CA2524900A1 - 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines - Google Patents
6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines Download PDFInfo
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- CA2524900A1 CA2524900A1 CA002524900A CA2524900A CA2524900A1 CA 2524900 A1 CA2524900 A1 CA 2524900A1 CA 002524900 A CA002524900 A CA 002524900A CA 2524900 A CA2524900 A CA 2524900A CA 2524900 A1 CA2524900 A1 CA 2524900A1
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- Prior art keywords
- alkyl
- group
- optionally substituted
- formula
- pyridyl
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- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003814 drug Substances 0.000 claims abstract 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- -1 cyano, amino Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 10
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 239000012442 inert solvent Substances 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 230000006735 deficit Effects 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 150000003254 radicals Chemical class 0.000 claims 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- OJWYYSVOSNWCCE-UHFFFAOYSA-N 2-methoxyethyl hypofluorite Chemical compound COCCOF OJWYYSVOSNWCCE-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 230000008447 perception Effects 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 230000019771 cognition Effects 0.000 abstract 1
- 0 *CC(N1)=Nc([n](*)nc2)c2C1=O Chemical compound *CC(N1)=Nc([n](*)nc2)c2C1=O 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—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
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to novel 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines, method for production and use thereof for the production of medicaments for the improvement of cognition, concentration, learning and/or memory capacity.
Claims (14)
1. Compounds of the formula in which R1 is C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C8-cycloalkyl, where C1-alkyl is optionally substituted by oxo, and where C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl and C3-C8-cycloalkyl are optionally substituted by up to 3 radicals independently of one another selected from the group of C1-C6-alkyl, C1-C6-alkoxy, hydroxycarbonyl, cyano, amino, nitro, hydroxy, C1-C6-alkylamino, halogen, trifluoromethyl, trifluoromethoxy, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, heteroarylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylsulphonyl, C1-C6-alkylthio, where C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, heteroarylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkyl-sulphonyl and C1-C6-alkylthio are optionally substituted by one to three radicals independently of one another selected from the group of hydroxy, cyano, halogen, trifluoromethyl, trifluoromethoxy, hydroxycarbonyl and a group of the formula -NR3R4, where R3 and R4 are independently of one another hydrogen or C1-C6-alkyl, or R3 and R4 together with the nitrogen atom to which they are bonded are 5- to 8-membered heterocyclyl, R2 is phenyl or heteroaryl, where phenyl is substituted by 1 to 3 radicals and heteroaryl is optionally substituted by 1 to 3 radicals in each case independently of one another selected from the group of C1-C6-alkyl, C1-C6-alkoxy, hydroxycarbonyl, cyano, trifluoromethyl, trifluoromethoxy, amino, nitro, hydroxy, C1-C6-alkylamino, halogen, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, heteroarylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylsulphonyl and C1-C6-alkylthio, where C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C6-C1o-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxy-carbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, hetero-arylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylsulphonyl and C1-C6-alkylthio are optionally substituted by one to three radicals independently of one another selected from the group of hydroxy, cyano, halogen, trifluoromethyl, trifluoromethoxy, hydroxycarbonyl and a group of the formula -NR3R4, where R3 and R4 have the meanings indicated above, and the salts, solvates and/or solvates of the salts thereof.
