ES2251867B1 - Nuevos derivados de piridazin-3(2h)-ona. - Google Patents
Nuevos derivados de piridazin-3(2h)-ona. Download PDFInfo
- Publication number
- ES2251867B1 ES2251867B1 ES200401512A ES200401512A ES2251867B1 ES 2251867 B1 ES2251867 B1 ES 2251867B1 ES 200401512 A ES200401512 A ES 200401512A ES 200401512 A ES200401512 A ES 200401512A ES 2251867 B1 ES2251867 B1 ES 2251867B1
- Authority
- ES
- Spain
- Prior art keywords
- ethyl
- oxo
- carboxylate
- ylamino
- dihydropyridazin
- 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
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- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- 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 abstract description 32
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims abstract description 32
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 230000001575 pathological effect Effects 0.000 claims abstract description 13
- 230000002265 prevention Effects 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- -1 hydroxy, hydroxycarbonyl Chemical group 0.000 claims description 416
- 125000001424 substituent group Chemical group 0.000 claims description 119
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000004429 atom Chemical group 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 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 description 24
- MBHNPBUZXZJWKI-UHFFFAOYSA-N O=C1N(CC)N=C(C(O)=O)C(C(C)=O)=C1NC1=CN=CC2=CC=CC=C12 Chemical compound O=C1N(CC)N=C(C(O)=O)C(C(C)=O)=C1NC1=CN=CC2=CC=CC=C12 MBHNPBUZXZJWKI-UHFFFAOYSA-N 0.000 claims description 24
- RPINGVXRPYKYIQ-UHFFFAOYSA-N 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylic acid Chemical compound O=C1N(CC)N=C(C(O)=O)C=C1NC1=CN=CC2=CC=CC=C12 RPINGVXRPYKYIQ-UHFFFAOYSA-N 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- FVHJOZXLLCUNPP-UHFFFAOYSA-N O=C1N(CC)N=C(C(O)=O)C(C(C)=O)=C1NC1=CC=CN=C1 Chemical compound O=C1N(CC)N=C(C(O)=O)C(C(C)=O)=C1NC1=CC=CN=C1 FVHJOZXLLCUNPP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000004442 acylamino group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 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 description 13
- 229940079593 drug Drugs 0.000 claims description 13
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000005110 aryl thio group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 8
- 230000006872 improvement Effects 0.000 claims description 8
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003431 steroids Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003018 immunosuppressive agent Substances 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 6
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- CIYUPPPHUTVXKV-UHFFFAOYSA-N O=C1N(CC)N=C(C(O)=O)C(C(C)=O)=C1NC1=CN=CC=C1C Chemical compound O=C1N(CC)N=C(C(O)=O)C(C(C)=O)=C1NC1=CN=CC=C1C CIYUPPPHUTVXKV-UHFFFAOYSA-N 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
- 108091008874 T cell receptors Proteins 0.000 claims description 4
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
- UXBWUANOUDOKAX-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-yl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound C1CC2=CC=CC=C2C1OC(=O)C1=NN(CC)C(=O)C(NC=2C3=CC=CC=C3C=NC=2)=C1 UXBWUANOUDOKAX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000000048 adrenergic agonist Substances 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
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- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims description 2
- 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- BCTIUOAMRBQOSL-UHFFFAOYSA-N butan-2-yl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CCC(C)OC(=O)C1=NN(CC)C(=O)C(NC=2C3=CC=CC=C3C=NC=2)=C1C(C)=O BCTIUOAMRBQOSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000013066 combination product Substances 0.000 claims description 2
- 229940127555 combination product Drugs 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
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- YBAFRKFYYVKMNM-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-yl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC2C3=CC=CC=C3CC2)C=C1NC1=CN=CC=C1C YBAFRKFYYVKMNM-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 134
- 238000000034 method Methods 0.000 abstract description 72
