2-甲基-1,5-二苯基一吡咯甲酸 | 109812-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-甲基-1,5-二苯基一吡咯甲酸
• 中文别名: 1,5-二苯基-2-甲基吡咯-3-羧酸
• 英文名称: 2-methyl-1,5-diphenyl-pyrrole-3-carboxylic acid
• 英文别名: 2-Methyl-1,5-diphenyl-pyrrol-3-carbonsaeure；2-methyl-1,5-diphenyl-1H-pyrrole-3-carboxylic acid；2-methyl-1,5-diphenylpyrrole-3-carboxylic acid
• CAS: 109812-64-8
• 化学式: C₁₈H₁₅NO₂
• mdl: MFCD01567220
• 分子量: 277.323
• InChiKey: DWIYTBRYOQDHTE-UHFFFAOYSA-N

物化性质

• 熔点：
  226 °C
• 沸点：
  487.5±33.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.055
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

SDS

Name:	2-Methyl-1 5-diphenyl-1H-pyrrole-3-carboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	109812-64-8

Section 1 - Chemical Product MSDS Name:2-Methyl-1 5-diphenyl-1H-pyrrole-3-carboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
109812-64-8	2-Methyl-1,5-diphenyl-1H-pyrrole-3-car	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 109812-64-8: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 225 - 227 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C18H15NO2
Molecular Weight: 277

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, reducing agents, halogens, halogenated agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 109812-64-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Methyl-1,5-diphenyl-1H-pyrrole-3-carboxylic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 109812-64-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 109812-64-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 109812-64-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-甲基-1,5-二苯基一吡咯甲酸 在 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到4-Bromo-2-methyl-1,5-diphenylpyrrole-3-carboxylic acid
  参考文献：
  名称：

  Petruso, S.; Caronna, S.; Sferlazzo, M., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1277 - 1280

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-methyl-1,5-diphenyl-pyrrol-3-yl)-glyoxal 在 sodium hydroxide 、 乙醇 、 双氧水 作用下， 生成 2-甲基-1,5-二苯基一吡咯甲酸
  参考文献：
  名称：

  Sprio; Madonia, Gazzetta Chimica Italiana, 1957, vol. 87, p. 171,179

  摘要：

  DOI：

文献信息

• Inhibitors of P2X3
  申请人：Brotherton-Pleiss E. Christine

  公开号：US20070037974A1

  公开（公告）日：2007-02-15

  Compounds of formula 1 are modulators of P2X3 useful for the treatment of pain and genito-urinary, gastrointestinal, and respiratory disorders: wherein R 1 is —C(═S)CH 3 , pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, furyl, furylcarbonyl, acetyl, or carbamoyl; R 2a and R 2b are independently H, methyl, or ethyl; R 3 is H or methyl; Y is a bond, —(CR 4 R 5 ) n — or —CR 4 ═CR 5 —; wherein R 4 and R 5 are each independently H or methyl and n is 1 or 2; X is N or CH; A is phenyl, 5-membered heterocyclyl, or 6-membered heterocyclyl; R 6 , R 7 and R 8 are each independently H, halo, lower alkyl, cycloalkyl, alkylthio, alkylthio-lower alkyl, alkylsulfonyl-lower alkyl, di(lower alkyl)amino-lower alkyl, morpholinyl-lower alkyl, 4-methyl-piperazinyl-methyl, trifluoromethyl, pyridyl, tetrazolyl, thiophenyl, phenyl, biphenyl, or benzyl (where thiophenyl, phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoromethyl, lower alkoxy or lower alkylthio) or R 6 and R 7 together form a 5-membered or 6-membered carbocyclic or heterocyclic ring substituted with 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, oxo, halo, thiophenyl-lower alkyl, phenyl, benzyl (where phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoro-methyl, lower alkoxy, lower alkylthio, amino-lower alkyl, lower alkylamino-lower alkyl, or di(lower alkyl)amino-lower alkyl); and pharmaceutically acceptable salts thereof; wherein when R 1 is pyrimidin-2-yl, X is N, Y is a bond and A is oxazol-5-yl the carbon atom at position 4 in said oxazol-5-yl is not substituted by propyl when the carbon atom at position 2 in said oxazol-5-yl is substituted by substituted phenyl and the carbon atom at position 4 in said oxazol-5-yl is not substituted by phenyl when the carbon atom at position 2 is substituted by unsubstituted or substituted phenyl.

