CA2881472A1 - Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways - Google Patents
Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways Download PDFInfo
- Publication number
- CA2881472A1 CA2881472A1 CA2881472A CA2881472A CA2881472A1 CA 2881472 A1 CA2881472 A1 CA 2881472A1 CA 2881472 A CA2881472 A CA 2881472A CA 2881472 A CA2881472 A CA 2881472A CA 2881472 A1 CA2881472 A1 CA 2881472A1
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- CA
- Canada
- Prior art keywords
- phenyl
- substituted
- thiadiazol
- amine
- sulfonyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title abstract description 11
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 title description 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 title description 2
- 230000019491 signal transduction Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 63
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
- 230000004900 autophagic degradation Effects 0.000 claims abstract description 25
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 230000037361 pathway Effects 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 245
- -1 -NR m R n Chemical group 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 150000002367 halogens Chemical group 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 24
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 201000002832 Lewy body dementia Diseases 0.000 claims description 6
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- METQSAABMLHWQI-UHFFFAOYSA-N (4-chlorophenyl)-[4-(1,3,4-thiadiazol-2-ylamino)phenyl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1NC1=NN=CS1 METQSAABMLHWQI-UHFFFAOYSA-N 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 208000019622 heart disease Diseases 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- HKUJIISFLUFFCV-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]-[4-(1,3,4-thiadiazol-2-ylamino)phenyl]methanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)C=2C=CC(NC=3SC=NN=3)=CC=2)=C1 HKUJIISFLUFFCV-UHFFFAOYSA-N 0.000 claims description 2
- LQHONOCAMPXWOW-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-1,3-thiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC=3SC=CN=3)=CC=2)=C1 LQHONOCAMPXWOW-UHFFFAOYSA-N 0.000 claims description 2
- USANJCUYKQTNCU-UHFFFAOYSA-N n-[[5-[[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]amino]-1,3,4-thiadiazol-2-yl]methyl]acetamide Chemical compound S1C(CNC(=O)C)=NN=C1NC1=CN=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=N1 USANJCUYKQTNCU-UHFFFAOYSA-N 0.000 claims description 2
- PUCFTQBPVTZKNA-UHFFFAOYSA-N n-[[5-[[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]amino]-1,3,4-thiadiazol-2-yl]methyl]methanesulfonamide Chemical compound S1C(CNS(=O)(=O)C)=NN=C1NC1=CN=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=N1 PUCFTQBPVTZKNA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- POMFIGZNWGBYOY-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-4-n-(1,3,4-thiadiazol-2-yl)benzene-1,4-diamine Chemical compound C1=CC(Cl)=CC=C1NC(C=C1)=CC=C1NC1=NN=CS1 POMFIGZNWGBYOY-UHFFFAOYSA-N 0.000 claims 1
- WMIYGLJKCSOJFI-UHFFFAOYSA-N 1-n-[4-chloro-3-(trifluoromethyl)phenyl]-4-n-(1,3,4-thiadiazol-2-yl)benzene-1,4-diamine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC=2C=CC(NC=3SC=NN=3)=CC=2)=C1 WMIYGLJKCSOJFI-UHFFFAOYSA-N 0.000 claims 1