2. Compounds according to Claim 1, where R1 is C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C8-cycloalkyl, which are optionally substituted by up to 3 radicals independently of one another selected from the group of C1-C6-alkyl, C1-C6-alkoxy, hydroxycarbonyl, cyano, amino, nitro, hydroxy, C1-C6-alkylamino, halogen, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, heteroarylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylsulphonyl and C1-C6-alkylthio, where C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, heteroarylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylsulphonyl and C1-C6-alkylthio are optionally substituted by a radical selected from the group of hydroxy, cyano, halogen, hydroxycarbonyl and a group of the formula -NR3R4, where R3 and R4 are independently of one another hydrogen or C1-C6-alkyl, or R3 and R4 together with the nitrogen atom to which they are bonded are 5- to 8-membered heterocyclyl, R2 is phenyl or heteroaryl, where phenyl is substituted by 1 to 3 radicals and heteroaryl is optionally substituted by 1 to 3 radicals in each case independently of one another selected from the group of C1-C6-alkyl, C1-C6-alkoxy, hydroxycarbonyl, cyano, trifluoromethyl, amino, nitro, hydroxy, C1-C6-alkylamino, halogen, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylamino-carbonyl, C1-C6-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylamino-carbonyl, heteroarylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkyl-sulphonyl, C1-C6-alkylthio, where C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C6-C10-arylcarbonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylaminocarbonyl, C1-C6-alkoxy-carbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, hetero-arylcarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylsulphonyl and C1-C6-alkylthio are optionally substituted by a radical selected from the group of hydroxy, cyano, halogen, hydroxycarbonyl and a group of formula -NR3R4, where R3 and R4 have the meanings indicated above, and the salts, solvates and/or solvates of the salts thereof.
3. Compounds according to Claims 1 and 2, where R1 is C1-C5-alkyl or C3-C6-cycloalkyl, which are optionally substituted by up to 3 radicals independently of one another selected from the group of C1-C4-alkyl, C1-C4-alkoxy, hydroxycarbonyl, cyano, amino, hydroxy, C1-C4-alkylamino, tri-fluoromethyl, fluorine, chlorine, bromine, C6-C10-arylcarbonylamino, C1-C4-alkyl-carbonylamino, C1-C4-alkylaminocarbonyl, C1-C4-alkoxycarbonyl, C6-C10-aryl-aminocarbonyl, heteroarylaminocarbonyl, heteroarylcarbonylamino, C1-C4-alkyl-sulphonylamino, C1-C4-alkylsulphonyl, C1-C4-alkylthio, where C1-C4-alkyl and C1-C4-alkoxy are optionally substituted by a radical selected from the group of hydroxy, cyano, fluorine, chlorine, bromine, hydroxycarbonyl and a group of the formula -NR3R4, where R3 and R4 are independently hydrogen or C1-C4-alkyl, or R3 and R4 together with the nitrogen atom to which they are bonded are 5- to 6-membered heterocyclyl, R2 is phenyl, pyrimidyl, pyridyl N-oxide or pyridyl, where phenyl is substituted by 1 to 3 radicals and pyrimidyl, pyridyl N-oxide and pyridyl are optionally substituted by 1 to 3 radicals in each case independently of one another selected from the group of C1-C4-alkyl, C1-C4-alkoxy, hydroxycarbonyl, cyano, trifluoromethyl, amino, hydroxy, C1-C4-alkylamino, fluorine, chlorine, bromine, C6-C10-arylcarbonylamino, C1-C4-alkylcarbonylamino, C1-C4-alkylaminocarbonyl, C1-C4-alkoxycarbonyl, C6-C10-arylaminocarbonyl, heteroarylaminocarbonyl, heteroaryl-carbonylamino, C1-C4-alkylsulphonylamino, C1-C4-alkylsulphonyl, C1-C4-alkyl-thio, where C1-C4-alkyl and C1-C4-alkoxy are optionally substituted by a radical selected from the group of hydroxy, cyano, fluorine, chlorine, bromine, hydroxycarbonyl and a group of the formula -NR3R4, where R3 and R4 have the meanings indicated in Claim 1, and the salts, solvates and/or solvates of the salts thereof.
4. Compounds according to Claims 1 to 3, where R1 has the meanings indicated in Claims 1 to 3, and R2 is phenyl, pyridyl N-oxide or pyridyl, where phenyl is substituted by 1 to 3 radicals and pyridyl and pyridyl N-oxide are optionally substituted by 1 to 3 radicals in each case independently of one another selected from the group of methyl, ethyl, 2-propyl, trifluoromethyl, methoxy, ethoxy, fluorine and chlorine, and the salts, solvates and/or solvates of the salts thereof.
