AR070008A1 - Proceso e intermediarios para la sintesis de compuestos de 3,4- dioxo-1- ciclobuteno 1,2- sustituidos - Google Patents
Proceso e intermediarios para la sintesis de compuestos de 3,4- dioxo-1- ciclobuteno 1,2- sustituidosInfo
- Publication number
- AR070008A1 AR070008A1 ARP080102866A ARP080102866A AR070008A1 AR 070008 A1 AR070008 A1 AR 070008A1 AR P080102866 A ARP080102866 A AR P080102866A AR P080102866 A ARP080102866 A AR P080102866A AR 070008 A1 AR070008 A1 AR 070008A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- substituted
- branched
- cyclic
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 9
- 238000000034 method Methods 0.000 title abstract 5
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- RGBVWCQARBEPPW-UHFFFAOYSA-N cyclobut-3-ene-1,2-dione Chemical compound O=C1C=CC1=O RGBVWCQARBEPPW-UHFFFAOYSA-N 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000013078 crystal Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 amino-hydroxy-benzamide compound Chemical class 0.000 abstract 2
- 125000000129 anionic group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- 230000001404 mediated effect Effects 0.000 abstract 2
- 102000019034 Chemokines Human genes 0.000 abstract 1
- 108010012236 Chemokines Proteins 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000001351 cycling effect Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Esta solicitud revela un proceso para la preparacion de compuestos de 3,4-dioxo-1-ciclobuteno 1,2-sustituidos, los cuales tienen utilidad, por ejemplo, en el tratamiento de enfermedades mediadas por CXC quimioquina, e intermediarios utiles en su síntesis. Reivindicacion 1: Un proceso para elaborar los compuestos de formula (1), donde el proceso comprende: (a) formar el dialquil-escuarato de formula (2) in situ haciendo reaccionar (R3-O-)3-CH con ácido escuárico, donde R3 se selecciona de alquilos rectos, ramificados y cíclicos de hasta 10 átomos de carbono; (b) hacer reaccionar el compuesto amino-hidroxi-benzamida de formula (3) donde [Anion-] es un resto anionico monovalente, con el dialquilescuarato del paso ôaö para formar el compuesto de formula (4), donde R3 es como se definio anteriormente; (c) hacer reaccionar el compuesto de formula (4) formado en el paso ôbö con un compuesto amino-furano de base libre de formula (5) formado in situ, donde R2 es H o un sustituyente que comprende de 1 átomo de carbono a aproximadamente 10 átomos de carbono seleccionado de restos alquilo rectos, ramificados o cíclicos, y restos alquilo rectos, ramificados o cíclicos sustituidos, para proporcionar el compuesto de formula (1); y (d) opcionalmente, precipitar el compuesto de formula (1) mediante lo siguientes procedimientos: (i) ciclos sucesivos de concentracion de la mezcla de reaccion formada en el paso ôcö por destilacion, seguida de la adicion de una alícuota de un alcohol; (ii) agregando una alícuota del alcohol usado en el paso ôd(i)ö ácido acético al concentrado formado en el paso ôiö; (iii) calentando la solucion formada en el paso ôiiö; (iv) agregando una alícuota de agua y cristales semilla a la solucion caliente del paso ôiiiö; (v) ciclando la temperatura de la solucion sembrada preparada en el paso ôivö hasta que se formen cristales del compuesto de formula (1) con el tamano deseado; y (vi) opcionalmente, aislando los cristales de la mezcla preparada en el paso ôvö. Reivindicacion 26: Un compuesto de formula (6), donde ôAnion-ö es un resto anionico monovalente. Reivindicacion 27: Un compuesto de formula (7), donde [R-Anion-] es un anion monovalente y R2 es hidrogeno o un sustituyente alquilo que tiene de 1 átomo de carbono a aproximadamente 10 átomos de carbono y es un resto alquilo recto, ramificado o cíclico, o un resto alquilo recto sustituido, ramificado sustituido o cíclico sustituido.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95831107P | 2007-07-03 | 2007-07-03 | |
