HRP20141051T1 - Fluorirani derivati 3-hidroksipiridin-4-ona - Google Patents
Fluorirani derivati 3-hidroksipiridin-4-ona Download PDFInfo
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- HRP20141051T1 HRP20141051T1 HRP20141051AT HRP20141051T HRP20141051T1 HR P20141051 T1 HRP20141051 T1 HR P20141051T1 HR P20141051A T HRP20141051A T HR P20141051AT HR P20141051 T HRP20141051 T HR P20141051T HR P20141051 T1 HRP20141051 T1 HR P20141051T1
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- LQUSVSANJKHVTM-UHFFFAOYSA-N 3-hydroxy-3h-pyridin-4-one Chemical class OC1C=NC=CC1=O LQUSVSANJKHVTM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 46
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 42
- -1 1-2-4-triazolyl Chemical group 0.000 claims 22
- 125000004193 piperazinyl group Chemical group 0.000 claims 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 10
- 125000003386 piperidinyl group Chemical class 0.000 claims 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 claims 5
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 4
- 125000003275 alpha amino acid group Chemical group 0.000 claims 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 4
- 125000002757 morpholinyl group Chemical class 0.000 claims 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 229910052742 iron Inorganic materials 0.000 claims 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical class N1(CCOCC1)* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 231100000816 toxic dose Toxicity 0.000 claims 2
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
- 208000024412 Friedreich ataxia Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
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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
- C07D213/04—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
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
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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
- C07D213/04—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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- 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
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- 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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- 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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- 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
- C07D213/04—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
- 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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- C07D213/04—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
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Claims (47)
1. Spoj formule I:
[image]
gdje je
G1 H, C1-C4 alkil, CH2OH, CH2NR1R2, CH(R4)CF3, CH(R7)CF2H, NR1R2 ili
[image]
G2 je H, C1-C4 alkil, ciklopropil ili (CH2)nCF2R3;
G3 je H, C1-C4 alkil, CH2OH, CH2NR1R2, CH(R6)CF3, CH2-A-OH, CH2-A-NHR9 ili CH2CF3 ili
[image]
i
G4 je H, C1-C4 alkil, halogen ili CH(R8)CF3;
n je 1, 2 ili 3;
R1 i R2 su ili (a) dve nezavisne grupe ili (b) zajedno formiraju pojedinačnu grupu na prstenu; R1 i R2 kao nezavisne grupe, nezavisno se i biraju iz grupe koju čine: H, C1-C4 alkil, C3-C6 cikloalkil, alil i propargil; R1 i R2 kada formiraju pojedinačnu grupu na prstenu, nezavisno se biraju iz grupe koju čine: piperazinil, N-(C1-C4 alkil)-supstituirani piperazinil, morfolinil i piperidinil;
R3 je H ili F;
R4 i R7 se nezavisno biraju iz grupe koju čine: H, OH, NR1R2, imidazolil, 1-2-4-triazolil, piperazinil, N-C1-C4 alkilpiperazinil, N-benzilpiperazinil, N-fenilpiperazinil, 2-piridilpiperazinili-A-NH-R10; i kada su R4 i R7 imidazolil, 1-2-4-triazolil, piperazinil, N-C1-C4 alkilpiperazinil, N-benzilpiperazinil, N-fenilpiperazinil, 2-piridilpiperazin ili-A-NH-R10 mjesto vezivanja R4 ili R7 za CH ostatak na G je N atom R4 ili R7;
R5 je C1-C4 alkil;
R6 je H ili OH;
R8 je izabran iz grupe koju čine: NR1R2, imidazolil, 1-2-4-triazolil, piperazinil, N-C1-C4 alkilpiperazinil, N benzilpiperazinil, N-fenilpiperazinil, 2-piridilpiperazinil i -A-NH-R10;i kada je R8 imidazolil, 1-2-4-triazolil, piperazinil, N-C1-C4 alkilpiperazinil, N-benzilpiperazinil, N-fenilpiperazinil, 2-piridilpiperazinilili-A-NH-R10, mjesto vezivanja R8 za CH ostatak na G4 je atom dušika na R8;
R9 i R10 su nezavisni H ili C1-C4 alkil;
A je -NH-(CH2)m-CO- ili ostatak alfa aminokiseline; m je 1, 2 ili 3;i omogućavaju da:
Najmanje jedan od G1, G2, G3 i G4 obuhvaća barem jedan fluoridni ostatak;
kada je G1CH(R4)CF3 i kada je R4H ili OH, onda je ili (i) G3 CH2NR1R2, CH2-A-OH, CH2-A-NHR9 ili je (ii) G4 halogen ili CH(NR1R2)CF3; i kada je G3 CH(R6)CF3, onda je G1 CH2NR1R2,CH(R4)CF3,CH(R7)CF2, H, NR1R2 ili
[image]
2. Spoj iz zahtjeva 1 gdje, kada je G1 CH(NR1R2)CF3 onda su G3 i G4 nezavisni H ili C1-C4 alkil i G2 je H, C1-C4 alkil ili ciklopropil.
