144
Views
4
CrossRef citations to date
0
Altmetric
Review

Inhibitory activities of bipyrazoles: a patent review

ORCID Icon, ORCID Icon & ORCID Icon
Pages 63-87 | Received 31 Mar 2021, Accepted 06 Jul 2021, Published online: 27 Jul 2021

References

  • Matsumoto H. New discoveries in agrochemicals, mode of action of pyrazole herbicides pyrazolate and pyrazoxyfen: HPPD inhibition by the common metabolite. ACS Symp Ser. 2004;892:161–171.
  • Khan MF, Alam MM, Verma G, et al. The therapeutic voyage of pyrazole and its analogs: a review. Eur J Med Chem. 2016;120:170–201.
  • Raffa D, Maggio B, Raimondi MV, et al. Recent advanced in bioactive systems containing pyrazole fused with a five membered heterocycle. Eur J Med Chem. 2015;97:732–746.
  • Faria JV, Vegi PF, Miguita AGC, et al. Recently reported biological activities of pyrazole compounds. Bioorg Med Chem. 2017;25(21):5891–5903. .
  • Abdel-Aziz HA, Mekawey AAI, Dawood KM, et al. Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur J Med Chem. 2009;44(9):3637–3644. .
  • Verma R, Verma SK, Rakesh KP, et al. Pyrazole-based analogs as potential antibacterial agents against methicillin-resistance staphylococcus aureus (MRSA) and its SAR elucidation. Eur J Med Chem. 2020;212:113134.
  • Dawood KM, Eldebss TM, El-Zahabi HS, et al. Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives. Eur J Med Chem. 2015;102:266–276.
  • Abdel-Gawad H, Mohamed HA, Dawood KM, et al. Synthesis and antiviral activity of new indole-based heterocycles. Chem Pharm Bull. 2010;58(11):1529–1531. .
  • Bennani FE, Doudach L, Cherrah Y, et al. Overview of recent developments of pyrazole derivatives as an anticancer agent in different cell line. Bioorg Chem. 2020;97:103470.
  • Dawood KM, Eldebss TM, El-Zahabi HS, et al. Synthesis of some new pyrazole-based 1, 3-thiazoles and 1,3,4-thiadiazoles as anticancer agents. Eur J Med Chem. 2013;70:740–749.
  • Dilek AM, Ozdemir A, Ilgın S, et al. Synthesis and biological evaluation of new pyrazole-based thiazolyl hydrazone derivatives as potential anticancer agents. Lett Drug Des Discov. 2014;11(7):833–839. .
  • Silva VLM, Elguero J, Silva AMS, et al. Current progress on antioxidants incorporating the pyrazole core. Eur J Med Chem. 2018;156:394–429.
  • Sharma V, Bhatia P, Alam O, et al. Recent advancement in the discovery and development of COX-2 inhibitors: insight into biological activities and SAR studies (2008–2019). Bioorg Chem. 2019;89:103007. . 2019.
  • Friedrich G, Rose T, Rissler K, et al. Determination of lonazolac and its hydroxyl and o-sulfated metabolites on-line sample preparation liquid chromatography with fluorescence detection. J Chromatogr B. 2002;786(2):295–305. .
  • Sebag, Pantel J, Williams SY, Mi D, et al. Development of a high throughput screen for allosteric modulators of melanocortin-4 receptor signaling using a real time cAMP assay. Eur J Pharmacol. 2011;660(1):139–147.
  • Hassan GS, Abou-Seri SM, Kamel G, et al. Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents. Eur J Med Chem. 2014;76:482–483.
  • Giorgi M, Mengozzi G, Rafaelli A, et al. Characterization of in vivo plasma metabolites of tepoxalin in horses using LC-MS-MS. J Pharm Anal Biomed Anal. 2011;56(1):45–53. .
  • Dowling G, Malone E. Analytical strategy for the confirmatory analysis of the non-steroidal anti-inflammatory drugs firocoxib, propyphenazone, ramifenazone and piroxicam in bovine plasma by liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal. 2011;56(2):359–365. .
  • Grover J, Kumar V, Sobhia ME, et al. Jachak, Synthesis, biological evaluation and docking analysis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones as potential cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med Chem Lett. 2014;24(19):4638–4642. .
  • Wyde PR, Gilbert BE, Ambrose MW, et al. Comparison of the antirespiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. Antiviral Res. 1989;11(1):15–26. .
  • Kapadia GJ, Tokuda H, Sridhar R, et al. Cancer chemopreventive activity of synthetic colorants used in foods, pharmaceuticals and cosmetic preparations. Cancer Lett. 1998;129(1):87–95. .
  • Kameyama T, Nabeshima T. Effects of 1,3-diphenyl-5-(2-dimethylaminopropionamide)-pyrazole[difenamizole] on a conditioned avoidance response. Neuropharmacology. 1978;17(4–5):249–256.
  • Song Z. In vitro detecting ultra-trace novalgin in medicine and human urine by chemiluminescence. Talanta. 2003;60(1):161–170.
  • TilakVijay J, Babu KV, Uma A, et al. Virtual screening of novel compounds as potential ER-alpha inhibitors. Bioinformation. 2019;15(5):321–332. .
  • Yoshida M, Nagamiya H, Ohba Y, et al. Heterocyclic compounds. PCT Int. Appl. WO 2014157569 A1. 2014..
  • Rostom SA. Polysubstituted pyrazoles, part 6. Synthesis of some 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazol-3-carbonyl derivatives linked to nitrogenous heterocyclic ring systems as potential antitumor agents. Med Chem. 2010;18:2767–2776.
  • Wang S, Yao H. Preparation of novel organic platinum complex and uses thereof. Faming Zh Shenq CN 101429218 A. 2009.
  • Yukimasa A, Kozono I, Nakamura K, et al. Preparation of heterocyclic compounds and their salts with TrkA inhibitory effect, and pharmaceutical compositions containing them. PCT Int. Appl. WO 2016021629 A1. 2016.
  • Pettinari C, Pettinari R, Xhaferai N, et al. Binuclear 3,3′,5,5′-tetramethyl-1H, H-4,4′-bipyrazole Ruthenium (II) complexes: synthesis, characterization and biological studies. Inorg Chim Acta. 2020;513:119902. 2020.
  • Kanthecha DN, Bhatt BS, Patel MN, et al. Bipyrazole based novel bimetallic µ-oxo bridged Au(III) complexes as potent DNA interacalative, genotoxic, anticancer, antibacterial and cytotoxic agents. J Inorg Organomet Polym Mater. 2020;30(12):5085–5099.
  • Zhang Q, Li H, Shao Y, et al. A new Cu(I)-based coordination polymer: crystal structure, molecular docking and protective effect in streptococcus-pneumoniae-infected mice by promoting immune cell response. ChemistrySelect. 2019;4(37):11019–11023.
  • Tabacaru A, Pettinari C, Marchetti F, et al. Antibacterial action of 4, 4′-bipyrazolyl-based silver (I) coordination polymers embedded in PE disks. Inorg Chem. 2012;51(18):9775–9788.
  • Dawood KM, Abbas AA. Synthetic routes to bioactive bipyrazole derivatives. ChemistrySelect. 2021;6(3):279–305.
  • Abdel-Wahab BF, Dawood KM. Synthesis and applications of bipyrazole systems. Arkivoc. 2012;1:491–545. DOI:https://doi.org/10.3998/ark.5550190.0013.112
  • Shkineva TK, Dalinger IL, Shevelev SA, et al. Synthesis of compounds with two or more pyrazole rings linked to each other. Chem Heterocycl Compds. 1995;31(5):509–529.
  • Dawood KM. Benzofuran derivatives; a patent review. Expert Opin Therap Pat. 2013;23(9):1133–1156.
  • Dawood KM, Farghaly TA. Thiadiazole inhibitors: a patent review. Expert Opin Therap Pat. 2017;27(4):477–505.
  • Behbehani H, Dawood KM, Farghaly TA, et al. Biological evaluation of benzosuberones. Expert Opin Therap Pat. 2018;28(1):5–29.
  • Dawood KM. An update on benzofuran inhibitors: a patent review. Expert Opin Therap Pat. 2019;29(11):841–870.
  • Dawood KM, Abbas AA. Inhibitory activities of indolizine derivatives: a patent review. Expert Opin Therap Pat. 2020;30(9):695–714.
  • Salameh BA, Abu-Safieh KA, AL-Aqrabawi IS, et al. Synthesis and cytotoxic activity of some new bipyrazole derivatives. Heterocycles. 2020;100(2):283–292.
