HRP20201934T1 - Anti-fibrotički piridinoni - Google Patents
Anti-fibrotički piridinoni Download PDFInfo
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- HRP20201934T1 HRP20201934T1 HRP20201934TT HRP20201934T HRP20201934T1 HR P20201934 T1 HRP20201934 T1 HR P20201934T1 HR P20201934T T HRP20201934T T HR P20201934TT HR P20201934 T HRP20201934 T HR P20201934T HR P20201934 T1 HRP20201934 T1 HR P20201934T1
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- phenyl
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- 230000003510 anti-fibrotic effect Effects 0.000 title 1
- 150000005299 pyridinones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- -1 1-methyl pyrazolyl Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003176 fibrotic effect Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/4035—Isoindoles, e.g. phthalimide
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- A61K31/425—Thiazoles
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- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
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- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Claims (13)
1. Spoj koji ima strukturu formule (III):
[image]
ili njegova farmaceutski prihvatljiva sol, naznačeno time što
R1 je izabran iz grupe koja se sastoji od sljedećih: broma, fluora, metil izborno supstituiran sa jednim ili više R4, fenil izborno supstituiran sa jednim ili više R4, piridazinil izborno supstituiran sa jednim ili više R4 i pirazolil ili 1-metil pirazolil izborno supstituiran sa jednim ili više R4;
R3 je fenil izborno supstituiran sa jednim ili više R9;
prsten A je izabran od
[image]
[image]
svaki izborno supstituiran sa jednim ili više R4; i gdje je svaki R17 neovisno izabran od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C3-6 cikloalkil, izborno supstituirani C2-8 alkoksialkil, izborno supstituirani C-karboksi, acil, C6-10 aril izborno supstituiran sa jednim ili više R11, ili C7-14 aralkil izborno supstituiran sa jednim ili više R11;
svaki R4 je neovisno izabran iz grupe koja se sastoji od sljedećih: halogen, -CN, -OH, -C(O)R8, -SO2R16, izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil, izborno supstituirani C1-6 alkoksi, izborno supstituirani C6-10 aril izborno supstituiran sa jednim ili više R11, C7-14 aralkil izborno supstituiran sa jednim ili više R11, 5-10 -člani heteroaril izborno supstituiran sa jednim ili više R11, ili neovisno dva geminalna R4 zajedno su okso;
svaki R9 je neovisno izabran iz grupe koja se sastoji od sljedećih: cijana, fluora, klora, metila, etila, etoksi, metoksi, trifluorometil, trifluorometoksi i difluorometoksi;
R14 je izabran iz grupe koja se sastoji od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C6-10 aril i -C(O)R8;
R15 je izabran iz grupe koja se sastoji od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C6-10 aril i -C(O)R8;
svaki R8 je neovisno izabran iz grupe koja se sastoji od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil, C6-10 aril izborno supstituiran sa jednim ili više R11, C7-14 aralkil izborno supstituiran sa jednim ili više R11, -NR12R13 i -OR5;
svaki R12 je neovisno izabran iz grupe koja se sastoji od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil, C6-10 aril izborno supstituiran sa jednim ili više R11 i C7-14 aralkil izborno supstituiran sa jednim ili više R11;
svaki R13 je neovisno izabran iz grupe koja se sastoji od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil, C6-10 aril izborno supstituiran sa jednim ili više R11 i C7-14 aralkil izborno supstituiran sa jednim ili više R11;
svaki R5 je neovisno izabran iz grupe koja se sastoji od sljedećih: vodik, izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil, izborno supstituirani C2-8 alkoksialkil, C6-10 aril izborno supstituiran sa jednim ili više R11, C7-14 aralkil izborno supstituiran sa jednim ili više R11 i -(CH2)n-(3-10 -člani heterociklil) izborno supstituiran sa jednim ili više R10;
svaki R10 je neovisno izabran iz grupe koja se sastoji od sljedećih: izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil i izborno supstituirani C2-6 alkinil ili neovisno dva geminalna R10 zajedno su okso;
svaki R11 je neovisno izabran iz grupe koja se sastoji od sljedećih: halogen, -CN, izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil i izborno supstituirani C1-6 alkoksi;
svaki R16 je neovisno izabran iz grupe koja se sastoji od sljedećih: izborno supstituirani C1-6 alkil, izborno supstituirani C2-6 alkenil, izborno supstituirani C2-6 alkinil, C6-10 aril izborno supstituiran sa jednim ili više R11, C7-14 aralkil izborno supstituiran sa jednim ili više R11, -NR12R13 i -OR5;
Z je kisik;
svaki n je neovisno cijeli broj od 0 do 4; i
veze predstavljene punom i isprekidanom linijom su neovisno izabrane iz grupe koja se sastoji od jednostruke veze i dvostruke veze, uz uvjet kada je prsten A izabran od izborno supstituiranog pirolila ili izborno supstituiranog dihidropirolidinila, R3 je fenil izborno supstituiran sa jednim ili više R9, i Z je O;
tada R1 nije bromo, fluoro, 3-metoksi fenil ili 3,5-dimetoksi fenil;
kada je prsten A piridil, R1 je izborno supstituirani fenil, i Z je O; tada R3 nije halogenom supstituirani fenil;
kada je prsten A izborno supstituirani pirimidil, R3 je fenil i Z je O; tada R1 nije metil;
kada je prsten A izborno supstituirani furanil, R3 je fenil izborno supstituiran sa jednim ili više R9, i Z je O; tada R1 nije fluoro;
kada je prsten A izborno supstituirani pirolil, R3 je fenil izborno supstituiran sa jednim ili više R9, i Z je O; tada R1 nije metil;
kada je prsten A tetrahidrofuranil, R3 je fenil, i Z je O; tada R1 nije metil ili fenil; i
kada je prsten A piradizinil, R3 je 4-NO2-fenil, i Z je O; tada R1 nije metil.
2. Spoj prema patentnom zahtjevu 1, naznačen time što R1 je izabran od fenila, piridazinila, pirazolila ili 1-metil pirazolila, od kojih je svaki izborno supstituiran sa jednim ili više R4.
3. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time što prsten A je izabran od
[image]
svaki je izborno supstituiran sa jednim ili više R4.
4. Spoj prema patentnom zahtjevu 3, naznačen time što R17 je izabran od vodika, metila, etila, izopropila, ciklopropila, -(CH2)2F, -(CH2)2OH, -(CH2)2OCH3, -(CH2)2OC2H5, -(CH2)2OC3H7, -C(O)O-t-Bu, -C(O)CH3 ili benzila.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time što R4 je izabran od halogena, izborno supstituiranog C1-6 alkila ili C7-14 aralkila izborno supstituiranog sa jednim ili više R11, ili dva geminalna R4 zajedno su okso.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što, veze predstavljene punom i isprekidanom linijom u formuli (III) su dvostruke veze, uz uvjet da kada je prsten A jednak
[image]
jedna od veza predstavljena punom i isprekidanom linijom je jednostruka veza.
7. Spoj prema patentnom zahtjevu 1, naznačen time što spoj je izabran iz grupe koja se sastoji od spoja 29-63, 392-400, 568, 569, 571-574, 577, 579-584, 586-589, 591-594, 596-608, 614, 615, 617, 619, 620, 624-626, 631, 634-636, 640, 642-654, 657-661, 665, 669-687 i 689-695 kao što su prikazani u donjoj tabeli, ili njihovih farmaceutski prihvatljivih soli.
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8. Spoj strukture
[image]
ili njegova farmaceutski prihvatljiva sol.
9. Spoj strukture
[image]
ili njegova farmaceutski prihvatljiva sol.
10. Spoj strukture
[image]
ili njegova farmaceutski prihvatljiva sol.
11. Spoj strukture
[image]
ili njegova farmaceutski prihvatljiva sol.
12. Farmaceutski pripravak koji sadrži efikasnu količinu spoja prema bilo kojem od patentnih zahtjeva 1 do 11 ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljiv nosač, razblaživač, ekscipijent ili njihovu kombinaciju.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11, njegova farmaceutski prihvatljiva sol, ili farmaceutski pripravak prema patentnom zahtjevu 12 za uporabu u liječenju fibrotičkog stanja.
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US201261709075P | 2012-10-02 | 2012-10-02 | |
US201361777499P | 2013-03-12 | 2013-03-12 | |
US201361872157P | 2013-08-30 | 2013-08-30 | |
EP13843717.3A EP2903991B1 (en) | 2012-10-02 | 2013-10-01 | Anti-fibrotic pyridinones |
PCT/US2013/062910 WO2014055548A1 (en) | 2012-10-02 | 2013-10-01 | Anti-fibrotic pyridinones |
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