JP2012519160A5 - - Google Patents
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- JP2012519160A5 JP2012519160A5 JP2011551465A JP2011551465A JP2012519160A5 JP 2012519160 A5 JP2012519160 A5 JP 2012519160A5 JP 2011551465 A JP2011551465 A JP 2011551465A JP 2011551465 A JP2011551465 A JP 2011551465A JP 2012519160 A5 JP2012519160 A5 JP 2012519160A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- hetaryl
- oxo
- methylene
- 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.)
- Pending
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 99
- 125000001072 heteroaryl group Chemical group 0.000 claims 88
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 86
- 229910052731 fluorine Inorganic materials 0.000 claims 68
- 239000005977 Ethylene Substances 0.000 claims 66
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 60
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 49
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 43
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 43
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 41
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 41
- 229910052801 chlorine Inorganic materials 0.000 claims 40
- 239000000460 chlorine Substances 0.000 claims 40
- -1 O-methyl Chemical group 0.000 claims 38
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 37
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 37
- 229910052794 bromium Inorganic materials 0.000 claims 31
- 125000004043 oxo group Chemical group O=* 0.000 claims 30
- 125000002950 monocyclic group Chemical group 0.000 claims 23
- 229940000425 combination drug Drugs 0.000 claims 22
- 229920006395 saturated elastomer Polymers 0.000 claims 21
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims 19
- 241001164374 Calyx Species 0.000 claims 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 14
- 125000002619 bicyclic group Chemical group 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 10
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 9
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 9
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 9
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 9
- 229960001259 diclofenac Drugs 0.000 claims 9
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 229960001680 ibuprofen Drugs 0.000 claims 9
- 229960001929 meloxicam Drugs 0.000 claims 9
- 229960002009 naproxen Drugs 0.000 claims 9
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 238000009472 formulation Methods 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 229960000905 indomethacin Drugs 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 229960000590 celecoxib Drugs 0.000 claims 5
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 4
- 229920001577 copolymer Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229960003464 mefenamic acid Drugs 0.000 claims 4
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims 4
- 229960002702 piroxicam Drugs 0.000 claims 4
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 4
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- OPKQXJQFEPNJTP-UHFFFAOYSA-N 1-phenylpropa-1,2-dienylbenzene Chemical group C=1C=CC=CC=1C(=C=C)C1=CC=CC=C1 OPKQXJQFEPNJTP-UHFFFAOYSA-N 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 229960004662 parecoxib Drugs 0.000 claims 3
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 claims 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 3
- 229960000371 rofecoxib Drugs 0.000 claims 3