- POVLEEZLVJLEBQ-UHFFFAOYSA-N 2-[5-[[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]amino]-1,3,4-thiadiazol-2-yl]ethanol Chemical compound S1C(CCO)=NN=C1NC1=CN=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=N1 POVLEEZLVJLEBQ-UHFFFAOYSA-N 0.000 claims 1
- QBPIQIZDOMKZBO-UHFFFAOYSA-N 5-(aminomethyl)-n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(CN)=NN=C1NC1=CN=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=N1 QBPIQIZDOMKZBO-UHFFFAOYSA-N 0.000 claims 1
- YHWARMRGGTVWMO-UHFFFAOYSA-N 5-(aziridin-1-ylmethyl)-n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(N=C1)=CN=C1NC(S1)=NN=C1CN1CC1 YHWARMRGGTVWMO-UHFFFAOYSA-N 0.000 claims 1
- TWVGPBVYAFWOKG-UHFFFAOYSA-N 5-bromo-n-[4-[3-(trifluoromethyl)phenyl]sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=CC(NC=3SC(Br)=NN=3)=CC=2)=C1 TWVGPBVYAFWOKG-UHFFFAOYSA-N 0.000 claims 1
- GUNNOKLWFBJUQO-UHFFFAOYSA-N n-[2-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylpyrimidin-5-yl]-1,3,4-thiadiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2N=CC(NC=3SC=NN=3)=CN=2)=C1 GUNNOKLWFBJUQO-UHFFFAOYSA-N 0.000 claims 1
- YUVKNKMPXOKAQO-UHFFFAOYSA-N n-[2-chloro-4-[3-(trifluoromethyl)phenyl]sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=C(Cl)C(NC=3SC=NN=3)=CC=2)=C1 YUVKNKMPXOKAQO-UHFFFAOYSA-N 0.000 claims 1
- KXSGSZSNBGOCDY-UHFFFAOYSA-N n-[3-[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl-1,2,4-triazin-6-yl]-1,3,4-thiadiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2N=NC(NC=3SC=NN=3)=CN=2)=C1 KXSGSZSNBGOCDY-UHFFFAOYSA-N 0.000 claims 1
- TXNOSKGLWXEJOQ-UHFFFAOYSA-N n-[4-(2-chloro-4-fluorophenyl)sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound ClC1=CC(F)=CC=C1S(=O)(=O)C(C=C1)=CC=C1NC1=NN=CS1 TXNOSKGLWXEJOQ-UHFFFAOYSA-N 0.000 claims 1
- QWAUXCCXJBUDOV-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1OC(C=C1)=CC=C1NC1=NN=CS1 QWAUXCCXJBUDOV-UHFFFAOYSA-N 0.000 claims 1
- JJBRYZUGWJJTPU-UHFFFAOYSA-N n-[4-(4-fluorophenyl)sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C(C=C1)=CC=C1NC1=NN=CS1 JJBRYZUGWJJTPU-UHFFFAOYSA-N 0.000 claims 1
- SZGLXKSNLYOORR-UHFFFAOYSA-N n-[4-[3-(trifluoromethoxy)phenyl]sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound FC(F)(F)OC1=CC=CC(S(=O)(=O)C=2C=CC(NC=3SC=NN=3)=CC=2)=C1 SZGLXKSNLYOORR-UHFFFAOYSA-N 0.000 claims 1
- KAQZQFPYKRJGSK-UHFFFAOYSA-N n-[4-[3-(trifluoromethyl)phenyl]sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=CC(NC=3SC=NN=3)=CC=2)=C1 KAQZQFPYKRJGSK-UHFFFAOYSA-N 0.000 claims 1
- RHSIJRLJXARZFB-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenoxy]phenyl]-1,3,4-thiadiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(OC=2C=CC(NC=3SC=NN=3)=CC=2)=C1 RHSIJRLJXARZFB-UHFFFAOYSA-N 0.000 claims 1
- PHYYVLXFAQCOLF-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl-3-fluorophenyl]-1,3,4-thiadiazol-2-amine Chemical compound C=1C=C(S(=O)(=O)C=2C=C(C(Cl)=CC=2)C(F)(F)F)C(F)=CC=1NC1=NN=CS1 PHYYVLXFAQCOLF-UHFFFAOYSA-N 0.000 claims 1
- YVUIQHKJPBSQSU-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-1,3,4-oxadiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC=3OC=NN=3)=CC=2)=C1 YVUIQHKJPBSQSU-UHFFFAOYSA-N 0.000 claims 1
- LWGDIODWJORJOC-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-1,3,4-thiadiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC=3SC=NN=3)=CC=2)=C1 LWGDIODWJORJOC-UHFFFAOYSA-N 0.000 claims 1
- SZOPGUATBWMHNR-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC=3NN=CN=3)=CC=2)=C1 SZOPGUATBWMHNR-UHFFFAOYSA-N 0.000 claims 1
- FFPBFHRJGZTMQU-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-1h-imidazol-5-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC=3NC=NC=3)=CC=2)=C1 FFPBFHRJGZTMQU-UHFFFAOYSA-N 0.000 claims 1
- AXWHUZXBRSKCLL-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-1h-pyrrol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC=3NC=CC=3)=CC=2)=C1 AXWHUZXBRSKCLL-UHFFFAOYSA-N 0.000 claims 1
- URTSUAFRXCZONN-UHFFFAOYSA-N n-[4-[4-chloro-3-(trifluoromethyl)phenyl]sulfonylphenyl]-2h-tetrazol-5-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)C=2C=CC(NC3=NNN=N3)=CC=2)=C1 URTSUAFRXCZONN-UHFFFAOYSA-N 0.000 claims 1
- SKFKQHGEQGJBPF-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]phenyl]-1,3,4-thiadiazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(CC=2C=CC(NC=3SC=NN=3)=CC=2)=C1 SKFKQHGEQGJBPF-UHFFFAOYSA-N 0.000 claims 1
- JGXKXZOVOZYZTI-UHFFFAOYSA-N n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(N=C1)=CN=C1NC1=NN=CS1 JGXKXZOVOZYZTI-UHFFFAOYSA-N 0.000 claims 1
- IQIARBSSAQBFHI-UHFFFAOYSA-N n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-5-(morpholin-4-ylmethyl)-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(N=C1)=CN=C1NC(S1)=NN=C1CN1CCOCC1 IQIARBSSAQBFHI-UHFFFAOYSA-N 0.000 claims 1
- HXQHDPILLFXWCT-UHFFFAOYSA-N n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-5-(piperidin-1-ylmethyl)-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(N=C1)=CN=C1NC(S1)=NN=C1CN1CCCCC1 HXQHDPILLFXWCT-UHFFFAOYSA-N 0.000 claims 1
- CXKMZZFUCHIDLF-UHFFFAOYSA-N n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-5-[(4-methylpiperazin-1-yl)methyl]-1,3,4-thiadiazol-2-amine Chemical compound C1CN(C)CCN1CC(S1)=NN=C1NC1=CN=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=N1 CXKMZZFUCHIDLF-UHFFFAOYSA-N 0.000 claims 1
- HOQMPQSKSOMKEF-UHFFFAOYSA-N n-[5-(4-chlorophenyl)sulfonylpyrazin-2-yl]-5-[(4-methylsulfonylpiperazin-1-yl)methyl]-1,3,4-thiadiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC(S1)=NN=C1NC1=CN=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=N1 HOQMPQSKSOMKEF-UHFFFAOYSA-N 0.000 claims 1
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- KYUNDAOKBURETM-UHFFFAOYSA-N n-[5-[4-(trifluoromethoxy)phenyl]sulfonylpyrazin-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)C(N=C1)=CN=C1NC1=NN=CS1 KYUNDAOKBURETM-UHFFFAOYSA-N 0.000 claims 1
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- 229960002004 valdecoxib Drugs 0.000 description 1
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- 229950010696 zanapezil Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Pain & Pain Management (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201261681585P | 2012-08-09 | 2012-08-09 | |
| US61/681,585 | 2012-08-09 | ||
| PCT/US2013/054200 WO2014026039A2 (en) | 2012-08-09 | 2013-08-08 | Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways |
Publications (1)
| Publication Number | Publication Date |
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| CA2881472A1 true CA2881472A1 (en) | 2014-02-13 |
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| CA2881472A Abandoned CA2881472A1 (en) | 2012-08-09 | 2013-08-08 | Aryl-and heteroaryl-substituted benzene derivatives as modulators of pi3-kinase signalling pathways |
Country Status (8)
| Country | Link |
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| US (1) | US20150197513A1 (enExample) |
| EP (1) | EP2882726A4 (enExample) |
| JP (1) | JP2015524483A (enExample) |
