CA2757654C - Sulfonic amide and sulfoximine-substituted diaryl-dihydropyrimidinones and usage thereof - Google Patents
Sulfonic amide and sulfoximine-substituted diaryl-dihydropyrimidinones and usage thereof Download PDFInfo
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- CA2757654C CA2757654C CA2757654A CA2757654A CA2757654C CA 2757654 C CA2757654 C CA 2757654C CA 2757654 A CA2757654 A CA 2757654A CA 2757654 A CA2757654 A CA 2757654A CA 2757654 C CA2757654 C CA 2757654C
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- formula
- cyano
- substituted
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- alkyl
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- 150000001408 amides Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 239000003814 drug Substances 0.000 claims abstract description 20
- 230000002265 prevention Effects 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 92
- -1 cyano, methyl Chemical group 0.000 claims description 79
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 239000012453 solvate Substances 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 43
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 42
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 35
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 206010069351 acute lung injury Diseases 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 229940124530 sulfonamide Drugs 0.000 claims description 14
- 150000003456 sulfonamides Chemical class 0.000 claims description 14
- 206010014561 Emphysema Diseases 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000005555 sulfoximide group Chemical group 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 239000000395 magnesium oxide Substances 0.000 claims description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 9
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 claims description 9
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 5
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
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- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- ITDJKCJYYAQMRO-UHFFFAOYSA-L rhodium(2+);diacetate Chemical compound [Rh+2].CC([O-])=O.CC([O-])=O ITDJKCJYYAQMRO-UHFFFAOYSA-L 0.000 claims description 4
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims description 3
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 239000000808 adrenergic beta-agonist Substances 0.000 claims description 2
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003862 glucocorticoid Substances 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 2
- 150000003815 prostacyclins Chemical class 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 229940037128 systemic glucocorticoids Drugs 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- 238000000034 method Methods 0.000 abstract description 120
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 68
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
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- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
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- 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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- 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
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- 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
- A61P9/12—Antihypertensives
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009016553A DE102009016553A1 (de) | 2009-04-06 | 2009-04-06 | Sulfonamid- und Sulfoximin-substituierte Diaryldihydropyrimidinone und ihre Verwendung |
| DE102009016553.3 | 2009-04-06 | ||
| PCT/EP2010/002000 WO2010115548A1 (de) | 2009-04-06 | 2010-03-30 | Sulfonamid- und sulfoximin-substituierte diaryldihydropyrimidinone und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
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| CA2757654A1 CA2757654A1 (en) | 2010-10-14 |
| CA2757654C true CA2757654C (en) | 2017-03-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2757654A Active CA2757654C (en) | 2009-04-06 | 2010-03-30 | Sulfonic amide and sulfoximine-substituted diaryl-dihydropyrimidinones and usage thereof |
Country Status (8)
| Country | Link |
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| US (1) | US8691817B2 (enExample) |
| EP (1) | EP2417112B1 (enExample) |
| JP (1) | JP5608217B2 (enExample) |
| CN (1) | CN102482231B (enExample) |
| CA (1) | CA2757654C (enExample) |
| DE (1) | DE102009016553A1 (enExample) |
| ES (1) | ES2499417T3 (enExample) |
| WO (1) | WO2010115548A1 (enExample) |
Families Citing this family (16)
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| SI2234985T1 (sl) * | 2007-12-20 | 2012-06-29 | Bayer Pharma AG | 4-(4-ciano-2-tioaril)dihidropirimidinoni in njihova uporaba |