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims 3
- 229960002004 valdecoxib Drugs 0.000 claims 3
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims 3
- IKMNMQWRLOIFQG-LHTANEHXSA-N (1r)-1-[[2-[4-(4-chlorophenyl)piperidin-1-yl]-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amino]-1-(4-fluorophenyl)-2-methylpropan-2-ol Chemical compound N([C@@H](C(C)(O)C)C=1C=CC(F)=CC=1)C(C=1S(=O)CCC=1N=1)=NC=1N(CC1)CCC1C1=CC=C(Cl)C=C1 IKMNMQWRLOIFQG-LHTANEHXSA-N 0.000 claims 2
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims 2
- MCBZSSHPXCOHLX-QUZMYUOTSA-N (2r)-2-[[2-[4-(4-chlorophenyl)piperidin-1-yl]-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amino]-3-methylbutan-1-ol Chemical compound N=1C=2CCS(=O)C=2C(N[C@@H](CO)C(C)C)=NC=1N(CC1)CCC1C1=CC=C(Cl)C=C1 MCBZSSHPXCOHLX-QUZMYUOTSA-N 0.000 claims 2
- QQTRYTIGBOQJEO-VITKDRCNSA-N (2r)-2-[[2-[4-(4-chlorophenyl)piperidin-1-yl]-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amino]pentan-1-ol Chemical compound N=1C=2CCS(=O)C=2C(N[C@@H](CO)CCC)=NC=1N(CC1)CCC1C1=CC=C(Cl)C=C1 QQTRYTIGBOQJEO-VITKDRCNSA-N 0.000 claims 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims 2
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims 2
- HNDKZDBOVQZESS-PTJRXNEBSA-N (5s)-1-methyl-5-[[2-[4-(5-methyl-4-phenyl-1,3-oxazol-2-yl)piperidin-1-yl]-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amino]piperidin-2-one Chemical compound C1CC(=O)N(C)C[C@H]1NC1=NC(N2CCC(CC2)C=2OC(C)=C(N=2)C=2C=CC=CC=2)=NC2=C1S(=O)CC2 HNDKZDBOVQZESS-PTJRXNEBSA-N 0.000 claims 2
- FKDVSMMLLJMFDE-VSCLHSHSSA-N (5s)-5-[[2-[4-(4,5-diphenyl-1,3-oxazol-2-yl)piperidin-1-yl]-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amino]-1-methylpiperidin-2-one Chemical compound C1CC(=O)N(C)C[C@H]1NC1=NC(N2CCC(CC2)C=2OC(=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=NC2=C1S(=O)CC2 FKDVSMMLLJMFDE-VSCLHSHSSA-N 0.000 claims 2
- OCPLJLQANLCXBX-DVYMHAMMSA-N (5s)-5-[[2-[4-(4-chlorophenyl)piperidin-1-yl]-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]amino]-1-methylpiperidin-2-one Chemical compound C1CC(=O)N(C)C[C@H]1NC1=NC(N2CCC(CC2)C=2C=CC(Cl)=CC=2)=NC2=C1S(=O)CC2 OCPLJLQANLCXBX-DVYMHAMMSA-N 0.000 claims 2
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 claims 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 2
- JCUTZUSPPNNLDC-UHFFFAOYSA-N 2-(thiophene-2-carbonyloxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CS1 JCUTZUSPPNNLDC-UHFFFAOYSA-N 0.000 claims 2
- XLVXAUNDHWERBM-IVGWJTKZSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide Chemical compound CC1=C(CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 XLVXAUNDHWERBM-IVGWJTKZSA-N 0.000 claims 2
- XILVEPYQJIOVNB-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester Chemical compound OCCOCCOC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 XILVEPYQJIOVNB-UHFFFAOYSA-N 0.000 claims 2
- RXZTWBVFHQLTBU-UHFFFAOYSA-N 2-[4-(1,3-thiazol-2-yloxy)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC1=NC=CS1 RXZTWBVFHQLTBU-UHFFFAOYSA-N 0.000 claims 2
- YKSNJDFLGOKZKC-UHFFFAOYSA-N 2-[4-(1-methylimidazo[4,5-c]pyridin-2-yl)piperidin-1-yl]-n-(oxan-4-yl)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C2=CN=CC=C2N(C)C=1C(CC1)CCN1C(N=1)=NC=2CCS(=O)C=2C=1NC1CCOCC1 YKSNJDFLGOKZKC-UHFFFAOYSA-N 0.000 claims 2
- OZZNEWKXTONIMY-UHFFFAOYSA-N 2-[4-(2,4-difluorophenyl)piperidin-1-yl]-n-(oxan-4-yl)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-amine Chemical compound FC1=CC(F)=CC=C1C1CCN(C=2N=C(NC3CCOCC3)C=3S(=O)CCC=3N=2)CC1 OZZNEWKXTONIMY-UHFFFAOYSA-N 0.000 claims 2
- AELILMBZWCGOSB-UHFFFAOYSA-N 2-[4-(2,6-dichloroanilino)thiophen-3-yl]acetic acid Chemical compound OC(=O)CC1=CSC=C1NC1=C(Cl)C=CC=C1Cl AELILMBZWCGOSB-UHFFFAOYSA-N 0.000 claims 2
- TYCOFFBAZNSQOJ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC(F)=C1 TYCOFFBAZNSQOJ-UHFFFAOYSA-N 0.000 claims 2
- QWIBUEKESZDCQQ-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)piperidin-1-yl]-n-(oxan-4-yl)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1OC1CCN(C=2N=C(NC3CCOCC3)C=3S(=O)CCC=3N=2)CC1 QWIBUEKESZDCQQ-UHFFFAOYSA-N 0.000 claims 2
- RADUOKRXMKUTGT-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)piperidin-1-yl]-n-(oxan-4-yl)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C1CCN(C=2N=C(NC3CCOCC3)C=3S(=O)CCC=3N=2)CC1 RADUOKRXMKUTGT-UHFFFAOYSA-N 0.000 claims 2
- IQPPOXSMSDPZKU-JQIJEIRASA-N 2-[4-[(3e)-3-hydroxyiminocyclohexyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1CC(=N/O)/CCC1 IQPPOXSMSDPZKU-JQIJEIRASA-N 0.000 claims 2
- FHCZYTNSDHGQAP-UHFFFAOYSA-N 2-[4-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]piperidin-1-yl]-n-(oxan-4-yl)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-amine Chemical compound C=12S(=O)CCC2=NC(N2CCC(CC2)OC=2C=CC(=CC=2)C=2OCCN=2)=NC=1NC1CCOCC1 FHCZYTNSDHGQAP-UHFFFAOYSA-N 0.000 claims 2
- HLEMCKWMUBEVIZ-UHFFFAOYSA-N 2-[4-[5-(furan-2-yl)-2-methylpyrazol-3-yl]piperidin-1-yl]-n-(oxan-4-yl)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-4-amine Chemical compound CN1N=C(C=2OC=CC=2)C=C1C(CC1)CCN1C(N=1)=NC=2CCS(=O)C=2C=1NC1CCOCC1 HLEMCKWMUBEVIZ-UHFFFAOYSA-N 0.000 claims 2
- GTKGEGSAUFYKNW-UHFFFAOYSA-N 3-methyl-1'-[4-(oxan-4-ylamino)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl]spiro[1h-quinazoline-4,4'-piperidine]-2-one Chemical compound CN1C(=O)NC2=CC=CC=C2C1(CC1)CCN1C(N=1)=NC=2CCS(=O)C=2C=1NC1CCOCC1 GTKGEGSAUFYKNW-UHFFFAOYSA-N 0.000 claims 2
- ORZZNUXNGOAYHT-UHFFFAOYSA-N 4-[1-[4-(oxan-4-ylamino)-5-oxo-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl]piperidin-4-yl]oxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1CCN(C=2N=C(NC3CCOCC3)C=3S(=O)CCC=3N=2)CC1 ORZZNUXNGOAYHT-UHFFFAOYSA-N 0.000 claims 2
- SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 claims 2
- DVEQCIBLXRSYPH-UHFFFAOYSA-N 5-butyl-1-cyclohexylbarbituric acid Chemical compound O=C1C(CCCC)C(=O)NC(=O)N1C1CCCCC1 DVEQCIBLXRSYPH-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- MNIPYSSQXLZQLJ-UHFFFAOYSA-N Biofenac Chemical compound OC(=O)COC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl MNIPYSSQXLZQLJ-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 claims 2
- RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 claims 2
- ALIVXCSEERJYHU-UHFFFAOYSA-N Flurbiprofen axetil Chemical compound FC1=CC(C(C)C(=O)OC(OC(C)=O)C)=CC=C1C1=CC=CC=C1 ALIVXCSEERJYHU-UHFFFAOYSA-N 0.000 claims 2
- ACEWLPOYLGNNHV-UHFFFAOYSA-N Ibuprofen piconol Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=O)OCC1=CC=CC=N1 ACEWLPOYLGNNHV-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
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- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims 1
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- KDYWHKGSKGUIQO-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2h-1,2-benzoxazine Chemical compound C1C=CC=C2ONCCC21 KDYWHKGSKGUIQO-UHFFFAOYSA-N 0.000 claims 1
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229960004945 etoricoxib Drugs 0.000 claims 1
