HRP20110940T1 - Derivati pirazolona kao inhibitori pde4 - Google Patents
Derivati pirazolona kao inhibitori pde4 Download PDFInfo
- Publication number
- HRP20110940T1 HRP20110940T1 HR20110940T HRP20110940T HRP20110940T1 HR P20110940 T1 HRP20110940 T1 HR P20110940T1 HR 20110940 T HR20110940 T HR 20110940T HR P20110940 T HRP20110940 T HR P20110940T HR P20110940 T1 HRP20110940 T1 HR P20110940T1
- Authority
- HR
- Croatia
- Prior art keywords
- piperidin
- dihydro
- oxo
- alkoxy
- dione
- Prior art date
Links
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 title 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 55
- -1 pyrrolidine-2,5-dion-1-yl- Chemical group 0.000 claims abstract 38
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 21
- 239000011737 fluorine Substances 0.000 claims abstract 21
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 14
- 125000003003 spiro group Chemical group 0.000 claims abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 8
- 239000001257 hydrogen Substances 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000011321 prophylaxis Methods 0.000 claims 15
- 238000011282 treatment Methods 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 230000001154 acute effect Effects 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 4
- 102000003834 Histamine H1 Receptors Human genes 0.000 claims 4
- 108090000110 Histamine H1 Receptors Proteins 0.000 claims 4
- 239000000556 agonist Substances 0.000 claims 4
- 239000003242 anti bacterial agent Substances 0.000 claims 4
- 229940088710 antibiotic agent Drugs 0.000 claims 4
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 4
- 239000003472 antidiabetic agent Substances 0.000 claims 4
- 229940125708 antidiabetic agent Drugs 0.000 claims 4
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 claims 4
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 claims 4
- 239000000812 cholinergic antagonist Substances 0.000 claims 4
- 239000003246 corticosteroid Substances 0.000 claims 4
- 229960001334 corticosteroids Drugs 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 4
- 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 claims 4
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 4
- 239000003580 lung surfactant Substances 0.000 claims 4
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 4
- 229940044551 receptor antagonist Drugs 0.000 claims 4
- 239000002464 receptor antagonist Substances 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- NVOCTEMAFLHIJD-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(CCC2=O)=O)CC1 NVOCTEMAFLHIJD-UHFFFAOYSA-N 0.000 claims 3
- 208000018569 Respiratory Tract disease Diseases 0.000 claims 3
- 239000012752 auxiliary agent Substances 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- YMWIFJZZVYOEDH-UHFFFAOYSA-N 1-[2-[4-[1-(3,4-dimethoxyphenyl)-4-oxo-2,3-diazaspiro[4.4]non-1-en-3-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C1(CCCC1)C1=O)=NN1C1CCN(C(=O)CN2C(CCC2=O)=O)CC1 YMWIFJZZVYOEDH-UHFFFAOYSA-N 0.000 claims 2
- PIDDEXINYDGDOP-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-diethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=C(OCC)C(OCC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(CCC2=O)=O)CC1 PIDDEXINYDGDOP-UHFFFAOYSA-N 0.000 claims 2
- IDKFKENERKGLRX-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-diethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound CCC1(CC)C(=O)N(C2CCN(CC2)C(=O)CN2C(CCC2=O)=O)N=C1C1=CC=C(OC)C(OC)=C1 IDKFKENERKGLRX-UHFFFAOYSA-N 0.000 claims 2
- ZZNGKVBVYAZELT-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]piperidine-2,6-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(CCCC2=O)=O)CC1 ZZNGKVBVYAZELT-UHFFFAOYSA-N 0.000 claims 2
- JZLBJLUCFAJSOB-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-dimethoxyphenyl)-4-ethyl-4-methyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound CCC1(C)C(=O)N(C2CCN(CC2)C(=O)CN2C(CCC2=O)=O)N=C1C1=CC=C(OC)C(OC)=C1 JZLBJLUCFAJSOB-UHFFFAOYSA-N 0.000 claims 2
