CN103864783A - 用于治疗丙型肝炎的化合物 - Google Patents
用于治疗丙型肝炎的化合物 Download PDFInfo
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- CN103864783A CN103864783A CN201410060239.8A CN201410060239A CN103864783A CN 103864783 A CN103864783 A CN 103864783A CN 201410060239 A CN201410060239 A CN 201410060239A CN 103864783 A CN103864783 A CN 103864783A
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- Prior art keywords
- phenyl
- alkyl
- hydrogen
- solvent
- pyridine
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 459
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 208
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 157
- -1 dioxo thiazinyl Chemical group 0.000 claims description 134
- 125000000217 alkyl group Chemical group 0.000 claims description 132
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
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- JVOGPCAZHXALIS-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=CC=CC2=C(C(=O)N)C=NN21 JVOGPCAZHXALIS-UHFFFAOYSA-N 0.000 claims description 32
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 27
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
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- 125000004076 pyridyl group Chemical group 0.000 claims description 17
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- 125000005936 piperidyl group Chemical group 0.000 claims description 10
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- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 7
- WRJDMGHOBCKBJC-UHFFFAOYSA-N furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=COC2=N1 WRJDMGHOBCKBJC-UHFFFAOYSA-N 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
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- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- YMNBJUCMFGAAJQ-UHFFFAOYSA-N methyl furo[2,3-b]pyridine-3-carboxylate Chemical class C1=CC=C2C(C(=O)OC)=COC2=N1 YMNBJUCMFGAAJQ-UHFFFAOYSA-N 0.000 description 1
- VKXLRCACNQKJRQ-UHFFFAOYSA-N methyl furo[3,2-b]pyridine-3-carboxylate Chemical class O1C=C(C2=NC=CC=C21)C(=O)OC VKXLRCACNQKJRQ-UHFFFAOYSA-N 0.000 description 1
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 210000004897 n-terminal region Anatomy 0.000 description 1
- XBLVHTDFJBKJLG-UHFFFAOYSA-N nicotinic acid ethyl ester Natural products CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 1
- 108091027963 non-coding RNA Proteins 0.000 description 1
- 102000042567 non-coding RNA Human genes 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- OHYYCVIHMUHMQF-UHFFFAOYSA-N phenyl but-2-ynoate Chemical compound CC#CC(=O)OC1=CC=CC=C1 OHYYCVIHMUHMQF-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002336 ribonucleotide Substances 0.000 description 1
- 125000002652 ribonucleotide group Chemical group 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- QCIWZIYBBNEPKB-UHFFFAOYSA-N tert-butyl(dimethyl)silane Chemical compound C[SiH](C)C(C)(C)C QCIWZIYBBNEPKB-UHFFFAOYSA-N 0.000 description 1
- XXSLZJZUSYNITM-UHFFFAOYSA-N tetrabutylammonium tribromide Chemical compound Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC XXSLZJZUSYNITM-UHFFFAOYSA-N 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 210000000605 viral structure Anatomy 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000000277 virosome Substances 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (2)
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| US9600408P | 2008-09-11 | 2008-09-11 | |
| US61/096,004 | 2008-09-11 |
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| CN200980144810.1A Division CN102209711B (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
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|---|---|
| CN103864783A true CN103864783A (zh) | 2014-06-18 |
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| CN200980144810.1A Expired - Fee Related CN102209711B (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
| CN201410060239.8A Pending CN103864783A (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN200980144810.1A Expired - Fee Related CN102209711B (zh) | 2008-09-11 | 2009-09-02 | 用于治疗丙型肝炎的化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8198449B2 (2) |
| EP (1) | EP2331502B1 (2) |
| JP (1) | JP2012502099A (2) |
| KR (1) | KR20110056537A (2) |
| CN (2) | CN102209711B (2) |
| AR (1) | AR073586A1 (2) |
| AU (1) | AU2009291993A1 (2) |
| MX (1) | MX2011002471A (2) |
| TW (1) | TW201014855A (2) |
| WO (1) | WO2010030538A2 (2) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101774035B1 (ko) | 2009-10-30 | 2017-09-01 | 얀센 파마슈티카 엔.브이. | 이미다조［１，２―ｂ］피리다진 유도체 및 ＰＤＥ１０ 저해제로서의 그의 용도 |
| EP2496578A4 (en) * | 2009-11-05 | 2013-08-21 | Univ Notre Dame Du Lac | IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF |
| FR2953520B1 (fr) * | 2009-12-04 | 2011-11-25 | Sanofi Aventis | Derives de diphenyl-pyrazolopyridines, leur preparation et leur application en therapeutique |
| US8324212B2 (en) * | 2010-02-25 | 2012-12-04 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| WO2011112186A1 (en) * | 2010-03-10 | 2011-09-15 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis c |
