A	B	C	D	E	F	G	H	I	J	K	L	M	N	O	P	Q	R	S	T	U	V
1	Main
2		Patent
3		8791110	4-methyl-piperazine-1-carbothioic acid amide derivatives and analogs for treatment of Arenaviruses
4			Tacaribe, Machupo, Pichinde, VSV viruses
5
6						EC50s (µM) vs. pseudotypes				Structure
7			Compound			Tacaribe	Machupo	Pichinde	VSV
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9			N-(3,4- dichlorophenyl)piperidine-			0.109	0.28	0.98	>25
10			1-carbothioamide
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15			N-(3,4- dichlorophenyl)morpholine-			0.178	0.48	1.02	>25
16			4-carbothioamide
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21		8754082	benzimidazole derivatives and analogs for treatment of Arenaviruses
22			Lassa virus
23			A 7-azabenzimidazole core (Compound 1) is shown to be very potent with EC50 0.13 nM in the assay against Lassa GP-pseudotyped-virus in 293T cells
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25										EC50s (µM) vs. pseudotypes
26			Compound					Formula		Machupo	Guanarito	Junin	Sabia	VSVg		Analytical data						Structure
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28			[3-(4-Ethoxy-phenyl)- 3H-imidazo[4,5- b]pyridin-6-yl]-					C23 H24 N4 O		< 0.05 uM	< 0.05 uM	< 0.05 uM	< 0.05 uM	1 < EC50 <		H NMR in CDCl3: δ 8.11 (s, 1H), 7.97 (d, 1H), 7.59 (t, 1H),
29			(4- ethyl-benzyl)-amine											50 uM		7.56 (t, 1H), 7.34 (s, 1H), 7.32 (d, 2H), 7.19 (d, 2H),
30																7.06 (t, 1H), 7.03 (t, 1H), 4.36 (s, 2H), 4.12 (br, 1H),
31																4.09 (q, 2H), 2.64 (q, 2H), 1.45 (t, 3H), 1.23 (t, 3H);
32																Mass Spec: 373.2 (M + H)+
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34
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36		8664274	sulfonyl semicarbazides, carbonyl semicarbazides semicarbazides, and ureas for treatment of Arenaviruses
37		ST-336	Tacaribe, Machupo, Guanarito, and Junin viruses
38		ST-294	Among the 36 quality hits, there were several clusters of structure type - ST-336 was chosen for further development and is the representative prototype for this series
39
40			Specificity of ST-336			Inhibitory
41			for Tacaribe			Concentration (EC)		Value (μM)
42			(CPE)			EC50		0.055
43			(CPE)			EC90		0.125
44			(Virus yield)			EC90		0.068
45			(Virus yield)			EC99		0.085
46			(Plaque reduction)			EC50		0.1
47			Candid1 (CPE)			EC50		0.062
48			Amapari (CPE)			EC50		>20
49			Machupo (Plaque reduction)			EC50		0.15
50			Guanarito (Plaque reduction)			EC50		0.3
51			Junin (Plaque reduction)			EC50		0.15
52			Lassa (plaque reduction)			EC50		>20
53			LCMV (Elisa)			EC50		>20
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55			ST-336 showed no inhibitory activity against LCM virus or authentic Lassa virus and lacked activity against the Amapari virus
56			ST-336 showed potent antiviral activity against the vaccine strain of Junin virus (Candid 1) as well as Machupo, Guanarito, and Junin
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58						Inhibitory
59			Selectivity of ST-336			Concentration (EC)		Value (μM)
60			HSV-1 (CPE)			EC50		>20
61			CMV (Elisa)			EC50		>20
62			Vaccinia (CPE)			EC50		>20
63			RSV-A (CPE)			EC50		>20
64			Rotavirus (CPE)			EC50		>20
65			SARS (CPE)			EC50		>20
66			Ebola (CPE)			EC50		>20
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68			ST-336 exerted its inhibitory effect only at the very early stage in the virus life cycle - addition of ST-336 at any time post-infection had no effect on virus yield, suggesting its an early stage inhibitor of virus replication
69			Data suggested that ST-336 binds intact virions with a very slow dissociation constant
70			Growth of ST-336 isolates was unaffected by the presence of ST-336 at concentrations that completely inhibited wild type Tacaribe virus replication, strongly suggesting that ST-336 acts as a direct antiviral inhibitor
