DK2925757T3 - Compounds and compositions for the treatment of parasitic diseases - Google Patents

Compounds and compositions for the treatment of parasitic diseases Download PDF

Info

Publication number: DK2925757T3
Authority: DK; Denmark
Prior art keywords: pyridine; pyrazolo; carboxamide; phenyl; pyridin
Prior art date: 2012-11-19

Application number

DK13795977.1T

Other languages

Danish (da)

English (en)

Inventor

Arnab Kumar Chatterjee

Advait Suresh Nagle

Prasuna Paraselli

Robert Joseph Moreau

Liying Jocelyn Tan

Ravinder Reddy Kondreddi

Seh Yong Leong

Pranab Kumar Mishra

Jason Thomas Roland

Wei Lin Sandra Sim

Oliver Simon

Bryan Ks Yeung

Bin Zou

Venkatataiah Bollu

Original Assignee

Novartis Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2012-11-19

Filing date

2013-11-18

Publication date

2018-01-15

2013-11-18 Application filed by Novartis Ag filed Critical Novartis Ag

2018-01-15 Application granted granted Critical

2018-01-15 Publication of DK2925757T3 publication Critical patent/DK2925757T3/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 266
238000011282 treatment Methods 0.000 title claims description 17
239000000203 mixture Substances 0.000 title description 111
208000030852 Parasitic disease Diseases 0.000 title description 8
150000003839 salts Chemical class 0.000 claims abstract description 117
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
241000223960 Plasmodium falciparum Species 0.000 claims abstract description 30
201000010099 disease Diseases 0.000 claims abstract description 30
201000004792 malaria Diseases 0.000 claims abstract description 29
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
230000007170 pathology Effects 0.000 claims abstract description 9
-1 amino, hydroxyl Chemical group 0.000 claims description 150
125000000217 alkyl group Chemical group 0.000 claims description 64
125000001424 substituent group Chemical group 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 35
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 26
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
239000003795 chemical substances by application Substances 0.000 claims description 19
125000001072 heteroaryl group Chemical group 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical group 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
XCDRZFXDJGFXBD-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=C(C(=O)N)C=CN2N=CC=C21 XCDRZFXDJGFXBD-UHFFFAOYSA-N 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000002947 alkylene group Chemical group 0.000 claims description 12
KCSUAVGGFJSNQG-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)N=C1 KCSUAVGGFJSNQG-UHFFFAOYSA-N 0.000 claims description 10
AFEBSUBJPYNMLX-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 AFEBSUBJPYNMLX-UHFFFAOYSA-N 0.000 claims description 10
VQPZEJHSUIMXJJ-UHFFFAOYSA-N 5-[5-[(4-cyanophenyl)-(methylamino)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-n-methylpyridine-2-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(NC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)N=C1 VQPZEJHSUIMXJJ-UHFFFAOYSA-N 0.000 claims description 9
101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims description 9
101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims description 9
FIMDPLQFEMZNQZ-UHFFFAOYSA-N n-ethyl-3-[4-(methylcarbamoyl)phenyl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 FIMDPLQFEMZNQZ-UHFFFAOYSA-N 0.000 claims description 9
INEYQUSNXLVTDG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(N)N=C1 INEYQUSNXLVTDG-UHFFFAOYSA-N 0.000 claims description 8
LYBINGBMBQCIEI-MRXNPFEDSA-N 3-[4-[[(2r)-2-aminopropanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(NC(=O)[C@H](N)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 LYBINGBMBQCIEI-MRXNPFEDSA-N 0.000 claims description 8
DQHCWIQEOFOVPG-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CN2N=CC(C=3C=C4C=CNC4=NC=3)=C2C=C1C(=O)N(C)C1=CC=C(C#N)C=C1 DQHCWIQEOFOVPG-UHFFFAOYSA-N 0.000 claims description 8
IHZSERRLWDIUDF-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CN2N=CC(C=3C=C4C=CNC4=NC=3)=C2C=C1C(=O)N(C)C1=CC=C(C#N)C=N1 IHZSERRLWDIUDF-UHFFFAOYSA-N 0.000 claims description 8
ACEBZLKNNKVZGS-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(N)C=C1 ACEBZLKNNKVZGS-UHFFFAOYSA-N 0.000 claims description 7
INYLWQYLPVRIOG-UHFFFAOYSA-N 3-[6-amino-5-(dimethylcarbamoyl)pyridin-3-yl]-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=C(N)C(C(=O)N(C)C)=CC(C2=C3C=C(C=CN3N=C2)C(=O)N(C)C=2N=CC(=CC=2)C#N)=C1 INYLWQYLPVRIOG-UHFFFAOYSA-N 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
230000005764 inhibitory process Effects 0.000 claims description 7
XOHVCFFOEUGXDR-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-ethyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 XOHVCFFOEUGXDR-UHFFFAOYSA-N 0.000 claims description 7
YVQPAOQGADXRII-UHFFFAOYSA-N n-ethyl-n-(5-fluoropyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 YVQPAOQGADXRII-UHFFFAOYSA-N 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
RQRAIWVNBUQEFG-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 RQRAIWVNBUQEFG-UHFFFAOYSA-N 0.000 claims description 6
FUAXSFPIDJXYEF-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 FUAXSFPIDJXYEF-UHFFFAOYSA-N 0.000 claims description 6
GUKQBKQCUDJBSA-UHFFFAOYSA-N 3-(4-acetamidophenyl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(NC(C)=O)C=C1 GUKQBKQCUDJBSA-UHFFFAOYSA-N 0.000 claims description 5
PTEIXJMQQFZISE-UHFFFAOYSA-N 3-(4-amino-3,5-dimethylphenyl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC(C)=C(N)C(C)=C1 PTEIXJMQQFZISE-UHFFFAOYSA-N 0.000 claims description 5
BHSQRNJDDWAUDW-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-chloro-2-formylphenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=C(C=O)C=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 BHSQRNJDDWAUDW-UHFFFAOYSA-N 0.000 claims description 5
GXWIIYKIVTXJHQ-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanocyclohexyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(N)=O)=C2C=C1C(=O)N(C)C1CCC(C#N)CC1 GXWIIYKIVTXJHQ-UHFFFAOYSA-N 0.000 claims description 5
RYUOSSVZFZYALJ-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-fluorophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 RYUOSSVZFZYALJ-UHFFFAOYSA-N 0.000 claims description 5
NYIRQOMRHCHWBH-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-methyl-n-(5-methylpyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 NYIRQOMRHCHWBH-UHFFFAOYSA-N 0.000 claims description 5
NSCNEKGRISNFKI-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-methyl-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 NSCNEKGRISNFKI-UHFFFAOYSA-N 0.000 claims description 5
HSRPYWABXCSKIO-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-methyl-1-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]urea Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)NC1=CC=C(F)C=C1 HSRPYWABXCSKIO-UHFFFAOYSA-N 0.000 claims description 5
ZZXUGDGOKYDEDY-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=N1 ZZXUGDGOKYDEDY-UHFFFAOYSA-N 0.000 claims description 5
QTAMHHUFTFOTLR-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=N1 QTAMHHUFTFOTLR-UHFFFAOYSA-N 0.000 claims description 5
LTAWNKYSHWNFMT-UHFFFAOYSA-N 3-(6-amino-5-chloropyridin-3-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(Cl)=C1 LTAWNKYSHWNFMT-UHFFFAOYSA-N 0.000 claims description 5
QOKZKONINLLRQF-UHFFFAOYSA-N 3-(6-amino-5-cyanopyridin-3-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(C#N)=C1 QOKZKONINLLRQF-UHFFFAOYSA-N 0.000 claims description 5
JYPKQLSJEKQADI-UHFFFAOYSA-N 3-(6-amino-5-fluoropyridin-3-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(F)=C1 JYPKQLSJEKQADI-UHFFFAOYSA-N 0.000 claims description 5
LCBMVGDIOXWCAR-UHFFFAOYSA-N 3-(6-amino-5-methoxypyridin-3-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=C(N)C(OC)=CC(C2=C3C=C(C=CN3N=C2)C(=O)N(C)C=2N=CC(=CC=2)C#N)=C1 LCBMVGDIOXWCAR-UHFFFAOYSA-N 0.000 claims description 5
MMVFCZWRKCJRRU-UHFFFAOYSA-N 3-(6-amino-5-methylpyridin-3-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(C)=C1 MMVFCZWRKCJRRU-UHFFFAOYSA-N 0.000 claims description 5
VHVKCJJECWKSDS-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(N)N=C1 VHVKCJJECWKSDS-UHFFFAOYSA-N 0.000 claims description 5
XCYDPRNLYOSTDK-UHFFFAOYSA-N 3-[4-[(2-aminoacetyl)amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(NC(=O)CN)C=C1 XCYDPRNLYOSTDK-UHFFFAOYSA-N 0.000 claims description 5
IUMSUDBTXMWHOH-NDEPHWFRSA-N 3-[4-[[(2s)-2-amino-2-cyclohexylacetyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1([C@H](N)C(=O)NC2=CC=C(C=C2)C=2C=NN3C=CC(=CC3=2)C(=O)N(C)C=2C=CC(=CC=2)C#N)CCCCC1 IUMSUDBTXMWHOH-NDEPHWFRSA-N 0.000 claims description 5
