MX2013014888A - Novedosos derivados de ftalazinona-pirrolopirimidinacarboxamida. - Google Patents
Novedosos derivados de ftalazinona-pirrolopirimidinacarboxamida.Info
- Publication number
- MX2013014888A MX2013014888A MX2013014888A MX2013014888A MX2013014888A MX 2013014888 A MX2013014888 A MX 2013014888A MX 2013014888 A MX2013014888 A MX 2013014888A MX 2013014888 A MX2013014888 A MX 2013014888A MX 2013014888 A MX2013014888 A MX 2013014888A
- Authority
- MX
- Mexico
- Prior art keywords
- oxo
- piperidin
- pyrrolo
- pyrimidine
- dimethoxyphenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 568
- 239000003112 inhibitor Substances 0.000 claims abstract description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract 3
- -1 2-oxoazetidin-1-yl Chemical group 0.000 claims description 487
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 312
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 152
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 116
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 109
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 93
- 150000003839 salts Chemical class 0.000 claims description 76
- 239000011737 fluorine Substances 0.000 claims description 71
- 229910052731 fluorine Inorganic materials 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 65
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 52
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 44
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 43
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 23
- 125000003003 spiro group Chemical group 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 20
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 18
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
- SMFFZOQLHYIRDA-UHFFFAOYSA-N 3,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C=C1OC SMFFZOQLHYIRDA-UHFFFAOYSA-N 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 14
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 11
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 11
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 11
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 241000009298 Trigla lyra Species 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 2
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 230000001154 acute effect Effects 0.000 claims 4
- 230000001684 chronic effect Effects 0.000 claims 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- SIXISCAJFLMLLM-UHFFFAOYSA-N 5-(cyclopropylmethoxy)-1,3-benzodioxole Chemical compound C=1C=C2OCOC2=CC=1OCC1CC1 SIXISCAJFLMLLM-UHFFFAOYSA-N 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- FNKQXYHWGSIFBK-RPDRRWSUSA-N sapropterin Chemical compound N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-RPDRRWSUSA-N 0.000 claims 2
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 241000208011 Digitalis Species 0.000 claims 1
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 108010078321 Guanylate Cyclase Proteins 0.000 claims 1
- 102000014469 Guanylate cyclase Human genes 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 1
- GRILGPUHRHEJEX-UHFFFAOYSA-N NC(=O)c1cnc2cnc[nH]c12 Chemical compound NC(=O)c1cnc2cnc[nH]c12 GRILGPUHRHEJEX-UHFFFAOYSA-N 0.000 claims 1
- 102000004316 Oxidoreductases Human genes 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 claims 1
- 229930003316 Vitamin D Natural products 0.000 claims 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
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- 239000003242 anti bacterial agent Substances 0.000 claims 1
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- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 claims 1
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- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
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- 150000002338 glycosides Chemical class 0.000 claims 1
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- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 257
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 242
- 239000012074 organic phase Substances 0.000 description 181
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 180
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- 239000012047 saturated solution Substances 0.000 description 114
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- 238000003818 flash chromatography Methods 0.000 description 103
- 238000010828 elution Methods 0.000 description 89
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- GPDHNZNLPKYHCN-DZOOLQPHSA-N [[(z)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-morpholin-4-ylmethylidene]-dimethylazanium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCOC(=O)C(\C#N)=N/OC(=[N+](C)C)N1CCOCC1 GPDHNZNLPKYHCN-DZOOLQPHSA-N 0.000 description 81