71			Data suggest that amino acid changes in arenavirus GP2 at either position 416, 418, 433 or 436 are sufficient to confer reduced susceptibility to ST-336
72			ST-336 had poor pharmacokinetic (PK) properties in rodents, and the optimization program to improve the PK properties resulted in ST-294 - similar activity against Tacaribe, Machupo, Guanarito, and Junin viruses
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74			Specificity of ST-294			Inhibitory
75			for Tacaribe			Concentration (EC)		Value (μM)
76			(CPE)			EC50		0.12
77			(Plaque reduction)			EC90		0.1
78			Machupo (Plaque reduction)			EC90		0.3
79			Guanarito (Plaque reduction)			EC99		1
80			Junin (Plaque reduction)			EC50		0.3
81
82			Properties
83			Solubility (0%, 2%, 10% FBS)					18, 21 and 23 µM
84			Solubility (pIon, pH 7.4)					480 µM
85			Stability (S9) rat/mouse/human/g.p					26/74/100/23 min
86			Genotoxicity (Ames test)					negative
87			1/2 Life (PK rat/oral)					2 hours
88			Bioavailability (PK rat/oral)					0.682
89			1/2 Life (PK newborn mouse)					3 hours
90			Cmax (PK newborn mouse)					2910 ng/ml
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92			To test tolerability, newborn mice were given IP dosages ranging from 0-100 mg/kg/day of ST-294 for 5 days
93			Dosages of 100 mg/kg/day for 5 days were well tolerated - no clinical signs of toxicity, mice gained weight
94			The drug levels and half-life shown in the PK study was not equivalent to that seen in the rats, but serum levels sufficient to perform proof-of-concept animal study
95			Four day old mice were challenged with 30×LD50 of Tacaribe virus and treated with placebo, ribavirin as a control or ST-294
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97			ST-294 showed efficacy, with both survival and a delay in death similar to the drug control (ribavirin)
98			Promising results to advance into definitive animal studies - guinea pigs and primates
99			In mouse model the mice appear to die of a neurological disease (indicated by hindquarter paralysis) and it is not known whether ST-294 can cross the blood brain barrier
100			Drug levels and half-life of this drug candidate given IP in newborn mice is not as good as oral dosing in rats
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122		8658697	sulfonyl semicarbazides, carbonyl semicarbazides, and ureas for treatment of Arenaviruses
123		ST-336	2A: Vero cells were infected with Tacaribe virus at a MOI=0.01, ST-336 was added prior to or during Tacaribe infection (−1, 3, 6, 9, 12, 15, 18 or 21 hours post-infection). At 24 hours post-infection, virus yields were determined by plaque assay
124		ST-294	2B: Vero cells were infected with 400 pfu Tacaribe virus, ST-336 was added for 1 hour before the infection
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144			3A: Virus dilution scheme prior to plating is provided - the virus mixed with ST-336 and diluted (left side) or virus diluted and ST-336 added after dilution (right side)
145			3B: Pictures of the plaques that resulted after plating each dilution - shows that ST-336 binds with slow Koff to intact Tacaribe virion in the absence of cells
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167			4A: Linear map of the glycoprotein precursor showing the location of the signal peptide, transmembrane domain, the cleavage site between GP1 and GP2 (K261-A262), the location of the four ST-336 resistant mutants (“DR #1-4”), and the amino acid change for each
168			4B: Amino acid sequence alignment (SEQ ID NOS 3-16, respectively, in order of appearance) of GP2 from wild type NWA and ST 336 DRVs is shown
169			Shown is the amino acid sequence of the C-terminal portion of GP2 (amino acids 397 to 457) containing the transmembrane domain (marked by vertical lines), the location of the mutations for DR#1-4 (underlined), and the amino acid difference in Amapari (in bold).
