HRP20110670T1 - Derivati 4-(2-amino-1-hidroksietil)fenola kao agonisti beta-2 adrenergičkog receptora - Google Patents
Derivati 4-(2-amino-1-hidroksietil)fenola kao agonisti beta-2 adrenergičkog receptora Download PDFInfo
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- HRP20110670T1 HRP20110670T1 HR20110670T HRP20110670T HRP20110670T1 HR P20110670 T1 HRP20110670 T1 HR P20110670T1 HR 20110670 T HR20110670 T HR 20110670T HR P20110670 T HRP20110670 T HR P20110670T HR P20110670 T1 HRP20110670 T1 HR P20110670T1
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- Prior art keywords
- amino
- compound according
- hexyl
- difluoro
- phenol
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- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 title claims 2
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 title claims 2
- 239000000556 agonist Substances 0.000 title 1
- QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical class NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000000812 cholinergic antagonist Substances 0.000 claims 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- UAJBLLKKRKECAT-QFIPXVFZSA-N 4-[(1r)-2-[6-(2,2-difluoro-2-phenylethoxy)hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCC(F)(F)C=2C=CC=CC=2)=C1 UAJBLLKKRKECAT-QFIPXVFZSA-N 0.000 claims 1
- BTYJTZWUPACARF-DEOSSOPVSA-N 4-[(1r)-2-[[4,4-difluoro-6-(4-phenylbutoxy)hexyl]amino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCC(F)(F)CCOCCCCC=2C=CC=CC=2)=C1 BTYJTZWUPACARF-DEOSSOPVSA-N 0.000 claims 1
- QAEDBMVGNDMFDR-NRFANRHFSA-N 4-[(1r)-2-[[6-(2,2-difluoro-2-phenylethoxy)-4,4-difluorohexyl]amino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCC(F)(F)CCOCC(F)(F)C=2C=CC=CC=2)=C1 QAEDBMVGNDMFDR-NRFANRHFSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 229940091173 hydantoin Drugs 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
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- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C07C217/10—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
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- A61K31/47—Quinolines; Isoquinolines
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Abstract
Spoj formule (I): naznačen time, da: • R1 je skupina izabrana između -CH2OH. -NHC(O)H i• R2 je atom vodika; ili• R1 zajedno sa R2 formira skupinu -NH-C(O)-CH=CH- pri čemu je atom dušika vezan na atom ugljika u fenilnom prstenu koji sadrži R1 i atom ugljika je vezan na atom ugljika u fenilnom prstenu koji sadrži R2• R3 je izabran između atoma vodika i halogena ili skupina izabranih između -SO-R5, -SO2-R5, -NH-CO-NH2,
Claims (25)
1. Spoj formule (I):
[image]
naznačen time, da:
• R1 je skupina izabrana između -CH2OH. -NHC(O)H i
• R2 je atom vodika; ili
• R1 zajedno sa R2 formira skupinu -NH-C(O)-CH=CH- pri čemu je atom dušika vezan na atom ugljika u fenilnom prstenu koji sadrži R1 i atom ugljika je vezan na atom ugljika u fenilnom prstenu koji sadrži R2
• R3 je izabran između atoma vodika i halogena ili skupina izabranih između -SO-R5, -SO2-R5, -NH-CO-NH2, -CO-NH2, hidantoin, C1-4alkil, C1-4alkoksi i -SO2NR5R6.
• R4 je i zabran između atoma vodika, atoma halogena i C1-4alkil skupina
• R5 je C1-4alkil skupina ili C3-8cikloalkil
• R6 je neovisno izabran između atoma vodika i C1-4alkil skupina
• n, p i q su neovisno 0, 1, 2, 3 ili 4
• m i s su neovisno 0, 1, 2 ili 3
• r je 0, 1 ili 2
pod uvjetima da:
• barem jedno od m i r nije 0
• zbroj n+m+p+q+r+s je 7, 8, 9, 10, 11, 12 ili 13
• zbroj q+r+s je 2, 3, 4, 5 ili 6
ili njegove farmaceutski prihvatljive soli. solvati ili stereoizomeri.
2. Spoj u skladu sa patentnim zahtjevom 1 naznačen time, da barem jedno od m i r je 1.
3. Spoj u skladu sa patentnim zahtjevom 2 naznačen time, da zbroj m+r je 1.
4. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva, naznačen time, da zbroj n+m+p+q+r+s je 8, 9 ili 10.
5. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva naznačen time, da zbroj q+r+s je 2, 3 ili 4.
6. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva naznačen time, da s je cijeli broj izabran između 0 i 1.
7. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva naznačen time, da zbroj n+p je 4, 5 ili 6.
8. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva naznačen time, da zbroj q i s je 1, 2, 3 ili 4.
9. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva naznačen time, da R3 je atom vodika, atom halogena ili metil skupina.
10. Spoj u skladu sa patentnim zahtjevom 9 naznačen time, da R3 je atom klora ili fluora.
11. Spoj u skladu sa patentnim zahtjevom 9 naznačen time, da R3 je metil skupina.
12. Spoj u skladu sa bilo kojim od prethodnih patentnih zahtjeva naznačen time, da R4 je atom vodika.
13. Spoj u skladu sa bilo kojim patentnim zahtjevom 1 to 11 naznačen time, da R4 je atom klora.
14. Spoj u skladu sa patentnim zahtjevom 1, naznačen time, da je to spoj izabran iz skupine koja se sastoji od:
(R,S)-4-(2-{[6-(2,2-Difluoro-4-fenilbutoksi)heksil]amino}-1-hidroksi-etil)-2-(hidroksimetil)fenol
(R,S)-4-(2-{[6-(2,2-Difluoro-2-feniletoksi)heksil]amino}-1-hidroksi-etil)-2-(hidroksimetil)fenol
(R,S)-4-(2-{[4,4-Difluoro-6-(4-fenilbutoksi)heksil]amino}-1-hidroksi-eti])-2-(hidroksimetil)fenol
(R,S)-4-(2-{[6-(4,4-Difluoro-4-fenilbutoksi)heksil]amino}-1-hidroksi-etil)-2-(hidroksimetil)fenol
(R,S)-5-(2-{[6-(2,2-Difluoro-2-feniletoksi)heksil]amino}-1-hidroksi-etil)-8-hidroksikinolin-2(1H)-on
(R,S)-4-[2-({6-[2,2-Difluoro-2-(3-metilfenil)etoksi]heksil}amino)-1-hidroksietil]-2-(hidroksimetil)fenol
4-((1R)-2-{[6-(2,2-Difluoro-2-feniletoksi)heksil]amino}-1-hidroksietil)-2-(hidroksimetil)fenol
(R,S)-2-(Hidroksimetil)-4-(1-hidroksi-2-{[4,4,5,5-tetrafluoro-6-(3-fenilpropoksi)heksil]amino}etil)fenol
(R,S)-[5-(2-{[6-(2,2-Difluoro-2-feniletoksi)heksil]amino}-1-hidroksi-etil)-2-hidroksifenil]formamid
(R,S)-4-[2-({6-[2-(3-Bromofenil)-2,2-difluoroetoksi]heksil}amino)-1-hidroksietil]-2-(hidroksinietil)fenol
(R,S)-N-[3-(1,1-Difluoro-2-{[6-({2-hidroksi-2-[4-hidroksi-3-(hidroksimetil)fenil]etil}amino)heksil]oksi}etil)fenil]urea
(R,S)-3-[3-(1,1-difluoro-2{[6-({2-hidroksi-2-[4-hidroksi-3-(hidroksimetil)fenil]etil}amino)heksil]oksi}etil)fenil]imidazolidin-2,4-dion
(R,S)-4-[2-({6-[2,2-difluoro-2-(3-metoksifenil)etoksi]heksil}amino)-1-hidroksietil]-2-(hidroksimetil)fenol
5-((1R)-2-{[6-(2,2-difluoro-2-feniletoksi)heksil]amino}-1-hidroksietil)-B-hidroksikinolin-2(1H)-on
4-((1R)-2-{[4,4-Difluoro-6-(4-fenilbutoksi)heksil]amino}-1-hidroksi-etil)-2-(hidroksimetil)fenol
(R,S)-4-(2-{[6-(3,3-Difluoro-3-fenilpropoksi)heksil]amino}-1-hidroksietil)-2-(hidroksimetil)fenol
(R)-4-(2-{[6-(2,2-Difluoro-2-feniletoksi)-4,4-difluoroheksil]amino}-1-hidroksietil)-2-(hidroksimetil)fenol
(R,S)-4-(2-{[6-(2,2-difluoro-3-fenilpropoksi)heksil]amino}-1-hidroksietil)-2-(hidioksimetil)fenol hidroklorid
i njihovih farmaceutski prihvatljivih soli i solvata.
15. Spoj u skladu sa bilo kojim patentnim zahtjevom 1 do 14 naznačen time, da je za upotrebu u liječenju ljudi ili životinja.
16. Farmaceutski pripravak, naznačen time, da sadrži terapijski učinkovitu količinu spoja u skladu sa bilo kojim od patentnih zahtjeva 1 do 14 i farmaceutski prihvatljiv nosač.
17. Farmaceutski pripravak iz patentnog zahtjeva 16, naznačen time, da pripravak dodatno sadrži terapijski učinkovitu količinu jednog ili više drugih terapijskih sredstava.
18. Farmaceutski pripravak iz patentnog zahtjeva 17 naznačen time, da je drugo terapijsko sredstvo kortikosteroid, antikolinergijsko sredstvo ili inhibitor PDE4.
19. Farmaceutski pripravak u skladu sa bilo kojim patentnim zahtjevom 16 do 18, naznačen time, da je pripravak formuliran za primjenu udisanjem.
20. Kombinacija naznačena time, da se sastoji od spoja u skladu sa bilo kojim patentnim zahtjevom 1 do 14, i jednog ili više drugih terapijskih sredstava.
21. Kombinacija iz patentnog zahtjeva 20 naznačena time, da je drugo terapijsko sredstvo kortikosteroid, antikolinergijsko sredstvo ili inhibitor PDE4.
22. Spoj kako se definira u bilo kojem od patentnih zahtjeva 1 do 14 naznačen time, da se koristi u liječenju bolesti ili stanja u sisavaca povezanih s djelovanjem β2 adrenergičkih receptora.
23. Spoj u skladu sa patentnim zahtjevom 22 naznačen time, da bolest ili stanje izabrano iz skupine uključuje plućne bolesti, prijevremeni porod, glaukom. neurološke poremećaje, srčane poremećaje i upale.
24. Spoj u skladu sa patentnim zahtjevom 23 naznačen time, da plućna bolest je astma ili kronična opstruktivna plućna bolest.
25. Upotreba spoja u skladu sa bilo kojim od patentnih zahtjeva 1 do 14 naznačena time, da se koristi u proizvodnji lijeka za liječenje bolesti ili stanja kako je definirano u bilo kojem od patentnih zahtjeva 22 do 24.
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ES200501229A ES2265276B1 (es) | 2005-05-20 | 2005-05-20 | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
PCT/EP2006/004680 WO2006122788A1 (en) | 2005-05-20 | 2006-05-17 | DERIVATIVES OF 4-(2-AMINO-1-HYDROXYETHYL)PHENOL AS AGONISTS OF THE β2 ADRENERGIC RECEPTOR |
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HRP20110670T1 true HRP20110670T1 (hr) | 2011-10-31 |
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HR20110670T HRP20110670T1 (hr) | 2005-05-20 | 2011-09-16 | Derivati 4-(2-amino-1-hidroksietil)fenola kao agonisti beta-2 adrenergičkog receptora |
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ES (2) | ES2265276B1 (hr) |
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