CA2351488C - Substituted 4-amino-2-arylcyclopenta[d]pyrimidines, their preparation, their use and pharmaceutical preparations comprising them - Google Patents
Substituted 4-amino-2-arylcyclopenta[d]pyrimidines, their preparation, their use and pharmaceutical preparations comprising them Download PDFInfo
- Publication number
- CA2351488C CA2351488C CA002351488A CA2351488A CA2351488C CA 2351488 C CA2351488 C CA 2351488C CA 002351488 A CA002351488 A CA 002351488A CA 2351488 A CA2351488 A CA 2351488A CA 2351488 C CA2351488 C CA 2351488C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- substituted
- pyrimidine
- cyclopenta
- dihydro
- 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.)
- Expired - Fee Related
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000003230 pyrimidines Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 238000011321 prophylaxis Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 5
- 206010020772 Hypertension Diseases 0.000 claims abstract description 5
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 4
- 206010019280 Heart failures Diseases 0.000 claims abstract description 4
- -1 4-hydroxycyclohexyl Chemical group 0.000 claims description 89
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims description 22
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 238000002560 therapeutic procedure Methods 0.000 claims description 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YFFIDZJIZDLWDB-WKILWMFISA-N C1=CC(C)=CC=C1C(N=C1N[C@@H]2CC[C@@H](O)CC2)=NC2=C1CCC2 Chemical compound C1=CC(C)=CC=C1C(N=C1N[C@@H]2CC[C@@H](O)CC2)=NC2=C1CCC2 YFFIDZJIZDLWDB-WKILWMFISA-N 0.000 claims description 3
- UYSQYXCWLRFPRE-SHTZXODSSA-N C1C[C@@H](O)CC[C@@H]1NC1=NC(C=2C=CC(Cl)=CC=2)=NC2=C1CCC2 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=NC(C=2C=CC(Cl)=CC=2)=NC2=C1CCC2 UYSQYXCWLRFPRE-SHTZXODSSA-N 0.000 claims description 3
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- WUFCJZLKDBWTBT-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-(3-methoxypropyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCOC)=NC=1C1=CC=C(OC)C(OC)=C1 WUFCJZLKDBWTBT-UHFFFAOYSA-N 0.000 claims description 2
- MDLRUXNZLBAKEZ-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-n-(pyridin-3-ylmethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC(Cl)=CC(C=2N=C(NCC=3C=NC=CC=3)C=3CCCC=3N=2)=C1 MDLRUXNZLBAKEZ-UHFFFAOYSA-N 0.000 claims description 2
- KNMVHYWDSWWOKN-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(pyridin-3-ylmethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(C=2N=C(NCC=3C=NC=CC=3)C=3CCCC=3N=2)=C1 KNMVHYWDSWWOKN-UHFFFAOYSA-N 0.000 claims description 2
- XRTIEINWNWWLLV-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-cyclopentyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(C=2N=C(NC3CCCC3)C=3CCCC=3N=2)=C1 XRTIEINWNWWLLV-UHFFFAOYSA-N 0.000 claims description 2
- WZWVYYXJHMVYNN-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(2-methylpropyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCC(C)C)=NC=1C1=CC=C(Cl)C=C1 WZWVYYXJHMVYNN-UHFFFAOYSA-N 0.000 claims description 2
- NDHSLSZOESUPPN-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-cyclopentyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 NDHSLSZOESUPPN-UHFFFAOYSA-N 0.000 claims description 2
- VNYUDZMBULFXAH-UHFFFAOYSA-N 2-[[2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]ethanol Chemical compound C1=CC(C)=CC=C1C(N=C1NCCO)=NC2=C1CCC2 VNYUDZMBULFXAH-UHFFFAOYSA-N 0.000 claims description 2
- ASALTPIJADNPFQ-UHFFFAOYSA-N 3-[[2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C(N=C1NCCCO)=NC2=C1CCC2 ASALTPIJADNPFQ-UHFFFAOYSA-N 0.000 claims description 2
- LAXAXXLEFJERMU-UHFFFAOYSA-N 4-[4-(3-methoxypropylamino)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl]benzonitrile Chemical compound N=1C=2CCCC=2C(NCCCOC)=NC=1C1=CC=C(C#N)C=C1 LAXAXXLEFJERMU-UHFFFAOYSA-N 0.000 claims description 2
