IP Library Granted Patent US 9,060,515
Granted Patent B2
US 9,060,515 · App. 14/365,948 · Granted Jun 23, 2015

Heterocyclic urea compounds

Inventors: Edward Malcolm Tyndall (Notting Hill, AU); Lloyd George Czaplewski (Abingdon, GB); Colin William Gordon Fishwick (Leeds, GB); Andrew Ian Yule (Leeds, GB); Jeffrey Peter Mitchell (Notting Hill, AU); Kelly Helen Anderson (Notting Hill, AU); Gary Robert William Pitt (Notting Hill, AU)
Assignee: Biota Europe Ltd.
A01N47/36C07D401/14C07D413/14C07D213/80C07F9/588C07D401/12C07D413/12C07D417/12C07D213/75C07D213/82C07D237/24C07D405/12C07D239/42C07D239/48C07D471/04A01N47/30
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Quick Facts
Patent No.
US 9,060,515
App. No.
14/365,948
Granted
Jun 23, 2015
Kind
B2
Abstract

The present invention provides a compound of the following formula, racemates, enantiomers and salts thereof. Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

Claims (302)

1. A compound of Formula (I), a racemate, an enantiomer or a salt thereof:

wherein

X is selected from C(═X 1 ), S(═O) and SO 2 ;

X 1 is selected from O, S and NR 4 ;

R 1 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl, CR 5 (R 6 ) 2 , NR 4 SO 2 R 5 , OR 6 , SR 6 , NH 2 , NR 5 R 6 and NR a R b where R a and R b join with the N to which they are attached to form an optionally substituted 5-10 membered heterocyclic ring;

R 2 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

R 3 is an optionally substituted C 1-6 alkyl;

R 4 is H or an optionally substituted C 1-6 alkyl;

R 5 is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

Each R 6 is H or is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

t is an integer selected from 0, 1, 2 and 3 wherein each (CH 2 ) t when present may be independently optionally substituted;

Z 1 , Z 2 and Z 3 are each independently selected from CR 7 and N where R 7 is selected from H, halo or an optional substituent and further where at least one of Z 1 , Z 2 or Z 3 is N; and

each cycloalkyl, cycloalkenyl, aryl, heterocyclyl and heteroaryl ring may be a monocyclic or fused bicyclic ring system.

2. A compound according to claim 1 wherein X is C(═X 1 ), X 1 is selected from O, S and NR 4 and R 1 is selected from NH 2 , NR 5 R 6 and NR a R b .

3. A compound of claim 1 of Formula (Ia), a racemate, an enantiomer or a salt thereof:

wherein

X 1 is selected from O, S or NR 4 ;

R 1 is selected from NH 2 , NR 5 R 6 and NR a R b where R a and R b join with the N to which they are attached to form an optionally substituted 5-10 membered heterocyclic ring;

R 2 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

R 3 is an optionally substituted C 1-6 alkyl;

R 4 is H or an optionally substituted C 1-6 alkyl;

R 5 is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

R 6 is H or is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

t is an integer selected from 0, 1, 2 and 3 and wherein each (CH 2 ) t when present may be independently optionally substituted; and

Z 1 , Z 2 and Z 3 are each independently selected from CR 7 and N where each R 7 is independently selected from H, halo or an optional substituent and further where at least one of Z 1 , Z 2 or Z 3 is N.

4. A compound of claim 1 wherein X 1 is O.

5. A compound of claim 1 wherein one of Z 1 , Z 2 or Z 3 is N and the two remaining are each CR 7 where each R 7 is independently selected from selected from H, halo or an optional substituent.

6. A compound of claim 1 wherein two of Z 1 , Z 2 or Z 3 are N and the one remaining is CR 7 where R 7 is independently selected from selected from H, halo or an optional substituent.

7. A compound of claim 1 wherein R 1 is NR a R b and R a and R b join with the N to which they are attached to form an optionally substituted 5- or 6-membered heterocyclic ring.

8. A compound accordingly to claim 1 wherein R 1 is NR 5 R 6 .

9. A compound of claim 1 of Formula (Ib), a racemate, an enantiomer or a salt thereof:

wherein

R 2 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

R 5 is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;

R 6 is H or is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl; and

t is an integer selected from 0, 1, 2 and 3 wherein each (CH 2 ) t when present may be independently optionally substituted.

10. A compound of claim 1 wherein R 2 is selected from an optionally substituted cyclohexyl, an optionally substituted (CH 2 ) t phenyl, an optionally substituted 5-6-membered heterocyclyl and an optionally substituted (CH 2 ) t 5-6-membered heteroaryl ring where t is 0 or 1.

