- Synthesis process of alogliptin benzoate
-
The invention discloses a synthesis process of alogliptin benzoate. The synthesis process comprises the following steps: 1, preparing an initial raw material 6-chlorouracil; 2, preparing 2-((6-chlorine-2, 4-dioxo-3, 4-dihydro-2H-pyrimidine-1-radical)methyl)cyanophenyl; 3, preparing 2-[(6-chlorine-3, 4-dihydro-3-methyl-2, 4-dioxo-1(2H)-pyrimidinyl)methyl]benzonitrile; 4, preparing alogliptin; 5, preparing alogliptin benzoate. According to the invention, the alogliptin benzoate is synthesized by taking cheap and easily available 6-chlorouracil, alpha bromo-o-methylbenzonitrile and (R)-3-aminopiperidine as raw materials through reactions such as alkylation, methylation, affinity substitution, salification and the like; according to the synthetic route, raw materials are cheap and easy to obtain, the synthetic cost is reduced, all steps are classic reactions, and synthesis improvement is easy; the improved process is low in raw material cost, simple to operate, mild in reaction condition,simple in post-treatment and suitable for industrial production.
- -
-
Paragraph 0007; 0092; 0121-0144
(2021/02/10)
-
- Preparation method of alogliptin benzoate intermediate and preparation method of alogliptin benzoate
-
The invention provides a reparation method of an alogliptin benzoate intermediate and a preparation method of alogliptin benzoate. The yield of the alogliptin benzoate intermediate prepared by the method is not lower than 88%, and the purity is not lower than 99.5%; and according to the alogliptin benzoate raw material medicine prepared by the method, D90 does not exceed 220 microns, and preferably does not exceed 200 microns. All indexes of the prepared pharmaceutical composition meet medicinal requirements, the quality is stable in the storage process, and the clinical curative effect and medication safety can be guaranteed.
- -
-
Paragraph 0074-0079; 0092-0095
(2021/08/28)
-
- 3, 4-dihydropyrimidine benzonitrile derivative as well as preparation method and application thereof
-
The invention provides a 3, 4-dihydropyrimidine benzonitrile derivative as well as a preparation method and application thereof. The invention discloses a structure of a specific impurity (RRT is an impurity of 1.22) generated in the process of preparing alogliptin benzoate by adopting the route of the original research patent for the first time. The series of impurities have a warning structure,and the content of the impurities in the alogliptin benzoate finished product needs to be detected according to related limits of the genetically toxic impurities. The invention further provides a preparation and purification method of the high-purity compound shown in the formula (A) and a detection method of the content of the impurity compound in the alogliptin benzoate medicine, and thereforequality control over the alogliptin benzoate medicine is achieved.
- -
-
Paragraph 0026-0027; 0065
(2021/03/13)
-
- Preparation method of alogliptin benzoate
-
The invention discloses a preparation method of alogliptin benzoate. Main starting materials of the preparation method are 6-chloro-3-methyluracil, o-cyanobenzyl bromide, (R)-3-Boc-aminopiperidine andbenzoic acid. According to the method, all indexes meet the specification, meanwhile, dangerous reagents such as sodium hydride and highly toxic methyl iodide are prevented from being used in the reaction process, the requirement for the operation process is not strict, and water-free and oxygen-free conditions are not needed; a high-boiling-point mixed solvent is not used in the reaction, and the solvent is easy to recycle; the selected starting materials are available in the market and easy to obtain, and large-scale production is facilitated; in addition, starting materials or intermediates in the synthetic route are good in stability and convenient to store and control, and genotoxic impurities are avoided in the reaction process; and the synthesis process is environment-friendly.
