307313-03-7|4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid| Ambeed

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Quality Control of [ 307313-03-7 ] Purity: 97% SDS Specification

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Product Details of [ 307313-03-7 ]

CAS No. :	307313-03-7
Formula :	C₈H₁₀N₂O₂
M.W :	166.18
SMILES Code :	OC(=O)C1=NN2CCCCC2=C1
MDL No. :	MFCD09056814
InChI Key :	GWQKXBKREDPLAS-UHFFFAOYSA-N
Pubchem ID :	21941460

Safety of [ 307313-03-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 307313-03-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	5
Fraction Csp3	0.5
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	42.91
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.05
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.92
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.67
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.82

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.62
Solubility	3.96 mg/ml ; 0.0238 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.55
Solubility	4.69 mg/ml ; 0.0282 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.89
Solubility	21.7 mg/ml ; 0.13 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.74 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.2

Application In Synthesis of [ 307313-03-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 307313-03-7 ]

[ 307313-03-7 ] Synthesis Path-Downstream 1~35

1
[ 307313-03-7 ]
3-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.6 g	With sulfuric acid; nitric acid; at 50 - 60℃; for 6h;	(ii) Fuming nitric acid (5 mL) was added to concentrated sulphuric acid (30 mL) with ice cooling. The resulting mixture was warmed to 40 C and the intermediate acid (5.0 g) was added portionwise over 1 h so as to keep the internal temperature between 50 and 60 C. The reaction was stirred at 60 C for 1 h followed by 4 h at 50 C. The mixture was allowed to cool to room temperature and stirred overnight. The mixture was poured onto ice and the resulting precipitate filtered off, washed with water, and dried to afford the acid intermediate, 3-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a] pyridine-2-carboxylic acid (4.6 g). 1H NMR (CDCl3) δ: 2.00 (m, 2H), 2.15 (m, 2H), 3.20 (t, 2H), 4.28 (t, 2H). LRMS (Thermospray) m/z: 229.3 (M+18)+.

References: [1]Patent: EP1241170,2002,A2 .Location in patent: Page column.
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

2
[ 307307-84-2 ]
[ 307313-03-7 ]

Yield	Reaction Conditions	Operation in experiment
84.8%	With water; sodium hydroxide; at 0 - 20℃; for 3.5h;	Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate (7.69 g, 39.6 mmol), H2O (60 mL)Add 250 mL round bottom flask, cool to 0 C, then add sodium hydroxide (7.90 g, 198 mmol) and continue to stir for 30 min.The reaction was further carried out for 3 h at room temperature, and the reaction of the starting material was completely confirmed by TLC.Add DCM (60 mL) to extract the liquid, and adjust the pH to 5 with concentrated hydrochloric acid.After standing, a yellow-white solid precipitated and was filtered.The yellow solid was 5.58g, and the yield was 84.8%.
		General procedure: (i) Sodium hydroxide solution (20 mL, 2 M, 40 mmol) was added to a solution of 23a (5.8 g, 30 mmol) in dioxan (100 mL), and the reaction stirred at room temperature for 18 h. The mixture was evaporated under reduced pressure and HCl (2 M, 21 mL) was added. The mixture was evaporated under reduced pressure, the residue azeotroped with toluene, and the product dried under vacuum.

References: [1]Patent: CN108948019,2018,A .Location in patent: Paragraph 0404; 0415; 0416.
[2]Patent: EP1241170,2002,A2 .Location in patent: Page 59.
[3]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.

3
[ 63237-88-7 ]
[ 307313-03-7 ]

References: [1]Patent: WO2006/15737,2006,A1 .Location in patent: Page/Page column 49.

4
[ 307313-03-7 ]
[ 307313-04-8 ]

References: [1]Patent: WO2006/15737,2006,A1 .Location in patent: Page/Page column 69-70.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4523 - 4527.
,.

