CN102491974B - 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 - Google Patents
1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 Download PDFInfo
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- CN102491974B CN102491974B CN201110414004.0A CN201110414004A CN102491974B CN 102491974 B CN102491974 B CN 102491974B CN 201110414004 A CN201110414004 A CN 201110414004A CN 102491974 B CN102491974 B CN 102491974B
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- compound
- pyrazolo
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- reaction
- fluorobenzyl
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- 238000000034 method Methods 0.000 title abstract description 8
- 230000002194 synthesizing effect Effects 0.000 title abstract description 8
- DQASIYVADJWVLY-UHFFFAOYSA-N [1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridine-3-carboximidoyl]azanium;chloride Chemical compound Cl.C12=NC=CC=C2C(C(=N)N)=NN1CC1=CC=CC=C1F DQASIYVADJWVLY-UHFFFAOYSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 239000007810 chemical reaction solvent Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 10
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 abstract description 7
- WXXSNCNJFUAIDG-UHFFFAOYSA-N riociguat Chemical compound N1=C(N)C(N(C)C(=O)OC)=C(N)N=C1C(C1=CC=CN=C11)=NN1CC1=CC=CC=C1F WXXSNCNJFUAIDG-UHFFFAOYSA-N 0.000 abstract description 4
- 229960000529 riociguat Drugs 0.000 abstract description 4
- TYXAGVKIICJXGF-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-b]pyridine Chemical compound N1=CC=CC2=C(I)NN=C21 TYXAGVKIICJXGF-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 208000001435 Thromboembolism Diseases 0.000 abstract 1
- AVPMRIWGOGRNBF-UHFFFAOYSA-N [bromo(fluoro)methyl]benzene Chemical compound FC(Br)C1=CC=CC=C1 AVPMRIWGOGRNBF-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 229960002587 amitraz Drugs 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 208000002815 pulmonary hypertension Diseases 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RRLMPLDPCKRASL-ONEGZZNKSA-N (e)-3-(dimethylamino)prop-2-enal Chemical compound CN(C)\C=C\C=O RRLMPLDPCKRASL-ONEGZZNKSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FYCVIFRMFLWTJR-NKUHCKNESA-N CC[C@H](C)C(C(N(Cc1ccccc1F)N=C)=N)N Chemical compound CC[C@H](C)C(C(N(Cc1ccccc1F)N=C)=N)N FYCVIFRMFLWTJR-NKUHCKNESA-N 0.000 description 1
- HQUSARUJTRVERL-NFJWQWPMSA-N C[C@@H](C(C)C(N(Cc(cccc1)c1F)N=C)=N)C=N Chemical compound C[C@@H](C(C)C(N(Cc(cccc1)c1F)N=C)=N)C=N HQUSARUJTRVERL-NFJWQWPMSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- CSUUGTRFBZTTQW-UHFFFAOYSA-N N#Cc1n[n](Cc(cccc2)c2F)c2c1cccn2 Chemical compound N#Cc1n[n](Cc(cccc2)c2F)c2c1cccn2 CSUUGTRFBZTTQW-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009424 thromboembolic effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110414004.0A CN102491974B (zh) | 2011-12-12 | 2011-12-12 | 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 |
| IN5281DEN2014 IN2014DN05281A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2011-12-12 | 2012-11-28 | |
| PCT/CN2012/085451 WO2013086935A1 (zh) | 2011-12-12 | 2012-11-28 | 1-（2-氟苄基）-1H -吡唑并[3，4- b]吡啶-3 -甲脒盐酸盐的合成方法 |
| JP2014545075A JP5791825B2 (ja) | 2011-12-12 | 2012-11-28 | １−（２−フルオロベンジル）−１Ｈ−ピラゾロ［３，４−ｂ］ピリジン−３−ホルムアミジン塩酸塩の合成方法 |
| DE112012005176.9T DE112012005176B4 (de) | 2011-12-12 | 2012-11-28 | Verfahren zum Synthetisieren von 1-(2-FluorbenzyI)-1H-pyrazolo[3,4-b]pyridin-3-formamidin-hydrochlorid |
| US14/364,040 US8957210B2 (en) | 2011-12-12 | 2012-11-28 | Method for synthesizing 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-formamidine hydrochloride |
| IL233066A IL233066B (en) | 2011-12-12 | 2014-06-10 | Method for preparing 1-(2-fluorobenzyl)-h1-pyrazolo[b-3,4]pyridine-3-formamidine hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110414004.0A CN102491974B (zh) | 2011-12-12 | 2011-12-12 | 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102491974A CN102491974A (zh) | 2012-06-13 |
| CN102491974B true CN102491974B (zh) | 2013-08-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110414004.0A Active CN102491974B (zh) | 2011-12-12 | 2011-12-12 | 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104086545A (zh) * | 2014-07-29 | 2014-10-08 | 安徽联创药物化学有限公司 | 1-(2-氟苄基)-1H-吡唑并[3,4-b]吡啶-3-甲脒盐酸盐的合成方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491974B (zh) | 2011-12-12 | 2013-08-07 | 南京药石药物研发有限公司 | 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 |
