Identification of a Manufacturing Route of Novel CRF-1 Antagonists Containing a 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine Moiety

被引：12

作者：

Ribecai, Arianna ^{[1
]}

Bacchi, Sergio ^{[1
]}

Delpogetto, Monica ^{[1
]}

Guelfi, Simone ^{[1
]}

Manzo, Angelo Maria ^{[1
]}

Perboni, Alcide ^{[1
]}

Stabile, Paolo ^{[1
]}

Westerduin, Pieter ^{[1
]}

Hourdin, Marie ^{[1
]}

Rossi, Sara ^{[1
]}

Provera, Stefano ^{[2
]}

Turco, Lucilla ^{[2
]}

机构：

[1] GlaxoSmithKline Med Res Ctr, Chem Dev Dept, I-37135 Verona, Italy

[2] GlaxoSmithKline Med Res Ctr, Dept Analyt Chem, I-37135 Verona, Italy

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2010年 / 14卷 / 04期

关键词：

CORTICOTROPIN-RELEASING-FACTOR; EFFICIENT COPPER CATALYST; ARYL HALIDES; BOND FORMATION; N-ARYLATION; ACID; HETEROCYCLES; IMIDAZOLES; AMIDATION; PYRAZOLES;

D O I：

10.1021/op100147h

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A case study on the synthesis of novel CRF-1 antagonists containing the 2,3-dihydro-1H-pyrrolo[2,3-6]pyridine moiety is presented. The development of ever more efficient synthetic routes allowed the progression of three candidates at the same time. A manufacturing route was identified and successfully demonstrated on a pilot-plant scale to prepare 100 kg of the CRF-1 antagonist GW876008.

引用

页码：895 / 901

页数：7

共 25 条

[21] 2-8
[22] A facile halogenation of some hydroxyheterocycles using triphenylphosphine and N-halosuccinimide
Sugimoto, O
Mori, M
Tanji, K
[J]. TETRAHEDRON LETTERS, 1999, 40 (42) : 7477 - 7478
[23] CHARACTERIZATION OF A 41-RESIDUE OVINE HYPOTHALAMIC PEPTIDE THAT STIMULATES SECRETION OF CORTICOTROPIN AND BETA-ENDORPHIN
VALE, W
SPIESS, J
RIVIER, C
RIVIER, J
[J]. SCIENCE, 1981, 213 (4514) : 1394 - 1397
[24] Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol
Whitfield, HJ
Griffin, RJ
Hardcastle, IR
Henderson, A
Meneyrol, J
Mesguiche, V
Sayle, KL
Golding, BT
[J]. CHEMICAL COMMUNICATIONS, 2003, (22) : 2802 - 2803
[25] Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles
Zhang, H
Cai, Q
Ma, DW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 5164 - 5173

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