KR20150072412A - Gdf-8 억제제 - Google Patents
Gdf-8 억제제 Download PDFInfo
- Publication number
- KR20150072412A KR20150072412A KR1020157011251A KR20157011251A KR20150072412A KR 20150072412 A KR20150072412 A KR 20150072412A KR 1020157011251 A KR1020157011251 A KR 1020157011251A KR 20157011251 A KR20157011251 A KR 20157011251A KR 20150072412 A KR20150072412 A KR 20150072412A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridin
- fluoro
- methylphenyl
- pyridine
- imidazo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 0 *C(*C1=C2C=CC=C*2)=C(*=C)C=C1N Chemical compound *C(*C1=C2C=CC=C*2)=C(*=C)C=C1N 0.000 description 25
- WBIIFTDCCJMKGO-CYBMUJFWSA-N CC(C)(C)OC([C@@H](CC1)NCc(cc2)c1cc2Br)=O Chemical compound CC(C)(C)OC([C@@H](CC1)NCc(cc2)c1cc2Br)=O WBIIFTDCCJMKGO-CYBMUJFWSA-N 0.000 description 1
- GCUDANCEKWHJRX-UHFFFAOYSA-N CC(C)Cc1c[nH]cc1 Chemical compound CC(C)Cc1c[nH]cc1 GCUDANCEKWHJRX-UHFFFAOYSA-N 0.000 description 1
- JFFMRVXZGOBGES-UHFFFAOYSA-N CC(C=C1)=NC2C1=CC=CC=C2 Chemical compound CC(C=C1)=NC2C1=CC=CC=C2 JFFMRVXZGOBGES-UHFFFAOYSA-N 0.000 description 1
- NTGFRFRFSXZPCL-VPLBAINYSA-N CC(CC(CC1)C2C(C)=CCC[C@H]2C(CC2)CN3C2NCCC3C(O)Cl)C1F Chemical compound CC(CC(CC1)C2C(C)=CCC[C@H]2C(CC2)CN3C2NCCC3C(O)Cl)C1F NTGFRFRFSXZPCL-VPLBAINYSA-N 0.000 description 1
- DIGGUUKKQCMZPK-UHFFFAOYSA-N CC(CC(CC1)C2NCCCC2C(CC2)CN(C3)C2NC3F)C1F Chemical compound CC(CC(CC1)C2NCCCC2C(CC2)CN(C3)C2NC3F)C1F DIGGUUKKQCMZPK-UHFFFAOYSA-N 0.000 description 1
- HZLUVHUQXMLOBA-UHFFFAOYSA-N CC(CC(CC1)C2NCCCC2C(CC2)N3C2NCC3C(O)O)C1F Chemical compound CC(CC(CC1)C2NCCCC2C(CC2)N3C2NCC3C(O)O)C1F HZLUVHUQXMLOBA-UHFFFAOYSA-N 0.000 description 1
- CIWGPTWXPXXEED-WHKHZWOXSA-N CC(CC(CC1)C2NCCCC2[C@@]2(C)CNC(CN)CC2)C1F Chemical compound CC(CC(CC1)C2NCCCC2[C@@]2(C)CNC(CN)CC2)C1F CIWGPTWXPXXEED-WHKHZWOXSA-N 0.000 description 1
- NOJNEONAABLJFU-UHFFFAOYSA-N CC(CC(N1C)=C(N2)OCC1O)C2[AlH2] Chemical compound CC(CC(N1C)=C(N2)OCC1O)C2[AlH2] NOJNEONAABLJFU-UHFFFAOYSA-N 0.000 description 1
- PVWIKNSPHIDHLV-UHFFFAOYSA-N CC(CC1N(C)CCOC1N1)C1[AlH2] Chemical compound CC(CC1N(C)CCOC1N1)C1[AlH2] PVWIKNSPHIDHLV-UHFFFAOYSA-N 0.000 description 1
- XFZFMAUUZHBQSS-UHFFFAOYSA-N CC1(C)OB(c2cccnc2Cl)OC1(C)C Chemical compound CC1(C)OB(c2cccnc2Cl)OC1(C)C XFZFMAUUZHBQSS-UHFFFAOYSA-N 0.000 description 1
- BFFVTPUNJATJBK-UHFFFAOYSA-N CCC1=CCN=C1 Chemical compound CCC1=CCN=C1 BFFVTPUNJATJBK-UHFFFAOYSA-N 0.000 description 1
