ES2635016T3 - Nuevos compuestos como inhibidores duales de fosfodiesterasas e histonas deacetilasas - Google Patents
Nuevos compuestos como inhibidores duales de fosfodiesterasas e histonas deacetilasas Download PDFInfo
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- ES2635016T3 ES2635016T3 ES14707155.9T ES14707155T ES2635016T3 ES 2635016 T3 ES2635016 T3 ES 2635016T3 ES 14707155 T ES14707155 T ES 14707155T ES 2635016 T3 ES2635016 T3 ES 2635016T3
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- RPZAAFUKDPKTKP-UHFFFAOYSA-N n-(methoxymethyl)-1-phenyl-n-(trimethylsilylmethyl)methanamine Chemical compound COCN(C[Si](C)(C)C)CC1=CC=CC=C1 RPZAAFUKDPKTKP-UHFFFAOYSA-N 0.000 description 1
- PSQIKSBMRFTURW-UHFFFAOYSA-N n-[1-[3-(2-ethoxyphenyl)-5-oxo-2h-1,2,4-triazin-6-yl]ethyl]butanamide Chemical compound N1C(=O)C(C(C)NC(=O)CCC)=NN=C1C1=CC=CC=C1OCC PSQIKSBMRFTURW-UHFFFAOYSA-N 0.000 description 1
- NWFWICZZNFIXLC-UHFFFAOYSA-N n-[4-[4-[3-(2-morpholin-4-ylethylamino)-4-nitrophenyl]piperazin-1-yl]sulfonylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)N1CCN(C=2C=C(NCCN3CCOCC3)C(=CC=2)[N+]([O-])=O)CC1 NWFWICZZNFIXLC-UHFFFAOYSA-N 0.000 description 1
- CCBCHURBDSNSTJ-UHFFFAOYSA-N n-hydroxybutanamide Chemical compound CCCC(=O)NO CCBCHURBDSNSTJ-UHFFFAOYSA-N 0.000 description 1
- UJWWRLYXVMPKEU-UHFFFAOYSA-N n-hydroxycyclopentanecarboxamide Chemical compound ONC(=O)C1CCCC1 UJWWRLYXVMPKEU-UHFFFAOYSA-N 0.000 description 1
- HQVFKSDWNYVAQD-UHFFFAOYSA-N n-hydroxyprop-2-enamide Chemical compound ONC(=O)C=C HQVFKSDWNYVAQD-UHFFFAOYSA-N 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 230000006764 neuronal dysfunction Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QXAHJILNWYDAIV-UHFFFAOYSA-N o-ethyl 4-chloro-2-methylpyrimidine-5-carbothioate Chemical compound CCOC(=S)C1=CN=C(C)N=C1Cl QXAHJILNWYDAIV-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- CMXVPHSHKFQSHM-UHFFFAOYSA-N oxan-4-ylhydrazine Chemical compound NNC1CCOCC1 CMXVPHSHKFQSHM-UHFFFAOYSA-N 0.000 description 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 238000001243 protein synthesis Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- DAPAQENNNINUPW-IDAMAFBJSA-N rocaglamide Chemical compound C1=CC(OC)=CC=C1[C@]1([C@@H]([C@H]([C@H]2O)C(=O)N(C)C)C=3C=CC=CC=3)[C@]2(O)C2=C(OC)C=C(OC)C=C2O1 DAPAQENNNINUPW-IDAMAFBJSA-N 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YGTVAFAQOVALDB-UHFFFAOYSA-N tert-butyl 2-propyloctanoate Chemical compound CCCCCCC(CCC)C(=O)OC(C)(C)C YGTVAFAQOVALDB-UHFFFAOYSA-N 0.000 description 1
- RDUYKRRKWMUWJG-JXMROGBWSA-N tert-butyl 3-[4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenoxy]azetidine-1-carboxylate Chemical compound COC(/C=C/C1=CC=C(OC2CN(C2)C(=O)OC(C)(C)C)C=C1)=O RDUYKRRKWMUWJG-JXMROGBWSA-N 0.000 description 1
- DJFIHJKYILFNSO-UHFFFAOYSA-N tert-butyl 4-(3-methoxycarbonylphenoxy)piperidine-1-carboxylate Chemical compound COC(=O)C1=CC=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=C1 DJFIHJKYILFNSO-UHFFFAOYSA-N 0.000 description 1
- UKCBGXCNXOKVTF-UHFFFAOYSA-N tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC=C(Br)C=N1 UKCBGXCNXOKVTF-UHFFFAOYSA-N 0.000 description 1
- CTEDVGRUGMPBHE-UHFFFAOYSA-N tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CO)CC1 CTEDVGRUGMPBHE-UHFFFAOYSA-N 0.000 description 1
- OLVVYDHFUSZRBC-UHFFFAOYSA-N tert-butyl 4-[[3-[(5-carbamoyl-1-methyl-3-propylpyrazol-4-yl)carbamoyl]phenoxy]methyl]piperidine-1-carboxylate Chemical compound C(N)(=O)C1=C(C(=NN1C)CCC)NC(=O)C=1C=C(OCC2CCN(CC2)C(=O)OC(C)(C)C)C=CC=1 OLVVYDHFUSZRBC-UHFFFAOYSA-N 0.000 description 1
- LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
- JYUQEWCJWDGCRX-UHFFFAOYSA-N tert-butyl 4-formylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)CC1 JYUQEWCJWDGCRX-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- PDTZMULNKGUIEJ-UHFFFAOYSA-N tert-butyl 4-methylidenepiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=C)CC1 PDTZMULNKGUIEJ-UHFFFAOYSA-N 0.000 description 1
- WOEQSXAIPTXOPY-UHFFFAOYSA-N tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 WOEQSXAIPTXOPY-UHFFFAOYSA-N 0.000 description 1
- NVIWXGKUOOJQBZ-UHFFFAOYSA-N tert-butyl n-[1-(5-bromopyrimidin-2-yl)piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=NC=C(Br)C=N1 NVIWXGKUOOJQBZ-UHFFFAOYSA-N 0.000 description 1
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
- NESCAWUERMKVNG-UHFFFAOYSA-N tert-butyl-[(4-chloro-2-methylsulfanylpyrimidin-5-yl)methoxy]-dimethylsilane Chemical compound C(C)(C)(C)[Si](C)(C)OCC=1C(=NC(=NC=1)SC)Cl NESCAWUERMKVNG-UHFFFAOYSA-N 0.000 description 1
- KYAVKEQBQWBXSI-UHFFFAOYSA-N tert-butyl-dimethyl-[(2-methylsulfanylpyrimidin-5-yl)methoxy]silane Chemical compound C(C)(C)(C)[Si](OCC=1C=NC(=NC=1)SC)(C)C KYAVKEQBQWBXSI-UHFFFAOYSA-N 0.000 description 1
- GRIFNKNAEPIXKH-UHFFFAOYSA-N tert-butyl-dimethyl-[(2-methylsulfonylpyrimidin-5-yl)methoxy]silane Chemical compound C(C)(C)(C)[Si](OCC=1C=NC(=NC=1)S(=O)(=O)C)(C)C GRIFNKNAEPIXKH-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
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- BMDAASXALYXZSG-UHFFFAOYSA-M zinc;ethyl acetate;bromide Chemical compound Br[Zn+].CCOC([CH2-])=O BMDAASXALYXZSG-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- C07D487/04—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
- A61K31/495—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- 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
-
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13382065 | 2013-03-01 | ||
| EP13382065 | 2013-03-01 | ||
| PCT/EP2014/053877 WO2014131855A1 (en) | 2013-03-01 | 2014-02-27 | Novel compounds as dual inhibitors of phosphodiesterases and histone deacetylases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2635016T3 true ES2635016T3 (es) | 2017-10-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14707155.9T Active ES2635016T3 (es) | 2013-03-01 | 2014-02-27 | Nuevos compuestos como inhibidores duales de fosfodiesterasas e histonas deacetilasas |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9573956B2 (enExample) |
| EP (1) | EP2961741B1 (enExample) |
| JP (1) | JP6338601B2 (enExample) |
| CA (1) | CA2908482A1 (enExample) |
| DK (1) | DK2961741T3 (enExample) |
| ES (1) | ES2635016T3 (enExample) |
| WO (1) | WO2014131855A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9505767B2 (en) * | 2013-09-05 | 2016-11-29 | Genentech, Inc. | Pyrazolo[1,5-A]pyrimidin-7(4H)-onehistone demethylase inhibitors |
| EP3085700B1 (en) * | 2013-12-20 | 2018-10-31 | Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China | Novel piperidine carboxamide compound, preparation method, and usage thereof |
| CA2987978C (en) * | 2014-06-16 | 2022-08-16 | Fundacion Para La Investigacion Medica Aplicada | Novel compounds as dual inhibitors of histone methyltransferases and dna methyltransferases |
| JP2017523204A (ja) * | 2014-08-04 | 2017-08-17 | ファンダシオン パラ ラ インベスティガシオン メディカ アプリカダFundacion Para La Investigasion Medica Aplicada | 認知向上のために用いる新規化合物 |
