HRP20200437T1 - Proces za pripremu enantiomerom obogaćenog 3-aminopiperidina - Google Patents
Proces za pripremu enantiomerom obogaćenog 3-aminopiperidina Download PDFInfo
- Publication number
- HRP20200437T1 HRP20200437T1 HRP20200437TT HRP20200437T HRP20200437T1 HR P20200437 T1 HRP20200437 T1 HR P20200437T1 HR P20200437T T HRP20200437T T HR P20200437TT HR P20200437 T HRP20200437 T HR P20200437T HR P20200437 T1 HRP20200437 T1 HR P20200437T1
- Authority
- HR
- Croatia
- Prior art keywords
- piperidine
- carboxylic acid
- acid
- respect
- azide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 10
- PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title claims 2
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- MBUAGLCTBJDIDV-UHFFFAOYSA-N piperidine-3-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1CCCNC1 MBUAGLCTBJDIDV-UHFFFAOYSA-N 0.000 claims 6
- ZKSMSCZAWFJIIQ-UHFFFAOYSA-N piperidine-3-carbohydrazide Chemical compound NNC(=O)C1CCCNC1 ZKSMSCZAWFJIIQ-UHFFFAOYSA-N 0.000 claims 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- 125000004494 ethyl ester group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 2
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (11)
1. Postupak za pripremu 3-aminopiperidina, koji postupak uključuje sljedeće korake:
a) dobivanje hidrazida piperidin-3-karboksilne kiseline, i
b) pretvaranje hidrazida piperidin-3-karboksilne kiseline u piperidin-3-karbonil azid reakcijom hidrazida piperidin-3-karboksilne kiseline s nitritom u prisutnosti kiseline, i
c) reakciju piperidin-3-karbonil-azida u prisutnosti vode i kiseline, pri čemu se piperidin-3-karbonil-azid pretvara u 3-aminopiperidin, gdje se koraci b) i c) provode bez izolacije piperidin-3-karbonil-azida.
2. Postupak prema zahtjevu 1, naznačen time što korak a) obuhvaća reakciju C1-C4-alkilestera ili benzilestera piperidin-3-karboksilne kiseline, posebno etilnog estera piperidin-3-karboksilne kiseline s hidrazinom.
3. Postupak prema zahtjevu 1 ili 2, naznačen time, da se hidrazid piperidin-3-karboksilne kiseline daje u ne-racemičnoj smjesi njihovih enantiomera, pri čemu je smjesa enantiomerno obogaćena s obzirom na jedan od njenih enantiomera.
4. Postupak prema zahtjevu 3, gdje C1-C4-alkilester piperidin-3-karboksilne kiseline, posebno etilni ester piperidin-3-karboksilne kiseline, koji je enantiomerno obogaćen s obzirom na jedan od njegovih enantiomera, reagira sa hidrazinom.
5. Postupak prema zahtjevu 4, naznačen time što korak a) obuhvaća podvrgavanje racemične C1-C4-alkilestere piperidin-3-karboksilne kiseline, posebno racemičnog etil estra piperidin-3-karboksilne kiseline, da bi se enantiomerno obogaćivalo s obzirom na R-enantiomer frakcijskom kristalizacijom kisele adicijske soli C1-C4-alkilestera piperidin-3-karboksilne kiseline s kiralnom kiselinom.
6. Postupak prema zahtjevu 5, naznačen time da je kiralna kiselina vinska kiselina ili mandelinska kiselina, posebno L-vinska kiselina ili D-mandelinska kiselina.
7. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da korak b) uključuje reakciju hidrazida piperidin-3-karboksilne kiseline s organskim nitritom, u prisutnosti kiseline.
8. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što je 3-aminopiperidin izoliran iz koraka c) kao njegov dihidroklorid ili dihidroklorid monohidrata.
9. Neracemični hidrazid piperidin-3-karboksilne kiseline, koji je enantiomerno obogaćen bilo s obzirom na njegov R-enantiomer ili s obzirom na njegov S-enantiomer, te njegove kiselinske adicijske soli i hidrati.
