ES2433566T3 - Derivados terapéuticos de pirazoloquinolinurea - Google Patents
Derivados terapéuticos de pirazoloquinolinurea Download PDFInfo
- Publication number
- ES2433566T3 ES2433566T3 ES08770406T ES08770406T ES2433566T3 ES 2433566 T3 ES2433566 T3 ES 2433566T3 ES 08770406 T ES08770406 T ES 08770406T ES 08770406 T ES08770406 T ES 08770406T ES 2433566 T3 ES2433566 T3 ES 2433566T3
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- ES
- Spain
- Prior art keywords
- alkyl
- compound
- aryl
- optionally substituted
- animal
- 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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- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 58
- 125000003118 aryl group Chemical group 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 15
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 229910052705 radium Inorganic materials 0.000 claims abstract description 7
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 4
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 15
- 241001465754 Metazoa Species 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 230000015654 memory Effects 0.000 claims description 20
- -1 CF2H Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 150000002222 fluorine compounds Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000011737 fluorine Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 208000010877 cognitive disease Diseases 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 230000003920 cognitive function Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 230000006403 short-term memory Effects 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 230000007787 long-term memory Effects 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 208000020685 sleep-wake disease Diseases 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 235000019000 fluorine Nutrition 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 110
- 238000000034 method Methods 0.000 description 81
- 238000005160 1H NMR spectroscopy Methods 0.000 description 74
- 230000015572 biosynthetic process Effects 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 39
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 238000012549 training Methods 0.000 description 18
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 14
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000003254 radicals Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 11
- 210000000287 oocyte Anatomy 0.000 description 11
- 102000027484 GABAA receptors Human genes 0.000 description 10
- 108091008681 GABAA receptors Proteins 0.000 description 10
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 9
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 9
- 229940067157 phenylhydrazine Drugs 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 239000002299 complementary DNA Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940049706 benzodiazepine Drugs 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 5
- 0 CCCN(CC1)CCN1C(N(C=C1C2O)c3ccccc3C1=N*[C@]2c1ccccc1)=O Chemical compound CCCN(CC1)CCN1C(N(C=C1C2O)c3ccccc3C1=N*[C@]2c1ccccc1)=O 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012320 chlorinating reagent Substances 0.000 description 5
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000013612 plasmid Substances 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- DNTFNRUPWKYWSS-UHFFFAOYSA-N 5-(2,6-dimethylmorpholine-4-carbonyl)-2-phenylpyrazolo[4,3-c]quinolin-3-one Chemical compound C1C(C)OC(C)CN1C(=O)N(C=C1C2=O)C3=CC=CC=C3C1=NN2C1=CC=CC=C1 DNTFNRUPWKYWSS-UHFFFAOYSA-N 0.000 description 4