5
[ 307313-03-7 ]
N-((1s,4s)-4-aminocyclohexyl)-2-(3'-(((3S,5R)-3,5-dimethylpiperazin-1-yl)methyl)-4'-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide [ No CAS ]
N-((1s,4s)-4-(2-(3'-(((3R,5S)-3,5-dimethylpiperazin-1-yl)methyl)-4'-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 101N-((ls,4s)-4-(2-(3'-(((3R,5S)-3,5-dimethylpiperazin-l-yl)methyl)-4'-hydroxybiphenyl-3- yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7-tetr ahy dr opyr azolo [ 1 ,5-a] pyridine-2- carboxamide EDCI (0.046 g, 0.24 mmol) was added to a solution of 4,5,6,7-tetrahydropyrazolo[l,5- a]pyridine-2-carboxylic acid (0.040 g, 0.24 mmol) and HOBt (0.037 g, 0.24 mmol) in DMF (2 mL) and stirred for 15 min. A solution of N-((ls,4s)-4-aminocyclohexyl)-2-(3'-(((3R,5S)-3,5- dimethylpiperazin-l-yl)methyl)-4'-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide (0.12 g, 0.22 mmol) and triethylamine (0.061 mL, 0.44 mmol) in DMF (2 mL) was added and the reaction stirred for a further 20 h. 7M NHs/MeOH (1 mL) added and stirred for 2 h. Acidified with 2M HCl and purified by reverse phase HPLC with aqTFA/MeCN as eluent to afford the title compound as a white solid. Yield: 143 mg1H NMR (400 MHz, DMSO) δ 8.33 (d, J = 7.2 Hz, IH), 8.25 (d, J = 3.4 Hz, IH), 8.05 (m, IH), 7.68 (m, IH), 7.58 (m, IH), 7.48 (m, 2H), 7.40 (m, IH), 7.27 (d, J = 8.1 Hz, IH), 7.14 (m, IH), 7.00 (d, J = 8.5 Hz, IH), 6.34 (s, IH), 4.18 (m, 2H), 4.01 (m, 4H), 3.84 (m, 2H), 3.62 - 3.45 (m, 5H), 2.89 - 2.76 (m, 2H), 2.74 (t, J = 7.1 Hz, 2H), 1.96 (m, 2H), 1.81 - 1.60 (m, 8H), 1.24 (d, J = 6.6 Hz, 6H). MS: APCI (+ve):696 (M+l)

References: [1]Patent: WO2009/144494,2009,A1 .Location in patent: Page/Page column 163.

6
[ 307313-03-7 ]
N-((1s,4s)-4-aminocyclohexyl)-2-(4'-(((3S,5R)-3,5-dimethylpiperazin-1-yl)methyl)-2'-(morpholinomethyl)biphenyl-3-yloxy)-5-fluoronicotinamide hydrochloride [ No CAS ]
N-((1s,4s)-4-(2-(4'-(((3S,5R)-3,5-dimethylpiperazin-1-yl)methyl)-2'-(morpholinomethyl)biphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 20h;	Example 124N-((ls,4s)-4-(2-(4'-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-2'- (morpholinomethyl)biphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7- tetrahydropyrazolo [ 1 ,5-a] pyridine-2-carboxamide HATU (0.113 g, 0.30 mmol) was added to a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(4'- (((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-2'-(morpholinomethyl)biphenyl-3-yloxy)-5- fluoronicotinamide (0.2 g, 0.27 mmol), 4,5,6, 7-tetrahydropyrazolo[l,5-a]pyridine-2- carboxylic acid (0.049 g, 0.30 mmol) and DIPEA (0.236 mL, 1.35 mmol) in DMF (5 mL) and the solution stirred at RT for 20 h. The mixture was purified by reverse phase HPLC with aqTFA/MeCN as eluant to afford the title compound as a white solid. Yield: 144 mg 1H NMR (400 MHz, CD3OD) δ 8.12 (d, J= 3.1 Hz, IH), 8.06 (m, IH), 8.03 (m, IH), 7.68 (m, IH), 7.60 (t, J= 7.8 Hz, IH), 7.46 (d, J= 8.0 Hz, IH), 7.33 (m, IH), 7.24 (d, J= 7.8 Hz, IH), 7.21 (m, IH), 6.41 (s, IH), 4.47 (s, 2H), 4.46 (s, 2H), 4.09 (t, J= 6.3 Hz, 2H), 3.97 (m, IH), 3.86 - 3.75 (m, 6H), 3.71 (m, 2H), 3.34 - 3.18 (m, 4H), 2.97 - 2.75 (m, 2H), 2.79 (t, J = 6.7 Hz, 2H), 2.03 (m, 2H), 1.91 - 1.67 (m, 12H), 1.40 (d, J= 6.4 Hz, 6H). MS: APCI (+ve):779 (M+l)

References: [1]Patent: WO2009/144494,2009,A1 .Location in patent: Page/Page column 201.

7
[ 307313-03-7 ]
N-((1s,4s)-4-aminocyclohexyl)-2-(4'-(2-((3S,5R)-3,5-dimethylpiperazin-1-yl)ethyl)biphenyl-3-yloxy)-5-fluoronicotinamide trihydrochloride [ No CAS ]
N-((1s,4s)-4-(2-(4'-(2-((3S,5R)-3,5-dimethylpiperazin-1-yl)ethyl)biphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; acetonitrile;	Step (d) N-((ls,4s)-4-(2-(4'-(2-((3S,5R)-3,5-Dimethylpiperazin-l-yl)ethyl)biphenyl-3- yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7-tetr ahy dr opyr azolo [ 1 ,5-a] pyridine-2- carboxamideTo a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(4'-(2-((3S,5R)-3,5-dimethylpiperazin-l- yl)ethyl)biphenyl-3-yloxy)-5-fluoronicotinamide, trihydrochloride (140 mg, 0.21 mmol) and 4,5,6,7-tetrahydropyrazolo[l,5-a]pyridine-2-carboxylic acid (35.5 mg, 0.21 mmol) in acetonitrile (2 mL) was added triethylamine (0.298 ml, 2.14 mmol). The mixture was allowed to stir until it became a solution. 1.57M solution of 1-propanephosphonic acid cyclic anhydride in THF (T3P) (0.667 ml, 1.05 mmol) was then added and the mixture allowed to stir for 2 hours. A further equivalent of both acid and T3P was added. The mixture was concentrated in vacuo and the residue partitioned between EtOAc and saturated NaHCC^aq). The EtOAc was evaporated and the residue purifed using reverse phase preparative chromatography (eluent = TFA(aq)/MeCN). The appropriate fractions were combined and evaporated to give a residue which was dissolved in water and lyophilised to give the title compound as a white solid. Yield: 38 mg1H NMR (400 MHz, CD3OD) δ 8.45 (d, J = 7.2 Hz, IH), 8.11 (d, J = 3.1 Hz, IH), 8.06 (dd, J = 8.0Hz, 3.1Hz, IH), 7.52 (d, J = 8.2Hz, 2H), 7.48 - 7.46 (m, 2H), 7.41 - 7.39 (m, IH), 7.27 (d, J = 8.2Hz, 2H), 7.18 - 7.12 (m, IH), 6.38 (s, IH), 4.11 (s, IH), 4.01 (t, J = 6.1Hz, 2H), 3.98 - 3.92 (m, IH), 3.48 - 3.34 (m, 4H), 2.92 (s, 4H), 2.77 (t, J = 6.4Hz, 2H), 2.36 (t, J = 12.1Hz, 2H), 2.04 - 1.96 (m, 2H), 1.87 - 1.78 (m, 8H), 1.73 - 1.65 (m, 2H), 1.32 (d, J = 6.5Hz, 6H). MS: [M+H]+=694 (calc=694) (MultiMode+)

References: [1]Patent: WO2009/144494,2009,A1 .Location in patent: Page/Page column 246.

8
[ 307313-03-7 ]
N-((1s,4s)-4-aminocyclohexyl)-2-(3'-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propyl)biphenyl-3-yloxy)-5-fluoronicotinamide hydrochloride [ No CAS ]
N-((1s,4s)-4-(2-(3'-(3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propyl)biphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 174N-((ls,4s)-4-(2-(3'-(3-((3S,5R)-3,5-Dimethylpiperazin-l-yl)propyl)biphenyl-3-yloxy)-5- fluoronicotinamido)cyclohexyl)-4,5,6,7-tetrahydr opyrazolo [ 1 ,5-a] pyridine-2- carboxamide To N-((ls,4s)-4-aminocyclohexyl)-2-(3'-(3-((3S,5R)-3,5-dimethylpiperazin-l- yl)propyl)biphenyl-3-yloxy)-5-fluoronicotinamide (0.1 g, 0.18 mmol) and 4,5,6,7- tetrahydropyrazolo[l,5-a]pyridine-2-carboxylic acid (0.033 g, 0.20 mmol) in acetonitrile (1 mL) was added triethylamine (0.249 mL, 1.79 mmol). The reaction was stirred for 10 minutes before 1-propanephosphonic acid cyclic anhydride, 1.57M solution in THF (T3P) (0.137 mL, 0.21 mmol) was added. The reaction was stirred at RT for 1 hour. The crude product was purified by preparative HPLC on a Phenomenex Gemini column using a 95-5% gradient of aqueous 0.1% TFA in methanol as eluent. The fractions containing the desired compound were freeze dried to afford the title compound as a white solid. Yield: 42 mg 1H NMR (SOO MHz, CD3OD) δ 8.14 - 8.06 (m, 2H), 7.53 - 7.42 (m, 6H), 7.32 (t, J= 9.6 Hz, IH), 7.22 - 7.15 (m, 2H), 6.36 (s, IH), 4.19 - 4.09 (m, IH), 4.03 - 3.90 (m, 3H), 3.87 - 3.67 <n="266"/>(m, 4H), 3.22 (t, J= 8.6 Hz, 2H), 3.06 (t, J= 12.0 Hz, 2H), 2.79 - 2.70 (m, 4H), 2.16 - 1.96 (m, 4H), 1.93 - 1.61 (m, 10H), 1.39 (d, J= 17.1 Hz, 6H). MS: [M+H]+=708 (calc=708) (MultiMode+)

References: [1]Patent: WO2009/144494,2009,A1 .Location in patent: Page/Page column 264-265.

10
[ 307313-03-7 ]
C₈H₈ClN₃O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

11
[ 307313-03-7 ]
3-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

12
[ 307313-03-7 ]
3-amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

13
[ 307313-03-7 ]
3-[({2-ethoxy-5-[(4-ethyl-1-piperazinyl) sulfonyl]-3-pyridinyl}carbonyl)amino]-4-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

14
[ 307313-03-7 ]
[ 459156-68-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

15
[ 307313-03-7 ]
2-{5-[(4-ethyl-1-piperazinyl)sulfonyl]-2-n-propoxy-3-pyridinyl}-7,8,9,10-tetrahydropyrido[2',1':5,1]pyrazolo[4,3-d]pyrimidin-4(3H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

16
[ 307313-03-7 ]
2-{5-[(4-ethyl-1-piperazinyl)sulfonyl]-2-(2-methoxyethoxy)-3-pyridinyl}-7,8,9,10-tetrahydropyrido[2',1':5,1]pyrazolo[4,3-d]pyrimidin-4(3H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.

17
[ 105786-95-6 ]
[ 307313-03-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 498 - 509.
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4523 - 4527.
,.
[4]Patent: CN108948019,2018,A .

18
[ 4043-87-2 ]
[ 307313-03-7 ]

19
[ 307313-03-7 ]
[ 364594-66-1 ]
[ 1367714-07-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.

20
[ 4515-18-8 ]
[ 307313-03-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.
[2]Patent: CN108948019,2018,A .

21
[ 307307-82-0 ]
[ 307313-03-7 ]