ES2236504T3 - 6-fenilbenzonaftiridinas. - Google Patents
6-fenilbenzonaftiridinas.Info
- Publication number
- ES2236504T3 ES2236504T3 ES02722110T ES02722110T ES2236504T3 ES 2236504 T3 ES2236504 T3 ES 2236504T3 ES 02722110 T ES02722110 T ES 02722110T ES 02722110 T ES02722110 T ES 02722110T ES 2236504 T3 ES2236504 T3 ES 2236504T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- hydrogen
- radical
- methyl
- cycloalkyl
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- -1 1-hexahydroazepinyl Chemical group 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 94
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 38
- 125000004429 atom Chemical group 0.000 claims description 37
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 36
- 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 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 230000003287 optical effect Effects 0.000 claims description 24
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 206010048768 Dermatosis Diseases 0.000 claims description 2
- XHOXTJKCNLNKET-GOTSBHOMSA-N N([C@H]1CCN(C)C[C@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)NC(=N)N1CCCC1 Chemical compound N([C@H]1CCN(C)C[C@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=C1)=CC=C1C(=O)NC(=N)N1CCCC1 XHOXTJKCNLNKET-GOTSBHOMSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 50
- 229960004198 guanidine Drugs 0.000 claims 5
- UFZQSFBZUWNMFG-STQMWFEESA-N (3r,4s)-3-(3-ethoxy-4-methoxyphenyl)-1-methylpiperidin-4-amine Chemical compound C1=C(OC)C(OCC)=CC([C@H]2[C@H](CCN(C)C2)N)=C1 UFZQSFBZUWNMFG-STQMWFEESA-N 0.000 claims 2
- NPLHZKUQZKRZQG-GOTSBHOMSA-N 4-[(4aS,10bR)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1H-benzo[c][1,6]naphthyridin-6-yl]-N-(N'-butylcarbamimidoyl)benzamide Chemical compound C(CCC)NC(=N)NC(=O)C1=CC=C(C=C1)C1=N[C@H]2CCN(C[C@H]2C2=C1C=C(C(=C2)OCC)OC)C NPLHZKUQZKRZQG-GOTSBHOMSA-N 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 101100135868 Dictyostelium discoideum pde3 gene Proteins 0.000 abstract description 9
- 239000003112 inhibitor Substances 0.000 abstract description 7
- 239000002253 acid Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
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- 239000006260 foam Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
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- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 7
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- 239000000725 suspension Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 238000011321 prophylaxis Methods 0.000 description 6
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 108010044467 Isoenzymes Proteins 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000006480 benzoylation reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- QYQKEEKSROGRBQ-UHFFFAOYSA-N 6-phenylbenzo[b][1,8]naphthyridine Chemical class C1=CC=CC=C1C1=CC=CC2=NC3=NC=CC=C3C=C12 QYQKEEKSROGRBQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 3
- 206010040070 Septic Shock Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 3
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- CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 description 1
- UTGGIQHJOAPIPD-UHFFFAOYSA-N methyl 3-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=CC(C(Cl)=O)=C1 UTGGIQHJOAPIPD-UHFFFAOYSA-N 0.000 description 1
- CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000019499 negative regulation of cell activation Effects 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000007112 pro inflammatory response Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 125000003410 quininyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (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)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01104086 | 2001-02-21 | ||
| EP01104086 | 2001-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2236504T3 true ES2236504T3 (es) | 2005-07-16 |
Family
ID=8176545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02722110T Expired - Lifetime ES2236504T3 (es) | 2001-02-21 | 2002-02-21 | 6-fenilbenzonaftiridinas. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6936622B2 (enExample) |
| EP (1) | EP1377574B1 (enExample) |