10. Piperidin-3-karbonil azid.
11. Neracemični piperidin-3-karbonil azid, koji je enantiomerno obogaćen bilo s obzirom na svoj R-enantiomer ili s obzirom na njegov S-enantiomer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13156030 | 2013-02-20 | ||
| EP14705501.6A EP2958894B8 (en) | 2013-02-20 | 2014-02-19 | Process for the preparation of enantiomerically enriched 3-aminopiperidine |
| PCT/EP2014/053176 WO2014128139A1 (en) | 2013-02-20 | 2014-02-19 | Process for the preparation of enantiomerically enriched 3-aminopiperidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20200437T1 true HRP20200437T1 (hr) | 2020-09-04 |
Family
ID=47748496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20200437TT HRP20200437T1 (hr) | 2013-02-20 | 2020-03-17 | Proces za pripremu enantiomerom obogaćenog 3-aminopiperidina |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US10464898B2 (hr) |
| EP (3) | EP3653607B1 (hr) |
| JP (2) | JP6370316B2 (hr) |
| KR (1) | KR102236806B1 (hr) |
| CN (1) | CN105102430A (hr) |
| DK (1) | DK2958894T3 (hr) |
| ES (1) | ES2777200T3 (hr) |
| HR (1) | HRP20200437T1 (hr) |
| HU (1) | HUE048567T2 (hr) |
| IL (1) | IL240214B (hr) |
| PL (1) | PL2958894T3 (hr) |
| PT (1) | PT2958894T (hr) |
| SI (1) | SI2958894T1 (hr) |
| WO (1) | WO2014128139A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2958894T3 (da) | 2013-02-20 | 2020-03-23 | Reuter Chemische Appbau E K | Fremgangsmåde til fremstilling af enantiomerisk beriget 3-aminopiperidin |
| CN108693272B (zh) * | 2018-06-04 | 2021-03-12 | 吉林百纯化学科技有限公司 | 一种hplc法分析及制备n-（对甲苯磺酰基）-l-丙氨酸及其对映异构体的方法 |
| CN109668987A (zh) * | 2019-02-27 | 2019-04-23 | 浙江华贝药业有限责任公司 | 一种3-氨基哌啶二盐酸盐对映异构体测定分析方法 |
| CN110078657A (zh) * | 2019-04-10 | 2019-08-02 | 湖州复华春生物医药科技有限公司 | 一种手性3-氨基哌啶及其衍生物的合成方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024974B (de) | 1956-10-17 | 1958-02-27 | Dr Alfred Dornow | Verfahren zur Herstellung von 2-Oxy-7-aza-benzimidazolen |
| US5334766A (en) * | 1991-04-29 | 1994-08-02 | Hoffmann-La Roche Inc. | Process for the resolution of racemic diphosphine oxides |
| US5220016A (en) | 1991-07-29 | 1993-06-15 | Board Of Regents, The University Of Texas System | Synthesis of navelbine analogs |
| JP3716376B2 (ja) * | 1995-10-26 | 2005-11-16 | 東レ・ファインケミカル株式会社 | 光学分割剤およびそれを用いた光学活性３−アミノピロリジン誘導体の製造法 |
| JP4157602B2 (ja) | 1996-03-10 | 2008-10-01 | ロイター・ヒェーミシェ・アパラーテバウ・コマンディート・ゲゼルシャフト | 分離方法 |
| SK13562001A3 (sk) | 1999-03-22 | 2002-08-06 | Ortho-Mcneil Pharmaceutical, Inc. | Spôsob prípravy [S-(R*,S*)]-beta-[[[1-[1-oxo-3-(4-piperidinyl)- propyl]-3-piperidinyl]karbonyl]amino]-3-pyridínpropánovej kyseliny a derivátov |
| AU781747B2 (en) * | 1999-10-08 | 2005-06-09 | Meiji Seika Kaisha Ltd. | 3-aminopiperidine derivatives as integrin alphavbeta3 antagonists |
| WO2001068604A2 (en) | 2000-03-14 | 2001-09-20 | Sepracor, Inc. | 3-substituted piperidines comprising urea functionality, and methods of use thereof |
| EP1146029A1 (en) | 2000-04-13 | 2001-10-17 | Nissan Chemical Industries Ltd. | Method for optical resolution of piperidine carboxylic acid derivative |
| AU2001297647A1 (en) | 2000-11-20 | 2002-09-12 | Eli Lilly And Company | Process for resolving racemic mixtures of piperidine derivatives |
| GB0126859D0 (en) | 2001-11-08 | 2002-01-02 | Kee Klamp Ltd | Counter-balance weight for a modular safety rail |
| WO2007075630A1 (en) | 2005-12-22 | 2007-07-05 | Dow Global Technologies Inc. | Method for producing 3-aminopiperidine diastereomer |
| ITMI20060179A1 (it) | 2006-02-02 | 2007-08-03 | Abiogen Pharma Spa | Procedimento per la risoluzione di miscele racemiche e complesso diastereoisomerico di un agente risolvente e di unantiomero di interesse |