11. A compound of claim 1 wherein R 5 is selected from an optionally substituted C 1-3 alkyl, an optionally substituted C 3-6 cycloalkyl, an optionally substituted (CH 2 ) t phenyl, an optionally substituted 5-6-membered heterocyclyl, an optionally substituted (CH 2 ) t 5-6-membered heteroaryl ring and an optionally substituted 9-10-membered heteroaryl ring where t is an integer 0, 1 or 2.

12. A compound of claim 1 wherein R 2 and R 5 are each independently selected from an optionally substituted (CH 2 ) t phenyl, an optionally substituted (CH 2 ) t 5-6-membered heterocyclyl, an optionally substituted (CH 2 ) t 5-6-membered heteroaryl ring and an optionally substituted (CH 2 ) t 9-10-membered heteroaryl ring where t is an integer 0, 1 or 2 and R 6 is H.

13. A compound of claim 1 selected from the group consisting of:

6-(3-ethylureido)-N-m-tolyl-4-(m-tolylamino)nicotinamide;

6-(3-ethylureido)-N-(thiazol-2-yl)-4-(m-tolylamino)nicotinamide;

4-(cyclohexylamino)-6-(3-ethylureido)-N-m-tolylnicotinamide;

N-(3-chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

2-(3-ethylureido)-N-phenyl-4-(phenylamino)pyrimidine-5-carboxamide;

2-(3-ethylureido)-4-(phenylamino)-N-(pyridin-3-yl)pyrimidine-5-carboxamide;

N-(3-chlorophenyl)-2-(3-ethylureido)-4-(phenylamino)pyrimidine-5-carboxamide;

N-ethyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

N-(2-chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(1-methyl-1H-pyrazol-5-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(2-(trifluoromethyl)phenyl) nicotinamide;

ethyl (2E)-3-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}prop-2-enoate;

6-(3-ethylureido)-N-phenyl-4-(pyridin-3-ylamino)nicotinamide;

6-(3-ethylureido)-4-(4-methoxyphenylamino)-N-(pyridin-3-yl)nicotinamide;

ethyl 4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoate;

4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoic acid;

6-(3-ethylureido)-N-phenyl-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-m-tolylnicotinamide;

6-(3-ethylureido)-N-(pyridin-3-yl)-4-(pyridin-3-ylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-3-yl)nicotinamide;

methyl 4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)picolinate;

ethyl 6-(3-ethylureido)-4-(pyridin-3-ylmethylamino)nicotinate;

6-(3-ethylureido)-N-(6-morpholinopyridin-3-yl)-4-(phenylamino)nicotinamide;

N-(6-acetamidopyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-phenyl-4-(pyridin-3-ylmethylamino)nicotinamide;

6-(3-ethylureido)-N-(pyridin-3-yl)-4-(pyridin-3-ylmethylamino) nicotinamide;

N-(6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-3-ylmethyl)nicotinamide;

2-(3-ethylureido)-N-phenyl-4-(pyridin-3-ylamino)pyrimidine-5-carboxamide;

6-(3-ethylureido)-N,N-dimethyl-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(2-methoxyphenyl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(3-methoxyphenyl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(4-methoxyphenyl)-4-(phenylamino)nicotinamide;

N-(4-chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

2-(3-ethylureido)-N-(pyridin-3-yl)-4-(pyridin-3-ylamino)pyrimidine-5-carboxamide;

6-(3-ethylureido)-N-isopropyl-4-(phenylamino)nicotinamide;

N-cyclopentyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

N-cyclopropyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-methyl-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(2-methoxyethyl)-4-(phenylamino)nicotinamide;

1-ethyl-3-(5-(morpholine-4-carbonyl)-4-(phenylamino)pyridin-2-yl)urea;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-4-yl)nicotinamide;

6-(3-ethylureido)-N-phenethyl-4-(phenylamino)nicotinamide;

N-benzyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

N-cyclohexyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-p-tolylnicotinamide

6-(3-ethylureido)-4-(phenylamino)-N-(4-(trifluoromethyl)phenyl) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(3-(trifluoromethyl)phenyl) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-2-yl)nicotinamide;

N-(3,5-dimethylisoxazol-4-yl)-6-(3-ethylureido)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-4-ylmethyl)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-2-ylmethyl)nicotinamide;

1-ethyl-3-(5-(4-methylpiperazine-1-carbonyl)-4-(phenylamino)pyridin-2-yl)urea;

1-(5-(4-acetylpiperazine-1-carbonyl)-4-(phenylamino)pyridin-2-yl)-3-ethylurea;

