JP2013533231A5 - - Google Patents
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- Publication number
- JP2013533231A5 JP2013533231A5 JP2013513814A JP2013513814A JP2013533231A5 JP 2013533231 A5 JP2013533231 A5 JP 2013533231A5 JP 2013513814 A JP2013513814 A JP 2013513814A JP 2013513814 A JP2013513814 A JP 2013513814A JP 2013533231 A5 JP2013533231 A5 JP 2013533231A5
- Authority
- JP
- Japan
- Prior art keywords
- cooh
- substituted
- acid
- protected
- saturated
- 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 claims 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
- -1 N-protected 4-piperidinecarboxylic acid Chemical class 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 238000007348 radical reaction Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 150000001469 hydantoins Chemical class 0.000 claims 3
- HXLVCCRPDYIRRX-UHFFFAOYSA-N iodoamine Chemical compound IN HXLVCCRPDYIRRX-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- RDZHCKRAHUPIFK-UHFFFAOYSA-N 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(I)C(=O)N(I)C1=O RDZHCKRAHUPIFK-UHFFFAOYSA-N 0.000 claims 2
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 claims 2
- FBFMBRUWMOXOHQ-UHFFFAOYSA-N 3-iodo-4,4-dimethyl-1,3-oxazolidin-2-one Chemical compound CC1(C)COC(=O)N1I FBFMBRUWMOXOHQ-UHFFFAOYSA-N 0.000 claims 2
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000008282 halocarbons Chemical class 0.000 claims 2
- 229940091173 hydantoin Drugs 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 claims 1
- NERNEXMEYQFFHU-UHFFFAOYSA-N 1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCCCC1 NERNEXMEYQFFHU-UHFFFAOYSA-N 0.000 claims 1
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 claims 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 claims 1
- DSBMOVYUOIIPDK-UHFFFAOYSA-N 3-benzyl-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1CC1=CC=CC=C1 DSBMOVYUOIIPDK-UHFFFAOYSA-N 0.000 claims 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims 1
- JNGWGQUYLVSFND-UHFFFAOYSA-N 5-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C1(C)NC(=O)NC1=O JNGWGQUYLVSFND-UHFFFAOYSA-N 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35342710P | 2010-06-10 | 2010-06-10 | |
| US61/353,427 | 2010-06-10 | ||
| US201061427925P | 2010-12-29 | 2010-12-29 | |
| US61/427,925 | 2010-12-29 | ||
| PCT/IL2011/000458 WO2011154953A1 (en) | 2010-06-10 | 2011-06-09 | Process for the preparation of iodides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013533231A JP2013533231A (ja) | 2013-08-22 |
| JP2013533231A5 true JP2013533231A5 (https=) | 2014-07-24 |
| JP5603487B2 JP5603487B2 (ja) | 2014-10-08 |
Family
ID=44318441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013513814A Expired - Fee Related JP5603487B2 (ja) | 2010-06-10 | 2011-06-09 | ヨウ化物の調製のためのプロセス |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8822516B2 (https=) |
| JP (1) | JP5603487B2 (https=) |
| CL (1) | CL2012003489A1 (https=) |
| WO (1) | WO2011154953A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5603487B2 (ja) | 2010-06-10 | 2014-10-08 | テクニオン リサーチ アンド ディベラップメント ファウンデイション リミテッド | ヨウ化物の調製のためのプロセス |
| CA2807546C (en) | 2010-08-10 | 2022-08-23 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| IL229326A (en) | 2013-11-07 | 2015-11-30 | Technion Res & Dev Foundation | Process for making n-iodine-affluent |
| AU2015264418A1 (en) | 2014-05-19 | 2016-11-10 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| WO2016003929A1 (en) | 2014-07-01 | 2016-01-07 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10662205B2 (en) | 2014-11-18 | 2020-05-26 | Qpex Biopharma, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| JP6534154B2 (ja) * | 2015-09-02 | 2019-06-26 | 国立大学法人千葉大学 | Ｎ−アルキルイミド化合物の製造方法 |
| WO2017060906A1 (en) | 2015-10-07 | 2017-04-13 | Technion Research & Development Foundation Limited | Process for the preparation of organic halides |
| JP2018538239A (ja) * | 2015-10-07 | 2018-12-27 | テクニオン リサーチ アンド ディベロップメント ファウンデーション リミテッドＴｅｃｈｎｉｏｎ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｄｅｖｅｌｏｐｍｅｎｔ Ｆｏｕｎｄａｔｉｏｎ Ｌｔｄ． | 有機臭化物の調製方法 |
| MX389349B (es) | 2016-06-30 | 2025-03-20 | Qpex Biopharma Inc | Derivados de ácido borónico y usos terapéuticos de los mismos. |
| CN106748604B (zh) * | 2016-11-18 | 2020-06-05 | 湘潭大学 | 一种基于芳烃羧酸脱羧反应合成单碘代芳烃或二碘代芳烃的方法 |
| US11286270B2 (en) | 2017-10-11 | 2022-03-29 | Qpex Biopharma, Inc. | Boronic acid derivatives and synthesis thereof |
| WO2019199459A1 (en) * | 2018-04-12 | 2019-10-17 | Exxonmobil Chemical Patents Inc. | Preparation and use of biphenyl carboxylic acids, alcohols, and esters |
| EP3781576B1 (en) | 2018-04-20 | 2024-06-12 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN108929346A (zh) * | 2018-08-16 | 2018-12-04 | 陕西师范大学 | 一种高效立体选择性的构建α-和β-糖苷键的方法 |
| AU2021266715A1 (en) | 2020-05-05 | 2022-11-17 | Qpex Biopharma, Inc. | Boronic acid derivatives and synthesis, polymorphic forms, and therapeutic uses thereof |
| CN112723984B (zh) * | 2021-01-14 | 2022-03-01 | 上海交通大学 | 一种分离间溴碘苯和邻溴碘苯的方法 |
| JP7728864B2 (ja) * | 2021-05-28 | 2025-08-25 | 住友化学株式会社 | シクロアルキルブロミドの製造方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652682A (en) | 1968-02-28 | 1972-03-28 | Us Agriculture | Process for the preparation of alkyl perfluoroalkyl and aryl iodides |
| US3666820A (en) | 1968-02-28 | 1972-05-30 | Us Agriculture | Process for the preparation of alkyl, perfluoroalkyl and aryl iodides |
| US3531535A (en) | 1968-02-28 | 1970-09-29 | Us Agriculture | Process for the preparation of alkyl,perfluoroalkyl and aryl iodides |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| IL150982A (en) | 2002-07-30 | 2007-02-11 | Ori Lerman | Process for making Donafzil |
| US7138555B2 (en) | 2004-04-20 | 2006-11-21 | Xerox Corporation | Process for preparing iodoaromatic compounds and using the same |
| EP1928599B1 (en) | 2005-09-02 | 2012-10-03 | Japan Science and Technology Agency | Lewis acid catalyzed halogenation of activated carbon atoms |
| KR20190126460A (ko) | 2007-02-09 | 2019-11-11 | 메타베이시스 테라퓨틱스, 인크. | 글루카곤 수용체의 길항제 |
| WO2008143141A1 (ja) | 2007-05-18 | 2008-11-27 | Nippoh Chemicals Co., Ltd. | ハロゲン化芳香族化合物の製造方法 |
| GB0710865D0 (en) | 2007-06-06 | 2007-07-18 | Glaxo Group Ltd | Novel compounds |
| EP2110369A1 (en) | 2008-03-25 | 2009-10-21 | Semiconductor Energy Laboratory Co., Ltd. | Method of synthesizing 9-aryl-10-iodoanthracene derivative and light-emitting material |
| JP5295613B2 (ja) * | 2008-04-07 | 2013-09-18 | 日宝化学株式会社 | ヨウ素化芳香族化合物の製造方法 |
| AR076014A1 (es) | 2009-04-02 | 2011-05-11 | Sanofi Aventis | Derivados de 3- (1,4) oxazepan -4-pirimidona |
| JP5603487B2 (ja) | 2010-06-10 | 2014-10-08 | テクニオン リサーチ アンド ディベラップメント ファウンデイション リミテッド | ヨウ化物の調製のためのプロセス |
| EP2646026B1 (en) | 2010-12-03 | 2014-10-15 | Allergan, Inc. | Novel oxadiazole derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
| CA2819598A1 (en) | 2010-12-03 | 2012-06-07 | Allergan, Inc. | Novel phenyl oxadiazole derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
-
2011
- 2011-06-09 JP JP2013513814A patent/JP5603487B2/ja not_active Expired - Fee Related
- 2011-06-09 US US13/703,183 patent/US8822516B2/en active Active
- 2011-06-09 WO PCT/IL2011/000458 patent/WO2011154953A1/en not_active Ceased
-
2012
- 2012-12-10 CL CL2012003489A patent/CL2012003489A1/es unknown
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