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Volumn 15, Issue 2, 2011, Pages 343-352

The development of a robust process for a CRF1 receptor antagonist

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE PHARMACEUTICAL INGREDIENTS; CATALYTIC PROCESS; CHLORINATING AGENTS; CORTICOTROPIN-RELEASING FACTORS; CYCLIZATIONS; OXYCHLORIDES; REACTION CONDITIONS; RECEPTOR ANTAGONISTS; SEMICARBAZIDE;

EID: 79952823079     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op100270u     Document Type: Article
Times cited : (19)

References (47)
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    • Zhou, J.; Oh, L. M.; Ma, P. U.S. Pat. 6,562,965, 2003.
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  • 13
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    • United States Environmental Protection Agency, (created in April 1992; revised in January 2000; updated in November 2007); (accessed September 9, 2010)
    • Hydrazine Hazard Summary; United States Environmental Protection Agency, (created in April 1992; revised in January 2000; updated in November 2007) 2007; http://www.epa.gov/ttn/atw/hlthef/hydrazin.html (accessed September 9, 2010).
    • (2007) Hydrazine Hazard Summary
  • 14
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    • JP 2001302658
    • The pyridyl starting material was obtained from commercial sources or by custom synthesis, see: Miyata, H.; Oki, K.; Morikawa, K. JP 2001302658, 2001.
    • (2001)
    • Miyata, H.1    Oki, K.2    Morikawa, K.3
  • 15
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    • CN 1088574
    • Yu, Z. CN 1088574, 1994
    • (1994)
    • Yu, Z.1
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    • 79952846182 scopus 로고    scopus 로고
    • To ensure full dissolution of 16, 4 equiv were necessary
    • To ensure full dissolution of 16, 4 equiv were necessary.
  • 23
    • 79952849318 scopus 로고    scopus 로고
    • 2O as solvent did not lead to appreciable levels of conversion.
    • 2O as solvent did not lead to appreciable levels of conversion.
  • 24
    • 79952828754 scopus 로고    scopus 로고
    • Pure regioisomers trans - 13a and semicarbazone 13b were isolated and used for characterization. The cis -isomer was not observed.
    • Pure regioisomers trans-13a and semicarbazone 13b were isolated and used for characterization. The cis -isomer was not observed.
  • 25
    • 79952838282 scopus 로고    scopus 로고
    • The isomer ratio was estimated by careful solid-state NMR techniques as 13a and 13b were observed to readily interconvert in solution.
    • The isomer ratio was estimated by careful solid-state NMR techniques as 13a and 13b were observed to readily interconvert in solution.
  • 26
    • 79952842005 scopus 로고    scopus 로고
    • 2O prior to the start of the subsequent API step.
    • 2O prior to the start of the subsequent API step.
  • 27
    • 79952860725 scopus 로고    scopus 로고
    • 2O afforded the monohydrate. Prolonged exposure of anhydrous 10 as a slurry in the presence of water at room temperature did not produce the monohydrate form.
    • 2O afforded the monohydrate. Prolonged exposure of anhydrous 10 as a slurry in the presence of water at room temperature did not produce the monohydrate form.
  • 28
    • 79952848253 scopus 로고    scopus 로고
    • With 1 mol % of DBU, the solubility of 10 is 2 mg/mL whereas with 5 mol % it is 25 mg/mL.
    • With 1 mol % of DBU, the solubility of 10 is 2 mg/mL whereas with 5 mol % it is 25 mg/mL.
  • 32
    • 79952829174 scopus 로고    scopus 로고
    • Similar conditions were utilized for a related molecule, see ref 6
    • Similar conditions were utilized for a related molecule, see ref 6.
  • 36
    • 79952843742 scopus 로고    scopus 로고
    • A similar dimeric impurity has been observed, see ref 20.
    • A similar dimeric impurity has been observed, see ref 20.
  • 37
    • 79952860298 scopus 로고    scopus 로고
    • The influence of solvent for the chlorination reaction is under investigation and will be reported in due course
    • The influence of solvent for the chlorination reaction is under investigation and will be reported in due course.
  • 39
    • 79952844699 scopus 로고    scopus 로고
    • CN 101445485 A 20090603 (CAN 151:78133 AN 2009:689505).
    • Aiqing, F. Zhuanli, F. Shuomingshu, G. S. CN 101445485 A 20090603 (CAN 151:78133 AN 2009:689505), 2009.
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    • Aiqing, F.1    Zhuanli, F.2    Shuomingshu, G.S.3
  • 40
    • 79952820954 scopus 로고    scopus 로고
    • The exact role of DABCO in the catalyzed chlorination is currently under investigation and will be disclosed in due course
    • The exact role of DABCO in the catalyzed chlorination is currently under investigation and will be disclosed in due course.
  • 45
    • 79952850160 scopus 로고    scopus 로고
    • 3 was added in 4 min, resulting in an increase of batch temperature from -4 to 3.5 °C with the jacket temperature set to -10 °C.
    • 3 was added in 4 min, resulting in an increase of batch temperature from -4 to 3.5 °C with the jacket temperature set to -10 °C.
  • 47
    • 79952822025 scopus 로고    scopus 로고
    • Enamine formation may occur via hydride transfer as described in ref 32 or as shown below
    • Enamine formation may occur via hydride transfer as described in ref 32 or as shown below


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