NO312297B1 - Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament - Google Patents

Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament Download PDF

Info

Publication number: NO312297B1
Authority: NO; Norway
Prior art keywords: benzenesulfonyl; pyrazolo; methyl; methylsulfanyl; pyrimidine
Prior art date: 1998-03-11

Application number

NO19991150A

Other languages

English (en)

Norwegian (no)

Other versions

NO991150L (no

NO991150D0 (no

Inventor

Michael Boes

Claus Riemer

Heinz Stadler

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1998-03-11

Filing date

1999-03-10

Publication date

2002-04-22

1999-03-10 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1999-03-10 Publication of NO991150D0 publication Critical patent/NO991150D0/no

1999-09-13 Publication of NO991150L publication Critical patent/NO991150L/no

2002-04-22 Publication of NO312297B1 publication Critical patent/NO312297B1/no

Links

239000003814 drug Substances 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 10
229940079593 drug Drugs 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 8
APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
PEYVWBGHBCDXRT-UHFFFAOYSA-N N1=NNC2=CN=NC2=C1 Chemical class N1=NNC2=CN=NC2=C1 PEYVWBGHBCDXRT-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 64
-1 di-lower-alkyl-amino Chemical group 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 23
208000024827 Alzheimer disease Diseases 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 7
208000026139 Memory disease Diseases 0.000 claims description 7
208000012902 Nervous system disease Diseases 0.000 claims description 7
208000025966 Neurological disease Diseases 0.000 claims description 7
208000018737 Parkinson disease Diseases 0.000 claims description 7
208000028017 Psychotic disease Diseases 0.000 claims description 7
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
201000000980 schizophrenia Diseases 0.000 claims description 7
MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 6
208000020925 Bipolar disease Diseases 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
208000020401 Depressive disease Diseases 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
VFCWRGUKFKHOAB-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C VFCWRGUKFKHOAB-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
CCEJDZJFMKQICA-UHFFFAOYSA-N 10-(benzenesulfonyl)-11-ethyl-2-piperazin-1-yl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(CC)=NN2C=1N1CCNCC1 CCEJDZJFMKQICA-UHFFFAOYSA-N 0.000 claims description 3
UDOLYSWYIJXJRX-UHFFFAOYSA-N 10-(benzenesulfonyl)-2-(4-methylpiperazin-1-yl)-11-methylsulfanyl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 UDOLYSWYIJXJRX-UHFFFAOYSA-N 0.000 claims description 3
WEUOAFDJWUMTLR-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-5-yl]oxyethanol Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(OCCO)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WEUOAFDJWUMTLR-UHFFFAOYSA-N 0.000 claims description 3
LVVLVQQEHHNMTM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 LVVLVQQEHHNMTM-UHFFFAOYSA-N 0.000 claims description 3
IOMUIPHNKVJREA-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 IOMUIPHNKVJREA-UHFFFAOYSA-N 0.000 claims description 3
LCERYWUKXGPGNQ-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 LCERYWUKXGPGNQ-UHFFFAOYSA-N 0.000 claims description 3
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NBTJXYKEPGRADD-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NBTJXYKEPGRADD-UHFFFAOYSA-N 0.000 claims description 3
SRMFGSKGKUHKCH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 SRMFGSKGKUHKCH-UHFFFAOYSA-N 0.000 claims description 3
ACAVEAGQNALEAY-UHFFFAOYSA-N 3-benzenesulphonyl-2-methylsulphanyl-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-8-ylamine Chemical compound CSC1=NN2C(N)=C3CCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 ACAVEAGQNALEAY-UHFFFAOYSA-N 0.000 claims description 3
WTLHPKQGVWVPFJ-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(N)N4N=C3SC)=CC=C21 WTLHPKQGVWVPFJ-UHFFFAOYSA-N 0.000 claims description 3
HCYCQIRHCHFSLZ-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-7-piperazin-1-yl-3-thiophen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CS1 HCYCQIRHCHFSLZ-UHFFFAOYSA-N 0.000 claims description 3
