CN101468986A - 一种二氢嘧啶消旋化合物的拆分方法 - Google Patents
一种二氢嘧啶消旋化合物的拆分方法 Download PDFInfo
- Publication number
- CN101468986A CN101468986A CNA2007101606517A CN200710160651A CN101468986A CN 101468986 A CN101468986 A CN 101468986A CN A2007101606517 A CNA2007101606517 A CN A2007101606517A CN 200710160651 A CN200710160651 A CN 200710160651A CN 101468986 A CN101468986 A CN 101468986A
- Authority
- CN
- China
- Prior art keywords
- splitting
- pyrimidin
- dihydro
- handed
- mother liquor
- 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
- 238000000034 method Methods 0.000 title claims abstract description 29
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 238000003756 stirring Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 38
- 239000012452 mother liquor Substances 0.000 claims description 38
- -1 methoxyphenyl Chemical group 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 7
- 235000015320 potassium carbonate Nutrition 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 239000012074 organic phase Substances 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 17
- 230000003287 optical effect Effects 0.000 abstract description 17
- 239000012141 concentrate Substances 0.000 abstract description 3
- 239000010413 mother solution Substances 0.000 abstract 3
- 238000001914 filtration Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 description 31
- YQCGEGQXFHSZHK-UHFFFAOYSA-N 4-formyloxy-2,3-dihydroxy-4-oxobutanoic acid Chemical compound OC(=O)C(O)C(O)C(=O)OC=O YQCGEGQXFHSZHK-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- 239000000284 extract Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 7
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 6
- JSXBRZOZUQITAA-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-6-methyl-2-(1,3-thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylic acid Chemical compound N1C(C)=C(C(O)=O)C(C=2C(=CC(F)=CC=2)Br)N=C1C1=NC=CS1 JSXBRZOZUQITAA-UHFFFAOYSA-N 0.000 description 6
- BUWPWIHTNQGVJD-UHFFFAOYSA-N C(=O)(OC(C1=CC=CC=C1)C1=CC=CC=C1)C(O)C(O)C(=O)OC=O Chemical compound C(=O)(OC(C1=CC=CC=C1)C1=CC=CC=C1)C(O)C(O)C(=O)OC=O BUWPWIHTNQGVJD-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000008014 freezing Effects 0.000 description 6
- 238000007710 freezing Methods 0.000 description 6
- 241000700721 Hepatitis B virus Species 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 101710132601 Capsid protein Proteins 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- CGBKDZMJMIVQQI-UHFFFAOYSA-N methyl 6-methyl-2-(1,3-thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate Chemical compound CC1=C(CN=C(N1)C=1SC=CN1)C(=O)OC CGBKDZMJMIVQQI-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 description 2
- VFHXKGMVRAJJRP-UHFFFAOYSA-N CCC1=C(C(N=C(N1)C2=NC=CS2)C3=C(C=C(C=C3)F)Br)C(=O)O Chemical compound CCC1=C(C(N=C(N1)C2=NC=CS2)C3=C(C=C(C=C3)F)Br)C(=O)O VFHXKGMVRAJJRP-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 208000002672 hepatitis B Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229960001997 adefovir Drugs 0.000 description 1
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960005338 clevudine Drugs 0.000 description 1
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960000980 entecavir Drugs 0.000 description 1
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 description 1
- 229960005311 telbivudine Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2007101606517A CN101468986B (zh) | 2007-12-26 | 2007-12-26 | 一种二氢嘧啶消旋化合物的拆分方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2007101606517A CN101468986B (zh) | 2007-12-26 | 2007-12-26 | 一种二氢嘧啶消旋化合物的拆分方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101468986A true CN101468986A (zh) | 2009-07-01 |
CN101468986B CN101468986B (zh) | 2010-12-29 |
Family
ID=40826821
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2007101606517A Active CN101468986B (zh) | 2007-12-26 | 2007-12-26 | 一种二氢嘧啶消旋化合物的拆分方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101468986B (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9573941B2 (en) | 2013-11-27 | 2017-02-21 | Sunshine Lake Pharma Co., Ltd. | Processes for preparing dihydropyrimidine derivatives and intermediates thereof |
JP2018065830A (ja) * | 2012-02-08 | 2018-04-26 | サノビオン ファーマシューティカルズ インクSunovion Pharmaceuticals Inc. | ヘテロアリール化合物およびそれらの使用方法 |
US10780074B2 (en) | 2017-08-02 | 2020-09-22 | Sunovion Pharmaceuticals Inc. | Compounds and uses thereof |
US10927124B2 (en) | 2016-07-29 | 2021-02-23 | Sunovion Pharmaceuticals Inc. | Compounds and compositions and uses thereof |
US11077090B2 (en) | 2016-07-29 | 2021-08-03 | Sunovion Pharmaceuticals Inc. | Compounds and compositions and uses thereof |
US11136304B2 (en) | 2019-03-14 | 2021-10-05 | Sunovion Pharmaceuticals Inc. | Salts of a heterocyclic compound and crystalline forms, processes for preparing, therapeutic uses, and pharmaceutical compositions thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4931557A (en) * | 1988-10-17 | 1990-06-05 | Eli Lilly And Company | Method of resolving cis 3-amino-4-(2-furyl)vinyl)-1-methoxycarbonylmethyl-azetidin-2-one and di-p-toluoyl-tartaric acid salts thereof |
DE10125131A1 (de) * | 2001-05-23 | 2002-12-05 | Bayer Ag | Verfahren zur Spaltung des Methyl 4-(2-chlor-4-fluorphenyl)-2-(3,5-difluor-2-pyridinyl)-6-methyl-1,4-dihydro-5-pyrmidincarboxylat-Racemats |
FR2853650B1 (fr) * | 2003-04-10 | 2006-07-07 | Merck Sante Sas | Procede de dedoublement d'amines utiles pour le traitement de desordres associes au syndrome d'insulino-resistance |
BRPI0416648A2 (pt) * | 2003-11-20 | 2009-01-13 | Council Scient Ind Res | processo para a preparaÇço de sais quirais farmaceuticamente aceitÁveis de amlodipina |
CN100453542C (zh) * | 2007-04-30 | 2009-01-21 | 广东东阳光药业有限公司 | 2-杂环取代的二氢嘧啶消旋化合物的拆分方法 |
-
2007
- 2007-12-26 CN CN2007101606517A patent/CN101468986B/zh active Active
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018065830A (ja) * | 2012-02-08 | 2018-04-26 | サノビオン ファーマシューティカルズ インクSunovion Pharmaceuticals Inc. | ヘテロアリール化合物およびそれらの使用方法 |
US10556890B2 (en) | 2012-02-08 | 2020-02-11 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
US11332462B2 (en) | 2012-02-08 | 2022-05-17 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
US9573941B2 (en) | 2013-11-27 | 2017-02-21 | Sunshine Lake Pharma Co., Ltd. | Processes for preparing dihydropyrimidine derivatives and intermediates thereof |
US9617252B2 (en) | 2013-11-27 | 2017-04-11 | Sunshine Lake Pharma Co., Ltd. | Processes for preparing dihydropyrimidine derivatives and intermediates thereof |
US9643962B2 (en) | 2013-11-27 | 2017-05-09 | Sunshine Lake Pharma Co., Ltd. | Processes for preparing dihydropyrimidine derivatives and intermediates thereof |
US10927124B2 (en) | 2016-07-29 | 2021-02-23 | Sunovion Pharmaceuticals Inc. | Compounds and compositions and uses thereof |
US11077090B2 (en) | 2016-07-29 | 2021-08-03 | Sunovion Pharmaceuticals Inc. | Compounds and compositions and uses thereof |
US11958862B2 (en) | 2016-07-29 | 2024-04-16 | Sumitomo Pharma America, Inc. | Compounds and compositions and uses thereof |
US10780074B2 (en) | 2017-08-02 | 2020-09-22 | Sunovion Pharmaceuticals Inc. | Compounds and uses thereof |
US11491133B2 (en) | 2017-08-02 | 2022-11-08 | Sunovion Pharmaceuticals Inc. | Heteroaryl-isochroman compounds and uses thereof |
US11136304B2 (en) | 2019-03-14 | 2021-10-05 | Sunovion Pharmaceuticals Inc. | Salts of a heterocyclic compound and crystalline forms, processes for preparing, therapeutic uses, and pharmaceutical compositions thereof |
Also Published As
Publication number | Publication date |
---|---|
CN101468986B (zh) | 2010-12-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101468986B (zh) | 一种二氢嘧啶消旋化合物的拆分方法 | |
CN100453542C (zh) | 2-杂环取代的二氢嘧啶消旋化合物的拆分方法 | |
CN101468987B (zh) | 2-杂环取代的二氢嘧啶消旋化合物的拆分方法 | |
CN102311437A (zh) | 一种抗血小板凝集药替卡格雷的制备方法 | |
Corey et al. | Dual binding modes to the receptor for platelet activating factor (PAF) of anti-PAF trans-2, 5-diarylfurans | |
CN101146812B (zh) | 光学活性铵盐化合物、其制造中间体和制造方法 | |
US10005725B2 (en) | Method for producing pyrrole derivative, and intermediate thereof | |
CN103193779B (zh) | 一种右佐匹克隆的制备方法 | |
CN102143967A (zh) | 阿德福韦酯的纯化方法 | |
CN101798280B (zh) | 一种手性拆分消旋体氨氯地平制备s-(-)-氨氯地平和r-(+)-氨氯地平的方法 | |
CN102850347B (zh) | 一种吡唑衍生物或其盐的拆分方法 | |
CN105524042B (zh) | 一种制备曲格列汀的方法 | |
CN102225885B (zh) | 一种提高α-松油醇光学纯度的方法 | |
CN103304478B (zh) | 一类合成renieramycins型生物碱的中间体及其制备方法 | |
CN1036766A (zh) | 4-取代吡唑[3,4-d]嘧啶衍生物 | |
CN102584860A (zh) | 含吲哚结构的螺杂环化合物及其制备方法 | |
CN101142211A (zh) | 制备光学活性顺式-2-羟甲基-4-(胞嘧啶-1’-基)-1,3-氧硫杂戊环或其药物可接受盐的工艺和方法 | |
CN103965059A (zh) | 一种制备(1r,2s)-2-(3,4-二氟苯基)环丙胺的方法 | |
CN103044361B (zh) | 一种(2r,3s)-环氧化氨基苯丁烷的制备方法 | |
CN103626694A (zh) | 不饱和环胺衍生物、其制备方法及其医药用途 | |
CN102363599A (zh) | 一种西他列汀中间体手性拆分方法 | |
CN101121693A (zh) | 盐酸乐卡地平晶体及制备方法 | |
CN103408520B (zh) | 3-[(2-氟-6-甲氧基)苯基]-5-氯苯酞及其制备方法 | |
JP2021508674A (ja) | 窒素含有縮合三環式化合物及び農業・林業殺虫剤としての使用 | |
CN113603627B (zh) | 一种吡咯酮螺环丙烷化合物的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: DONGYANGGUANG PHARMACEUTICAL CO., LTD., GUANGDONG Free format text: FORMER OWNER: CHINA HONG KONG SOUTH AND NORTH BROTHERS INTERNATIONAL INVESTMENT CO., LTD. Effective date: 20111017 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: HONG KONG, CHINA TO: 523009 DONGGUAN, GUANGDONG PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20111017 Address after: 523009 Songshan Lake Science and Technology Industrial Zone, Dongguan, Guangdong Patentee after: SUNSHINE LAKE PHARMA Co.,Ltd. Address before: No. 6 Bai Bo Road, 13, Yue court, 1, building G, Hongkong, China Patentee before: China Hongkong north and South Brothers International Investment Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for splitting dihydropyrimidine racemic compound Effective date of registration: 20161207 Granted publication date: 20101229 Pledgee: China Development Bank Co. Pledgor: SUNSHINE LAKE PHARMA Co.,Ltd. Registration number: 2016990001089 |
|
PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230606 Granted publication date: 20101229 Pledgee: China Development Bank Co. Pledgor: SUNSHINE LAKE PHARMA Co.,Ltd. Registration number: 2016990001089 |
|
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 523808 No.1, Gongye North Road, Songshanhu Park, Dongguan City, Guangdong Province Patentee after: Guangdong Dongyangguang Pharmaceutical Co.,Ltd. Address before: 523009 Songshanhu science and Technology Industrial Park, Dongguan City, Guangdong Province Patentee before: SUNSHINE LAKE PHARMA Co.,Ltd. |