BR112012006519A2 - síntese de t-butil éster de ácido (4-fluór-3-piperidin-4-il-benzin)-carbâmico e seus intermediários - Google Patents
síntese de t-butil éster de ácido (4-fluór-3-piperidin-4-il-benzin)-carbâmico e seus intermediáriosInfo
- Publication number
- BR112012006519A2 BR112012006519A2 BR112012006519A BR112012006519A BR112012006519A2 BR 112012006519 A2 BR112012006519 A2 BR 112012006519A2 BR 112012006519 A BR112012006519 A BR 112012006519A BR 112012006519 A BR112012006519 A BR 112012006519A BR 112012006519 A2 BR112012006519 A2 BR 112012006519A2
- Authority
- BR
- Brazil
- Prior art keywords
- compound
- fluoro
- butyl
- carbamic acid
- piperidin
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 title abstract 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- -1 t-butyl (4-fluoro-3-piperidin-4-yl-benzyl) -carbamic acid Chemical compound 0.000 abstract 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 abstract 1
- QUMSIFAQZIHRBC-UHFFFAOYSA-N B(O)O.C(C)(C)(C)OC(=O)NCC=1C=CC(=CC=1)F Chemical compound B(O)O.C(C)(C)(C)OC(=O)NCC=1C=CC(=CC=1)F QUMSIFAQZIHRBC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
síntese de t-butil éster de ácido (4-flúor-3-piperidin-4-il-benzil)-carbâmico e seus intermediários. a presente invenção refere-se a um método melhorado para a preparação de t-butil éster de ácido (4-flúor-3-piperidin-4-il-benzil)-carbâmico, composto de fórmula i. a invenção refere-se a um método de síntese para o composto de fórmula i em três etapas, compreendendo a formação de ácido 5-((t-butoxicarbonil)aminometil)-2-fluorobenzenoborônico (composto 11), reação de composto 11 sob condições de acoplamento suzuki para formar t-butil estér de ácido (4-flúor-2-piridin-4-il-benzil)-carbâmico e hidrogenação seletiva do produto acima mencionado em condições de hidrogenação, fornecendo o composto i. a invenção também se refere aos intermediários ácido 5-((t-butoxicarbonil)amino-metil)-2-fluorobenzeno borônico (composto 11), e t-butil éster de ácido (4-flúor-2-piridin-3-il-benzil)-carbâmico- (composto 13).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24532509P | 2009-09-24 | 2009-09-24 | |
| PCT/US2010/049737 WO2011037947A1 (en) | 2009-09-24 | 2010-09-22 | Synthesis of (4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester and intermediates thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR112012006519A2 true BR112012006519A2 (pt) | 2015-09-08 |
Family
ID=42984934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012006519A BR112012006519A2 (pt) | 2009-09-24 | 2010-09-22 | síntese de t-butil éster de ácido (4-fluór-3-piperidin-4-il-benzin)-carbâmico e seus intermediários |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8633321B2 (pt) |
| EP (1) | EP2483243B1 (pt) |
| JP (1) | JP2013505935A (pt) |
| KR (1) | KR20120083357A (pt) |
| CN (1) | CN102574792B (pt) |
| AU (1) | AU2010298425A1 (pt) |
| BR (1) | BR112012006519A2 (pt) |
| CA (1) | CA2774614C (pt) |
| IL (1) | IL218680A0 (pt) |
| MX (1) | MX2012003023A (pt) |
| MY (1) | MY155682A (pt) |
| RU (1) | RU2543483C2 (pt) |
| SG (1) | SG179201A1 (pt) |
| WO (1) | WO2011037947A1 (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011037947A1 (en) | 2009-09-24 | 2011-03-31 | Sanofi-Aventis U.S. Llc | Synthesis of (4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester and intermediates thereof |
| CA2812718C (en) * | 2010-09-27 | 2018-11-27 | E. I. Du Pont De Nemours And Company | Method for preparing 2-amino-n-(2,2,2-trifluoroethyl)acetamide |