- -
-
Paragraph 0028-0029; 0033-0034
(2021/01/29)
-
- Novel preparation process of alogliptin benzoate
-
The invention discloses a novel preparation process of alogliptin benzoate. The method comprises the steps: reacting 3-methyl-6-chlorouracil serving as an initial raw material with 2-cyanobenzyl bromide under an alkaline condition by taking toluene as a solvent to obtain 2-[(6-chloro-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl)methyl]benzonitrile, then reacting the solvent system with (R)-3-Boc-aminopiperidine under an alkaline condition, dissociating a protecting group by using acid to obtain alogliptin, and carrying out salifying reaction on the alogliptin and benzoic acid to finally prepare the alogliptin benzoate which is an anti-type 2 diabetes medicine. The preparation method adopts a one-pot method, has the advantages of low raw material cost, high yield, reduction of post-treatment operation of each chemical reaction in multi-step reaction, great shortening of the production period, few impurities generated in the reaction, high product quality, relative reduction of the use amount of chemical reagents, relatively environmental protection and the like, and is beneficial to industrial production.
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-
Paragraph 0027; 0038-0040; 0047-0048; 0049-0050; 0051-0052
(2021/05/08)
-
- Refining method of alogliptin benzoate
-
The invention discloses a refining method of alogliptin benzoate, which is characterized in that an alogliptin benzoate crude product (the purity is 99.73%) is used as a starting raw material, the alogliptin benzoate crude product is dissolved by adding an organic solvent, and is cooled to crystallize to obtain a high-purity target product alogliptin benzoate solid, and the purity of the alogliptin benzoate solid can reach 99.99% through HPLC detection. Compared with the prior art, the toxicity of the used solvent is low, the mother liquor solvent can be recycled, and the environmental pollution is small; and the operation is simple and feasible, and industrial large-scale production is facilitated.
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-
Paragraph 0116-0118
(2021/06/06)
-
- Industrial production method of Alogliptin benzoate
-
The invention relates to an industrial production method of Alogliptin benzoate, and belongs to the technical field of industrial pharmacy. The method comprises three steps of 1, preparing an Alogliptin intermediate AG I; 2, preparing an Alogliptin intermediate AG II; 3, preparing the Alogliptin benzoate. The industrial production method has the beneficial effects that the reaction conditions areproper; the operation is simple and convenient; the realization is easy; only the Alogliptin intermediate AG II is prepared; then, the AG II and benzoic acid are subjected to tetrahydrofuran synthesis; the Alogliptin benzoate can be obtained; the process is saved; the cost is reduced; used solvents have small environment pollution; the operation is safe; under the large-scale industrial productioncondition, the existing average yield is only about 30 percent; under the condition that the final yield reaches 19.32kg, the finial product yield reaches 94.77 percent; the total yield reaches 60.11percent; high quality and purity can be maintained; the production efficiency is greatly improved.
- -
-
Paragraph 0049-0066; 0106-0120; 0155-0169
(2019/02/04)
-
- Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes
-
A mild and highly efficient catalytic amination procedure for chloroheteroarenes at ambient temperature using the Pd/PTABS catalytic system is reported. The protocol is selective for the amination of chloroheteroarenes using secondary amines such as piperidine, pyrrolidine, and several others. The exceptional mildness of the developed protocol is beneficial for the synthesis of a crucial Buparlisib intermediate as well as the formal synthesis of Alogliptin in competitive yields.
- Murthy Bandaru, Siva Sankar,Bhilare, Shatrughn,Chrysochos, Nicolas,Gayakhe, Vijay,Trentin, Ivan,Schulzke, Carola,Kapdi, Anant R.
-
supporting information
p. 473 - 476
(2018/01/28)
-
- Preparation method of alogliptin benzoate
-
The invention discloses a preparation method of alogliptin benzoate. The preparation method of alogliptin benzoate comprises the following steps of, firstly, reacting 3-methyl-6-chlorouracil with 2-cyanobenzyl bromide to obtain 2-(6-chloro-3-methyl-2, 4-dioxo-3, 4-dihydro-2H-pyrimidine-1-methyl)-benzonitrile; secondly, reacting 2-(6-chloro-3-methyl-2, 4-dioxo-3, 4-dihydro-2H-pyrimidine-1-methyl)-benzonitrile with (R)-3-aminoperidine dihydrochloride to obtain alogliptin; thirdly, salifying alogliptin with benzoic acid to obtain alogliptin benzoate. According to the preparation method of alogliptin benzoate, condensation reaction in the first step is implemented in dichloromethane solvent and under reflux conditions, thereby being mild in conditions and capable of achieving a yield higher than 90%; condensation reaction in the second step is implement in water or water-methylbenzene mixed solution to avoid production of disubstituted impurities and achieving high product purity.