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191			The ST-336 class of compounds targets the GP2 envelope protein, with mutations eliciting reduced susceptibility to the drug arising in or around the transmembrane region
192			Drugs that target the interactions between the virus envelope and the cellular receptor represent a new class of antiviral drugs - entry inhibitors have raised interest because of their activity against multi-drug resistant viruses
193			ST-294 also has the potential for prophylactic use since this drug appears to bind to the virus and would prevent infection - other virus entry inhibitors have demonstrated protection when given prophylactically
194
195		8629170	benzimidazole derivatives and analogs for treatment of Arenaviruses
196		ST-600037	Lassa, Guanarito, Tacaribe viruses
197		ST-600193	Compound ST-600037 was identified as one of the most potent and selective compounds from within the pool of 25 quality hits
198			ST-600193 displayed enhanced potency and selectivity relative to ST-600037
199			ST-600193 is also a potent inhibitor of pseudotyped viral infection mediated by the envelopes of the New World arenaviruses Guanarito (EC50<1 nM) and Tacaribe (EC50=4 nM) - could be used for other viruses besides Lassa fever
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201				Activity against Lassa							CC50/EC50
202				GP-pseudotyped-virus			Activity vs. LFV				(Therapeutic
203			No.	EC50 (µM)			Specificity		EC50 (µM)		Index)	formula			structure/name
204
205			600037	0.016			900		<0.1		>400	C22H21N3O2
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213			600193	0.0011			13000		<0.1		>400	C24H25N3O
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227		8623347	2,2′-bibenzimidazole, 2,2′-bibenzoxazole and 2,2′-bibenzothiazole derivatives and analogs for treatment of Arenaviruses
228			lymphocytic choriomeningitis virus (LCMV)
229			In LCMV-infected cells in the presence of 10 μM compound, synthesis of viral S RNA and NP mRNA were dramatically suppressed relative to untreated controls for a period of at least 48 h post infection
230			No CAT activity was observed in infected cells treated with 20 µM of Compound 1 - suggests that Compound 1 inhibits the activity of either viral NP or L protein, preventing efficient transcription and translation of viral RNA
231			Compounds 6 and 7 displayed enhanced potency (EC50=6 nM and 63 nM, respectively) and selectivity relative to Compound 1
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233				Analytical
234			No.	Data				Activity		chemical name			formula		structure/name
235
236			6	1H NMR in DMSO-d6: d 14.04 (br s, 2H),				EC50 < 1 uM		4,4'-Difluoro-1H,1'H- [2,2']			C14 H8 F2 N4
237				12.02 (br s, 1H), 7.26-7.45 (m, 4H),						bibenzoimidazolyl
238				7.07- 7.17 (m, 2H); Mass Spec: 269.3 (M - H)-
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241			7	1H NMR in DMSO-d6: d 7.76-7.82 (m, 1H),				EC50 < 1 uM		5,5'-Difluoro-1H,1'H- [2,2']			C14 H8 F2 N4
242				7.54-7.68 (m, 2H), 7.12-7.34 (m, 3H);						bibenzoimidazolyl
243				Mass Spec: 269.3 (M - H)-
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246			1	1H NMR in DMSO-d6: d 13.55 (s, 2H),				EC50 < 1 uM		1H, 1'H- [2,2']
247				7.76 (d, 2H), 7.56 (d, 2H), 7.29 (td, 4H);						bibenzoimidazolyl			C14 H10 N4
248				13C NMR in DMSO-d6: d 143.81, 143.49,
249				134.83, 123.63, 122.25, 119.18, 112.06;
250				HRMS: 234.08976 M+
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252		8518951	4-methyl-piperazine-1-carbothioic acid amide derivatives and analogs for treatment of Arenaviruses
253			Machupo, Guanarito viruses
254			No.	EC50/CC50 μM Tacaribe			EC50/CC50 μM Candid 1			EC50 μM Category A NWA					structure/name
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256			313761	0.14 / 50			0.26 / 50			Machupo: 0.3; Guanarito: 0.15
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266			280611	0.06 / 25			0.05 / 25			Not tested
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278			20013	>50 / >50			>50 / >50			Not tested
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287		8492434	cycloalkanecarboxylic acid hydrazide derivatives and analogs for treatment of Arenaviruses
288		ST-408306	Guanarito, Tacaribe viruses
289		ST-600161	Compound 408306 was identified as one of the most potent and selective compounds from within the pool of 25 quality hits
290			ST-600161 is also a potent inhibitor of pseudotyped viral infection mediated by the envelopes of the New World arenaviruses Guanarito (EC50=0.3 µM) and Tacaribe (EC50=0.8 µM)
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292				Activity against Lassa							CC50/EC50
293				GP-pseudotyped-virus			Activity vs. LFV				(Therapeutic
294			No.	EC50 (µM)			Specificity		EC50 (µM)		Index)	formula			structure/name
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296			408306	0.02			>2000		0.5		>100	C18H19N3O
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301			600161	0.0005			>90,000		<0.02		<2000	C23H21N3O3
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313		8461177	benzimidazole derivatives and analogs for treatment of Arenaviruses
314			arenaviruses
315			Compound 1 is shown to be very potent with EC50 0.13 nM in the assay against Lassa GP-pseudotyped-virus in 293T cells
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317				Analytical
318			No.	Data				chemical name			formula		structure/name
319
320			1	1H NMR in CDCl3: d 8.11 (s, 1H), 7.97				[3-(4-Ethoxy-phenyl)-			C23 H24 N4 O
321				(d, 1H), 7.59 (t, 1H), 7.56 (t, 1H), 7.34				3H-imidazo[4,5- b]pyridin-6-yl]-
322				(s, 1H), 7.32 (d, 2H), 7.19 (d, 2H), 7.06				(4-ethyl- benzyl)-amine
323				(t, 1H), 7.03 (t, 1H), 4.36 (s, 2H), 4.12
324				(br, 1H), 4.09 (q, 2H), 2.64 (q, 2H), 1.45
325				(t, 3H), 1.23 (t, 3H);
326				Mass Spec: 373.2 (M +H)+
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330						Activity (EC50s in µM vs. pseudotyped virus)
331			Compound			Lassa		Machupo		Guanarito		Junin		Sabia		VSVg
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333			1			EC50 < 0.05 uM		EC50 < 0.05 uM		EC50 < 0.05 uM		EC50 < 0.05 uM		EC50 < 0.05 uM		1 < EC50 < 50 uM
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335		8410149	sulfonyl semicarbazides, semicarbazides and ureas derivatives and analogs for treatment of Arenaviruses
336		ST-294	arenaviruses
337		ST-193	7: Shows chemical structures of fusion inhibitors
338		ST-761	ST-294 and ST-193 - genetic studies of GPC from the Junin virus (JUNV) suggest that these small-molecule inhibitors bind to and stabilize the prefusion GPC complex, thereby preventing pH-induced activation of membrane fusion and virus entry
339		ST-161	ST-294 and ST-761 are specific to the NW arenaviruses
340		TSRI 17C8	ST-193 and TSRI 17C8 inhibit both NW and OW viruses
341		TSRI 8C1	ST-161 and TSRI 8C1 are selective for the OW LASV
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363			8: Shows immunoprecipitation of insect and mammalian-cell derived cleavage-defective GPC
364			Four MAbs (BE08, AG02, BF11, and AA09) have shown to be capable of neutralizing viral infectivity and would serve as sensitive probes for the native GPC conformation
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392			9: Shows biosensor analysis (Biacore T100) of the interaction of small-molecule fusion inhibitors with detergent solubilized icd-GPC
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419			10: Shows inhibition of pH-induced cell-cell fusion
420			ST-375 is a dansyl analogue of ST-294 that inhibits JUNV GPC-mediated cell-cell fusion at an EC50 similar to that of its parent (0.6 and 1.5 µM for ST-375 and ST-294)
421			Each line denotes fusion inhibition by a small molecule as indicated by the symbols: ST-294 (filled squares), ST-761 (open squares), ST-193 (open circles), ST-375 (closed circles), and 17C8 (open diamonds)
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444			11: Shows competitive binding of small-molecule fusion inhibitors to icd-GPC