3. Spoj iz zahtjeva 1 ili 2 gdje:
a) kada je G2(CH2)nCF2R3 onda su G1 i G3 nezavisno H, C1-C4 alkil, CH2OH ili CH2NR1R2; ili
b) kada je G2 H onda je G4 H ili C1-C4 alkil.
4. Spoj bilo kojeg od zahtjeva od 1 do 3 gdje:
a) Kada je G3
[image]
onda su G1 i G4 nezavisni H ili C1-C4 alkil; ili
b) kada je G3 CH2CF3 onda je G1NR1R2.
5. Spoj iz bilo kojeg od zahtjeva od 1 do 4 gdje:
a) kada je G1 CH2NR1R2 onda je G2(CH2)nCF2R3; ili
b) kada je G1 CH(R7)CF2H onda su G3 i G4 nezavisni H ili C1-C4 alkil i G2 je C1-C4 alkil ili ciklopropil; ili
c) kada je G1 CH(R4)CF3 onda je G2 C1-C4 alkil ili ciklopropil; omogućavaju da kada je R4 H ili OH onda je G3 CH2 NR1R2, CH2-A-OH, CH2-A-NHR9; ili
d) kada je G1 CH(R4)CF3 i kada je R4 H ili OH onda je G4 halogen; ili
e) kada su G1 ili G3 CH2OH onda je G2 (CH2)nCF2R3; ili
f) kada je G1 NR1R2 onda je G3 CH2CF3, G4 je H ili C1-C4 alkil i G2 je C1-C4 alkil ili ciklopropil.
6. Spoj iz bilo kojeg od zahtjeva od 1 do 5 gdje kada je G4 CH(R8)CF3 onda su G1 i G3 nezavisni H ili C1-C4 alkil i G2 je vodik, C1-C4 alkil ili ciklopropil.
7. Spojevi iz bilo kojeg od zahtjeva od 1 do 6 gdje:
a) kada je G3 CH2-A-OH ili CH2-A-NHR onda je G4 H ili C1-C4 alkil, G2 je C1-C4 ciklopropil i G1 je CH(R4)CF3 gdje je R4 H ili OH; ili
b) kada je G3 CH2NR1R2 i kada je G2 C1-C4 alkil ili ciklpropil onda je G4 H ili C1-C4 alkil i G1 je CH(R4)CF3 ili gdje je R4 H ili OH.
8. Spoj iz bilo kojeg od zahtjeva od 1 do 7 gdje kada je G1CH(R4)CF3 i kada je R4 H ili OH onda je ili G3 CH2NR1R2 ili je G4 halogen.
9. Spoj iz bilo kojeg od zahtjeva od 1 do 8 gdje kada je G3 CH(R6)CF3 onda je G1 CH2NR1R2 ili NR1R2.
10. Spoj iz zahtjeva 1 gdje
G1 je H , C1-C4 alkil, -CH2OH ili -CH2NR1R2;
G2 je (CH2)n-CF2R3;
G3 je H, C1-C4 alkil, -CH2OH ili -CH2NR1R2;
G4 je H , C1-C4 alkil ili halogen;
R1 i R2 su ili (a) dve nezavisne grupe ili (b) zajedno formiraju pojedinačnu grupu na prstenu; R1i R2 kao nezavisne grupe, uključujući i dušik za koji su vezane biraju se iz grupe koju čine: H, C1-C4 alkil,C3-C6 alkil, alil i propargil;
R1 i R2 kada su nezavisne grupe na prstenu, nezavisno se biraju iz grupe koju čine: piperazinil, N-(C1-C4 alkil)-supstituirani piperazinil, morfolinil i piperidinil;
n je 1,2 ili 3;
R3 je H ili F;