5. Compounds according to Claims 1 to 4, where R1 is C1-C5-alkyl or C5-C6-cycloalkyl, which are optionally substituted by up to 3 radicals independently of one another selected from the group of C1-C4-alkyl, trifluoromethyl, fluorine, hydroxy, phenylcarbonylamino, C1-C4-alkylcarbonyl-amino, C1-C4-alkylaminocarbonyl or phenylaminocarbonyl, and R2 is phenyl, pyridyl N-oxide or pyridyl, where phenyl is substituted by 1 to 3 radicals and pyridyl and pyridyl N-oxide are optionally substituted by 1 to 3 radicals in each case independently of one another selected from the group of methyl, ethyl, 2-propyl, trifluoromethyl, methoxy, ethoxy, fluorine and chlorine, and the salts, solvates and/or solvates of the salts thereof.
6. Compounds according to Claims 1 to 5, where R1 is C1-C5-alkyl or C5-C6-cycloalkyl, which are optionally substituted by up to 3 radicals independently of one another selected from the group of C1-C4-alkyl, fluorine, trifluoromethyl, hydroxy, phenylcarbonylamino, C1-C4-alkylcarbonyl-amino, C1-C4-alkylaminocarbonyl or phenylaminocarbonyl, and R2 is phenyl, pyridyl N-oxide or pyridyl, where phenyl is substituted by one radical and pyridyl and pyridyl N-oxide are optionally substituted by one radical in each case independently of one another selected from the group of methyl, ethyl, 2-propyl, trifluoromethyl, methoxy, ethoxy, fluorine and chlorine, and the salts, solvates and/or solvates of the salts thereof.
7. Process for preparing compounds according to Claim 1, characterized in that [A] compounds of the formula in which R2 has the meanings indicated in Claim 1, are converted by reaction with a compound of the formula in which R1 has the meanings indicated in Claim 1, and Z is chlorine or bromine, in an inert solvent and in the presence of a base, initially into compounds of the formula in which R1 and R2 have the meanings indicated in Claim 1, and then cyclized in an inert solvent in the presence of a base to compounds of the formula (I), or [B] compounds of the formula (II) are reacted with a compound of the formula in which R1 has the meanings indicated in Claim 1, and R5 is methyl or ethyl, in an inert solvent and in the presence of a base, with direct cyclization to (I), or [C] compounds of the formula in which R2 has the meanings indicated in Claim 1, are converted initially by reaction with a compound of the formula (IIIa) in an inert solvent and in the presence of a base into compounds of the formula in which R1 and R2 have the meanings indicated in Claim 1, and the latter are cyclized in a second step in an inert solvent and in the presence of a base and of an oxidizing agent to (I), and the resulting compounds of the formula (I) are where appropriate reacted with the appropriate (i) solvents and/or (ii) bases or acids to give their solvates, salts and/or solvates of the salts.
8. Compounds according to any of Claims 1 to 6 for the treatment and/or prophylaxis of diseases.
9. Medicament comprising at least one of the compounds according to any of Claims 1 to 6 and at least one pharmaceutically acceptable, essentially non-toxic carrier or excipient.
10. Use of the compounds according to any of Claims 1 to 6 for producing a medicament for the prophylaxis and/or treatment of impairments of perception, concentration, learning and/or memory.
11. Use according to Claim 10, where the impairment is a consequence of Alzheimer's disease.
12. Use of the compounds according to any of Claims 1 to 6 for producing a medicament for improving perception, concentration, learning and/or memory.
13. Method for controlling impairments of perception, concentration, learning and/or memory in humans or animals by administering an effective amount of compounds from Claims 1 to 6.
