AR015571A1 - Procedimiento para la elaboracion de compuestos derivados de alfa-bromo-lactama y el uso de dichos compuestos para la preparacion de cefalosporinas - Google Patents
Procedimiento para la elaboracion de compuestos derivados de alfa-bromo-lactama y el uso de dichos compuestos para la preparacion de cefalosporinasInfo
- Publication number
- AR015571A1 AR015571A1 ARP980100999A ARP980100999A AR015571A1 AR 015571 A1 AR015571 A1 AR 015571A1 AR P980100999 A ARP980100999 A AR P980100999A AR P980100999 A ARP980100999 A AR P980100999A AR 015571 A1 AR015571 A1 AR 015571A1
- Authority
- AR
- Argentina
- Prior art keywords
- lower alkyl
- compounds
- aryl
- preparation
- heterocyclyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Procedimiento para la elaboracion de compuestos derivados de alfa-bromo-lactama de la formula (1) en donde R es hidrogeno, alquilo inferior, alcoxiloinferior, cicloalquilo, cicloalquenilo, cicloalquilo-alquilo inferior, alquenilo inferior, alquiniloinferior, arilo, aril-alquilo inferior, heterociclilo oheterociclil-alquilo inferior;estando el alquilo inferior, cicloalquilo, alquenilo inferior, cicloalquenilo, alquinilo inferior, aril-alquilo inferior, arilo ylas fracciones de heterocicliloinsu stituidas o sustituidas por al menos un grupo elegido entre carboxilo, amino, amido, carbamoilo, nitro, ciano, alquiloinferior, alcoxilo inferior, hidroxilo, halogeno, cuyo procedimiento se caracteriza por: a) hacer reaccionar cloruro de ácido4-clor o-butírico conN-bromosuccinimida en un disolvente inerte adicionando primero cloruro de tionilo, seguido inmediatamente de una cantidad catalítica de ácido bromhídrico paraformar un compuesto de la formula (2); y b) hacer reaccionar elcompuesto (2) con una amina de la formula R-NH2, en donde R es como se ha definido antes, en unmedio no acuoso en presencia de hidroxido sodico o potásico y un catalizador de transferencia de fase; y el uso de estos compuestos para la preparaciondecefalosporinas.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97103964 | 1997-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR015571A1 true AR015571A1 (es) | 2001-05-16 |
Family
ID=8226572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP980100999A AR015571A1 (es) | 1997-03-10 | 1998-03-06 | Procedimiento para la elaboracion de compuestos derivados de alfa-bromo-lactama y el uso de dichos compuestos para la preparacion de cefalosporinas |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6114541A (es) |
| EP (1) | EP0864564B1 (es) |
| JP (1) | JP2938427B2 (es) |
| KR (1) | KR100280561B1 (es) |
| CN (1) | CN1193014A (es) |
| AR (1) | AR015571A1 (es) |
| AT (1) | ATE219056T1 (es) |
| AU (1) | AU728147B2 (es) |
| BR (1) | BR9800844A (es) |
| CA (1) | CA2231631A1 (es) |
| CY (1) | CY2392B1 (es) |
| DE (1) | DE69805887T2 (es) |
| DK (1) | DK0864564T3 (es) |
| ES (1) | ES2176841T3 (es) |
| TR (1) | TR199800403A3 (es) |
| ZA (1) | ZA981885B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9901712D0 (sv) * | 1999-05-11 | 1999-05-11 | Astra Ab | New process |