OJLDETSJNURQBL-VWLOTQADSA-N 3-[4-[[(2s)-2-amino-3-methylbutanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(NC(=O)[C@@H](N)C(C)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 OJLDETSJNURQBL-VWLOTQADSA-N 0.000 claims description 5
LYBINGBMBQCIEI-INIZCTEOSA-N 3-[4-[[(2s)-2-aminopropanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(NC(=O)[C@@H](N)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 LYBINGBMBQCIEI-INIZCTEOSA-N 0.000 claims description 5
LQQLJLYZAUDRTO-UHFFFAOYSA-N 3-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(C(F)(F)F)=C1 LQQLJLYZAUDRTO-UHFFFAOYSA-N 0.000 claims description 5
XFLNXYYZBCWZOZ-UHFFFAOYSA-N 4-[5-(7-fluoro-2,3-dihydro-1,4-benzoxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N3C4=CC=C(F)C=C4OCC3)C=CN2N=C1 XFLNXYYZBCWZOZ-UHFFFAOYSA-N 0.000 claims description 5
JQKWXWZESAYCIW-UHFFFAOYSA-N 4-[5-(7-fluoro-3-methyl-2,3-dihydro-1,4-benzoxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N3C4=CC=C(F)C=C4OCC3C)C=CN2N=C1 JQKWXWZESAYCIW-UHFFFAOYSA-N 0.000 claims description 5
VIWNXLMAPVRFHB-UHFFFAOYSA-N 4-[5-[(4-fluorobenzoyl)-methylamino]pyrazolo[1,5-a]pyridin-3-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(N)=O)=C2C=C1N(C)C(=O)C1=CC=C(F)C=C1 VIWNXLMAPVRFHB-UHFFFAOYSA-N 0.000 claims description 5
OXMVLJHPBWICNO-UHFFFAOYSA-N 4-[5-[1-[methyl-(5-methylpyridin-2-yl)amino]ethyl]pyrazolo[1,5-a]pyridin-3-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(N)=O)=C2C=C1C(C)N(C)C1=CC=C(C)C=N1 OXMVLJHPBWICNO-UHFFFAOYSA-N 0.000 claims description 5
FOMOTRJNAJNRTM-UHFFFAOYSA-N 4-chloro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)C1=CC=C(Cl)C=C1 FOMOTRJNAJNRTM-UHFFFAOYSA-N 0.000 claims description 5
LFMDYWOTIXBDRY-UHFFFAOYSA-N 4-cyano-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 LFMDYWOTIXBDRY-UHFFFAOYSA-N 0.000 claims description 5
OBTXCMGPGHMGIT-UHFFFAOYSA-N 4-cyclopropyl-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)C(C=C1)=CC=C1C1CC1 OBTXCMGPGHMGIT-UHFFFAOYSA-N 0.000 claims description 5
CXJIVALQEWZFDB-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzenesulfonamide Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(C)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 CXJIVALQEWZFDB-UHFFFAOYSA-N 0.000 claims description 5
YLUAYXLDRUPROY-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-[4-[5-(methylamino)-1,3,4-thiadiazol-2-yl]phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound S1C(NC)=NN=C1C1=CC=C(C2=C3C=C(C=CN3N=C2)N(C)C(=O)C=2C=CC(F)=CC=2)C=C1 YLUAYXLDRUPROY-UHFFFAOYSA-N 0.000 claims description 5
MNCSCAZLWXELFK-UHFFFAOYSA-N 5-[(4-fluorophenyl)sulfanylmethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1SCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 MNCSCAZLWXELFK-UHFFFAOYSA-N 0.000 claims description 5
MCROLCIKKFTXML-UHFFFAOYSA-N 5-[(4-fluorophenyl)sulfinylmethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1S(=O)CC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 MCROLCIKKFTXML-UHFFFAOYSA-N 0.000 claims description 5
HAAMTDVCPQYNMK-UHFFFAOYSA-N 5-[(5-methylpyridin-2-yl)oxymethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound N1=CC(C)=CC=C1OCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 HAAMTDVCPQYNMK-UHFFFAOYSA-N 0.000 claims description 5
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MKWHZSORVFXAAC-UHFFFAOYSA-N 4-chloro-n-methyl-n-[[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]methyl]aniline Chemical compound C=1C=C(Cl)C=CC=1N(C)CC(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 MKWHZSORVFXAAC-UHFFFAOYSA-N 0.000 claims description 3
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ZIVQLWKYVSHZJA-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)C1=CC=C(F)C=C1 ZIVQLWKYVSHZJA-UHFFFAOYSA-N 0.000 claims description 3
YKEOOCRGJWUBBL-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]methyl]aniline Chemical compound C=1C=C(F)C=CC=1N(C)CC(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 YKEOOCRGJWUBBL-UHFFFAOYSA-N 0.000 claims description 3
POPQAGDJJFNTNA-UHFFFAOYSA-N 5-[(4-fluorophenoxy)methyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1OCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 POPQAGDJJFNTNA-UHFFFAOYSA-N 0.000 claims description 3
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IALWQEFKCYAWAN-UHFFFAOYSA-N n,5-dimethyl-n-[[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]methyl]pyridin-2-amine Chemical compound C=1C=C(C)C=NC=1N(C)CC(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 IALWQEFKCYAWAN-UHFFFAOYSA-N 0.000 claims description 3
RQUPCQCXFLJNEN-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(Cl)=CC=3)C=CN2N=C1 RQUPCQCXFLJNEN-UHFFFAOYSA-N 0.000 claims description 3
FFXJDPAXCZHDGF-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 FFXJDPAXCZHDGF-UHFFFAOYSA-N 0.000 claims description 3
NAUKWDRTUSNMMD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1CNC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 NAUKWDRTUSNMMD-UHFFFAOYSA-N 0.000 claims description 3
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HBDJXFWAWKERIG-UHFFFAOYSA-N 3-(2-aminopyridin-4-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=NC(N)=C1 HBDJXFWAWKERIG-UHFFFAOYSA-N 0.000 claims description 2
CEUMFLHANBUGHU-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-chlorophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 CEUMFLHANBUGHU-UHFFFAOYSA-N 0.000 claims description 2
AVVFTCJUJWRJIF-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanophenyl)-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(CCO)C=3C=CC(=CC=3)C#N)C=CN2N=C1 AVVFTCJUJWRJIF-UHFFFAOYSA-N 0.000 claims description 2
RETWKVPBIKVKNP-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanophenyl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 RETWKVPBIKVKNP-UHFFFAOYSA-N 0.000 claims description 2
ORBRBJUPZJBEFK-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(5-cyanopyridin-2-yl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 ORBRBJUPZJBEFK-UHFFFAOYSA-N 0.000 claims description 2
HUHVFOSBOVRBBB-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-yl)-n-(4-cyanophenyl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 HUHVFOSBOVRBBB-UHFFFAOYSA-N 0.000 claims description 2
IBMMICVBFWIOGS-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-yl)-n-(5-cyanopyridin-2-yl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 IBMMICVBFWIOGS-UHFFFAOYSA-N 0.000 claims description 2
JJXDASHHKUGLBN-UHFFFAOYSA-N 3-(6-carbamoylpyridin-3-yl)-n-(4-cyanophenyl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 JJXDASHHKUGLBN-UHFFFAOYSA-N 0.000 claims description 2
WMTRRHDMJAGPOE-UHFFFAOYSA-N 3-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(Cl)C(NS(C)(=O)=O)=C1 WMTRRHDMJAGPOE-UHFFFAOYSA-N 0.000 claims description 2
DLGFTAJFANEHOI-UHFFFAOYSA-N 4-[5-[(5-cyanopyridin-2-yl)-cyclopropylsulfamoyl]pyrazolo[1,5-a]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(S(=O)(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 DLGFTAJFANEHOI-UHFFFAOYSA-N 0.000 claims description 2
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VYLUHYBMTOAFRM-UHFFFAOYSA-N 6-[cyclopropyl-[3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carbonyl]amino]pyridine-3-carboxylic acid Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C(O)=O)C=CN2N=C1 VYLUHYBMTOAFRM-UHFFFAOYSA-N 0.000 claims description 2
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GGDDEXIVBFQSAN-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)NC=3N=CC(=CC=3)C#N)C=CN2N=C1 GGDDEXIVBFQSAN-UHFFFAOYSA-N 0.000 claims description 2
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CCSAXDPRAJEOCX-UHFFFAOYSA-N n-methyl-5-(trifluoromethyl)-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]pyridine-2-carboxamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)C1=CC=C(C(F)(F)F)C=N1 CCSAXDPRAJEOCX-UHFFFAOYSA-N 0.000 description 2
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159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000001010 sulfinic acid amide group Chemical group 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229940071103 sulfosalicylate Drugs 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
125000005323 thioketone group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
238000003354 tissue distribution assay Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
239000012443 tonicity enhancing agent Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
238000001195 ultra high performance liquid chromatography Methods 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
210000003934 vacuole Anatomy 0.000 description 1
208000037973 vector-borne parasitic disease Diseases 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Epidemiology (AREA)
Tropical Medicine & Parasitology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK13795977.1T 2012-11-19 2013-11-18 Compounds and compositions for the treatment of parasitic diseases DK2925757T3 (en)

