ES2661510T3 - Uso de inhibidores de la actividad o función de PI3K - Google Patents
Uso de inhibidores de la actividad o función de PI3K Download PDFInfo
- Publication number
- ES2661510T3 ES2661510T3 ES12818825.7T ES12818825T ES2661510T3 ES 2661510 T3 ES2661510 T3 ES 2661510T3 ES 12818825 T ES12818825 T ES 12818825T ES 2661510 T3 ES2661510 T3 ES 2661510T3
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- ES
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- Prior art keywords
- alkyl
- amino
- alkoxy
- hydroxy
- halo
- 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.)
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- 108091007960 PI3Ks Proteins 0.000 title abstract description 12
- 239000003112 inhibitor Substances 0.000 title abstract description 9
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 title abstract 2
- 230000000694 effects Effects 0.000 title description 2
- -1 C1-alkoxy C8 Chemical group 0.000 abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 10
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 9
- 229910052736 halogen Inorganic materials 0.000 abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 9
- 239000012828 PI3K inhibitor Substances 0.000 abstract description 8
- 125000005842 heteroatom Chemical group 0.000 abstract description 8
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 abstract description 8
- 102000001708 Protein Isoforms Human genes 0.000 abstract description 7
- 108010029485 Protein Isoforms Proteins 0.000 abstract description 7
- 150000002367 halogens Chemical group 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 125000004043 oxo group Chemical group O=* 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
- 125000002757 morpholinyl group Chemical group 0.000 abstract description 3
- 125000004193 piperazinyl group Chemical group 0.000 abstract description 3
- 125000003386 piperidinyl group Chemical group 0.000 abstract description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract description 3
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 abstract description 3
- 102000008235 Toll-Like Receptor 9 Human genes 0.000 abstract description 2
- 108010060818 Toll-Like Receptor 9 Proteins 0.000 abstract description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 3
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 3
- 125000004076 pyridyl group Chemical group 0.000 abstract 3
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 abstract 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 abstract 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- NFKMPKOGCRBAJF-UHFFFAOYSA-N $l^{1}-azanylformonitrile Chemical compound [N]C#N NFKMPKOGCRBAJF-UHFFFAOYSA-N 0.000 abstract 1
- FHLXQXCQSUICIN-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrido[3,2-d]pyrimidine Chemical group C1=CC=C2NCNCC2=N1 FHLXQXCQSUICIN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 abstract 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 abstract 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 abstract 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 abstract 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 abstract 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 abstract 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 abstract 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 abstract 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 abstract 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 abstract 1
- 206010063094 Cerebral malaria Diseases 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
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- 125000003725 azepanyl group Chemical group 0.000 abstract 1
- 125000004069 aziridinyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 230000009454 functional inhibition Effects 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract 1
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
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- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 125000003551 oxepanyl group Chemical group 0.000 abstract 1
- 125000003566 oxetanyl group Chemical group 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 239000012634 fragment Substances 0.000 description 12
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 10
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 10
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 8
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- CQZXDIHVSPZIGF-UHFFFAOYSA-N 1-methylimidazole-4-carbaldehyde Chemical compound CN1C=NC(C=O)=C1 CQZXDIHVSPZIGF-UHFFFAOYSA-N 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- LRGBDJBDJXZTTD-UHFFFAOYSA-N 1h-pyrazole-4-carbaldehyde Chemical compound O=CC=1C=NNC=1 LRGBDJBDJXZTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- YRJNUIQFTSGXGK-UHFFFAOYSA-N 5-methyl-1,3,4-oxadiazole-2-carbaldehyde Chemical compound CC1=NN=C(C=O)O1 YRJNUIQFTSGXGK-UHFFFAOYSA-N 0.000 description 2
- 102000004889 Interleukin-6 Human genes 0.000 description 2
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- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
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- 239000012091 fetal bovine serum Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- DXBWJLDFSICTIH-UHFFFAOYSA-N pyrazine-2-carbaldehyde Chemical compound O=CC1=CN=CC=N1 DXBWJLDFSICTIH-UHFFFAOYSA-N 0.000 description 2
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 241000701447 unidentified baculovirus Species 0.000 description 2
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- 108091026890 Coding region Proteins 0.000 description 1
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- 241000699666 Mus <mouse, genus> Species 0.000 description 1
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- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
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- 102000002689 Toll-like receptor Human genes 0.000 description 1
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- DHDIBUUKHMDGSQ-INIZCTEOSA-N [(3s)-3-[[6-[6-methoxy-5-(trifluoromethyl)pyridin-3-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]oxy]pyrrolidin-1-yl]-(1-methylpyrazol-4-yl)methanone Chemical compound C1=C(C(F)(F)F)C(OC)=NC=C1N1CC2=C(O[C@@H]3CN(CC3)C(=O)C3=CN(C)N=C3)N=CN=C2CC1 DHDIBUUKHMDGSQ-INIZCTEOSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
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- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
- A61K31/495—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
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
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- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
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- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A61P33/06—Antimalarials
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- A—HUMAN NECESSITIES
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- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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| JP2014509648A (ja) | 2011-03-28 | 2014-04-21 | メイ プハルマ,インコーポレーテッド | (α−置換シクロアルキルアミノ及びヘテロシクリルアミノ)ピリミジニル及び1,3,5−トリアジニルベンズイミダゾール、その医薬組成物、並びに増殖性疾患の治療におけるそれらの使用 |
| US8530470B2 (en) | 2011-04-13 | 2013-09-10 | Astrazeneca Ab | Chromenone derivatives |
| EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
| EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine derivatives as PI3K inhibitors |
| CN103987699A (zh) | 2011-10-21 | 2014-08-13 | 诺华股份有限公司 | 作为pi3k调节剂的喹唑啉衍生物 |
| ES2661510T3 (es) | 2011-12-15 | 2018-04-02 | Novartis Ag | Uso de inhibidores de la actividad o función de PI3K |
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