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- GHJORKVUGKXEEY-UHFFFAOYSA-N 4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-5h-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CNC2=C1C1=C2OCOC2=CC=C1OCC1CC1 GHJORKVUGKXEEY-UHFFFAOYSA-N 0.000 description 50
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- 238000002953 preparative HPLC Methods 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 38
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 38
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- 239000003960 organic solvent Substances 0.000 description 18
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
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- 238000010168 coupling process Methods 0.000 description 10
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- 239000002243 precursor Substances 0.000 description 1
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11170440 | 2011-06-17 | ||
| PCT/EP2012/061084 WO2012171900A1 (en) | 2011-06-17 | 2012-06-12 | Novel phthalazinone-pyrrolopyrimidinecarboxamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2013014888A true MX2013014888A (es) | 2014-02-27 |
Family
ID=44764312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2013014888A MX2013014888A (es) | 2011-06-17 | 2012-06-12 | Novedosos derivados de ftalazinona-pirrolopirimidinacarboxamida. |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US20140112945A1 (https=) |
| EP (1) | EP2721030B1 (https=) |
| JP (1) | JP5980318B2 (https=) |
| KR (1) | KR20140037195A (https=) |
| CN (1) | CN103582644B (https=) |
| AR (1) | AR086915A1 (https=) |
| AU (1) | AU2012269133A1 (https=) |
| BR (1) | BR112013031791A2 (https=) |
| CA (1) | CA2837248A1 (https=) |
| CL (1) | CL2013003556A1 (https=) |
| CO (1) | CO6852074A2 (https=) |
| CR (1) | CR20130656A (https=) |
| DO (1) | DOP2013000298A (https=) |
| EA (1) | EA023713B1 (https=) |
| EC (1) | ECSP13013076A (https=) |
| ES (1) | ES2564882T3 (https=) |
| MA (1) | MA35269B1 (https=) |
| MX (1) | MX2013014888A (https=) |
| PE (1) | PE20140648A1 (https=) |
| PH (1) | PH12013502546A1 (https=) |
| TN (1) | TN2013000439A1 (https=) |
| WO (1) | WO2012171900A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170133497A (ko) | 2015-04-09 | 2017-12-05 | 갈데르마 소시에떼아노님 | 인디고 내추럴리스로부터의 추출물 및 그의 제조 방법 |
| JP6803849B2 (ja) * | 2015-04-09 | 2020-12-23 | ガルデルマ・ソシエテ・アノニム | インジゴナチュラリス又はインジゴ産生植物の抽出物を用いたアトピー性皮膚炎の処置 |
| BR112017021190B1 (pt) | 2015-04-09 | 2021-12-21 | Galderma Sa. | Uso de uma composição farmacêutica que compreende um extrato de indigo naturalis |
| EP3280428A1 (en) | 2015-04-09 | 2018-02-14 | Galderma S.A. | Antibacterial indigo naturalis or indigo-producing plant extract and use thereof |
| WO2022006470A1 (en) | 2020-07-01 | 2022-01-06 | Vanderbilt University | Methods of treatment for a kidney disease |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8828477D0 (en) | 1988-12-06 | 1989-01-05 | Riker Laboratories Inc | Medical aerosol formulations |
| ATE111364T1 (de) | 1989-05-31 | 1994-09-15 | Fisons Plc | Medikament und inhalationsvorrichtung dafür. |
| GB8921222D0 (en) | 1989-09-20 | 1989-11-08 | Riker Laboratories Inc | Medicinal aerosol formulations |
| IL97065A (en) | 1990-02-02 | 1994-01-25 | Fisons Plc | Repellent preparations for aerosol |
| DE4003272A1 (de) | 1990-02-03 | 1991-08-08 | Boehringer Ingelheim Kg | Neue treibgasmischungen und ihre verwendung in arzneimittelzubereitungen |
| DE69131867T2 (de) | 1990-03-23 | 2000-05-18 | Minnesota Mining And Mfg. Co., Saint Paul | Anwendung von löslichen fluorhaltigen Tensiden zur Herstellung von Aerosol-Präparaten mit dosierter Abgabe |
| ATE114112T1 (de) | 1990-10-18 | 1994-12-15 | Minnesota Mining & Mfg | Aerosolzubereitung, die beclometason 17,21- dipropionat enthält. |
| AU650953B2 (en) | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| IL104068A (en) | 1991-12-12 | 1998-10-30 | Glaxo Group Ltd | Surfactant-free pharmaceutical aerosol formulation comprising 1,1,1,2-tetrafluoroethane or 1,1,1,2,3,3,3-heptafluoro-n- propane as propellant |
| GB9213874D0 (en) | 1992-06-30 | 1992-08-12 | Fisons Plc | Process to novel medicament form |
| GB9306703D0 (en) | 1993-03-31 | 1993-05-26 | Fisons Plc | Inhalation device |
| IL111194A (en) | 1993-10-08 | 1998-02-08 | Fisons Plc | Process for the production of medicament formulations |
| BR9806752A (pt) * | 1997-01-15 | 2000-03-14 | Byk Gulden Lomberg Chem Fab | Ftalazinonas. |
| SI1070056T1 (en) * | 1998-03-14 | 2004-12-31 | Altana Pharma Ag | Phthalazinone pde iii/iv inhibitors |