- AKJOYNASSKRIMN-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-dimethoxyphenyl)-4-methyl-5-oxo-4-propylpyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound CCCC1(C)C(=O)N(C2CCN(CC2)C(=O)CN2C(CCC2=O)=O)N=C1C1=CC=C(OC)C(OC)=C1 AKJOYNASSKRIMN-UHFFFAOYSA-N 0.000 claims 2
- PDYAPLCZXYJGQA-UHFFFAOYSA-N 1-[2-[4-[3-(3-ethoxy-4-methoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=C(OC)C(OCC)=CC(C=2C(C(=O)N(C3CCN(CC3)C(=O)CN3C(CCC3=O)=O)N=2)(C)C)=C1 PDYAPLCZXYJGQA-UHFFFAOYSA-N 0.000 claims 2
- BQJQLWBPGONFND-UHFFFAOYSA-N 1-[2-[4-[3-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C(CC1)CCN1C(=O)CN1C(=O)CCC1=O BQJQLWBPGONFND-UHFFFAOYSA-N 0.000 claims 2
- PJWRCMMWYNTTIO-UHFFFAOYSA-N 1-[2-[4-[3-(7-methoxyspiro[3h-1-benzofuran-2,1'-cyclopentane]-4-yl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=2CC3(CCCC3)OC=2C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C(CC1)CCN1C(=O)CN1C(=O)CCC1=O PJWRCMMWYNTTIO-UHFFFAOYSA-N 0.000 claims 2
- MVWQCEQFEZYOOY-UHFFFAOYSA-N 1-[2-[4-[3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound CC1(C)C(=O)N(C2CCN(CC2)C(=O)CN2C(CCC2=O)=O)N=C1C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 MVWQCEQFEZYOOY-UHFFFAOYSA-N 0.000 claims 2
- WSNNMTCJCWWBKA-UHFFFAOYSA-N 1-[2-[4-[3-[3-(cyclopropylmethoxy)-4-methoxyphenyl]-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound COC1=CC=C(C=2C(C(=O)N(C3CCN(CC3)C(=O)CN3C(CCC3=O)=O)N=2)(C)C)C=C1OCC1CC1 WSNNMTCJCWWBKA-UHFFFAOYSA-N 0.000 claims 2
- JAAFNIDHDGPHDM-UHFFFAOYSA-N 1-[2-[4-[3-[4-methoxy-3-(2,2,2-trifluoroethoxy)phenyl]-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]pyrrolidine-2,5-dione Chemical compound C1=C(OCC(F)(F)F)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(CCC2=O)=O)CC1 JAAFNIDHDGPHDM-UHFFFAOYSA-N 0.000 claims 2
- VCUUDJPOUGIMBT-UHFFFAOYSA-N 1-[3-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-3-oxopropyl]pyrrolidine-2,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CCN2C(CCC2=O)=O)CC1 VCUUDJPOUGIMBT-UHFFFAOYSA-N 0.000 claims 2
- QDSKEXDKVYNYNZ-UHFFFAOYSA-N 2-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(C3=CC=CC=C3C2=O)=O)CC1 QDSKEXDKVYNYNZ-UHFFFAOYSA-N 0.000 claims 2
- SKFKGWAJTSRCRJ-UHFFFAOYSA-N 4-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]-1,1-dioxo-1,4-thiazinane-3,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(CS(=O)(=O)CC2=O)=O)CC1 SKFKGWAJTSRCRJ-UHFFFAOYSA-N 0.000 claims 2
- ZRGCMKWVMKYWCW-UHFFFAOYSA-N 4-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]morpholine-3,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(COCC2=O)=O)CC1 ZRGCMKWVMKYWCW-UHFFFAOYSA-N 0.000 claims 2
- CHVXUAAOAMBOSV-UHFFFAOYSA-N 4-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]thiomorpholine-3,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C(CSCC2=O)=O)CC1 CHVXUAAOAMBOSV-UHFFFAOYSA-N 0.000 claims 2
- 208000030090 Acute Disease Diseases 0.000 claims 2
- 206010052613 Allergic bronchitis Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- QWZKXTPLDIDPQM-UHFFFAOYSA-N 1-[2-[4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxopyrazol-1-yl]piperidin-1-yl]-2-oxoethyl]-3h-indol-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C(C1=O)(C)C)=NN1C1CCN(C(=O)CN2C3=CC=CC=C3CC2=O)CC1 QWZKXTPLDIDPQM-UHFFFAOYSA-N 0.000 claims 1
- 208000017667 Chronic Disease Diseases 0.000 claims 1
- 208000014085 Chronic respiratory disease Diseases 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
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
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
-
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D405/14—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 three or more hetero rings
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- Health & Medical Sciences (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07108314 | 2007-05-16 | ||
PCT/EP2008/055867 WO2008138939A1 (en) | 2007-05-16 | 2008-05-14 | Pyrazolone derivatives as pde4 inhibitors |
Publications (1)
