HRP20170307T1 - NOVI DERIVATI CIKLOHEKSILAMINA KOJI POSJEDUJU DJELOVANJA AGONISTA ß2 ADRENERGIČKOG RECEPTORA I ANTAGONISTA M3 MUSKARINSKOG RECEPTORA - Google Patents
NOVI DERIVATI CIKLOHEKSILAMINA KOJI POSJEDUJU DJELOVANJA AGONISTA ß2 ADRENERGIČKOG RECEPTORA I ANTAGONISTA M3 MUSKARINSKOG RECEPTORA Download PDFInfo
- Publication number
- HRP20170307T1 HRP20170307T1 HRP20170307TT HRP20170307T HRP20170307T1 HR P20170307 T1 HRP20170307 T1 HR P20170307T1 HR P20170307T T HRP20170307T T HR P20170307TT HR P20170307 T HRP20170307 T HR P20170307T HR P20170307 T1 HRP20170307 T1 HR P20170307T1
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxy
- amino
- methyl
- group
- ethyl
- Prior art date
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- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title 1
- 239000000048 adrenergic agonist Substances 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- -1 {[2-chloro-4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydro-quinoline-5- yl)ethyl]amino}methyl)-5-methoxyphenyl]amino}carbonyl Chemical group 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 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 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 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
- 229910052757 nitrogen Inorganic materials 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
- 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
- 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
- WGRRMDFUMITLJB-ZJTCZQGWSA-N F.CN(CCC(=O)Nc1ccc(CNC[C@H](O)c2ccc(O)c3[nH]c(=O)ccc23)cc1Cl)[C@H]1CC[C@@H](CC1)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound F.CN(CCC(=O)Nc1ccc(CNC[C@H](O)c2ccc(O)c3[nH]c(=O)ccc23)cc1Cl)[C@H]1CC[C@@H](CC1)OC(=O)C(O)(c1cccs1)c1cccs1 WGRRMDFUMITLJB-ZJTCZQGWSA-N 0.000 claims 1
- PVDQCNRZXDIHDO-PSDISIQPSA-N F.O([C@H]1CC[C@@H](CC1)N(C)CCCCOC=1C=C(C(=CC=1Cl)CNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)OC)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound F.O([C@H]1CC[C@@H](CC1)N(C)CCCCOC=1C=C(C(=CC=1Cl)CNC[C@H](O)C=1C=2C=CC(=O)NC=2C(O)=CC=1)OC)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 PVDQCNRZXDIHDO-PSDISIQPSA-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
- 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
- SILWREKWJOTGHG-RXCVGROASA-N F.O([C@H]1CC[C@@H](CC1)N(CCOC=1C=CC(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=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(CCOC=1C=CC(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 SILWREKWJOTGHG-RXCVGROASA-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
- WLVUPWOZIUUGMW-RGHVVQLISA-N OC=O.O([C@H]1CC[C@@H](CC1)N(CCCCCCCCCNC[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 OC=O.O([C@H]1CC[C@@H](CC1)N(CCCCCCCCCNC[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 WLVUPWOZIUUGMW-RGHVVQLISA-N 0.000 claims 1
- MKUZMLUPXCBRMQ-UZNBJRRRSA-N OC=O.O([C@H]1CC[C@@H](CC1)N(CCCOC=1C=CC(CCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound OC=O.O([C@H]1CC[C@@H](CC1)N(CCCOC=1C=CC(CCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 MKUZMLUPXCBRMQ-UZNBJRRRSA-N 0.000 claims 1
- LKLTUAVQAOQHIF-KTZFPCHUSA-N OC=O.O([C@H]1CC[C@@H](CC1)N(CCCOC=1C=CC(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound OC=O.O([C@H]1CC[C@@H](CC1)N(CCCOC=1C=CC(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LKLTUAVQAOQHIF-KTZFPCHUSA-N 0.000 claims 1
- DDCISFNOIPBCQF-KTZFPCHUSA-N OC=O.O([C@H]1CC[C@@H](CC1)N(CCOC=1C=CC(CCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 Chemical compound OC=O.O([C@H]1CC[C@@H](CC1)N(CCOC=1C=CC(CCNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)=CC=1)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 DDCISFNOIPBCQF-KTZFPCHUSA-N 0.000 claims 1