- JUTHAFDLHUNZBH-UHFFFAOYSA-N 4-[4-(benzylamino)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(N=C1NCC=2C=CC=CC=2)=NC2=C1CCC2 JUTHAFDLHUNZBH-UHFFFAOYSA-N 0.000 claims description 2
- JSNYFSFWTAUTFR-UHFFFAOYSA-N 4-[4-(pyridin-3-ylmethylamino)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(N=C1NCC=2C=NC=CC=2)=NC2=C1CCC2 JSNYFSFWTAUTFR-UHFFFAOYSA-N 0.000 claims description 2
- ISSVEEMYWVLUBE-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]butan-1-ol Chemical compound N=1C=2CCCC=2C(NCCCCO)=NC=1C1=CC(Cl)=CC(Cl)=C1 ISSVEEMYWVLUBE-UHFFFAOYSA-N 0.000 claims description 2
- 206010052337 Diastolic dysfunction Diseases 0.000 claims description 2
- 208000011514 Familial renal glucosuria Diseases 0.000 claims description 2
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- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 2
- MEVSBTPHUHIQMQ-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1NCCC=2C(=CC=CC=2)Cl)=NC2=C1CCC2 MEVSBTPHUHIQMQ-UHFFFAOYSA-N 0.000 claims description 2
- HXKXDHGVMNKZKN-UHFFFAOYSA-N n-butyl-2-(3,4-dimethoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(OC)C(OC)=C1 HXKXDHGVMNKZKN-UHFFFAOYSA-N 0.000 claims description 2
- BMQFHIMGDYQPLP-UHFFFAOYSA-N n-butyl-2-(3,5-dichlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC(Cl)=CC(Cl)=C1 BMQFHIMGDYQPLP-UHFFFAOYSA-N 0.000 claims description 2
- RMEBDWFOJDIDCG-UHFFFAOYSA-N n-butyl-2-(4-chlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(Cl)C=C1 RMEBDWFOJDIDCG-UHFFFAOYSA-N 0.000 claims description 2
- XBTOUXZSDWFOJV-UHFFFAOYSA-N n-butyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(OC)C=C1 XBTOUXZSDWFOJV-UHFFFAOYSA-N 0.000 claims description 2
- YLOXCZMZUXEPAK-UHFFFAOYSA-N n-butyl-2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(C)C=C1 YLOXCZMZUXEPAK-UHFFFAOYSA-N 0.000 claims description 2
- XKNJKKXCPOGINE-UHFFFAOYSA-N n-cyclohexyl-2-(3,4-dimethoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(N=C1NC2CCCCC2)=NC2=C1CCC2 XKNJKKXCPOGINE-UHFFFAOYSA-N 0.000 claims description 2
- AZVDCNKFNRCARM-UHFFFAOYSA-N n-cyclohexyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1NC2CCCCC2)=NC2=C1CCC2 AZVDCNKFNRCARM-UHFFFAOYSA-N 0.000 claims description 2
- PPRZHPKKDVNLTJ-UHFFFAOYSA-N n-cyclohexyl-2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C(N=C1NC2CCCCC2)=NC2=C1CCC2 PPRZHPKKDVNLTJ-UHFFFAOYSA-N 0.000 claims description 2
- MQXYGWJHOABDIK-UHFFFAOYSA-N n-cyclopentyl-2-(3,4-dimethoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 MQXYGWJHOABDIK-UHFFFAOYSA-N 0.000 claims description 2
- XOTUXHUSCXTYQE-UHFFFAOYSA-N n-cyclopentyl-2-(3,5-dichlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC(Cl)=CC(C=2N=C(NC3CCCC3)C=3CCCC=3N=2)=C1 XOTUXHUSCXTYQE-UHFFFAOYSA-N 0.000 claims description 2
- HHYMRWQLZNNEGY-UHFFFAOYSA-N n-cyclopentyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 HHYMRWQLZNNEGY-UHFFFAOYSA-N 0.000 claims description 2
- ZGRLBUXNONOKGU-UHFFFAOYSA-N n-cyclopentyl-2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 ZGRLBUXNONOKGU-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P11/06—Antiasthmatics
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- 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
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
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- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853278A DE19853278A1 (de) | 1998-11-19 | 1998-11-19 | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19853278.4 | 1998-11-19 | ||
| PCT/EP1999/008382 WO2000031047A1 (de) | 1998-11-19 | 1999-11-03 | Substituierte 4-amino-2-aryl-cyclopenta[d]pyrimidine, ihre herstellung, ihre verwendung und sie enthaltende pharmazeutische präparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2351488A1 CA2351488A1 (en) | 2000-06-02 |