- ADCOWUSDRFSARC-UHFFFAOYSA-N CCC1=[N]=C(C=CC(Br)=C2)C2=C1 Chemical compound CCC1=[N]=C(C=CC(Br)=C2)C2=C1 ADCOWUSDRFSARC-UHFFFAOYSA-N 0.000 description 1
- LSZHHNLQHBVAPS-UHFFFAOYSA-N CN(C(CC(C(N)N1)Br)C1OC1)C1=O Chemical compound CN(C(CC(C(N)N1)Br)C1OC1)C1=O LSZHHNLQHBVAPS-UHFFFAOYSA-N 0.000 description 1
- LJAVIQOODZESCJ-UHFFFAOYSA-M CN1C(CC(C(N2)[AlH]I)Br)C2OCC1 Chemical compound CN1C(CC(C(N2)[AlH]I)Br)C2OCC1 LJAVIQOODZESCJ-UHFFFAOYSA-M 0.000 description 1
- JGXCXQPNYWBAGW-UHFFFAOYSA-N CNc(ccc(Br)c1)c1N Chemical compound CNc(ccc(Br)c1)c1N JGXCXQPNYWBAGW-UHFFFAOYSA-N 0.000 description 1
- PCHYYOCUCGCSBU-UHFFFAOYSA-N Cc(cc(cc1)Br)c1N Chemical compound Cc(cc(cc1)Br)c1N PCHYYOCUCGCSBU-UHFFFAOYSA-N 0.000 description 1
- PTKQMVZIOIOUES-UHFFFAOYSA-N Cc(cc(cc1C=N)-c(cccn2)c2Cl)c1[NH-] Chemical compound Cc(cc(cc1C=N)-c(cccn2)c2Cl)c1[NH-] PTKQMVZIOIOUES-UHFFFAOYSA-N 0.000 description 1
- PGHUUQJAEYZEGT-UHFFFAOYSA-N Cc(cc(cc1C=N)Br)c1N Chemical compound Cc(cc(cc1C=N)Br)c1N PGHUUQJAEYZEGT-UHFFFAOYSA-N 0.000 description 1
- HIJFECCZORZNST-UHFFFAOYSA-N Cc1cc(-c(nccc2)c2Cl)ccc1F Chemical compound Cc1cc(-c(nccc2)c2Cl)ccc1F HIJFECCZORZNST-UHFFFAOYSA-N 0.000 description 1
- XQJHFGZOSBKRHB-UHFFFAOYSA-O Cc1cc(-c2ncccc2-c(cc2C(N(C)C)=O)cc(C=N)c2[NH3+])ccc1F Chemical compound Cc1cc(-c2ncccc2-c(cc2C(N(C)C)=O)cc(C=N)c2[NH3+])ccc1F XQJHFGZOSBKRHB-UHFFFAOYSA-O 0.000 description 1
- JIQFYWYGAFBSQB-UHFFFAOYSA-N Cc1cc(-c2ncccc2-c(cc2C=N)cc(C(O)=O)c2N)ccc1F Chemical compound Cc1cc(-c2ncccc2-c(cc2C=N)cc(C(O)=O)c2N)ccc1F JIQFYWYGAFBSQB-UHFFFAOYSA-N 0.000 description 1
- NMMMMNHMDYXAOD-UHFFFAOYSA-N Cc1cc(-c2ncccc2-c2ccc3N=[I]N(CCCN4CCN(C)CC4)c3c2)ccc1F Chemical compound Cc1cc(-c2ncccc2-c2ccc3N=[I]N(CCCN4CCN(C)CC4)c3c2)ccc1F NMMMMNHMDYXAOD-UHFFFAOYSA-N 0.000 description 1
- UGCYKDQPGWMWLO-UHFFFAOYSA-N Cc1ncccc1-c(cc1)cc(F)c1[N+]([O-])=O Chemical compound Cc1ncccc1-c(cc1)cc(F)c1[N+]([O-])=O UGCYKDQPGWMWLO-UHFFFAOYSA-N 0.000 description 1
- GOHBBINNYAWQGO-UHFFFAOYSA-N Clc(cccn1)c1Br Chemical compound Clc(cccn1)c1Br GOHBBINNYAWQGO-UHFFFAOYSA-N 0.000 description 1
- MBAYCIABQSWOKH-UHFFFAOYSA-N Nc(c(C=N)c1)ncc1Br Chemical compound Nc(c(C=N)c1)ncc1Br MBAYCIABQSWOKH-UHFFFAOYSA-N 0.000 description 1
- RQXUDXAAXGXEEU-UHFFFAOYSA-N Nc1ncnc(nc2)c1cc2Br Chemical compound Nc1ncnc(nc2)c1cc2Br RQXUDXAAXGXEEU-UHFFFAOYSA-N 0.000 description 1