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HRP20110940T1 true HRP20110940T1 (hr) | 2012-01-31 |
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Application Number | Title | Priority Date | Filing Date |
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HR20110940T HRP20110940T1 (hr) | 2007-05-16 | 2011-12-15 | Derivati pirazolona kao inhibitori pde4 |
Country Status (31)
Country | Link |
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US (3) | US8304436B2 (zh) |
EP (3) | EP2508520A1 (zh) |
JP (2) | JP5529010B2 (zh) |
KR (1) | KR101601284B1 (zh) |
CN (2) | CN103463086B (zh) |
AR (1) | AR066576A1 (zh) |
AT (1) | ATE526326T1 (zh) |
AU (1) | AU2008250069B2 (zh) |
BR (1) | BRPI0811214A2 (zh) |
CA (1) | CA2686909C (zh) |
CO (1) | CO6220956A2 (zh) |
CY (1) | CY1112152T1 (zh) |
DK (1) | DK2148876T3 (zh) |
EA (1) | EA018984B1 (zh) |
EC (1) | ECSP099738A (zh) |
ES (2) | ES2427442T3 (zh) |
HK (2) | HK1141017A1 (zh) |
HR (1) | HRP20110940T1 (zh) |
IL (1) | IL201959A (zh) |
ME (1) | ME00952B (zh) |
MX (1) | MX2009012062A (zh) |
MY (1) | MY154498A (zh) |
NZ (1) | NZ581547A (zh) |
PL (1) | PL2148876T3 (zh) |
PT (1) | PT2148876E (zh) |
RS (1) | RS52074B (zh) |
SI (1) | SI2148876T1 (zh) |
TW (2) | TWI460174B (zh) |
UA (1) | UA100019C2 (zh) |
WO (1) | WO2008138939A1 (zh) |
ZA (1) | ZA200906423B (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008138939A1 (en) * | 2007-05-16 | 2008-11-20 | Nycomed Gmbh | Pyrazolone derivatives as pde4 inhibitors |
AR074318A1 (es) | 2008-11-14 | 2011-01-05 | Nycomed Gmbh | Derivados heterociclicos de pirazolona, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades de las vias respiratorias. |
WO2010101246A1 (ja) * | 2009-03-05 | 2010-09-10 | 塩野義製薬株式会社 | Npy y5受容体拮抗作用を有するピペリジンおよびピロリジン誘導体 |
WO2011136752A1 (en) * | 2010-04-26 | 2011-11-03 | Mahmut Bilgic | Combined pharmaceutical composition comprising carmoterol and ciclesonide for the treatment of respiratory diseases |
JP5609614B2 (ja) * | 2010-12-15 | 2014-10-22 | 東ソー株式会社 | 新規アリールアミンデンドリマー状化合物、その製造方法およびその用途 |
EP2968278B8 (en) | 2013-03-15 | 2019-05-22 | Karyopharm Therapeutics Inc. | Methods of promoting wound healing using crm1 inhibitors |
WO2021245192A1 (en) | 2020-06-04 | 2021-12-09 | Topadur Pharma Ag | Novel dual mode of action soluble guanylate cyclase activators and phosphodiesterase inhibitors and uses thereof |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
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US2903460A (en) | 1956-04-07 | 1959-09-08 | Sandoz Ag | Pyrazolone derivatives |
US4550119A (en) | 1983-05-23 | 1985-10-29 | Warner-Lambert Company | 2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones |
IE71647B1 (en) | 1991-01-28 | 1997-02-26 | Rhone Poulenc Rorer Ltd | Benzamide derivatives |
WO1994002465A1 (en) | 1992-07-28 | 1994-02-03 | Rhone-Poulenc Rorer Limited | INHIBITORS OF c-AMP PHOSPHODIESTERASE AND TNF |
PT706513E (pt) | 1993-07-02 | 2002-10-31 | Byk Gulden Lomberg Chem Fab | Benzimidazois substituidos por fluoralcoxi e sua utilizacao como inibidores de fosfodiesterase nucleotidica ciclica |
CZ291758B6 (cs) | 1994-07-22 | 2003-05-14 | Altana Pharma Ag | Dihydrobenzofurany, způsob jejich výroby, jejich použití a farmaceutický prostředek |
PT971901E (pt) | 1997-01-15 | 2003-07-31 | Altana Pharma Ag | Ftalazinonas |
US6418201B1 (en) | 2000-02-22 | 2002-07-09 | Intel Corporation | Multiple platform voice processing system with optimized resource allocation |
PL363391A1 (en) | 2001-02-15 | 2004-11-15 | Altana Pharma Ag | Phthalayinone-piperidino-derivatives as pde4 inhibitors |
AU2002234836B2 (en) | 2001-04-20 | 2007-08-23 | Pfizer Products Inc. | Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds |
BR0209149A (pt) | 2001-04-25 | 2004-07-13 | Altana Pharma Ag | Ftalazinonas |
AU2003258576B2 (en) | 2002-08-10 | 2009-07-30 | Takeda Gmbh | Pyrrolidinedione substituted piperidine-phthalazones as PDE4 inhibitors |
US20060167001A1 (en) | 2002-08-10 | 2006-07-27 | Sterk Jan G | Pyridazinone-derivatives as pde4 inhibitors |