14. Method according to Claim 13, where the impairment is a consequence of Alzheimer's disease.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10320784.8 | 2003-05-09 | ||
| DE10320784 | 2003-05-09 | ||
| DE10336183 | 2003-08-07 | ||
| DE10336183.9 | 2003-08-07 | ||
| DE102004004142.3 | 2004-01-28 | ||
| DE102004004142A DE102004004142A1 (en) | 2003-05-09 | 2004-01-28 | 6-Cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines |
| PCT/EP2004/004455 WO2004099211A1 (en) | 2003-05-09 | 2004-04-28 | 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2524900A1 true CA2524900A1 (en) | 2004-11-18 |
| CA2524900C CA2524900C (en) | 2012-03-20 |
Family
ID=33436870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2524900A Expired - Fee Related CA2524900C (en) | 2003-05-09 | 2004-04-28 | 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1626971B1 (en) |
| JP (1) | JP2006525966A (en) |
| AU (1) | AU2004235915B2 (en) |
| CA (1) | CA2524900C (en) |
| UY (1) | UY28312A1 (en) |
| WO (1) | WO2004099211A1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8039477B2 (en) | 2002-08-23 | 2011-10-18 | Boehringer Ingelheim International Gmbh | Substituted pyrazolo[3,4-d]pyrimidin-4-one compounds as phosphodiesterase inhibitors |
| US8044060B2 (en) | 2003-05-09 | 2011-10-25 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory |
| US8158633B2 (en) | 2002-08-23 | 2012-04-17 | Boehringer Ingelheim International Gmbh | Phenyl-substituted pyrazolopyrimidines |
| US8455502B2 (en) | 2002-08-23 | 2013-06-04 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| US8623901B2 (en) | 2009-03-31 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US8623879B2 (en) | 2008-04-02 | 2014-01-07 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivates and their use as PDE9A modulators |
| US8648085B2 (en) | 2007-11-30 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-D) pyrimidin-4-one derivatives and their use as PDE9A mudulators for the treatment of CNS disorders |
| US8809348B2 (en) | 2003-05-09 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-arylmethyl substituted pyrazolo[3,4-d]pyrimidines |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US8912201B2 (en) | 2010-08-12 | 2014-12-16 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US9079905B2 (en) | 2008-09-08 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005024493A1 (en) * | 2005-05-27 | 2006-11-30 | Bayer Healthcare Ag | Use of pyrazolopyrimidines |
| TW201118099A (en) | 2009-08-12 | 2011-06-01 | Boehringer Ingelheim Int | New compounds for the treatment of CNS disorders |
| US20130040971A1 (en) * | 2011-02-14 | 2013-02-14 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of cns disorders |
| PL400149A1 (en) | 2012-07-26 | 2014-02-03 | Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia | Pyrazolo [3,4-d] pyrimidine-4 (5H) -one derivatives as PDE9 inhibitors |
| CN105744838B (en) * | 2013-05-28 | 2017-12-08 | 拜耳作物科学股份公司 | Heterocyclic compound as agricultural chemicals |
| TW201629064A (en) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | Triazolopyrainones as PDE1 inhibitors |
| JO3627B1 (en) | 2015-04-30 | 2020-08-27 | H Lundbeck As | Imidazopyrazinones as PDE1 inhibitors |
| TWI729109B (en) * | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 1,5-DIHYDRO-4H-PYRAZOLO[3,4-d]PYRIMIDIN-4-ONES AND 1,5-DIHYDRO-4H-PYRAZOLO[4,3-c]PYRIDIN-4-ONES AS PDE1 INHIBITORS |
| ES2967489T3 (en) | 2016-10-18 | 2024-04-30 | H Lundbeck As | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as PDE1 inhibitors |
| SG11201903770UA (en) | 2016-10-28 | 2019-05-30 | H Lundbeck As | Combination treatments comprising imidazopyrazinones for the treatment of psychiatric and/or cognitive disorders |
