NEW PROCESS FOR THE SYNTHESIS OF IMIDAZO[4,5-B]PYRIDINE DERIVATIVES AS POTENT ORALLY-ACTIVE THROMBOXANE-A2 RECEPTOR ANTAGONISTS

被引：10
|
作者：
NICOLAI, E
CLAUDE, S
TEULON, JM
机构：
[1] Carpibem, Rueil Malmaison, 92500
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 01期
关键词：
D O I：
10.1002/jhet.5570310113
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic route to prepare the 4-[3-(4-chlorophenyl)methyl-6-chloroimidazo[4,5-b]pyridin-2-yl]-3,3-dimethylbutanoic acid (UP 116-77) is described. UP 116-77 is a potent orally active TXA2/PGH2 receptor antagonist currently under pharmacological investigation. Its development needed a suitable synthesis for industrial processing. The cyclization of 3-amino-5-chloro-2-(4-chlorophenyl)methylaminopyridine 4 with 3,3-dimethylglutaric anhydride in refluxing acetic acid affords a new efficient and simple way to UP 116-77 and subsequently to various 2-substituted imidazo[4,5-b]pyridine derivatives.
引用
收藏
页码：73 / 75
页数：3
相关论文
共 50 条
  • [1] POTENT, ORALLY ACTIVE IMIDAZO[4,5-B]PYRIDINE ANGIOTENSIN-II RECEPTOR ANTAGONISTS
    MANTLO, NB
    CHAKRAVARTY, PK
    ONDEYKA, D
    CHEN, A
    CAMARA, VJ
    CHANG, RSL
    LOTTI, VJ
    SIEGL, PKS
    PATCHETT, AA
    GREENLEE, WJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 71 - MEDI
  • [2] POTENT, ORALLY ACTIVE IMIDAZO[4,5-B]PYRIDINE-BASED ANGIOTENSIN-II RECEPTOR ANTAGONISTS
    MANTLO, NB
    CHAKRAVARTY, PK
    ONDEYKA, DL
    SIEGL, PKS
    CHANG, RS
    LOTTI, VJ
    FAUST, KA
    CHEN, TB
    SCHORN, TW
    SWEET, CS
    EMMERT, SE
    PATCHETT, AA
    GREENLEE, WJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) : 2919 - 2922
  • [3] Synthesis of new imidazo[4,5-b]pyridine derivatives
    Bukowski, L
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (07): : 937 - 944
  • [4] Synthesis of new imidazo-[4,5-b]pyridine derivatives
    Bukowski L.
    Chemistry of Heterocyclic Compounds, 2002, 38 (07) : 828 - 835
  • [5] A HIGHLY POTENT, ORALLY-ACTIVE IMIDAZO[4,5-B]PYRIDINE BIPHENYLACYLSULFONAMIDE (MK-996-L-159,282) - A NEW ANGIOTENSIN-II RECEPTOR ANTAGONIST
    CHAKRAVARTY, PK
    NAYLOR, EM
    CHEN, A
    CHANG, RSL
    CHEN, TB
    FAUST, KA
    LOTTI, VJ
    KIVLIGHN, SD
    GABLE, RA
    ZINGARO, GJ
    SCHORN, TW
    SCHAFFER, LW
    BROTEN, TP
    SIEGL, PKS
    PATCHETT, AA
    GREENLEE, WJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) : 4068 - 4072
  • [6] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NOVEL BENZIMIDAZOLE AND IMIDAZO[4,5-B]PYRIDINE ACID-DERIVATIVES AS THROMBOXANE-A(2) RECEPTOR ANTAGONISTS
    NICOLAI, E
    GOYARD, J
    BENCHETRIT, T
    TEULON, JM
    CAUSSADE, F
    VIRONE, A
    DELCHAMBRE, C
    CLOAREC, A
    JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (09) : 1175 - 1187
  • [7] SYNTHESIS OF SOME NEW IMIDAZO[4,5-B]PYRIDINE DERIVATIVES USING 2-CYANOMETHYL-1-METHYL-1H-IMIDAZO[4,5-B]PYRIDINE
    Bukowski, L.
    Zwolska, Zofia
    Augustynowicz-Kopec, Ewa
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (07) : 879 - 887
  • [8] Synthesis and antituberculotic activity of some new imidazo[4,5-b]pyridine derivatives
    Bukowski, L.
    Zwolska, Z.
    Augustynowicz-Kopec, E.
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2006, (10): : 1571 - 1579
  • [9] Synthesis and antituberculotic activity of some new imidazo[4,5-b]pyridine derivatives
    Bukowski L.
    Zwolska Z.
    Augustynowicz-Kopec E.
    Chemistry of Heterocyclic Compounds, 2006, 42 (10) : 1358 - 1365
  • [10] SYNTHESIS OF NEW IMIDAZO[1,2-B]PYRIDAZINE ISOSTERES OF POTENT IMIDAZO[4,5-B]PYRIDINE ANGIOTENSIN-II ANTAGONISTS
    WALSH, TF
    FITCH, KJ
    MACCOSS, M
    CHANG, RSL
    KIVLIGHN, SD
    LOTTI, VJ
    SIEGL, PKS
    PATCHETT, AA
    GREENLEE, WJ
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (01) : 219 - 222
12345