11. Spoj iz zahtjeva 10 gdje je n jednako 1.
12. Spoj iz zahtjeva 11 gdje je G4 H.
13. Spoj iz zahtjeva 12 gdje je R3 H.
14. Spoj iz zahtjeva 12 gdje je R3 F.
15. Spoj iz zahtjeva 14 gdje je:
a) G1 vodik i G3 je metil; ili
b) G1 metil i G3 je H; ili
c) G1 etil i G3 H; ili
d) G1 je H i G3 H; ili
e) G1 je -CH2OH i G3 je H; ili
f) G1 je -CH2NMe2, i G3 je metil; ili
g) G1 je -CH2NMe2 i G3 je H; ili
h) G1 je -CH2OH i G3 je metil; ili
i) G1 je
[image]
i G3 je metil.
16. Spoj iz zahtjeva 13 gdje je:
a) G1 je metil i G3 je H; ili
b) G1 je H i G3 je metil; ili
c) G1 je -CH2NMe2 i G3 je metil.
17. Spojevi iz zahtjeva 1 gdje je:
G1-CH(R4)CF3;
G2 je H, C1-C4 alkil ili ciklopropil;
G3 je H, C1-C4 alkil, CH2-A-OH, CH2-A-NHR9 ili CH2NR1R2;
G4 je H, C1-C4 alkil ili halogen;
R4 se bira iz grupe koju čine: H,OH,NR1R2, imidazol, 1,2,4-triazol, piperazin, N-C1-C4 alkilpiperazin, N-benzilpiperazin, N-fenilpiperazin, 2-piridilpiperazin i -A-NH-R10; i kada je R4 NR1R2, imidazol, 1,2,4-triazol, piperazin, N-C1-C4 alkilpiperazin, N-benzilpiperazin, N-fenilpiperazin, 2-piridilpiperazin ili -A-NH-R10, mjesto vezivanja R4 za -CH ostatak na G1 je N-atom R4;
R1 i R2 su ili (a) dve nezavisne grupe ili (b) zajedno formiraju pojedinačnu grupu na prstenu; R1 i R2 kao nezavisne grupe, nezavsno se i biraju iz grupe koju čine: H,C1-C4 alkil,C3-C6 cikloalkil, alil i propargil;
R1 i R2 kada formiraju pojedinačnu grupu na prstenu, nezavisno se biraju iz grupe koju čine: piperazinil, N-(C1-C4 alkil)-supstituirani piperazinil, morfolinil i piperidinil;
A je -NH-(CH2)m-CO-i li ostatak alfa aminokiseline;
m je 1,2 ili 3; i
R9 i R10 su nezavisno H ili C1-C4 alkil.
18. Spoj iz zahtjeva 17 gdje je G2 C1-C4 alkil ili ciklopropil; G3 je H ili C1-C4 alkil; i R4 izabrano je iz grupe koju čine: NR1R2, imidazol, 1,2,4-triazol, piperazin, N-C1-C4 alkilpiperazin, N-benzilpiperazin, N-fenilpiperazin, 2-piridilpiperazin i -A-NH-R10.
19. Spoj iz zahtjeva 18 gdje je G2 metil.
20. Spoj iz zahtjeva 19 gdje je G3 H i G4 je H.
21. Spoj iz zahtjeva 20 gdje je R4 NR1R2.
22. Spoj iz zahtjeva 20 gdje je R4A-NHR10; A je D-alanil i R10 je metil.
23. Spoj iz zahtjeva 21 gdje je:
a) R1 je metil i R2 je metil; ili
b) R1 je metil i R2 je propargil; ili
c) R1 je H i R2 je ciklopropil; ili
d) R1 je H i R2 je alil; ili
e) NR1R2 je piperidinil; ili
f) NR1R2 je N-metilpiperazinil.