| WO2018078042A1 (en) | 2016-10-28 | 2018-05-03 | H. Lundbeck A/S | Combination treatments comprising administration of imidazopyrazinones |
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| CH396925A (en) * | 1960-05-11 | 1965-08-15 | Ciba Geigy | Process for the preparation of new pyrazolopyrimidines |
| DE1149013B (en) * | 1960-05-11 | 1963-05-22 | Ciba Geigy | Process for the preparation of 4-oxo-4, 5-dihydro-pyrazolo- [3, 4-d] pyrimidines |
| CA2417631A1 (en) * | 2000-08-01 | 2003-01-29 | Bayer Aktiengesellschaft | Selective pde 2 inhibitors, used as medicaments for improving cognition |
| HN2002000317A (en) * | 2001-11-02 | 2003-05-21 | Pfizer | PDE9 INHIBITORS FOR TREATMENT OF CARDIOVASCULAR DISORDERS |
| IL161155A0 (en) * | 2001-11-02 | 2004-08-31 | Pfizer Prod Inc | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
| DE10219435A1 (en) * | 2002-05-02 | 2003-11-13 | Bayer Cropscience Ag | Substituted pyrazolo-pyrimidin-4-ones |
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- 2004-04-28 EP EP04729876A patent/EP1626971B1/en not_active Expired - Lifetime
- 2004-04-28 WO PCT/EP2004/004455 patent/WO2004099211A1/en active Application Filing
- 2004-04-28 CA CA2524900A patent/CA2524900C/en not_active Expired - Fee Related
- 2004-04-28 AU AU2004235915A patent/AU2004235915B2/en not_active Ceased
- 2004-05-07 UY UY28312A patent/UY28312A1/en not_active Application Discontinuation
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8158633B2 (en) | 2002-08-23 | 2012-04-17 | Boehringer Ingelheim International Gmbh | Phenyl-substituted pyrazolopyrimidines |
| US8455502B2 (en) | 2002-08-23 | 2013-06-04 | Boehringer Ingelheim International Gmbh | Selective phosphodiesterase 9A inhibitors as medicaments for improving cognitive processes |
| US8741907B2 (en) | 2002-08-23 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Alkyl-substituted pyrazolopyrimidines |
| US8039477B2 (en) | 2002-08-23 | 2011-10-18 | Boehringer Ingelheim International Gmbh | Substituted pyrazolo[3,4-d]pyrimidin-4-one compounds as phosphodiesterase inhibitors |
| US8822479B2 (en) | 2003-05-09 | 2014-09-02 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl-and 6-alkylmethyl-substituted pyrazolepyrimidines |
| US8044060B2 (en) | 2003-05-09 | 2011-10-25 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory |
| US8809348B2 (en) | 2003-05-09 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-arylmethyl substituted pyrazolo[3,4-d]pyrimidines |
| US8648085B2 (en) | 2007-11-30 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-D) pyrimidin-4-one derivatives and their use as PDE9A mudulators for the treatment of CNS disorders |
| US9096603B2 (en) | 2008-04-02 | 2015-08-04 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivatives and their use as PDE9A modulators |
| US8623879B2 (en) | 2008-04-02 | 2014-01-07 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1,5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivates and their use as PDE9A modulators |
| US9079905B2 (en) | 2008-09-08 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US8623901B2 (en) | 2009-03-31 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US9102679B2 (en) | 2009-03-31 | 2015-08-11 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of CNS disorders |
| US8912201B2 (en) | 2010-08-12 | 2014-12-16 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US9328120B2 (en) | 2010-08-12 | 2016-05-03 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006525966A (en) | 2006-11-16 |
| EP1626971A1 (en) | 2006-02-22 |
| AU2004235915B2 (en) | 2010-08-05 |
| EP1626971B1 (en) | 2011-08-10 |
| CA2524900C (en) | 2012-03-20 |
| UY28312A1 (en) | 2004-12-31 |
| AU2004235915A1 (en) | 2004-11-18 |
| WO2004099211A1 (en) | 2004-11-18 |
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