| CA2351488C true CA2351488C (en) | 2009-12-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351488A Expired - Fee Related CA2351488C (en) | 1998-11-19 | 1999-11-03 | Substituted 4-amino-2-arylcyclopenta[d]pyrimidines, their preparation, their use and pharmaceutical preparations comprising them |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6627628B1 (enExample) |
| EP (1) | EP1131302B1 (enExample) |
| JP (1) | JP4695262B2 (enExample) |
| AT (1) | ATE316964T1 (enExample) |
| AU (1) | AU1159400A (enExample) |
| CA (1) | CA2351488C (enExample) |
| DE (2) | DE19853278A1 (enExample) |
| ES (1) | ES2257103T3 (enExample) |
| PT (1) | PT1131302E (enExample) |
| WO (1) | WO2000031047A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19853278A1 (de) * | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19904710A1 (de) | 1999-02-05 | 2000-08-10 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-tetrahydrochinazoline, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
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| EP2938610A2 (en) | 2012-12-28 | 2015-11-04 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Inhibitors of the usp1/uaf1 deubiquitinase complex and uses thereof |
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|---|---|---|---|---|
| US3346452A (en) | 1963-08-19 | 1967-10-10 | Ciba Geigy Corp | 5, 6-lower alkylene-pyrimidines |
| DE4029654A1 (de) * | 1990-09-19 | 1992-04-02 | Hoechst Ag | 2-phenyl-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
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| JPH07228573A (ja) * | 1994-02-16 | 1995-08-29 | Dainippon Pharmaceut Co Ltd | ２−フェニルシクロアルカノピリミジン誘導体 |
| IL117659A (en) | 1995-04-13 | 2000-12-06 | Dainippon Pharmaceutical Co | Substituted 2-phenyl pyrimidino amino acetamide derivative process for preparing the same and a pharmaceutical composition containing same |
| WO1997047601A1 (en) | 1996-06-11 | 1997-12-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
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| DE19642255A1 (de) | 1996-10-14 | 1998-04-16 | Bayer Ag | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| DE19836697A1 (de) | 1998-08-13 | 2000-02-17 | Hoechst Marion Roussel De Gmbh | Substituierte 4-Amino-2-aryl-pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19853278A1 (de) * | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
-
1998
- 1998-11-19 DE DE19853278A patent/DE19853278A1/de not_active Withdrawn
-
1999
- 1999-11-03 WO PCT/EP1999/008382 patent/WO2000031047A1/de not_active Ceased
- 1999-11-03 ES ES99972626T patent/ES2257103T3/es not_active Expired - Lifetime
- 1999-11-03 AT AT99972626T patent/ATE316964T1/de active
- 1999-11-03 EP EP99972626A patent/EP1131302B1/de not_active Expired - Lifetime
- 1999-11-03 US US09/856,069 patent/US6627628B1/en not_active Expired - Lifetime
- 1999-11-03 JP JP2000583875A patent/JP4695262B2/ja not_active Expired - Fee Related
- 1999-11-03 CA CA002351488A patent/CA2351488C/en not_active Expired - Fee Related
- 1999-11-03 DE DE59913103T patent/DE59913103D1/de not_active Expired - Lifetime
- 1999-11-03 PT PT99972626T patent/PT1131302E/pt unknown
- 1999-11-03 AU AU11594/00A patent/AU1159400A/en not_active Abandoned
-
2003
- 2003-09-12 US US10/660,489 patent/US7138398B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6627628B1 (en) | 2003-09-30 |
| WO2000031047A1 (de) | 2000-06-02 |
| US20040048850A1 (en) | 2004-03-11 |
| AU1159400A (en) | 2000-06-13 |
| ATE316964T1 (de) | 2006-02-15 |
| US7138398B2 (en) | 2006-11-21 |
| PT1131302E (pt) | 2006-05-31 |
| JP2002530385A (ja) | 2002-09-17 |
| DE19853278A1 (de) | 2000-05-25 |
| CA2351488A1 (en) | 2000-06-02 |
| EP1131302A1 (de) | 2001-09-12 |
| ES2257103T3 (es) | 2006-07-16 |
| DE59913103D1 (de) | 2006-04-13 |
| JP4695262B2 (ja) | 2011-06-08 |
| EP1131302B1 (de) | 2006-02-01 |
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| MKLA | Lapsed |
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