24. Spoj iz zahtjeva 17 gdje je G3 CH2-A-OH, CH2-A-NHR9 ili CH2NR1R2; G4 je H ili C1-C4 alkil; i R4 je H ili OH.
25. Spoj iz zahtjeva 24 gdje je G2 metil.
26. Spoj iz zahtjeva 25 gdje je G4 H.
27. Spoj iz zahtjeva 26 gdje je:
a) G3 je CH2NR1R2; R1je metil; R2 je metil; i R4 je H; ili
b) G3 je CH2NR1R2 ;R1 je metil; R2 je metil; i R4 je OH; ili
c) G3 je CH2-A-OH; A je L-alanil;i R4 je OH; ili
d) G3 je CH2-A-NHR9; A je L-alanil; R9 je metil; i R4 je OH.
28. Spoj iz zahtjeva 17 gdje je G3 H ili C1-C4 alkil; i G4 je halogen.
29. Spoj iz zahtjeva 28 gdje je G2 metil.
30. Spoj iz zahtjeva 29 gdje je G4 klor.
31. Spoj iz zahtjeva 30 gdje je:
a) G3 je metil; i R4 je OH; ili
b) G3 je metil; i R4 je H; ili
c) G3 je metil; R4 je NR1R2; R1 je metil; i R2 je metil; ili
d) G3 je H; R4 je NR1R2; R1 je metil; i R2 je metil; ili
e) G3 je H; R4 je NR1R2; i NR1R2je piperidinil; ili
f) G3 je H; i R4 je H.
32. Spoj iz zahtjeva 1 gdje
G1 je H ili C1-C4 alkil;
G2 je H, C1-C4 alkil ili ciklopropil;
G3 je H ili C1-C4 alkil;
G4 je -CH(CF3)(R8);
R8 izabran je iz grupe koju čine: NR1R2, imidazol, 1,2,4-triazol, piperazin, N-C1-C4 alkilpiperazin, N-benzilpiperazin, N-fenilpiperazin, 2-piridilpiperazin i-A-NH-R10; mjesto vezivanja R8 za –CH ostatak na G1 je na N-atomu R8;
R1 i R2 su ili (a) dve nezavisne grupe ili (b) zajedno formiraju pojedinačnu grupu na prstenu;
R1 i R2 kao nezavisne grupe, nezavisno se i biraju iz grupe koju čine: H, C1-C4 alkil, C3-C6 cikloalkil, alil i propargil; R1 i R2 kada formiraju pojedinačnu grupu na prstenu, nezavisno se biraju iz grupe koju čine: piperazinil, N-(C1-C4 alkil)-supstituirani piperazinil, morfolino i piperidinil;
A je -NH-(CH2)m-CO- ili ostatak alfa aminokiseline;
m je 1,2 ili 3; i R10 je H ili C1-C4 alkil.
33. Spoj iz zahtjeva 32 gdje je G3 H.
34. Spoj iz zahtjeva 33 gdje je G1 metil.
35. Spoj iz zahtjeva 34 gdje :
a) G2 je H; R8 je -A-NH-R10; A je L-alanil; i R10 je metil; ili
b) G2 je metil; R8 je NR1R2; R1 je metil i R2 je metil; ili
c) G2 je metil; R8 je NR1R2; R1 je H i R2 je metil; ili
d) G2 je metil; R8 je NR1R2; i NR1R2 je piperidinil; ili
e) G2 je metil; R8 je NR1R2; i NR1R2 je imidazolil; ili
f) G2 je metil; R8 je NR1R2; i NR1R2je N-metilpiperazinil.
36. Spojevi iz zahtjeva 1 gdje je
G1 CH2NR1R2 ili NR1R2;
G2 je C1-C4 alkil ili ciklopropil; G3 je -CH(CF3)(R6);
G4 je H ili C1-C4 alkil; R6 je H ili OH; i
R1 i R2 su ili (a) dve nezavisne grupe ili (b) zajedno formiraju pojedinačnu grupu na prstenu uključujući i N za koji su vezane;
R1 i R2 kao nezavisne grupe, nezavisno se i biraju iz grupe koju čine: H, C1-C4 alkil, C3-C6 cikloalkil, alil i propargil;
R1 i R2 kada skupa formiraju pojedinačnu grupu na prstenu uključujući i N za koji su vezane, nezavisno se biraju iz grupe koju čine: piperazinil, N-(C1-C4 alkil)-supstituirani piperazinil, morfolinil i piperidinil;
37. Spojevi iz zahtjeva 36 gdje je G4 H.
38. Spojevi iz zahtjeva 37 gdje je G2 metil.
39. Spojevi iz zahtjeva 38 gdje je:
a) G1 je NR1R2; R1 je metil; R2 je metil; i R6 je H; li
b) G1 je CH2 NR1R2; R1 je metil; R2je metil; i R6 je OH.