| JP6578116B2 (ja) * | 2015-03-25 | 2019-09-18 | 公益財団法人相模中央化学研究所 | 一置換（フルオロアルキル）エチレン類及びその製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8912339D0 (en) * | 1989-05-30 | 1989-07-12 | Merck Patent Gmbh | Fluorinated biphenyl derivatives |
| US6248103B1 (en) | 1994-04-05 | 2001-06-19 | The Regents Of The University Of California | Apparatus and method for dynamic cooling of biological tissues for thermal mediated surgery using long laser pulses |
| DE10101022A1 (de) * | 2001-01-11 | 2002-07-18 | Clariant Internat Ltd Muttenz | Fluorierte Aromaten und ihre Verwendung in Flüssigkristallmischungen |
| JP2005111003A (ja) * | 2003-10-08 | 2005-04-28 | Kita Denshi Corp | 遊技場システム、現金管理装置及び搬送異常検出方法 |
| EP1571150A1 (en) * | 2004-03-02 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Process for the preparation of tryptase inhibitors |
| DOP2005000039A (es) * | 2004-03-26 | 2005-10-31 | Aventis Pharma Inc | Hidrocloruro de [4-(5-aminometil-2-fluoro-fenil)- piperidin-1-il]-(4-bomo-3-metil-5-propoxi-tiofen-2-il)-metanona como un inhibidor de la triptasa de mastocitos |
| MXPA06012595A (es) * | 2004-04-29 | 2007-05-09 | Abbott Lab | Analogos de amino-tetrazoles y metodos de uso. |
| WO2011037947A1 (en) | 2009-09-24 | 2011-03-31 | Sanofi-Aventis U.S. Llc | Synthesis of (4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester and intermediates thereof |
-
2010
- 2010-09-22 WO PCT/US2010/049737 patent/WO2011037947A1/en active Application Filing
- 2010-09-22 AU AU2010298425A patent/AU2010298425A1/en not_active Abandoned
- 2010-09-22 KR KR1020127007644A patent/KR20120083357A/ko not_active Application Discontinuation
- 2010-09-22 EP EP10757923.7A patent/EP2483243B1/en active Active
- 2010-09-22 SG SG2012018958A patent/SG179201A1/en unknown
- 2010-09-22 CA CA2774614A patent/CA2774614C/en not_active Expired - Fee Related
- 2010-09-22 BR BR112012006519A patent/BR112012006519A2/pt not_active IP Right Cessation
- 2010-09-22 CN CN201080042702.6A patent/CN102574792B/zh active Active
- 2010-09-22 MY MYPI2012001233A patent/MY155682A/en unknown
- 2010-09-22 RU RU2012116346/04A patent/RU2543483C2/ru not_active IP Right Cessation
- 2010-09-22 MX MX2012003023A patent/MX2012003023A/es active IP Right Grant
- 2010-09-22 JP JP2012530984A patent/JP2013505935A/ja not_active Ceased
-
2012
- 2012-03-15 IL IL218680A patent/IL218680A0/en unknown
- 2012-03-22 US US13/426,721 patent/US8633321B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2483243B1 (en) | 2015-03-18 |
| SG179201A1 (en) | 2012-05-30 |
| MX2012003023A (es) | 2012-04-10 |
| CN102574792B (zh) | 2014-07-09 |
| US20120184745A1 (en) | 2012-07-19 |
| RU2012116346A (ru) | 2013-10-27 |
| IL218680A0 (en) | 2012-05-31 |
| CA2774614C (en) | 2015-03-10 |
| AU2010298425A1 (en) | 2012-04-19 |
| WO2011037947A1 (en) | 2011-03-31 |
| KR20120083357A (ko) | 2012-07-25 |
| RU2543483C2 (ru) | 2015-03-10 |
| EP2483243A1 (en) | 2012-08-08 |
| JP2013505935A (ja) | 2013-02-21 |
| CN102574792A (zh) | 2012-07-11 |
| US8633321B2 (en) | 2014-01-21 |
| CA2774614A1 (en) | 2011-03-31 |
| MY155682A (en) | 2015-11-13 |
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Legal Events
| Date | Code | Title | Description |
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| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 6A ANUIDADE. |
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| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: EM VIRTUDE DO ARQUIVAMENTO PUBLICADO NA RPI 2384 DE 13-09-2016 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDO O ARQUIVAMENTO DO PEDIDO DE PATENTE, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |