CN103848798A - 2-芳基硒唑化合物及其药物组合物 - Google Patents
2-芳基硒唑化合物及其药物组合物 Download PDFInfo
- Publication number
- CN103848798A CN103848798A CN201210504310.8A CN201210504310A CN103848798A CN 103848798 A CN103848798 A CN 103848798A CN 201210504310 A CN201210504310 A CN 201210504310A CN 103848798 A CN103848798 A CN 103848798A
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- Prior art keywords
- selenazole
- methyl
- substituted
- carboxylic acid
- cyano
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 239000000203 mixture Substances 0.000 title abstract description 38
- 201000005569 Gout Diseases 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 201000001431 Hyperuricemia Diseases 0.000 claims abstract description 19
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
- -1 heterocyclic radical Chemical class 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000003254 radicals Chemical class 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- JXWZPOXVTBYQLO-UHFFFAOYSA-N 2-(3-cyano-4-propan-2-ylsulfanylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(SC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 JXWZPOXVTBYQLO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
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- OZQRSDCVZYGMMZ-UHFFFAOYSA-N 2-[3-cyano-4-(cyclopropylmethoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1OCC1CC1 OZQRSDCVZYGMMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000005493 quinolyl group Chemical group 0.000 claims description 8
- AIVRMJQFXVTQFW-UHFFFAOYSA-N 2-(3-cyano-4-ethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OCC)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 AIVRMJQFXVTQFW-UHFFFAOYSA-N 0.000 claims description 7
- ZEOSJTLLZKNHCC-UHFFFAOYSA-N 2-(3-cyano-4-propan-2-yloxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 ZEOSJTLLZKNHCC-UHFFFAOYSA-N 0.000 claims description 7
- VGMHPKSVFAHOHY-UHFFFAOYSA-N 2-[3-cyano-4-(3-methylbutoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OCCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 VGMHPKSVFAHOHY-UHFFFAOYSA-N 0.000 claims description 7
- UGFYBXZHOBOTIB-UHFFFAOYSA-N 2-[3-cyano-4-(cyclohexylmethoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1OCC1CCCCC1 UGFYBXZHOBOTIB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- DJWSKQZSUPNTPC-UHFFFAOYSA-N 2-(3-cyano-4-phenylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1C1=CC=CC=C1 DJWSKQZSUPNTPC-UHFFFAOYSA-N 0.000 claims description 6
- GDGJMHSGANQKMG-UHFFFAOYSA-N 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 GDGJMHSGANQKMG-UHFFFAOYSA-N 0.000 claims description 6
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- VWRYHVIUYDSFOD-UHFFFAOYSA-N 2-(3-cyano-4-naphthalen-1-ylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C(C#N)=C1 VWRYHVIUYDSFOD-UHFFFAOYSA-N 0.000 claims description 5
- VWPQHAKPTFXZFI-UHFFFAOYSA-N 2-(3-cyano-4-phenylmethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1OCC1=CC=CC=C1 VWPQHAKPTFXZFI-UHFFFAOYSA-N 0.000 claims description 5
- LFAFXFBGJIKZDF-UHFFFAOYSA-N 2-(3-cyano-4-pyridin-2-ylsulfanylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1SC1=CC=CC=N1 LFAFXFBGJIKZDF-UHFFFAOYSA-N 0.000 claims description 5
- DMXWCSUBOUNUTQ-UHFFFAOYSA-N 2-[3-chloro-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(Cl)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 DMXWCSUBOUNUTQ-UHFFFAOYSA-N 0.000 claims description 5
- KHIAPBGXFGLAFR-UHFFFAOYSA-N 2-[3-cyano-4-(2,4-dimethoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C1=CC=C(C=2[se]C(=C(C)N=2)C(O)=O)C=C1C#N KHIAPBGXFGLAFR-UHFFFAOYSA-N 0.000 claims description 5
- QFIRBTHRBCNMLO-UHFFFAOYSA-N 2-[3-cyano-4-(2-methoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C=2[se]C(=C(C)N=2)C(O)=O)C=C1C#N QFIRBTHRBCNMLO-UHFFFAOYSA-N 0.000 claims description 5
