JP2008502628A5 - - Google Patents
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- Publication number
- JP2008502628A5 JP2008502628A5 JP2007515846A JP2007515846A JP2008502628A5 JP 2008502628 A5 JP2008502628 A5 JP 2008502628A5 JP 2007515846 A JP2007515846 A JP 2007515846A JP 2007515846 A JP2007515846 A JP 2007515846A JP 2008502628 A5 JP2008502628 A5 JP 2008502628A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- ethyl
- dihydropyridazine
- ylamino
- carboxylic acid
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 hydroxy, hydroxycarbonyl Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims description 10
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 10
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 230000001575 pathological effect Effects 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000005110 aryl thio group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- GWOHVTRAFCMHDO-UHFFFAOYSA-N 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylic acid Chemical compound O=C1N(CC)N=C(C(O)=O)C=C1NC1=CN=CC=C1C GWOHVTRAFCMHDO-UHFFFAOYSA-N 0.000 claims 2
- 241001024304 Mino Species 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- SBUHYGKZZCXCQS-UHFFFAOYSA-N 1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylic acid Chemical compound O=C1N(CC)N=C(C(O)=O)C=C1NC1=CC=CN=C1 SBUHYGKZZCXCQS-UHFFFAOYSA-N 0.000 claims 1
- UUQIWPAFMMRAIA-UHFFFAOYSA-N 1-phenylpropan-2-yl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC(C)CC1=CC=CC=C1 UUQIWPAFMMRAIA-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JYABTTWTIDRDDX-UHFFFAOYSA-N CCN1C(=O)C(=C(C(=N1)C(=O)O)C(=O)C)NC2=CC=CC3=C2C=CC=N3 Chemical compound CCN1C(=O)C(=C(C(=N1)C(=O)O)C(=O)C)NC2=CC=CC3=C2C=CC=N3 JYABTTWTIDRDDX-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 108091008874 T cell receptors Proteins 0.000 claims 1
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 229940124589 immunosuppressive drug Drugs 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 28
- 239000007787 solid Substances 0.000 description 26
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VROMXVIODDASTK-UHFFFAOYSA-N 5-amino-1h-pyridazin-6-one Chemical class NC1=CC=NNC1=O VROMXVIODDASTK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940076286 cupric acetate Drugs 0.000 description 2
- 208000037765 diseases and disorders Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HCITYDRGAUSHMA-UHFFFAOYSA-N 1-phenylethyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC(C)C1=CC=CC=C1 HCITYDRGAUSHMA-UHFFFAOYSA-N 0.000 description 1
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- BYMCZTUYKOHNQB-UHFFFAOYSA-N CCN1C(=O)C(C(C=N1)(C(=O)C)C(=O)OCC)NC2=CC=CC3=C2C=CC=N3 Chemical compound CCN1C(=O)C(C(C=N1)(C(=O)C)C(=O)OCC)NC2=CC=CC3=C2C=CC=N3 BYMCZTUYKOHNQB-UHFFFAOYSA-N 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 206010060742 Endocrine ophthalmopathy Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008455 cerebrovascular function Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- JXKWUDNZEPRUSE-UHFFFAOYSA-N cyclobutyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC1CCC1 JXKWUDNZEPRUSE-UHFFFAOYSA-N 0.000 description 1
- JSASAAWXXZOLNE-UHFFFAOYSA-N cyclopropylmethyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C(=O)OCC1CC1 JSASAAWXXZOLNE-UHFFFAOYSA-N 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 201000010064 diabetes insipidus Diseases 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000036473 myasthenia Effects 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- NWIJBOCPTGHGIK-UHFFFAOYSA-N quinolin-5-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=N1 NWIJBOCPTGHGIK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200401500A ES2251866B1 (es) | 2004-06-18 | 2004-06-18 | Nuevos derivados de piridazin-3(2h)-ona. |
| PCT/EP2005/006304 WO2005123692A1 (en) | 2004-06-18 | 2005-06-13 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008502628A JP2008502628A (ja) | 2008-01-31 |
| JP2008502628A5 true JP2008502628A5 (https=) | 2008-07-17 |
Family
ID=34956035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007515846A Pending JP2008502628A (ja) | 2004-06-18 | 2005-06-13 | ピリダジン−３（２ｈ）−オン誘導体およびｐｄｅ４の阻害剤としてのそれらの使用 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7960383B2 (https=) |
| EP (1) | EP1758869B1 (https=) |
| JP (1) | JP2008502628A (https=) |
| KR (1) | KR20070029808A (https=) |
| CN (1) | CN1964952A (https=) |
| AR (1) | AR049402A1 (https=) |
| AT (1) | ATE492538T1 (https=) |
| AU (1) | AU2005254659A1 (https=) |
| BR (1) | BRPI0511383A (https=) |
| CA (1) | CA2570170A1 (https=) |
| DE (1) | DE602005025478D1 (https=) |
| EC (1) | ECSP067058A (https=) |
| ES (2) | ES2251866B1 (https=) |
| IL (1) | IL179734A0 (https=) |
| MX (1) | MXPA06013593A (https=) |
| NO (1) | NO20070321L (https=) |
| PE (1) | PE20060436A1 (https=) |
| RU (1) | RU2376293C2 (https=) |
| SG (1) | SG155909A1 (https=) |
| TW (1) | TW200612951A (https=) |
| UA (1) | UA88472C2 (https=) |
| UY (1) | UY28958A1 (https=) |