  • Reddy KI, Aruna C, Manisha M, et al. Synthesis, DNA binding and in vitro cytotoxicity studies on novel bis-pyrazoles. J Photochem Photobiol B:. 2017;168:89–97.
  • Masaret GS. Synthesis, structure elucidation, and biological activities of pyrazoles against human lung and hepatocellular cancer. J Heterocycl Chem. 2018;55(9):2123–2129.
  • Nawaz F, Alam O, Perwez A, et al. 3′-(4-(Benzyloxy)phenyl)-1′-phenyl-5-(heteroaryl/aryl)-3,4-dihydro-1′H,2H-[3,4′-bipyrazole]-2-carboxamides as EGFR kinase inhibitors: synthesis, anticancer evaluation, and molecular docking studies. Arch Pharm. 2020;353(4):1900262.
  • Badr MH, Abd El Razik HA. 1,4-Disubstituted-5-hydroxy-3-methylpyrazoles and some derived ring systems as cytotoxic and DNA binding agents. Synthesis, in vitro biological evaluation and in silico ADME study. Med Chem Res. 2018;27(2):442–457.
  • Gul HI, Yamali C, Bulbuller M, et al. Anticancer effects of new dibenzenesulfonamides by inducing apoptosis and autophagy pathways and their carbonic anhydrase inhibitory effects on hCA I, hCA II, hCA IX, hCA XII isoenzymes. Bioorg Chem. 2018;78:290–297.
  • Gajera SB, Mehta JV, Thakor P, et al. Half-sandwich iridium III complexes with pyrazole-substituted heterocyclic frameworks and their biological applications. New J Chem. 2016;40(12):9968–9980. .
  • Gomha SM, Salah TA, Abdelhamid AO, et al. Synthesis, characterization, and pharmacological evaluation of some novel thiadiazoles and thiazoles incorporating pyrazole moiety as anticancer agents. Monatshefte für Chemie. 2015;146(1):149–158.
  • Ali YM, Ismail MF, Abu El-Azm FS, et al. Design, synthesis, and pharmacological assay of novel compounds based on pyridazine moiety as potential antitumor agents. J Heterocycl Chem. 2019;56:2580–2591.
  • Thakor KP, Lunagariya MV, Bhatt BS, et al. Bipyrazole-based palladium(II) complexes as DNA intercalator and artificial metallonuclease. Monatsh Chem. 2019;150(2):233–245.
  • Lunagariya MV, Thakor KP, Pursuwani BH, et al. Evolution of 1,3,5-trisubstituted bipyrazole scaffold based platinum (II) complexes as a biological active agent. Nucleosides, Nucleotides, Nucleic Acids. 2018;37(8):455–483.
  • Mor S, Mohil R, Nagoria S, et al. Synthesis and antimicrobial evaluation of some 1-(4-arylthiazol-2-yl)-1′-(aryl/heteroaryl)-3,3′-dimethyl-[4,5′-bi-1H-pyrazol]-5-ols. J Serbian Chem Soc. 2017;82(2):127–139.
  • Zala M, Vora JJ, Patel HB, et al. Synthesis, characterization, and comparative study of some heterocyclic compounds containing Isoniazid and Nicotinic Acid Hydrazide moieties. Russ J Org Chem. 2020;56(10):1795–1800.
  • Siddiqui ZN, Musthafa TM, Ahmad A, et al. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg Med Chem Lett. 2011;21(10):2860–2865.
  • Sahoo U, Dhanya B, Seth A, et al. Microwave assisted synthesis and characterization of certain novel bipyrazole derivatives and their antimicrobial activities. Int J Pharm Res. 2010;2:82–87.
  • Dhinoja V, Karia D, Shah A, et al. Acid promoted one pot synthesis of some new coumarinyl 3,4’-bipyrazole and their in vitro antimicrobial evaluation. Chem Biol Interface. 2014;4:232–245.
  • Siddiqui ZN, Praveen S, Musthafa MT, et al. Synthesis and antibacterial evaluation of novel heterocycles from 5-chloro-3-methyl-1-phenylpyrazole-4-carbaldehyde. Indian J Chem. 2011;50B:910–917.
  • Parshad M, Kumar D. Design, synthesis and characterization of isomeric 3,4’-bipyrazol-5’-ols and their antifungal activity. Chem Biol Interface. 2014;4:100–110.
  • Kalaria PN, Makawana JA, Satasia SP, et al. Design, synthesis and molecular docking of novel bipyrazolyl thiazolone scaffold as a new class of antibacterial agents. Med Chem Comm. 2014;5(10):1555–1562.
  • Ashok D, Ganesh A, Ravi S, et al., One pot multicomponent synthesis of 3′,5-diaryl-1′-phenyl-3,4-dihydro-1′H,2H-3,4′-bipyrazoles and their antimicrobial activity. Russ J Gen Chem. 2014;84(11): 2248–2256.
  • Singh KA, Sharma PK. Synthesis, characterization and antimicrobial study of some benzensulfonamide based bipirazols. Int J Pharm Pharm Sci. 2014;6:345–351.
  • Pundeer R, Kiran V, Sharma C, et al. Synthesis and evaluation of antibacterial and antifungal activities of new (Z)-3-bromo-4-(1,3-diaryl-1H-pyrazol-4-yl) but-3-en-2-ones and 4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1,3-diaryl-1H-pyrazoles. Med Chem Res. 2013;22(10):4715–4726.
  • Patel HB, Gohil JD, Patel MP, et al. Green approach for the facile construction of pyrazolylpyrazoline bearing benzothiazole derivatives and its biological evaluation. Heterocycl Lett. 2016;6:31–42.
  • Karad SC, Purohit VB, Raval DK, et al. Design, synthesis and characterization of fluoro substituted novel pyrazolylpyrazolines scaffold and their pharmacological screening. Eur J Med Chem. 2014;84:51–58.
  • Aggarwal R, Sumran G, Garg N, et al., Regioselective synthesis of some new pyrazol-1′-ylpyrazolo[1,5-a]pyrimidines in aqueous medium and their evaluation as antimicrobial agents. Eur J Med Chem. 2011;46(7): 3038–3046.
  • Taher AT, Sarg MT, Ali NR, et al. Design, synthesis, modeling studies and biological screening of novel pyrazole derivatives as potential analgesic and anti-inflammatory agents. Bioorg Chem. 2019;89:103023.
  • Veloso MP, Romeiro NC, Silva GM, et al. Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties. Chirality. 2012;24(6):463–470.
  • Faidallah HM, Rostom SA. Synthesis, anti-inflammatory activity, and COX-1/2 inhibition profile of some novel Non-Acidic Polysubstituted Pyrazoles and Pyrano[2,3-c]pyrazoles. Arch Pharm. 2017;350(5):1700025.
  • Faidallah HM, Rostom SA, Khan KA, et al. Synthesis and biological evaluation of pyrazole chalcones and derived bipyrazoles as anti-inflammatory and antioxidant agents. Arch Pharmacal Res. 2015;38(2):203–215.
  • Harras MF, Sabour R, Alkamali OM, et al., Discovery of new non-acidic lonazolac analogues with COX-2 selectivity as potent anti-inflammatory agents. Med Chem Comm. 2019;10(10): 1775–1788.
  • Ragab FA, Mohammed EI, Jaleel GA, et al., Synthesis of hydroxybenzofuranyl-pyrazolyl and hydroxyphenyl-pyrazolyl chalcones and their corresponding pyrazoline derivatives as COX inhibitors, anti-inflammatory and gastro-protective agents. Chem Pharm Bull. 2020;68(8): 742–752.
  • Kumar P, Chandak N, Kaushik P, et al. Benzenesulfonamide bearing pyrazolylpyrazolines: synthesis and evaluation as anti-inflammatory–antimicrobial agents. Med Chem Res. 2014;23(2):882–895.
  • Girisha KS, Kalluraya B, Rao P, et al. Synthesis, characterisation and pharmacological activities of 1-acetyl/propyl-3-aryl-5-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-pyrazolines. Der Pharm Chem. 2011;3:18–27.
  • Sharma PK, Kumar S, Kumar P, et al., Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory–antimicrobial agents. Eur J Med Chem. 2010;45(6): 2650–2655.
  • Raut DG, Lawand AS, Kadu VD, et al. Synthesis of asymmetric thiazolyl pyrazolines as a potential antioxidant and anti-inflammatory agents. Polycycl Aromat Comp. 2020. published online. DOI:https://doi.org/10.1080/10406638.2020.1716028.
  • Ali SA, Awad SM, Said AM, et al., Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors. J Enzyme Inhib Med Chem. 2020;35(1): 847–863.
  • Kamani KA, Patel KD. Synthesis, characterization and biological evaluation of coumarin-pyrazole-pyrazoline hybrids. World J Pharm Res. 2017;6:939–953.
  • Mogle PP, Meshram RJ, Hese SV, et al., Synthesis and molecular docking studies of a new series of bipyrazol-yl-thiazol-ylidene-hydrazinecarbothioamide derivatives as potential antitubercular agents. Med Chem Comm. 2016;7(7): 1405–1420.
  • Harikrishna N, Isloor AM, Ananda K, et al., Synthesis, and antitubercular and antimicrobial activity of 1′-(4-chlorophenyl) pyrazole containing 3,5-disubstituted pyrazoline derivatives. New J Chem. 2016;40(1): 73–76.
  • Neha S, Nitin K, Devender YM, et al. Synthesis of pyrazole derivatives: a new therapeutic approach for antitubercular and anticancer activity. J Pharm Res. 2013;12(1):5–14.
  • Tuha A, Bekhit AA, Seid Y, et al. Synthesis and biological screening of some thienyl and phenyl pyrazoline derivatives as antimalarial agent. Thai J Pharm Sci. 2014;38:121–129.
  • Thillainayagam M, Ramaiah S, Anbarasu A, et al., Molecular docking and dynamics studies on novel benzene sulfonamide substituted pyrazole-pyrazoline analogues as potent inhibitors of plasmodium falciparum histo aspartic protease. J Biomol Struct Dyn. 2020;38(11): 3235–3245.
  • Khloya P, Ceruso M, Ram S, et al., Sulfonamide bearing pyrazolylpyrazolines as potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem Lett. 2015;25(16): 3208–3212.
  • Assad A. Treatment of hematological malignancies using combination of a Janus kinase 1 (JAK1) inhibitor, an immunomodulatory agent and a steroid. U.S. Pat. Appl. Publ.
  • Allen S, Andrews SW, Baer B, et al. Preparation of 1-((3S,4R)-4-(3-fluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-yl)-3-(4-methyl-3-(2-methylpyrimidin-5-yl)-1-phenyl-1H-pyrazol-5-yl)urea as a TRKA kinase inhibitor. PCT Int. Appl.
  • Allen S, Andrews SW, Blake JF, et al. Pyrrolidinyl urea and pyrrolidinylthiourea compounds as trka kinase inhibitors. PCT Int. Appl.
  • Stachel S, Paone D, Li J, et al. Preparation of pyrazoles as cathepsin cysteine protease inhibitors. PCT Int. Appl.
  • Stachel S, Paone DV, Li J, et al. Preparation of pyrazoles as cathepsin cysteine protease inhibitors. PCT Int. Appl.
  • Andrews SW, Blake JF, Brandhuber BJ, et al. N-aryl-N’-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors and their preparation. PCT Int. Appl. WO 2014078325 A1. 2014.
  • Allen S, Andrews SW, Blake JF, et al. Preparation of bicyclic urea, thiourea, guanidine and cyanoguanidine compounds as TrkA inhibitors that are useful for the treatment of pain. PCT Int. Appl. WO 2014078454, A1. 2014.
  • Li YL, Zhuo J, Qian DQ, et al. Preparation of bipyrazole derivatives as JAK kinase inhibitors. PCT Int. Appl., WO 2014078454, A1. 2014.
  • Guo Y, Wang Z. Preparation of fused heterocyclic compounds as protein kinase inhibitors. PCT Int. Appl. WO 2014173289 A1. 2014.
  • Brandhuber BJ, Jiang Y, Kolakowski GR, et al. Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors and their preparation. PCT Int. Appl. WO 2014078417 A1. 2014.
  • Schultz-Fademrecht C, Klebl B, Choidas A, et al. Preparation of quinolinecarboxamide compounds as Axl inhibitors for treating hyperproliferative disorders. PCT Int. Appl. WO 2012028332 A1. 2012.
  • Andrews MD, Bagal SK, Gibson KR, et al. Pyrrolo[2,3-d]pyrimidine derivatives as inhibitors of tropomyosin-related kinases and their preparation and use in the treatment of pain. PCT Int. Appl. WO 2012137089 A1. 2012.
  • Gradl S, Rudolph J, Ren L, et al. Preparation of 1H-pyrazolo[1,5-a]pyrimidine compounds useful for inhibiting Raf kinase. PCT Int. Appl. WO 2011025951 A1. 2011.
  • Anderson KW, Fotouhi N, Gillespie P, et al. Preparation of pyrazole-4-carboxamide derivatives as 11-beta-hydroxysteroid dehydrogenase form I (11-beta-HSD1) inhibitors. PCT Int. Appl. WO 2007107470, A2. 2007.
  • Berdini V, O’Brien MA, Carr MG, et al. Preparation of pyrazole derivatives that modulate the activity of CDK, GSK and aurora kinases. PCT Int. Appl. WO 2006070198 A1.2006
  • Eckhardt M, Gollner A, Langkopf E, et al. Preparation of N-(1H,4H,5H,6H-cyclopenta[c]pyrazol-6-yl)heteroaromatic carboxamide derivatives as plasma kallikrein inhibitors. PCT Int. Appl. WO 2020035540 A1.2020
  • Gomha S, Abdalla M, Abd El-Aziz M, et al. Ecofriendly one-pot synthesis and antiviral evaluation of novel pyrazolylpyrazolines of medicinal interest. Turk J Chem. 2016;40:484–498.
  • Shigfuji T. Herbicide composition containing pyrazolylpyrazole compound and other herbicidally-active compound. Jpn. Kokai Tokkyo Koho, JP 2016141627 A.2016.
  • Matsubara K, Niino M. Preparation of pyrazolyl-pyrazole derivatives as herbicides. PCT Int. Appl.WO 2016117675 A1.2016
  • Matsubara T, Niino M. Substituted pyrazolylpyrazole derivative and its use as herbicide. PCT Int. Appl.WO 2015022924 A1.2015.
  • Bigot A, El Qacemi M. Preparation of aminocarbonylaryl-substituted (trifluoromethyl)-pyrazolyl sulfonates as agricultural pesticides. PCT Int. Appl. WO 2020127345 A1.2020
  • Harschneck T, Arlt A, Velten R, et al. Pyrazoles for controlling arthropods and their preparation. PCT Int. Appl. WO 2018177993 A1.2018
  • Ji W, Xu T, Wei Y, et al. Synthesis and insecticidal activity of a series of novel substituted bipyrazole compounds. Nongyaoxue Xuebao. 2011;13:121–126.
  • Hernandez AS, Ellsworth BA, Ewing WR, et al. Preparation of dihydropyrazole GPR40 modulators for treating diabetes and related conditions and other diseases. PCT Int. Appl. WO 2014078608 A1.2014.
  • Baker-Glenn C, Burdick DJ, Chambers M, et al. (Pyrazolylamino)pyrimidine derivatives as LRRK2 modulators and their preparation and use in the treatment of parkinson’s disease. PCT Int. Appl. WO. WO 2013164321 A1.2013
  • Kosley RW, MacDonald D, Sher R, et al. Preparation of dipyrazoles as central nervous system agents. PCT Int. Appl. WO 2006101903 A1.2006.
  • Wang S, Zhao Y, Zhou B, et al. 9H-Pyrimido[4,5-b]indoles as BET bromodomain inhibitors and their preparation. PCT Int. Appl. WO 2016138332 A1.2016.
  • Chau RW, Cullis CA, Duffey MO, et al. Preparation of heteroaryls as VPS34 and/or PI3K inhibitors. PCT Int. Appl. WO 2013096630 A1.2013.
  • Pennell AMK, Aggen JB, Wright JK, et al. Preparation of substituted piperazine derivatives as CCR1 receptor antagonists. U.S. Pat. Appl. Publ. US 20060106218 A1.2006.
  • Pennell AMK, Aggen JB, Wright JK, et al. Preparation of substituted piperazine derivatives as CCR1 receptor antagonists. PCT Int. Appl. WO 2005056015 A1.2005.
  • Chen X, Liu D, Zhou D, et al. Small-molecule CaV α1⋅CaV β antagonist suppresses neuronal voltage-gated calcium-channel trafficking. Proceed Nat Acad Sci. 2018;115(45):E10566–E10575.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.