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
- Prior art date
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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 description 11
- -1 proline boronic acid ester Chemical class 0.000 claims abstract description 59
- 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
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 150000001413 amino acids Chemical class 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004185 ester group Chemical group 0.000 claims abstract description 8
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 167
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 claims description 121
- 239000004327 boric acid Substances 0.000 claims description 96
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 70
- 229930006728 pinane Natural products 0.000 claims description 62
- 239000000243 solution Substances 0.000 claims description 56
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
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- 125000000217 alkyl group Chemical group 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- 150000002430 hydrocarbons Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000006138 lithiation reaction Methods 0.000 claims description 11
- 150000003233 pyrroles Chemical class 0.000 claims description 11
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
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- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical group [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 10
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 8
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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- 125000005620 boronic acid group Chemical group 0.000 abstract 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
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- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
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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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US796,148 | 1985-11-08 | ||
| US79614891A | 1991-11-22 | 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)
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|---|---|
| EP (1) | EP0641347A1 (enExample) |
| JP (1) | JPH07501078A (enExample) |
| CN (1) | CN1073946A (enExample) |
| AU (1) | AU661362B2 (enExample) |
| CA (1) | CA2123128A1 (enExample) |
| CZ (1) | CZ124494A3 (enExample) |
| FI (1) | FI942345A0 (enExample) |
| HU (1) | HUT67937A (enExample) |
| IL (1) | IL103817A0 (enExample) |
| MX (1) | MX9206628A (enExample) |
| NO (1) | NO941905L (enExample) |
| NZ (1) | NZ245207A (enExample) |
| PT (1) | PT101079A (enExample) |
| SI (1) | SI9200332A (enExample) |
| SK (1) | SK59294A3 (enExample) |
| TW (1) | TW232697B (enExample) |
| WO (1) | WO1993010127A1 (enExample) |
Cited By (5)
| 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 |
| CN111741939A (zh) * | 2018-02-20 | 2020-10-02 | 大塚制药株式会社 | 制备4-二羟硼基苯丙氨酸的方法 |
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| 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 |
| US6100234A (en) | 1997-05-07 | 2000-08-08 | Tufts University | Treatment of HIV |
| US6040145A (en) | 1997-05-07 | 2000-03-21 | Tufts University | Potentiation of the immune response |
| IL135068A (en) | 1997-09-29 | 2004-03-28 | Point Therapeutics Inc | Stimulation of hematopoietic cells in vitro |
| KR20010052302A (ko) | 1998-05-04 | 2001-06-25 | 바바라 피. 월너 | 조혈 자극 |
| WO1999062914A1 (en) * | 1998-06-05 | 1999-12-09 | Point Therapeutics, Inc. | Cyclic boroproline compounds |
| 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 |
| AU2001233622A1 (en) * | 2000-02-25 | 2001-09-03 | Novo-Nordisk A/S | Inhibition of beta cell degeneration |
| WO2003063903A2 (en) * | 2002-02-01 | 2003-08-07 | Probiodrug Ag | Modulation of t lymphocytes using dp iv inhibitors |
| 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 |
| DK1689757T3 (en) * | 2003-11-12 | 2014-12-08 | Sino Med Internat Alliance Inc | HETEROCYCLIC DRY ACID COMPOUNDS |
| US7576121B2 (en) | 2003-11-12 | 2009-08-18 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| US7317109B2 (en) | 2003-11-12 | 2008-01-08 | Phenomix Corporation | Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| KR20120008093A (ko) | 2003-11-17 | 2012-01-25 | 노파르티스 아게 | 디펩티딜 펩티다제 ⅳ 억제제의 용도 |
| ES2684325T5 (es) | 2004-01-20 | 2024-06-10 | Novartis Ag | Formulación y proceso de compresión directa |
| AR049631A1 (es) | 2004-04-27 | 2006-08-23 | Wyeth Corp | Proceso de acoplamiento para la generacion de derivados reactivos de pirrol -2- carbonitrilo n- sustituidos con contenido de boro para producir biarilos |
| 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 |
| CA2606785A1 (en) | 2005-05-19 | 2006-11-23 | 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 |
| CA2633803A1 (en) * | 2005-12-19 | 2007-09-07 | Trustees Of Tufts College | Soft protease inhibitors and pro-soft forms thereof |
| DE602007010420D1 (de) | 2006-04-11 | 2010-12-23 | Arena Pharm Inc | Verfahren zur verwendung des gpr119-rezeptors zur identifizierung von verbindungen zur erhöhung der knochenmasse bei einer person |
| 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 |
| EP2146210A1 (en) | 2008-04-07 | 2010-01-20 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditions 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 |
| WO2011127051A1 (en) | 2010-04-06 | 2011-10-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
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| WO2012135570A1 (en) | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2012145361A1 (en) | 2011-04-19 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
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| US20140051714A1 (en) | 2011-04-22 | 2014-02-20 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
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| 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 |
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| CA2979033A1 (en) | 2015-03-09 | 2016-09-15 | Intekrin Therapeutics, Inc. | Methods for the treatment of nonalcoholic fatty liver disease and/or lipodystrophy |
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| CN110996951A (zh) | 2017-04-03 | 2020-04-10 | 科赫罗斯生物科学股份有限公司 | 治疗进行性核上性麻痹的PPARγ激动剂 |
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 |
| EP0528858B1 (en) * | 1990-04-14 | 1997-01-22 | New England Medical Center Hospitals, Inc. | Inhibitors of dipeptidyl-aminopeptidase type iv |
| 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 HU HU9401350A patent/HUT67937A/hu unknown
- 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 JP JP5509442A patent/JPH07501078A/ja active Pending
- 1992-11-19 WO PCT/US1992/009845 patent/WO1993010127A1/en not_active Ceased
- 1992-11-19 CZ CZ941244A patent/CZ124494A3/cs unknown
- 1992-11-19 SI SI19929200332A patent/SI9200332A/sl unknown
- 1992-11-19 SK SK592-94A patent/SK59294A3/sk unknown
- 1992-11-19 EP EP92925238A patent/EP0641347A1/en not_active Withdrawn
- 1992-11-19 CA CA002123128A patent/CA2123128A1/en not_active Abandoned
- 1992-11-20 NZ NZ24520792A patent/NZ245207A/en unknown
- 1992-11-20 IL IL103817A patent/IL103817A0/xx unknown
- 1992-11-20 TW TW081109304A patent/TW232697B/zh active
- 1992-11-23 CN CN92113215A patent/CN1073946A/zh active Pending
-
1994
- 1994-05-20 NO NO941905A patent/NO941905L/no unknown
- 1994-05-20 FI FI942345A patent/FI942345A0/fi not_active Application Discontinuation
Cited By (9)
| 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 |
| CN111741939A (zh) * | 2018-02-20 | 2020-10-02 | 大塚制药株式会社 | 制备4-二羟硼基苯丙氨酸的方法 |
| 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 |
|---|---|
| FI942345A7 (fi) | 1994-05-20 |
| JPH07501078A (ja) | 1995-02-02 |
| AU3136893A (en) | 1993-06-15 |
| PT101079A (pt) | 1994-02-28 |
| SI9200332A (en) | 1993-06-30 |
| EP0641347A1 (en) | 1995-03-08 |
| IL103817A0 (en) | 1993-04-04 |
| AU661362B2 (en) | 1995-07-20 |
| TW232697B (enExample) | 1994-10-21 |
| CA2123128A1 (en) | 1993-05-27 |
| NO941905D0 (no) | 1994-05-20 |
| SK59294A3 (en) | 1995-02-08 |
| FI942345A0 (fi) | 1994-05-20 |
| MX9206628A (es) | 1993-05-01 |
| HUT67937A (en) | 1995-05-29 |
| WO1993010127A1 (en) | 1993-05-27 |
| CZ124494A3 (en) | 1995-07-12 |
| NZ245207A (en) | 1994-07-26 |
| HU9401350D0 (en) | 1994-08-29 |
| NO941905L (no) | 1994-07-14 |
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