| WO (1) | WO2005123692A1 (https=) |
| ZA (1) | ZA200609403B (https=) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2211344B1 (es) | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| CA2546353A1 (en) * | 2003-11-19 | 2005-06-09 | Array Biopharma Inc. | Bicyclic inhibitors of mek and methods of use thereof |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| ES2251866B1 (es) | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| SG177981A1 (en) * | 2005-05-18 | 2012-02-28 | Array Biopharma Inc | 4-(phenylamino)-6-oxo-1, 6-dihydropyridazine-3-carboxamide derivatives as mek inhibitors for the treatment of hyperproliferative diseases |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| JO2849B1 (en) | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| AU2008240729B2 (en) | 2007-04-23 | 2012-08-23 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| KR20100016620A (ko) | 2007-04-23 | 2010-02-12 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 4-알콕시피리다진 유도체 |
| EP2096105A1 (en) | 2008-02-28 | 2009-09-02 | Laboratorios Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| CA2730774C (en) | 2008-07-31 | 2016-09-13 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| EP2221055A1 (en) | 2009-02-18 | 2010-08-25 | Almirall, S.A. | 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one for the treatment of lung function |
| EP2221297A1 (en) | 2009-02-18 | 2010-08-25 | Almirall, S.A. | 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one and its use in the treatment of pulmonary diseases |
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| EP2489663A1 (en) | 2011-02-16 | 2012-08-22 | Almirall, S.A. | Compounds as syk kinase inhibitors |
| EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
| EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine derivatives as PI3K inhibitors |
| EP2527344A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Pyridin-2(1H)-one derivatives useful as medicaments for the treatment of myeloproliferative disorders, transplant rejection, immune-mediated and inflammatory diseases |
| EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
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| EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
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| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| EP2647627A1 (en) | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Salts of 5-[(1r)-2-({2-[4-(2,2-difluoro-2-phenylethoxy)phenyl] ethyl}amino)-1-hydroxyethyl]-8-hydroxyquinolin-2(1h)-one. |
| EP2666465A1 (en) | 2012-05-25 | 2013-11-27 | Almirall, S.A. | Novel dosage and formulation |
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| LT2931275T (lt) | 2012-12-17 | 2022-06-27 | Almirall S.A. | Aklidiniumas, skirtas naudoti fizinio aktyvumo kasdieniniame gyvenime padidinimui pacientui, sergančiam lėtine obstrukcine plaučių liga |
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-
2004
- 2004-06-18 ES ES200401500A patent/ES2251866B1/es not_active Expired - Fee Related
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2005
- 2005-06-13 US US11/629,522 patent/US7960383B2/en not_active Expired - Fee Related
- 2005-06-13 WO PCT/EP2005/006304 patent/WO2005123692A1/en not_active Ceased
- 2005-06-13 KR KR1020077001216A patent/KR20070029808A/ko not_active Ceased
- 2005-06-13 JP JP2007515846A patent/JP2008502628A/ja active Pending
- 2005-06-13 SG SG200906039-3A patent/SG155909A1/en unknown
- 2005-06-13 RU RU2007101654/04A patent/RU2376293C2/ru not_active IP Right Cessation
- 2005-06-13 CN CNA2005800187731A patent/CN1964952A/zh active Pending
- 2005-06-13 CA CA002570170A patent/CA2570170A1/en not_active Abandoned
- 2005-06-13 EP EP05751683A patent/EP1758869B1/en not_active Expired - Lifetime
- 2005-06-13 AU AU2005254659A patent/AU2005254659A1/en not_active Abandoned
- 2005-06-13 BR BRPI0511383-0A patent/BRPI0511383A/pt not_active IP Right Cessation
- 2005-06-13 UA UAA200700279A patent/UA88472C2/ru unknown
- 2005-06-13 ES ES05751683T patent/ES2358335T3/es not_active Expired - Lifetime
- 2005-06-13 DE DE602005025478T patent/DE602005025478D1/de not_active Expired - Lifetime
- 2005-06-13 AT AT05751683T patent/ATE492538T1/de not_active IP Right Cessation
- 2005-06-13 UY UY28958A patent/UY28958A1/es unknown
- 2005-06-13 MX MXPA06013593A patent/MXPA06013593A/es active IP Right Grant
- 2005-06-15 PE PE2005000683A patent/PE20060436A1/es not_active Application Discontinuation
- 2005-06-17 TW TW094120336A patent/TW200612951A/zh unknown
- 2005-06-17 AR ARP050102489A patent/AR049402A1/es not_active Application Discontinuation
-
2006
- 2006-11-13 ZA ZA200609403A patent/ZA200609403B/xx unknown
- 2006-11-30 IL IL179734A patent/IL179734A0/en unknown
- 2006-12-08 EC EC2006007058A patent/ECSP067058A/es unknown
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2007
- 2007-01-17 NO NO20070321A patent/NO20070321L/no not_active Application Discontinuation
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