Applications Claiming Priority (3)

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US201261728018P	2012-11-19	2012-11-19
US201361847860P	2013-07-18	2013-07-18
PCT/US2013/070601 WO2014078802A1 (en)	2012-11-19	2013-11-18	Compounds and compositions for the treatment of parasitic diseases

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US (3)	US9556169B2 (2)
EP (1)	EP2925757B1 (2)
JP (1)	JP6298472B2 (2)
CN (1)	CN105164124B (2)
AR (1)	AR093532A1 (2)
CY (1)	CY1119727T1 (2)
DK (1)	DK2925757T3 (2)
ES (1)	ES2655030T3 (2)
HR (1)	HRP20171998T1 (2)
HU (1)	HUE037600T2 (2)
LT (1)	LT2925757T (2)
ME (1)	ME03042B (2)
PL (1)	PL2925757T3 (2)
PT (1)	PT2925757T (2)
RS (1)	RS56720B1 (2)
SI (1)	SI2925757T1 (2)
TW (1)	TWI600654B (2)
UY (1)	UY35146A (2)
WO (1)	WO2014078802A1 (2)

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- 2013-11-18 LT LTEP13795977.1T patent/LT2925757T/lt unknown
- 2013-11-18 CN CN201380070822.0A patent/CN105164124B/zh not_active Expired - Fee Related
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- 2013-11-18 EP EP13795977.1A patent/EP2925757B1/en active Active
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- 2013-11-18 DK DK13795977.1T patent/DK2925757T3/en active
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Publication number	Publication date
AR093532A1 (es)	2015-06-10
CN105164124B (zh)	2017-03-15
US20180230145A1 (en)	2018-08-16
CY1119727T1 (el)	2018-06-27
CN105164124A (zh)	2015-12-16
EP2925757B1 (en)	2017-10-04
WO2014078802A1 (en)	2014-05-22
HRP20171998T1 (hr)	2018-02-09
RS56720B1 (sr)	2018-03-30
US9926314B2 (en)	2018-03-27
JP6298472B2 (ja)	2018-03-20
TWI600654B (zh)	2017-10-01
TW201429967A (zh)	2014-08-01
EP2925757A1 (en)	2015-10-07
ES2655030T3 (es)	2018-02-16
UY35146A (es)	2014-06-30
ME03042B (me)	2018-10-20
LT2925757T (lt)	2017-12-27
US9556169B2 (en)	2017-01-31
PT2925757T (pt)	2018-01-09
PL2925757T3 (pl)	2018-06-29
US20150344471A1 (en)	2015-12-03
US20160333012A1 (en)	2016-11-17
SI2925757T1 (en)	2018-01-31
JP2016505529A (ja)	2016-02-25
HUE037600T2 (hu)	2018-09-28

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