445			Determined that bound ST-375 was displaced from icd-GPC in a time- and concentration-dependent manner by ST-294 as well as by ST-761 and ST-193, but not by ST-161
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466			ST-294, has been identified to potently and selectively inhibit NWA viruses in vitro including the 3 NIAID/CDC Category A viruses (Junin, Machupo, and Guanarito viruses)
467			Also evaluated for stability in S9 liver extracts and for it's pharmacokinetic properties and was found to be metabolically stable and orally bioavailable
468			Preliminary study showed significant protection against Tacaribe virus induced disease in newborn mice - apparent that this series of compounds targets GP2 and are viral entry inhibitors
469			Apparent that the drug binds to virus and is carried over during dilutions (could potentially have an effect when titrating virus samples during other experiments, but wasn't enough drug carry over to affect the titers due to high dilution)
470			Since ST-294 has better S9 stability than ST-336 does, thought that metabolism occurs at the methyl group on the aromatic ring
471			The benzylic position is susceptible to oxidation - when there is no benzylic hydrogen present as in ST-294, oxidation is blocked and thus eliminates the fastest metabolism pathway
472			Addition of the difluoromethoxy group in ST-294 gave this compound increased S9 stability, but did not reduce antiviral activity
473			Not known whether ST-294 can cross the blood brain barrier (mice appear to die of a neurological disease, indicated by hind quarter paralysis)
474			Drug levels and half-life in newborn mice is not as good as oral dosing in rats - guinea pigs and non-human primates more appropriate (virus replication in spleen, lymph nodes and bone marrow)
475			Also has the potential for prophylactic use since this drug appears to bind to the virus
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477		7977365	benzimidazole derivatives and analogs for treatment of Arenaviruses
478		ST-193	Lassa virus
479		ST-600037	1A: Benzimidazole derivative ST-37 (left) was modified to generate ST-193 (right)
480		ST-600193	1B: Inhibition of LASV GP- or VSVg-pseudotyped HIV infection with ST-37 or ST-193
481			Infectivity measured by luciferase reporter relative to controls with no compound -each point is an average of three replicates, with error bars designating standard deviation
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508			2A: Schematic representation of LASV-LCMV chimeric GPs - predicted TMD and heptad repeat domains (HR1 and HR2) are indicated
509			2B: Pseudotype infectivity as in FIG. 1 using the arenavirus GPs shown (representative experiment)
510			Average IC50s±SEM for these constructs were: LASV, 0.0016±0.0003 μM; LCMV, 31±4 μM; LASVN-LCMVC, 13.6±2.2 μM; and LCMVN-LASVC, 0.0005±0.0003 μM
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532			3A: Schematic representation of an arenavirus GP2 subunit and the sites of 193R variations
533			The TCRV amino acid sequence is shown for the region indicated, with sites identified as determinants of ST-193 sensitivity indicated with raised letters and numbering (TCRV GP amino acid numbering)
534			Predicted TMD and heptad repeat domains (HR1 and HR2) are indicated (TMD is outlined in the sequence)
535			3B: Single amino acid variations that reduce ST-193 sensitivity in TCRV GP
536			Resistance is the fold change in IC50 as measured with TCRV GP-pseudotyped HIV, relative to wild-type, and averaged across at least four independent experiments (each in triplicate)
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559			4: Residues identified as ST-193 sensitivity determinants (FIG. 3) are in bold type, and the predicted TMD is indicated
560			The highlighted residues at positions 421 and 425 are sensitivity determinants for which some sequence divergence is observed across the Arenaviridae family
561			LASV, Lassa fever strain Josiah (J04324); LCMV, lymphocytic choriomeningitis strain Armstrong 53b (AY847350); MACV, Machupo strain Carvallo (AY619643); JUNV, Junin strain MC2 (D10072); TCRV, Tacaribe strain TRVL 11598 (P31840);
562			GTOV, Guanarito (NC—005077); SABV, Sabia (NC—006317); LATV, Latino strain Maru 10924 (AF485259); PICV, Pichinde (U77602); PIRV, Pirital (NC—005894); and WWAV, Whitewater Arroyo (AF228063)
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580			Compound ST-600037 was identified as one of the most potent and selective compounds from within the pool of 25 quality hits
581			Chemical analogs of this compound were obtained/synthesized and tested - ST-600193 displayed enhanced potency and selectivity relative to ST-600037
582			ST-600193 is also a potent inhibitor of pseudotyped viral infection mediated by the envelopes of the New World arenaviruses Guanarito (EC50<1 nM) and Tacaribe (EC50=4 nM) - may be useful for arenaviruses other than Lassa fever
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585			ST-193 antiviral activity against retroviral-based pseudotypes:
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587				Phylogeny of
588			GP	GP Source				IC50 (µM) ± SEM
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590			Lassa	Old World arenavirus; Josiah strain				0.0016 ± 0.0003
591			LCMV	Old World arenavirus; Armstrong 53b				31 ± 4
592			Pichinde	New World arenavirus, clade A				2.6 ± 0.5
593			Junín	New World arenavirus, clade B1				0.0002 ± 0.00003
594			Machupo	New World arenavirus, clade B1				0.0023 ± 0.0013
595			Tacaribe	New World arenavirus, clade B1				0.004 ± 0.002
596			Guanarito	New World arenavirus, clade B2				0.00034 ± 0.00007
597			Sabia	New World arenavirus, clade B3				0.012 ± 0.003
598			VSV	rhabdovirus				29 ± 2.5
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601			Site-directed mutagenesis of predicted ST-193 sensitivity determinants:
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603				Site #1	Site #2			IC50 relative
604			GP	(421)	(425)	IC50 (µM) ± SEM		to LASV
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606			LASV wt	Val	Val	0.0016 ± 0.0003		1
607			LASV dbl	Met	Met	24 ± 3		15200
608			LASV #1	Met	Val	1.4 ± 0.3		850
609			LASV #2	Val	Met	6.1 ± 1.3		3800
610			LCMV wt	Met	Met	31 ± 4		19600
611			LCMV #1	Val	Met	27 ± 4		16900
612			LCMV dbl	Val	Val	26 ± 4		16200
613			Pichinde wt	Thr	Phe	2.6 ± 0.5		1600
614			Pichinde #1	Val	Phe	0.046 ± 0.025		29
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617			Observations and presence of multiple ST-193 sensitivity determinants within the fusogenic GP2 subunit suggest that ST-193 blocks GP-mediated entry at a post-attachment stage
618			ST-193 might prevent or perturb conformational rearrangement of GP, or inhibit lipid mixing, thereby preventing fusion with the host cell
619			Alternatively, ST-193 could interact with the membrane-proximal domain, in the 409-413 region identified following genetic selection
620			Another possibility is that ST-193 might disrupt protein-protein interactions within or near the TMD
621			Sensitivity to at least three dissimilar antiviral compounds (ST-193, ST-294, and ST-761) has been mapped to the TMD region of GP2, with overlapping yet quite distinct patterns of genetic resistance
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623		8518960	benzenesulfonamide derivatives and analogs for treatment of Arenaviruses
624
625										Molecular	EC50/90 (µM)			Specificity
626			No.	Chemical Name				Activity		Weight	Yield			(µM)		Structure
627			1	N-(4-Diethylsulfamoyl-phenyl)-2-				EC50 < 1 uM		414.48	4.3/10.7 Den-1 0.3/5.2			1.2 Modoc >50
628				(4-oxo-4H-quinazolin-3-yl)-acetamide							Den-2 1.0/8.2 Den-3			BVDV 0.3 C6/36
629											1.7/4.1 Den-4
630
631
632
633														6.2 Modoc >50
634			2	N-(5-Diethylsulfamoyl-2-methoxy-phenyl)-				EC50 < 1 uM		328.43	7.6/8.9 Den-1 0.3/4.1			BVDV 0.7 C6/36
635				isobutyramide							Den-2 5.5/13.3 Den-3
636											2.1/12.5 Den-4