  式1的化合物是P2X3的调节剂，用于治疗疼痛和泌尿生殖、胃肠和呼吸系统疾病： 其中 R 1 为—C(═S)CH 3 ，吡啶基，嘧啶基，吡嗪基，噻唑基，呋喃基，呋喃甲酰基，乙酰基或氨基甲酰基；R 2a 和R 2b 独立地为H，甲基或乙基；R 3 为H或甲基；Y为键，—(CR 4 R 5 ) n —或—CR 4 ═CR 5 —；其中R 4 和R 5 各自独立地为H或甲基，n为1或2；X为N或CH；A为苯基，5-成员杂环基或6-成员杂环基；R 6 ，R 7 和R 8 各自独立地为H，卤素，低碳基，环烷基，烷基硫醚，烷基硫醚-低碳基，烷基磺酰基-低碳基，二(低碳基)氨基-低碳基，吗啉基-低碳基，4-甲基哌嗪基-甲基，三氟甲基，吡啶基，四唑基，噻吩基，苯基，联苯基或苄基（其中噻吩基，苯基和苄基被0-3个低碳基，卤素，磺酰胺基，三氟甲基，低烷氧基或低烷硫基取代）或R 6 和R 7 一起形成一个被0-3个取自由低碳基，低烷氧基，氧代基，卤素，噻吩基-低碳基，苯基，苄基（其中苯基和苄基被0-3个低碳基，卤素，磺酰胺基，三氟甲基，低烷氧基，低烷硫基，氨基-低碳基，烷基氨基-低碳基或二(低碳基)氨基-低碳基取代）的5-成员或6-成员碳环或杂环取代环；及其药学上可接受的盐；其中当R 1 为嘧啶-2-基时，X为N，Y为键，A为噁唑-5-基时，所述噁唑-5-基中位置4的碳原子在所述噁唑-5-基中位置2的碳原子被取代的苯基取代时不被丙基取代，且所述噁唑-5-基中位置4的碳原子在位置2被取代的苯基取代时不被苯基取代。
• [EN] 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE DERIVATIVES AND THEIR USE AS CANNABINOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE 1,5-DIARYL-PYRROLE-3-CARBOXAMIDE ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RECEPTEURS DES CANNABINOIDES
  申请人：ASTRAZENECA AB