- -
-
Paragraph 0042; 0043; 0051
(2018/05/16)
-
- Preparation method of alogliptin benzoate impurity
-
The invention relates to a preparation method of alogliptin benzoate impurity and belongs to the technical field of pharmaceutical chemicals. The preparation method of alogliptin benzoate impurity provided by the invention comprises the following steps: (1) preparing TM1 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)cyanophenyl by taking 6-chloro-3-methylpyrimidin-2,4(1H,3H)-diketone as a raw material which reacts with 2-bromomethyl cyanophenyl; (2) preparing alogliptin benzoate impurity BP1 through a reaction between the TM1 and monohydric alcohol in an alkaline condition, wherein the structural formula of the BP1 is shown in the description. The preparation method provided by the invention is convenient to operate, the reaction conditions are mild and controllable,the side reactions are reduced, and therefore, the target product alogliptin benzoate is easy to separate and purify and has high purity.
- -
-
Paragraph 027; 0028
(2018/04/01)
-
- A preparing method for alogliptin benzoate
-
The invention provides a preparing method for alogliptin benzoate, and particularly provides a method for preparing 2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]methyl]benzonitrile monobenzoate shown as a formula (I). The compound is a novel medicine treating diabetes mellitus type 2. The alogliptin benzoate (HPLC purity of which is greater than 99.95%) can be prepared in a high yield and high purity by the method, a process is simple and convenient to operate and the method is suitable for industrial production.
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-
Paragraph 0039; 0059; 0060; 0062; 0063; 0064; 0078; 0080
(2018/04/01)
-
- DPP-4 inhibitor with dual action mechanisms and application of DPP-4 inhibitor
-
The invention discloses a DPP-4 inhibitor with dual action mechanisms and application of the DPP-4 inhibitor, relates to the field of dipeptidyl peptidase IV inhibitor medicines and in particular relates to a DPP-4 inhibitor, a preparation method of a compound of formula I and medicinal application of the compound as a novel DPP-4 inhibitor, and particularly application of the inhibitor in preparing anti-diabetic medicines. In-vivo and in-vitro pharmacodynamic experiment results show that the compound of formula I has a remarkable inhibition function on DPP-4, has an excellent blood sugar reduction effect, and in addition has a relatively good action effect when being compared with similar medicines alogliptin and vildagliptin. Meanwhile, the compound disclosed by the invention is simple and short in preparation route, easy in raw material obtaining, simple in process, applicable to industrial large-scale production and very great in development prospect.
- -
-
Paragraph 0033-0035
(2018/10/19)
-
- Preparation process of alogliptin benzoate
-
The invention discloses a preparation process of alogliptin benzoate, wherein the preparation process comprises the steps: carrying out nucleophilic substitution of 3-methyl-6-chlorouracil and 2-cyanobromobenzyl under alkaline conditions to obtain 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl methyl)-benzonitrile (a compound 1); then substituting with (R)-3-aminoperidol dihydrochloride to obtain (R)-2-[(6-(3-aminoperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]benzonitrile (a compound 2); and finally, salifying with benzoic acid to obtain alogliptin benzoate (a compound 3), determining the structure of the target compound at each step by MS and 1H-NMR, and determining the purity by HPLC. The method has the advantages of easy availability of raw materials, mild reaction conditions and simple operation, can be used for production in large quantities to meet the needs of use, is a high-efficiency green environmental-protection process and is suitable for industrialized production.
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-
Paragraph 0019; 0020; 0025; 0026
(2019/01/06)
-
- Preparation method of dipeptidyl peptidase IV inhibitor
-
The invention provides a preparation method of a dipeptidyl peptidase IV inhibitor. The preparation method utilizes isopropanol and water as solvents and a volume ratio of isopropanol to water is 1-8: 1 so that a product yield and product purity are greatly improved and reaction time is shortened. An intermediate is subjected to beating and purification under action a poor solvent. The purification method is simple in operation, a product yield and product purity are high, and the production process is easy to control and is suitable for industrial production.
- -
-
Paragraph 0025; 0028
(2017/08/28)
-
- Preparation and after-treatment method for high-purity alogliptin benzoate
-
The invention relates to optimization and improvement of a preparation and after-treatment method for alogliptin benzoate. In the Boc deprotection process, alkali extraction and acid precipitation methods are adopted, and impurities which do not contain basic groups are effectively removed on the basis of simplifying the process. Moreover, the solvent and temperature control is optimized in the salifying process, and the product quality and yield are improved.
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-
Paragraph 0012; 0022
(2017/08/29)
-
- PROCESS FOR THE PREPARATION OF ALOGLIPTIN
-
The invention concerns a process for the preparation of 2-[[6-[(3R) -3-amino-l-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-l(2H)- pyrimidinyl]methyl]benzonitrile commonly known as alogliptin and its pharmaceutically acceptable benzoate salt. Alogliptin is a dipeptidyl peptidase-4 inhibitor (DPP-4) that is designed to slow the inactivation of incretin hormones glucagon-like peptide-1 (GLP-1) and glucose- dependent insulinotropic peptide (GIP). It is used as antidiabetic drug. Formula (I)
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-
Page/Page column 13; 14
(2016/11/21)
-
- A new method for preparing argues a row sandbank benzoic acid
-
The invention discloses a novel method for preparing alogliptin benzoate ((R)2-[6-[3(R)-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)methyl]benzonitrile benzoate). The method comprises the steps of alkylation, phase transfer catalysis reaction, catalytic hydrogenation, salt formation protection and the like. The process is novel in routes, short in the steps, high in reaction yield, and low in production costs; the method has larger implementing value and social economic benefit.
- -
-
Paragraph 0034; 0038; 0039
(2016/12/01)
-
- A preparing process of alogliptin benzoate
-
The invention relates to a preparing process of alogliptin benzoate that is a medicine for treating diabetes mellitus type 2. The process includes reacting 6-chloro-3-methyluracil which is adopted as a raw material and 2-cyanobenzyl bromide to obtain 2-[(6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)methyl]benzonitrile, performing a substitution reaction with (R)-3-Boc-aminopiperdine, removing Boc after the reaction is finished to obtain alogliptin, and salting with benzoic acid to obtain the alogliptin benzoate. The process is characterized in that: in the substitution reaction, an acid-binding agent which is potassium carbonate is added, and water is added after the reaction is finished to allow the protected alogliptin to precipitate so as to obtain the alogliptin with Boc protection; and in the deprotection and salting reaction, the alogliptin with Boc protection is deprotected in an ethanol solution of thionyl chloride, and the benzoic acid is added into an ethyl acetate solution of the alogliptin, refluxed and salted to obtain the alogliptin benzoate.
- -
-
Paragraph 0013
(2016/10/08)
-
- A method for refining argues a row sandbank benzoic acid
-
The invention discloses a method for refining alogliptin benzoate. The method for refining the alogliptin benzoate comprises that 6-chloro-3-methyl uracil and 2-cyano benzyl bromide are taken as initial raw materials, a two-step amination reaction and a one-step salt forming reaction are sequentially carried out, so that an alogliptin benzoate crude product is obtained, and then the obtained alogliptin benzoate crude product is crystallized in methyl alcohol in presence of benzoic acid, so that the alogliptin benzoate refined product is obtained. The method for refining the alogliptin benzoate has the advantages that yield and purity of alogliptin benzoate can be effectively improved, operation is simple and cost is low.
- -
-
Paragraph 0014; 0038-0039
(2017/01/17)
-
- argues a row sandbank a method for synthesis of benzoic acid
-
The invention discloses a synthesis method of alogliptin benzoate. The synthesis method comprises the following steps: putting 2-cyano benzyl bromide, 3-3metyl-6-chlorouracil and tri-n-butylamine in methylbenzene and stirring for reaction; cooling, adding water and stirring for crystallization; filtering and washing with water to obtain 2-(6-chlorine-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimdine-1-metyl)-benzonitrile; adding 2-(6-chlorine-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimdine-1-metyl)-benzonitrile, (R)-3-piperidinamine dihydrochloride and alkali into ethyl alcohol and stirring for reaction; purifying and salifying with benzoic acid to obtain alogliptin benzoate. The synthesis method disclosed by the invention is mild in condition, easy to control, non-toxic, environment-friendly, high in purity and high in yield.