| US95831307P | 2007-07-03 | 2007-07-03 | |
| US95831707P | 2007-07-03 | 2007-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR070008A1 true AR070008A1 (es) | 2010-03-10 |
Family
ID=39816750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080102866A AR070008A1 (es) | 2007-07-03 | 2008-07-02 | Proceso e intermediarios para la sintesis de compuestos de 3,4- dioxo-1- ciclobuteno 1,2- sustituidos |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8519168B2 (es) |
| EP (1) | EP2178826B1 (es) |
| JP (1) | JP5243539B2 (es) |
| CN (1) | CN101932553A (es) |
| AR (1) | AR070008A1 (es) |
| CA (1) | CA2692269A1 (es) |
| TW (1) | TW200914433A (es) |
| WO (1) | WO2009005801A1 (es) |
| ZA (1) | ZA201000394B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA103198C2 (en) | 2008-08-04 | 2013-09-25 | Новартис Аг | Squaramide derivatives as cxcr2 antagonists |
| BR112014004963A2 (pt) | 2011-09-02 | 2017-03-21 | Novartis Ag | sal de colina do composto anti-inflamatório ciclobutanodiona substituído |
| TWI724056B (zh) | 2015-11-19 | 2021-04-11 | 美商卡默森屈有限公司 | Ｃｘｃｒ２抑制劑 |
| TWI734715B (zh) | 2015-11-19 | 2021-08-01 | 美商卡默森屈有限公司 | 趨化因子受體調節劑 |
| WO2019067332A1 (en) * | 2017-09-27 | 2019-04-04 | Merck Sharp & Dohme Corp. | COMPOSITIONS AND METHODS FOR TREATING CANCER THROUGH A COMBINATION OF PROGRAMMED DEATH ANTIBODY ANTIBODIES (PD-1) AND A CXCR2 ANTAGONIST |
| MA50424A (fr) | 2018-01-08 | 2020-08-26 | Chemocentryx Inc | Méthodes de traitement du psoriasis pustuleux généralisé avec un antagoniste de ccr6 ou cxcr2 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0395144A (ja) | 1989-08-04 | 1991-04-19 | Ono Pharmaceut Co Ltd | アミノフェノール誘導体の製造方法 |
| SI1381590T1 (sl) * | 2001-04-16 | 2007-10-31 | Schering Corp | 3,4-disubstituirani ciklobuten-1,2-dioni kot ligandi CXC-kemokinskega receptorja |
| US20040106794A1 (en) | 2001-04-16 | 2004-06-03 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| US7132445B2 (en) | 2001-04-16 | 2006-11-07 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| US20040053953A1 (en) * | 2002-03-18 | 2004-03-18 | Schering Corporation | Treatment of chemokine mediated diseases |
| CA2522748C (en) * | 2003-04-18 | 2011-06-28 | Schering Corporation | Synthesis of 2-hydroxy-n,n-dimethyl-3-[[2-[1(r)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide |
| WO2005068460A1 (en) * | 2003-12-22 | 2005-07-28 | Schering Corporation | Isothiazole dioxides as cxc- and cc- chemokine receptor ligands |
| AR047739A1 (es) | 2004-01-30 | 2006-02-15 | Schering Corp | Polimorfos cristalinos de un ligando receptor de cxc-quimiocina |
| WO2008005570A1 (en) | 2006-07-07 | 2008-01-10 | Schering Corporation | 3,4-di-substituted cyclobutene-1,2-diones as cxc-chemokine receptor ligands |
-
2008
- 2008-07-01 CA CA002692269A patent/CA2692269A1/en not_active Abandoned
- 2008-07-01 EP EP08779918.5A patent/EP2178826B1/en active Active
- 2008-07-01 CN CN2008801061950A patent/CN101932553A/zh active Pending
- 2008-07-01 JP JP2010514858A patent/JP5243539B2/ja not_active Expired - Fee Related
- 2008-07-01 WO PCT/US2008/008187 patent/WO2009005801A1/en active Application Filing
- 2008-07-01 US US12/665,913 patent/US8519168B2/en active Active
- 2008-07-02 TW TW097124891A patent/TW200914433A/zh unknown
- 2008-07-02 AR ARP080102866A patent/AR070008A1/es not_active Application Discontinuation
-
2010
- 2010-01-19 ZA ZA2010/00394A patent/ZA201000394B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200914433A (en) | 2009-04-01 |
| US20110160469A1 (en) | 2011-06-30 |
| ZA201000394B (en) | 2012-06-27 |
| EP2178826B1 (en) | 2017-05-17 |
| EP2178826A1 (en) | 2010-04-28 |
| JP5243539B2 (ja) | 2013-07-24 |
| CA2692269A1 (en) | 2009-01-08 |
| CN101932553A (zh) | 2010-12-29 |
| JP2010532356A (ja) | 2010-10-07 |
| WO2009005801A1 (en) | 2009-01-08 |
| US8519168B2 (en) | 2013-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |