidroksi grupu, hidroksimetilnu grupu ili linearnu ili razgranatu C1-4 alkilnu grupu,
o R5 i R6 zasebno predstavljaju tienilnu grupu, fenilnu grupu, benzilnu grupu ili C4-6 cikloalkilnu grupu,
o Q predstavlja direktnu vezu ili atom kisika,
o predstavlja točku vezivanja R3 na ostatak molekule iz formule (I).
9. Spoj prema zahtjevu 8, naznače time, što:
• X zajedno s Y formira grupu –CH=CH-;
• V i W oba predstavljaju atom azota;
• n ima vrijednost 0;
• m ima vrijednost 3;
• R10 predstavlja metilnu grupu;
• R8 i R9 oba predstavljaju atom vodika;
• R3 predstavlja grupu formule i);
• R4 predstavlja hidroksilnu grupu; i
• R5 i R6 oba su tienilne grupe.
10. Spoj prema zahtjevu 7, naznačen time, što -G-L1 predstavlja grupu formule:
[image]
naznačenu time, što
o V je odabran iz -N-, -C-, -S- i -O-,
o W je odabran iz -N-, -C- i –C(O),
o Lx predstavlja oksadiazolilnu grupu ili –O-CH2-CO-NRc-, pri čemu Rc predstavlja atom vodika ili metilnu grupu.
o predstavlja točku vezivanja grupom koja sadrži cikloheksilnu grupu i
o ● predstavlja točku vezivanja s grupom koja sadrži aminoetilfenolni fragment,
- R8 i R9 su zasebno odabrani iz atoma vodika i metilne grupe,
- R10 predstavlja metilnu grupu,
- n ima vrijednost 0 ili 1,
- m ima vrijednost 2, 3 ili 4,
- X i Y oba predstavljaju atom vodika ili X zajedno s Y formira –CH=CH-, -CH2-O- ili -S- grupu,
- R3 predstavlja grupu formule:
[image]
naznačenu time, što
o R4 predstavlja metilnu grupu ili hidroksi grupu,
o R5 i R6 zasebno predstavljaju tienilnu grupu, fenilnu grupu, benzilnu grupu ili ciklopentilnu grupu,
o Q predstavlja direktnu vezu ili atom kisika,
o predstavlja točku vezivanja R3 na ostatak molekule iz formule (I).
11. Spoj prema zahtjevu 1, koji je jedno od sljedećih
Trans-4-[{3-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-2-okso-1,3-benzoksazol-3(2H)-il]propil}(metil)amino]-cikloheksil hidroksi(di-2-tienil)acetat, dihidrofluorid,
trans-4[{3-[5-({(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-2-okso-2,3-dihidro-1H-benzimidazol-1-il]propil}(metil)amino]cikloheksil hidroksi (di-2-tienil)acetat dihidrofluorid,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-1H-1,2,3-benzotiazol-1-il]propil}(metil)amino]cikloheksilhidroksi(di-2-tienil)acetat dihidrofluorid,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-1H-indol-1-il]propil}(metil)amino]cikloheksilhidroksi (di-2-tienil)acetat dihidrofluorid,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-1H-benzimidazol-1-il]propil}(metil)amino]cikloheksilhidroksi(di-2-tienil)acetat,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-1H-indazol-1-il]propil}(metil)amino]cikloheksilhidroksi(di-2-tienil)acetat,
Trans-4-[{3-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-2-okso-1,3-benzotiazol-3(2H)-il]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[{3-[5-({[(2R)-2-[3-(formilamino)-4-hidroksifenil]-2-hidroksietil}amino)metil]-1H-1,2,3-benzotriazol-1-il}propil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(4-hidroksi-2-okso-2,3-dihidro-1,3-benzotiazol-7-il)etil]amino}metil)-1H-1,2,3-benzotiazol-1-il]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[{3-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}etil)-2-okso-1,3-benzoksazol-3(2H)-il]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[{3-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}etil)-2-okso-1,3-benzoksazol-3(2H)-il]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[{2-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-2-okso-1,3-benzoksazol-3(2H)-il]etil](metil)amino]cikloheksilhidroksi(di-2-tienil)acetat,
Trans-4-[{4-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-2-okso-1,3-benzoksazol-3(2H)-il]butil}(metil)amino]cikloheksilhidroksi(di-2-tienil)acetat,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-1H-1,2,3-benzotiazol-1-il]propil}(metil)amino]cikloheksilciklopentil(hidroksi)2-tienilacetat,
Trans-4-[{3-[6-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-2-okso-1,3-benzoksazol-3(2H)il]propil}(metil)amino]cikloheksil-9-metil-9H-ksanten-9-karboksilat,
Trans-4-[{3-[6-({[(2R)-2-hidroksi-2-(5-hidroksi-3-okso-3,4-dihidro-2H-1,4-benzoksazin-8il)etil]amino}metil)-2-okso-1,3-benzotiazol-3(2H)-il]propil}(metil)amono]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[(2-{5-[({(2R)-2-[3-(formilamino)-4-hidroksifenil]-2-hidroksietil}amino)metil]-1H-indol-1-il}etil)(metil)amono]cikloheksil 9H-fluoren-9-karboksilat,
Trans-4-[(3-{5-[({(2R)-2-[3-(formilamino)-4-hidroksifenil]-2-hidroksietil}amino)metil]-1H-indol-1-il}propil)(metil)amino]cikloheksil 2-hidroksi-3-fenil-2-(2-tienil)propanoat,
Trans-4-[{3-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}-2-metilpropil)-2-okso-2,3-dihidro-1H-benzimidazol-1-il]propil}(metil)amino]cikloheksil 2,2-difenilpropanoat,
Trans-4-[{2-[5-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}-2-metilpropil)-1H-indazol-1-il}etil}(metil)amino]cikloheksil 2-fenil-2-(2-tienil)propanoat,
Trans-4-[{3-[6-(2--[{(2R)-2-hidroksi-2-(8-hidroksi-2-metilen-1,2-dihidrokvinolin-5-il)etil]amino}propil)-2-okso-1,3-benzoksazol-3(2H)-il]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
Trans-4-[(3-{3-[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)fenil]-1,2,4-oksadiazol-5-il}propil)(metil)amino]cikloheksilhidroksi(di-2-tienil)acetat,
Trans-4-[{2-[{[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)fenoksi]acetil}(metil)amino]etil}(metil)amino]cikloheksil hidroksi(di-2-tienil-acetat,
Trans-4-[{2-[{[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)fenoksi]acetil}amino)etil](metil)amino]cikoheksil hidroksi(di-2-tienil)acetat,
Trans-4-[(3-{3-[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-5-metoksifenil]1,2,4-oksadiazol-5-il}propil(metil)amono]cikloheksil hidroksi(di-3-tienil)acetat, i
Trans-4-[{2-[{[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-5-metoksifenoksi]acetil}(metil)amino]etil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,
ili njihove farmaceutski prihvatljive soli ili N-oksidi ili solvati ili deuterirani derivati.
12. Spoj prema bilo kojem zahtjevu od 1 do 11 za primjenu u liječenju čovjeka ili životinje putem terapije.
13. Spoj prema bilo kojem zahtjevu od 1 do 11 za primjenu u liječenju patološkog stanja ili bolesti povezane s djelovanjem agonista β2 adrenergičkog receptora i antagonista muskarinskog acetilkolinskog receptora M3, pri čemu je stanje ili bolest poželjno odabrano iz plućnih bolesti, prijevremenog poroda, glaukoma, neuroloških poremećaja, srčanih poremećaja, upalnih ili gastrointestinalnih poremećaja, a poželjnije je astma ili kronična opstruktivna plućna bolest.
14. Farmaceutski pripravak koji sadrži spoj definiran u bilo kojem zahtjevu od 1 do 11 u kombinaciji s farmaceutski prihvatljivim otapalom ili nosačem.
15. Kombinirani proizvod koji sadrži (i) spoj prema bilo kojem zahtjevu od 1 do 11; i (ii) drugi spoj odabran iz kortikosteroida i inhibitora PDE4, za istovremenu, odvojenu ili sekvencijalnu primjenu u liječenju čovjeka ili životinje.
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PCT/EP2012/072309 WO2013068552A1 (en) | 2011-11-11 | 2012-11-09 | NEW CYCLOHEXYLAMINE DERIVATIVES HAVING β2 ADRENERGIC AGONIST AND M3 MUSCARINIC ANTAGONIST ACTIVITIES |
EP12781362.4A EP2776425B1 (en) | 2011-11-11 | 2012-11-09 | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
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