AR066748A1 - Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina utiles como intemediarios para florfenicol - Google Patents
Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina utiles como intemediarios para florfenicolInfo
- Publication number
- AR066748A1 AR066748A1 ARP080102241A ARP080102241A AR066748A1 AR 066748 A1 AR066748 A1 AR 066748A1 AR P080102241 A ARP080102241 A AR P080102241A AR P080102241 A ARP080102241 A AR P080102241A AR 066748 A1 AR066748 A1 AR 066748A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- oxazoline
- alkyl
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title abstract 2
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 title 1
- CIAZEFCFQFQJLB-NXEZZACHSA-N (1r,2r)-2-amino-1-(4-methylsulfonylphenyl)propane-1,3-diol Chemical class CS(=O)(=O)C1=CC=C([C@@H](O)[C@H](N)CO)C=C1 CIAZEFCFQFQJLB-NXEZZACHSA-N 0.000 title 1
- 229960003760 florfenicol Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 12
- -1 methylthio, methylsulfoxy, methylsulfonyl Chemical group 0.000 abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004445 cyclohaloalkyl Chemical group 0.000 abstract 1
- HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 abstract 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004982 dihaloalkyl group Chemical group 0.000 abstract 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical group [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Reivindicacion 1: Un proceso para la preparacion de un compuesto de aminodiol protegido con oxazolina, de la Formula (1), o una de sus sales de adicion de ácido: donde: R2 es hidrogeno, metiltio, metilsulfoxi, metilsulfonilo, fluormetiltio, fluormetilsulfoxi, fluormetilsulfonilo, nitro, fluor, bromo, cloro, acetilo, bencilo, fenilo, fenilo sustituido con halo, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-8, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, aralquilo C1-6, aralquenilo C2-6, o grupo heterocíclico C2-6; y R4 es hidrogeno, alquilo C1-6, haloalquilo C1-6, dihaloalquilo C1-6, trihaloalquilo C1-6, CH2Cl, CHCl2, CCl3, CH2Br, CHBr2, CBr3, CH2F, CHF2, CF3, cicloalquilo C3-8, ciclohaloalquilo C3-8, ciclodihaloalquilo C3-8, ciclotrihaloalquilo C3-8, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, aralquilo C1-6, aralquenilo C2-6, heterociclico C2-6, bencilo, o fenilo alquilo donde el fenilo o fenilo alquilo puede estar sustituido con uno o dos halogenos, alquilo C1-6 o alcoxi C1-6; donde el proceso comprende las etapas de: a) la reaccion de un compuesto de la Formula (2) o una de sus sales de adicion de ácido: (2) donde: R2 es corno se define con anterioridad; y R3 es hidrogeno, alquilo C1-6, cicloalquilo C3-8, bencilo, fenilo o alquilfenilo C1-6; con la condicion de que si el compuesto de la Formula (2) y es la sal de adicion de ácido, entonces la sal de adicion de ácido es la sal de HCI, HNO3, H2SO4, H3PO4 o la sal de ácido acético; con un reactivo promotor de amida, en un solvente formador de amida, con un compuesto promotor de amida, para formar un compuesto de éster amida de la Formula (3): donde R2, R3 y R4 se definen conforme a lo descripto con anterioridad: b) la reaccion del compuesto de la Formula (3) con un reactivo promotor de oxazolina, en un solvente formador de oxazolina, en presencia de un compuesto promotor de oxazolina, para formar un compuesto de éster oxazolina de la Formula (4): donde R2, R3 y R4 se definen segun lo descripto con anterioridad, y se presenta una estereoquímica relativa invertida en el carbono bencílico asimétrico, en comparacion con aquella del compuesto de la Formula (3); c) la reaccion del compuesto de la Formula (4) con una base de inversion de centro quiral en un solvente de inversion de centro quiral, para formar un compuesto de la Formula (5): donde R2, R3 y R4 se definen segun lo descripto con anterioridad, y donde se presenta una estereoquímica relativa invertida en el carbono de alfa-carbonilo asimétrico, en comparacion con aquella del compuesto de la Formula (4); y d) la reaccion del compuesto de la Formula (5) con un agente reductor, en un solvente promotor de la reduccion, para formar un compuesto de la Formula (6): donde R2 y R4 se definen segun lo descripto con anterioridad.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94078607P | 2007-05-30 | 2007-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR066748A1 true AR066748A1 (es) | 2009-09-09 |
Family
ID=39705084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080102241A AR066748A1 (es) | 2007-05-30 | 2008-05-28 | Un proceso para la preparacion de compuestos de aminodiol protegidos con oxazolina utiles como intemediarios para florfenicol |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20080319200A1 (es) |
| EP (1) | EP2155702A1 (es) |
| JP (1) | JP2010529016A (es) |
| KR (1) | KR20100022999A (es) |
| CN (1) | CN101784534A (es) |
| AR (1) | AR066748A1 (es) |
| AU (1) | AU2008260595A1 (es) |
| BR (1) | BRPI0812297A2 (es) |
| CA (1) | CA2688432A1 (es) |
| CL (1) | CL2008001562A1 (es) |
| MX (1) | MX2009013016A (es) |
| PE (1) | PE20090758A1 (es) |
| RU (1) | RU2009148864A (es) |
| TW (1) | TW200904783A (es) |
| WO (1) | WO2008150406A1 (es) |
| ZA (1) | ZA200908404B (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY146351A (en) | 2003-05-29 | 2012-08-15 | Schering Plough Ltd | Compositions for treating infection in cattle and swine |
| CN101600686A (zh) * | 2006-12-13 | 2009-12-09 | 先灵-普劳有限公司 | 氯霉素、甲砜霉素及其类似物的水溶性前药 |
| JP2011529895A (ja) * | 2008-07-30 | 2011-12-15 | インターベツト・インターナシヨナル・ベー・ベー | フロルフェニコール中間体として有用なオキサゾリン保護アミノジオール化合物を調製する方法 |
| PH12012500734A1 (en) | 2009-10-16 | 2012-11-26 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| US9216979B2 (en) | 2009-10-16 | 2015-12-22 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| JP2014513116A (ja) | 2011-05-02 | 2014-05-29 | ゾエティス・エルエルシー | 抗菌剤として有用な新規セファロスポリン |
| CN103254103A (zh) * | 2013-06-05 | 2013-08-21 | 南通金利油脂工业有限公司 | 氟化剂在制备氟苯尼考工艺中的应用 |
| EP3039025A4 (en) | 2013-09-09 | 2017-05-31 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| AU2014315045A1 (en) | 2013-09-09 | 2016-03-24 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| CN103980166B (zh) * | 2014-04-17 | 2016-06-22 | 天津大学 | 一种氟苯尼考的新晶型及其制备方法 |
| KR20180015114A (ko) | 2015-03-11 | 2018-02-12 | 멜린타 테라퓨틱스, 인크. | 항미생물 화합물 및 이의 제조 및 사용 방법 |
| CN105218474B (zh) * | 2015-10-22 | 2017-12-05 | 山东国邦药业股份有限公司 | (4r,5r)‑2‑二氯甲基‑4,5‑二氢‑5‑(4‑甲砜基苯基)‑4‑恶唑甲醇的合成方法 |
| EP3452479A1 (en) | 2016-05-06 | 2019-03-13 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| CN106187837B (zh) * | 2016-07-05 | 2020-03-20 | 和鼎（南京）医药技术有限公司 | 一种氟苯尼考中间体、及其制备方法和氟苯尼考的制备方法 |