| US7741327B2 (en) | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| TW201615643A (zh) | 2014-06-02 | 2016-05-01 | 伊史帝夫博士實驗室股份有限公司 | 具有多重模式抗疼痛活性之１－氧雜－４，９－二氮雜螺十一烷化合物之烷基與芳基衍生物 |
| TWI685497B (zh) | 2014-06-02 | 2020-02-21 | 西班牙商伊史帝夫製藥公司 | 具有多重模式抗疼痛活性的１-氧雜-４,９-二氮雜螺十一烷化合物之烷基衍生物 |
| TW201808921A (zh) | 2015-10-23 | 2018-03-16 | 艾斯提夫博士實驗股份有限公司 | 具有抗疼痛活性之氧雜－氮雜螺環化合物 |
| EP3365346B1 (en) | 2015-10-23 | 2019-12-04 | Esteve Pharmaceuticals, S.A. | Oxa-diazaspiro compounds having activity against pain |
| CN108137569B (zh) | 2015-10-23 | 2022-03-15 | 埃斯蒂文制药股份有限公司 | 具有抗疼痛活性的取代的吗啉衍生物 |
| AR106697A1 (es) | 2015-11-16 | 2018-02-07 | Esteve Labor Dr | Compuestos oxadiazoespíricos para el tratamiento del abuso y la adicción a las drogas |
| CN107129454A (zh) * | 2017-05-04 | 2017-09-05 | 唐山威格化学工业有限公司 | N‑辛基吡咯烷酮的合成方法 |
| US11236110B2 (en) | 2017-10-17 | 2022-02-01 | Esteve Pharmaceuticals, S.A. | Salts of (R)-9-(2,5-difluorophenethyl)-4-ethyl-2-methyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0620225B1 (en) * | 1993-04-16 | 2002-11-13 | Basilea Pharmaceutica AG | Cephalosporin derivatives |
| US5523400A (en) * | 1993-04-16 | 1996-06-04 | Hoffmann-La Roche Inc. | Cephalosporin antibiotics |
| US5811419A (en) * | 1996-01-16 | 1998-09-22 | Hoffmann-La Roche Inc. | Isooxacephem-derivatives |
-
1998
- 1998-02-06 US US09/019,941 patent/US6114541A/en not_active Expired - Lifetime
- 1998-03-02 ES ES98103570T patent/ES2176841T3/es not_active Expired - Lifetime
- 1998-03-02 EP EP98103570A patent/EP0864564B1/en not_active Expired - Lifetime
- 1998-03-02 DK DK98103570T patent/DK0864564T3/da active
- 1998-03-02 AT AT98103570T patent/ATE219056T1/de active
- 1998-03-02 DE DE69805887T patent/DE69805887T2/de not_active Expired - Lifetime
- 1998-03-05 ZA ZA981885A patent/ZA981885B/xx unknown
- 1998-03-05 AU AU57374/98A patent/AU728147B2/en not_active Ceased
- 1998-03-05 CA CA002231631A patent/CA2231631A1/en not_active Abandoned
- 1998-03-06 BR BR9800844-7A patent/BR9800844A/pt not_active IP Right Cessation
- 1998-03-06 TR TR1998/00403A patent/TR199800403A3/tr unknown
- 1998-03-06 JP JP10054062A patent/JP2938427B2/ja not_active Expired - Fee Related
- 1998-03-06 AR ARP980100999A patent/AR015571A1/es unknown
- 1998-03-09 KR KR1019980007713A patent/KR100280561B1/ko not_active IP Right Cessation
- 1998-03-09 CN CN98106084A patent/CN1193014A/zh active Pending
-
2003
- 2003-11-28 CY CY0300087A patent/CY2392B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU728147B2 (en) | 2001-01-04 |
| US6114541A (en) | 2000-09-05 |
| AU5737498A (en) | 1998-09-10 |
| ATE219056T1 (de) | 2002-06-15 |
| ES2176841T3 (es) | 2002-12-01 |
| KR100280561B1 (ko) | 2001-02-01 |
| KR19980080035A (ko) | 1998-11-25 |
| EP0864564A1 (en) | 1998-09-16 |
| CY2392B1 (en) | 2004-09-10 |
| DK0864564T3 (da) | 2002-09-23 |
| TR199800403A2 (xx) | 1998-09-21 |
| BR9800844A (pt) | 2000-05-02 |
| JP2938427B2 (ja) | 1999-08-23 |
| CA2231631A1 (en) | 1998-09-10 |
| DE69805887T2 (de) | 2003-02-20 |
| DE69805887D1 (de) | 2002-07-18 |
| TR199800403A3 (tr) | 1998-09-21 |
| JPH10273481A (ja) | 1998-10-13 |
| EP0864564B1 (en) | 2002-06-12 |
| ZA981885B (en) | 1998-09-10 |
| CN1193014A (zh) | 1998-09-16 |
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