6-(3-ethylureido)-N-(4-fluorophenyl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(3-fluorophenyl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(2-fluorophenyl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-o-tolylnicotinamide;

6-(3-ethylureido)-N-(1-methyl-1H-pyrazol-3-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyrimidin-5-yl)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(thiazol-2-yl)nicotinamide;

6-(3-ethylureido)-N-(6-methoxypyridin-3-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(pyridazin-4-yl)nicotinamide;

6-(3-ethylureido)-N-(1-methyl-1H-pyrazol-4-yl)-4-(phenylamino) nicotinamide;

N-(3,5-difluorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

methyl 4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)benzoate;

4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)benzoic acid;

N-(3,4-difluorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

ethyl 2-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)acetate;

2-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)acetic acid;

N-(benzo[d]thiazol-2-yl)-6-(3-ethylureido)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(4-methylthiazol-2-yl)-4-(phenylamino) nicotinamide;

N-(3,5-dimethylphenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(6-(trifluoromethyl)pyridin-3-yl) nicotinamide;

6-(3-ethylureido)-N-(imidazo[1,2-a]pyridin-6-yl)-4-(phenylamino) nicotinamide;

methyl 3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)propanoate;

3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)propanoic acid;

6-(3-ethylureido)-N-(5-methoxypyridin-3-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(2-methyl-4-oxo-4H-chromen-7-yl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(6-methylpyridin-3-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(6-(4-fluorophenoxyl)pyridin-3-yl)-4-(phenylamino)nicotinamide

6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide;

5-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)nicotinic acid;

6-(3-ethylureido)-N-(5-fluoropyridin-3-yl)-4-(phenylamino) nicotinamide;

methyl 4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)-1-methyl-1H-pyrrole-2-carboxylate;

3-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoic acid;

6-(3-ethylureido)-N-(3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-4-(phenylamino)nicotinamide;

methyl 5-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)nicotinate;

6-(3-ethylureido)-N-(2-methylpyridin-4-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(5-methylpyridin-3-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-4-(phenylamino)-N-(quinolin-3-yl)nicotinamide;

6-(3-ethylureido)-N-(3-fluoro-5-methylphenyl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(1-methyl-1H-indol-4-yl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(6-(isopropylamino)pyridin-3-yl)-4-(phenylamino) nicotinamide;

methyl 4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoate;

methyl 3-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoate;

N-(6-(dimethylamino)pyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(6-(4-hydroxypiperidin-1-yl)pyridin-3-yl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(6-methoxyquinolin-3-yl)-4-(phenylamino) nicotinamide;

methyl 2-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)benzo[d]thiazole-6-carboxylate;

4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)-1-methyl-1H-pyrrole-2-carboxylic acid;

N-(6-cyanopyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

4-(2-chlorophenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl) nicotinamide;

4-(4-chlorophenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl) nicotinamide;

4-(3-chlorophenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl) nicotinamide;

6-(3-ethylureido)-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)-N-(pyridin-3-yl)nicotinamide;

6-(3-ethylureido)-4-(2-methoxyphenylamino)-N-(pyridin-3-yl)nicotinamide;

ethyl 2-(4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)phenyl)acetate;

6-(3-ethylureido)-4-(3-methoxyphenylamino)-N-(pyridin-3-yl)nicotinamide;

1-(5-benzoyl-4-(phenylamino)pyridin-2-yl)-3-ethylurea;

6-(3-ethylureido)-4-(1-methyl-1H-pyrazol-4-ylamino)-N-(pyridin-3-yl)nicotinamide;

2-(4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)phenyl)acetic acid;

4-(3,5-dimethylisoxazol-4-ylamino)-6-(3-ethylureido)-N-(pyridin-3-yl)nicotinamide;

6-(3-ethylureido)-4-(1-methyl-1H-pyrazol-3-ylamino)-N-(pyridin-3-yl)nicotinamide;

6-(3-ethylureido)-N-(4-(3-hydroxypropyl)phenyl)-4-(phenylamino) nicotinamide;

N-(4-(3-amino-3-oxopropyl)phenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

N-(4-(3-(dimethylamino)-3-oxopropyl)phenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(4-(3-(methylamino)-3-oxopropyl)phenyl)-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-methyl-N-phenyl-4-(phenylamino)nicotinamide;

6-(3-ethylureido)-N-(4-(3-oxobutyl)phenyl)-4-(phenylamino) nicotinamide;

6-(3-ethylureido)-N-(4-(3-(methoxy(methyl)amino)-3-oxopropyl)phenyl)-4-(phenylamino)nicotinamide;

4-(4-(dimethylcarbamoyl)phenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl)nicotinamide;

4-(4-carbamoylphenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl)nicotinamide;