- 229940123932 Phosphodiesterase 4 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
- 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
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 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
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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]
-
- 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
-
- 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
-
- 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
-
- 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)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Cardiology (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)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Plant Substances (AREA)
- Quinoline Compounds (AREA)
Claims (17)
1. Spoj formule (I) ili njegove farmaceutski prihvatljive soli ili solvati ili deuterirani derivati:
[image]
naznačen time, što:
• i X i Y predstavljaju atom vodika ili,
• X zajedno s Y formira grupu -CH=CH-, -CH2-O- ili -S, pri čemu je u slučaju -CH2-O- metilenska grupa povezana na atom ugljika u amido supstituentu koji sadrži X, a atom kisika je povezan na atom ugljika u fenilnom prstenu koji sadrži Y,
• R1 i R2 zasebno predstavljaju atom vodika ili C1-4alkilnu grupu,
• R3 predstavlja grupu formule:
[image]
[image]
naznačen time, što:
o Ra predstavlja atom vodika, hidroksi grupu, hidroksimetilnu grupu ili C1-4alkilnu grupu,
o Rb i Rc zasebno predstavljaju tienilnu grupu, fenilnu grupu, benzilnu grupu ili C4-6cikloalkilnu grupu,
o Z predstavlja direktnu vezu ili atom kisika, i
o * predstavlja točku vezivanja R3 na ostatak molekule formule (I),
• A1 i A2 zasebno predstavljaju C1-6alilensku grupu opcionalnu supstituiranu s jednom ili više C1-4alkilnih grupa,
• L predstavlja direktnu vezu, -O-, -NH(CO)-, -(CO)NH- ili -NH(CO)O- grupu, pri čemu je u slučaju -NH(CO)O- atom dušika povezan na W supstituent, a atom kisika je povezan na A2 supstituent; i
• W predstavlja direktnu vezu ili fenilensku grupu koja je opcionalno supstituirana s jednim ili više supstituenata odabranih iz atoma halogena, C1-4alkilne grupe, C1-4 alkoksi grupe i cijano grupe.
2. Spoj prema zahtjevu 1, naznačen time, što X zajedno s Y formira -CH=CH- ili -CH2-O- grupu, poželjno X zajedno s Y formira -CH=CH- grupu.
3. Spoj prema zahtjevu 1 ili 2, naznačen time, što
(a) R1 i R2 zasebno predstavljaju atom vodika ili metilnu grupu; ili
(b) R1 predstavlja atom vodika, a R2 predstavlja metilnu grupu.
4. Spoj prema bilo kojem zahtjevu od 1 do 3, naznačen time, što
(a) R3 predstavlja grupu formule ii), pri čemu je Z atom vodika, a Ra je odabran iz atoma vodika, hidroksi grupe ili metilne grupe; ili
(b) R3 predstavlja atom formule i) pri čemu:
• Ra predstavlja atom vodika, hidroksi grupu ili metilnu grupu, poželjno Ra predstavlja hidroksi grupu,
• Rb i Rc zasebno predstvljaju tienilnu grupu, ciklopentilnu grupu ili fenilnu grupu, poželjno Rb i Rc su oba tienilne grupe.
5. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što A1 i A2 zasebno predstavljaju C1-6alkilensku grupu opcionalno supstituiranu s jednom ili dvije metilne grupe.
6. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što L predstavlja -O-, -NH(CO)- ili -NH(CO)O- grupu, pri čemu je u slučaju -NH(CO)-O- atom dušika povezan na W supstituent, a atom kisika je povezan na A2 supstituent.
7. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što W predstavlja fenilensku grupu koja je opcionalno supstituirana s jednim ili dva supstituenta odabrana iz atoma klora, metilne grupe, metoksi grupe i cijano grupe.
