JP2014159427A5 - - Google Patents
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- Publication number
- JP2014159427A5 JP2014159427A5 JP2014045733A JP2014045733A JP2014159427A5 JP 2014159427 A5 JP2014159427 A5 JP 2014159427A5 JP 2014045733 A JP2014045733 A JP 2014045733A JP 2014045733 A JP2014045733 A JP 2014045733A JP 2014159427 A5 JP2014159427 A5 JP 2014159427A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ion
- dihydropyridin
- piperazine
- carboxylate
- 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.)
- Granted
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 75
- -1 2,3-difluorophenyl Chemical group 0.000 claims 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 21
- 101001046870 Homo sapiens Hypoxia-inducible factor 1-alpha Proteins 0.000 claims 12
- 102100022875 Hypoxia-inducible factor 1-alpha Human genes 0.000 claims 12
- 229940078467 Prolyl hydroxylase inhibitor Drugs 0.000 claims 12
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 9
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 9
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 9
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 3
- 206010021143 Hypoxia Diseases 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 3
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 229940006460 bromide ion Drugs 0.000 claims 3
- 150000007942 carboxylates Chemical class 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 3
- 230000007954 hypoxia Effects 0.000 claims 3
- 230000001939 inductive effect Effects 0.000 claims 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 3
- 229940006461 iodide ion Drugs 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- 229940085991 phosphate ion Drugs 0.000 claims 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 3
- 235000002906 tartaric acid Nutrition 0.000 claims 3
- 239000011975 tartaric acid Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000007502 anemia Diseases 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 0 *C*(C=CC(C*(CC1)CCN1C(O*)=O)=C1O)C1=O Chemical compound *C*(C=CC(C*(CC1)CCN1C(O*)=O)=C1O)C1=O 0.000 description 2
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25891409P | 2009-11-06 | 2009-11-06 | |
| US25891809P | 2009-11-06 | 2009-11-06 | |
| US61/258,914 | 2009-11-06 | ||
| US61/258,918 | 2009-11-06 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537236A Division JP5627040B2 (ja) | 2009-11-06 | 2010-11-05 | 低酸素誘導因子−１αの安定化を増大させるための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014159427A JP2014159427A (ja) | 2014-09-04 |
| JP2014159427A5 true JP2014159427A5 (https=) | 2014-10-16 |
| JP5865411B2 JP5865411B2 (ja) | 2016-02-17 |
Family
ID=43970365
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537236A Expired - Fee Related JP5627040B2 (ja) | 2009-11-06 | 2010-11-05 | 低酸素誘導因子−１αの安定化を増大させるための方法 |
| JP2012537240A Expired - Fee Related JP5591939B2 (ja) | 2009-11-06 | 2010-11-05 | 大腸炎を治療するための組成物および方法 |
| JP2012537237A Expired - Fee Related JP5599467B2 (ja) | 2009-11-06 | 2010-11-05 | プロリルヒドロキシラーゼ阻害剤 |
| JP2014045734A Withdrawn JP2014139206A (ja) | 2009-11-06 | 2014-03-07 | プロリルヒドロキシラーゼ阻害剤 |
| JP2014045733A Expired - Fee Related JP5865411B2 (ja) | 2009-11-06 | 2014-03-07 | 低酸素誘導因子−１αの安定化を増大させるための方法 |
| JP2014155145A Expired - Fee Related JP5961665B2 (ja) | 2009-11-06 | 2014-07-30 | 大腸炎を治療するための組成物および方法 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537236A Expired - Fee Related JP5627040B2 (ja) | 2009-11-06 | 2010-11-05 | 低酸素誘導因子−１αの安定化を増大させるための方法 |
| JP2012537240A Expired - Fee Related JP5591939B2 (ja) | 2009-11-06 | 2010-11-05 | 大腸炎を治療するための組成物および方法 |
| JP2012537237A Expired - Fee Related JP5599467B2 (ja) | 2009-11-06 | 2010-11-05 | プロリルヒドロキシラーゼ阻害剤 |
| JP2014045734A Withdrawn JP2014139206A (ja) | 2009-11-06 | 2014-03-07 | プロリルヒドロキシラーゼ阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014155145A Expired - Fee Related JP5961665B2 (ja) | 2009-11-06 | 2014-07-30 | 大腸炎を治療するための組成物および方法 |
Country Status (28)
| Country | Link |
|---|---|
| US (11) | US8309537B2 (https=) |
| EP (9) | EP2649998B1 (https=) |
| JP (6) | JP5627040B2 (https=) |
| KR (8) | KR20120088833A (https=) |
| CN (3) | CN102595896B (https=) |
| AU (3) | AU2010314976B2 (https=) |
| BR (3) | BR112012010766A2 (https=) |
| CA (3) | CA2774039A1 (https=) |
| DK (4) | DK2853265T3 (https=) |
| ES (5) | ES2541613T3 (https=) |
| HK (1) | HK1208806A1 (https=) |
| HR (3) | HRP20130691T1 (https=) |
| HU (1) | HUE026109T2 (https=) |
| IL (4) | IL219612A (https=) |
| IN (3) | IN2012DN04949A (https=) |
| MX (4) | MX2012005273A (https=) |
| MY (3) | MY160066A (https=) |
| NO (1) | NO2853265T3 (https=) |
| NZ (4) | NZ600396A (https=) |
| PH (3) | PH12012500790A1 (https=) |
| PL (4) | PL2496084T3 (https=) |
| PT (4) | PT2853265T (https=) |
| RS (3) | RS54010B1 (https=) |
| RU (3) | RU2518071C2 (https=) |
| SI (2) | SI2649998T1 (https=) |
| SM (1) | SMT201300096B (https=) |
| WO (3) | WO2011057112A1 (https=) |
| ZA (1) | ZA201204104B (https=) |
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| WO2012170439A1 (en) * | 2011-06-06 | 2012-12-13 | The Ohio State University | Methods for stabilizing hypoxia inducible factor-2 alpha as a method for treating cancer |
| NO2686520T3 (https=) | 2011-06-06 | 2018-03-17 | ||
| WO2013056240A1 (en) | 2011-10-13 | 2013-04-18 | Aerpio Therapeutics, Inc. | Methods for treating vascular leak syndrome and cancer |
| EP3935944A1 (en) * | 2013-03-15 | 2022-01-12 | University Of Southern California, USC Stevens | Compounds for the treatment of musculoskeletal diseases |
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