HRP20170052T1 - Novi derivati (aza)benzhidril etera, njihov postupak dobivanja i njihova uporaba kao liganda h4-receptora za terapeutske primjene - Google Patents
Novi derivati (aza)benzhidril etera, njihov postupak dobivanja i njihova uporaba kao liganda h4-receptora za terapeutske primjene Download PDFInfo
- Publication number
- HRP20170052T1 HRP20170052T1 HRP20170052TT HRP20170052T HRP20170052T1 HR P20170052 T1 HRP20170052 T1 HR P20170052T1 HR P20170052T T HRP20170052T T HR P20170052TT HR P20170052 T HRP20170052 T HR P20170052T HR P20170052 T1 HRP20170052 T1 HR P20170052T1
- Authority
- HR
- Croatia
- Prior art keywords
- methylpiperidin
- yloxy
- methyl
- fluoro
- alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims 5
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 polyhydroxy Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 230000000172 allergic effect Effects 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 230000000241 respiratory effect Effects 0.000 claims 2
- 102220067365 rs143592561 Human genes 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- PDNHLCRMUIGNBV-UHFFFAOYSA-N 1-pyridin-2-ylethanamine Chemical compound CC(N)C1=CC=CC=N1 PDNHLCRMUIGNBV-UHFFFAOYSA-N 0.000 claims 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims 1
- 102000004023 5-Lipoxygenase-Activating Proteins Human genes 0.000 claims 1
- 108090000411 5-Lipoxygenase-Activating Proteins Proteins 0.000 claims 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000031104 Arterial Occlusive disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical group C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims 1
- 208000017667 Chronic Disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009137 Chronic sinusitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010051055 Deep vein thrombosis Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 206010014950 Eosinophilia Diseases 0.000 claims 1
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 1
- 208000004262 Food Hypersensitivity Diseases 0.000 claims 1
- 108090000110 Histamine H1 Receptors Proteins 0.000 claims 1
- 108090000981 Histamine H3 receptors Proteins 0.000 claims 1
- 102000004384 Histamine H3 receptors Human genes 0.000 claims 1
- 101150056637 Hrh2 gene Proteins 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010020853 Hypertonic bladder Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims 1
- 206010057672 Male sexual dysfunction Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 206010028735 Nasal congestion Diseases 0.000 claims 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 1
- 102100022364 Polyunsaturated fatty acid 5-lipoxygenase Human genes 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010062237 Renal impairment Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010038687 Respiratory distress Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000036284 Rhinitis seasonal Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 239000000150 Sympathomimetic Substances 0.000 claims 1
- 208000001435 Thromboembolism Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 206010047249 Venous thrombosis Diseases 0.000 claims 1
- 206010064948 Viral rhinitis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
- 125000005096 aminoalkylaminocarbonyl group Chemical group 0.000 claims 1
- 229960003556 aminophylline Drugs 0.000 claims 1
- FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 claims 1
- 239000003434 antitussive agent Substances 0.000 claims 1
- 229940124584 antitussives Drugs 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 208000021328 arterial occlusion Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- YWGDOWXRIALTES-NRFANRHFSA-N bepotastine Chemical compound C1CN(CCCC(=O)O)CCC1O[C@H](C=1N=CC=CC=1)C1=CC=C(Cl)C=C1 YWGDOWXRIALTES-NRFANRHFSA-N 0.000 claims 1
