HRP20130846T1 - Derivati indolizina i njihova uporaba u medicinske svrhe - Google Patents
Derivati indolizina i njihova uporaba u medicinske svrhe Download PDFInfo
- Publication number
- HRP20130846T1 HRP20130846T1 HRP20130846AT HRP20130846T HRP20130846T1 HR P20130846 T1 HRP20130846 T1 HR P20130846T1 HR P20130846A T HRP20130846A T HR P20130846AT HR P20130846 T HRP20130846 T HR P20130846T HR P20130846 T1 HRP20130846 T1 HR P20130846T1
- Authority
- HR
- Croatia
- Prior art keywords
- cyano
- alkyl
- group
- benzoic acid
- methylindolizin
- Prior art date
Links
- 125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 17
- 229910052731 fluorine Inorganic materials 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 239000000651 prodrug Substances 0.000 claims 16
- 229940002612 prodrug Drugs 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 150000002478 indolizines Chemical class 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- -1 nitro, amino Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 201000001431 Hyperuricemia Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229940116269 uric acid Drugs 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 1
- RPNDMLHKAXNOSS-UHFFFAOYSA-N 4-(1-cyano-6,8-difluoroindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=C(F)C=C2F RPNDMLHKAXNOSS-UHFFFAOYSA-N 0.000 claims 1
- JIKFHHSENODMRU-UHFFFAOYSA-N 4-(1-cyano-6,8-difluoroindolizin-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=C(F)C=C2F JIKFHHSENODMRU-UHFFFAOYSA-N 0.000 claims 1
- DXJHZBKZWIVKEG-UHFFFAOYSA-N 4-(1-cyano-6,8-dimethylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound N12C=C(C)C=C(C)C2=C(C#N)C=C1C1=CC=C(C(O)=O)C(O)=C1 DXJHZBKZWIVKEG-UHFFFAOYSA-N 0.000 claims 1
- PTBJLBPJWHGSBX-UHFFFAOYSA-N 4-(1-cyano-6,8-dimethylindolizin-3-yl)benzoic acid Chemical compound N12C=C(C)C=C(C)C2=C(C#N)C=C1C1=CC=C(C(O)=O)C=C1 PTBJLBPJWHGSBX-UHFFFAOYSA-N 0.000 claims 1
- GQVQIJGQJJZAAJ-UHFFFAOYSA-N 4-(1-cyano-6-fluoro-7-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound N12C=C(F)C(C)=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C(O)=C1 GQVQIJGQJJZAAJ-UHFFFAOYSA-N 0.000 claims 1
- MBNUBXUVELIFSZ-UHFFFAOYSA-N 4-(1-cyano-6-fluoro-7-methylindolizin-3-yl)benzoic acid Chemical compound N12C=C(F)C(C)=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C=C1 MBNUBXUVELIFSZ-UHFFFAOYSA-N 0.000 claims 1
- WORSVZBMMQSSOA-UHFFFAOYSA-N 4-(1-cyano-6-fluoroindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=C(F)C=C2 WORSVZBMMQSSOA-UHFFFAOYSA-N 0.000 claims 1
- YFKGUOVCXRTVSF-UHFFFAOYSA-N 4-(1-cyano-6-fluoroindolizin-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=C(F)C=C2 YFKGUOVCXRTVSF-UHFFFAOYSA-N 0.000 claims 1
- JZIIXPCZXXJWBP-UHFFFAOYSA-N 4-(1-cyano-6-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound N12C=C(C)C=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C(O)=C1 JZIIXPCZXXJWBP-UHFFFAOYSA-N 0.000 claims 1
- LDFMFPDEYWJFFK-UHFFFAOYSA-N 4-(1-cyano-6-methylindolizin-3-yl)benzoic acid Chemical compound N12C=C(C)C=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C=C1 LDFMFPDEYWJFFK-UHFFFAOYSA-N 0.000 claims 1
- DZVKKIMBOKQPMK-UHFFFAOYSA-N 4-(1-cyano-7,8-dimethylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C(C)=C(C)C=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 DZVKKIMBOKQPMK-UHFFFAOYSA-N 0.000 claims 1
- DADKEEBULXLDGY-UHFFFAOYSA-N 4-(1-cyano-7,8-dimethylindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C(C)=C(C)C=CN2C=1C1=CC=C(C(O)=O)C=C1 DADKEEBULXLDGY-UHFFFAOYSA-N 0.000 claims 1
- HSCXYVLKMBJEJP-UHFFFAOYSA-N 4-(1-cyano-7-methoxy-6-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound N12C=C(C)C(OC)=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C(O)=C1 HSCXYVLKMBJEJP-UHFFFAOYSA-N 0.000 claims 1
- DVCFGFJVZYHLAA-UHFFFAOYSA-N 4-(1-cyano-7-methoxy-6-methylindolizin-3-yl)benzoic acid Chemical compound N12C=C(C)C(OC)=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C=C1 DVCFGFJVZYHLAA-UHFFFAOYSA-N 0.000 claims 1
- ZETVTZXPMXQUPU-UHFFFAOYSA-N 4-(1-cyano-7-methoxyindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C=C(OC)C=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 ZETVTZXPMXQUPU-UHFFFAOYSA-N 0.000 claims 1
- NGQUJTYWODFAFU-UHFFFAOYSA-N 4-(1-cyano-7-methoxyindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C=C(OC)C=CN2C=1C1=CC=C(C(O)=O)C=C1 NGQUJTYWODFAFU-UHFFFAOYSA-N 0.000 claims 1
- MLNIKOXPLLZXIU-UHFFFAOYSA-N 4-(1-cyano-7-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C=C(C)C=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 MLNIKOXPLLZXIU-UHFFFAOYSA-N 0.000 claims 1
- JXKZPDVSCHTADK-UHFFFAOYSA-N 4-(1-cyano-7-methylindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C=C(C)C=CN2C=1C1=CC=C(C(O)=O)C=C1 JXKZPDVSCHTADK-UHFFFAOYSA-N 0.000 claims 1
- HLGXAFBMGWYEQO-UHFFFAOYSA-N 4-(1-cyano-8-ethylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C(CC)=CC=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 HLGXAFBMGWYEQO-UHFFFAOYSA-N 0.000 claims 1
- XEVFWMQWWLQYGT-UHFFFAOYSA-N 4-(1-cyano-8-fluoro-7-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C(F)=C(C)C=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 XEVFWMQWWLQYGT-UHFFFAOYSA-N 0.000 claims 1
- UQVYQCKTGOHPGW-UHFFFAOYSA-N 4-(1-cyano-8-fluoro-7-methylindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C(F)=C(C)C=CN2C=1C1=CC=C(C(O)=O)C=C1 UQVYQCKTGOHPGW-UHFFFAOYSA-N 0.000 claims 1
- FJQSUIGCWCDAIA-UHFFFAOYSA-N 4-(1-cyano-8-fluoroindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC=C2F FJQSUIGCWCDAIA-UHFFFAOYSA-N 0.000 claims 1
- SRYRXDKEDFQMJB-UHFFFAOYSA-N 4-(1-cyano-8-fluoroindolizin-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC=C2F SRYRXDKEDFQMJB-UHFFFAOYSA-N 0.000 claims 1
- CAGULLPWCBZJRU-UHFFFAOYSA-N 4-(1-cyano-8-methoxyindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C(OC)=CC=CN2C=1C1=CC=C(C(O)=O)C=C1 CAGULLPWCBZJRU-UHFFFAOYSA-N 0.000 claims 1
- CTARCKCAFJKXEB-UHFFFAOYSA-N 4-(1-cyano-8-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C(C)=CC=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 CTARCKCAFJKXEB-UHFFFAOYSA-N 0.000 claims 1
- NWYSAWMPGGRIGN-UHFFFAOYSA-N 4-(1-cyano-8-methylindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C(C)=CC=CN2C=1C1=CC=C(C(O)=O)C=C1 NWYSAWMPGGRIGN-UHFFFAOYSA-N 0.000 claims 1
- FJAVJMJZPIABLH-UHFFFAOYSA-N 4-(1-cyanoindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC=C2 FJAVJMJZPIABLH-UHFFFAOYSA-N 0.000 claims 1
- UIZIKSNONDIBST-UHFFFAOYSA-N 4-(1-cyanoindolizin-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC=C2 UIZIKSNONDIBST-UHFFFAOYSA-N 0.000 claims 1
- JYONSNBKRWZLJK-UHFFFAOYSA-N 4-(6-chloro-1-cyano-7-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound N12C=C(Cl)C(C)=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C(O)=C1 JYONSNBKRWZLJK-UHFFFAOYSA-N 0.000 claims 1
- LUIPDGZMPLXVHP-UHFFFAOYSA-N 4-(6-chloro-1-cyano-7-methylindolizin-3-yl)benzoic acid Chemical compound N12C=C(Cl)C(C)=CC2=C(C#N)C=C1C1=CC=C(C(O)=O)C=C1 LUIPDGZMPLXVHP-UHFFFAOYSA-N 0.000 claims 1
- PPWCOKAYUQACSW-UHFFFAOYSA-N 4-(7-chloro-1-cyano-8-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C(C)=C(Cl)C=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 PPWCOKAYUQACSW-UHFFFAOYSA-N 0.000 claims 1
- NWWFRFPAPJGBET-UHFFFAOYSA-N 4-(7-chloro-1-cyano-8-methylindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C(C)=C(Cl)C=CN2C=1C1=CC=C(C(O)=O)C=C1 NWWFRFPAPJGBET-UHFFFAOYSA-N 0.000 claims 1
- SUJFUNSZQMTIQE-UHFFFAOYSA-N 4-(8-chloro-1-cyano-7-methylindolizin-3-yl)-2-hydroxybenzoic acid Chemical compound C=1C(C#N)=C2C(Cl)=C(C)C=CN2C=1C1=CC=C(C(O)=O)C(O)=C1 SUJFUNSZQMTIQE-UHFFFAOYSA-N 0.000 claims 1
- PEMKPLAPBYFDRY-UHFFFAOYSA-N 4-(8-chloro-1-cyano-7-methylindolizin-3-yl)benzoic acid Chemical compound C=1C(C#N)=C2C(Cl)=C(C)C=CN2C=1C1=CC=C(C(O)=O)C=C1 PEMKPLAPBYFDRY-UHFFFAOYSA-N 0.000 claims 1
- SAUJIWXQRNTXMZ-UHFFFAOYSA-N 4-[1-cyano-6-fluoro-7-(trifluoromethyl)indolizin-3-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=C(F)C(C(F)(F)F)=C2 SAUJIWXQRNTXMZ-UHFFFAOYSA-N 0.000 claims 1
- OAAZYTVHXIUUAQ-UHFFFAOYSA-N 4-[1-cyano-7-(fluoromethyl)indolizin-3-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC(CF)=C2 OAAZYTVHXIUUAQ-UHFFFAOYSA-N 0.000 claims 1
- SOVHCKXXVLTTBN-UHFFFAOYSA-N 4-[1-cyano-7-(fluoromethyl)indolizin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC(CF)=C2 SOVHCKXXVLTTBN-UHFFFAOYSA-N 0.000 claims 1
- BXNZMWOEIYTRTI-UHFFFAOYSA-N 4-[1-cyano-7-(trifluoromethyl)indolizin-3-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC(C(F)(F)F)=C2 BXNZMWOEIYTRTI-UHFFFAOYSA-N 0.000 claims 1
- MXTGHMBZETXYPR-UHFFFAOYSA-N 4-[1-cyano-7-(trifluoromethyl)indolizin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C#N)=C2N1C=CC(C(F)(F)F)=C2 MXTGHMBZETXYPR-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 208000009911 Urinary Calculi Diseases 0.000 claims 1