| US20100029941A1 (en) * | 2006-03-28 | 2010-02-04 | Takeda Pharmaceutical Company Limited | Preparation of (r)-3-aminopiperidine dihydrochloride |
| US8338142B2 (en) | 2007-02-19 | 2012-12-25 | Kaneka Corporation | Method for producing optically active 3-aminopiperidine or salt thereof |
| WO2009107571A1 (ja) * | 2008-02-27 | 2009-09-03 | 住友化学株式会社 | アルキルピペリジン－３－イルカーバメートの光学分割方法およびその中間体 |
| CN101565397B (zh) * | 2009-04-07 | 2011-08-10 | 浙江医药股份有限公司新昌制药厂 | N-Boc-3-氨基哌啶及其光学异构体的合成方法 |
| JP2011012032A (ja) * | 2009-07-03 | 2011-01-20 | Yamakawa Yakuhin Kogyo Kk | 光学活性な３−アミノピペリジンの製造方法および製造の中間体 |
| JP5585822B2 (ja) | 2010-05-11 | 2014-09-10 | 東レ・ファインケミカル株式会社 | 光学活性ニペコチン酸誘導体の製造方法 |
| WO2011160037A2 (en) * | 2010-06-17 | 2011-12-22 | Dr. Reddy's Laboratories Ltd. | Process for the preparation of a single enantiomer of 3-aminopiperidine dihydrochloride |
| DK2958894T3 (da) | 2013-02-20 | 2020-03-23 | Reuter Chemische Appbau E K | Fremgangsmåde til fremstilling af enantiomerisk beriget 3-aminopiperidin |
-
2014
- 2014-02-19 DK DK14705501.6T patent/DK2958894T3/da active
- 2014-02-19 US US14/768,751 patent/US10464898B2/en active Active
- 2014-02-19 KR KR1020157025543A patent/KR102236806B1/ko active IP Right Grant
- 2014-02-19 ES ES14705501T patent/ES2777200T3/es active Active
- 2014-02-19 WO PCT/EP2014/053176 patent/WO2014128139A1/en active Application Filing
- 2014-02-19 EP EP19214799.9A patent/EP3653607B1/en active Active
- 2014-02-19 JP JP2015557468A patent/JP6370316B2/ja active Active
- 2014-02-19 SI SI201431527T patent/SI2958894T1/sl unknown
- 2014-02-19 CN CN201480009307.6A patent/CN105102430A/zh active Pending
- 2014-02-19 EP EP14705501.6A patent/EP2958894B8/en active Active
- 2014-02-19 PL PL14705501T patent/PL2958894T3/pl unknown
- 2014-02-19 HU HUE14705501A patent/HUE048567T2/hu unknown
- 2014-02-19 PT PT147055016T patent/PT2958894T/pt unknown
- 2014-02-19 EP EP23204103.8A patent/EP4289819A3/en active Pending
-
2015
- 2015-07-29 IL IL240214A patent/IL240214B/en active IP Right Grant
-
2018
- 2018-07-10 JP JP2018130513A patent/JP6580218B2/ja active Active
-
2019
- 2019-09-23 US US16/579,584 patent/US11472770B2/en active Active
-
2020
- 2020-03-17 HR HRP20200437TT patent/HRP20200437T1/hr unknown
-
2022
- 2022-09-09 US US17/941,959 patent/US11897843B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016508514A (ja) | 2016-03-22 |
| HUE048567T2 (hu) | 2020-07-28 |
| WO2014128139A1 (en) | 2014-08-28 |
| CN105102430A (zh) | 2015-11-25 |
| EP3653607B1 (en) | 2023-10-18 |
| IL240214A0 (en) | 2015-09-24 |
| JP2018168194A (ja) | 2018-11-01 |
| EP4289819A2 (en) | 2023-12-13 |
| IL240214B (en) | 2018-02-28 |
| EP3653607A2 (en) | 2020-05-20 |
| PL2958894T3 (pl) | 2020-06-29 |
| US11472770B2 (en) | 2022-10-18 |
| US20200087257A1 (en) | 2020-03-19 |
| PT2958894T (pt) | 2020-03-10 |
| JP6580218B2 (ja) | 2019-09-25 |
| EP3653607C0 (en) | 2023-10-18 |
| US11897843B2 (en) | 2024-02-13 |
| ES2777200T3 (es) | 2020-08-04 |
| EP2958894B1 (en) | 2019-12-18 |
| US20230008387A1 (en) | 2023-01-12 |
| KR20150123267A (ko) | 2015-11-03 |
| EP3653607A3 (en) | 2020-07-29 |
| ES2777200T8 (es) | 2020-09-29 |
| EP2958894B8 (en) | 2020-02-26 |
| US10464898B2 (en) | 2019-11-05 |
| EP4289819A3 (en) | 2024-01-10 |
| KR102236806B1 (ko) | 2021-04-06 |
| US20160251311A1 (en) | 2016-09-01 |
| JP6370316B2 (ja) | 2018-08-08 |
| EP2958894A1 (en) | 2015-12-30 |
| DK2958894T3 (da) | 2020-03-23 |
| SI2958894T1 (sl) | 2020-07-31 |
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