| JP4672143B2 (ja) | 1998-08-04 | 2011-04-20 | ヤゴテック アーゲー | 医薬用エーロゾル製剤 |
| US6397838B1 (en) | 1998-12-23 | 2002-06-04 | Battelle Pulmonary Therapeutics, Inc. | Pulmonary aerosol delivery device and method |
| AU777167B2 (en) | 1999-04-23 | 2004-10-07 | Battelle Memorial Institute | Directionally controlled EHD aerosol sprayer |
| IL146034A0 (en) | 1999-04-23 | 2002-07-25 | Battelle Memorial Institute | High mass transfer electrosprayer |
| NZ522882A (en) * | 2000-06-05 | 2004-07-30 | Altana Pharma Bv | Pyridazinone compounds effective as beta-2-adrenoreceptor agonists as well as PDE4-inhibitors |
| ES2260299T3 (es) | 2000-10-09 | 2006-11-01 | 3M Innovative Properties Company | Formulaciones medicinales en aerosol. |
| CZ20032491A3 (cs) | 2001-02-15 | 2004-01-14 | Altana Pharma Ag | Ftalazinonpiperidinové deriváty |
| EP1385848A2 (en) | 2001-04-25 | 2004-02-04 | ALTANA Pharma AG | Phtalazinones derivatives useful as pde4/7 inhibitors |
| BR0313330A (pt) | 2002-08-10 | 2005-06-14 | Altana Pharma Ag | Piperidina-ftalazonas substituìdas com pirrolidinadiona como inibidores de pde4 |
| EP1556369A1 (en) * | 2002-08-10 | 2005-07-27 | ALTANA Pharma AG | Pyridazinone-derivatives as pde4 inhibitors |
| WO2004018449A1 (en) | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
| EP1587512A2 (en) * | 2003-01-14 | 2005-10-26 | ALTANA Pharma AG | Pde4 inhibitors for the treatment of neoplasms of lymphoid cells |
| WO2005075457A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Phthalazinone-derivatives as pde4 inhibitors |
| DE602005005638T2 (de) | 2004-02-04 | 2009-05-14 | Nycomed Gmbh | 2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-on-derivate als pde4-inhibitoren |
| AR070454A1 (es) * | 2008-02-27 | 2010-04-07 | Nycomed Gmbh | Pirrolopirimidincarboxamidas y composiciones farmaceuticas que las comprenden |
| AR077898A1 (es) * | 2009-08-26 | 2011-09-28 | Nycomed Gmbh | Metilpirrolopirimidincarboxamidas |
-
2012
- 2012-06-12 US US14/125,187 patent/US20140112945A1/en not_active Abandoned
- 2012-06-12 PE PE2013002801A patent/PE20140648A1/es not_active Application Discontinuation
- 2012-06-12 MX MX2013014888A patent/MX2013014888A/es not_active Application Discontinuation
- 2012-06-12 KR KR1020147000392A patent/KR20140037195A/ko not_active Withdrawn
- 2012-06-12 AR ARP120102088A patent/AR086915A1/es unknown
- 2012-06-12 WO PCT/EP2012/061084 patent/WO2012171900A1/en not_active Ceased
- 2012-06-12 CN CN201280028413.XA patent/CN103582644B/zh not_active Expired - Fee Related
- 2012-06-12 EP EP12728453.7A patent/EP2721030B1/en active Active
- 2012-06-12 BR BR112013031791A patent/BR112013031791A2/pt not_active IP Right Cessation
- 2012-06-12 ES ES12728453.7T patent/ES2564882T3/es active Active
- 2012-06-12 CA CA2837248A patent/CA2837248A1/en not_active Abandoned
- 2012-06-12 JP JP2014515155A patent/JP5980318B2/ja not_active Expired - Fee Related
- 2012-06-12 AU AU2012269133A patent/AU2012269133A1/en not_active Abandoned
- 2012-06-12 PH PH1/2013/502546A patent/PH12013502546A1/en unknown
- 2012-06-12 EA EA201400001A patent/EA023713B1/ru not_active IP Right Cessation
-
2013
- 2013-10-29 TN TNP2013000439A patent/TN2013000439A1/fr unknown
- 2013-12-11 EC ECSP13013076 patent/ECSP13013076A/es unknown
- 2013-12-11 DO DO2013000298A patent/DOP2013000298A/es unknown
- 2013-12-11 CL CL2013003556A patent/CL2013003556A1/es unknown
- 2013-12-13 CR CR20130656A patent/CR20130656A/es unknown
-
2014
- 2014-01-10 CO CO14004200A patent/CO6852074A2/es not_active Application Discontinuation
- 2014-01-16 MA MA36689A patent/MA35269B1/fr unknown
-
2015
- 2015-12-03 US US14/958,141 patent/US20160108049A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AR086915A1 (es) | 2014-01-29 |
| CR20130656A (es) | 2014-02-18 |
| EP2721030B1 (en) | 2015-12-16 |
| TN2013000439A1 (en) | 2015-03-30 |
| CO6852074A2 (es) | 2014-01-30 |
| JP5980318B2 (ja) | 2016-08-31 |
| CA2837248A1 (en) | 2012-12-20 |
| JP2014517021A (ja) | 2014-07-17 |
| CN103582644B (zh) | 2016-07-20 |
| CN103582644A (zh) | 2014-02-12 |
| KR20140037195A (ko) | 2014-03-26 |
| WO2012171900A1 (en) | 2012-12-20 |
| US20140112945A1 (en) | 2014-04-24 |
| EA201400001A1 (ru) | 2014-05-30 |
| ECSP13013076A (es) | 2014-01-31 |
| US20160108049A1 (en) | 2016-04-21 |
| MA35269B1 (fr) | 2014-07-03 |
| CL2013003556A1 (es) | 2014-06-13 |
| ES2564882T3 (es) | 2016-03-29 |
| PH12013502546A1 (en) | 2014-01-27 |
| AU2012269133A1 (en) | 2014-01-30 |
| BR112013031791A2 (pt) | 2017-01-31 |
| EA023713B1 (ru) | 2016-07-29 |
| EP2721030A1 (en) | 2014-04-23 |
| PE20140648A1 (es) | 2014-05-30 |
| DOP2013000298A (es) | 2014-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |