SK11382003A3 - Piperidino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Piperidino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK11382003A3
Authority: SK; Slovakia
Prior art keywords: phenyl; alkyl; alkoxy; tetrahydro; oxo
Prior art date: 2001-02-15

Application number

SK1138-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Armin Hatzelmann

Daniela Bundschuh

Hans-Peter Kley

Gerhard Grundler

Beate Schmidt

Geert Jan Sterk

Hendrik Timmerman

Johannes A. M. Christiaans

Original Assignee

Altana Pharma Ag

Priority date (The priority date 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 date listed.)

2001-02-15

Filing date

2002-02-14

Publication date

2004-01-08

2002-02-14 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2004-01-08 Publication of SK11382003A3 publication Critical patent/SK11382003A3/sk

Links

229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title abstract description 5
239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 86
-1 5-dimethylaminonaphthalin-1-yl Chemical group 0.000 claims description 223
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 34
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 31
150000003839 salts Chemical class 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
125000004076 pyridyl group Chemical group 0.000 claims description 22
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 18
229910052731 fluorine Inorganic materials 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
125000001153 fluoro group Chemical group F* 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
150000001555 benzenes Chemical class 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000002430 hydrocarbons Chemical group 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
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
NGZFTPGHJJBJHZ-UHFFFAOYSA-N 4a,5,8,8a-tetrahydro-2h-phthalazin-1-one Chemical compound C1C=CCC2C(=O)NN=CC21 NGZFTPGHJJBJHZ-UHFFFAOYSA-N 0.000 claims description 3
VBKPPDYGFUZOAJ-UHFFFAOYSA-N 5-oxopentanoic acid Chemical compound OC(=O)CCCC=O VBKPPDYGFUZOAJ-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
150000003053 piperidines Chemical class 0.000 claims description 3
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
CPXGCFWBODLLFD-UHFFFAOYSA-N 4a,5,8,8a-tetrahydro-2h-naphthalen-1-one Chemical compound C1C=CCC2C(=O)CC=CC21 CPXGCFWBODLLFD-UHFFFAOYSA-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
208000023504 respiratory system disease Diseases 0.000 claims description 2
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 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
QWJOSUUTFBUYBX-DUXSLQFZSA-N (4aS,8aR)-4-(3,4-dimethoxyphenyl)-2-[1-(1-phenylethyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(C)C=2C=CC=CC=2)CC1 QWJOSUUTFBUYBX-DUXSLQFZSA-N 0.000 claims 1
NHVCANZLYPMKSR-LEWJYISDSA-N (4as,8ar)-2-(1-acetylpiperidin-4-yl)-4-(3,4-diethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(C)=O)CC1 NHVCANZLYPMKSR-LEWJYISDSA-N 0.000 claims 1
PMSDQTJDMYHMRP-VQTJNVASSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-(1-methylsulfonylpiperidin-4-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(C)(=O)=O)CC1 PMSDQTJDMYHMRP-VQTJNVASSA-N 0.000 claims 1
AMRVEJYMDSINDP-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(4-nitrophenyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C=2C=CC(=CC=2)[N+]([O-])=O)CC1 AMRVEJYMDSINDP-XZOQPEGZSA-N 0.000 claims 1
IDSNOSDXUZNXFS-RRPNLBNLSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)CC1 IDSNOSDXUZNXFS-RRPNLBNLSA-N 0.000 claims 1
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 1
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 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
239000007858 starting material Substances 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 19
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
238000002425 crystallisation Methods 0.000 description 15
230000008025 crystallization Effects 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 12
238000000034 method Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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239000003112 inhibitor Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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AFLRARNCCZQUGM-UHFFFAOYSA-N piperidin-4-ylhydrazine;dihydrochloride Chemical compound Cl.Cl.NNC1CCNCC1 AFLRARNCCZQUGM-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
XMUKSDXYIZPZAZ-UHFFFAOYSA-N tert-butyl 4-[(2-methylpropan-2-yl)oxycarbonylhydrazinylidene]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)NN=C1CCN(C(=O)OC(C)(C)C)CC1 XMUKSDXYIZPZAZ-UHFFFAOYSA-N 0.000 description 3
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Classifications

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- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- 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
- 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

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SK1138-2003A 2001-02-15 2002-02-14 Piperidino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie SK11382003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01103496		2001-02-15
PCT/EP2002/001547 WO2002064584A1 (en)	2001-02-15	2002-02-14	Phthalayinone-piperidino-derivatives as pde4 inhibitors

Publications (1)

Publication Number	Publication Date
SK11382003A3 true SK11382003A3 (sk)	2004-01-08

Family

ID=8176497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1138-2003A SK11382003A3 (sk)	2001-02-15	2002-02-14	Piperidino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (22)

Country	Link
US (3)	US6953853B2 (et)
EP (1)	EP1362044A1 (et)
JP (1)	JP4301812B2 (et)
KR (1)	KR20030074817A (et)
CN (1)	CN1524080A (et)
AU (1)	AU2002234634B2 (et)
BG (1)	BG108124A (et)
BR (1)	BR0207278A (et)
CA (1)	CA2438520C (et)
CZ (1)	CZ20032491A3 (et)
EA (1)	EA200300836A1 (et)
EE (1)	EE05386B1 (et)
HR (1)	HRP20030636B1 (et)
HU (1)	HUP0303193A3 (et)
IL (1)	IL156812A0 (et)
MX (1)	MXPA03007310A (et)
NO (1)	NO325245B1 (et)
NZ (1)	NZ527424A (et)
PL (1)	PL363391A1 (et)
SK (1)	SK11382003A3 (et)
WO (1)	WO2002064584A1 (et)
ZA (1)	ZA200306815B (et)

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AU2003255376A1 (en) *	2002-08-10	2004-03-11	Altana Pharma Ag	Piperidine-derivatives as pde4 inhibitors
EP1556369A1 (en) *	2002-08-10	2005-07-27	ALTANA Pharma AG	Pyridazinone-derivatives as pde4 inhibitors
ATE360627T1 (de)	2002-08-10	2007-05-15	Altana Pharma Ag	Pyrrolidindion-substituierte piperidin- phthalazone als pde4-inhibitoren
PL373597A1 (en) *	2002-08-10	2005-09-05	Altana Pharma Ag	Piperidine-n-oxide-derivatives
WO2004062671A2 (en) *	2003-01-14	2004-07-29	Altana Pharma Ag	Pde4 inhibitors for the treatment of neoplasms of lymphoid cells
WO2004098578A2 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Composition comprising a pde4 inhibitor and a tnf-alfa antagonist selected from infliximab, adalimumab, cdp870 and cdp517
WO2004098633A1 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Composition comprising a pde-4 inhibitor and a tnf alpha antagonist
WO2004098606A1 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Composition comprising a pde4 inhibitor and shuil-1r ii
WO2004098605A1 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Pharmaceutical composition comprising a pde4 inhibitor and il-1 trap
CA2525946C (en) *	2003-05-22	2013-01-29	Altana Pharma Ag	Composition comprising a pde4 inhibitor and a pde5 inhibitor
MXPA06002521A (es) *	2003-09-05	2006-06-20	Altana Pharma Ag	Uso de inhibidores de pde4 para el tratamiento de diabetes mellitus.
ES2304692T3 (es)	2004-02-04	2008-10-16	Nycomed Gmbh	Derivados de 2-(piperidin-4-il)-4,5-dihidro-2h-piridazin-3-ona como inhibidores de pde4.
EP1720854A1 (en) *	2004-02-04	2006-11-15	Altana Pharma AG	Phthalzinone derivatives as pde4 inhibitors
WO2005075437A1 (en) *	2004-02-04	2005-08-18	Altana Pharma Ag	Pyridazinone derivatives and their use as pde4 inhibitors
EP1874308A1 (en)	2005-03-08	2008-01-09	Nycomed GmbH	Roflumilast for the treatment of diabetes mellitus
EP2218442A1 (en)	2005-11-09	2010-08-18	CombinatoRx, Inc.	Methods, compositions, and kits for the treatment of ophthalmic disorders
JP2009523805A (ja) *	2006-01-17	2009-06-25	シグナルファーマシューティカルズ，エルエルシー	ＴＮＦα、ＰＤＥ４及びＢ−ＲＡＦの阻害剤、それらの組成物及びそれらの使用法
ES2378281T3 (es) *	2006-07-05	2012-04-10	Nycomed Gmbh	Combinación de atorvastatina con un inhibidor de fosfodiesterasa 4 para el tratamiento de neumopatías inflamatorias
JP2010513393A (ja) *	2006-12-20	2010-04-30	グラクソグループリミテッド	Ｈ１受容体アンタゴニストとしての４−ベンジル−ｌ（２ｈ）−フタラジノン
SI2148876T1 (sl)	2007-05-16	2012-01-31	Nycomed Gmbh	Pirazolonski derivati kot PDE4 inhibitorji
AR074318A1 (es)	2008-11-14	2011-01-05	Nycomed Gmbh	Derivados heterociclicos de pirazolona, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades de las vias respiratorias.
AR086915A1 (es) *	2011-06-17	2014-01-29	Nycomed Gmbh	Derivados de ftalazinona-pirrolopirimidinacarboxamida y composiciones farmaceuticas que los contiene
EP2804603A1 (en)	2012-01-10	2014-11-26	President and Fellows of Harvard College	Beta-cell replication promoting compounds and methods of their use
EP3165224A1 (en)	2015-11-09	2017-05-10	Albert-Ludwigs-Universität Freiburg	Use of pde4 inhibitors for the prophylaxis and/or therapy of dyslipoproteinaemia and related disorders
JP6820717B2 (ja)	2016-10-28	2021-01-27	株式会社日立ハイテク	プラズマ処理装置
CN113121417A (zh) *	2019-12-30	2021-07-16	苏州盛迪亚生物医药有限公司	一种新型哌啶衍生物及其药物用途
WO2021192210A1 (ja)	2020-03-27	2021-09-30	株式会社日立ハイテク	半導体製造方法