  公开号：WO2004058249A1

  公开（公告）日：2004-07-15

  The present invention relates to a compound of formula (I) (A chemical formula should be inserted here - please see paper copy enclosed herewith) in which R1 and R2 independently represent phenyl, thienyl or pyridyl each of which is optionally substituted by one, two or three groups represented by Z; and R3 is H, a C1-3alkyl group, a C1-3alkoxymethyl group, trifluoromethyl, a hydroxyC1-3alkyl group, an aminoC1-3alkyl group, C1-3alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C1-3alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula -CONHNRaRb wherein Ra and Rb are as defined for R4 and R5 respectively; X is CO or SO2 ; Y is absent or represents NH optionally substituted by a C1-3alkyl group; R4 and R5 independently represent: a C1-6alkyl group; an (amino)C1-4alkyl- group in which the amino is optionally substituted by one or more C1-3alkyl groups; an optionally substituted non-aromatic C3-15carbocyclic group; a (C3-12cycloalkyl)C1-3alkyl- group; a group -(CH2)r(phenyl )s; naphthyl; anthracenyl; a saturated 5 to 8 membered heterocyclic group containing one nitrogen and optionally one of the following: oxygen, sulphur or an additional nitrogen wherein the heterocyclic group is optionally substituted ;1-adamantylmethyl; a group - (CH2)t Het where Het represents an aromatic heterocycle optionally substituted; or R4 represents H and R5 is as defined above; or R4 and R5 together with the nitrogen atom to which they are attached represent a saturated 5 to 8 membered heterocyclic group; R6 is H, a C1-3alkyl group, a C1-3alkoxymethyl group, trifluoromethyl, a hydroxyC1-3alkyl group, C1-3alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C1-3alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula -CONHNRaRb ; with provisos; to processes for preparing such compounds, to their use in the treatment of obesity, psychiatric and neurological disorders particularly obesity, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及一种化合物，其化学式为（I），其中R1和R2分别独立表示苯基，噻吩基或吡啶基，每个基上均可选择性地取代一个、两个或三个由Z表示的基团；R3为H，C1-3烷基基团，C1-3烷氧甲基基团，三氟甲基，羟基C1-3烷基基团，氨基C1-3烷基基团，C1-3烷氧羰基，羧基，氰基，氨基甲酰基，一级或二级C1-3烷基甲酰基，乙酰基或化学式为-CONHNRaRb的肼基，其中Ra和Rb分别定义为R4和R5；X为CO或SO2；Y为空或表示NH，该氮原子可选择性地取代为C1-3烷基基团；R4和R5独立地表示：C1-6烷基基团；（氨基）C1-4烷基基团，其中氨基可选择性地取代为一个或多个C1-3烷基基团；可选择性取代的非芳香性C3-15碳环基团；（C3-12环烷基）C1-3烷基基团；基团-(CH2)r(苯) s；萘基；蒽基；含有一个氮原子并可选择性地含有以下之一的饱和的5到8个成员的杂环基团：氧，硫或另一个氮原子，其中杂环基团可选择性地取代；1-金刚烷基甲基；基团-(CH2)t Het，其中Het表示可选择性取代的芳香性杂环族；或者R4表示H，R5如上所定义；或者R4和R5与它们连接的氮原子一起表示饱和的5到8个成员的杂环基团；R6为H，C1-3烷基基团，C1-3烷氧甲基基团，三氟甲基，羟基C1-3烷基基团，C1-3烷氧羰基，羧基，氰基，氨基甲酰基，一级或二级C1-3烷基甲酰基，乙酰基或化学式为-CONHNRaRb的肼基；但需注意的是，本发明还涉及制备这种化合物的方法，以及它们在肥胖、精神和神经疾病特别是肥胖的治疗中的应用方法和包含它们的制药组合物。
• [EN] AQUEOUS DISPERSION COMPRISING STABLE NANOPARTICLES OF A WATER-INSOLUBLE PYRROLE CARBOXAMIDE AND EXCIPIENT LIKE MIDDLE CHAIN TRIGLYCERIDES<br/>[FR] DISPERSION AQUEUSE COMPRENANT DES NANOPARTICULES STABLES DE CARBOXAMIDE DE PYRROLE INSOLUBLE DANS L'EAU ET DES TRIGLYCERIDES A CHAINE MOYENNE DU TYPE EXCIPIENT
  申请人：ASTRAZENECA AB

  公开号：WO2004069227A1

  公开（公告）日：2004-08-19

  A process for the preparation of a stable dispersion of solid particles, in an aqueous medium comprising combining (a) a first solution comprising a substantially water-insoluble substance which is a pyrrole carboxamide compound of Formula I, a water-miscible organic solvent and an inhibitor with (b) an aqueous phase comprising water and optionally a stabiliser, thereby precipitating solid particles comprising the inhibitor and the substantially water-insoluble substance; and optionally removing the water-miscible organic solvent; wherein the inhibitor is a non-polymeric hydrophobic organic compound as defined in the description. Also claimed are stable dispersions obtainable by the process, solid particles obtainable by the process and use of such particles. The process provides a dispersion of solid particles in an aqueous medium, which particles exhibit reduced or substantially no particle growth mediated by Ostwald ripening. The process is particlularly suitable for the preparation of small (sub-micron) aqueous dispersions of a substantially water-insoluble pharmacologically active substance.

  一种制备固体颗粒在水性介质中的稳定分散体的方法，包括将（a）包含化学式I的一种基本不溶于水的物质、易溶于水的有机溶剂和抑制剂的第一溶液与（b）包含水和可选稳定剂的水相结合，从而沉淀出包含抑制剂和基本不溶于水的物质的固体颗粒；并可选择性地去除易溶于水的有机溶剂；其中抑制剂是根据说明中定义的非聚合疏水有机化合物。还声明了通过该方法获得的稳定分散体、通过该方法获得的固体颗粒以及使用这种颗粒。该方法提供了固体颗粒在水性介质中的分散体，这些颗粒表现出由奥斯瓦尔德成核引起的减少或基本无颗粒生长。该方法特别适用于制备基本不溶于水的药理活性物质的小（亚微米）水性分散体。
• 1,5-Diaryl-pyrrole-3-carboxamide derivatives and their use as cannabinoid receptor modulators
  申请人：Berggren Ingrid Kristina Anna

