JP2014523917A5 - - Google Patents
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- Publication number
- JP2014523917A5 JP2014523917A5 JP2014521931A JP2014521931A JP2014523917A5 JP 2014523917 A5 JP2014523917 A5 JP 2014523917A5 JP 2014521931 A JP2014521931 A JP 2014521931A JP 2014521931 A JP2014521931 A JP 2014521931A JP 2014523917 A5 JP2014523917 A5 JP 2014523917A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- polymorph
- thf
- formula
- ray powder
- 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.)
- Withdrawn
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 27
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 24
- 239000013078 crystal Substances 0.000 claims 23
- 235000019439 ethyl acetate Nutrition 0.000 claims 20
- 238000000634 powder X-ray diffraction Methods 0.000 claims 19
- 239000012046 mixed solvent Substances 0.000 claims 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 16
- 239000002904 solvent Substances 0.000 claims 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 13
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 10
- 229940011051 isopropyl acetate Drugs 0.000 claims 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 238000002844 melting Methods 0.000 claims 5
- 230000008018 melting Effects 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000011261 inert gas Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 230000002269 spontaneous effect Effects 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 208000007502 anemia Diseases 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000001556 precipitation Methods 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- -1 Synthesis of Compound 3 Compound Chemical class 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- ZMQBBPRAZLACCW-UHFFFAOYSA-N acetic acid;dichloromethane Chemical compound ClCCl.CC(O)=O ZMQBBPRAZLACCW-UHFFFAOYSA-N 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 229940125898 compound 5 Drugs 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 229940090181 propyl acetate Drugs 0.000 claims 2
- 239000002002 slurry Substances 0.000 claims 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 claims 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 1
- 208000002903 Thalassemia Diseases 0.000 claims 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000004533 oil dispersion Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 238000004062 sedimentation Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 208000037905 systemic hypertension Diseases 0.000 claims 1
- OSWULUXZFOQIRU-UHFFFAOYSA-N tert-butyl 2-aminoacetate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CN OSWULUXZFOQIRU-UHFFFAOYSA-N 0.000 claims 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110215826 | 2011-07-29 | ||
| CN201110215826.6 | 2011-07-29 | ||
| CN201110219607.5 | 2011-08-02 | ||
| CN201110219607 | 2011-08-02 | ||
| CN201110232754 | 2011-08-15 | ||
| CN201110232754.6 | 2011-08-15 | ||
| PCT/CN2012/079361 WO2013017063A1 (en) | 2011-07-29 | 2012-07-30 | Stable polymorphic forms of compound as hypoxia mimetics, and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014523917A JP2014523917A (ja) | 2014-09-18 |
| JP2014523917A5 true JP2014523917A5 (enExample) | 2015-09-10 |
Family
ID=47628644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014521931A Withdrawn JP2014523917A (ja) | 2011-07-29 | 2012-07-30 | 低酸素模倣剤としての化合物の安定な多形体、およびその使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9238637B2 (enExample) |
| EP (1) | EP2736892A4 (enExample) |
| JP (1) | JP2014523917A (enExample) |
| KR (1) | KR20140076549A (enExample) |
| CN (1) | CN103946218B (enExample) |
| AU (1) | AU2012289563A1 (enExample) |
| CA (1) | CA2843240A1 (enExample) |
| IL (1) | IL230682A0 (enExample) |
| WO (1) | WO2013017063A1 (enExample) |
| ZA (1) | ZA201401448B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2959688C (en) | 2014-09-02 | 2024-02-27 | Sunshine Lake Pharma Co., Ltd. | Quinolone compounds and their use to treat diseases related to hypoxia inducible factor and/or erythropoietin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110113664A (ko) * | 2006-08-29 | 2011-10-17 | 테바 파마슈티컬 인더스트리즈 리미티드 | 비타민 ｄ 및 코르티코스테로이드를 포함하는 약학 조성물 |
| WO2009100250A1 (en) * | 2008-02-05 | 2009-08-13 | Fibrogen, Inc. | Chromene derivatives and use thereof as hif hydroxylase activity inhibitors |
| EP2454249B1 (en) * | 2009-07-15 | 2018-09-19 | Beijing Betta Pharmaceuticals Co., Ltd | Compounds as hypoxia mimetics, and compositions, and uses thereof |
-
2012
- 2012-07-30 EP EP12819230.9A patent/EP2736892A4/en not_active Withdrawn
- 2012-07-30 KR KR1020147005160A patent/KR20140076549A/ko not_active Withdrawn
- 2012-07-30 CA CA2843240A patent/CA2843240A1/en not_active Abandoned
- 2012-07-30 US US14/166,203 patent/US9238637B2/en not_active Expired - Fee Related
- 2012-07-30 JP JP2014521931A patent/JP2014523917A/ja not_active Withdrawn
- 2012-07-30 CN CN201280036645.XA patent/CN103946218B/zh not_active Expired - Fee Related
- 2012-07-30 WO PCT/CN2012/079361 patent/WO2013017063A1/en not_active Ceased
- 2012-07-30 AU AU2012289563A patent/AU2012289563A1/en not_active Abandoned
-
2014
- 2014-01-28 IL IL230682A patent/IL230682A0/en unknown
- 2014-02-25 ZA ZA2014/01448A patent/ZA201401448B/en unknown
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