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000002917 arthritic effect Effects 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 208000008281 urolithiasis Diseases 0.000 claims 1
- 239000003064 xanthine oxidase inhibitor Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/4353—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (15)
1. Derivat indolizina predstavljen formulom (I):
[Kem. 1]
[image]
gdje
prsten U predstavlja aril ili heteroaril;
R1 predstavlja atom halogena, hidroksi skupinu, nitro, amino ili C1-6 alkil koji može biti supstituiran atomom fluora;
R2 predstavlja bilo što od sljedećeg (1) do (7):
(1) atom halogena;
(2) hidroksi skupinu;
(3) amino;
(4) karbamoil;
(5) cijano;
(6) karboksi;
(7) C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C1-6 alkoksi, mono(di) C1-6 alkilamin, C2-7 acil, C2-7 acilamin, mono(di)C1-6 alkilkarbamoil, C1-6 alkilsulfonil, C1-6 alkilsulfonilamin, mono(di)C1-6 alkilsulfamoil, C1-6 alkiltio, C2-6 alkenil C1-6 alkoksi, C3-8 cikloalkil, 3 do 8-eročlani heterocikloalkil, C5-8 cikloalkenil, 5 do 8-eročlani heterocikloalkenil, C3-8 cikloalkiloksi, C3-8 cikloalkilamin, C3-8 cikloalkil C1-6 alkil, C3-8 cikloalkil C1-6 alkoksi, C3-8 cikloalkil C1-6 alkilamino aril, heteroaril, ariloksi, arilamino, arilkarbonil, arilkarbonilamin, arilC1-6 alkoksi, heteroariloksi, heteroarilamin, heteroarilkarbonil ili heteroarilkarbonilamin od kojih svaki može imati bilo koju skupinu izabranu iz grupe supstituenata α;
m predstavlja cijeli broj od 0 do 2, i kada m je 2, ti R1 su po izboru različiti jedan od drugoga;
n predstavlja cijeli broj od 0 do 3, i kada n je 2 ili 3, ti R2 su po izboru različiti jedan od drugoga; i kada u indolizinskom prstenu postoji veza dva R2 sa susjednim atomima i nezavisno predstavljaju skupinu izabranu iz grupe koja obuhvaća C1-6 alkil koji može biti supstituiran atomom fluora i C1-6 alkoksi koji može biti supstituiran atomom fluora, ta dva R2 po izboru formiraju 5 do 8-eročlani prsten zajedno s veznim atomima u indolizinskom prstenu;
R3 predstavlja atom vodika, atom klora ili atom fluora; i
grupa supstituenata α obuhvaća atom fluora, atom klora, hidroksi skupinu, amino, karboksi, karbamoil, cijano, C1-6 alkil, C1-6 alkoksi i mono (di)C1-6 alkilamino, ili njihov prolijek, ili njihovu farmaceutski prihvatljivu sol, pri čemu "prolijek" označava spoj u kojem je jedna ili više karboksi skupina spoja predstavljenog gore općom formulom (I) supstituirana skupinom koja daje prolijek, gdje se skupina koja daje prolijek izabire iz grupe koja obuhvaća C1-6 alkil, C1-6 alkil-COO-C1-6 alkilen, C1-6 alkil-OCOO-C1-6 alkilen, C3-8 cikloalkil-OCOO-C1-6 alkilen, mono(di)hidroksi C1-6 alkil, mono(di)hidroksi C1-6 alkil-OCOO-C1-6 alkilen, C1-6 alkoksi C1-6 alkoksi C1-6 alkil, mono(di)C1-6 alkilamino C1-6 alkil, 3 do 8-eročlani heterocikloalkil C1-6 alkil, i C1-6 alkil-OCO-amino C1-6 alkilen.
2. Derivat indolizina prema zahtjevu 1, predstavljen formulom (Ia):
[Kem. 2]
[image]
gdje
prsten U predstavlja aril ili heteroaril;
R1a predstavlja atom vodika, atom fluora, hidroksi skupinu, amino, metil ili trifluorometil;
R2a i R2b nezavisno predstavljaju bilo što od sljedećeg (a1) do (a4):
(a1) atom vodika;
(a2) atom halogena;
(a3) hidroksi skupinu;
(a4) C1-6 alkil, C1-6 alkoksi, mono(di)C1-6 alkilamin, C2-7 acil, C1-6 alkiltio, C3-8 cikloalkil, 3 do 8-eročlani heterocikloalkil, aril ili heteroaril od kojih svaki može imati bilo koju skupinu izabranu iz grupe supstituenata α;
R2c predstavlja atom vodika, atom halogena, hidroksi skupinu, C1-6 alkil koji može imati bilo koju skupinu izabranu iz grupe supstituenata α ili C1-6 alkoksi koji može imati bilo koju skupinu izabranu iz grupe supstituenata α, ili
kada R2a i R2b, ili R2b i R2c nezavisno predstavljaju skupinu izabranu iz grupe koja obuhvaća C1-6alkil koji može biti supstituiran atomom fluora i C1-6 alkoksi koji može biti supstituiran atomom fluora, oni po izboru formiraju 5 do 8-eročlani prsten zajedno s veznim atomima u indolizinskom prstenu;
R2d predstavlja atom vodika ili atom fluora;
R3a predstavlja atom vodika ili atom fluora; i grupa supstituenata α ima isto značenje kako je opisano u zahtjevu 1, ili njihov prolijek, ili njihovu farmaceutski prihvatljivu sol, pri čemu "prolijek" označava spoj u kojem je jedna ili više karboksi skupina spoja predstavljenog gore općom formulom (Ia) supstituirana skupinom koja daje prolijek, gdje se skupina koja daje prolijek izabire iz grupe koja obuhvaća C1-6 alkil, C1-6 alkil-COO-C1-6 alkilen, C1-6 alkil-OCOO-C1-6 alkilen, C3-8 cikloalkil-OCOO-C1-6 alkilen, mono(di)hidroksi C1-6 alkil, mono(di)hidroksi C1-6 alkil-OCOO-C1-6alkilen, C1-6 alkoksi C1-6 alkoksi C1-6 alkil, mono(di)C1-6 alkilamino C1-6 alkil, 3 do 8-eročlani heterocikloalkil C1-6 alkil, i C1-6 alkil-OCO-amino C1-6 alkilen.
3. Derivat indolizina prema zahtjevu 2, gdje prsten U predstavlja prsten benzena, prsten piridina, prsten tiofena ili tiazola, ili njihov prolijek, ili farmaceutski prihvatljivu sol.
4. Derivat indolizina prema zahtjevu 2, gdje skupina predstavljena formulom:
[Kem. 3]
[image]
je skupina predstavljena formulom:
[Kem. 4]
[image]
i R1a predstavlja atom vodika ili hidroksi skupinu, ili prolijek, ili farmaceutski prihvatljivu sol.
5. Derivat indolizina prema zahtjevu 3 ili 4, gdje R2a i R2b nezavisno predstavljaju bilo što od sljedećeg (b1) do (b4):
(b1) atom vodika;
(b2) atom halogena;
(b3) hidroksi skupinu;
(b4) C1-6 alkil, C1-6 alkoksi, mono(di)C1-6 alkilamino ili hidroksi C1-6 alkil od kojih svaki može biti supstituiran atomom fluora; i
R2c predstavlja atom vodika, atom halogena, hidroksi skupinu, C1-6 alkil koji može biti supstituiran atomom fluora ili C1-6 alkoksi koji može biti supstituiran atomom fluora, ili prolijek, ili farmaceutski prihvatljiva sol.
6. Derivat indolizina prema bilo kojem od zahtjeva 2 do 5, gdje R2d predstavlja atom vodika, ili njegov prolijek, ili farmaceutski prihvatljiva sol.
7. Derivat indolizina prema bilo kojem od zahtjeva 1 do 6, gdje R3 ili R3a predstavlja atom vodika, ili njegov prolijek, ili farmaceutski prihvatljiva sol.
8. Derivat indolizina prema zahtjevu 6 ili 7, gdje R1a predstavlja atom vodika ili hidroksi skupinu;
R2a predstavlja atom vodika, atom fluora, atom klora, metil, etil, metoksi, monofluorometil, difluorometil, trifluorometil, difluorometoksi ili trifluorometoksi;
R2b predstavlja atom vodika, atom fluora, atom klora, metil, etil, metoksi, monofluorometil, difluorometil, trifluorometil, difluorometoksi ili trifluorometoksi; po izboru
gdje R2b predstavlja atom vodika, metil, etil, metoksi, monofluorometil, difluorometil, trifluorometil, difluorometoksi ili trifluorometoksi; i
R2c predstavlja atom vodika, atom fluora, atom klora, metil, monofluorometil, difluorometil ili trifluorometil, ili prolijek, ili farmaceutski prihvatljiva sol.
9. Derivat indolizina prema zahtjevu 8, gdje R1a predstavlja atom vodika, ili prolijek, ili farmaceutski prihvatljiva sol.