8. Spoj prema zahtjevu 1, naznačen time, što
• X zajedno s Y formira -CH=CH- ili -CH2-O- grupu,
• R1 predstavlja atom vodika ili metilnu grupu,
• R2 predstavlja atom vodika ili metilnu grupu,
• R3 predstavlja formulu (i), pri čemu Ra predstavlja hidroksi grupu, a Rb i Rc su zasebno odabrani iz fenilne grupe, ciklopentilne grupe i tienilne grupe, ili Ra predstavlja grupu formule (ii), pri čemu Ra predstavlja metilnu grupu, a Z predstavlja atom kisika,
• A1 i A2 zasebno predstavljaju C1-6 alkilensku grupu koja je opcionalno supstituirana s jednom ili dvije metilne grupe,
• L je odabran iz direktne veze, -O-, -NH(CO)- i -NH(CO)O- grupa i
• W predstavlja direktnu vezu ili fenilensku grupu koja je opcionalno supstituirana s jednim ili dva supstituenta odabrana iz atoma klora, atoma fluora, metoksi grupe i cijano grupe.
9. Spoj prema zahtjevu 8, naznačen time, što
• X zajedno s Y formira -CH=CH- grupu
• R1 predstavlja atom vodika,
• R2 predstavlja atom vodika ili metilnu grupu,
• R3 predstavlja grupu formule (i), pri čemu Ra predstavlja hidroksi grupu, a Rb i Rc su oboje tienilna grupa,
• A1 i A2 zasebno predstavljaju C1-6 alkilensku grupu koja je opcionalno supstituirana s jednom ili dvije metilne grupe,
• L je odabran iz direktne veze, -O-, -NH(CO)- i -NH(CO)O- grupa i
• W predstavlja direktnu vezu ili fenilensku grupu koja je opcionalno supstituirana s jednim ili dva supstituenta odabrana iz atoma klora, metoksi grupe i cijano grupe.
10. Spoj prema zahtjevu 9, naznačen time, što
(a) R2 predstavlja atom vodika, L je odabran iz -O-, -NH(CO)- i -NH(CO)O- grupe, a W predstavlja fenilensku grupu koja je supstituirana s jednim ili dva supstituenta odabrana iz atoma klora, metoksi grupe i cijano grupe ili
(b) R2 predstavlja atom vodika, L je odabran iz -O-, -NH(CO)- i -NH(CO)O- grupe, a W predstavlja fenilensku grupu koja je supstituirana s dva supstituenta odabrana iz atoma klora, metoksi grupe i cijano grupe.
11. Spoj prema zahtjevu 1, koji je
Mravlja kiselina -trans-4-[(9-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-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-dihidrokvinolin-5-il)etil] amino}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-dihidrokvinolin-5-il)etil]amino} 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-dihidrokvinolin-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-dihidrokvinolin-5-il)-etil]amino}heksil)oksi]propil}(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-dihidrokvinolin-5-il)etil]amino} metil) 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-dihidrokvinolin-5-il)-etil]amino}metil)fenoksi]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-dihidrokvinolin-5-il)etil]amino}propil)fenoksi]propil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid;
trans-4-((3-(2-kloro-4-(((2R)-2hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etilamino)metil)-5-metoksifenilamino)-3-oksopropil)(metil)amino)-cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid;
trans-4-((3-(2-kloro-4-(((2R)-2hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etilamino)metil)fenilamino)-3-oksopropil)(metil)amino)-cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid;
trans-4-[{3-[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil]amino}metil)-5-metoksifenoksi]propil}(metil)amino]cikloheksil-hidroksi(di-2-tienil)acetat hidrofluorid;
trans-4-[{2-[({[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro-kvinolin-5-il)etil]amino}metil)-5-metoksifenil]amino}karbonil)oksi]etil}-(metil)amino]-cikloheksilhidroksi(di-2-tienil)acetat hidrofluorid;
trans-4-[(3-{[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-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-dihidrokvinolin-5-il)etil)amino}metil)fenil]amino}-3-oksopropil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),
trans-4-[(4-{[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil)amino}metil)-5-metoksifenil]amino}-4-oksobutil)(metil)amino]-cikloheksil hidroksi(di-2-tienil)acetat,
-trans-4-[(3-{[2-fluoro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil)amino}metil)-5-metoksifenil]amino}-3-oksopropil)(metil)amino]-cikloheksil hidroksi(di-2-tienil)acetat,
trans-4-[(3-{[4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil)amino}metil)-3-metoksifenil]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-dihidrokvinolin-5-il)etil)amino}metil)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-dihidrokvinolin-5-il)etil)amino}metil)fenil]amino}-3-oksopropil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),
trans-4-[(3-{[2-kloro-4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etil)amino}etil)-5-metoksifenil]amino}-3-oksopropil)(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),
trans-4-[{3-[2-kloro-4-(2-{[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-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-dihidrokvinolin-5-il)etil]amino}metil)-5-metoksifenil]amino}karbonol)-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-dihidrokvinolin-5-il)etil]amino}metil)fenil]amino}karbonol)-oksi]etil}-(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),
trans-4-[(3-{[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-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-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolih-5-il)etil]amino}metil)-5-metoksifenoksi]butil}(metil)amino]cikloheksil hidroksi(di-2-tienil)acetat hidrofluorid (1:2),
trans-4-[{2-[({[2-kloro-4-({[(2R)-2-hidroksi-2-(5-hidroksi-3-okso-3,4-dihidro-2H-1,4-benzoksazin-8-il)etil]amino}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-dihidrokvinolin-5-il)etil]-amino}nonil)(metil)amino]cikloheksil 9-metil-9H-ksanten-9-karboksilat,
trans-4-[{2-[({[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro-kvinolin-5-il)etil]amino}metil)-5-metoksifenil]amino}karbonil)oksi]etil}-(metil)-amino]cikloheksil (2R)-ciklopentil(hidroksi)fenilacetat, i
trans-4-[{2-[({[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro-kvinolin-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 deuterirani derivati.
12. Spoj prema zahtjevu 11, koji je trans-4-((3-(2-kloro-4-(((2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidrokvinolin-5-il)etilamino)metil)-5-metoksifenilamino)-3-oksopropil)(metil)amino)-cikloheksil hidroksi(di-2-tienil)acetat
hidrofluorid ili njegovi solvati ili deuterirani derivati.
13. Spoj prema zahtjevu 11, koji je -trans-4-[{2-[({[2-kloro-4-({[(2R)-2-hidroksi-2-(8-hidroksi-2-okso-1,2-dihidro kvinolin-5-il)etil]amino}metil)-5-metoksifenil]amino}karbonil)oksi]etil}-(metil)amino]-cikloheksilhidroksi(di-2-tienil)acetat hidrofluorid ili njegovi solvati ili deuterirani derivati.
14. Spoj prema bilo kojem zahtjevu od 1 do 13 za primjenu u liječenju ljudskog ili životinjskog organizma pomoću terapije.
15. Spoj prema bilo kojem zahtjevu od 1 do 13 za primjenu u liječenju bolesti odabrane iz plućnih bolesti, glaukoma, neuroloških poremećaja, srčanih poremećaja, upalnih i gastrointestinalnih poremećaja.
16. Farmaceutski pripravak koji se sastoji od spoja kako je definirano u bilo kojem zahtjevu od 1 do 13 asociranog s farmaceutski prihvatljivim otapalom ili nosačem.
17. Kombinirani proizvod koji se sastoji od (i) spoja prema bilo kojem zahtjevu od 1 do 13 i (ii) drugog spoja odabranog iz kortikosteroida i inhibitora PDE4.
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| EP11720386.9A EP2569308B1 (en) | 2010-05-13 | 2011-05-13 | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| PCT/EP2011/002376 WO2011141180A1 (en) | 2010-05-13 | 2011-05-13 | NEW CYCLOHEXYLAMINE DERIVATIVES HAVING β2 ADRENERGIC AGONIST AND M3 MUSCARINIC ANTAGONIST ACTIVITIES |
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| 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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