CN113508116A - 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 - Google Patents
吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 Download PDFInfo
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- CN113508116A CN113508116A CN202080017586.6A CN202080017586A CN113508116A CN 113508116 A CN113508116 A CN 113508116A CN 202080017586 A CN202080017586 A CN 202080017586A CN 113508116 A CN113508116 A CN 113508116A
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- alkyl
- cycloalkyl
- heteroaryl
- heterocyclyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical class C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000000623 heterocyclic group Chemical group 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 102100028286 Proto-oncogene tyrosine-protein kinase receptor Ret Human genes 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 10
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- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 201000002510 thyroid cancer Diseases 0.000 claims description 5
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical group 0.000 claims description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
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- 239000002184 metal Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
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- 150000003222 pyridines Chemical class 0.000 abstract 2
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- JCFIFHQZMRCJNU-UHFFFAOYSA-N 6-(2-hydroxy-2-methylpropoxy)-4-[6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-3-carbonitrile hydrochloride Chemical compound CC(C)(COC1=CN2C(=C(C=N2)C#N)C(=C1)C3=CN=C(C=C3)C4=CCNCC4)O.Cl JCFIFHQZMRCJNU-UHFFFAOYSA-N 0.000 description 11
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
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- 125000006413 ring segment Chemical group 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- 230000002159 abnormal effect Effects 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
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- ZIEWFIMNFXMKFO-UHFFFAOYSA-N 4-[6-[1-[(3,5-difluorophenyl)methyl]-3,6-dihydro-2H-pyridin-4-yl]pyridin-3-yl]-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile Chemical compound FC=1C=C(CN2CCC(=CC2)C2=NC=C(C=C2)C=2C=3N(C=C(C=2)OCC(C)(C)O)N=CC=3C#N)C=C(C=1)F ZIEWFIMNFXMKFO-UHFFFAOYSA-N 0.000 description 5
- BQZPFGFPTBWTSR-UHFFFAOYSA-N 4-[6-[1-[(5-fluoropyridin-3-yl)methyl]-3,6-dihydro-2H-pyridin-4-yl]pyridin-3-yl]-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile Chemical compound FC=1C=C(C=NC=1)CN1CCC(=CC1)C1=NC=C(C=C1)C=1C=2N(C=C(C=1)OCC(C)(C)O)N=CC=2C#N BQZPFGFPTBWTSR-UHFFFAOYSA-N 0.000 description 5
- DMTSQZPKSAPFJJ-UHFFFAOYSA-N 4-[6-[1-[(6-methoxypyridin-3-yl)methyl]-3,6-dihydro-2H-pyridin-4-yl]pyridin-3-yl]-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=N1)CN1CCC(=CC1)C1=NC=C(C=C1)C=1C=2N(C=C(C=1)C=1C=NN(C=1)C)N=CC=2C#N DMTSQZPKSAPFJJ-UHFFFAOYSA-N 0.000 description 5
- SZBWPXDKDWGDEL-UHFFFAOYSA-N 6-(2-hydroxy-2-methylpropoxy)-4-[6-[1-(2-phenylsulfanylethyl)-3,6-dihydro-2H-pyridin-4-yl]pyridin-3-yl]pyrazolo[1,5-a]pyridine-3-carbonitrile Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=CC(=NC=1)C=1CCN(CC=1)CCSC1=CC=CC=C1)(C)C SZBWPXDKDWGDEL-UHFFFAOYSA-N 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- XZXHXSATPCNXJR-ZIADKAODSA-N nintedanib Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 XZXHXSATPCNXJR-ZIADKAODSA-N 0.000 description 1
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- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229940121610 selpercatinib Drugs 0.000 description 1
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- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- OUFBVDKNEWUFHP-UHFFFAOYSA-N tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)C1CNC2 OUFBVDKNEWUFHP-UHFFFAOYSA-N 0.000 description 1
- VVDCRJGWILREQH-UHFFFAOYSA-N tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(B2OC(C)(C)C(C)(C)O2)=C1 VVDCRJGWILREQH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims (14)
- PCT国内申请,权利要求书已公开。
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CN201910157739.6A CN111635400A (zh) | 2019-03-02 | 2019-03-02 | 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 |
CN2019101577396 | 2019-03-02 | ||
PCT/CN2020/077449 WO2020177668A1 (zh) | 2019-03-02 | 2020-03-02 | 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 |
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CN202080017586.6A Active CN113508116B (zh) | 2019-03-02 | 2020-03-02 | 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 |
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EP (1) | EP3936504A4 (zh) |
CN (2) | CN111635400A (zh) |
WO (1) | WO2020177668A1 (zh) |
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CN111592538A (zh) * | 2019-02-21 | 2020-08-28 | 南京明德新药研发有限公司 | 作为ret抑制剂的脂肪环衍生物 |
MX2021013846A (es) * | 2019-05-14 | 2022-03-22 | Shanghai Hansoh Biomedical Co Ltd | Inhibidor que contiene derivado bicíclico, método de preparación del mismo y uso del mismo. |
CN112851664B (zh) * | 2019-11-12 | 2024-03-29 | 浙江海正药业股份有限公司 | 吡唑[1,5-a]吡啶-3-腈化合物及其在医药上的用途 |
CN112939967B (zh) * | 2019-12-11 | 2024-08-27 | 深圳众格生物科技有限公司 | 吡唑并[1,5-a]吡啶类化合物及其制备方法和应用 |
WO2021129841A1 (zh) * | 2019-12-27 | 2021-07-01 | 浙江同源康医药股份有限公司 | 用作ret激酶抑制剂的化合物及其应用 |
CN114181205B (zh) * | 2020-09-14 | 2024-06-11 | 励缔(杭州)医药科技有限公司 | 吡唑并吡啶类化合物或其盐及其制备方法和用途 |
WO2022083741A1 (zh) * | 2020-10-23 | 2022-04-28 | 上海辉启生物医药科技有限公司 | 吡唑并吡啶类化合物或其盐及其制备方法和用途 |
KR20230107271A (ko) * | 2020-11-13 | 2023-07-14 | 상하이 한서 바이오메디컬 컴퍼니 리미티드 | 이환식 유도체를 포함하는 억제제 유리염기의 결정형, 이의 제조방법 및 용도 |
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US20180133213A1 (en) * | 2016-10-10 | 2018-05-17 | Array Biopharma, Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as ret kinase inhibitors |
WO2018136661A1 (en) * | 2017-01-18 | 2018-07-26 | Andrews Steven W | SUBSTITUTED PYRAZOLO[1,5-a]PYRAZINE COMPOUNDS AS RET KINASE INHIBITORS |
CN108349969A (zh) * | 2015-07-16 | 2018-07-31 | 阵列生物制药公司 | 作为RET激酶抑制剂的取代的吡唑并[1,5-a]吡啶化合物 |
CN111592538A (zh) * | 2019-02-21 | 2020-08-28 | 南京明德新药研发有限公司 | 作为ret抑制剂的脂肪环衍生物 |
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GB0209715D0 (en) | 2002-04-27 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
US8158663B2 (en) | 2006-12-22 | 2012-04-17 | Abbott Laboratories | Compounds as cannabinoid receptor ligands and uses thereof |
TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
ES2871821T3 (es) | 2012-10-25 | 2021-11-02 | Tetra Discovery Partners Llc | Inhibidores de heteroarilo de PDE4 |
SI3186233T1 (sl) | 2014-08-29 | 2022-04-29 | Chdi Foundation, Inc. | Sonde za slikanje proteina huntingtina |
JP2017137276A (ja) | 2016-02-05 | 2017-08-10 | 東洋合成工業株式会社 | 化合物、それを含む組成物及び該組成物を用いたデバイスの製造方法 |
GB201700587D0 (en) | 2017-01-13 | 2017-03-01 | Redag Crop Prot Ltd | Agricultural chemicals |
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CN112939967B (zh) * | 2019-12-11 | 2024-08-27 | 深圳众格生物科技有限公司 | 吡唑并[1,5-a]吡啶类化合物及其制备方法和应用 |
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2019
- 2019-03-02 CN CN201910157739.6A patent/CN111635400A/zh active Pending
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- 2020-03-02 US US17/435,703 patent/US20220135560A1/en active Pending
- 2020-03-02 WO PCT/CN2020/077449 patent/WO2020177668A1/zh unknown
- 2020-03-02 CN CN202080017586.6A patent/CN113508116B/zh active Active
Patent Citations (4)
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CN108349969A (zh) * | 2015-07-16 | 2018-07-31 | 阵列生物制药公司 | 作为RET激酶抑制剂的取代的吡唑并[1,5-a]吡啶化合物 |
US20180133213A1 (en) * | 2016-10-10 | 2018-05-17 | Array Biopharma, Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as ret kinase inhibitors |
WO2018136661A1 (en) * | 2017-01-18 | 2018-07-26 | Andrews Steven W | SUBSTITUTED PYRAZOLO[1,5-a]PYRAZINE COMPOUNDS AS RET KINASE INHIBITORS |
CN111592538A (zh) * | 2019-02-21 | 2020-08-28 | 南京明德新药研发有限公司 | 作为ret抑制剂的脂肪环衍生物 |
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WO2020177668A1 (zh) | 2020-09-10 |
US20220135560A1 (en) | 2022-05-05 |
EP3936504A4 (en) | 2022-10-26 |
EP3936504A1 (en) | 2022-01-12 |
CN111635400A (zh) | 2020-09-08 |
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Effective date of registration: 20240920 Address after: Room 101, 1st Floor, Building 2, No. 50, Lane 63, Faraday Road, Pudong New Area, Shanghai, 201210 Patentee after: Shanghai Daidai Investment Consulting Co.,Ltd. Country or region after: China Address before: 201203 room 126, building 5, No. 334 Edison Road, pilot Free Trade Zone, Pudong New Area, Shanghai Patentee before: Chaluesheng Pharmaceutical Technology (Shanghai) Co.,Ltd. Country or region before: China |