AR044027A1 - Sintesis de 2-hidroxi-n,n-dimetil-3-[[2-[1(r) - (5-metil-2-furanil)propil]amino]- 3,4-dioxo-1-ciclobuten-1-il]amino]benzamida - Google Patents
Sintesis de 2-hidroxi-n,n-dimetil-3-[[2-[1(r) - (5-metil-2-furanil)propil]amino]- 3,4-dioxo-1-ciclobuten-1-il]amino]benzamidaInfo
- Publication number
- AR044027A1 AR044027A1 ARP040101294A ARP040101294A AR044027A1 AR 044027 A1 AR044027 A1 AR 044027A1 AR P040101294 A ARP040101294 A AR P040101294A AR P040101294 A ARP040101294 A AR P040101294A AR 044027 A1 AR044027 A1 AR 044027A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- amino
- produce
- transforming
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 29
- 230000001131 transforming effect Effects 0.000 abstract 4
- 125000006239 protecting group Chemical group 0.000 abstract 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Se revela un proceso para preparar el compuesto de fórmula (1) y también se revelan compuestos intermediarios. Reivindicación 1: Un proceso para preparar un compuesto de fórmula (1), que comprende: a) transformar el compuesto de fórmula (2), en un compuesto de fórmula (3), donde A, en los compuestos de fórmula (2) y (3), se selecciona del grupo conformado por Br, Cl y I; b) hidrogenar el compuesto de fórmula (3) con un catalizador de hidrogenación adecuado bajo presión de hidrógeno, para formar el compuesto intermediario de fórmula (4), c) hacer reaccionar el compuesto de fórmula (4) con un compuesto de fórmula (5), en el cual R representa alquilo (C1-10), para producir un compuesto de fórmula (6), d) transformar el compuesto de fórmula (7), en un compuesto de fórmula (8), e) agregar un grupo protector al compuesto de fórmula (8) para producir un compuesto de fórmula (9), en el cual G representa un grupo protector; f) hacer reaccionar el compuesto de fórmula (8) con un reactivo organometálico adecuado, seguido de procesamiento, para producir un compuesto de fórmula (10), g) eliminar el grupo protector (G) del compuesto de fórmula (10) para producir un compuesto de fórmula (11), h) transformar el compuesto de fórmula (11) en un imino compuesto intermediario de fórmula (12), i) transformar el imino compuesto intermediario de fórmula (12) en la sal de fórmula (13), j) hacer reaccionar el compuesto de fórmula (13) con el compuesto de fórmula (6) para producir el compuesto de fórmula (1); o k) transformar el compuesto de fórmula (13) en la amina libre, y hacer reaccionar el compuesto de fórmula (14) con el compuesto de fórmula (6) para producir el compuesto de fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46377303P | 2003-04-18 | 2003-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR044027A1 true AR044027A1 (es) | 2005-08-24 |
Family
ID=33310818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040101294A AR044027A1 (es) | 2003-04-18 | 2004-04-16 | Sintesis de 2-hidroxi-n,n-dimetil-3-[[2-[1(r) - (5-metil-2-furanil)propil]amino]- 3,4-dioxo-1-ciclobuten-1-il]amino]benzamida |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US7071342B2 (es) |
| EP (2) | EP2168956B8 (es) |
| JP (2) | JP4440917B2 (es) |
| CN (3) | CN100448860C (es) |
| AR (1) | AR044027A1 (es) |
| AT (1) | ATE457307T1 (es) |
| CA (1) | CA2522748C (es) |
| DE (1) | DE602004025458D1 (es) |
| ES (1) | ES2338657T3 (es) |
| HK (1) | HK1078315A1 (es) |
| MX (1) | MXPA05011183A (es) |
| SG (1) | SG167671A1 (es) |
| WO (1) | WO2004094398A2 (es) |
| ZA (3) | ZA200508129B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040106794A1 (en) * | 2001-04-16 | 2004-06-03 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| DE602005022986D1 (de) * | 2004-01-30 | 2010-09-30 | Schering Corp | Kristalline polymorphe eines cxc-chemokinrezeptorliganden |