WO2004018449A1 (en) | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
EP1539801B1 (en) | 2002-08-20 | 2015-03-25 | Biosurface Engineering Technologies, Inc. | Synthetic heparin-binding growth factor analogs |
AU2004268847A1 (en) * | 2003-08-29 | 2005-03-10 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-IV |
WO2005075457A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Phthalazinone-derivatives as pde4 inhibitors |
US7494990B2 (en) | 2004-02-04 | 2009-02-24 | Nycomed Gmbh | 2-(piperidin-4-yl)-4,5-dihydro-2H-pyridazin-3-one derivatives as PDE4 inhibitors |
JP2006169138A (ja) * | 2004-12-14 | 2006-06-29 | Kyorin Pharmaceut Co Ltd | ピラゾロピリジンピラゾロン誘導体とその付加塩及びpde阻害剤 |
WO2008138939A1 (en) * | 2007-05-16 | 2008-11-20 | Nycomed Gmbh | Pyrazolone derivatives as pde4 inhibitors |
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2008
- 2008-05-14 WO PCT/EP2008/055867 patent/WO2008138939A1/en active Application Filing
- 2008-05-14 EP EP12174018A patent/EP2508520A1/en not_active Withdrawn
- 2008-05-14 CN CN201310349480.8A patent/CN103463086B/zh not_active Expired - Fee Related
- 2008-05-14 PT PT08759563T patent/PT2148876E/pt unknown
- 2008-05-14 CN CN2008800119475A patent/CN101657441B/zh not_active Expired - Fee Related
- 2008-05-14 MX MX2009012062A patent/MX2009012062A/es active IP Right Grant
- 2008-05-14 BR BRPI0811214-2A2A patent/BRPI0811214A2/pt active Search and Examination
- 2008-05-14 EA EA200901504A patent/EA018984B1/ru not_active IP Right Cessation
- 2008-05-14 ES ES11182678T patent/ES2427442T3/es active Active
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- 2008-05-14 KR KR1020097025745A patent/KR101601284B1/ko not_active IP Right Cessation
- 2008-05-14 ES ES08759563T patent/ES2374337T3/es active Active
- 2008-05-14 EP EP08759563A patent/EP2148876B1/en active Active
- 2008-05-14 UA UAA200912770A patent/UA100019C2/uk unknown
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- 2008-05-14 US US12/451,348 patent/US8304436B2/en not_active Expired - Fee Related
- 2008-05-14 CA CA2686909A patent/CA2686909C/en not_active Expired - Fee Related
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- 2008-05-14 DK DK08759563.3T patent/DK2148876T3/da active
- 2008-05-14 PL PL08759563T patent/PL2148876T3/pl unknown
- 2008-05-14 EP EP11182678.0A patent/EP2402330B1/en active Active
- 2008-05-14 AT AT08759563T patent/ATE526326T1/de active
- 2008-05-14 JP JP2010507909A patent/JP5529010B2/ja not_active Expired - Fee Related
- 2008-05-14 ME MEP-2009-327A patent/ME00952B/me unknown
- 2008-05-14 AU AU2008250069A patent/AU2008250069B2/en not_active Ceased
- 2008-05-15 AR ARP080102055A patent/AR066576A1/es not_active Application Discontinuation
- 2008-05-16 TW TW102129216A patent/TWI460174B/zh not_active IP Right Cessation
- 2008-05-16 TW TW097118165A patent/TWI414521B/zh not_active IP Right Cessation
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2009
- 2009-09-15 ZA ZA200906423A patent/ZA200906423B/xx unknown
- 2009-10-16 CO CO09115665A patent/CO6220956A2/es active IP Right Grant
- 2009-11-05 IL IL201959A patent/IL201959A/en not_active IP Right Cessation
- 2009-11-13 EC EC2009009738A patent/ECSP099738A/es unknown
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2010
- 2010-08-03 HK HK10107416.9A patent/HK1141017A1/xx not_active IP Right Cessation
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2011
- 2011-12-15 HR HR20110940T patent/HRP20110940T1/hr unknown
- 2011-12-20 CY CY20111101261T patent/CY1112152T1/el unknown
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2012
- 2012-09-14 US US13/618,026 patent/US8865745B2/en not_active Expired - Fee Related
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2014
- 2014-04-16 JP JP2014084704A patent/JP5850972B2/ja not_active Expired - Fee Related
- 2014-05-28 HK HK14105008.3A patent/HK1191574A1/zh not_active IP Right Cessation
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