- 230000005764 inhibitory process Effects 0.000 abstract description 13
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 abstract description 11
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 18
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
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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
- C07D405/14—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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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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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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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200401512A ES2251867B1 (es) | 2004-06-21 | 2004-06-21 | Nuevos derivados de piridazin-3(2h)-ona. |
| PE2005000702A PE20060531A1 (es) | 2004-06-21 | 2005-06-20 | Derivados de piridazin-3-(2h)-ona como inhibidores de la fosfodiesterasa 4 |
| MXPA06014562A MXPA06014562A (es) | 2004-06-21 | 2005-06-21 | Derivados de piridazin-3(2h)-ona y su uso como inhibidores de pde4. |
| UAA200700276A UA87691C2 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
| CA002570196A CA2570196A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
| EP05752744A EP1781621A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
| PCT/EP2005/006712 WO2005123693A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
| AU2005254704A AU2005254704A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2H)-one derivatives and their use as PDE4 inhibitors |
| NZ551284A NZ551284A (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2H)-one derivatives and their use as PDE4 inhibitors |
| US11/629,527 US20090029996A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2H)-One Derivatives And Their Use As Pde4 Inhibitors |
| TW094120704A TW200610757A (en) | 2004-06-21 | 2005-06-21 | New pyridazin-3(2H)-one derivatives |
| SG200906269-6A SG155943A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
| BRPI0511344-0A BRPI0511344A (pt) | 2004-06-21 | 2005-06-21 | composto, composição farmacêutica, uso de um composto, método para o tratamento de um sujeito que sofre de uma condição patológica ou doença susceptìvel de melhora pela inibição de fosfodiesterase 4 e produto combinado |
| RU2007102223/04A RU2386620C2 (ru) | 2004-06-21 | 2005-06-21 | Производные пиридазин-3(2н)-она и их применение в качестве ингибиторов фдэ4 |
| CNA2005800193338A CN1976904A (zh) | 2004-06-21 | 2005-06-21 | 哒嗪－3(2h)－酮衍生物及其作为pde4抑止剂的应用 |
| JP2007517186A JP2008503531A (ja) | 2004-06-21 | 2005-06-21 | 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 |
| KR1020077001315A KR20070036137A (ko) | 2004-06-21 | 2005-06-21 | 피리다진-３（２ｈ）-온 유도체 및 이의 ｐｄｅ４저해제로서의 용도 |
| ARP050102533A AR051738A1 (es) | 2004-06-21 | 2005-06-21 | Derivados de piridazin-3(2h)-ona, composicin farmaceutica, y uso del compuesto para fabricar medicamentos |
| ZA200609399A ZA200609399B (en) | 2004-06-21 | 2006-11-13 | Pyridazin-3(2H)-one derivatives and their use as PDE4 inhibitors |
| IL179741A IL179741A0 (en) | 2004-06-21 | 2006-11-30 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
| EC2006007057A ECSP067057A (es) | 2004-06-21 | 2006-12-08 | Nuevos derivados de piridazin-3(2h)-ona |
| NO20070319A NO20070319L (no) | 2004-06-21 | 2007-01-17 | Nye pyridazin-3(2H)-on-derivater og deres anvendelse som PDE4-inhibitorer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200401512A ES2251867B1 (es) | 2004-06-21 | 2004-06-21 | Nuevos derivados de piridazin-3(2h)-ona. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2251867A1 ES2251867A1 (es) | 2006-05-01 |
| ES2251867B1 true ES2251867B1 (es) | 2007-06-16 |
Family
ID=34956037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200401512A Expired - Fee Related ES2251867B1 (es) | 2004-06-21 | 2004-06-21 | Nuevos derivados de piridazin-3(2h)-ona. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20090029996A1 (https=) |
| EP (1) | EP1781621A1 (https=) |
| JP (1) | JP2008503531A (https=) |
| KR (1) | KR20070036137A (https=) |
| CN (1) | CN1976904A (https=) |
| AR (1) | AR051738A1 (https=) |
| AU (1) | AU2005254704A1 (https=) |
| BR (1) | BRPI0511344A (https=) |
| CA (1) | CA2570196A1 (https=) |
| EC (1) | ECSP067057A (https=) |
| ES (1) | ES2251867B1 (https=) |
| IL (1) | IL179741A0 (https=) |
| MX (1) | MXPA06014562A (https=) |
| NO (1) | NO20070319L (https=) |
| NZ (1) | NZ551284A (https=) |
| PE (1) | PE20060531A1 (https=) |
| RU (1) | RU2386620C2 (https=) |
| SG (1) | SG155943A1 (https=) |
| TW (1) | TW200610757A (https=) |
| UA (1) | UA87691C2 (https=) |
| WO (1) | WO2005123693A1 (https=) |
| ZA (1) | ZA200609399B (https=) |
Families Citing this family (56)
| 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. |
| ES2251866B1 (es) | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| 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. |
| US9086277B2 (en) * | 2007-03-13 | 2015-07-21 | Certusview Technologies, Llc | Electronically controlled marking apparatus and methods |
| KR20100016620A (ko) | 2007-04-23 | 2010-02-12 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 4-알콕시피리다진 유도체 |
| AU2008240729B2 (en) | 2007-04-23 | 2012-08-23 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| 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 |
| 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 |
| 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 |
| 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 |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| EP2338888A1 (en) | 2009-12-24 | 2011-06-29 | Almirall, S.A. | Imidazopyridine derivatives as JAK inhibitors |
| EP2360158A1 (en) | 2010-02-18 | 2011-08-24 | Almirall, S.A. | Pyrazole derivatives as jak inhibitors |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| EP2394998A1 (en) * | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
| EP2397482A1 (en) | 2010-06-15 | 2011-12-21 | Almirall, S.A. | Heteroaryl imidazolone derivatives as jak inhibitors |
| EP2441755A1 (en) | 2010-09-30 | 2012-04-18 | Almirall, S.A. | Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
| EP2489663A1 (en) | 2011-02-16 | 2012-08-22 | Almirall, S.A. | Compounds as syk kinase inhibitors |
| EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine derivatives as PI3K inhibitors |
| EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone 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 |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
| US20140278981A1 (en) * | 2011-10-06 | 2014-09-18 | Gueorgui Mersov | Automated allocation of media via network |
| 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. |
| EP2592077A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| 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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| WO2014060431A1 (en) | 2012-10-16 | 2014-04-24 | Almirall, S.A. | Pyrrolotriazinone derivatives as pi3k inhibitors |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| 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 |
| ES2750523T3 (es) | 2012-12-18 | 2020-03-26 | Almirall Sa | Derivados de ciclohexil y quinuclidinil carbamato que tienen actividades de agonista beta2 adrenérgicos y antagonistas muscarínicos M3 |
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| TWI641373B (zh) | 2013-07-25 | 2018-11-21 | 阿爾米雷爾有限公司 | 具有蕈毒鹼受體拮抗劑和β２腎上腺素受體促效劑二者之活性的２－胺基－１－羥乙基－８－羥基喹啉－２（１Ｈ）－酮衍生物之鹽 |
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| TW201617343A (zh) | 2014-09-26 | 2016-05-16 | 阿爾米雷爾有限公司 | 具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物 |
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Also Published As
| Publication number | Publication date |
|---|---|
| UA87691C2 (en) | 2009-08-10 |
| ES2251867A1 (es) | 2006-05-01 |
| KR20070036137A (ko) | 2007-04-02 |
| CN1976904A (zh) | 2007-06-06 |
| US20090029996A1 (en) | 2009-01-29 |
| PE20060531A1 (es) | 2006-06-28 |
| WO2005123693A1 (en) | 2005-12-29 |
| MXPA06014562A (es) | 2007-07-24 |
| ECSP067057A (es) | 2007-03-29 |
| ZA200609399B (en) | 2008-09-25 |
| NO20070319L (no) | 2007-03-06 |
| RU2386620C2 (ru) | 2010-04-20 |
| CA2570196A1 (en) | 2005-12-29 |
| BRPI0511344A (pt) | 2007-12-04 |
| AR051738A1 (es) | 2007-02-07 |
| JP2008503531A (ja) | 2008-02-07 |
| SG155943A1 (en) | 2009-10-29 |
| NZ551284A (en) | 2010-07-30 |
| IL179741A0 (en) | 2007-05-15 |
| EP1781621A1 (en) | 2007-05-09 |
| RU2007102223A (ru) | 2008-07-27 |
| AU2005254704A1 (en) | 2005-12-29 |
| TW200610757A (en) | 2006-04-01 |
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