40. Spojevi iz zahtjeva 1 gdje je G1-CH (CF2H)(R7);
G2 je H, C1-C4 alkil ili ciklopropil;
G3 je H ili C1-C4 alkil; G4 je H ili C1-C4 alkil;
R7 je izabran iz grupe koju sadrže: H, OH, NR1R2, imidazolil, 1,2,4-triazolil, piperazinil, N-C1-C4 alkilpiperazinil, N-benzilpiperazinil, N-fenilpiperazinil, 2-piridilpiperazinil i –CH2-A-NH-R10; i kada je R7 NR1R2, imidazolil, 1,2,4-triazolil,piperazinil, N-C1-C4 alkilpiperazinil, N-benzilpiperazinil, N-fenilpiperazinil, 2-piridilpiperazinil ili -CH2-A-NH-R10 mjesto vezivanja R7 za -CH ostatak na G1 je na N-atomu R7;
R1 i R2 su ili (a) dve nezavisne grupe ili (b) zajedno formiraju pojedinačnu grupu na prstenu uključujući i N za koji su vezane;
R1 i R2 kao nezavisne grupe, nezavisno se i biraju iz grupe koju čine: H, C1-C4 alkil,C3-C6 cikloalkil, alil i propargil; R1 i R2 kada formiraju pojedinačnu grupu na prstenu uključujući i N za koji su vezane, nezavisno se biraju iz grupe koju čine: piperazinil, N-(C1-C4 alkil)-supstituirani piperazinil, morfolino i piperidinil;
A je -NH-(CH2)m-CO- ili ostatak alfa aminokiseline;
m je 1, 2 ili 3;i R10 je H, C1-C4 alkil.
41. Spojevi iz zahtjeva 40 gdje je:
a) G2 je metil, G3 je H, G4 je H i R7 je OH; ili
b) G2 je metil, G3 je H, G4 je H i R7 je H.
42. Spojevi iz zahtjeva 1 gdje je G1 C(R5)(R6)(CF3)
G2 je H, C1-C4 alkil ili ciklopropil;
G3 je H ili C1-C4 alkil; i
G4 je H ili C1-C4 alkil.
43. Spojevi iz zahtjeva 42 gdje je G2 metil; G3 je H; G4 je H; R5 je metil; i R6 je H ili OH.
44. Spojevi iz zahtjeva 43 gdje je R6 OH.
45. Spoj iz bilo kojeg od zahtjeva od 1 do 44 za uporabu u tretmanu oboljenja vezanih za toksičnu koncentraciju željeza.
46. Uporaba spojeva prema bilo kojem od zahtjeva od 1 do 44 za pripremu lijeka za tretman oboljenja vezanih za toksičnu koncentraciju željeza.
47. Spoj iz zahtjeva 45 ili upotreba prema zahtjevu 46 gdje je medicinsko stanje vezano za toksičnu koncentraciju željeza izabrano iz grupe oboljenja koja se sastoji od: raka, plućnih bolesti, progresivne bolesti bubrega i Friedreichove ataksije.
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| US22297909P | 2009-07-03 | 2009-07-03 | |
| PCT/CA2010/001027 WO2011000104A1 (en) | 2009-07-03 | 2010-07-05 | Fluorinated derivatives of 3-hydroxypyridin-4-ones |
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Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2918402A (en) | 1958-07-29 | 1959-12-22 | Dodge Chem Co | Bactericidal-fungicidal compositions |
| NL300788A (hr) | 1962-12-20 | |||
| CA1095921A (en) | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
| GB8308054D0 (en) * | 1983-03-24 | 1983-05-05 | Hider R C | Pharmaceutical compositions |
| GB8308055D0 (en) * | 1983-03-24 | 1983-05-05 | Hider R C | Pharmaceutical compositions |
| USRE34313E (en) | 1983-09-23 | 1993-07-13 | National Research Development Corporation | Pharmaceutical compositions |
| GB8325496D0 (en) | 1983-09-23 | 1983-10-26 | Hider R C | Pharmaceutical compositions |
| GB8329043D0 (en) * | 1983-10-31 | 1983-11-30 | Hider R C | Pharmaceutical compositions |
| JPH01305081A (ja) | 1988-04-04 | 1989-12-08 | E R Squibb & Sons Inc | ３―アシルアミノ―１―［［［（置換スルホニル）アミノ〕カルボニル〕アミノ〕―２―アゼチジノン類 |
| DE3826846A1 (de) * | 1988-08-06 | 1990-02-08 | Goedecke Ag | Alkoxy-4(1h)-pyridon-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel |
| JPH0714872B2 (ja) | 1990-02-06 | 1995-02-22 | 昭和薬品化工株式会社 | シロップ剤組成物 |
| GB9100465D0 (en) | 1991-01-09 | 1991-02-20 | Hider Robert C | Pharmaceutical compositions |
| US5624807A (en) | 1992-07-22 | 1997-04-29 | The Mclean Hospital Corporation | Methods for detecting Alzheimer's disease by measuring ratios of calcium-activated neutral protease isoforms |
| EP0620001A1 (en) | 1993-04-16 | 1994-10-19 | McNEIL-PPC, INC. | Aqueous pharmaceutical suspension and process for preparation thereof |
| EP0741717A1 (en) | 1994-01-31 | 1996-11-13 | Cultor Ltd. | Method of synthesizing gamma pyrones |
| EP0754039A4 (en) | 1994-04-08 | 2002-07-17 | Procter & Gamble | METHODS OF USING IRON-CONTAINING CHELATES TO REDUCE MAMMALIAN FREE RADICAL DAMAGES |
| AU3154895A (en) | 1994-08-01 | 1996-03-04 | Kv Pharmaceutical Corporation | Tastemasked liquid pharmaceutical delivery system |
| US5616621A (en) | 1995-01-30 | 1997-04-01 | American Home Products Corporation | Taste masking liquids |
| JPH0925234A (ja) | 1995-07-12 | 1997-01-28 | Wakunaga Pharmaceut Co Ltd | 脳疾患改善剤 |
| ES2244967T3 (es) * | 1995-09-29 | 2005-12-16 | Novartis Ag | Nuevas hidroxipiridinonas. |
| US5763449A (en) | 1996-08-07 | 1998-06-09 | Ascent Pediatrics, Inc. | Pleasant-tasting aqueous liquid composition of a bitter-tasting drug |
| GB9711093D0 (en) | 1997-05-29 | 1997-07-23 | British Tech Group | Novel orally active iron (III) chelators |
| KR100746753B1 (ko) | 1998-08-28 | 2007-08-06 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 고미 등을 경감한 의약조성물 |
| US6472378B2 (en) | 1998-08-31 | 2002-10-29 | Pro-Neuron, Inc. | Compositions and methods for treatment of mitochondrial diseases |
| US6133322A (en) | 1998-10-29 | 2000-10-17 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Quinone derivatives for treating or preventing diseases associated with iron overload |
| US6933104B1 (en) | 1999-04-23 | 2005-08-23 | Shiva Biomedical, Llc | Diagnosis and treatment of human kidney diseases |
| IL130324A0 (en) | 1999-06-07 | 2000-06-01 | Yeda Res & Dev | Pharmaceutical compositions comprising iron chelators for the treatment of neurodegenerative disorders and some novel iron chelators |
| AUPQ262499A0 (en) | 1999-09-02 | 1999-09-23 | University Of Queensland, The | Novel iron chelators |
| CA2313270C (en) | 2000-06-30 | 2011-09-13 | Apotex Inc. | Use of deferiprone in treating and preventing iron-induced cardiac disease |
| BR0207930A (pt) | 2001-03-05 | 2004-03-02 | Ortho Mcneil Pharm Inc | Composições farmacêuticas lìquidas com sabor mascarado |
| WO2003075910A1 (en) | 2002-03-08 | 2003-09-18 | Protemix Corporation Limited | Preventing and/or treating vascular disease, cardiomyopathy and/or associated heart failure |
| JP4619658B2 (ja) | 2002-03-12 | 2011-01-26 | 富山化学工業株式会社 | 快い味の経口懸濁液および方法 |
| WO2004006856A2 (en) * | 2002-07-12 | 2004-01-22 | The Buck Institute For Research On Aging | Iron sequestration or elimination to reduce neurodegeneration or parkinsons disease progression |
| CA2505476C (en) | 2002-11-07 | 2015-05-26 | Technion Research And Development Foundation Ltd. | Neuroprotective iron chelators and pharmaceutical compositions comprising them |
| DE10336497B4 (de) | 2003-08-08 | 2007-04-05 | Freie Universität Berlin | Substituierte Pyridine und ein Verfahren zur Herstellung von substituierten Pyridinen |
| BRPI0509592A (pt) | 2004-05-06 | 2007-09-25 | Cydex Inc | formulações de sabor mascarado, contendo sertralina e ciclodextrina de éter de sulfoalquila |
| US8829051B2 (en) | 2004-05-24 | 2014-09-09 | Geoffrey C. GURTNER | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| US9737511B2 (en) | 2004-05-24 | 2017-08-22 | Geoffrey C. GURTNER | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| US7728038B2 (en) | 2004-08-04 | 2010-06-01 | University Of Utah Research Foundation | Methods for chelation therapy |
| US20060093630A1 (en) | 2004-10-29 | 2006-05-04 | Buehler Gail K | Dye-free pharmaceutical suspensions and related methods |
| US20070197469A1 (en) | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V | Fluoroquinolone carboxylic acid salt compositions |
| DK1991225T3 (da) | 2006-02-22 | 2013-12-16 | Apotex Technologies Inc | Anvendelse af deferipron og fremgangsmåder til at behandle og/eller forebygge Friedreichs ataksi, der resulterer af intracellulær fejlhåndtering af jern |
| WO2008116301A1 (en) | 2007-03-28 | 2008-10-02 | Apotex Technologies Inc. | Fluorinated derivatives of deferiprone |
| GB0803019D0 (en) * | 2008-02-19 | 2008-03-26 | Btg Int Ltd | Fluorinated compounds |
| WO2009129592A1 (en) | 2008-04-25 | 2009-10-29 | Apotex Technologies Inc. | Liquid formulation for deferiprone with palatable taste |
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- 2010-07-05 WO PCT/CA2010/001027 patent/WO2011000104A1/en active Application Filing
- 2010-07-05 DK DK10793481.2T patent/DK2448922T3/da active
- 2010-07-05 UA UAA201201057A patent/UA108076C2/ru unknown
- 2010-07-05 CN CN201080038314.0A patent/CN102712591B/zh not_active Expired - Fee Related
- 2010-07-05 CA CA2767130A patent/CA2767130C/en not_active Expired - Fee Related
- 2010-07-05 SI SI201030795T patent/SI2448922T1/sl unknown
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2011
- 2011-12-29 TN TNP2011000678A patent/TN2011000678A1/en unknown
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2012
- 2012-01-03 CL CL2012000009A patent/CL2012000009A1/es unknown
- 2012-01-03 IL IL217349A patent/IL217349A/en not_active IP Right Cessation
- 2012-01-05 NI NI201100225A patent/NI201200004A/es unknown
- 2012-01-31 ZA ZA2012/00751A patent/ZA201200751B/en unknown
- 2012-02-03 EC ECSP12011648 patent/ECSP12011648A/es unknown
- 2012-11-09 HK HK12111353.4A patent/HK1173139A1/xx not_active IP Right Cessation
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2014
- 2014-10-09 CY CY20141100818T patent/CY1115632T1/el unknown
- 2014-10-30 HR HRP20141051AT patent/HRP20141051T1/hr unknown
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2015
- 2015-06-10 US US14/735,718 patent/US9550733B2/en not_active Expired - Fee Related
- 2015-06-11 US US14/736,536 patent/US20150274665A1/en not_active Abandoned
- 2015-12-01 US US14/956,029 patent/US20160083346A1/en not_active Abandoned
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2016
- 2016-12-08 US US15/372,497 patent/US9938240B2/en active Active
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2017
- 2017-05-12 US US15/594,048 patent/US20170247329A1/en not_active Abandoned
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