| CN105237531A (zh) * | 2015-10-15 | 2016-01-13 | 湖南华腾制药有限公司 | 一种利奥西呱中间体的制备方法及其中间体化合物 |
| AU2016371762A1 (en) | 2015-12-14 | 2018-06-21 | Cyclerion Therapeutics, Inc. | Use of sGC stimulators for the treatment of gastrointestinal sphincter dysfunction |
| WO2018111795A2 (en) | 2016-12-13 | 2018-06-21 | Ironwood Pharmaceuticals, Inc. | Use of sgc stimulators for the treatment of esophageal motility disorders |
| CA3103676A1 (en) | 2018-07-11 | 2020-01-16 | Cyclerion Therapeutics, Inc. | Use of sgc stimulators for the treatment of mitochonrial disorders |
| CN115947689B (zh) * | 2022-09-23 | 2025-08-29 | 湖南华腾制药有限公司 | 一种连续流微反应器合成利奥西呱中间体的方法 |
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| US20020173514A1 (en) * | 2000-11-22 | 2002-11-21 | Johannes-Peter Stasch | Pyridine-substituted pyrazolopyridine derivatives |
| CN1330649C (zh) * | 2002-05-08 | 2007-08-08 | 拜耳医药保健股份公司 | 氨基甲酸酯－取代的吡唑并吡啶类化合物 |
| CN101648909A (zh) * | 2009-09-14 | 2010-02-17 | 南京第一农药集团有限公司 | 一种氯代吡啶在无配体钯催化下制备氰基吡啶的方法 |
| CN102149712A (zh) * | 2008-02-29 | 2011-08-10 | 阵列生物制药公司 | 吡唑并[3，4-b]吡啶Raf抑制剂 |
| WO2011149921A1 (en) * | 2010-05-27 | 2011-12-01 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
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| US20100113472A1 (en) | 2008-11-03 | 2010-05-06 | Chemocentryx, Inc. | Compounds for the treatment of osteoporosis and cancers |
| US20110225969A1 (en) | 2010-03-19 | 2011-09-22 | Gm Global Technology Operations, Inc. | Compressor bypass to exhaust for particulate trap regeneration |
| AU2011257336B2 (en) | 2010-05-26 | 2015-11-19 | Adverio Pharma Gmbh | The use of sGC stimulators, sGC activators, alone and combinations with PDE5 inhibitors for the treatment of systemic sclerosis (SSc). |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| PH12013501941A1 (en) | 2011-04-22 | 2021-06-23 | Pfizer | Pyrazolospiroketone derivatives for use as acetyl - coa carboxylase inhibitors |
| CN104039784B (zh) * | 2011-09-02 | 2017-08-22 | 拜耳知识产权有限责任公司 | 取代的增环嘧啶及其用途 |
| CN102491974B (zh) | 2011-12-12 | 2013-08-07 | 南京药石药物研发有限公司 | 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 |
-
2011
- 2011-12-12 CN CN201110414004.0A patent/CN102491974B/zh active Active
-
2012
- 2012-11-28 IN IN5281DEN2014 patent/IN2014DN05281A/en unknown
- 2012-11-28 JP JP2014545075A patent/JP5791825B2/ja active Active
- 2012-11-28 US US14/364,040 patent/US8957210B2/en active Active
- 2012-11-28 WO PCT/CN2012/085451 patent/WO2013086935A1/zh active Application Filing
- 2012-11-28 DE DE112012005176.9T patent/DE112012005176B4/de active Active
-
2014
- 2014-06-10 IL IL233066A patent/IL233066B/en active IP Right Grant
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20020173514A1 (en) * | 2000-11-22 | 2002-11-21 | Johannes-Peter Stasch | Pyridine-substituted pyrazolopyridine derivatives |
| CN1330649C (zh) * | 2002-05-08 | 2007-08-08 | 拜耳医药保健股份公司 | 氨基甲酸酯－取代的吡唑并吡啶类化合物 |
| CN102149712A (zh) * | 2008-02-29 | 2011-08-10 | 阵列生物制药公司 | 吡唑并[3，4-b]吡啶Raf抑制剂 |
| CN101648909A (zh) * | 2009-09-14 | 2010-02-17 | 南京第一农药集团有限公司 | 一种氯代吡啶在无配体钯催化下制备氰基吡啶的方法 |
| WO2011149921A1 (en) * | 2010-05-27 | 2011-12-01 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
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| Title |
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| Discovery of Riociguat (BAY 63-2521): A Potent, Oral Stimulator of Soluble Guanylate Cyclase for the Treatment of Pulmonary Hypertension;Joachim Mittendorf 等;《ChemMedChem》;20090504;第4卷(第5期);第857、860-864页 * |
| JoachimMittendorf等.DiscoveryofRiociguat(BAY63-2521):APotent Oral Stimulator of Soluble Guanylate Cyclase for the Treatment of Pulmonary Hypertension.《ChemMedChem》.2009 |
| 李亮 等.肺动脉高压治疗药riociguat的合成.《中国药物化学杂志》.2011,第21卷(第2期),第120-121页. |
| 肺动脉高压治疗药riociguat的合成;李亮 等;《中国药物化学杂志》;20110420;第21卷(第2期);第120-121页 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104086545A (zh) * | 2014-07-29 | 2014-10-08 | 安徽联创药物化学有限公司 | 1-(2-氟苄基)-1H-吡唑并[3,4-b]吡啶-3-甲脒盐酸盐的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE112012005176T5 (de) | 2014-08-28 |
| DE112012005176B4 (de) | 2018-10-11 |
| IL233066B (en) | 2019-01-31 |
| IL233066A0 (en) | 2014-07-31 |
| CN102491974A (zh) | 2012-06-13 |
| JP5791825B2 (ja) | 2015-10-07 |
| US8957210B2 (en) | 2015-02-17 |
| US20140309425A1 (en) | 2014-10-16 |
| WO2013086935A1 (zh) | 2013-06-20 |
| IN2014DN05281A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-04-03 |
| JP2015500248A (ja) | 2015-01-05 |
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