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AU673569B2 (en)	1992-12-02	1996-11-14	Pfizer Inc.	Catechol diethers as selective PDE-IV inhibitors
DE19533975A1 (de)	1995-09-14	1997-03-20	Merck Patent Gmbh	Arylalkyl-diazinone
HUP0001541A3 (en) *	1997-01-15	2001-11-28	Altana Pharma Ag	Phthalazinone derivatives and pharmaceutical compositions containing them
DE69821530T2 (de) *	1997-12-15	2004-12-23	Altana Pharma Ag	Dihydrobenzifurane
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JP2002506856A (ja) *	1998-03-14	2002-03-05	ビイクグルデンロンベルクヒエーミツシエフアブリークゲゼルシヤフトミツトベシユレンクテルハフツング	フタラジノンｐｄｅｉｉｉ／ｉｖ阻害剤
WO2001019818A1 (en)	1999-09-14	2001-03-22	Byk Gulden Lomberg Chemische Fabrik Gmbh	Phthalazinone derivatives as pd3/4 inhibitors
HK1047276A1 (zh) *	1999-10-25	2003-02-14	Altana Pharma Ag	作为pde4抑制剂的四氢噻喃2，3-二氮杂萘酮类衍生物
DE60036558D1 (de) *	1999-10-25	2007-11-08	Nycomed Gmbh	Phthalazinon-derivate als pde 4 hemmer
KR20030031907A (ko)	2000-06-05	2003-04-23	알타나 파마 아게	β-2-아드레날린 수용체 작동물질로서 뿐만 아니라ＰＤＥ4-억제제로서 효과적인 화합물
US6953853B2 (en) *	2001-02-15	2005-10-11	Altana Pharma Ag	Phthalazinone-piperidino-derivatives as PDE4 inhibitors
US7022696B2 (en)	2001-04-25	2006-04-04	Altana Pharma Ag	Piperazino-derivatives and their use as PDE4 inhibitor
JP2004526789A (ja)	2001-04-25	2004-09-02	アルタナ　ファルマ　アクチエンゲゼルシャフト	新規フタラジノン
ATE360627T1 (de)	2002-08-10	2007-05-15	Altana Pharma Ag	Pyrrolidindion-substituierte piperidin- phthalazone als pde4-inhibitoren
EP1556369A1 (en)	2002-08-10	2005-07-27	ALTANA Pharma AG	Pyridazinone-derivatives as pde4 inhibitors
PL373597A1 (en)	2002-08-10	2005-09-05	Altana Pharma Ag	Piperidine-n-oxide-derivatives

2002
- 2002-02-14 US US10/467,832 patent/US6953853B2/en not_active Expired - Fee Related
- 2002-02-14 EE EEP200300311A patent/EE05386B1/et not_active IP Right Cessation
- 2002-02-14 JP JP2002564515A patent/JP4301812B2/ja not_active Expired - Fee Related
- 2002-02-14 CN CNA02805038XA patent/CN1524080A/zh active Pending
- 2002-02-14 EP EP02701277A patent/EP1362044A1/en not_active Withdrawn
- 2002-02-14 AU AU2002234634A patent/AU2002234634B2/en not_active Ceased
- 2002-02-14 SK SK1138-2003A patent/SK11382003A3/sk unknown
- 2002-02-14 CZ CZ20032491A patent/CZ20032491A3/cs unknown
- 2002-02-14 HR HRP20030636AA patent/HRP20030636B1/xx not_active IP Right Cessation
- 2002-02-14 BR BR0207278-5A patent/BR0207278A/pt not_active IP Right Cessation
- 2002-02-14 HU HU0303193A patent/HUP0303193A3/hu unknown
- 2002-02-14 EA EA200300836A patent/EA200300836A1/ru unknown
- 2002-02-14 CA CA2438520A patent/CA2438520C/en not_active Expired - Fee Related
- 2002-02-14 WO PCT/EP2002/001547 patent/WO2002064584A1/en not_active Ceased
- 2002-02-14 KR KR10-2003-7010552A patent/KR20030074817A/ko not_active Withdrawn
- 2002-02-14 NZ NZ527424A patent/NZ527424A/en not_active IP Right Cessation
- 2002-02-14 IL IL15681202A patent/IL156812A0/xx unknown
- 2002-02-14 MX MXPA03007310A patent/MXPA03007310A/es active IP Right Grant
- 2002-02-14 PL PL02363391A patent/PL363391A1/xx unknown
2003
- 2003-08-14 NO NO20033618A patent/NO325245B1/no not_active IP Right Cessation
- 2003-08-21 BG BG108124A patent/BG108124A/bg unknown
- 2003-09-01 ZA ZA200306815A patent/ZA200306815B/en unknown
2005
- 2005-06-03 US US11/143,721 patent/US7179810B2/en not_active Expired - Fee Related
2006
- 2006-12-29 US US11/647,191 patent/US7531540B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US20040067946A1 (en)	2004-04-08
EP1362044A1 (en)	2003-11-19
US20050234062A1 (en)	2005-10-20
BR0207278A (pt)	2004-02-10
NO20033618L (no)	2003-10-15
HUP0303193A3 (en)	2007-08-28
CZ20032491A3 (cs)	2004-01-14
MXPA03007310A (es)	2003-12-04
NO325245B1 (no)	2008-03-10
JP4301812B2 (ja)	2009-07-22
NZ527424A (en)	2005-02-25
CN1524080A (zh)	2004-08-25
US20070129373A1 (en)	2007-06-07
ZA200306815B (en)	2004-06-17
US7531540B2 (en)	2009-05-12
JP2004518727A (ja)	2004-06-24
PL363391A1 (en)	2004-11-15
KR20030074817A (ko)	2003-09-19
BG108124A (bg)	2004-08-31
CA2438520A1 (en)	2002-08-22
AU2002234634B2 (en)	2007-07-26
EE05386B1 (et)	2011-02-15
WO2002064584A1 (en)	2002-08-22
HRP20030636A2 (en)	2005-06-30
US7179810B2 (en)	2007-02-20
US6953853B2 (en)	2005-10-11
EA200300836A1 (ru)	2004-02-26
IL156812A0 (en)	2004-02-08
EE200300311A (et)	2003-10-15
HUP0303193A2 (hu)	2003-12-29
NO20033618D0 (no)	2003-08-14
HRP20030636B1 (en)	2012-05-31
CA2438520C (en)	2011-10-04

Publication	Publication Date	Title
JP4301812B2 (ja)	2009-07-22	Ｐｄｅ４インヒビターとしてのフタラインオン−ピペリジノ−誘導体
JP4555684B2 (ja)	2010-10-06	Ｐｄｅ４阻害剤としての、ピロリジンジオンにより置換されたピペリジン−フタラゾン
US20060166995A1 (en)	2006-07-27	Piperidine-n-oxide-derivatives
AU2002234634A1 (en)	2003-02-20	Phthalayinone-piperidino-derivatives as PDE4 inhibitors
US20060167001A1 (en)	2006-07-27	Pyridazinone-derivatives as pde4 inhibitors
WO2004018449A1 (en)	2004-03-04	Piperidine-derivatives as pde4 inhibitors
AU2002315311B2 (en)	2007-12-06	Piperazino-derivatives and their use as PDE4 inhibitor

Legal Events

Date	Code	Title	Description
2013-09-03	TC4A	Change of owner's name	Owner name: TAKEDA GMBH, KONSTANZ, DE Effective date: 20130725
2013-12-02	FD9A	Suspended procedure due to non-payment of fee

Date

Code

Title

Description

2013-09-03

TC4A

Change of owner's name

Owner name: TAKEDA GMBH, KONSTANZ, DE

Effective date: 20130725

2013-12-02

FD9A

Suspended procedure due to non-payment of fee