| US20140221335A1 (en) | 2013-02-06 | 2014-08-07 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9115093B2 (en) | 2013-03-04 | 2015-08-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| USRE47493E1 (en) | 2014-02-20 | 2019-07-09 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US20170114049A1 (en) | 2014-04-03 | 2017-04-27 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentane carboxylic acids for the treatment of respiratory tract diseases |
| EP3126339A1 (de) | 2014-04-03 | 2017-02-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituierte cyclopentancarbonsäuren und ihre verwendung |
| JP2017511319A (ja) | 2014-04-03 | 2017-04-20 | バイエル ファーマ アクチエンゲゼルシャフト | キラル２，５−ジ置換されたシクロペンタンカルボン酸誘導体およびそれの使用 |
| US9657015B2 (en) | 2014-07-31 | 2017-05-23 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9458113B2 (en) | 2014-07-31 | 2016-10-04 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9475779B2 (en) | 2014-07-31 | 2016-10-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9440930B2 (en) | 2014-07-31 | 2016-09-13 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9290457B2 (en) * | 2014-07-31 | 2016-03-22 | Boehringer Ingelheim International Gmbh | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US10316001B2 (en) | 2015-03-18 | 2019-06-11 | Ph Pharma Co., Ltd. | Method for producing (4S)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrohydro pyrimidine-5-carbonitrile |
| US20190008867A1 (en) | 2015-11-13 | 2019-01-10 | Ph Pharma Co., Ltd. | 4-(4-cyano-2-thioaryl)dihydropyrimidinones for treating chronic wounds |
| WO2024161371A1 (en) * | 2023-02-02 | 2024-08-08 | Gt Gain Therapeutics Sa | Substituted azoles their use in the treatment of diseases associated with alpha-1 -antitrypsin (a1at) deficiency |
| CN118845775B (zh) * | 2024-09-24 | 2024-12-20 | 四川大学华西第二医院 | Iacs-010759在制备预防和/或治疗原发性纤毛不动综合征的药物中的用途 |
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| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| AU2003255492A1 (en) | 2002-09-10 | 2004-04-30 | Bayer Healthcare Ag | Heterocyclic derivatives |
| MXPA05002644A (es) | 2002-09-10 | 2005-09-20 | Bayer Healthcare Ag | Derivados de pirimidinona como agentes terapeuticos contra procesos de remodelacion, isquemicos e inflamatorios agudos y cronicos. |
| GB2392910A (en) * | 2002-09-10 | 2004-03-17 | Bayer Ag | 2-Oxopyrimidine derivatives and their use as human leukocyte elastase inhibitors |
| US7166603B2 (en) | 2003-07-23 | 2007-01-23 | Bristol-Myers Squibb Co. | Dihydropyrimidone inhibitors of calcium channel function |
| EP1730121B1 (en) | 2004-02-26 | 2013-08-07 | Bayer Intellectual Property GmbH | 1,4-diaryl-dihydropyrimidin-2-ones and their use as human neutrophil elastase inhibitors |
| JP4825194B2 (ja) | 2004-02-26 | 2011-11-30 | バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト | １，４−ジアリール−ジヒドロピリミジン−２−オン化合物およびヒト好中球エラスターゼ阻害剤としてのそれらの使用 |
| JP2008508356A (ja) | 2004-08-02 | 2008-03-21 | スミスクライン ビーチャム コーポレーション | Ｈｐｖ感染に有用な化合物 |
| GB0502258D0 (en) | 2005-02-03 | 2005-03-09 | Argenta Discovery Ltd | Compounds and their use |
| GB0512940D0 (en) | 2005-06-24 | 2005-08-03 | Argenta Discovery Ltd | Compounds and their use |
| GB0520743D0 (en) | 2005-10-12 | 2005-11-23 | Argenta Discovery Ltd | Compounds and their use |
| US20100010024A1 (en) | 2006-07-01 | 2010-01-14 | Bayer Healthcare Ag | Use of1,4-diaryl-dihydropyrimidine-2-on derivatives for treating pulmonary arterial hypertension |
| DE102006031314A1 (de) | 2006-07-01 | 2008-01-03 | Bayer Healthcare Aktiengesellschaft | Verwendung von 1,4-Diaryl-dihydropyrimidin-2-on-Derivaten zur Behandlung der pulmonalen arteriellen Hyptertonie |
| US20110003858A1 (en) | 2006-09-04 | 2011-01-06 | Bergstroem Lena | Multimeric heterocyclic compounds useful as neutrophil elastase inhibitors |
| SI2234985T1 (sl) * | 2007-12-20 | 2012-06-29 | Bayer Pharma AG | 4-(4-ciano-2-tioaril)dihidropirimidinoni in njihova uporaba |
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2009
- 2009-04-06 DE DE102009016553A patent/DE102009016553A1/de not_active Withdrawn
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2010
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- 2010-03-30 US US13/262,159 patent/US8691817B2/en active Active
- 2010-03-30 ES ES10713311.8T patent/ES2499417T3/es active Active
- 2010-03-30 JP JP2012503892A patent/JP5608217B2/ja not_active Expired - Fee Related
- 2010-03-30 WO PCT/EP2010/002000 patent/WO2010115548A1/de not_active Ceased
- 2010-03-30 CN CN201080024887.8A patent/CN102482231B/zh not_active Expired - Fee Related
- 2010-03-30 EP EP10713311.8A patent/EP2417112B1/de active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20120094968A1 (en) | 2012-04-19 |
| US8691817B2 (en) | 2014-04-08 |
| ES2499417T3 (es) | 2014-09-29 |
| CN102482231A (zh) | 2012-05-30 |
| DE102009016553A1 (de) | 2010-10-07 |
| WO2010115548A1 (de) | 2010-10-14 |
| JP2012522814A (ja) | 2012-09-27 |
| JP5608217B2 (ja) | 2014-10-15 |
| CN102482231B (zh) | 2014-12-17 |
| HK1171451A1 (en) | 2013-03-28 |
| EP2417112B1 (de) | 2014-07-09 |
| CA2757654A1 (en) | 2010-10-14 |
| EP2417112A1 (de) | 2012-02-15 |
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