| CN101500544B (zh) | 2006-06-12 | 2012-08-08 | 先灵公司 | Cxcr2或cxcr1与cxcr2两者的选择性拮抗剂的药物制剂和组合物及其用于治疗炎性疾病的使用方法 |
| CN101932553A (zh) * | 2007-07-03 | 2010-12-29 | 先灵公司 | 合成1,2-取代的3,4-二氧代-1-环丁烯化合物的方法和中间体 |
| JP2010532357A (ja) * | 2007-07-05 | 2010-10-07 | シェーリング コーポレイション | １，２−置換３，４−ジオキソ−１−シクロブテン化合物における制御された結晶サイズのための方法 |
| KR20130087387A (ko) * | 2010-06-16 | 2013-08-06 | 데이진 가부시키가이샤 | 고리형 카르보디이미드 화합물의 중간체의 제조 방법 |
| WO2012147897A1 (ja) * | 2011-04-25 | 2012-11-01 | 住友化学株式会社 | アミン化合物の製造方法 |
| 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 |
| EP3737366A4 (en) | 2018-01-08 | 2022-07-27 | ChemoCentryx, Inc. | METHOD OF TREATMENT OF GENERALIZED PUSTULOUS PSORIASIS WITH AN ANTAGONIST OF CCR6 OR CXCR2 |
| TW202128643A (zh) * | 2019-11-11 | 2021-08-01 | 美商富曼西公司 | 用於製備３—溴—１—（３—氯吡啶—２—基）—１ｈ—吡唑—５—羧酸乙酯的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2791613A (en) * | 1953-08-24 | 1957-05-07 | Columbia Southern Chem Corp | Metahaloaniline production using copper oxide-chromic oxide catalysts |
| CH691112A5 (de) | 1995-03-14 | 2001-04-30 | Sumitomo Chemical Co | Verfahren zur Herstellung von Kristallen eines Schwefelsäuresalzes des 3-Amino-2-hydroxyacetophenons mit hoher Schüttdiche und verbesserten Fliesseigenschaften . |
| ZA991105B (en) * | 1998-03-04 | 2000-02-11 | Searle & Co | Synthesis of chiral beta-amino acids. |
| IL156793A0 (en) * | 2001-02-02 | 2004-02-08 | Schering Corp | 3,4-di-substituted cyclobutene-1,2-diones as cxc chemokine receptor antagonists |
| US20030204085A1 (en) * | 2001-02-02 | 2003-10-30 | Taveras Arthur G. | 3, 4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor antagonists |
| US20040106794A1 (en) * | 2001-04-16 | 2004-06-03 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| MY149050A (en) | 2001-04-16 | 2013-07-15 | Merck Sharp & Dohme | 3,4 di-substituted cyclobutene-1,2-diones as cxc-chemokine receptor ligands |
| WO2003080053A1 (en) * | 2002-03-18 | 2003-10-02 | Schering Corporation | Combination treatments for chemokine-mediated diseases |
-
2004
- 2004-04-16 EP EP09014248.0A patent/EP2168956B8/en not_active Expired - Lifetime
- 2004-04-16 DE DE602004025458T patent/DE602004025458D1/de not_active Expired - Lifetime
- 2004-04-16 CN CNB2004800165225A patent/CN100448860C/zh not_active Expired - Fee Related
- 2004-04-16 US US10/826,456 patent/US7071342B2/en not_active Expired - Lifetime
- 2004-04-16 SG SG200717017-8A patent/SG167671A1/en unknown
- 2004-04-16 CA CA2522748A patent/CA2522748C/en not_active Expired - Fee Related
- 2004-04-16 AT AT04759956T patent/ATE457307T1/de not_active IP Right Cessation
- 2004-04-16 CN CN2008101738953A patent/CN101514193B/zh not_active Expired - Fee Related
- 2004-04-16 JP JP2006501278A patent/JP4440917B2/ja not_active Expired - Fee Related
- 2004-04-16 AR ARP040101294A patent/AR044027A1/es not_active Application Discontinuation
- 2004-04-16 MX MXPA05011183A patent/MXPA05011183A/es active IP Right Grant
- 2004-04-16 EP EP04759956A patent/EP1615903B1/en not_active Expired - Lifetime
- 2004-04-16 CN CN200810173891.5A patent/CN101514168B/zh not_active Expired - Fee Related
- 2004-04-16 WO PCT/US2004/011882 patent/WO2004094398A2/en active Application Filing
- 2004-04-16 ES ES04759956T patent/ES2338657T3/es not_active Expired - Lifetime
-
2005
- 2005-10-07 ZA ZA200508129A patent/ZA200508129B/en unknown
-
2006
- 2006-01-23 HK HK06101053.6A patent/HK1078315A1/xx not_active IP Right Cessation
- 2006-05-09 US US11/430,687 patent/US7462740B2/en active Active
-
2008
- 2008-01-16 ZA ZA200800486A patent/ZA200800486B/en unknown
- 2008-01-16 ZA ZA200800487A patent/ZA200800487B/en unknown
- 2008-10-17 US US12/253,356 patent/US7910775B2/en active Active
-
2009
- 2009-12-01 JP JP2009273993A patent/JP5202503B2/ja not_active Expired - Fee Related
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |