CN1073946A - 制备脯氨酸硼酸酯的方法 - Google Patents
制备脯氨酸硼酸酯的方法 Download PDFInfo
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- CN1073946A CN1073946A CN92113215A CN92113215A CN1073946A CN 1073946 A CN1073946 A CN 1073946A CN 92113215 A CN92113215 A CN 92113215A CN 92113215 A CN92113215 A CN 92113215A CN 1073946 A CN1073946 A CN 1073946A
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- Prior art keywords
- formula
- glycol
- boric acid
- pinane
- ester
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- 238000000034 method Methods 0.000 title claims abstract description 94
- OHVALSOULVZORC-WCCKRBBISA-N B(O)(O)O.N1[C@H](C(=O)O)CCC1 Chemical compound B(O)(O)O.N1[C@H](C(=O)O)CCC1 OHVALSOULVZORC-WCCKRBBISA-N 0.000 title claims abstract description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 172
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 claims abstract description 124
- 239000004327 boric acid Substances 0.000 claims abstract description 98
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 83
- 229930006728 pinane Natural products 0.000 claims abstract description 64
- -1 pinane glycol borate ester Chemical class 0.000 claims abstract description 59
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 37
- 125000006239 protecting group Chemical group 0.000 claims abstract description 30
- 150000002148 esters Chemical class 0.000 claims abstract description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
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- 108091007433 antigens Proteins 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000006251 butylcarbonyl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- PMPYSSMGWFNAAQ-UHFFFAOYSA-N dichloromethane;n,n-diethylethanamine Chemical compound ClCCl.CCN(CC)CC PMPYSSMGWFNAAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- HYXDULZRFHVIDQ-UHFFFAOYSA-N ethyl acetate;methane Chemical compound C.CCOC(C)=O HYXDULZRFHVIDQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- IZUFUXNHBBCTCA-UHFFFAOYSA-N lithium;1-methylpiperidine Chemical compound [Li].CN1CCCCC1 IZUFUXNHBBCTCA-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- VQEVKEKJZVEGPH-UHFFFAOYSA-N lithium;chloromethane Chemical compound [Li+].Cl[CH2-] VQEVKEKJZVEGPH-UHFFFAOYSA-N 0.000 description 1
- HTZGVHYSMVGNOV-UHFFFAOYSA-N lithium;dicyclohexylazanide Chemical compound [Li+].C1CCCCC1[N-]C1CCCCC1 HTZGVHYSMVGNOV-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013507 mapping Methods 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
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- DKTXXUNXVCHYDO-UHFFFAOYSA-N phenoxyborinic acid Chemical compound OBOC1=CC=CC=C1 DKTXXUNXVCHYDO-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WGLLSSPDPJPLOR-UHFFFAOYSA-N tetramethylethylene Natural products CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79614891A | 1991-11-22 | 1991-11-22 | |
| US796,148 | 1991-11-22 | ||
| US93619892A | 1992-08-26 | 1992-08-26 | |
| US936,198 | 1992-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1073946A true CN1073946A (zh) | 1993-07-07 |
Family
ID=27121696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN92113215A Pending CN1073946A (zh) | 1991-11-22 | 1992-11-23 | 制备脯氨酸硼酸酯的方法 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0641347A1 (pt) |
| JP (1) | JPH07501078A (pt) |
| CN (1) | CN1073946A (pt) |
| AU (1) | AU661362B2 (pt) |
| CA (1) | CA2123128A1 (pt) |
| CZ (1) | CZ124494A3 (pt) |
| FI (1) | FI942345A (pt) |
| HU (1) | HUT67937A (pt) |
| IL (1) | IL103817A0 (pt) |
| MX (1) | MX9206628A (pt) |
| NO (1) | NO941905L (pt) |
| NZ (1) | NZ245207A (pt) |
| PT (1) | PT101079A (pt) |
| SI (1) | SI9200332A (pt) |
| SK (1) | SK59294A3 (pt) |
| TW (1) | TW232697B (pt) |
| WO (1) | WO1993010127A1 (pt) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331835C (zh) * | 2005-10-18 | 2007-08-15 | 武汉大学 | 光活性β－羟基酮的制备方法 |
| CN103450241A (zh) * | 2008-06-17 | 2013-12-18 | 米伦纽姆医药公司 | 硼酸酯化合物及其医药组合物 |
| CN108047257A (zh) * | 2017-12-17 | 2018-05-18 | 沧州普瑞东方科技有限公司 | 一种手性n-boc-吡咯烷-2-硼酸的制备工艺 |
| CN110452258A (zh) * | 2019-09-03 | 2019-11-15 | 上海馨远医药科技有限公司 | 一种二肽缬氨酸硼脯氨酸盐的制备方法 |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6825169B1 (en) | 1991-10-22 | 2004-11-30 | Trustees Of Tufts College | Inhibitors of dipeptidyl-aminopeptidase type IV |
| US5965532A (en) * | 1996-06-28 | 1999-10-12 | Trustees Of Tufts College | Multivalent compounds for crosslinking receptors and uses thereof |
| US6040145A (en) | 1997-05-07 | 2000-03-21 | Tufts University | Potentiation of the immune response |
| US6100234A (en) | 1997-05-07 | 2000-08-08 | Tufts University | Treatment of HIV |
| DE69837393T2 (de) | 1997-09-29 | 2007-12-06 | Point Therapeutics, Inc., Boston | Stimulierung von hämatopoietischen zellen im vitro |
| KR20010052302A (ko) | 1998-05-04 | 2001-06-25 | 바바라 피. 월너 | 조혈 자극 |
| PT1084129E (pt) | 1998-06-05 | 2003-06-30 | Point Therapeutics Inc | Compostos de boroprolina ciclica |
| US6979697B1 (en) | 1998-08-21 | 2005-12-27 | Point Therapeutics, Inc. | Regulation of substrate activity |
| US6890904B1 (en) | 1999-05-25 | 2005-05-10 | Point Therapeutics, Inc. | Anti-tumor agents |
| EP1259246A2 (en) * | 2000-02-25 | 2002-11-27 | Novo Nordisk A/S | Use of dpp-iv inhibitors for the treatment of diabetes |
| WO2003063903A2 (en) * | 2002-02-01 | 2003-08-07 | Probiodrug Ag | Modulation of t lymphocytes using dp iv inhibitors |
| KR20070054762A (ko) * | 2003-11-12 | 2007-05-29 | 페노믹스 코포레이션 | 헤테로시클릭 보론산 화합물 |
| US7317109B2 (en) | 2003-11-12 | 2008-01-08 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| US7767828B2 (en) | 2003-11-12 | 2010-08-03 | Phenomix Corporation | Methyl and ethyl substituted pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| US7576121B2 (en) | 2003-11-12 | 2009-08-18 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| MXPA06005518A (es) | 2003-11-17 | 2006-08-17 | Novartis Ag | Uso de inhibidores de la dipeptidil peptidasa iv. |
| WO2005067976A2 (en) | 2004-01-20 | 2005-07-28 | Novartis Ag | Direct compression formulation and process |
| US7446211B2 (en) | 2004-04-27 | 2008-11-04 | Wyeth | Coupling process for generating reactive boron-containing derivatives of N-substituted pyrrole-2-carbonitriles to produce biaryls |
| DOP2006000008A (es) | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
| US7399869B2 (en) | 2005-05-19 | 2008-07-15 | Genentech, Inc. | Fibroblast activation protein inhibitor compounds and methods |
| US7825139B2 (en) | 2005-05-25 | 2010-11-02 | Forest Laboratories Holdings Limited (BM) | Compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| KR20080077024A (ko) | 2005-12-19 | 2008-08-20 | 트러스티즈 오브 터프츠 칼리지 | 소프트 단백질분해효소 억제자 및 이의 프로-소프트 폼 |
| KR101281962B1 (ko) | 2006-04-11 | 2013-07-08 | 아레나 파마슈티칼스, 인크. | 특정 개체에게서 골 질량을 증가시키는 데에 유용한 화합물을 확인하기 위해 ｇｐｒ119 수용체를 사용하는 방법 |
| PE20071221A1 (es) | 2006-04-11 | 2007-12-14 | Arena Pharm Inc | Agonistas del receptor gpr119 en metodos para aumentar la masa osea y para tratar la osteoporosis y otras afecciones caracterizadas por masa osea baja, y la terapia combinada relacionada a estos agonistas |
| EP2108960A1 (en) | 2008-04-07 | 2009-10-14 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditons modulated by PYY |
| AR077642A1 (es) | 2009-07-09 | 2011-09-14 | Arena Pharm Inc | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo |
| US20130023494A1 (en) | 2010-04-06 | 2013-01-24 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| EP2619198A1 (en) | 2010-09-22 | 2013-07-31 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2012135570A1 (en) | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| US20140066369A1 (en) | 2011-04-19 | 2014-03-06 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
| US20140038889A1 (en) | 2011-04-22 | 2014-02-06 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
| WO2012145604A1 (en) | 2011-04-22 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2012170702A1 (en) | 2011-06-08 | 2012-12-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2013055910A1 (en) | 2011-10-12 | 2013-04-18 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2014074668A1 (en) | 2012-11-08 | 2014-05-15 | Arena Pharmaceuticals, Inc. | Modulators of gpr119 and the treatment of disorders related thereto |
| US9523687B2 (en) | 2014-02-28 | 2016-12-20 | Institut Pasteur | Levels of CXCL 10/IP-10 forms and soluble CD26/DPPIV activity as early predictive biomarkers for HIV/SIV associated mucosal inflammation and progression towards AIDS |
| SG10202003693RA (en) | 2014-05-20 | 2020-05-28 | Millennium Pharm Inc | Boron-containing proteasome inhibitors for use after primary cancer therapy |
| SG10202103552XA (en) | 2015-03-09 | 2021-05-28 | Intekrin Therapeutics Inc | Methods for the treatment of nonalcoholic fatty liver disease and/or lipodystrophy |
| WO2018162722A1 (en) | 2017-03-09 | 2018-09-13 | Deutsches Institut Für Ernährungsforschung Potsdam-Rehbrücke | Dpp-4 inhibitors for use in treating bone fractures |
| AU2018249822A1 (en) | 2017-04-03 | 2019-10-31 | Coherus Biosciences Inc. | PPArgamma agonist for treatment of progressive supranuclear palsy |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4935493A (en) * | 1987-10-06 | 1990-06-19 | E. I. Du Pont De Nemours And Company | Protease inhibitors |
| ATE148130T1 (de) * | 1990-04-14 | 1997-02-15 | New England Medical Center Inc | Typ-iv-dipeptidyl-aminopeptidase-inhibitoren |
| GB9017694D0 (en) * | 1990-08-13 | 1990-09-26 | Sandoz Ltd | Improvements in or relating to organic chemistry |
-
1992
- 1992-11-18 MX MX9206628A patent/MX9206628A/es unknown
- 1992-11-19 JP JP5509442A patent/JPH07501078A/ja active Pending
- 1992-11-19 HU HU9401350A patent/HUT67937A/hu unknown
- 1992-11-19 WO PCT/US1992/009845 patent/WO1993010127A1/en not_active Application Discontinuation
- 1992-11-19 EP EP92925238A patent/EP0641347A1/en not_active Withdrawn
- 1992-11-19 CA CA002123128A patent/CA2123128A1/en not_active Abandoned
- 1992-11-19 AU AU31368/93A patent/AU661362B2/en not_active Expired - Fee Related
- 1992-11-19 PT PT101079A patent/PT101079A/pt not_active Application Discontinuation
- 1992-11-19 SK SK592-94A patent/SK59294A3/sk unknown
- 1992-11-19 SI SI19929200332A patent/SI9200332A/sl unknown
- 1992-11-19 CZ CZ941244A patent/CZ124494A3/cs unknown
- 1992-11-20 IL IL103817A patent/IL103817A0/xx unknown
- 1992-11-20 TW TW081109304A patent/TW232697B/zh active
- 1992-11-20 NZ NZ24520792A patent/NZ245207A/en unknown
- 1992-11-23 CN CN92113215A patent/CN1073946A/zh active Pending
-
1994
- 1994-05-20 FI FI942345A patent/FI942345A/fi not_active Application Discontinuation
- 1994-05-20 NO NO941905A patent/NO941905L/no unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331835C (zh) * | 2005-10-18 | 2007-08-15 | 武汉大学 | 光活性β－羟基酮的制备方法 |
| CN103450241A (zh) * | 2008-06-17 | 2013-12-18 | 米伦纽姆医药公司 | 硼酸酯化合物及其医药组合物 |
| CN103467565A (zh) * | 2008-06-17 | 2013-12-25 | 米伦纽姆医药公司 | 硼酸酯化合物及其医药组合物 |
| CN103497232A (zh) * | 2008-06-17 | 2014-01-08 | 米伦纽姆医药公司 | 硼酸酯化合物及其医药组合物 |
| CN108047257A (zh) * | 2017-12-17 | 2018-05-18 | 沧州普瑞东方科技有限公司 | 一种手性n-boc-吡咯烷-2-硼酸的制备工艺 |
| CN110452258A (zh) * | 2019-09-03 | 2019-11-15 | 上海馨远医药科技有限公司 | 一种二肽缬氨酸硼脯氨酸盐的制备方法 |
| CN110452258B (zh) * | 2019-09-03 | 2021-01-01 | 上海馨远医药科技有限公司 | 一种二肽缬氨酸硼脯氨酸盐的制备方法 |
| WO2021043187A1 (zh) * | 2019-09-03 | 2021-03-11 | 上海馨远医药科技有限公司 | 一种二肽缬氨酸硼脯氨酸盐的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU661362B2 (en) | 1995-07-20 |
| CA2123128A1 (en) | 1993-05-27 |
| NO941905L (no) | 1994-07-14 |
| IL103817A0 (en) | 1993-04-04 |
| FI942345A0 (fi) | 1994-05-20 |
| CZ124494A3 (en) | 1995-07-12 |
| SI9200332A (en) | 1993-06-30 |
| PT101079A (pt) | 1994-02-28 |
| NO941905D0 (no) | 1994-05-20 |
| AU3136893A (en) | 1993-06-15 |
| WO1993010127A1 (en) | 1993-05-27 |
| HU9401350D0 (en) | 1994-08-29 |
| HUT67937A (en) | 1995-05-29 |
| NZ245207A (en) | 1994-07-26 |
| FI942345A (fi) | 1994-05-20 |
| JPH07501078A (ja) | 1995-02-02 |
| MX9206628A (es) | 1993-05-01 |
| EP0641347A1 (en) | 1995-03-08 |
| TW232697B (pt) | 1994-10-21 |
| SK59294A3 (en) | 1995-02-08 |
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