PNYWTBNVJKJDDI-UHFFFAOYSA-N 8-(benzenesulfonyl)-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound CSC1=NN2C(N)=NC=NC2=C1S(=O)(=O)C1=CC=CC=C1 PNYWTBNVJKJDDI-UHFFFAOYSA-N 0.000 claims description 3
UJZYDAYPPURDES-UHFFFAOYSA-N C=12CSCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 Chemical compound C=12CSCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 UJZYDAYPPURDES-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
PPPVADQGCXVIIG-UHFFFAOYSA-N chembl1642114 Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 PPPVADQGCXVIIG-UHFFFAOYSA-N 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
MZHLYLPLUQNPRH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,6-dimethyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CC=1C(C)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 MZHLYLPLUQNPRH-UHFFFAOYSA-N 0.000 claims description 2
CJYVLEUNNDIHSZ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(methoxymethyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-6-amine Chemical compound CSC1=NN2C=C(N)C(COC)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CJYVLEUNNDIHSZ-UHFFFAOYSA-N 0.000 claims description 2
KHHFVHLOIOOBGE-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KHHFVHLOIOOBGE-UHFFFAOYSA-N 0.000 claims description 2
GQNCJZJRMRMGDJ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-n,5-n-dimethyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CSC1=NN2C(N)=CC(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 GQNCJZJRMRMGDJ-UHFFFAOYSA-N 0.000 claims description 2
RPYDLZZCQDDXIB-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-3-(4-propan-2-ylphenyl)sulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)C)C=C1 RPYDLZZCQDDXIB-UHFFFAOYSA-N 0.000 claims description 2
FBXQGDKVKMTEAF-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C FBXQGDKVKMTEAF-UHFFFAOYSA-N 0.000 claims description 2
OWSYFTNTDMXBFQ-UHFFFAOYSA-N 5-methyl-3-(3-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC(C)=C1 OWSYFTNTDMXBFQ-UHFFFAOYSA-N 0.000 claims description 2
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
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LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
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SVYCFYNZKMXSEU-UHFFFAOYSA-N n,5-dimethyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(NC)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 SVYCFYNZKMXSEU-UHFFFAOYSA-N 0.000 description 1
MCVKRCNWTSRZKG-UHFFFAOYSA-N n,n,5-trimethyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(N4N=C3SC)N(C)C)=CC=C21 MCVKRCNWTSRZKG-UHFFFAOYSA-N 0.000 description 1
XONFMUICYNIBEQ-UHFFFAOYSA-N n,n,5-trimethyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 XONFMUICYNIBEQ-UHFFFAOYSA-N 0.000 description 1
SGTHBUSRDBXVCQ-UHFFFAOYSA-N n-[3-(4-bromophenyl)sulfonyl-2-ethyl-5-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=NN2C(NCCN(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 SGTHBUSRDBXVCQ-UHFFFAOYSA-N 0.000 description 1
NNKXIULLHBGRTD-UHFFFAOYSA-N n-[3-(benzenesulfonyl)-2-ethyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(NCCN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NNKXIULLHBGRTD-UHFFFAOYSA-N 0.000 description 1
KGSMVKIWXJCCQV-UHFFFAOYSA-N n-[3-(benzenesulfonyl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CSC1=NN2C(NCCN(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KGSMVKIWXJCCQV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229960001779 pargyline Drugs 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
KCVNFNZJAATRIK-UHFFFAOYSA-M sodium;pyridine-3-sulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CN=C1 KCVNFNZJAATRIK-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
KQWHKLZRDFJOCN-UHFFFAOYSA-N thieno[3,4-d]pyrimidine Chemical compound N1=CN=CC2=CSC=C21 KQWHKLZRDFJOCN-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 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
- 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
- A61P25/24—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Psychology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO19991150A 1998-03-11 1999-03-10 Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament NO312297B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98104346		1998-03-11

Publications (3)

Publication Number	Publication Date
NO991150D0 NO991150D0 (no)	1999-03-10
NO991150L NO991150L (no)	1999-09-13
NO312297B1 true NO312297B1 (no)	2002-04-22

Family

ID=8231568

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19991150A NO312297B1 (no)	1998-03-11	1999-03-10	Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament

Country Status (33)

Country	Link
US (1)	US6194410B1 (es)
EP (1)	EP0941994B1 (es)
JP (1)	JP3231288B2 (es)
KR (1)	KR100313181B1 (es)
CN (1)	CN1118468C (es)
AR (1)	AR016453A1 (es)
AT (1)	ATE240332T1 (es)
AU (1)	AU752408B2 (es)
BR (1)	BR9901095A (es)
CA (1)	CA2265095C (es)
CZ (1)	CZ291514B6 (es)
DE (1)	DE69907784T2 (es)
DK (1)	DK0941994T3 (es)
ES (1)	ES2198095T3 (es)
HR (1)	HRP990077B1 (es)
HU (1)	HUP9900589A1 (es)
ID (1)	ID23575A (es)
IL (1)	IL128869A (es)
MA (1)	MA26612A1 (es)
MY (1)	MY119536A (es)
NO (1)	NO312297B1 (es)
NZ (1)	NZ334526A (es)
PE (1)	PE20000337A1 (es)
PL (1)	PL331875A1 (es)
PT (1)	PT941994E (es)
RU (1)	RU2218340C2 (es)
SG (1)	SG78336A1 (es)
SI (1)	SI0941994T1 (es)
TR (1)	TR199900531A3 (es)
TW (1)	TW585865B (es)
UY (1)	UY25419A1 (es)
YU (1)	YU12099A (es)
ZA (1)	ZA991946B (es)

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1999
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- 1999-03-10 CZ CZ1999825A patent/CZ291514B6/cs not_active IP Right Cessation
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Also Published As

Publication number	Publication date
HRP990077A2 (en)	2000-02-29
CA2265095C (en)	2008-07-22
EP0941994B1 (en)	2003-05-14
DE69907784D1 (de)	2003-06-18
SG78336A1 (en)	2001-02-20
CN1118468C (zh)	2003-08-20
SI0941994T1 (en)	2003-10-31
AU752408B2 (en)	2002-09-19
BR9901095A (pt)	2000-05-02
TR199900531A2 (xx)	1999-10-21
UY25419A1 (es)	2001-11-30
NO991150L (no)	1999-09-13
PE20000337A1 (es)	2000-05-13
TW585865B (en)	2004-05-01
CN1236780A (zh)	1999-12-01
ZA991946B (en)	1999-09-13
JP3231288B2 (ja)	2001-11-19
IL128869A (en)	2003-09-17
KR19990077741A (ko)	1999-10-25
CZ82599A3 (cs)	1999-09-15
MA26612A1 (fr)	2004-12-20
NO991150D0 (no)	1999-03-10
TR199900531A3 (tr)	1999-10-21
IL128869A0 (en)	2000-01-31
KR100313181B1 (ko)	2001-11-05
PT941994E (pt)	2003-09-30
EP0941994A1 (en)	1999-09-15
HK1023343A1 (en)	2000-09-08
ID23575A (id)	2000-05-04
HUP9900589A1 (hu)	2000-03-28
JP2000186090A (ja)	2000-07-04
MY119536A (en)	2005-06-30
CA2265095A1 (en)	1999-09-11
PL331875A1 (en)	1999-09-13
DE69907784T2 (de)	2004-03-25
HRP990077B1 (en)	2003-08-31
AR016453A1 (es)	2001-07-04
RU2218340C2 (ru)	2003-12-10
NZ334526A (en)	2000-07-28
YU12099A (sh)	2000-10-30
HU9900589D0 (en)	1999-05-28
AU2038399A (en)	1999-09-23
US6194410B1 (en)	2001-02-27
ES2198095T3 (es)	2004-01-16
CZ291514B6 (cs)	2003-03-12
DK0941994T3 (da)	2003-09-08
ATE240332T1 (de)	2003-05-15

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