3-bromo-4-(3-fluorophenyl)-4-oxobutyric acid | 870862-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-4-(3-fluorophenyl)-4-oxobutyric acid
• 英文别名: 3-Bromo-4-(3-fluorophenyl)-4-oxobutanoic acid
• CAS: 870862-09-2
• 化学式: C₁₀H₈BrFO₃
• 分子量: 275.074
• InChiKey: QZGACLGBLNYAOK-UHFFFAOYSA-N

物化性质

• 沸点：
  378.2±37.0 °C(predicted)
• 密度：
  1.653±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-4-(3-fluorophenyl)-4-oxobutyric acid 、 1,1-二苯基硫脲 以 乙腈 为溶剂， 以31%的产率得到[2-diphenylamino-4-(3-fluorophenyl)-thiazol-5-yl]-acetic acid
  参考文献：
  名称：

  WO2007/62797

  摘要：

  公开号：
• 作为产物：
  描述：

  4-(3-氟苯基)-4-氧代丁酸 在 溴 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 3-bromo-4-(3-fluorophenyl)-4-oxobutyric acid
  参考文献：
  名称：

  WO2007/62797

  摘要：

  公开号：

文献信息

• [EN] SUBSTITUTED THIAZOLEACETIC AS CRTH2 LIGANDS<br/>[FR] ACIDES THIAZOLEACETIQUES SUBSTITUES EN TANT QUE LIGANDS CRTH2
  申请人：7TM PHARMA AS

  公开号：WO2005116001A1

  公开（公告）日：2005-12-08

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis; wherein X1 is -S-, -O-, -N=N-. -NR7-, -CR7=CR8-, -CR7=N-, wherein R7 and R8 are independently hydrogen or C1-C3 alkyl; A is a carboxyl group -COOH, or a carboxyl bioisostere; rings Ar2 and Ar3 each independently represent a phenyl or 5- or 6­-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; ring B is as defined for Ar2 and Ar3, or an optionally substituted N-­pyrrolidinyl, N-piperidinyl or N-azepinyl ring; s is 0 or 1; L1, L2 and L4 are linker radicals as defined in the description; Q1 and Q2 represent substituents as defined in the description.

  式(I)的化合物对于治疗对CRTH2受体活性调节敏感的疾病有用，如哮喘、鼻炎、过敏性气道综合征和过敏性鼻支气管炎；其中X1为-S-，-O-，-N=N-，-NR7-，-CR7=CR8-，-CR7=N-，其中R7和R8独立地为氢或C1-C3烷基；A为羧基-COOH，或羧基生物异构体；环Ar2和环Ar3各自独立地表示苯基或5-或6-成员的单环杂芳基环，或由5-或6-成员的碳环或杂环环组成的双环系统，该环或环系可以选择性地被取代；环B的定义与环Ar2和环Ar3相同，或者是一个可选择性取代的N-吡咯烷基，N-哌啶基或N-氮杂七元环；s为0或1；L1、L2和L4为描述中定义的连接基；Q1和Q2表示描述中定义的取代基。
• Substituted Thiazoleacetic Acid as Crth2 Ligands
  申请人：Ulven Trond

  公开号：US20080119456A1

  公开（公告）日：2008-05-22

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis; wherein X 1 is —S—, —O—, —N═N—. —NR 7 —, —CR 7 ═CR 8 —, —CR 7 ═N—, wherein R 7 and R 8 are independently hydrogen or C 1 -C 3 alkyl; A is a carboxyl group —COOH, or a carboxyl bioisostere; rings Ar 2 and Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; ring B is as defined for Ar 2 and Ar 3 , or an optionally substituted N-pyrrolidinyl, N-piperidinyl or N-azepinyl ring; s is 0 or 1; L1, L2 and L4 are linker radicals as defined in the description; Q 1 and Q 2 represent substituents as defined in the description.

  式(I)的化合物对于治疗对CRTH2受体活性调节敏感的疾病，如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎是有用的；其中X1为—S—、—O—、—N═N—、—NR7—、—CR7═CR8—、—CR7═N—，其中R7和R8独立地为氢或C1-C3烷基；A为羧基—COOH，或羧基生物同位素；环Ar2和Ar3各自表示苯基或5-或6-成员单环杂芳基环，或由5-或6-成员碳环或杂环环组成的双环系统，该环或环系统可以选择性地被取代；环B与Ar2和Ar3的定义相同，或是一个可以选择性地被取代的N-吡咯烷基、N-哌啶基或N-氮杂环己基环；s为0或1；L1、L2和L4为描述中定义的连接基团；Q1和Q2表示描述中定义的取代基。
• Exploration of SAR features by modifications of thiazoleacetic acids as CRTH2 antagonists
  作者：Marie Grimstrup、Jean-Marie Receveur、Øystein Rist、Thomas M. Frimurer、Peter Aadal Nielsen、Jesper M. Mathiesen、Thomas Högberg

  DOI：10.1016/j.bmcl.2010.01.092

  日期：2010.3

  The SAR features have been further explored for (2-benzhydryl-4-phenyl-thiazol-5-yl) acetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. The introduction of a nitrogen or a methyl substituent in the benzhydrylic position offer two alternative drugable scaffolds attractive for unsymmetrically substituted derivatives. An imidazole analogue lacks activity due to formation of a favored coplanar intramolecular hydrogen bond. The pyrimidine derivative 18 represents a potent and selective compound that will be subject to continued investigations. (C) 2010 Elsevier Ltd. All rights reserved.
• SUBSTITUTED THIAZOLEACETIC ACIDS AS CRTH2 LIGANDS
  申请人：7TM Pharma A/S

  公开号：EP1758874A1

  公开（公告）日：2007-03-07
• [EN] AMINO-SUBSTITUTED AZO-HETEROCYCLIC COMPOUNDS FOR TREATING INFLAMMATORY CONDITIONS<br/>[FR] COMPOSES AZO-HETEROCYCLIQUES AMINO-SUBSTITUES DESTINES AU TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：7TM PHARMA AS

  公开号：WO2007062797A1

  公开（公告）日：2007-06-07

  [EN] Compounds of formula (I) are CRTH2 antagonists, useful in the treatment of inflammatory, autoimmune, respiratory or allergy disease: wherein X₁ is -S-, -O-, -N=N-. -NR₅-, -CR₅=CR₆-, -CR₅=N-, wherein R₅ and R₆ are independently hydrogen or C₁-C₃ alkyl; R₁ is hydrogen or C₁-C₃ alkyl or cyclopropyl; R₂ is an optionally substituted phenyl or 5- or 6-membered monocyclic heteroaryl ring; R₃ is an optionally substituted carbocyclic ring of 3 to 7 ring atoms, or an optionally substituted 4-, 5- or 6-membered monocyclic heterocyclic ring; R₄ is a group other than hydrogen, methyl or ethyl of formula Q-[Alk¹]_m-[X]_n-[Alk²]_p-[Z}_s- wherein m, n p, and s are independently 0 or 1 ; Q is hydrogen or an optionally substituted 4-, 5- or 6-membered monocyclic heterocyclic ring; Alk¹ and Alk² are independently optionally substituted C₁-C₃ alkylene radicals; X is -O-, -S-, -C(=O)-, - S(=O)-, -S(=O)₂-, -CH(R₇)-, -N(R₇)-, or, in either orientation -SO₂N(R₇)- or - C(=O)N(R₇)-, wherein R₇ is hydrogen, or R₇ represents a C₂-C₄ bridge between the C or N atom of X to which it is attached and a carbon atom of Alk² and Z is -CH₂, - C(=O) or -S(=O)₂.
  [FR] L'invention concerne des composés représentés par la formule générale (I). Ces composés sont des antagonistes du récepteur CRTH2 destinés au traitement de maladies inflammatoires, autoimmunes, respiratoires ou allergiques. Dans la formule générale (I), X₁ désigne -S-, -O-, -N=N-, -NR₅-, -CR₅=CR₆-, -CR₅=N-, R₅ et R₆ désignant chacun un atome d'hydrogène ou un groupe alkyle C₁-C₃; R₁ désigne un atome d'hydrogène ou un groupe alkyle C₁-C₃ ou cyclopropyle; R₂ désigne un groupe phényle éventuellement substitué ou un cycle hétéroaryle comportant 5 ou 6 éléments; R₃ désigne un cycle carbocyclique éventuellement substitué comportant 3 à 7 atomes par cycle, ou un cycle hétérocyclique monocyclique éventuellement substitué, comportant 4, 5 ou 6 éléments; R₄ désigne un groupe autre que hydrogène, méthyle ou éthyle représenté par la formule générale Q-[Alk¹]_m-[X]_n-[Alk²]_p-[Z]_s- dans laquelle m, n, p et s valent chacun 0 ou 1; Q désigne un atome d'hydrogène ou un cycle hétérocyclique monocyclique éventuellement substitué, comportant 4, 5 ou 6 éléments; Alk¹ et Alk² désignent chacun des radicaux alkylène C₁-C₃ éventuellement substitués; X désigne -O-, -S-, -C(=O)-, -S(=O)-, -S(=O)₂-, -CH(R₇)-, -N(R₇)-, ou, dans une orientation quelconque -SO₂N(R₇)- ou - C(=O)N(R₇)-, R₇ désignant un atome d'hydrogène ou un pont C₂-C₄ entre l'atome C ou N de X auquel il est rattaché et un atome de carbone de Alk² et Z désignant -CH₂, - C(=O) ou -S(=O)₂.