- 229960002071 bepotastine Drugs 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 229960001803 cetirizine Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 208000027744 congestion Diseases 0.000 claims 1
- 229940111134 coxibs Drugs 0.000 claims 1
- 229960000265 cromoglicic acid Drugs 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 claims 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 1
- 239000000850 decongestant Substances 0.000 claims 1
- 229960001271 desloratadine Drugs 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 210000002249 digestive system Anatomy 0.000 claims 1
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims 1
- 229960005426 doxepin Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 239000003172 expectorant agent Substances 0.000 claims 1
- 235000020932 food allergy Nutrition 0.000 claims 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 210000003630 histaminocyte Anatomy 0.000 claims 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 229960004958 ketotifen Drugs 0.000 claims 1
- 230000005977 kidney dysfunction Effects 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 1
- 210000004324 lymphatic system Anatomy 0.000 claims 1
- 201000005857 malignant hypertension Diseases 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000000510 mucolytic effect Effects 0.000 claims 1
- 229940066491 mucolytics Drugs 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 229960002259 nedocromil sodium Drugs 0.000 claims 1
- 208000037916 non-allergic rhinitis Diseases 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 208000020629 overactive bladder Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000005592 polycycloalkyl group Polymers 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 230000001932 seasonal effect Effects 0.000 claims 1
- 230000003637 steroidlike Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940127230 sympathomimetic drug Drugs 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 229960000278 theophylline Drugs 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 210000001635 urinary tract Anatomy 0.000 claims 1
- 239000005526 vasoconstrictor agent Substances 0.000 claims 1
Classifications
-
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P17/00—Drugs for dermatological disorders
-
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (15)
1. Spojevi s formulom (I) :
[image]
R1 predstavlja C1-C6 alkil;
Het predstavlja ne aromatski monociklički 3 do 7 člani heterocikal koji sadrži jedan dušikov atom i proizvoljno 1 do 3 dodatna heteroatoma odabrana od O, S, pri čemu navedeni dušikov atom je vezan na R1;
A predstavlja jednostruku vezu ili skupinu -C1-C6 alkil-;
svaki R2, R3, R4, R5, R6 isti ili različit je neovisno odabran od:
• vodika
• halo; azido; cijano; hidroksi; nitro;
• alkila; alkoksi; alkilsulfanila; alkenila; alkinila; alkeniloksi; alkeniloksi; alkenilsulfanila; alkinilsulfanila; cikloalkoksi; cikloalkilalkila;
čiji alkilni, alkenilni, alkinilni ili cikloalkilni dio može biti supstituiran s jednim ili više od halo, hidroksi, polihidroksi, alkoksi, hidroksialkoksi, cijano, amino, aminoalkil, alkilamino, dialkilamino, aminoalkilamino, aminoalkilaminokarbonil, alkoksikarbonilamino, diarilmetilimino (gdje je aril proizvoljno supstituiran s jednim ili više od hidroksi ili halo), cikloalkenilimino (gdje je cikloalkenil proizvoljno supstituiran s jednim ili više od