| US8354410B2 (en) | 2010-03-11 | 2013-01-15 | Bristol-Meyers Squibb Company | Compounds for the treatment of hepatitis C |
| AR082453A1 (es) * | 2010-04-21 | 2012-12-12 | Novartis Ag | Compuestos de furopiridina, composiciones farmaceuticas que los contienen y usos de los mismos |
| US8445497B2 (en) | 2010-06-30 | 2013-05-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| SG189882A1 (en) * | 2010-10-20 | 2013-06-28 | Biota Scient Management | Viral polymerase inhibitors |
| SG189985A1 (en) | 2010-10-26 | 2013-06-28 | Presidio Pharmaceuticals Inc | Inhibitors of hepatitis c virus |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AU2013217224B2 (en) | 2012-02-10 | 2017-04-06 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
| WO2013148620A1 (en) | 2012-03-27 | 2013-10-03 | Bristol-Myers Squibb Company | Benzofuran derivatives for the treatment of hepatitis c |
| WO2013152392A1 (en) | 2012-04-11 | 2013-10-17 | Biota Scientific Management Pty Ltd | Viral polymerase inhibitors |
| WO2013163466A1 (en) * | 2012-04-25 | 2013-10-31 | Presidio Pharmaceuticals, Inc. | Inhibitors of hepatitis c virus |
| CN102690264B (zh) * | 2012-06-20 | 2014-07-02 | 泰山医学院 | 2-苯基-3-取代咪唑并[1,2-a]吡啶类衍生物及其制备方法 |
| WO2014001314A1 (en) | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| AU2013289284B2 (en) | 2012-07-09 | 2017-03-30 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| US8778964B2 (en) | 2012-11-05 | 2014-07-15 | Bayer Pharma Aktiengesellschaft | Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use |
| US8796305B2 (en) | 2012-11-05 | 2014-08-05 | Bayer Pharma Aktiengesellschaft | Carboxy-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US9624214B2 (en) | 2012-11-05 | 2017-04-18 | Bayer Pharma Aktiengesellschaft | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US9126998B2 (en) | 2012-11-05 | 2015-09-08 | Bayer Pharma AG | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US8871754B2 (en) | 2012-11-19 | 2014-10-28 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| LT2925757T (lt) | 2012-11-19 | 2017-12-27 | Novartis Ag | Junginiai ir kompozicijos, skirti parazitinių ligų gydymui |
| US8962651B2 (en) * | 2013-03-13 | 2015-02-24 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9776997B2 (en) | 2013-06-04 | 2017-10-03 | Bayer Pharma Aktiengesellschaft | 3-aryl-substituted imidazo[1,2-A]pyridines and their use |
| TW201609651A (zh) * | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| US9688699B2 (en) | 2014-02-19 | 2017-06-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines |
| CN106715426A (zh) | 2014-03-21 | 2017-05-24 | 拜耳医药股份有限公司 | 氰基取代的咪唑并[1,2‑a]吡啶甲酰胺及其用途 |
| AR099820A1 (es) * | 2014-03-21 | 2016-08-17 | Bristol Myers Squibb Co | Ciano que contiene compuestos de azabenzofuran para el tratamiento de la hepatitis c |
| US9920036B2 (en) * | 2014-03-21 | 2018-03-20 | Bristol-Myers Squibb Company | Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis C |
| CN106459037A (zh) | 2014-05-02 | 2017-02-22 | 拜耳医药股份有限公司 | 用于治疗心血管疾病的N‑(2‑氨基‑5‑氟‑2‑甲基戊基)‑8‑[(2,6‑二氟苄基)氧基]‑2‑甲基咪唑并[1,2‑a]吡啶‑3‑甲酰胺的对映异构体及其二‑和三氟衍生物的对映异构体 |
| EP3180346A1 (en) * | 2014-08-05 | 2017-06-21 | Bristol-Myers Squibb Company | Furopyridine compounds for the treatment of hepatitis c |
| JP2017529401A (ja) * | 2014-09-26 | 2017-10-05 | チャーンジョウ インシュヨン ファーマシューティカル カンパニー，リミティド | Ｎｓ４ｂ阻害剤としてのベンゾフラン類似体 |
| EP3227287B1 (de) | 2014-12-02 | 2019-08-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
| CN108348510B (zh) | 2015-09-17 | 2022-01-04 | 圣母大学 | 针对分枝杆菌感染有用的含有苄胺的杂环化合物以及组合物 |
| WO2018184976A1 (de) | 2017-04-05 | 2018-10-11 | Bayer Pharma Aktiengesellschaft | Substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung |
| RU2019123849A (ru) * | 2019-07-29 | 2021-02-01 | Дзе Брихэм Энд Уимен`З Хоспитал, Инк. | Ингибиторы фактора ингибирования миграции макрофагов |
| WO2024102699A1 (en) * | 2022-11-07 | 2024-05-16 | ELANCO US, Inc. | Guanylate cyclase (gc) stimulator formulations and uses thereof |
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- 2009-09-02 JP JP2011526911A patent/JP2012502099A/ja active Pending
- 2009-09-02 EP EP09792143.1A patent/EP2331502B1/en not_active Not-in-force
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- 2009-09-02 AU AU2009291993A patent/AU2009291993A1/en not_active Abandoned
- 2009-09-02 CN CN200980144810.1A patent/CN102209711B/zh not_active Expired - Fee Related
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Also Published As
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| EP2331502B1 (en) | 2016-03-02 |
| WO2010030538A2 (en) | 2010-03-18 |
| CN102209711B (zh) | 2014-06-18 |
| US20120232099A1 (en) | 2012-09-13 |
| TW201014855A (en) | 2010-04-16 |
| AR073586A1 (es) | 2010-11-17 |
| MX2011002471A (es) | 2011-04-05 |
| JP2012502099A (ja) | 2012-01-26 |
| US8536338B2 (en) | 2013-09-17 |
| KR20110056537A (ko) | 2011-05-30 |
| EP2331502A2 (en) | 2011-06-15 |
| AU2009291993A1 (en) | 2010-03-18 |
| US8198449B2 (en) | 2012-06-12 |
| US20100063068A1 (en) | 2010-03-11 |
| WO2010030538A3 (en) | 2010-05-06 |
| CN102209711A (zh) | 2011-10-05 |
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