| JP (1) | JP4248245B2 (enExample) |
| AT (1) | ATE287403T1 (enExample) |
| AU (1) | AU2002253045B2 (enExample) |
| CA (1) | CA2438717C (enExample) |
| DE (1) | DE60202669T2 (enExample) |
| DK (1) | DK1377574T3 (enExample) |
| ES (1) | ES2236504T3 (enExample) |
| PT (1) | PT1377574E (enExample) |
| SI (1) | SI1377574T1 (enExample) |
| WO (1) | WO2002066476A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2495597A1 (en) * | 2002-08-17 | 2004-03-04 | Altana Pharma Ag | Novel phenanthridines |
| AU2003263216A1 (en) * | 2002-08-17 | 2004-03-11 | Nycomed Gmbh | Benzonaphthyridines with PDE 3/4 inhibiting activity |
| CA2496459C (en) | 2002-08-29 | 2013-06-25 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| JP4638736B2 (ja) * | 2002-09-04 | 2011-02-23 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規のベンゾナフチリジン |
| US7470704B2 (en) | 2002-09-04 | 2008-12-30 | Nycomed Gmbh | Benzonaphthyridines |
| EP1720835B1 (en) * | 2004-02-18 | 2012-12-12 | Nycomed GmbH | Novel guanidinyl-substituted hydroxy-6-phenylphenanthridines as effective phosphodiesterase (pde) 4 inhibitors |
| PL2589599T4 (pl) | 2004-03-03 | 2015-06-30 | Takeda Gmbh | Nowe hydroksy-6-heteroarylofenantrydyny i ich zastosowanie jako inhibitorów PDE4 |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| MXPA06009892A (es) * | 2004-03-10 | 2007-03-01 | Altana Pharma Ag | Nuevas hidroxi-6-fenilfenantridinas sustituidas con amido y su uso como inhibidores de la fosfodiesterasa tipo 4 (pde4). |
| EP1732925A1 (en) | 2004-03-17 | 2006-12-20 | Altana Pharma AG | Novel n-(alkoxyalkyl)carbamoyl- substituted 6-phenyl-benzonaphthyridine derivatives and their use as pde3/4 inhibitors |
| ES2337083T3 (es) | 2005-03-02 | 2010-04-20 | Nycomed Gmbh | (2r,4ar,10br)-6-(2,6-dimetoxipiridin-3-il)-9-exoti-8-metoxi-1,2,3,4,4a,10b-hexahidrofenantridin-2-ol, sal de hc1. |
| WO2018069210A1 (en) | 2016-10-10 | 2018-04-19 | Takeda Gmbh | Tetrahydrofuro[3,4-c]isoquinolines as inhibitors of pde4 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0937074T3 (da) * | 1996-11-11 | 2003-06-23 | Altana Pharma Ag | Benzonaphthyridiner som bronkiale terapeutiske midler |
| SI0968211T1 (en) * | 1997-03-07 | 2004-02-29 | Altana Pharma Ag | Tetrazole derivatives |
| AU8106598A (en) | 1997-06-03 | 1998-12-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzonaphthyridine |
| CA2330738A1 (en) * | 1998-05-05 | 1999-11-11 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel n-oxides of benzonaphthyridines |
| SI1109810T1 (en) * | 1998-08-31 | 2004-12-31 | Altana Pharma Ag | Benzonaphthyridine-n-oxides comprising a pde3 and pde4 inhibiting activity |
-
2002
- 2002-02-21 US US10/467,568 patent/US6936622B2/en not_active Expired - Fee Related
- 2002-02-21 DE DE60202669T patent/DE60202669T2/de not_active Expired - Lifetime
- 2002-02-21 WO PCT/EP2002/001819 patent/WO2002066476A1/en not_active Ceased
- 2002-02-21 PT PT02722110T patent/PT1377574E/pt unknown
- 2002-02-21 AU AU2002253045A patent/AU2002253045B2/en not_active Ceased
- 2002-02-21 SI SI200230083T patent/SI1377574T1/xx unknown
- 2002-02-21 ES ES02722110T patent/ES2236504T3/es not_active Expired - Lifetime
- 2002-02-21 DK DK02722110T patent/DK1377574T3/da active
- 2002-02-21 EP EP02722110A patent/EP1377574B1/en not_active Expired - Lifetime
- 2002-02-21 JP JP2002565990A patent/JP4248245B2/ja not_active Expired - Fee Related
- 2002-02-21 CA CA2438717A patent/CA2438717C/en not_active Expired - Fee Related
- 2002-02-21 AT AT02722110T patent/ATE287403T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| US20040097537A1 (en) | 2004-05-20 |
| EP1377574A1 (en) | 2004-01-07 |
| CA2438717A1 (en) | 2002-08-29 |
| PT1377574E (pt) | 2005-05-31 |
| JP2004526712A (ja) | 2004-09-02 |
| SI1377574T1 (enExample) | 2005-08-31 |
| AU2002253045B2 (en) | 2007-07-12 |
| WO2002066476A9 (en) | 2003-10-30 |
| DE60202669D1 (de) | 2005-02-24 |
| ATE287403T1 (de) | 2005-02-15 |
| JP4248245B2 (ja) | 2009-04-02 |
| EP1377574B1 (en) | 2005-01-19 |
| DK1377574T3 (da) | 2005-04-25 |
| US6936622B2 (en) | 2005-08-30 |
| WO2002066476A1 (en) | 2002-08-29 |
| CA2438717C (en) | 2011-08-30 |
| DE60202669T2 (de) | 2005-09-15 |
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