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5-(2-carboxypyridin-2-yloxy)benz[2,1,3]oxadiazole

中文名称
——
中文别名
——
英文名称
5-(2-carboxypyridin-2-yloxy)benz[2,1,3]oxadiazole
英文别名
2-(benzo[2,1,3]oxadiazol-5-yloxy) nicotinic acid;2-(2,1,3-Benzoxadiazol-5-yloxy)nicotinic acid;2-(2,1,3-benzoxadiazol-5-yloxy)pyridine-3-carboxylic acid
5-(2-carboxypyridin-2-yloxy)benz[2,1,3]oxadiazole化学式
CAS
——
化学式
C12H7N3O4
mdl
——
分子量
257.205
InChiKey
PHWWRHJCMXOENH-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.5
  • 重原子数:
    19
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    98.3
  • 氢给体数:
    1
  • 氢受体数:
    7

反应信息

  • 作为反应物:
    描述:
    5-(2-carboxypyridin-2-yloxy)benz[2,1,3]oxadiazole 、 (+)-2-(4-Aminomethyl-3-fluoro-phenoxy)-propionic acid tert-butyl ester 、 2-(1,3-苯并二氧代-5-氧基)烟酸 、 methyl 2-[4-(aminomethyl)-3-fluorophenoxy]acetate 生成 (+/-)-2-[4-({[2-(benzo[2,1,3]oxadiazol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-propionic acid tert-butyl ester
    参考文献:
    名称:
    ETHER DERIVATIVES USEFUL AS INHIBITORS OF PDE4 ISOZYMES
    摘要:
    以下化合物可用作PDE4的抑制剂,用于治疗由嗜酸性粒细胞的活化和脱颗粒调控的疾病,特别是哮喘、慢性支气管炎和慢性阻塞性肺疾病,其化学式如下:其中取代基如规范中所定义。
    公开号:
    US20070161681A1
  • 作为产物:
    参考文献:
    名称:
    Safety vs Efficiency in the Development of a High-Energy Compound
    摘要:
    A scalable route to 5-(2-carboxy-pyridin-2-yloxy)-benz[1,2,5]-oxadiazole (3) is demonstrated. The synthesis was designed to minimize potential safety issues with a previously practiced route and, in particular, to avoid the handling of 5-hydroxy-benzofurazan, which was found to decompose with a large energy release at relatively low temperatures. The new route builds the benzofurazan moiety onto a nicotinonitrile core to avoid high-energy intermediates with low onset temperatures of decomposition.
    DOI:
    10.1021/op0341059
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文献信息

  • Nicotinamide benzofused-heterocyclyl derivatives useful as selective inhibitors of pde4 isozymes
    申请人:——
    公开号:US20030186989A1
    公开(公告)日:2003-10-02
    Compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructive pulmonary disease, of Formula (1.0.0): 1 wherein R 5 and R 6 are taken together to form a moiety of partial Formulas (1.1.1) through (1.1.5): 2 or a pharmaceutically acceptable salt thereof.
    在治疗由嗜酸性粒细胞的激活和脱颗粒调节的疾病,特别是哮喘、慢性支气管炎和慢性阻塞性肺病中作为PDE4抑制剂有用的化合物,其化学式为(1.0.0): 其中R5和R6一起取代形成部分化学式(1.1.1)至(1.1.5)的基团, 或其药用可接受的盐。
  • [EN] ETHER DERIVATIVES USEFUL AS INHIBITORS OF PDE4 ISOZYMES<br/>[FR] ETHER DERIVATIVES USEFUL AS INHIBITORS OF PDE4 ISOZYMES
    申请人:PFIZER PROD INC
    公开号:WO2002060896A1
    公开(公告)日:2002-08-08
    Compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructive pulmonary disease, of the formula (I) wherein j is 0 or 1, provided that when j is 0, n must be 2; k is 0 or 1; m is 1, 2, or 3; n is 1 or 2; W?1 and W2¿ are -O-; -S(=O)¿t?-, where t is 0, 1, or 2, or -N(R?3¿)-; Y is =C(R1a)-, or -[N∊(O)k]- where k is 0 or 1; R1a is -H, -F, -Cl, -CN, -NO2, -(C1-C4) alkyl, -(C2-C4) alkynyl, fluorinated-(C1-C3) alkyl, fluorinated-(C1-C3) alkoxy, -OR16, or -C(=O)NR22aR22b; R?A and RB¿ are -H, -F, -CF¿3?, -(C1-C4) alkyl, -(C3-C7) cycloalkyl, phenyl, or benzyl substituted by 0-3 R?10; or RA and RB¿ are taken together to form a spiro moiety of the formula (Ia) where r and s are 0-4 provided r + s is ≥1 but not > 5; and XA is -CH¿2?-, -CHF, -CF2, -NR?15¿-, -O-, or -S(=O)¿t?-, where t is 0, 1; R?C and RD¿ are the same as R?A and RB¿ except that one of them must be -H; R?1 and R2¿ are -H, -F, -Cl, -CN, -NO¿2?, -(C1-C4) alkyl, -(C2-C4) alkynyl, fluorinated-(C1-C3) alkyl, -OR?16¿, or -C(=O)NR22aR22b; R3 is -H, -(C¿1?-C3) alkyl, phenyl, benzyl, or -OR?16; R4, R5 and R6¿, D, J¿1? and J2 are defined in the application.
    化合物(I)的公式,用于治疗由嗜酸性粒细胞的激活和脱颗粒调节的疾病,特别是哮喘,慢性支气管炎和慢性阻塞性肺疾病的PDE4抑制剂,其中j为0或1,但当j为0时,n必须为2;k为0或1;m为1、2或3;n为1或2;W1和W2为-O-;-S(=O)t-,其中t为0、1或2,或-N(R3)-;Y为=C(R1a)-,或-[N∊(O)k]-,其中k为0或1;R1a为-H,-F,-Cl,-CN,-NO2,-(C1-C4)烷基,-(C2-C4)炔基,氟代-(C1-C3)烷基,氟代-(C1-C3)烷氧基,-OR16或-C(=O)NR22aR22b;R?A和RB为-H,-F,-CF3,-(C1-C4)烷基,-(C3-C7)环烷基,苯基或苄基,可以由0-3个R10取代;或RA和RB一起形成公式(Ia)的螺环部分,其中r和s为0-4,但r+s≥1但不大于5;XA为-CH2-,-CHF,-CF2,-NR15-,-O-或-S(=O)t-,其中t为0或1;R?C和RD与R?A和RB相同,但其中一个必须为-H;R1和R2为-H,-F,-Cl,-CN,-NO2,-(C1-C4)烷基,-(C2-C4)炔基,氟代-(C1-C3)烷基,-OR16或-C(=O)NR22aR22b;R3为-H,-(C1-C3)烷基,苯基,苄基或-OR16;R4,R5和R6,D,J1和J2在申请中有定义。
  • Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes
    申请人:Pfizer Inc.
    公开号:US20020111495A1
    公开(公告)日:2002-08-15
    Compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructuive pulmonary disease, of the formula: 1 wherein j is 0 or 1, k is 0 or 1, m is 0, 1, or 2; n is 1 or 2; A is selected from the partial Formulas: 2 where q is 1, 2, or 3, W 3 is —O—; —N(R 9 )—; or —OC(═O)—; R 7 is selected from —H; —(C 1 -C 6 ) alkyl, —(C 2 -C 6 ) alkenyl, or —(C 2 -C 6 ) alkynyl substituted by 0 to 3 substituents R 10 ; —(CH 2 ) u —(C 3 -C 7 ) cycloalkyl where u is 0, 1 or 2, substituted by 0 to 3 R 10 ; and phenyl or benzyl substituted by 0 to 3 R 14 ; R 8 is tetrazol-5-yl; 1,2,4-triazol-3-yl; 1,2,4-triazol-3-on-5-yl; 1,2,3-triazol-5-yl; imidazol-2-yl; imidazol-4-yl; imidazolidin-2-on-4-yl; 1,3,4-oxadiazolyl; 1,3,4-oxadiazol-2-on-5-yl; 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-on-3-yl; 1,2,4-oxadiazol-5-yl; 1,2,4-oxadiazol-3-on-5-yl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl; morpholinyl; parathiazinyl; oxazolyl; isoxazolyl; thiazolyl; isothiazolyl; pyrrolyl; pyrazolyl; succinimidyl; glutarimidyl; pyrrolidonyl; 2-piperidonyl; 2-pyridonyl; 4-pyridonyl; pyridazin-3-onyl; pyridyl; pyrimidinyl; pyrazinyl; pyridazinyl; indolyl; indolinyl; isoindolinyl; benzo[b]furanyl; 2,3-dihydrobenzofuranyl; 1,3-dihydroisobenzofuranyl; 2H-1-benzopyranyl; 2-H-chromenyl; chromanyl; benzothienyl; 1H-indazolyl; benzimidazolyl; benzoxazolyl; benzisoxazolyl; benzothiazolyl; benzotriazolyl; benzotriazinyl; phthalazinyl; 1,8-naphthyridinyl; quinolinyl; isoquinolinyl; quinazolinyl; quinoxalinyl; pyrazolo[3,4-d]pyrimidinyl; pyrimido[4,5-d]pyrimidinyl; imidazo[1,2-a]pyridinyl; pyridopyridinyl; pteridinyl; or 1H-purinyl; or A is selected from phosphorous and sulfur acid groups; W is —O—; —S(═O) t —, where t is 0, 1, or 2; or —N(R 3 )—; Y is ═C(R 1 a )—, or —[N (O) k ] where k is 0 or 1; R 4 , R 5 and R 6 are (1) —H; provided that R 5 and R 6 are not both —H at the same time, —F; —Cl; —(C 2 -C 4 ) alkynyl; —R 16 ; —OR 16 ; —S(═O) p R 16 ; —C(═O)R 16 , —C(═O)OR 16 , —C(═O)OR 16 ; —OC(═O)R 16 ; —CN; —NO 2 ; —C(═O)NR 16 R 17 ; —OC(═O)NR 16 R 17 ; —NR 12 a C(═O)NR 16 R 17 ; —NR 12 a C(═NR 12 )NR 16 R 17 ; —NR 12 a C(═NCN)NR 16 R 16 ; —NR 12 a C(═N—NO 2 )NR 15 R 16 ; —C(═NR 12 a )NR 15 R 16 ; —CH 2 C(═NR 12 a )NR 16 R 17 ; —OC(═NR 12 a )NR 16 R 17 ; —OC(═N—NO 2 )NR 16 R 17 ; —NR 16 R 17 ; —CH 2 NR 16 R 17 ; —NR 12 a C(═O)R 16 ; —NR 12 a C(═O)OR 16 ; ═NOR 16 ; —NR 12 a S(═O) p R 17 —S(═O) p NR 16 R 17 ; and —CH 2 C(═NR 12 a )NR 16 R 17 ; (2) —(C 1 -C 4 ) alkyl including dimethyl and —(C 1 -C 4 ) alkoxy substituted with 0 to 3 substituents —F or —Cl; or 0 or 1 substituent (C 1 -C 2 ) alkoxycarbonyl-, (C 1 -C 2 ) alkylcarbonyl-, or (C 1 -C 2 ) alkylcarbonyloxy-; or (3) an aryl or heterocyclic moiety; or (4) R 5 and R 6 are taken together to form a moiety of partial Formulas (1.3.1) through (1.3.15): 3 or a pharmaceutically acceptable salt thereof.
    本发明涉及一种化合物,其在治疗由嗜酸性粒细胞活化和脱颗粒调节的疾病中,特别是哮喘、慢性支气管炎和慢性阻塞性肺疾病中作为PDE4抑制剂有用,其化学式为:其中j为0或1,k为0或1,m为0、1或2;n为1或2;A从部分式中选取:其中q为1、2或3,W3为—O—;—N(R9)—;或—OC(═O)—;R7选自—H;—(C1-C6)烷基、—(C2-C6)烯基或—(C2-C6)炔基,其上可有0至3个取代基R10;—(CH2)u—(C3-C7)环烷基,其中u为0、1或2,其上可有0至3个取代基R10;以及苯基或苄基,其上可有0至3个取代基R14;R8为四唑-5-基;1,2,4-三唑-3-基;1,2,4-三唑-3-酮-5-基;1,2,3-三唑-5-基;咪唑-2-基;咪唑-4-基;咪唑啉-2-酮-4-基;1,3,4-噁二唑基;1,3,4-噁二唑-2-酮-5-基;1,2,4-噁二唑-3-基;1,2,4-噁二唑-5-酮-3-基;1,2,4-噁二唑-5-基;1,2,4-噁二唑-3-酮-5-基;1,2,5-噻二唑基;1,3,4-噻二唑基;吗啉基;对噻嗪基;噁唑基;异噁唑基;噻唑基;异噻唑基;吡咯基;吡唑基;琥珀酰亚胺基;戊二酰亚胺基;吡咯烷基;2-哌啶酮基;2-吡啶酮基;4-吡啶酮基;吡啶嗪-3-酮基;吡啶基;嘧啶基;吡嗪基;吡啶嗪基;吲哚基;吲哚啉基;异吲哚啉基;苯并[b]呋喃基;2,3-二氢苯并呋喃基;1,3-二氢异苯并呋喃基;2H-1-苯并吡喃基;2-H-香豆素基;香豆素基;苯并噻吩基;1H-吲唑基;苯并咪唑基;苯并噁唑基;苯并异噁唑基;苯并噻唑基;苯并三唑基;苯并三唑啉基;邻苯二酚基;1,8-萘啶基;喹啉基;异喹啉基;喹唑啉基;喹啉酮基;吡唑并[3,4-d]嘧啶基;嘧啶并[4,5-d]嘧啶基;咪唑并[1,2-a]吡啶基;吡啶吡啶基;噻吩基;或1H-嘌呤基;或A选自磷和硫酸基;W为—O—;—S(═O)t—,其中t为0、1或2;或—N(R3)—;Y为═C(R1a)—,或—[N(O)k],其中k为0或1;R4、R5和R6为(1) —H;但是当R5和R6同时不为—H时,可以为—F;—Cl;—(C2-C4)炔基;—R16;—OR16;—S(═O)pR16;—C(═O)R16、—C(═O)OR16、—C(═O)OR16;—OC(═O)R16;—CN;—NO2;—C(═O)NR16R17;—OC(═O)NR16R17;—NR12aC(═O)NR16R17;—NR12aC(═NR12)NR16R17;—NR12aC(═NCN)NR16R16;—NR12aC(═N—NO2)NR15R16;—C(═NR12a)NR15R16;—CH2C(═NR12a)NR16R17;—OC(═NR12a)NR16R17;—OC(═N—NO2)NR16R17;—NR16R17;—CH2NR16R17;—NR12aC(═O)R16;—NR12aC(═O)OR16;═NOR16;—NR12aS(═O)pR17—S(═O)pNR16R17;和—CH2C(═NR12a)NR16R17;(2) —(C1-C4)烷基,包括二甲基和—(C1-C4)烷氧基,其上可有0至3个取代基—F或—Cl;或者0或1个取代基(C1-C2)烷氧羰基、(C1-C2)烷基羰基或(C1-C2)烷基羰氧基;或者(3) 芳基或杂环基;或者(4) R5和R6聚合形成部分式(1.3.1)到(1.3.15)中的一个基团;或其药学上可接受的盐。
  • ETHER DERIVATIVES USEFUL AS INHIBITORS OF PDE4 ISOZYMES
    申请人:Marfat Anthony
    公开号:US20070161681A1
    公开(公告)日:2007-07-12
    Compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructive pulmonary disease, of the formula: wherein the substituents are as defined in the specification.
    以下化合物可用作PDE4的抑制剂,用于治疗由嗜酸性粒细胞的活化和脱颗粒调控的疾病,特别是哮喘、慢性支气管炎和慢性阻塞性肺疾病,其化学式如下:其中取代基如规范中所定义。
  • Nicotinamide benzofused-heterocyclyl derivatives useful as selective inhibitors of PDE4 isozymes
    申请人:Pfizer Products Inc.
    公开号:US07354941B2
    公开(公告)日:2008-04-08
    Compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructive pulmonary disease, of Formula (1.0.0): wherein R5 and R6 are taken together to form a moiety of partial Formulas (1.1.1) through (1.1.5): or a pharmaceutically acceptable salt thereof.
    本发明涉及一种化合物,其在治疗由嗜酸性粒细胞的激活和脱颗粒调节的疾病中,特别是哮喘、慢性支气管炎和慢性阻塞性肺疾病中作为PDE4抑制剂有用。该化合物的化学式为(1.0.0),其中R5和R6共同形成部分化学式(1.1.1)至(1.1.5)中的一个,或其药学上可接受的盐。
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