- WJFJPFIOFQKRCF-UHFFFAOYSA-N 2-[3-cyano-4-(2-methylpropylsulfanyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(SCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 WJFJPFIOFQKRCF-UHFFFAOYSA-N 0.000 claims description 5
- IKUQIZJDOLOTMP-UHFFFAOYSA-N 2-[3-cyano-4-(3,4,5-trimethoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C(#N)C1=C(C=CC(=C1)C=1[Se]C(=C(N1)C)C(=O)O)C1=CC(=C(C(=C1)OC)OC)OC IKUQIZJDOLOTMP-UHFFFAOYSA-N 0.000 claims description 5
- AAUGNNZVJNZLJZ-UHFFFAOYSA-N 2-[3-cyano-4-(3,4-difluorophenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1C1=CC=C(F)C(F)=C1 AAUGNNZVJNZLJZ-UHFFFAOYSA-N 0.000 claims description 5
- ANPIKECPJBIJSM-UHFFFAOYSA-N 2-[3-cyano-4-(3,4-dimethoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=2[se]C(=C(C)N=2)C(O)=O)C=C1C#N ANPIKECPJBIJSM-UHFFFAOYSA-N 0.000 claims description 5
- CNZVTBICZKIRLX-UHFFFAOYSA-N 2-[3-cyano-4-(3-fluoro-4-methoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C(#N)C1=C(C=CC(=C1)C=1[Se]C(=C(N1)C)C(=O)O)C1=CC(=C(C=C1)OC)F CNZVTBICZKIRLX-UHFFFAOYSA-N 0.000 claims description 5
- AZYCOLAQWQXOJE-UHFFFAOYSA-N 2-[3-cyano-4-(3-methoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C(#N)C1=C(C=CC(=C1)C=1[Se]C(=C(N1)C)C(=O)O)C1=CC(=CC=C1)OC AZYCOLAQWQXOJE-UHFFFAOYSA-N 0.000 claims description 5
- RNRUTSFPBWFBJU-UHFFFAOYSA-N 2-[3-cyano-4-(4-methoxyphenyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2[se]C(=C(C)N=2)C(O)=O)C=C1C#N RNRUTSFPBWFBJU-UHFFFAOYSA-N 0.000 claims description 5
- HLFHKDUVCDXMNB-UHFFFAOYSA-N 2-[3-cyano-4-(4-methylpiperazin-1-yl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC=C(C=2[se]C(=C(C)N=2)C(O)=O)C=C1C#N HLFHKDUVCDXMNB-UHFFFAOYSA-N 0.000 claims description 5
- GYLQJSKRAQHYCO-UHFFFAOYSA-N 2-[3-cyano-4-(dimethylamino)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(N(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 GYLQJSKRAQHYCO-UHFFFAOYSA-N 0.000 claims description 5
- BJFWQEZJZRRELZ-UHFFFAOYSA-N 2-[3-cyano-4-[3-(trifluoromethoxy)phenyl]phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C(#N)C1=C(C=CC(=C1)C=1[Se]C(=C(N1)C)C(=O)O)C1=CC(=CC=C1)OC(F)(F)F BJFWQEZJZRRELZ-UHFFFAOYSA-N 0.000 claims description 5
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- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
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- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 108010078530 urate transporter Proteins 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- 150000007968 uric acids Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
- C07D293/02—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms not condensed with other rings
- C07D293/04—Five-membered rings
- C07D293/06—Selenazoles; Hydrogenated selenazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- 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
- A61K31/4365—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 having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/495—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
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Health & Medical 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)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
化合物编号 | IC50(nM) | 化合物编号 | IC50(nM) | 化合物编号 | IC50(nM) |
化合物6 | 2.29 | 化合物22 | 3.24 | 化合物43 | 13.89 |
化合物7 | 2.05 | 化合物23 | 2.37 | 化合物44 | 2.30 |
化合物8 | 2.40 | 化合物24 | 1.67 | 化合物45 | 9.13 |
化合物9 | 3.28 | 化合物25 | 3.47 | 化合物46 | 4.11 |
化合物10 | 12.43 | 化合物26 | 2.78 | 化合物47 | 2.52 |
化合物11 | 2.85 | 化合物27 | 2.53 | 化合物51 | 10.25 |
化合物12 | 2.97 | 化合物28 | 2.67 | 化合物55 | 3.06 |
化合物14 | 1.70 | 化合物30 | 4.84 | 化合物62 | 8.56 |
化合物15 | 3.25 | 化合物35 | 2.63 | 化合物67 | >100 |
化合物16 | 2.99 | 化合物37 | 1.32 | 化合物68 | 2.84 |
化合物17 | 3.79 | 化合物38 | 2.56 | 化合物69 | 6.01 |
化合物18 | 2.70 | 化合物39 | 3.58 | 化合物70 | 31.07 |
化合物19 | 4.61 | 化合物40 | 12.06 | 化合物74 | 10.08 |
化合物20 | 3.92 | 化合物41 | 5.19 | ||
化合物21 | 2.61 | 化合物42 | 3.07 | Febuxostat | 2.78 |
Claims (13)
Priority Applications (5)
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CN201210504310.8A CN103848798B (zh) | 2012-11-30 | 2012-11-30 | 2-芳基硒唑化合物及其药物组合物 |
PCT/CN2013/087736 WO2014082548A1 (zh) | 2012-11-30 | 2013-11-24 | 2-芳基硒唑化合物及其药物组合物 |
EP13858539.3A EP2927219B1 (en) | 2012-11-30 | 2013-11-24 | 2-aryl selenazole compound and pharmaceutical composition thereof |
JP2015544335A JP6143877B2 (ja) | 2012-11-30 | 2013-11-24 | 2−アリールセレナゾール化合物及びその薬剤組成物 |
US14/648,664 US9802907B2 (en) | 2012-11-30 | 2013-11-24 | 2-aryl selenazole compound and pharmaceutical composition thereof |
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CN201210504310.8A CN103848798B (zh) | 2012-11-30 | 2012-11-30 | 2-芳基硒唑化合物及其药物组合物 |
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CN103848798B CN103848798B (zh) | 2016-01-06 |
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US (1) | US9802907B2 (zh) |
EP (1) | EP2927219B1 (zh) |
JP (1) | JP6143877B2 (zh) |
CN (1) | CN103848798B (zh) |
WO (1) | WO2014082548A1 (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103936693A (zh) * | 2013-01-22 | 2014-07-23 | 沈阳药科大学 | 2-(3-氰基-4-取代苯基)-4-甲基-1,3-硒唑-5-甲酸及其酯类化合物和制备方法 |
CN108358866A (zh) * | 2017-01-12 | 2018-08-03 | 江西同和药业股份有限公司 | 一种非布司他中间体的制备方法及其在制备非布司他中的应用 |
CN111662239A (zh) * | 2019-03-06 | 2020-09-15 | 中国医学科学院药物研究所 | 1,2,4-三唑类化合物及其制法和药物用途 |
CN113354616A (zh) * | 2020-03-05 | 2021-09-07 | 中国医学科学院药物研究所 | 二芳基-1,2,4-三唑类化合物及其制法和药物用途 |
WO2022083687A1 (zh) * | 2020-10-21 | 2022-04-28 | 南京明德新药研发有限公司 | 硒杂环类化合物及其应用 |
WO2023202706A1 (zh) * | 2022-04-21 | 2023-10-26 | 南京明德新药研发有限公司 | 硒杂环类化合物的盐型和晶型及其应用 |
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CN102781924A (zh) * | 2010-02-25 | 2012-11-14 | 首尔大学校产学协力财团 | 用作过氧化物酶体增殖剂激活受体的配体的硒唑衍生物、其制备方法及其化合物的用途 |
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- 2013-11-24 JP JP2015544335A patent/JP6143877B2/ja not_active Expired - Fee Related
- 2013-11-24 WO PCT/CN2013/087736 patent/WO2014082548A1/zh active Application Filing
- 2013-11-24 US US14/648,664 patent/US9802907B2/en active Active
- 2013-11-24 EP EP13858539.3A patent/EP2927219B1/en not_active Not-in-force
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103936693A (zh) * | 2013-01-22 | 2014-07-23 | 沈阳药科大学 | 2-(3-氰基-4-取代苯基)-4-甲基-1,3-硒唑-5-甲酸及其酯类化合物和制备方法 |
CN108358866A (zh) * | 2017-01-12 | 2018-08-03 | 江西同和药业股份有限公司 | 一种非布司他中间体的制备方法及其在制备非布司他中的应用 |
CN108358866B (zh) * | 2017-01-12 | 2021-03-23 | 江西同和药业股份有限公司 | 一种非布司他中间体的制备方法及其在制备非布司他中的应用 |
CN111662239A (zh) * | 2019-03-06 | 2020-09-15 | 中国医学科学院药物研究所 | 1,2,4-三唑类化合物及其制法和药物用途 |
CN111662239B (zh) * | 2019-03-06 | 2023-07-28 | 中国医学科学院药物研究所 | 1,2,4-三唑类化合物及其制法和药物用途 |
CN113354616A (zh) * | 2020-03-05 | 2021-09-07 | 中国医学科学院药物研究所 | 二芳基-1,2,4-三唑类化合物及其制法和药物用途 |
CN113354616B (zh) * | 2020-03-05 | 2024-03-26 | 中国医学科学院药物研究所 | 二芳基-1,2,4-三唑类化合物及其制法和药物用途 |
WO2022083687A1 (zh) * | 2020-10-21 | 2022-04-28 | 南京明德新药研发有限公司 | 硒杂环类化合物及其应用 |
WO2023202706A1 (zh) * | 2022-04-21 | 2023-10-26 | 南京明德新药研发有限公司 | 硒杂环类化合物的盐型和晶型及其应用 |
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WO2014082548A1 (zh) | 2014-06-05 |
EP2927219B1 (en) | 2018-05-30 |
JP2016500115A (ja) | 2016-01-07 |
EP2927219A1 (en) | 2015-10-07 |
US20150291543A1 (en) | 2015-10-15 |
JP6143877B2 (ja) | 2017-06-07 |
CN103848798B (zh) | 2016-01-06 |
EP2927219A4 (en) | 2016-07-06 |
US9802907B2 (en) | 2017-10-31 |
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