alkil, OH), alkilsulfanil, alkilsulfinil, alkilsulfonil, cikloalkil, policikloalkil, cikloalkenil, policikloalkenil, gvanidino, alkilkarbonilgvanidino, acilgvanidino, cijanogvanidino, alkoksikarbonilgvanidino, alkoksikarbonil, alkoksikarbonilalkilamino, alkoksikarbonilalkilcikloalkil, alkoksikarbonilheterociklil, aminokarbonil, alkilaminokarbonil, alkilkarbonil, alkilkarbonilalkoksi, ariloksi, arilsulfanil, arilsulfinil, arilsulfonil, heteroaril, heterociklil (heterociklil je proizvoljno supstituiran s jednim ili više od okso, amino, imino), heteroariloksi, heterocikliloksi, heteroarilamino, heterociklilamino, hidrazinokarbonil, hidroksialkilcikloalkil, N-alkil(tioureido), ftalimido, ureido, oksocikloalkenilamino supstituiran s amino, karbamimidoilheterociklil;
• amino; alkilamino; alkilkarbonil; alkoksikarbonil; alkilsulfanil; alkilsulfinil; alkilsulfonil; alkilsulfoniloksi
pri čemu:
alkil može biti supstituiran sa jednim ili više halo;
i
barem jedan od R2, R3, R4, R5, R6 je različit od H
svaki Xi , isti ili različit je odabran od -N=, -C(Ri)= i -C(Ri')= ,
i predstavlja oznake 7, 8, 9 ili 10
pri čemu
bilo koji od Xi je -N= i drugi su -C(Ri)= ili svaki Xi je odabran od -C(Ri)= i -C(Ri')= uz barem Xi je -C(Ri')=
pri čemu za svaki i navedeni Xi može biti isti ili različit i navedeni Ri može biti isti ili različit
tako da
[image]
predstavlja supstituirani fenil ili proizvoljno supstituirani piridil,
navedeni Ri(i=7, 8, 9, 10) su odabrani od
• H
• Ri'(i'=7, 8, 9, 10)
navedeni Ri'(i'=7, 8, 9, 10) su odabrani od:
• halo, cijano, hidroksi, nitro,
• alkil; alkoksi; alkilsulfanil; alkenil; alkinil; alkeniloksi; alkeniloksi; alkenilsulfanil; alkinilsulfanil; cikloalkoksi; cikloalkilalkil
čiji alkilni, alkenilni, alkinilni ili cikloalkilni dio može biti supstituiran s jednim ili više od halo, hidroksi, polihidroksi, alkoksi;
• aril; arilalkil; ariloksi; arilalkoksi; arilalkilamino; arilalkilsulfanil; heteroaril; heteroariloksi
čiji (hetero)arilni dio može biti supstituiran s jednim ili više od amino, halo, alkil, (poli)haloalkil, hidroksialkil, alkoksi, (poli)haloalkoksi, alkoksikarbonilamino, alkilkarbonil, alkilsulfanil, alkilsulfinil, alkilsulfonil, nitro, cijanoalkil, ili kondenziran s nearomatskim heterociklom;
i pri čemu R9 i R10 mogu zajedno s atomima ugljika na koje su oni vezani tvoriti aromatski prsten
kao i enantiomeri, dijastereomeri, njihovi smjese i farmaceutski prihvatljive soli, tautomeri, hidrati i solvati.
uz iznimku spojeva, gdje istodobno:
X9 je -CR9'=,
X7=X8=X10= -CH= ,
R4 nije H i
R2=R3= R5=R6= H.
2. Spojevi prema zahtjevu 1 naznačeni time da spojevi s formulom (I) su prema formuli (Ia):
[image]
naznačeni time da
R1, Het, A, R2-6 su definirani kao u zahtjevu 1
X7 ili X9 predstavlja -N= i drugi od X7 ili X9 predstavlja -CR7= ili -CR9= te gdje su R8, R10 i proizvoljno R7 ili R9, isti ili različiti odabrani od
• H
• halo, cijano, hidroksi, nitro,
• alkila; alkoksi; alkilsulfanila; alkenila; alkinila; alkeniloksi; alkeniloksi; alkenilsulfanila; alkinilsulfanila; cikloalkoksi; cikloalkilalkila
čiji alkilni, alkenilni, alkinilni ili cikloalkilni dio može biti supstituiran s jednim ili više od halo, hidroksi, polihidroksi, alkoksi;
• arila; arilalkil; ariloksi; arilalkoksi; arilalkilamino; arilalkilsulfanila; heteroarila; heteroariloksi
čiji (hetero)arilni dio može biti supstituiran s jednim ili više od amino, halo, alkil, (poli)haloalkil, hidroksialkil, alkoksi, (poli)haloalkoksi, alkoksikarbonilamino, alkilkarbonil, alkilsulfanil, alkilsulfinil, alkilsulfonil, nitro, cijanoalkil, ili kondenziran s nearomatskim heterociklom;
i pri čemu R9 i R10 mogu zajedno s atomima ugljika na koje su oni vezani tvoriti aromatski prsten
kao i enantiomeri, dijastereomeri, njihovi smjese i farmaceutski prihvatljive soli, tautomeri, hidrati i solvati.
3. Spojevi prema zahtjevu 1, naznačeni time da spojevi s formulom (I) su sa formulom (Ib):
[image]
pri čemu:
R1, Het, A, R2-6 su definirani kao u zahtjevu 1 i
svaki od R7-R10 je odabran od
• H
• halo, cijano, hidroksi, nitro,
• alkila; alkoksi; alkilsulfanila; alkenila; alkinila; alkeniloksi; alkeniloksi; alkenilsulfanila; alkinilsulfanila; cikloalkoksi; cikloalkilalkila
čiji alkilni, alkenilni, alkinilni ili cikloalkilni dio može biti supstituiran s jednim ili više od halo, hidroksi, polihidroksi, alkoksi;
• arila; arilalkila; ariloksi; arilalkoksi; arilalkilamino; arilalkilsulfanila; heteroarila; heteroariloksi
čiji (hetero)arilni dio može biti supstituiran s jednim ili više od amino, halo, alkil, (poli)haloalkil, hidroksialkil, alkoksi, (poli)haloalkoksi, alkoksikarbonilamino, alkilkarbonil, alkilsulfanil, alkilsulfinil, alkilsulfonil, nitro, cijanoalkil, ili kondenziran s nearomatskim heterociklom;
i pri čemu R9 i R10 mogu zajedno s atomima ugljika na koje su oni vezani tvoriti aromatski prsten;
pri čemu barem jedan od R7-R10 je različit od H, i
kada R9 nije H, R7=R8=R10=H, i R2=R3=R5=R6=H, tada R4 je H; ili
kada R4 nije H, R7=R8=R10=H, i R2=R3=R5=R6=H tada R9 je H.
kao i enantiomeri, dijastereomeri, njihovi smjese i farmaceutski prihvatljive soli, tautomeri, hidrati i solvati.
4. Spojevi prema bilo kojem od zahtjeva 1, 2 ili 3, naznačeni time da
R1 predstavlja metil.
5. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da Het predstavlja piperidin.
6. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da A predstavlja jednostruku vezu;
svaki R2, R3, R4, R5, R6 isti ili različit se neovisno bira od:
• vodika
• halo; hidroksi;
• alkila; alkoksi; alkenila;
čiji alkilni, alkenilni, alkinilni dio može biti supstituiran s jednim ili više od halo, amino, alkoksikarbonilamino,
gdje je barem jedan od R2, R3, R4, R5, R6 različit od H;
i
[image]
predstavlja supstituirani fenil ili proizvoljno supstituirani piridil, navedeni supstituent(i) je/su odabrani od
• H
• Ri'
navedeni Ri' su odabrani od:
• halo, cijano,
• alkil proizvoljno supstituiran s jednim ili više halo;
• aril;
i pri čemu R9 i R10 mogu zajedno s atomima ugljika na koje su oni vezani tvoriti aromatski prsten
uz iznimku spojeva, gdje istodobno:
X9 je -CR9'=,
X7=X8=X10= -CH= ,
R4 nije H i
R2=R3= R5=R6= H.
7. Spojevi prema bilo kojem od prethodnih zahtjeva naznačeni time da su odabrani iz niza koji čine:
- 2-[(2-fluor-5-trifluormetoksifenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 5-klor-2-[(2-fluor-4-metilfenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 2-[(2-fluor-4-metilfenil)(-metilpiperidin-4-iloksi)metil]piridin
- 5-klor-2-[(2-fluor-5-trifluormetoksifenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 6-{3-[(1-metilpiperidin-4-iloksi)piridin-2-ilmetil]fenil}heks-5-inilamin
- 4-[(2-fluor-5-trifluormetoksifenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 2-[(2-fluor-4-metilfenil)(1-metilpiperidin-4-iloksi)metil]-4-metilpiridin
- 2-[(2-fluor-5-trifluormetoksifenil)(1-metilpiperidin-4-iloksi)metil]-4-metilpiridin
- 5-klor-2-[(4-klorfenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 5-fluor-2-[(2-fluor-4-metilfenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 5-fluor-2-[(2-fluor-5-trifluormetoksifenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 5-klor-2-[(3-metoksifenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 5-klor-2-[(3-jodfenil)(1-metilpiperidin-4-iloksi)metil]piridin
- 2-[(2-fluor-4-metilfenil)(1-metilpiperidin-4-iloksi)metil]-4-trifluormetilpiridin
- 2,3-difluor-6-[(5-fluorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]fenol
- 6-[(5-klorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-2,3-difluorfenol
- etil ester (6-{3-[(1-metilpiperidin-4-iloksi)piridin-2-ilmetil]fenil}heks-5-inil)karbaminske kiseline
- 6-{3-[(5-klorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]fenil}heks-5-inilamin
- 2-[(1-metilpiperidin-4-iloksi)piridin-2-ilmetil]fenol
- 5-fluor-2-[(5-fluorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]fenol
- 2-fluor-6-[(5-fluorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-3-metilfenol
- 6-[(5-klorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-2-fluor-3-metilfenol
- 2-[(5-klorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-5-fluorfenol
- 2-[(5-fluorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-5-metilfenol
- 2-[(5-klorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-5-metilfenol
- 2-fluor-6-[(4-fluorpiridin-2-il)(1-metilpiperidin-4-iloksi)metil]-3-metilfenol
- 4-[(3-jodfenil)-p-tolilmetoksi]-1-metilpiperidin
- 4-[(2-fluor-5-trifluormetoksifenil)naphthalen-2-ilmetoksi]-1-metilpiperidin
- 4-[(2-fluor-4-metilfenil)naphthalen-2-il-metoksi]-1-metilpiperidin
- 4-[(3,4-diklorfenil)(2-fluor-4-metilfenil)metoksi]-1-metilpiperidin
- 4-[(3,4-diklorfenil)(2-fluor-5-trifluormetoksifenil)metoksi]-1-metilpiperidin
- 4-[(2-fluorfenil)-(2-fluor-5-trifluormetoksifenil)metoksi]-1-metilpiperidin
- 4-[(4-klorfenil)(2-fluor-5-trifluormetoksifenil)metoksi]-1-metilpiperidin
- 4-[(4-klorfenil)(2-fluor-4-metilfenil)metoksi]-1-metilpiperidin
- 4-[(4-klorfenil)(3-jodfenil)metoksi]-1-metilpiperidin
- 6-{3-[(4-klorfenil)(1-metilpiperidin-4-iloksi)metil]fenil}heks-5-inilamin
- 2-[(3-jodfenil)(1-metilpiperidin-4-iloksi)metil]piridin
kao i enantiomeri, dijastereomeri, njihovi smjese i farmaceutski prihvatljive soli, tautomeri, hidrati i solvati.
8. Postupak za dobivanje spojeva s formulom (I) prema bilo kojem od prethodnih zahtjeva naznačen time da sadrži kondenzaciju alkohola formule (III) u kojoj su R, Het i A kako je definirano u bilo kojem od zahtjeva 1 do 6 s alkoholom s formulom (IV) u kojoj su R2, R3, R4, R5, R6, X7, X8, X9 i X10 kako je definirano u bilo kojem od zahtjeva 1 do 6:
[image]
9. Postupak za dobivanje spojeva s formulom (I) prema bilo kojem od zahtjeva 1 do 7 naznačen time da sadrži kondenzaciju alkohola formule (III) u kojoj su R, Het i A kako je definirano u bilo kojem od zahtjeva 1 do 6 sa sredstvom za alkiliranje s formulom (V) u kojoj su R2, R3, R4, R5, R6, X7, X8, X9 i X10 kako je definirano u bilo kojem od zahtjeva 1 do 6 i X predstavlja halogen ili odlazeću skupinu kao što je mesilat, triflat, nosilat ili tosilat
[image]
10. Postupak za dobivanje spojeva s formulom (I) prema bilo kojem od zahtjeva 1 do 6 naznačen time da sadrži funkcionalnu modifikaciju odgovarajućeg spoja formule (I) kao što je definirano u bilo kojem od zahtjeva 1 do 6.
11. Postupak prema bilo kojem od zahtjeva 8 do 10 naznačen time da dodatno obuhvaća dodatni korak izolacije željenog spoja.
12. Farmaceutski pripravak naznačen time da sadrži spoj s formulom (I) prema bilo kojem od zahtjeva 1 do 6 s farmaceutski prihvatljivim pomoćnim sredstvom.
13. Spoj prema bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu za liječenje i/ili sprječavanje bolesti povezane sa disfunkcijom H4 koja se bira od bolesti dišnih organa, kao što su respiratorne upalne bolesti, sindrom respiratornog distresa odraslih, akutni sindrom respiratornog distresa, bronhitis, kronični bronhitis, kronične opstruktivne plućne bolesti, cistične fibroze, astme, emfizema, rinitisa, kroničnog sinusitisa, alergije, alergijski induciranih reakcija dišnih puteva, alergijskog rinitisa, virusnog rinitisa, nealergijskog rinitisa, nesezonskog i sezonskog rinitisa, konjunktivitisa, nazalne kongestije, alergijske kongestije; poremećaja urogenitalnog trakta kao što su ženska i muška seksualna disfunkcija, stanja prekomjerno aktivnog mjehura, urinarne inkontinencije, hiperaktivnosti mjehura, benigne hiperplazije prostate i simptoma donjeg urinarnog trakta; dermatoloških bolesti kao što su dermatitis i psorijaza i tretmana svrbeža kože; bolesti kardiovaskularnog sustava, uključujući tromboembolijske bolesti, aterosklerozu, infarkt miokarda, anginu pektoris, ishemiju miokarda i aritmiju, bolesti začepljenja perifernih arterija, plućne embolije ili duboke venske tromboze, hipotenzije, plućne hipertenzije, maligne hipertenzije, srčane insuficijencije, zatajenja srca ili bubrega, moždanog udara i disfunkcije bubrega; bolesti probavnog sustava uključujući upalnu bolest crijeva, Crohnovu bolest, ulcerozni kolitis, alergije na hranu; autoimunih i upalnih bolesti, uključujući reumatoidni artritis, multiplu sklerozu; raka; boli; kronične hipereozinofilije; kronične bolesti povezanih s multipliciranjem mastocita; bolesti limfnog sustava.
14. Kombinacija spoja prema bilo kojem od zahtjeva 1 do 6 s jednim ili više terapeutskih sredstava koja se biraju iz skupa koji čine:
• antagonisti receptora histamina H1, H2 ili H3,
• antagonisti Leukotriena,
• inhibitori 5-Lipoksigenaze (5-LO) ili antagonisti aktivirajućeg proteina 5-lipoksigenaze (FLAP)
• CX1- i α2-adrenoceptorska agonistička vazokonstriktorska simpatomimetička sredstva za dekongestantnu uporabu
• ksantini, kao što su teofilin i aminofilin
• steroidni i ne-steroidni protuupalni lijekovi, kao što su natrijev kromoglikat i nedokromil natrij
• ketotifen
• inhibitori COX-1 (NSAID) i selektivni inhibitori COX-2
• imunosupresivi
• mukolitici ili sredstva protiv kašlja
15. Kombinacija prema zahtjevu 14, naznačena time da je antagonist H1 R odabran od cetirizina, desloratadina, bepotastina ili doksepina.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12305632.7A EP2671870A1 (en) | 2012-06-05 | 2012-06-05 | Novel (aza)benzhydryl ether derivatives, their process of preparation and their use as H4-receptor ligands for therapeutical applications |
| EP13170687.1A EP2671871B1 (en) | 2012-06-05 | 2013-06-05 | Novel (aza)benzhydryl ether derivatives, their process of preparation and their use as H4-receptor ligands for therapeutical applications |
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| HRP20170052T1 true HRP20170052T1 (hr) | 2017-05-05 |
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| HRP20170052TT HRP20170052T1 (hr) | 2012-06-05 | 2017-01-12 | Novi derivati (aza)benzhidril etera, njihov postupak dobivanja i njihova uporaba kao liganda h4-receptora za terapeutske primjene |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9242959B2 (hr) |
| EP (2) | EP2671870A1 (hr) |
| CY (1) | CY1118614T1 (hr) |
| DK (1) | DK2671871T3 (hr) |
| ES (1) | ES2606381T3 (hr) |
