- 4-anilinoquinazoline derivative and albumin conjugates thereof
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a pharmaceutical composition for preventing, treating, or ameliorating one or more symptoms of a malignant tumor associated with EGFR mutation and/or K-RAS mutation is provided. The pharmaceutical composition includes a 4-anilinoquinazoline derivative having a formula (I) where A is iodine when m is 1 and n is zero, or A is albumin when m is an integral ranging from 1 to 7 and n is 1.
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- A method for preparing gefitinib, a tyrosine kinase inhibitor
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The invention discloses a method for preparing gefitinib that is a tyrosine kinase inhibitor, and belongs to the fields of medicines and fine chemical engineering. The method is a novel preparation scheme, and can prepare a target compound meeting requirements no matter from which intermediate. The method has advantages of short steps, simple reaction operation, high safety and reliability, a highyield, a low cost, high product purity, low pollution, simple operation, and the like.
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Paragraph 0085; 0086; 0087; 0088; 0089
(2018/03/26)
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- Synthesis and biological assay of erlotinib analogues and BSA-conjugated erlotinib analogue
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A series of erlotinib analogues that have structural modification at 6,7-alkoxyl positions is efficiently synthesized. The in vitro anti-tumor activity of synthesized compounds is studied in two non-small cell lung cancer (NSCLC) cell lines (A549 and H1975). Among the synthesized compounds, the iodo compound 6 (ETN-6) exhibits higher anti-cancer activity compared to erlotinib. An efficient method is developed for the conjugation of erlotinib analogue-4, alcohol compound, with protein, bovine serum albumin (BSA), via succinic acid linker. The in vitro anti-tumor activity of the protein attached erlotinib analogue, 8 (ETN-4-Suc-BSA), showed stronger inhibitory activity in both A549 and H1975 NSCLC cell lines.
- Boobalan, Ramalingam,Liu, Kuang-Kai,Chao, Jui-I.,Chen, Chinpiao
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p. 1784 - 1788
(2017/04/04)
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- PROCESS FOR PREPARING QUINAZOLINE DERIVATIVE
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A concise, efficient and cost-and time-saving process for the preparation of a quinazoline derivative of formula (A) given below: which is an intermediate for making gefitinib or gefitinib itself, comprising reacting a compound of formula (B): with 3-chloro-4-fluoroaniline (VI) in the presence of a N,N-dialkyl formamide acetal, a Bronsted acid catalyst, and a solvent in a one-pot reaction.
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Paragraph 0041
(2016/01/01)
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- Optimization of gefitinib analogues with potent anticancer activity
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The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.
- Yin, Kai-Hao,Hsieh, Yi-Han,Sulake, Rohidas S.,Wang, Su-Pei,Chao, Jui-I.,Chen, Chinpiao
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p. 5247 - 5250
(2015/01/08)
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- An efficient method for the preparation of nitriles via the dehydration of aldoximes with phthalic anhydride
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A new and highly efficient method for the conversion of aldoximes to nitriles was established. By fusing with phthalic anhydride, aldoximes were efficiently and smoothly converted into nitriles, in high yields (over 85%) and in a short time (within 5 minutes). The mixture of phthalic anhydride, a cyclic anhydride, and aldoximes in fusing state set up an ideal transition state for a selective [3.3]-sigmatropic rearrangement of the acylated aldoximes to nitriles.
- Wang, Eng-Chi,Huang, Keng-Shiang,Chen, Hsing-Ming,Wu, Chung-Chin,Lin, Gwo-Jiun
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p. 619 - 627
(2007/10/03)
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- Quinoline and quinazoline compounds useful in therapy
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Compounds of formula I, wherein R1 represents C1-4 alkoxy optionally substituted by one or more fluorine atoms; R2 represents an aryl group or a heteroaryl group, optionally substituted by C1-4 alkyl or SO2
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- Anthranilic acid derivatives as inhibitors of the cGMP-phosphodiesterase
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Compounds of formula (I) STR1where R 1 is hydrogen; R 2 is nitro, cyano or halo(lower)alkyl; R 3 is phenyl substituted with one or more substituents selected from halogen, cyano and lower alkoxy; A is a lower alkylene group; R 4 is a group CR 6 R 7 R 8 wherein R 6 and R 7 form, together with the carbon atom to which they are attached a cycloalkyl group optionally substituted with hydroxy, lower alkoxy or a lower alkanoylamino; and R 8 is hydrogen; its prodrug and a salt thereof.