- SKBFTMUJXQJVFI-UHFFFAOYSA-N 5-(4-methylpiperidine-1-carbonyl)-2-phenylpyrazolo[4,3-c]quinolin-3-one Chemical compound C1CC(C)CCN1C(=O)N(C=C1C2=O)C3=CC=CC=C3C1=NN2C1=CC=CC=C1 SKBFTMUJXQJVFI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000283984 Rodentia Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 239000002775 capsule Substances 0.000 description 4
- XTYGFVVANLMBHE-UHFFFAOYSA-N cgs-8216 Chemical compound N1C(C2=CC=CC=C2N=C2)=C2C(=O)N1C1=CC=CC=C1 XTYGFVVANLMBHE-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- YBEOYBKKSWUSBR-UHFFFAOYSA-N ethyl 4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 YBEOYBKKSWUSBR-UHFFFAOYSA-N 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
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- BMEMBBFDTYHTLH-UHFFFAOYSA-N 1-(2-methoxyethyl)piperazine Chemical compound COCCN1CCNCC1 BMEMBBFDTYHTLH-UHFFFAOYSA-N 0.000 description 2
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- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 2
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- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 2
- IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 description 2
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 2
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94299207P | 2007-06-08 | 2007-06-08 | |
| US942992P | 2007-06-08 | ||
| PCT/US2008/066205 WO2008154442A1 (en) | 2007-06-08 | 2008-06-06 | Therapeutic pyrazoloquinoline urea derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2433566T3 true ES2433566T3 (es) | 2013-12-11 |
Family
ID=40096439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08770406T Active ES2433566T3 (es) | 2007-06-08 | 2008-06-06 | Derivados terapéuticos de pirazoloquinolinurea |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7863266B2 (enExample) |
| EP (1) | EP2164328B8 (enExample) |
| JP (1) | JP2010529144A (enExample) |
| KR (1) | KR20100038189A (enExample) |
| CN (1) | CN101686682A (enExample) |
| AU (1) | AU2008261888A1 (enExample) |
| BR (1) | BRPI0812347A2 (enExample) |
| CA (1) | CA2688405A1 (enExample) |
| ES (1) | ES2433566T3 (enExample) |
| IL (1) | IL202286A0 (enExample) |
| MX (1) | MX2009013205A (enExample) |
| WO (1) | WO2008154442A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8927546B2 (en) * | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| US7863266B2 (en) * | 2007-06-08 | 2011-01-04 | Helicon Therapeutics, Inc. | Therapeutic pyrazoloquinoline urea derivatives |
| EP2490692B1 (en) * | 2009-10-21 | 2016-11-16 | Merck Sharp & Dohme Corp. | Quinolinone-pyrazolone m1 receptor positive allosteric modulators |
| US9468662B2 (en) | 2010-07-12 | 2016-10-18 | Orphit | Use of the PAT nonapeptide in the treatment and prevention of neurodegenerative diseases |
| FR2962335B1 (fr) * | 2010-07-12 | 2013-01-18 | Cll Pharma | Utilisation du nonapeptide pat dans le traitement et la prevention des maladies neurodegeneratives |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| CN106187887B (zh) * | 2016-07-01 | 2018-08-14 | 上海工程技术大学 | 4-羟基喹啉-3-甲酸的制备方法 |
| PL3538512T3 (pl) | 2016-11-11 | 2021-11-22 | Bayer Animal Health Gmbh | Nowe pochodne chinolino-3-karboksyamidu o działaniu przeciw robakom pasożytniczym |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3068673D1 (en) * | 1979-06-21 | 1984-08-30 | Ciba Geigy Ag | Pyrazolo-quinolines, processes for their production, and pharmaceutical compositions containing them |
| DE3204126A1 (de) | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Pyrazoloxazine, -thiazine, -chinoline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4524146A (en) * | 1982-12-08 | 1985-06-18 | Ciba-Geigy Corporation | Certain -2-heterocycle substituted pyrazoloquinolines |
| US4814450A (en) * | 1984-07-09 | 1989-03-21 | Ciba-Geigy Corporation | Certain ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives |
| JPS61112075A (ja) * | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| EP0214092A1 (en) | 1985-08-08 | 1987-03-11 | Ciba-Geigy Ag | Enhanced absorption of psychoactive 2-aryl-pyrazolo quinolines as a solid molecular dispersion in polyvinylpyrrolidone |
| WO1992022552A1 (en) * | 1991-06-14 | 1992-12-23 | The Upjohn Company | IMIDAZO[1,5-a]QUINOXALINES |
| US5334595A (en) | 1992-10-23 | 1994-08-02 | Sterling Winthrop Inc. | Pyrazoloquinolones as anticancer agents |
| US5792766A (en) * | 1996-03-13 | 1998-08-11 | Neurogen Corporation | Imidazo 1,5-c! quinazolines; a new class of GABA brain receptor ligands |
| GB9716345D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9716344D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9716347D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| TWI271406B (en) | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| HUP0303270A3 (en) * | 2001-02-21 | 2007-03-28 | Janssen Pharmaceutica Nv | Isoxazoline derivatives as anti-depressants, process for their preparation and pharmaceutical compositions containing them |
| JP3896309B2 (ja) | 2001-07-09 | 2007-03-22 | ファイザー株式会社 | プロテインキナーゼｃ阻害物質としてのピラゾロキノリノン誘導体 |
| ATE425164T1 (de) * | 2002-12-16 | 2009-03-15 | Active Biotech Ab | Tetrazyklische immunmodulierende verbindungen |
| AR045689A1 (es) * | 2003-05-29 | 2005-11-09 | Millennium Pharm Inc | Compuestos derivados de 2,5-dihidro-pirazolo[4,3-c]quinolin-4-ona como inhibidores de chk-1 y composiciones farmaceuticas que los contienen |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| AU2006287378A1 (en) | 2005-09-07 | 2007-03-15 | Braincells, Inc. | Modulation of neurogenesis by HDac inhibition |
| US8173642B2 (en) * | 2005-10-25 | 2012-05-08 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivatives |
| ES2386168T3 (es) * | 2007-06-08 | 2012-08-10 | Helicon Therapeutics, Inc. | Derivados de pirazoloquinolina terapéuticos |
| US7863266B2 (en) * | 2007-06-08 | 2011-01-04 | Helicon Therapeutics, Inc. | Therapeutic pyrazoloquinoline urea derivatives |
| ES2483728T3 (es) * | 2007-06-08 | 2014-08-07 | Dart Neuroscience (Cayman) Ltd | Derivados terapéuticos de pirazolonafatiridina |
-
2008
- 2008-06-06 US US12/135,023 patent/US7863266B2/en not_active Expired - Fee Related
- 2008-06-06 EP EP08770406.0A patent/EP2164328B8/en not_active Not-in-force
- 2008-06-06 CA CA002688405A patent/CA2688405A1/en not_active Abandoned
- 2008-06-06 JP JP2010511389A patent/JP2010529144A/ja active Pending
- 2008-06-06 WO PCT/US2008/066205 patent/WO2008154442A1/en not_active Ceased
- 2008-06-06 BR BRPI0812347A patent/BRPI0812347A2/pt not_active IP Right Cessation
- 2008-06-06 CN CN200880023876A patent/CN101686682A/zh active Pending
- 2008-06-06 ES ES08770406T patent/ES2433566T3/es active Active
- 2008-06-06 AU AU2008261888A patent/AU2008261888A1/en not_active Abandoned
- 2008-06-06 KR KR1020107000233A patent/KR20100038189A/ko not_active Withdrawn
- 2008-06-06 MX MX2009013205A patent/MX2009013205A/es active IP Right Grant
-
2009
- 2009-11-23 IL IL202286A patent/IL202286A0/en unknown
-
2010
- 2010-11-29 US US12/955,792 patent/US8343957B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2164328B1 (en) | 2013-08-07 |
| EP2164328B8 (en) | 2013-09-11 |
| CN101686682A (zh) | 2010-03-31 |
| CA2688405A1 (en) | 2008-12-18 |
| EP2164328A4 (en) | 2010-06-23 |
| BRPI0812347A2 (pt) | 2016-08-02 |
| HK1142496A1 (en) | 2010-12-10 |
| IL202286A0 (en) | 2010-06-16 |
| MX2009013205A (es) | 2010-04-09 |
| US20110071140A1 (en) | 2011-03-24 |
| JP2010529144A (ja) | 2010-08-26 |
| KR20100038189A (ko) | 2010-04-13 |
| AU2008261888A1 (en) | 2008-12-18 |
| US8343957B2 (en) | 2013-01-01 |
| US7863266B2 (en) | 2011-01-04 |
| EP2164328A1 (en) | 2010-03-24 |
| US20080306048A1 (en) | 2008-12-11 |
| WO2008154442A1 (en) | 2008-12-18 |
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