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
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- DTHHUAXKOMWYBI-UHFFFAOYSA-N oxadiazolidine Chemical compound C1CONN1 DTHHUAXKOMWYBI-UHFFFAOYSA-N 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
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- 125000003003 spiro group Chemical group 0.000 claims 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims 1
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| PCT/EP2010/052079 WO2010097334A1 (de) | 2009-02-27 | 2010-02-18 | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1847543A1 (de) | 2006-04-19 | 2007-10-24 | Boehringer Ingelheim Pharma GmbH & Co. KG | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
| RU2500681C2 (ru) | 2007-10-19 | 2013-12-10 | Берингер Ингельхайм Интернациональ Гмбх | Замещенные гетероциклом пиперазинодигидротиенопиримидины |
| EP2215093B1 (de) | 2007-10-19 | 2011-12-14 | Boehringer Ingelheim International GmbH | Neue piperazino-dihydrothienopyrimidin-derivate |
| SI2610258T1 (sl) * | 2007-10-19 | 2014-12-31 | Boehringer Ingelheim International Gmbh | Substituirani piperidino-dihidrotienopirimidini |
| ES2523169T3 (es) | 2008-01-25 | 2014-11-21 | High Point Pharmaceuticals, Llc | Compuestos tricíclicos como moduladores de la síntesis de TNF y como inhibidores de PDE4 |
| WO2010097332A1 (de) * | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
| GB2477590A (en) * | 2010-02-05 | 2011-08-10 | Biocopea Ltd | A non-steroidal anti-inflammatory drug (NSAID) formulation comprising a lipid carrier |
| US11730709B2 (en) | 2010-10-29 | 2023-08-22 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
| US11202831B2 (en) | 2010-10-29 | 2021-12-21 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
| US9737500B2 (en) | 2010-10-29 | 2017-08-22 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
| US9271950B2 (en) | 2010-10-29 | 2016-03-01 | Infirst Healthcare Limited | Compositions for treating chronic inflammation and inflammatory diseases |
| US10695432B2 (en) | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in severe pain |
| US9308213B2 (en) | 2010-10-29 | 2016-04-12 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
| US9744132B2 (en) | 2010-10-29 | 2017-08-29 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
| US11224659B2 (en) | 2010-10-29 | 2022-01-18 | Infirst Healthcare Limited | Solid solution compositions and use in severe pain |
| US8895537B2 (en) | 2010-10-29 | 2014-11-25 | Infirst Healthcare Ltd. | Compositions and methods for treating cardiovascular diseases |
| US9504664B2 (en) | 2010-10-29 | 2016-11-29 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
| US10695431B2 (en) | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
| US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
| US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| WO2014066659A1 (en) | 2012-10-25 | 2014-05-01 | Tetra Discovery Partners, Llc. | Heteroaryl inhibitors of pde4 |
| MX2015009678A (es) | 2013-02-04 | 2015-11-25 | Gruenenthal Gmbh | Compuestos de pirimidina condensada sustituida con amino en la posicion 4 como inhibidores de fosfodiesterasa 4 (pde4). |
| WO2014124860A1 (en) | 2013-02-14 | 2014-08-21 | Boehringer Ingelheim International Gmbh | Specific pde4b-inhibitors for the treatment of diabetes mellitus |
| WO2016139212A1 (en) * | 2015-03-04 | 2016-09-09 | F. Hoffmann-La Roche Ag | Triazolopyridine compounds and methods of use thereof |
| US11365204B2 (en) | 2017-09-20 | 2022-06-21 | UNION therapeutics A/S | Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| WO2019115775A1 (en) * | 2017-12-15 | 2019-06-20 | Leo Pharma A/S | Substituted tetrahydropyran dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| WO2019115774A1 (en) * | 2017-12-15 | 2019-06-20 | Leo Pharma A/S | Substituted azetidine dihydrothienopyrimidines and their use as phosphodiesterase inhibitors |
| WO2019115776A1 (en) * | 2017-12-15 | 2019-06-20 | Leo Pharma A/S | Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors |
| WO2019147824A1 (en) | 2018-01-26 | 2019-08-01 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a pde4 inhibitor |
| CN113348011B (zh) | 2018-11-19 | 2023-04-18 | 比奥拉治疗股份有限公司 | 用生物治疗剂治疗疾病的方法和装置 |
| CN121197633A (zh) | 2019-12-13 | 2025-12-26 | 比特比德科有限责任公司 | 用于将治疗剂递送至胃肠道的可摄取装置 |
| CN113861189A (zh) | 2020-06-29 | 2021-12-31 | Vtv治疗有限责任公司 | 喹啉衍生物，其药学上可接受的盐及其使用方法 |
| US12545676B2 (en) | 2020-07-28 | 2026-02-10 | Vtv Therapeutics Llc | Crystalline form of hydrochloride salt of quinoline derivative |
| JP2025528779A (ja) * | 2022-08-09 | 2025-09-02 | シーザン ハイスーク ファーマシューティカル カンパニー リミテッド | Ｐｄｅ４ｂ阻害剤及びその用途 |
| CN121127461A (zh) * | 2023-04-03 | 2025-12-12 | 上海壹迪生物技术有限公司 | 二氢噻吩并嘧啶类化合物、其制备方法和应用 |
| EP4761728A2 (en) * | 2023-08-17 | 2026-06-24 | Katalytic Therapeutics, Inc. | Pde4 protein degraders, pharmaceutical compositions, and therapeutic applications |
| WO2025067168A1 (zh) * | 2023-09-25 | 2025-04-03 | 苏州爱科百发生物医药技术有限公司 | 氮杂稠环类化合物及其制备方法和用途 |
| CN120398908A (zh) * | 2024-02-01 | 2025-08-01 | 艾派克斯生物科技有限公司 | Pde4b抑制剂及其药物组合物和用途 |
| WO2025162289A2 (zh) * | 2024-02-04 | 2025-08-07 | 西藏海思科制药有限公司 | 一种pde4b抑制剂的晶型及其在医药上的用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5491201A (en) | 1992-02-06 | 1996-02-13 | The Dow Chemical Company | Mesogenic cyclic imino ether-containing compositions and polymerization products thereof |
| DE9418068U1 (de) | 1994-11-11 | 1995-01-12 | Hoppe AG, 35260 Stadtallendorf | Getriebegriff |
| IL150963A0 (en) * | 2000-02-08 | 2003-02-12 | Smithkline Beecham Corp | Method and compositions for treating an inflammatory disease |
| IL160271A0 (en) * | 2001-09-19 | 2004-07-25 | Altana Pharma Ag | Pharmaceutical compositions containing pde4-inhibitors and nsaid |
| WO2005061483A2 (en) | 2003-12-23 | 2005-07-07 | Bio-Medisinsk Innovasjon As | Modulators of peripheral 5-ht receptors |
| US20080171746A1 (en) | 2005-03-14 | 2008-07-17 | Thomas Klein | Method for Preventing Cardiovascular Diseases |
| WO2007106705A1 (en) | 2006-03-10 | 2007-09-20 | Boehringer Ingelheim International Gmbh | Soluble epoxide hydrolase inhibitors and methods of using same |
| HRP20090395T1 (hr) | 2006-04-19 | 2009-08-31 | Boehringer Ingelheim International Gmbh | Dihidrotienpirimidini za liječenje upalnih bolesti |
| SI2610258T1 (sl) * | 2007-10-19 | 2014-12-31 | Boehringer Ingelheim International Gmbh | Substituirani piperidino-dihidrotienopirimidini |
| WO2010097332A1 (de) * | 2009-02-27 | 2010-09-02 | Boehringer Ingelheim International Gmbh | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
-
2010
- 2010-02-18 JP JP2011551465A patent/JP2012519160A/ja active Pending
- 2010-02-18 WO PCT/EP2010/052079 patent/WO2010097334A1/de not_active Ceased
- 2010-02-18 US US13/201,270 patent/US9161927B2/en active Active
- 2010-02-18 CA CA2753604A patent/CA2753604A1/en not_active Abandoned
- 2010-02-18 EP EP10704932.2A patent/EP2400962B1/de active Active
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