CA2837248A1 - Novel phthalazinone -pyrrolopyrimidinecarboxamide derivatives - Google Patents
Novel phthalazinone -pyrrolopyrimidinecarboxamide derivatives Download PDFInfo
- Publication number
- CA2837248A1 CA2837248A1 CA2837248A CA2837248A CA2837248A1 CA 2837248 A1 CA2837248 A1 CA 2837248A1 CA 2837248 A CA2837248 A CA 2837248A CA 2837248 A CA2837248 A CA 2837248A CA 2837248 A1 CA2837248 A1 CA 2837248A1
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- piperidin
- pyrrolo
- pyrimidine
- hexahydrophthalazin
- 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.)
- Abandoned
Links
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 655
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract description 4
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 130
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 126
- 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 122
- -1 2-oxoazetidin-1-yl Chemical group 0.000 claims description 109
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 91
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 81
- 150000003839 salts Chemical class 0.000 claims description 75
- 229940060037 fluorine Drugs 0.000 claims description 72
- 229910052731 fluorine Inorganic materials 0.000 claims description 72
- 239000011737 fluorine Substances 0.000 claims description 72
- 235000019000 fluorine Nutrition 0.000 claims description 72
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 43
- 150000002431 hydrogen Chemical group 0.000 claims description 40
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 31
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [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 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000003003 spiro group Chemical group 0.000 claims description 22
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 16
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 14
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 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
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 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
- 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
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 10
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 10
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound 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 5
- 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 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 4
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 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 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 5
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 230000001154 acute effect Effects 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 230000001684 chronic effect Effects 0.000 claims 4
- 208000023504 respiratory system disease Diseases 0.000 claims 4
- 238000011321 prophylaxis Methods 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 2
- 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 2
- 208000006673 asthma Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003119 guanylate cyclase activator Substances 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
- OKJFSJFCRDLPLF-UUWRZZSWSA-N 4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-n-[(2r)-1-[4-[9-(3,4-dimethoxyphenyl)-6-oxo-7,8-diazaspiro[4.5]dec-8-en-7-yl]piperidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-5h-pyrrolo[3,2-d]pyrimidine-7-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CC1(CCCC1)C1=O)=NN1C1CCN(C(=O)[C@@H](CC=2C=CC=CC=2)NC(=O)C=2C3=NC=NC(=C3NC=2)C=2C(=CC=C3OCOC3=2)OCC2CC2)CC1 OKJFSJFCRDLPLF-UUWRZZSWSA-N 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 102000003834 Histamine H1 Receptors Human genes 0.000 claims 1
- 108090000110 Histamine H1 Receptors Proteins 0.000 claims 1
- 239000000867 Lipoxygenase Inhibitor Substances 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
- 239000000556 agonist Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
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- 239000002876 beta blocker Substances 0.000 claims 1
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- 239000000812 cholinergic antagonist Substances 0.000 claims 1
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- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
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- 239000003580 lung surfactant Substances 0.000 claims 1
- 229940066294 lung surfactant Drugs 0.000 claims 1
- 229960003073 pirfenidone Drugs 0.000 claims 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
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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 106
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- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical class OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- WCCDMVZNXNVVQM-UHFFFAOYSA-N piperidin-4-ylhydrazine Chemical compound NNC1CCNCC1 WCCDMVZNXNVVQM-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 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
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003883 substance clean up Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11170440.9 | 2011-06-17 | ||
| 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 |
|---|---|
| CA2837248A1 true CA2837248A1 (en) | 2012-12-20 |
Family
ID=44764312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2837248A Abandoned CA2837248A1 (en) | 2011-06-17 | 2012-06-12 | Novel phthalazinone -pyrrolopyrimidinecarboxamide derivatives |
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 |
| JP2014517021A (ja) | 2014-07-17 |
| CN103582644B (zh) | 2016-07-20 |
| MX2013014888A (es) | 2014-02-27 |
| 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 |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20190612 |