| WO2016120432A1 (en) * | 2015-01-30 | 2016-08-04 | Fundación Para La Investigación Médica Aplicada | Compounds and methods for anticoagulation therapy |
| CN104610166B (zh) * | 2015-03-10 | 2017-06-13 | 山东大学 | 嘧啶苄基异羟肟酸类组蛋白去乙酰化酶抑制剂及制备方法和应用 |
| HK1249104A1 (zh) | 2015-03-13 | 2018-10-26 | Forma Therapeutics, Inc. | 作为HDAC8抑制剂的α-肉桂酰胺化合物和组合物 |
| KR102457316B1 (ko) * | 2015-06-26 | 2022-10-20 | 총킹 디캉 에릴 파마 씨오. 엘티디. | 새로운 5형포스포디에스테라아제 억제제 및 그 용도 |
| CN110337437B (zh) | 2016-12-28 | 2023-02-03 | 达特神经科学有限公司 | 作为pde2抑制剂的取代的吡唑并嘧啶酮化合物 |
| CN107163052B (zh) * | 2017-04-18 | 2020-08-11 | 华南农业大学 | 一种针对多种pde-5抑制剂药物的免疫检测方法 |
| WO2019018562A1 (en) | 2017-07-19 | 2019-01-24 | Ideaya Biosciences, Inc. | AMIDO COMPOUND AS MODULATORS OF AHR |
| CN108912029B (zh) * | 2017-08-25 | 2021-10-01 | 广东东阳光药业有限公司 | 含氮杂环酰胺衍生物及其用途 |
| KR102794907B1 (ko) | 2017-11-27 | 2025-04-14 | 다트 뉴로사이언스, 엘엘씨 | Pde1 억제제로서의 치환된 푸라노피리미딘 화합물 |
| CN110054625B (zh) * | 2018-01-18 | 2022-01-07 | 山东大学 | N-酰基苯磺酰胺异羟肟酸类Bcl-2、HDAC双靶点抑制剂及制备方法和应用 |
| CN108558890A (zh) * | 2018-06-28 | 2018-09-21 | 重庆康刻尔制药有限公司 | 一种西地那非中间体合成方法 |
| CN109824516B (zh) * | 2019-03-14 | 2021-07-23 | 泰州精英化成医药科技有限公司 | 一种反式-4-羟基环已烷甲酸叔丁酯的制备方法 |
| CN109810108B (zh) * | 2019-03-20 | 2021-08-06 | 华东理工大学 | 2,8-二氮杂-螺-[4,5]-癸烷类嘧啶-异羟肟酸化合物及其用途 |
| US11787812B2 (en) | 2020-12-11 | 2023-10-17 | Ildong Pharmaceutical Co., Ltd. | Substituted pyrazolo[4,3-d]pyrimidines and imidazo[5,1 -f][1,2,4]triazines as androgen receptor and phosphodiesterase dual inhibitors |
| KR20240124952A (ko) | 2021-12-22 | 2024-08-19 | 어거스틴 테라퓨틱스 | Hdac6 억제제로서의 화합물 및 이의 용도 |
| CN115417877B (zh) * | 2022-09-20 | 2024-05-14 | 杭州师范大学 | 组蛋白去乙酰化酶抑制剂及其制备和在制备抗癌症药物上的应用 |
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|---|---|---|---|---|
| AU2003210447B2 (en) * | 2002-01-04 | 2008-02-07 | Henry Ford Health System | Nitric oxide donors for treatment of disease and injury |
| CN1548438A (zh) * | 2003-05-16 | 2004-11-24 | 烟台开发区北方药物研究所 | 2-取代苯基-6,8-二烃基-3H-咪唑[1,5α][1,3,5]三嗪-4-酮衍生物,其制备方法及其药物用途 |
| DE602005017135D1 (de) * | 2004-03-05 | 2009-11-26 | Nycomed Gmbh | Neue verwendung von pde5-hemmern |
| CA2661483A1 (en) * | 2006-08-24 | 2008-02-28 | Surface Logix, Inc. | Pharmacokinetically improved 2-phenyl-substituted imidazotriazinone derivatives and their use |
| EP2061772A4 (en) * | 2006-09-11 | 2011-06-29 | Curis Inc | MULTIFUNCTIONAL SMALL MOLECULES AS PROLIFERATION-ACTIVE ACTIVE SUBSTANCES |
| JP2010527928A (ja) * | 2007-05-18 | 2010-08-19 | ヴィヴァス・インコーポレイテッド | ホスホジエステラーゼ−5阻害剤を含む新規の組み合わせおよびそれらの使用 |
| NZ603725A (en) * | 2010-08-12 | 2015-04-24 | Boehringer Ingelheim Int | 6-cycloalkyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors |
| EP2535049A1 (en) * | 2011-06-17 | 2012-12-19 | Proyecto de Biomedicina Cima, S.L. | Tadalafil for the treatment of dementia |
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- 2014-02-27 CA CA2908482A patent/CA2908482A1/en not_active Abandoned
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- 2014-02-27 WO PCT/EP2014/053877 patent/WO2014131855A1/en not_active Ceased
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| EP2961741A1 (en) | 2016-01-06 |
| EP2961741B1 (en) | 2017-04-05 |
| US20160002246A1 (en) | 2016-01-07 |
| WO2014131855A9 (en) | 2014-11-13 |
| JP6338601B2 (ja) | 2018-06-06 |
| JP2016513130A (ja) | 2016-05-12 |
| CA2908482A1 (en) | 2014-09-04 |
| DK2961741T3 (en) | 2017-07-03 |
| US9573956B2 (en) | 2017-02-21 |
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