- -
-
Paragraph 0053-0055
(2017/05/04)
-
- argues a row sandbank a process for the preparation of benzoic acid
-
The invention discloses a preparation method of alogliptin benzoate shown in a formula 1 in the specification for treating type 2 diabetes mellitus. The preparation method has the advantages that raw materials are easy to obtain, reaction conditions are mild and the operation is simple and convenient, and is suitable for large-scale industrial production.
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-
Paragraph 0015-0017
(2017/02/09)
-
- A NOVEL PROCESS FOR PREPARATION OF ALOGLIPTIN BENZOATE
-
The present invention provides a novel process for preparing Alogliptin free base and its benzoate salt which comprises insitu condensation process to produce protected Alogliptin by reacting 6-chloro-3-methylpyrimidine-2, 4(1H, 3H)-dione with 2-(halo methyl) benzonitirle in presence of a base, aprotic solvent followed by insitu reaction with protected (3R)-piperidin-3-amine at elevated temperature. The protected Alogliptinis deprotected to obtain Alogliptin free base and further converted to Alogliptin benzoate.
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-
-
- LAMINATED TABLET AND MANUFACTURING METHOD THEREFOR
-
According to the present invention, a multilayer tablet showing suppressed layer separation and a production method thereof are provided. A concave portion having a depth of not less than 0.1 mm Ka is formed on at least one surface Sa of the both front and back surfaces (Sa, Sb) of a multilayer tablet. Particularly, a multilayer structure obtained by, in tableting, forming a convex portion for forming the concave portion on at least the upper punch, and preliminarily compressing all layers in the multilayer tablet with the upper punch to form a concave portion having the same shape with a depth of not less than 0.1 mm on the upper surface of all layers, wherein the powder materials of the next layer are protruding into the concave portion, is a preferable embodiment.
- -
-
Paragraph 0109-0112
(2014/01/18)
-
- Discovery of highly potent DPP-4 inhibitors by hybrid compound design based on linagliptin and alogliptin
-
Highly potent DPP-4 inhibitors have been identified by hybrid compound design based on linagliptin and alogliptin. The most promising compound 2h (IC50 = 0.31 nM) exhibited 8.5-fold and 2.5-fold more potent activity than that of alogliptin (IC50 = 2.63 nM) and linagliptin (IC 50 = 0.77 nM), respectively. Compound 2h had a good inhibition selectivity for DPP-4 over DPP-8/9 and thus was selected for further biological evaluation, including oral glucose tolerance, plasma DPP-4 inhibitory activity, pharmacokinetic profile, acute toxicity and hERG inhibition. The assay results showed that 2h displayed significant in vivo glucose-lowering effect and low risk of toxicity. Further studies are expected to confirm 2h as a potential drug candidate for the treatment of type 2 diabetes.
- Lai, Zeng-Wei,Li, Chunhong,Liu, Jun,Kong, Lingyi,Wen, Xiaoan,Sun, Hongbin
-
p. 547 - 560
(2014/07/21)
-
- NOVEL SALTS OF ALOGLIPTIN
-
The present invention provides a novel process for the preparation of amorphous alogliptin benzoate. The present invention also provides amorphous alogliptin benzoate co-precipitated on copovidone, process for its preparation and pharmaceutical compositions comprising it. The present invention further provides novel salts of alogliptin, processes for their preparation and pharmaceutical compositions comprising them. The present invention further provides crystalline hydrochloride salt of alogliptin, process for its preparation and pharmaceutical compositions comprising it. The present invention further provides crystalline tartrate salt of alogliptin, process for its preparation and pharmaceutical compositions comprising it.
- -
-
-
- Design and synthesis of pyrimidinone and pyrimidinedione inhibitors of dipeptidyl peptidase IV
-
The discovery of two classes of heterocyclic dipeptidyl peptidase IV (DPP-4) inhibitors, pyrimidinones and pyrimidinediones, is described. After a single oral dose, these potent, selective, and noncovalent inhibitors provide sustained reduction of plasma DPP-4 activity and lowering of blood glucose in animal models of diabetes. Compounds 13a, 27b, and 27j were selected for development.
- Zhang, Zhiyuan,Wallace, Michael B.,Feng, Jun,Stafford, Jeffrey A.,Skene, Robert J.,Shi, Lihong,Lee, Bumsup,Aertgeerts, Kathleen,Jennings, Andy,Xu, Rongda,Kassel, Daniel B.,Kaldor, Stephen W.,Navre, Marc,Webb, David R.,Gwaltney, Stephen L.
-
p. 510 - 524
(2011/03/20)
-
- Synthesis of a novel analogue of DPP-4 inhibitor Alogliptin: Introduction of a spirocyclic moiety on the piperidine ring
-
We report the synthesis of a novel analogue of Alogliptin via condensation of two key intermediates one of which is an aminopiperidine derivative bearing a spirocyclic ring on the piperidine moiety. Preparation of the aminopiperidine intermediate was carried out by constructing the cyclopropyl ring prior to assembling the piperidine ring.
- Kodimuthali, Arumugam,Pal, Manojit,Prasunamba, Padala Lakshmi
-
supporting information; experimental part
(2010/11/21)
-
- PROCESS FOR THE PREPARATION OF ALOGLIPTIN
-
The present invention is based on the discovery of a process for preparing pyrimidin- dione compounds, especially alogliptin and its derivatives, which comprises the reaction of a urea derivative of formula (VIII) with a malonic acid or its derivatives to form intermediates of formulae (VII) or (VII-A), which are subsequently converted to a compound of formula (II) upon introduction of a leaving group X. Compound (II) then reacts with an amine to form compound (I), which is optionally converted to its salts of formula (IV).
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Page/Page column 25-26
(2010/11/05)
-
- DIPEPTIDYL PEPTIDASE INHIBITORS
-
Methods of making compounds of the formula (I) wherein the variables are as defined herein. Also, methods of making compounds that may be used to inhibit dipeptidyl peptidase.
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-
Page/Page column 23
(2009/12/02)
-
- POLYMORPHS OF BENZOATE SALT OF 2-[[6-[(3R)-3-AMINO-1-PIPERIDINYL]-3,4-DIHYDRO-3-METHYL-2,4-DIOXO-1(2H)-PYRIMIDINYL]METHYL]-BENZONITRILE AND METHODS OF USE THEREFOR
-
Compositions comprising Compound I, wherein the Compound I is present in one or more polymorphic forms. Also provided are kits and articles of manufacture with compositions comprising one or more polymorphs of Compound I, and methods of using the compositions to treat various diseases.
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Page/Page column 13-14; 14
(2008/06/13)
-
- Discovery of alogliptin: A potent, selective, bioavailable, and efficacious inhibitor of dipeptidyl peptidase IV
-
Alogliptin is a potent, selective inhibitor of the serine protease dipeptidyl peptidase IV (DPP-4). Herein, we describe the structure-based design and optimization of alogliptin and related quinazolinone-based DPP-4 inhibitors. Following an oral dose, these noncovalent inhibitors provide sustained reduction of plasma DPP-4 activity and a lowering of blood glucose in animal models of diabetes. Alogliptin is currently undergoing phase 111 trials in patients with type 2 diabetes.
- Feng, Jun,Zhang, Zhiyuan,Wallace, Michael B.,Stafford, Jeffrey A.,Kaldor, Stephen W.,Kassel, Daniel B.,Navre, Marc,Shi, Lihong,Skene, Robert J.,Asakawa, Tomoko,Takeuchi, Koji,Xu, Rongda,Webb, David R.,Gwaltney II, Stephen L.
-
p. 2297 - 2300
(2008/02/05)
-
- Dipeptidyl peptidase inhibitors
-
Compounds, pharmaceuticals, kits and methods are provided for use with DPP-IV and other S9 proteases that comprise a compound comprising Formula I: wherein M is N or CR4; Q1 and Q2 are each independently selected from the group consisting of CO, SO, SO2, and C=NR9; and each R1, R2, R3, R4 and R9 are as defined herein.
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Page/Page column 43-44
(2008/06/13)
-