| HR (1) | HRP20170052T1 (hr) |
| HU (1) | HUE032870T2 (hr) |
| LT (1) | LT2671871T (hr) |
| PL (1) | PL2671871T3 (hr) |
| PT (1) | PT2671871T (hr) |
| RS (1) | RS55562B1 (hr) |
| SI (1) | SI2671871T1 (hr) |
| SM (1) | SMT201700032B (hr) |
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| CN104693183A (zh) * | 2015-03-23 | 2015-06-10 | 上海皓元化学科技有限公司 | 一种2-[(4-氯苯基)(4-哌啶基氧基)甲基]吡啶及其衍生物的合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2479843A (en) * | 1948-06-02 | 1949-08-23 | Nopco Chem Co | 1-alkylpiperidyl-4-benzhydryl ethers, acid salts thereof and their preparation |
| DE934890C (de) * | 1951-10-07 | 1955-11-10 | Chem Fab Promonta Ges Mit Besc | Verfahren zur Herstellung von basischen Benzhydrylaethern |
| US2745837A (en) * | 1954-01-21 | 1956-05-15 | Schering Corp | Benzhydryl ethers of alkyl piperidinols |
| GB780027A (en) * | 1955-01-20 | 1957-07-31 | Schering Corp | 3-piperidyl ethers and thioethers |
| US2974146A (en) * | 1956-02-24 | 1961-03-07 | Lakeside Lab Inc | 3-piperidyl benzhydryl ethers |
| US3280196A (en) * | 1962-05-25 | 1966-10-18 | S B Penick & Company | Benzhydryl-dihaloalkane ethers |
| HU196194B (en) * | 1986-04-28 | 1988-10-28 | Richter Gedeon Vegyeszet | Process for producing new 1-4 disubstituted piperazines and pharmaceuticals comprising the compounds |
| WO1997001340A1 (en) * | 1995-06-29 | 1997-01-16 | Mcneil-Ppc, Inc. | The combination of topical nasal antihistamines and topical nasal mast cell stabilizers |
| JP2006525299A (ja) * | 2003-05-01 | 2006-11-09 | ヴァーナリス リサーチ リミテッド | アゼチジンカルボキサミド誘導体及びｃｂ１レセプター媒介障害の治療におけるその使用 |
| TW200526637A (en) | 2003-09-30 | 2005-08-16 | Janssen Pharmaceutica Nv | Benzoimidazole compounds |
| WO2008105920A1 (en) * | 2007-02-28 | 2008-09-04 | Collegium Pharmaceutical, Inc. | Antihistamine combination |
| WO2009089234A2 (en) * | 2008-01-07 | 2009-07-16 | Auspex Pharmaceuticals | Substituted dibenzhydrylpiperazines |
| KR101146009B1 (ko) * | 2009-10-01 | 2012-05-15 | 동인화학 주식회사 | 광학 분리에 의한 활성 피페리딘 화합물의 제조방법 |
| EP2447263A1 (en) * | 2010-09-27 | 2012-05-02 | Bioprojet | Benzazole derivatives as histamine H4 receptor ligands |
-
2012
- 2012-06-05 EP EP12305632.7A patent/EP2671870A1/en not_active Withdrawn
-
2013
- 2013-06-05 RS RS20170013A patent/RS55562B1/sr unknown
- 2013-06-05 ES ES13170687.1T patent/ES2606381T3/es active Active
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- 2013-06-05 EP EP13170687.1A patent/EP2671871B1/en active Active
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- 2013-06-05 PL PL13170687T patent/PL2671871T3/pl unknown
- 2013-06-05 SI SI201330454A patent/SI2671871T1/sl unknown
- 2013-06-05 US US13/910,651 patent/US9242959B2/en active Active
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- 2013-06-05 DK DK13170687.1T patent/DK2671871T3/en active
-
2017
- 2017-01-12 HR HRP20170052TT patent/HRP20170052T1/hr unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| LT2671871T (lt) | 2016-12-27 |
| US9242959B2 (en) | 2016-01-26 |
| US20130324507A1 (en) | 2013-12-05 |
| ES2606381T3 (es) | 2017-03-23 |
| EP2671870A1 (en) | 2013-12-11 |
| SMT201700032B (it) | 2017-03-08 |
| RS55562B1 (sr) | 2017-05-31 |
| HUE032870T2 (en) | 2017-11-28 |
| EP2671871B1 (en) | 2016-10-19 |
| EP2671871A1 (en) | 2013-12-11 |
| PT2671871T (pt) | 2017-01-09 |
| SI2671871T1 (sl) | 2017-01-31 |
| PL2671871T3 (pl) | 2017-04-28 |
| DK2671871T3 (en) | 2017-01-16 |
| CY1118614T1 (el) | 2017-07-12 |
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