ME02675B - Novi derivati cikloheksilamina sa aktivnostima beta2 adrenergijskog agonista i m3 muscarinskog antagonista - Google Patents
Novi derivati cikloheksilamina sa aktivnostima beta2 adrenergijskog agonista i m3 muscarinskog antagonistaInfo
- Publication number
- ME02675B ME02675B MEP-2017-18A MEP1817A ME02675B ME 02675 B ME02675 B ME 02675B ME P1817 A MEP1817 A ME P1817A ME 02675 B ME02675 B ME 02675B
- Authority
- ME
- Montenegro
- Prior art keywords
- hydroxy
- amino
- methyl
- group
- ethyl
- Prior art date
Links
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 title 1
- 239000000556 agonist Substances 0.000 title 1
- 230000003042 antagnostic effect Effects 0.000 title 1
- 150000003946 cyclohexylamines Chemical class 0.000 title 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 32
- -1 cyclohexyl hydroxy(di-2-thienyl)acetate Chemical compound 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 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 3
- 235000019253 formic acid Nutrition 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 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
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- FVEJUHUCFCAYRP-UHFFFAOYSA-N 2-hydroxy-2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(O)(C(=O)O)C1=CC=CS1 FVEJUHUCFCAYRP-UHFFFAOYSA-N 0.000 claims 1
- WCRHWWWLTNWHQS-ABCZBHHISA-N C12=CC=CC=C2OC2=CC=CC=C2C1(C)C(=O)O[C@H](CC1)CC[C@@H]1N(C)CCCCCCCCCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1(C)C(=O)O[C@H](CC1)CC[C@@H]1N(C)CCCCCCCCCNC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 WCRHWWWLTNWHQS-ABCZBHHISA-N 0.000 claims 1
- RFHUGEAREMSBLP-WBXFWKJNSA-N CN(CCC(NC(C=C(C(CNC[C@@H](C(C(C=C1)=C2NC1=O)=CC=C2O)O)=C1)OC)=C1Cl)=O)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 Chemical compound CN(CCC(NC(C=C(C(CNC[C@@H](C(C(C=C1)=C2NC1=O)=CC=C2O)O)=C1)OC)=C1Cl)=O)[C@H](CC1)CC[C@@H]1OC(C(O)=O)(C1=CC=CS1)C1=CC=CS1 RFHUGEAREMSBLP-WBXFWKJNSA-N 0.000 claims 1
- AHZPWGGWOSEDTP-WBXFWKJNSA-N COc1cc(NC(=O)CCN(C)[C@H]2CC[C@@H](CC2)OC(=O)C(O)(c2cccs2)c2cccs2)c(Cl)cc1CNC[C@H](O)c1ccc(O)c2[nH]c(=O)ccc12 Chemical compound COc1cc(NC(=O)CCN(C)[C@H]2CC[C@@H](CC2)OC(=O)C(O)(c2cccs2)c2cccs2)c(Cl)cc1CNC[C@H](O)c1ccc(O)c2[nH]c(=O)ccc12 AHZPWGGWOSEDTP-WBXFWKJNSA-N 0.000 claims 1
- 208000020446 Cardiac disease Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- DEFIGYIWVLTMLO-GHAOVRLMSA-N F.CC(Cc1ccc(OCCCN(C)[C@H]2CC[C@@H](CC2)OC(=O)C(O)(c2cccs2)c2cccs2)cc1)NC[C@H](O)c1ccc(O)c2[nH]c(=O)ccc12 Chemical compound F.CC(Cc1ccc(OCCCN(C)[C@H]2CC[C@@H](CC2)OC(=O)C(O)(c2cccs2)c2cccs2)cc1)NC[C@H](O)c1ccc(O)c2[nH]c(=O)ccc12 DEFIGYIWVLTMLO-GHAOVRLMSA-N 0.000 claims 1
- LPRBLDKUDJHOFD-XFPMNCHFSA-N F.O([C@H]1CC[C@@H](CC1)N(C)CCCOC=1C=C(C(=CC=1Cl)CNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)OC)C(C(O)=O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound F.O([C@H]1CC[C@@H](CC1)N(C)CCCOC=1C=C(C(=CC=1Cl)CNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)OC)C(C(O)=O)(C=1SC=CC=1)C1=CC=CS1 LPRBLDKUDJHOFD-XFPMNCHFSA-N 0.000 claims 1
- AOPUMVRFTQOFIF-ZJTCZQGWSA-N F.O([C@H]1CC[C@@H](CC1)N(CCC(=O)NC=1C(=CC(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)Cl)C)C(C(O)=O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound F.O([C@H]1CC[C@@H](CC1)N(CCC(=O)NC=1C(=CC(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)Cl)C)C(C(O)=O)(C=1SC=CC=1)C1=CC=CS1 AOPUMVRFTQOFIF-ZJTCZQGWSA-N 0.000 claims 1
- CNLYMTUKZNDEKW-RGHVVQLISA-N F.O([C@H]1CC[C@@H](CC1)N(CCCOCCCCCCNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound F.O([C@H]1CC[C@@H](CC1)N(CCCOCCCCCCNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 CNLYMTUKZNDEKW-RGHVVQLISA-N 0.000 claims 1
- UTKFYKBUXIYENP-IYGAPYOLSA-N F.O([C@H]1CC[C@@H](CC1)N(CCOCCCCCCNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound F.O([C@H]1CC[C@@H](CC1)N(CCOCCCCCCNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 UTKFYKBUXIYENP-IYGAPYOLSA-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
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 229940099471 Phosphodiesterase inhibitor Drugs 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 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
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A61K31/435—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
-
- 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
- A61K31/435—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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Hydrogenated Pyridines (AREA)
Claims (17)
1. Jedinjenje iz formule (i), ili njegove farmaceutski prihvatljive soli ili solvati ili deuterisani derivat: • i X i Y predstavlja atom vodonika ili,• X zajedno saY formira grupu -CH=CH-, -CH2-O- ili -S-, pri čemu u slučaju -CH2-0- metilen grupa se veže na atom ugljenika u amido supstituentu koji drži X i atom kiseonika na atom ugljenika u prstenu fenila koji drži Y,• R1 i R2 nezavisno predstavlja atom vodonika ili C1-4 alkil grupu,• R3 predstavlja grupu iz formule:pri čemu:o Ra predstavlja atom vodonika, hidroksi grupu, hidroksimetil grupuili C1-4 alkil grupu,o Rb i RC nezavisno predstavlja tienil grupu, fenil grupu, benzil grupu ili C4-6 cikloalkil grupu,o Z predstavlja direktnu vezu ili atom kiseonika, io * predstavlja tačku spoja R3 na preostali molekul formule (l),• A1 i A2 nezavisno predstavljaju C1-6 alkilen grupu opciono supstituisanu sa jednom ili više C1-4 alkil grupe,• L predstavlja direktnu vezu, -O-, -NH(CO)-, -(CO)NH- ili -NH(CO)O- grupu, pri čemu u sllučaju -NH(CO)O-, atom azota je vezan na W supstituent i atom kiseonika se veže na A2 supstituent; i• W predstavlja direktnu vezu ili fenil grupu koja se opciono supstituiše sa jednim ili više supstituenata izabranih iz atoma halogena, C1-4 alkil grupa, C1-4 alkoksi grupa i cijano grupa.
2 Jedinjenje prema patentnom zahtevu 1 pri čemu X zajedno sa Y formira -CH=CH- ili -CH2-O- grupu, preporučljivo X zajedno saY formira -CH=CH- grupu.
3. Jedinjenje prema patentnim zahtevima 1 ili 2, pri čemu(a) R1 i R2 nezavisno predstavlja atom vodonika ili metil grupu, ili(a) R1 predstavalja atom vodonika i R2 predstavlja metil grupu.
4. Jedinjenje prema bilo kom od patentnih zahteva 1 do 3 pri čemu(a) R3 predstavlja grupu iz formule ii), pri čemu Z jeste atom kiseonika i Ra se bira iz atoma vodonika, hidroksi grupe ili metil grupe; ili (b) R3 predstavlja grupu iz formule i) pri čemu:• Ra predstavlja atom vodonika, hidroksi grupu ili metil grupu, preporučljivo Ra predstavlja hidrokisi grupu,• Rb i RC nezavisno predstavljaju tienil grupu, ciklopentil grupu, ili fenil grupu, preporučljivo i Rb i RC su tienil grupe.
5. Jedinjenje prema bilo kom od prethodnih patentnih zahteva pri čemu A1 i A2 nezavisno predstavljaju C1-6 alkilen grupu opciono supstituisanu sa jednom ili dve metil grupe.
6. Jedinjenje prema bilo kom od prethodnih patentnih zahteva pri čemu L predstavlja -O-, - NH(CO)- ili -NH(CO)O- grupu, pri čemu u slučaju -NH(CO)O-, atom azota se veže na W supstituent i atom kiseonika se veže na A2 supstituent.
7. Jedinjenje prema bilo kom od prethodnih patentnih zahteva pri čemu W predstavlja fenilen grupu koja se opciono supstituiše sa jednim ili dva supstituenta izabrana iz atoma hlora, metil grupe, metoksi grupe i cijano grupe.
8. Jedinjenje prema patentnom zahtevu 1 pri čemu• X zajedno sa Y formira -CH=CH- ili -CH2-O- grupu,• R1 predstavalja atom vodonika ili metil grupu.• R2 predstavalja atom vodonika ili metil grupu.• R3 predstavlja grupu iz formule (i), pri čemu Ra predstavlja hidroksi grupu i Rb i RC se nezavisno biraju iz fenil grupe, ciklopentil grupe i tienil grupe, ili Ra predstavlja grupu iz formule (ii), pri čemu Ra predstavlja metil grupu i Z predstavlja atom kiseonika,• A1 i A2 nezavisno predstavljaju C1-6 alkilen grupu opciono supstituisanu sa jednom ili dve metil grupe,• L se bira iz direktne veze, -O-, -NH(CO)- i -NH(CO)O- grupa i• W predstavlja direktnu vezu ili fenilen grupu koja se opciono supstituiše sa jednim ili sa više supstituenata izabranih iz atoma hlora, atoma fluora, metoksi grupe i cijano grupe.
9. Jedinjenje prema patentnom zahtevu 8 pri čemu• X zajedno sa Y formira -CH=CH- grupu,• R1 predstavalja atom vodonika,• R2 predstavalja atom vodonika ili metil grupu.• R3 predstavlja grupu iz formule (i), pri čemu Ra predstavlja hidroksi grupu i pri čemu su i Rb i RC tienil grupa,• A1 i A2 nezavisno predstavljaju C1-6 alkilen grupu opciono supstituisanu sa jednom ili dve metil grupe,• L se bira iz direktne veze, -O-, -NH(CO)- i -NH(CO)O- grupa i• W predstavlja direktnu vezu ili fenilen grupu koja se opciono supstituiše sa jednim ili sa dva supstituenta izabranih iz atoma hlora, atoma fluora, metoksi grupe i cijano grupe.
10. Jedinjenje prema patentnom zahtevu 9, pri čemu(a) R2 predstavlja atom vodonika, L se bira iz -0-, -NH(eO)- i- NH(eO)O- grupa, i W predstavlja fenilen grupu koja se supstituiše sa dva supstituenta izabrana iz atoma hlora, metoksi grupe i cijana grupe; ili(b) R2 predstavlja metil grupu, L se bira iz -0-, -NH(CO)- i - NH(CO)O- grupe, i W predstavlja fenilen grupu koja se supstituiše sa dva supstituenta izabrana iz atoma hlora, metoksi grupe i cijana grupe.
11. Jedinjenje prema patentnom zahtevu 1 jeste jedno od jedinjenja kao što jeMravlja kiselina - trans-4-[(9-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}nonil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat (2:1);Mravlja kiselina- trans-4-[{2-[4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)ami- no}etil)fenoksi]etil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat (1:1);Mravlja kiselina trans-4-[{3-[4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]ami- no}etil)fenoksi]propil}(metil)amino)cikloheksil hidroksi(di-2-tienil)acetat (1:1);trans-4-[{2-[(6-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)-etil]amino}heksil)oksi]etil}(metil)amino]cikloheksil hidroksi(di-2-tienil)-acetat hidrofluorid; trans-4-[{3-[(6-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}heksil)oksi]pro-pil}(metil)amino]cikloheksil hidroksi(di-2-tienil)-acetat hidrofluorid;Mravlja kiselina - trans-4-[{3-[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}me- til)fenoksi]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat (1:1);trans-4-[ {2-[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}metil)fe- noksi]etil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid;trans-4-[{3-[4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}propil)fenoksi]propil}(metil)amino]cikloheksil hidroksi(di-2- tienil)acetat hidrofluorid,trans-4-( (3-(2-hloro-4-(((2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etilamino)metil)-5- metoksifenilamino)-3-oksopropil)(metil)amino)-cikloheksil-hidroksi(di-2-tienil)acetat hidrofluorid;trans-4-( (3-(2-hloro-4-(((2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etilamino)metil)fenilamino)-3-oksopropil)(metil)amino)cikloheksil-hidroksi(di-2- tienil)acetat hidrofluorid,trans-4-[ {3-[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}metil}-5- metoksifenoksi]propil}(metil)amino]cikloheksil-hidroksi(di-2- tienil)acetat hidrofluorid;trans-4-[{2-[({[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro-hinolin-5-il)etil]amino}metil)- 5-metoksifenil]amino)karbonil)oksi]etil}-(metil)amino]cikloheksilhidroksi(di-2-tienil)acetat hidrofluorid,trans-4-[(3-{[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}metil)-5- metoksifenil]amino}-3-oksopropil)(metil)amino)-1-metilcikloheksil hidroksi(di-2-tienil)acetat,trans-4-[ (3-{[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}metil)fenil)ami- no}-3-oksopropil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),trans-4-[(4-{[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}metil)-5- metoksifenil)amino}-4-oksobutil)(metil)amino)-1-cikloheksil hidroksi(di-2-tienil)acetat,trans-4-[ (3-{[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}metil)-5- metoksifenil]amino}-3-oksopropil)(metil)amino)-1-cikloheksil hidroksi(di-2-tienil)acetat,trans-4-[ (3-{[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}metil)-3-metoksi-fenil)amino}-3-oksopropil)(metil)amino]-cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),trans-4-[(3-{[2,5-difluoro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}me- til)fenil)amino}-3-oksopropil)(metil)amino)-cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),trans-4-[(3-{[2-fluoro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}me-til)fenil)amino}-3-oksopropil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),trans-4-[ (3-{[2-hloro-4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}etil)-5- metoksifenil)amino}-3-oksopropil) (metil)amino]cikloheksilhidroksi(di-2-tienil)acetat hidrofluorid (1:2),trans-4-[ {3-[2-hloro-4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}etil)-5- metoksifenoksi]propil}(metil)-amino]cikloheksil hidroksi(di-2- tienil)acetat hidrofluorid (1:2),trans-4-[{2-[({[2-cijano-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}metil)- 5-metoksifenil]amino}karbonil)-oksi]etil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),trans-4-[{2-[({[2,5-difluoro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}metil)fenil]amino}karbonil)oksi]etil}-(metil)amino]cikloheksil hidroksi(di-2- tienil)acetat hidrofluorid (1:2),trans-4-[(3-{[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}metil)-5- metoksifenil]amino}-2,2-dimetil-3-oksopropil) (metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,trans-4-[{4-[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil)amino}metil)-5- metoksifenoksi)butil}(metil)amino]cikloheksil hidroksi(di-2-5 tienil)acetat hidrofluorid (1:2),trans-4-[{2-[({[2-hloro-4-({[(2R)-2-hidroksi-2-(5-hidroksi-3-okso-3,4-dihidro-2H-1,4- benzoksazin-8-il)etil]ami-no}metil)-5-metoksifenil]amino}karbonil)oksi)- etil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat,trans-4-[(9-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etil]amino}nonil)(metil)amino]cikloheksil 9-metii-9H-ksanten-9-karboksilat,trans-4-[{2-[({[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro-hinolin-5- il)etil]amino}metil)- 5-metoksifenil]amino}karbonil)oksi]etil}-(metil)-amino]cikloheksil (2R)-ciklopentil(hidroksi)fenilacetat, itrans-4-[{2-[({[2-hloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro-hino!in-5-il)etil)amino}metil)- 5-metoksifenil)amino}karbonil)oksi]etil}-(metil) amino]cikloheksil (2S)-ciklopentil(hidroksi)2-tienilacetat;ili njegove farmaceutski prihvatljive soli ili solvati ili deuterisani derivat.
1 2. Jedinjenje prema patentnom zahtevu 11 koje je trans-4-((3-(2-hloro-4-(((2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrohinolin-5-il)etilamino)metil)-5-metoksifenilamino)-3- oksopropil)(metil)amino)-cikloheksil hidroksi(di-2- tienil)acetat hidrofluorid; ili njihovi solvati ili deuterisani deriat.
13. Jedinjenje prema patentnom zahtevu 11 koje je trans-4-[{2-[({[2-hloro-4-({[(2R)-2- hidroksi-2-(8-hidroksi-2-okso-1,2- dihidrohinolin-5-il)etil]amino}meti1)-5-metoksifenil]amino}karbonil)oksi)eti1}-(metil)amino)-cikloheksi1- hidroksi(di-2-tienil)acetat hidrofluorid, ili solvati ili njihov deuterisani derivat.
14. Jedinjenje prema bilo kom od patentnih zahteva 1 do 13 za upotrebu u lečenju ljudskog tela ili tela životinje u vidu terapije.
15. Jedinjenje prema bilo kom od patentnih zahteva 1 do 13 za upotrebu u lečenju bolesti izabrane iz bolesti pluća, glaukoma, neuroloških poremećaja, poremećaja srca, poremećaja upale i gastrointestinalnih poremećaja.
16. Farmaceutska supstanca koja obuhvata jedinjenje kako je definisano u bilo kom od patentnih zahteva 1 do 13 u vezi sa farmaceutski prihvatljivim razblaživačem ili nosačem.
17. Kombinovani proizvod obuvhata (i) jedinjenje prema bilo kom od patentnih zahteva 1 do 13; i (ii) još jedno jedinjenje izabrano iz nekog kortikosteroida i PDE inhibitora.
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| US36504510P | 2010-07-16 | 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 |
| EP11720386.9A EP2569308B1 (en) | 2010-05-13 | 2011-05-13 | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
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| 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 |
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| 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 |
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