CN107033058A - 氮杂环高选择性醛的合成工艺 - Google Patents
氮杂环高选择性醛的合成工艺 Download PDFInfo
- Publication number
- CN107033058A CN107033058A CN201710348156.2A CN201710348156A CN107033058A CN 107033058 A CN107033058 A CN 107033058A CN 201710348156 A CN201710348156 A CN 201710348156A CN 107033058 A CN107033058 A CN 107033058A
- Authority
- CN
- China
- Prior art keywords
- benzyl
- formaldehyde
- pyrroles
- synthesis technique
- azacyclo
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 25
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 24
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 5
- 150000003053 piperidines Chemical class 0.000 claims abstract description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 150000003233 pyrroles Chemical class 0.000 claims abstract description 12
- 150000003217 pyrazoles Chemical class 0.000 claims abstract description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 150000001299 aldehydes Chemical class 0.000 claims description 20
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- -1 1- benzyl pyrroles Azoles Chemical class 0.000 claims description 17
- FNEQHKCQXDKYEO-UHFFFAOYSA-N 1-benzylpyrrole Chemical class C1=CC=CN1CC1=CC=CC=C1 FNEQHKCQXDKYEO-UHFFFAOYSA-N 0.000 claims description 13
- AKQAJYLKBCWJBV-UHFFFAOYSA-N 1-benzylpyrazole Chemical class C1=CC=NN1CC1=CC=CC=C1 AKQAJYLKBCWJBV-UHFFFAOYSA-N 0.000 claims description 12
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 12
- 125000006278 bromobenzyl group Chemical group 0.000 claims description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 9
- JNHZZTKKFSPICX-UHFFFAOYSA-N 1-benzylpyrrole-2-carbaldehyde Chemical compound O=CC1=CC=CN1CC1=CC=CC=C1 JNHZZTKKFSPICX-UHFFFAOYSA-N 0.000 claims description 7
- CCOXWRVWKFVFDG-UHFFFAOYSA-N pyrimidine-2-carbaldehyde Chemical compound O=CC1=NC=CC=N1 CCOXWRVWKFVFDG-UHFFFAOYSA-N 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 2
- BOGSOFADOWIECK-UHFFFAOYSA-N [N].C=1C=NNC=1 Chemical group [N].C=1C=NNC=1 BOGSOFADOWIECK-UHFFFAOYSA-N 0.000 claims description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
- 238000007867 post-reaction treatment Methods 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- 206010011224 Cough Diseases 0.000 claims 3
- KTFGWHSLIOZEKH-UHFFFAOYSA-N 5-benzyl-1h-pyrazole Chemical compound C=1C=CC=CC=1CC1=CC=NN1 KTFGWHSLIOZEKH-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 10
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 230000000977 initiatory effect Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- 238000003756 stirring Methods 0.000 description 45
- 238000010791 quenching Methods 0.000 description 24
- 230000000171 quenching effect Effects 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 10
- 238000010792 warming Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 150000005525 1-benzylpiperazines Chemical class 0.000 description 1
- SGIBOXBBPQRZDM-UHFFFAOYSA-N 1-benzylpiperidine-4-carbaldehyde Chemical class C1CC(C=O)CCN1CC1=CC=CC=C1 SGIBOXBBPQRZDM-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl chloride Substances ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- ZTRPYTHOEREHEN-UHFFFAOYSA-N piperazine pyridine Chemical compound N1CCNCC1.N1=CC=CC=C1.N1=CC=CC=C1 ZTRPYTHOEREHEN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/48—Aldehydo radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710348156.2A CN107033058A (zh) | 2017-05-17 | 2017-05-17 | 氮杂环高选择性醛的合成工艺 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710348156.2A CN107033058A (zh) | 2017-05-17 | 2017-05-17 | 氮杂环高选择性醛的合成工艺 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN107033058A true CN107033058A (zh) | 2017-08-11 |
Family
ID=59538586
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710348156.2A Pending CN107033058A (zh) | 2017-05-17 | 2017-05-17 | 氮杂环高选择性醛的合成工艺 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107033058A (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102532049A (zh) * | 2011-12-22 | 2012-07-04 | 凯莱英医药集团(天津)股份有限公司 | 一种制备2-醛基恶唑的方法 |
WO2012107488A2 (en) * | 2011-02-08 | 2012-08-16 | Universita' Degli Studi Di Milano | Metal-free photosensitizers |
US20140200215A1 (en) * | 2013-01-15 | 2014-07-17 | Intermune, Inc. | Lysophosphatidic acid receptor antagonists |
-
2017
- 2017-05-17 CN CN201710348156.2A patent/CN107033058A/zh active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012107488A2 (en) * | 2011-02-08 | 2012-08-16 | Universita' Degli Studi Di Milano | Metal-free photosensitizers |
CN102532049A (zh) * | 2011-12-22 | 2012-07-04 | 凯莱英医药集团(天津)股份有限公司 | 一种制备2-醛基恶唑的方法 |
US20140200215A1 (en) * | 2013-01-15 | 2014-07-17 | Intermune, Inc. | Lysophosphatidic acid receptor antagonists |
Non-Patent Citations (2)
Title |
---|
JAMES E. TAYLOR等: "Friedel-Crafts Acylation of Pyrroles and Indoles using 1,5- Diazabicyclo[4.3.0]non-5-ene (DBN) as a Nucleophilic Catalyst", 《ORG. LETT.》 * |
S.NARAYANA MURTHY等: "o-Iodoxybenzoic acid (IBX): a versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water", 《TETRAHEDRON LETTERS》 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TW201922757A (zh) | 製備6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈的方法 | |
TW201609696A (zh) | 用於製備3-(3-氯-1h-吡唑-1-基)吡啶的方法(三) | |
CN102245575B (zh) | 制备取代的5‑甲氧基甲基吡啶‑2,3‑二甲酸衍生物的方法 | |
US20160257667A1 (en) | Synthesis of intermediates in the preparation of alk inhibitor | |
US9593101B2 (en) | Avanafil preparation method | |
US11161851B2 (en) | Processes to produce acalabrutinib | |
CN104447234A (zh) | (3r,4r)-4-(3,4-二甲氧基苄基)-3-(4-羟基-3-甲氧基苄基)-二氢呋喃的制备方法 | |
CN107033058A (zh) | 氮杂环高选择性醛的合成工艺 | |
CN105732619A (zh) | 一种5,6,7,8-四氢吡啶并[2,3-d]嘧啶类化合物的合成方法 | |
CN104356115A (zh) | 一种4-[(3-氯-4-甲氧基苄基)氨基]-2-[2-(羟甲基)-1-吡咯烷基]嘧啶-5-羧酸乙酯的制备方法 | |
CN109651367B (zh) | 一种制备1,4-二氢喹啉及吡咯并[1,2-a]喹啉类化合物的方法 | |
CN105272966A (zh) | Alk抑制剂克唑替尼及其类似物或盐的制备方法 | |
CN107922341A (zh) | 新型的4‑苯并偶氮宁衍生物的制造方法 | |
CN103992307B (zh) | 一种克里唑替尼的制备方法 | |
CN104788353B (zh) | 一种合成4‑氧代‑l‑脯氨酸衍生物的方法 | |
CN106588761B (zh) | 一种氯雷他定中间体的合成方法 | |
CN109020977B (zh) | 一种Acalabrutinib的制备方法 | |
CN105330690B (zh) | 一种药物中间体芳基酮膦酸酯化合物的合成方法 | |
CN107915653A (zh) | 催化酯和胺进行反应制备酰胺的方法 | |
CN110746345B (zh) | 2-(2-氨基-5-溴-苯甲酰基)吡啶的合成方法 | |
CN106083693A (zh) | N‑邻苯二甲酰基对‑(二羟乙基)氨基‑l‑苯丙氨酸乙酯的合成工艺 | |
CN109608454B (zh) | 一种合成6氢-吡啶[1,2-c]喹唑啉-6-酮类化合物的新方法 | |
CN106632019A (zh) | 一种多取代吡啶的制备方法 | |
CN104860881A (zh) | 8-(硝基甲基)喹啉类化合物和8-甲氨基四氢喹啉类化合物的合成方法 | |
CN105153211B (zh) | 一种合成1‑(N‑Boc‑4‑哌啶)‑4‑吡唑硼酸频哪醇酯的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20181213 Address after: 462499 Chemical Park of Southern Qingdao Road, Wuyang County Industrial Agglomeration Area, Luohe City, Henan Province Applicant after: Wuyang lelexin Biological Medicine Co Ltd Address before: 215634 Building D, No. 7 Guangdong Road, Zhangjiagang Free Trade Zone, Suzhou City, Jiangsu Province, 3rd Floor Applicant before: Jiangsu Swithin Biological Medicine Engineering Research Center Co., Ltd. Applicant before: Zhangjiagang Weisheng Biological Pharmaceutical Co., Ltd. Applicant before: Wuyang lelexin Biological Medicine Co Ltd |
|
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170811 |