- XEKOMASZEAYBSQ-UHFFFAOYSA-N OC(COC1NC2Br)NC1C=C2Br Chemical compound OC(COC1NC2Br)NC1C=C2Br XEKOMASZEAYBSQ-UHFFFAOYSA-N 0.000 description 1
- IUORCZITAPVTAY-UHFFFAOYSA-M OC1NC(CC(C(N2)[AlH]I)Br)C2OC1 Chemical compound OC1NC(CC(C(N2)[AlH]I)Br)C2OC1 IUORCZITAPVTAY-UHFFFAOYSA-M 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N c1cnc2[n]1cccc2 Chemical compound c1cnc2[n]1cccc2 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- DACWQSNZECJJGG-UHFFFAOYSA-N c1n[n](cccc2)c2n1 Chemical compound c1n[n](cccc2)c2n1 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—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
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
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- 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
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- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- 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
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- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D498/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
- C07F9/65038—Five-membered rings having the nitrogen atoms in the positions 1 and 2 condensed with carbocyclic rings or carbocyclic ring systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Neurology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Child & Adolescent Psychology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epidemiology (AREA)
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| US61/710,449 | 2012-10-05 | ||
| PCT/US2013/063585 WO2014055955A1 (en) | 2012-10-05 | 2013-10-04 | Gdf-8 inhibitors |
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| PH12015500719A1 (en) | 2015-05-18 |
| MA38050B1 (fr) | 2017-01-31 |
| US20170342048A1 (en) | 2017-11-30 |
| EP2903978A1 (en) | 2015-08-12 |
| US20160052909A1 (en) | 2016-02-25 |
| US9878992B2 (en) | 2018-01-30 |
| PE20150767A1 (es) | 2015-05-15 |
| MX2015004151A (es) | 2015-07-06 |
| MA38050A1 (fr) | 2016-06-30 |
| AU2013326867B2 (en) | 2018-03-08 |
| JP2016500671A (ja) | 2016-01-14 |
| IL238031A0 (en) | 2015-05-31 |
| CA2887203A1 (en) | 2014-04-10 |
| US9145433B2 (en) | 2015-09-29 |
| ZA201503041B (en) | 2017-11-29 |
| WO2014055955A1 (en) | 2014-04-10 |
| CN104837832A (zh) | 2015-08-12 |
| US9518040B2 (en) | 2016-12-13 |
| JP2019048841A (ja) | 2019-03-28 |
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