6-(3-ethylureido)-4-(4-(methylcarbamoyl)phenylamino)-N-(pyridin-3-yl)nicotinamide;

1-ethyl-3-(5-(2-phenylacetyl)-4-(phenylamino)pyridin-2-yl)urea;

6-(3-ethylureido)-4-(4-(hydroxymethyl)phenylamino)-N-(pyridin-3-yl)nicotinamide;

methyl 3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)-2,2-dimethylpropanoate;

3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)-2,2-dimethylpropanoic acid;

ethyl 3-(4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)phenyl)propanoate;

N-(4-azidophenyl)-4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridine-3-carboxamide;

ethyl 1-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-1H-1,2,3-triazole-4-carboxylate;

6-[(ethylcarbamoyl)amino]-N-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-4-(phenylamino)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-N-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-4-(phenylamino)pyridine-3-carboxamide;

ethyl 1-{5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}-4-methylpiperidine-4-carboxylate;

(2E)-3-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}prop-2-enoic acid;

3-[4-({2-[(ethylcarbamoyl)amino]-5-(pyridin-3-ylcarbamoyl)pyridin-4-yl}amino)phenyl]propanoic acid;

6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(4-methylphenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)-4-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)-4-{[4-(trifluoromethyl)phenyl]amino}pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(2-fluorophenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(6-methoxypyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

ethyl {4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenoxy}acetate;

methyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

methyl 3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenoxy}acetic acid;

N-(6-chloropyridin-3-yl)-6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-N-[2-(3-hydroxyazetidin-1-yl)pyrimidin-5-yl]-4-(pyridin-3-ylamino)pyridine-3-carboxamide;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

methyl 1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)methyl]cyclobutanecarboxylate;

1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)methyl]cyclobutanecarboxylic acid;

methyl 1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}amino)methyl]cyclobutanecarboxylate;

6-[(ethylcarbamoyl)amino]-4-[(5-methylpyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}amino)methyl]cyclobutanecarboxylic acid;

methyl 3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoate;

3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)-N-[4-[2-(1H-tetrazol-5-yl)ethyl]phenyl]pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(2-methylpyridin-4-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(2-methoxypyridin-4-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

ethyl 1-({5-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)cyclobutanecarboxylate;

1-({5-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)cyclobutanecarboxylic acid;

3-{5-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}propanoic acid;

6-[(ethylcarbamoyl)amino]-4-[(6-methylpyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)methyl]cyclobutanecarboxylic acid;

(1R,2R)-2-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;

methyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoate;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

4-{[6-(acetylamino)pyridin-3-yl]amino}-6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)-4-(pyrimidin-5-ylamino)pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(5-methoxypyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-[4-[[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)anilino]pyridine-3-carbonyl]amino]phenyl]propanoic acid;

3-{4-[({4-[(3-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

methyl 3-{5-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}propanoate;

ethyl (1R,2R)-2-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylate;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(2-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-{4-[({4-[(2-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluoro-3-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenyl]pyridine-3-carboxamide;

3-{4-[({6-[(methylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(2-methoxypyridin-4-yl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-{4-[({4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-[4-[[6-(ethylcarbamoylamino)-4-(3,4,5-trifluoroanilino)pyridine-3-carbonyl]amino]phenyl]propanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluoro-4-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(pyridin-2-ylethynyl)phenyl]pyridine-3-carboxamide;

(1R,2R)-2-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;

(1R,2R)-2-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino) pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;

N-{4-[4-(aminomethyl)-1H-1,2,3-triazol-1-yl]phenyl}-4-[(4-chloro phenyl)amino]-6-[(ethylcarbamoyl)amino]pyridine-3-carboxamide;

tert-butyl 1-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}-L-prolinate;

3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[4-(methoxycarbonyl)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)-2,2-dimethylpropanoic acid;

methyl 1-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-1H-pyrrole-2-carboxylate;

1-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}-1H-pyrrole-2-carboxylic acid;

3-{4-[({4-[(3-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-N-[4-(pyrrolidin-1-ylmethyl)phenyl]pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-N-[4-(morpholin-4-ylmethyl)phenyl]pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-N-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}pyridine-3-carboxamide;

4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(pyrrolidin-1-ylmethyl)phenyl]pyridine-3-carboxamide;

4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(morpholin-4-ylmethyl)phenyl]pyridine-3-carboxamide;

4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}pyridine-3-carboxamide;

diethyl {4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]benzyl}phosphonate;

{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]benzyl}phosphonic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)-N-[4-(1H-tetrazol-5-ylmethyl)phenyl]pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-N-{4-[(methylsulfamoyl)methyl]phenyl}-4-(phenylamino)pyridine-3-carboxamide;

5-[(ethylcarbamoyl)amino]-3-(phenylamino)-N-(pyridin-3-yl)pyrazine-2-carboxamide;

6-[(ethylcarbamoyl)amino]-N-phenyl-4-(phenylamino)pyridazine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-N-[4-(methylcarbamoyl)phenyl]-4-(phenylamino)pyridine-3-carboxamide;

N-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}-6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridine-3-carboxamide;

ethyl 3-{4-[({4-[(3,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluoro-4-methyl phenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluoro-3-methylphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 3-{4-[({4-[(4-chloro-2-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

3-{4-[({4-[(3,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluoro-4-methylphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluoro-3-methylphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({4-[(4-chloro-2-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

ethyl 3-{4-[({4-[(3,5-dichlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 3-{4-[({4-[(3-chloro-4-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 3-{4-[({4-[(2,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

3-{4-[({4-[(3,5-dichlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({4-[(3-chloro-4-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({4-[(2,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

6-[(ethylcarbamoyl)amino]-4-(phenylamino)-N-(4-sulfamoylphenyl) pyridine-3-carboxamide;

6-[(ethylcarbamoyl)amino]-N-{4-[(methylsulfonyl)amino]phenyl}-4-(phenylamino)pyridine-3-carboxamide;

{3-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]-1H-pyrazol-1-yl}acetic acid;

ethyl 3-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

3-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(5-fluoropyridin-3-yl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;

3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[3-(pentafluorothio)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;

2-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;

3-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;

3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[3-(trifluoromethyl)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;

3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[3-(trifluoromethoxy)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;

3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[4-(trifluoromethoxy)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;

5-[(ethylcarbamoyl)amino]-3-(phenylamino)-N-(pyridin-3-yl)pyridine-2-carboxamide;

4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(morpholin-4-ylmethyl)phenyl]pyridine-3-carboxamide;

4-[(3,5-difluorophenyl)amino]-N-(4-{[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl}phenyl)-6-[(ethylcarbamoyl)amino]pyridine-3-carboxamide;

ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(2,3,4-trifluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;

ethyl 2-[[4-anilino-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]thiazole-4-carboxylate;

4-(4-chloroanilino)-6-(ethylcarbamoylamino)-N-(2-methylpyrimidin-5-yl)pyridine-3-carboxamide;

ethyl 3-[[4-anilino-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]benzoate;

1-[[4-[[4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]phenyl]methyl]pyrrolidine-2-carboxylic acid; and

1-[[4-[[4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]phenyl]methyl]piperidine-2-carboxylic acid;

a racemate, an enantiomer or a salt thereof.

14. An antibacterial agent comprising a compound according to claim 1 , a racemate, an enantiomer or a pharmaceutically acceptable salt thereof.

15. A pharmaceutical composition comprising a compound according claim 1 , a racemate, an enantiomer or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient or carrier.

16. A method for the treatment of a bacterial infection comprising administration of a compound according to claim 1 , a racemate, an enantiomer or a pharmaceutically acceptable salt thereof, to a subject suffering from said infection.

17. A method of treating bacterial contamination of a substrate comprising applying to the site of such contamination an amount of a compound according to claim 1 , a racemate, an enantiomer or pharmaceutically acceptable salt thereof sufficient to inhibit bacterial growth.

18. A process for the manufacture of a compound according to claim 1 via an intermediate of formula (II):

wherein R′ is a halo or NH 2 group and R 1 , R 2 , Z 1 , Z 2 , Z 3 and X are as defined in claim 1 ; or

via an intermediate of formula (III):

wherein R″ is H or C 1-6 alkyl and R 2 , R 3 , Z 1 , Z 2 and Z 3 are as defined in claim 1 ; or

via an intermediate of formula (IV):

wherein X, R 1 , R 3 , Z 1 , Z 2 and Z 3 are as defined in claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2016
From: BIOTA EUROPE LIMITED
To: SPERO GYRASE, INC.
Reel/Frame 038569/0773 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2015
From: CZAPLEWSKI, LLOYD GEORGE; FISHWICK, COLIN WILLIAM GORDAN; YULE, IAN ANDREW; TYNDALL, EDWARD MALCOLM; MITCHELL, JEFFREY PETER; ANDERSON, KELLY HELEN; PITT, GARY ROBERT WILLIAM
To: BIOTA EUROPE LTD
Reel/Frame 034938/0447 →
Continuity (2)
Provisional Application 61578385 · Dec 21, 2011
Related Publication 20140323486A1 · Oct 30, 2014