| CN106631872A (zh) * | 2016-12-13 | 2017-05-10 | 浙江普洛家园药业有限公司 | 一种氟苯尼考类似物中间体的合成方法 |
| CN109678811B (zh) * | 2019-01-25 | 2020-12-29 | 湖北中牧安达药业有限公司 | 一种氟苯尼考中间体环合物的不对称制备方法 |
| CN110330463B (zh) * | 2019-08-02 | 2021-05-14 | 山东国邦药业有限公司 | 一种氟苯尼考中间体的制备方法 |
| CN111285789A (zh) * | 2020-03-16 | 2020-06-16 | 和鼎（南京）医药技术有限公司 | 制备氟苯尼考中间体的方法及由该方法得到的化合物 |
| CN111423391A (zh) * | 2020-03-18 | 2020-07-17 | 浙江康牧药业有限公司 | 一种氟苯尼考中间体的制备方法 |
| CN118084747B (zh) * | 2024-04-28 | 2024-07-09 | 山东国邦药业有限公司 | 一种氟苯尼考的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957484C (de) * | 1950-03-24 | 1957-02-07 | Parke Davis & Co | Verfahren zur Herstellung von neuen Oxazolinabkoemmlingen |
| DE830956C (de) * | 1950-05-23 | 1952-02-07 | Parke Davis & Co | Verfahren zur Herstellung von Aminodiolen |
| US2768972A (en) * | 1951-03-13 | 1956-10-30 | Centre Nat Rech Scient | Preparation of n-acyl-beta aryl-serinols |
| US2816915A (en) * | 1953-11-20 | 1957-12-17 | Du Pont | Separation of phenyl-serines |
| US5663361A (en) * | 1996-08-19 | 1997-09-02 | Schering Corporation | Process for preparing intermediates to florfenicol |
| CN1173933C (zh) * | 2001-06-01 | 2004-11-03 | 中国科学院上海有机化学研究所 | 一种从l型取代苯丝氨酸酯制备d－（－）－苏式1－r－取代苯基－2－二氯乙酰氨基－3－氟－1－丙醇的方法 |
| CN1155553C (zh) * | 2001-12-07 | 2004-06-30 | 中国科学院上海有机化学研究所 | 2－氟－α－甲基－[1，1’－二苯基]－4－乙酸的对映体的制备方法 |
| CN1649829A (zh) * | 2002-03-08 | 2005-08-03 | 先灵-普劳有限公司 | 新型氟苯尼考类抗生素 |
-
2008
- 2008-05-28 CA CA002688432A patent/CA2688432A1/en not_active Abandoned
- 2008-05-28 AU AU2008260595A patent/AU2008260595A1/en not_active Abandoned
- 2008-05-28 PE PE2008000910A patent/PE20090758A1/es not_active Application Discontinuation
- 2008-05-28 JP JP2010510320A patent/JP2010529016A/ja not_active Withdrawn
- 2008-05-28 KR KR1020097026768A patent/KR20100022999A/ko not_active Withdrawn
- 2008-05-28 MX MX2009013016A patent/MX2009013016A/es not_active Application Discontinuation
- 2008-05-28 US US12/128,146 patent/US20080319200A1/en not_active Abandoned
- 2008-05-28 RU RU2009148864/04A patent/RU2009148864A/ru unknown
- 2008-05-28 WO PCT/US2008/006742 patent/WO2008150406A1/en not_active Ceased
- 2008-05-28 CN CN200880101386A patent/CN101784534A/zh active Pending
- 2008-05-28 AR ARP080102241A patent/AR066748A1/es not_active Application Discontinuation
- 2008-05-28 BR BRPI0812297-0A2A patent/BRPI0812297A2/pt not_active Application Discontinuation
- 2008-05-28 EP EP08767907A patent/EP2155702A1/en not_active Withdrawn
- 2008-05-29 TW TW097119968A patent/TW200904783A/zh unknown
- 2008-05-29 CL CL2008001562A patent/CL2008001562A1/es unknown
-
2009
- 2009-11-26 ZA ZA200908404A patent/ZA200908404B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2155702A1 (en) | 2010-02-24 |
| JP2010529016A (ja) | 2010-08-26 |
| AU2008260595A1 (en) | 2008-12-11 |
| CN101784534A (zh) | 2010-07-21 |
| KR20100022999A (ko) | 2010-03-03 |
| RU2009148864A (ru) | 2011-07-10 |
| WO2008150406A1 (en) | 2008-12-11 |
| MX2009013016A (es) | 2010-02-17 |
| PE20090758A1 (es) | 2009-06-24 |
| AU2008260595A2 (en) | 2010-01-07 |
| TW200904783A (en) | 2009-02-01 |
| CL2008001562A1 (es) | 2008-12-05 |
| CA2688432A1 (en) | 2008-12-11 |
| ZA200908404B (en) | 2010-08-25 |
| US20080319200A1 (en) | 2008-12-25 |
| BRPI0812297A2 (pt) | 2014-11-25 |
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