  公开号：US20060122230A1

  公开（公告）日：2006-06-08

  The present invention relates to a compound of formula (I) in which R 1 and R 2 independently represent phenyl, thienyl or pyridyl each of which is optionally substituted by one, two or three groups represented by Z; and R 3 is H, a C 1-3 alkyl group, a C 1-3 alkoxymethyl group, trifluoromethyl, a hydroxyC 1-3 alkyl group, an aminoC 1-3 alkyl group, C 1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C 1-3 alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula —CONHNR a R b wherein R a and R b are as defined for R 4 and R 5 respectively; X is CO or SO 2 ; Y is absent or represents NH optionally substituted by a C 1-3 alkyl group; R 4 and R 5 independently represent: a C 1-6 alkyl group; an (amino)C 1-4 alkyl-group in which the amino is optionally substituted by one or more C 1-3 alkyl groups; an optionally substituted non-aromatic C 3-15 carbocyclic group; a (C 3-12 cycloalkyl)C 1-3 alkyl-group; a group —(CH 2 ) r (phenyl) s ; naphthyl; anthracenyl; a saturated 5 to 8 membered heterocyclic group containing one nitrogen and optionally one of the following: oxygen, sulphur or an additional nitrogen wherein the heterocyclic group is optionally substituted; 1-adamantylmethyl; a group —(CH 2 ) t Het where Het represents an aromatic heterocycle optionally substituted; or R 4 represents H and R 5 is as defined above; or R 4 and R 5 together with the nitrogen atom to which they are attached represent a saturated 5 to 8 membered heterocyclic group; R 6 is H, a C 1-3 alkyl group, a C 1-3 alkoxymethyl group, trifluoromethyl, a hydroxyC 1-3 alkyl group, C 1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C 1-3 alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula —CONHNR a R b ; with provisos; to processes for preparing such compounds, to their use in the treatment of obesity, psychiatric and neurological disorders particularly obesity, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及一种化合物，其化学式为（I），其中R1和R2分别独立表示苯基，噻吩基或吡啶基，每个基团可选地被Z所代表的一个、两个或三个基团取代；而R3则表示H、C1-3烷基、C1-3烷氧甲基、三氟甲基、羟基C1-3烷基、氨基C1-3烷基、C1-3烷氧羰基、羧基、氰基、氨基甲酰基、一级或二级C1-3烷基甲酰基或肼基羰基，其中Ra和Rb分别如同R4和R5所定义；X为CO或SO2；Y为不存在或代表可选地被C1-3烷基取代的NH；而R4和R5独立地表示：C1-6烷基、（氨基）C1-4烷基，其中氨基可选地被一个或多个C1-3烷基取代，可选地被取代的非芳香性C3-15碳环基，（C3-12环烷基）C1-3烷基，基团—（CH2）r（苯基）s，萘基，蒽基，含有一个氮原子且可选地含有以下一种:氧、硫或另一个氮原子的饱和的5到8个成员杂环基，其中该杂环基可选地被取代；1-金刚烷甲基，基团—（CH2）tHet，其中Het代表可选地被取代的芳香性杂环；或者R4表示H，而R5如同上述所定义；或者R4和R5与它们所连接的氮原子一起表示一个饱和的5到8个成员杂环基；而R6表示H、C1-3烷基、C1-3烷氧甲基、三氟甲基、羟基C1-3烷基、C1-3烷氧羰基、羧基、氰基、氨基甲酰基、一级或二级C1-3烷基甲酰基或肼基羰基，其中Ra和Rb分别如同上述所定义；但需注意以下情况：本发明还涉及制备此类化合物的方法，以及将其用于治疗肥胖症、精神和神经疾病，特别是肥胖症的方法和含有它们的制药组合物。
• Preparation and use of pyrrole derivatives for treating obesity
  申请人：——

  公开号：US20040267028A1

  公开（公告）日：2004-12-30

  This invention relates to pyrrole derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders. 1

  本发明涉及吡咯衍生物，已被发现可抑制食欲并导致减重。本发明还提供了合成该化合物的方法，包括该化合物的药物组成物，以及使用这种组成物诱导减重和治疗肥胖和与肥胖有关的疾病的方法。