| CN (1) | CN104703985A (enExample) |
| CA (1) | CA2881472A1 (enExample) |
| HK (1) | HK1206331A1 (enExample) |
| MX (1) | MX2015001793A (enExample) |
| WO (1) | WO2014026039A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BR112017003745A2 (pt) | 2014-08-29 | 2017-12-05 | Tes Pharma S R L | inibidores de semialdeído descarboxilase de ácido alfa-amino-beta-carboximucônico |
| WO2016113205A1 (de) | 2015-01-13 | 2016-07-21 | Bayer Pharma Aktiengesellschaft | Substituierte pentafluorethylpyrimidinone und ihre verwendung |
| CN108947985A (zh) * | 2017-05-22 | 2018-12-07 | 苏州偶领生物医药有限公司 | 用作自噬调节剂的化合物及其制备方法和用途 |
| CN111094278B (zh) * | 2017-09-13 | 2023-07-14 | 诺华股份有限公司 | 二苯基衍生物及其用途 |
| CN111372579B (zh) * | 2017-10-30 | 2023-08-22 | 神经孔疗法股份有限公司 | 取代的苯基磺酰基苯基三唑硫酮和其用途 |
| IL277071B2 (en) | 2018-03-08 | 2024-07-01 | Incyte Corp | AMINOPYRAZINE DIOL COMPOUNDS AS PI3K-y INHIBITORS |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| JP7506903B2 (ja) * | 2019-11-01 | 2024-06-27 | 日本メナード化粧品株式会社 | Il-37産生促進剤 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1476503A (en) * | 1973-06-21 | 1977-06-16 | Sterling Drug Inc | 1-arylamino-and 1-arylimino-pyrroles and preparation thereof |
| DE3307506A1 (de) * | 1983-03-03 | 1984-09-06 | Agfa-Gevaert Ag, 5090 Leverkusen | Fotografisches aufzeichnungsmaterial mit inhibitorvorlaeuferverbindungen |
| US20020183306A1 (en) * | 2001-05-30 | 2002-12-05 | Pfizer Inc. | Combination treatment for sleep disorders including sleep apnea |
| US20040235877A1 (en) * | 2001-09-14 | 2004-11-25 | Natsuki Ishizuka | Novel use of tricyclic compound |
| US20050228031A1 (en) * | 2004-04-13 | 2005-10-13 | Bilodeau Mark T | Tyrosine kinase inhibitors |
| US7429667B2 (en) * | 2005-01-20 | 2008-09-30 | Ardea Biosciences, Inc. | Phenylamino isothiazole carboxamidines as MEK inhibitors |
| BRPI0608910A2 (pt) * | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| JP2009500351A (ja) * | 2005-07-04 | 2009-01-08 | ドクター レディズ ラボラトリーズ リミテッド | Ampkアクチベータとしてのチアゾール誘導体 |
| WO2009117444A1 (en) * | 2008-03-17 | 2009-09-24 | Northeastern University | Inhibitors of fatty acid amide hydrolase and monoacylglycerol lipase for modulation of cannabinoid receptors |
| UY32582A (es) * | 2009-04-28 | 2010-11-30 | Amgen Inc | Inhibidores de fosfoinositida 3 cinasa y/u objetivo mamífero |
| EP2462128B1 (en) * | 2009-08-04 | 2016-09-21 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
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2013
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- 2013-08-08 WO PCT/US2013/054200 patent/WO2014026039A2/en not_active Ceased
- 2013-08-08 MX MX2015001793A patent/MX2015001793A/es unknown
- 2013-08-08 EP EP13828347.8A patent/EP2882726A4/en not_active Withdrawn
- 2013-08-08 CN CN201380052581.7A patent/CN104703985A/zh active Pending
- 2013-08-08 CA CA2881472A patent/CA2881472A1/en not_active Abandoned
- 2013-08-08 JP JP2015526717A patent/JP2015524483A/ja not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| US20150197513A1 (en) | 2015-07-16 |
| CN104703985A (zh) | 2015-06-10 |
| JP2015524483A (ja) | 2015-08-24 |
| WO2014026039A2 (en) | 2014-02-13 |
| EP2882726A4 (en) | 2016-04-06 |
| HK1206331A1 (en) | 2016-01-08 |
| EP2882726A2 (en) | 2015-06-17 |
| MX2015001793A (es) | 2015-05-07 |
| WO2014026039A4 (en) | 2014-08-14 |
| WO2014026039A3 (en) | 2014-06-26 |
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