10. Derivat indolizina prema zahtjevu 8, gdje R1a predstavlja hidroksi skupinu, ili prolijek, ili farmaceutski prihvatljiva sol.
11. Derivat indolizina prema zahtjevu 8, koji je izabran iz grupe koja obuhvaća:
4-(1-cijanoindolizin-3-il) benzojeva kiselina,
4-(1-cijano-7-metilindolizin-3-il) benzojeva kiselina,
4-(8-klor-1-cijanoindoizine-3-il) benzojeva kiselina,
4-(1-cijano-8-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-6-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-6, 8-dimetilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-8-fluoro-7-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-6-fluoro-7-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-7-etilindoizine-3-il) benzojeva kiselina,
4-(1-cijano-8-etilindoizine-3-il) benzojeva kiselina,
4-(1-cijano-8-fluoroindolizin-3-il) benzojeva kiselina,
4-(1-cijano-6-fluoroindolizin-3-il) benzojeva kiselina,
4-(1-cijano-7-trifluorometilindolizin-3-il) benzojeva kiselina,
4-(1-cijanoindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-7-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(l-cijano-8-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-6-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-6, 8-dimetilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-6-fluoro-7-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-8-fluoro-7-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-8-etilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-8-fluoroindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-6-fluoroindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-7-trifluorometilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-7-fluorometilindolizin-3-il) benzojeva kiselina,
4-(6-klor-1-cijano-7-metilindolizin-3-il) benzojeva kiselina,
4-(8-klor-1-cijano-7-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-7, 8-dimetilindolizin-3-il) benzojeva kiselina,
4-(7-klor-1-cijano-8-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-6, 8-difluoroindolizin-3-il) benzojeva kiselina,
4-(1-cijano-8-metoksiindolizin-3-il) benzojeva kiselina,
4-(1-cijano-7-metoksiindolizin-3-il) benzojeva kiselina,
4-(1-cijano-7-metoksi-6-metilindolizin-3-il) benzojeva kiselina,
4-(1-cijano-6-fluoro-7-trifluorometilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(6-klor-1-cijano-7-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(8-klor-1-cijano-7-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-7, 8-dimetilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(7-klor-1-cijano-8-metilindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-6, 8-difluoroindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-7-metoksiindolizin-3-il)-2-hidroksibenzojeva kiselina,
4-(1-cijano-7-metoksi-6-metilindolizin-3-il)-2-hidroksibenzojeva kiselina, i
4-(1-cijano-7-fluorometilindolizin-3-il)-2-hidroksibenzojeva kiselina, ili farmaceutski prihvatljiva sol.
12. Derivat indolizina ili njegov prolijek ili farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 11, koji je inhibitor oksidaze ksantina.
13. Farmaceutska smjesa koja sadrži kao djelatnu tvar derivat indolizina ili njegov prolijek ili farmaceutski prihvatljivu sol prema bilo kojem od zahtjeva 1 do 11.
14. Farmaceutska smjesa prema zahtjevu 13, za uporabu u prevenciji ili liječenju bolesti izabrane iz grupe koja obuhvaća hiperurikemiju, giht s kamencima, artritični giht, poremećaj bubrega povezan s hiperurikemijom i urinarni kamenci po izboru
za uporabu u prevenciji ili liječenju hiperurikemije, po izboru
za uporabu za snižavanje razine urične kiseline u serumu.
15. Farmaceutska smjesa prema zahtjevu 13, koja je inhibitor proizvodnje urične kiseline.
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WO2012043638A1 (ja) * | 2010-09-29 | 2012-04-05 | キッセイ薬品工業株式会社 | (アザ)インドリジン誘導体及びその医薬用途 |
NO2686520T3 (hr) * | 2011-06-06 | 2018-03-17 | ||
CN103889989B (zh) * | 2011-08-24 | 2016-01-20 | 橘生药品工业株式会社 | 稠合杂环衍生物及其制药用途 |
WO2014065275A1 (ja) | 2012-10-23 | 2014-05-01 | 国立大学法人福井大学 | 腫瘍融解症候群の治療薬及び予防薬 |
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CN114404414A (zh) | 2013-06-13 | 2022-04-29 | 阿克比治疗有限公司 | 用于治疗贫血症的组合物和方法 |
WO2015123437A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
PL3105218T3 (pl) | 2014-02-13 | 2020-03-31 | Incyte Corporation | Cyklopropyloaminy jako inhibitory lsd1 |
US9493442B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
LT3105226T (lt) | 2014-02-13 | 2019-11-11 | Incyte Corp | Ciklopropilaminai, kaip lsd1 inhibitoriai |
WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
WO2016118858A1 (en) | 2015-01-23 | 2016-07-28 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
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TWI822776B (zh) | 2018-05-09 | 2023-11-21 | 美商阿克比治療有限公司 | 用於製備2-[[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基]乙酸之方法 |
WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
CN111943957B (zh) * | 2019-05-17 | 2023-01-06 | 中国医学科学院药物研究所 | 喹啉甲酰胺类化合物及其制备方法和用途 |
JP2023052711A (ja) * | 2020-03-04 | 2023-04-12 | 国立研究開発法人理化学研究所 | 化合物を放出する方法 |
AR126164A1 (es) * | 2021-06-17 | 2023-09-27 | Lg Chemical Ltd | Formulación compuesta para dosificación oral que comprende ácido 1-(3-ciano-1-isopropil-indol-5-il)pirazol-4-carboxílico |
CN115785018A (zh) * | 2022-12-26 | 2023-03-14 | 湖北广济药业股份有限公司 | 一种非布司他脱羧杂质的制备方法 |
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FR2779724B1 (fr) * | 1998-06-10 | 2001-04-20 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
CN101282934A (zh) * | 2005-10-07 | 2008-10-08 | 安斯泰来制药株式会社 | 三芳基羧酸衍生物 |
US7947707B2 (en) | 2005-10-07 | 2011-05-24 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
BRPI0810524B8 (pt) | 2007-04-11 | 2021-05-25 | Kissei Pharmaceutical | derivado de (aza)indol, inibidor de xantina oxidase e composição farmacêutica compreendendo o dito derivado |
MX2009010491A (es) | 2007-04-11 | 2009-11-09 | Kissei Pharmaceutical | Derivado heterociclico de 5 miembros y su uso para propositos medicos. |
WO2008126901A1 (ja) * | 2007-04-11 | 2008-10-23 | Kissei Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびそれを含有する医薬組成物 |
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- 2013-10-17 CY CY20131100921T patent/CY1114520T1/el unknown
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ZA201107085B (en) | 2012-12-27 |
CA2755132C (en) | 2018-02-13 |
TW201040178A (en) | 2010-11-16 |
HK1165793A1 (en) | 2012-10-12 |
US8748452B2 (en) | 2014-06-10 |
JP5638513B2 (ja) | 2014-12-10 |
BRPI1013432B1 (pt) | 2019-12-17 |
SI2415771T1 (sl) | 2013-12-31 |
CN102365281A (zh) | 2012-02-29 |
EP2415771B1 (en) | 2013-07-31 |
WO2010113942A1 (ja) | 2010-10-07 |
AU2010231615B2 (en) | 2014-05-15 |
MX2011010395A (es) | 2011-10-24 |
AU2010231615A1 (en) | 2011-11-03 |
DK2415771T3 (da) | 2013-10-14 |
BRPI1013432A2 (pt) | 2016-04-05 |
CY1114520T1 (el) | 2016-10-05 |
PT2415771E (pt) | 2013-10-03 |
JPWO2010113942A1 (ja) | 2012-10-11 |
RU2529868C2 (ru) | 2014-10-10 |
KR20110132599A (ko) | 2011-12-08 |
TWI471325B (zh) | 2015-02-01 |
EP2415771A4 (en) | 2012-08-29 |
US20120015972A1 (en) | 2012-01-19 |
EP2415771A1 (en) | 2012-02-08 |
CN102365281B (zh) | 2014-11-12 |
CA2755132A1 (en) | 2010-10-07 |
PL2415771T3 (pl) | 2014-01-31 |
RU2011143741A (ru) | 2013-05-10 |
ES2429148T3 (es) | 2013-11-13 |
KR101772963B1 (ko) | 2017-08-31 |
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