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- Quinolines and quinazolines useful in therapy
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Compounds of formula I, wherein R1 represents C1-4 alkoxy optionally substituted by one or more fluorine atoms; R2 and R3 independently represent H or C1-6 alkoxy (which is optionally substituted); R4 represents a 4-, 5-, 6- or 7-membered heterocyclic rin
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- Quinoline and quinazoline compounds useful in therapy
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PCT No. PCT/EP96/05609 Sec. 371 Date Jun. 17, 1998 Sec. 102(e) Date Jun. 17, 1998 PCT Filed Dec. 5, 1996 PCT Pub. No. WO97/23462 PCT Pub. Date Jul. 3, 1997The invention provides compounds of formula (I), wherein R1 represents C1-4 alkoxy optionally substituted by one or more fluorine atoms; R2 represents H or C1-6 alkoxy optionally substituted by one or more fluorine atoms; R3 represents one or more groups independently selected from H, halogen, C1-4 alkoxy and CF3; in addition, R2 and one R3 group may together represent -OCH2-, the methylene group being attached to the ortho-position of the pendant phenyl ring; R4 represents a 4-, 5- or 6-membered heterocyclic ring containing 1 or 2 heteroatoms selected from N, O and S, the ring being optionally fused to a benzene ring or a 5- or 6-membered heterocyclic ring containing 1 or 2 heteroatoms selected from N, O and S, the ring system as a whole being optionally substituted; X represents CH or N; and L is absent or represents a cyclic group or an open chain group; and pharmaceutically acceptable salts thereof. The compounds of formula (I) are useful in the treatment of inter alia benign prostatic hyperplasia.
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- A new one pot method for the conversion of aldehydes into nitriles using hydroxyamine and phthalic anhydride
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The aryl and alkyl aldehydes were readily converted to give the corresponding nitrites in good yields using hydroxyamine and phthalic anhydride as reagents in one pot.
- Wang, Eng-Chi,Lin, Gow-Juin
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p. 4047 - 4050
(2007/10/03)
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- PHELLODENDRINE ANALOGS AND ALLERGY TYPE IV SUPPRESSOR CONTAINING THE SAME AS ACTIVE INGREDIENT
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Phellodendrine analogs represented by general formula (I), wherein A represents the group (a); B represents hydrogen, lower alkyl or lower acyl, or alternatively A and B together with the adjacent nitrogen atom form a substituted 1,2,3,4-tetrahydroisoquinoline ring represented by general formula (II), R11, R12, R21, R22, R31 and R32 represent each hydrogen, hydroxyl or lower alkoxy; n1 represents a number of 0 to 2; n2 represents a number of 1 and 2; and m1 represents a number of 0 to 1, provided tsat when A represents the group (b), and n2 is 2, B is lower acyl, and that when A and B together form a substituted 1,2,3,4-tetrahydroisoquinoline ring, n1 is 1 and m1 is not 0. These analogs (I) and related compounds have an excellent activity of suppressing allergy type IV and hence are utilizable as a medicine efficacious against diseases wherein allergy type IV participates, such as chronic hepatitis, intractable asthma, nephrotic syndrome or rheumatism.
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- Palladium-Catalyzed Decarbonylation of Acyl Cyanides
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The palladium-catalyzed decarbonylation of aromatic and heteroaromatic acyl cyanides 1 gives the corresponding nitriles 2 in excellent yields.Alkylacyl cyanides can be converted into the corresponding alkenes via decarbonylation followed by β-elimination of hydrogen cyanide.Because of easy preparation of acyl cyanides by the oxidation of cyanohydrins, the present decarbonylation reaction provides an efficient method for the preparation of nitriles from aldehydes under mild and neutral conditions.The catalytic decarbonylation involves the following processes; oxidative addition of acyl cyanides 1 to Pd(PPh3)4 to give acylpalladium complexes 13, acyl-aryl rearrangement, reductive elimination.When an acyl cyanide has a β-hydrogen, the intermediate cyanoalkylcarbonylpalladium (15) undergoes β-elimination to give alkenes.
- Murahashi, Shun-Ichi,Naota, Takeshi,Nakajima, Nobuyuki
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p. 898 - 901
(2007/10/02)
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