CA2399840C - Use of roflumilast or pumafentrine in combination with methotrexate for the treatment of arthritic diseases - Google Patents
Use of roflumilast or pumafentrine in combination with methotrexate for the treatment of arthritic diseases Download PDFInfo
- Publication number
- CA2399840C CA2399840C CA2399840A CA2399840A CA2399840C CA 2399840 C CA2399840 C CA 2399840C CA 2399840 A CA2399840 A CA 2399840A CA 2399840 A CA2399840 A CA 2399840A CA 2399840 C CA2399840 C CA 2399840C
- Authority
- CA
- Canada
- Prior art keywords
- rheumatic
- methyl
- drug
- pde4
- pde3
- 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 - Fee Related
Links
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 title claims description 40
- 238000011282 treatment Methods 0.000 title claims description 38
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 title claims description 21
- 229960002586 roflumilast Drugs 0.000 title claims description 21
- CVDXFPBVOIERBH-JWQCQUIFSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n,n-di(propan-2-yl)benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 CVDXFPBVOIERBH-JWQCQUIFSA-N 0.000 title claims description 20
- 229950010090 pumafentrine Drugs 0.000 title claims description 20
- 229960000485 methotrexate Drugs 0.000 title claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 42
- 230000002917 arthritic effect Effects 0.000 title description 12
- 201000010099 disease Diseases 0.000 title description 9
- 239000002988 disease modifying antirheumatic drug Substances 0.000 claims abstract description 117
- 239000003435 antirheumatic agent Substances 0.000 claims abstract description 85
- 229940123907 Disease modifying antirheumatic drug Drugs 0.000 claims abstract description 82
- 239000003112 inhibitor Substances 0.000 claims abstract description 58
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims abstract description 54
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims abstract description 54
- 101100135868 Dictyostelium discoideum pde3 gene Proteins 0.000 claims abstract description 52
- 229940124347 antiarthritic drug Drugs 0.000 claims abstract description 49
- 230000003356 anti-rheumatic effect Effects 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims description 26
- -1 2,4-diamino-6-pteridinyl Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 15
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
- 239000002552 dosage form Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- CVDXFPBVOIERBH-DQEYMECFSA-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-di(propan-2-yl)benzamide Chemical compound N([C@H]1CCN(C)C[C@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 CVDXFPBVOIERBH-DQEYMECFSA-N 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 40
- 208000035475 disorder Diseases 0.000 description 33
- 241000699670 Mus sp. Species 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 8
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 8
- VXIHRIQNJCRFQX-UHFFFAOYSA-K disodium aurothiomalate Chemical compound [Na+].[Na+].[O-]C(=O)CC(S[Au])C([O-])=O VXIHRIQNJCRFQX-UHFFFAOYSA-K 0.000 description 8
- 238000011160 research Methods 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- 208000009386 Experimental Arthritis Diseases 0.000 description 7
- 206010003246 arthritis Diseases 0.000 description 7
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 7
- HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 description 6
- 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 6
- 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 6
- 108010029485 Protein Isoforms Proteins 0.000 description 6
- 102000001708 Protein Isoforms Human genes 0.000 description 6
- 229960004238 anakinra Drugs 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000002464 receptor antagonist Substances 0.000 description 6
- 229940044551 receptor antagonist Drugs 0.000 description 6
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 5
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 5
- 239000000306 component Substances 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 4
- JEXXKWQSTOIMJW-UHFFFAOYSA-N 5-methyl-n-[4-(trifluoromethyl)phenyl]-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=N1 JEXXKWQSTOIMJW-UHFFFAOYSA-N 0.000 description 4
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 4
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 4
- 229930105110 Cyclosporin A Natural products 0.000 description 4
- 108010036949 Cyclosporine Proteins 0.000 description 4
- GZENKSODFLBBHQ-ILSZZQPISA-N Medrysone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 GZENKSODFLBBHQ-ILSZZQPISA-N 0.000 description 4
- HYRKAAMZBDSJFJ-LFDBJOOHSA-N Paramethasone acetate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]2(C)C[C@@H]1O HYRKAAMZBDSJFJ-LFDBJOOHSA-N 0.000 description 4
- AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 description 4
- 229960005207 auranofin Drugs 0.000 description 4
- 229960002170 azathioprine Drugs 0.000 description 4
- 229960001265 ciclosporin Drugs 0.000 description 4
- 229960004544 cortisone Drugs 0.000 description 4
- 229960004397 cyclophosphamide Drugs 0.000 description 4
- 229930182912 cyclosporin Natural products 0.000 description 4
- AAXVEMMRQDVLJB-BULBTXNYSA-N fludrocortisone Chemical compound O=C1CC[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 AAXVEMMRQDVLJB-BULBTXNYSA-N 0.000 description 4
- 229960004171 hydroxychloroquine Drugs 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 229960000598 infliximab Drugs 0.000 description 4
- NPGREARFJMFTDF-UHFFFAOYSA-N n-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)N=C1C(Cl)=CN(O)C=C1Cl NPGREARFJMFTDF-UHFFFAOYSA-N 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229960001315 sodium aurothiomalate Drugs 0.000 description 4
- DDYUBCCTNHWSQM-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(1,3-dioxoisoindol-2-yl)propanamide Chemical compound COC1=CC=C(C(CC(N)=O)N2C(C3=CC=CC=C3C2=O)=O)C=C1OC1CCCC1 DDYUBCCTNHWSQM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OALFSCJVHJUFDL-DKIIUIKKSA-N Cl.C(C)OC1=CC2=C(C(=N[C@H]3CCN(C[C@@H]23)C)C2=CC=C(C=C2)C(=O)N(C(C)C)C(C)C)C=C1OC Chemical compound Cl.C(C)OC1=CC2=C(C(=N[C@H]3CCN(C[C@@H]23)C)C2=CC=C(C=C2)C(=O)N(C(C)C)C(C)C)C=C1OC OALFSCJVHJUFDL-DKIIUIKKSA-N 0.000 description 3
- WYQPLTPSGFELIB-JTQPXKBDSA-N Difluprednate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2CC[C@@](C(=O)COC(C)=O)(OC(=O)CCC)[C@@]2(C)C[C@@H]1O WYQPLTPSGFELIB-JTQPXKBDSA-N 0.000 description 3
- 108010008165 Etanercept Proteins 0.000 description 3
- 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
- 102000009270 Tumour necrosis factor alpha Human genes 0.000 description 3
- 108050000101 Tumour necrosis factor alpha Proteins 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- FBHSPRKOSMHSIF-GRMWVWQJSA-N deflazacort Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)=N[C@@]3(C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O FBHSPRKOSMHSIF-GRMWVWQJSA-N 0.000 description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960000403 etanercept Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960002744 mometasone furoate Drugs 0.000 description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 3
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- ISNWPDWXSHAYEL-KTORGGLSSA-N (6s,8s,9s,10r,13s,14s,17s)-17-acetyl-6,10,13-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 ISNWPDWXSHAYEL-KTORGGLSSA-N 0.000 description 2
- XAFHBOWMCANBEX-KXSVHEDMSA-N 2-oxo-2-[(6s,8s,9s,10r,13s,14s,17s)-6,10,13-trimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]acetic acid Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)C(O)=O)CC[C@H]21 XAFHBOWMCANBEX-KXSVHEDMSA-N 0.000 description 2
- MIXLZCYFMQNQDD-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-N'-hydroxy-1,3-thiazole-2-carboximidamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(C(N)=NO)=N1 MIXLZCYFMQNQDD-UHFFFAOYSA-N 0.000 description 2
- CFBUZOUXXHZCFB-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid Chemical compound COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-UHFFFAOYSA-N 0.000 description 2
- TZBDXWBBMOEVPI-XBQQDWOSSA-N 58524-83-7 Chemical compound O=C([C@]12[C@@]3(C)C[C@H](O)[C@]4(F)[C@@]5(C)C=CC(=O)C=C5[C@@H](F)C[C@H]4[C@@H]3C[C@H]1OC(O2)(C)C)COC(=O)C1CC1 TZBDXWBBMOEVPI-XBQQDWOSSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 description 2
- PUWHHWCHAVXSIG-NCLPIGKXSA-N Fluocortin Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)C(O)=O)[C@@]2(C)C[C@@H]1O PUWHHWCHAVXSIG-NCLPIGKXSA-N 0.000 description 2
- POPFMWWJOGLOIF-XWCQMRHXSA-N Flurandrenolide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O POPFMWWJOGLOIF-XWCQMRHXSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 2
- HZQDCMWJEBCWBR-UUOKFMHZSA-N Mizoribine Chemical compound OC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HZQDCMWJEBCWBR-UUOKFMHZSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NVVPAUWWHNAOSO-KTPDAARESA-N OC1=CC(C=C2C(C[C@H]3[C@@H]4CC[C@](C(C)=O)([C@]4(CC[C@@H]3[C@@]12C)C)O)C)=O Chemical compound OC1=CC(C=C2C(C[C@H]3[C@@H]4CC[C@](C(C)=O)([C@]4(CC[C@@H]3[C@@]12C)C)O)C)=O NVVPAUWWHNAOSO-KTPDAARESA-N 0.000 description 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010054094 Tumour necrosis Diseases 0.000 description 2
- UYVYDRXVNVNQEA-BJTOFBPUSA-N [2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 4-(acetamidomethyl)cyclohexane-1-carboxylate Chemical compound O=C([C@]1(O)[C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@@H]1C)COC(=O)C1CCC(CNC(C)=O)CC1 UYVYDRXVNVNQEA-BJTOFBPUSA-N 0.000 description 2
- YPFLFUJKZDAXRA-UHFFFAOYSA-N [3-(carbamoylamino)-2-(2,4-dichlorobenzoyl)-1-benzofuran-6-yl] methanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C)=CC=C2C(NC(N)=O)=C1C(=O)C1=CC=C(Cl)C=C1Cl YPFLFUJKZDAXRA-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 229960000552 alclometasone Drugs 0.000 description 2
- FJXOGVLKCZQRDN-PHCHRAKRSA-N alclometasone Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O FJXOGVLKCZQRDN-PHCHRAKRSA-N 0.000 description 2
- 230000002456 anti-arthritic effect Effects 0.000 description 2
- GVTLDPJNRVMCAL-UHFFFAOYSA-N arofylline Chemical compound C1=2N=CNC=2C(=O)N(CCC)C(=O)N1C1=CC=C(Cl)C=C1 GVTLDPJNRVMCAL-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 229950002649 ciprocinonide Drugs 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 229960001145 deflazacort Drugs 0.000 description 2
- 230000001934 delay Effects 0.000 description 2
- 229960002593 desoximetasone Drugs 0.000 description 2
- VWVSBHGCDBMOOT-IIEHVVJPSA-N desoximetasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@@H]2O VWVSBHGCDBMOOT-IIEHVVJPSA-N 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- 229960004875 difluprednate Drugs 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229960002011 fludrocortisone Drugs 0.000 description 2
- 229960004511 fludroxycortide Drugs 0.000 description 2
- 229960000676 flunisolide Drugs 0.000 description 2
- 229960001347 fluocinolone acetonide Drugs 0.000 description 2
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 2
- 229960000785 fluocinonide Drugs 0.000 description 2
- 229960005355 fluocortin Drugs 0.000 description 2
- GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 2
- 229960001048 fluorometholone Drugs 0.000 description 2
- FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 description 2
- 229960003238 fluprednidene Drugs 0.000 description 2
- YVHXHNGGPURVOS-SBTDHBFYSA-N fluprednidene Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](C(=C)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 YVHXHNGGPURVOS-SBTDHBFYSA-N 0.000 description 2
- 229960002383 halcinonide Drugs 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229960001011 medrysone Drugs 0.000 description 2
- 229960004584 methylprednisolone Drugs 0.000 description 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- RELJWHOMJUFVIO-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[5-fluoro-1-[(4-fluorophenyl)methyl]indol-3-yl]-2-oxoacetamide Chemical compound C1=CC(F)=CC=C1CN1C2=CC=C(F)C=C2C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)=C1 RELJWHOMJUFVIO-UHFFFAOYSA-N 0.000 description 2
- 229960000865 paramethasone acetate Drugs 0.000 description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 2
- ILZSJEITWDWIRX-FOMYWIRZSA-N prednisolamate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CN(CC)CC)(O)[C@@]1(C)C[C@@H]2O ILZSJEITWDWIRX-FOMYWIRZSA-N 0.000 description 2
- 229950011122 prednisolamate Drugs 0.000 description 2
- 229960005205 prednisolone Drugs 0.000 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 229960001917 prednylidene Drugs 0.000 description 2
- WSVOMANDJDYYEY-CWNVBEKCSA-N prednylidene Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](C(=C)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WSVOMANDJDYYEY-CWNVBEKCSA-N 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- IUWKNLFTJBHTSD-AANPDWTMSA-N promestriene Chemical compound C1C[C@]2(C)[C@@H](OC)CC[C@H]2[C@@H]2CCC3=CC(OCCC)=CC=C3[C@H]21 IUWKNLFTJBHTSD-AANPDWTMSA-N 0.000 description 2
- 229960004765 promestriene Drugs 0.000 description 2
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- VUAFHZCUKUDDBC-SCSAIBSYSA-N (2s)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid Chemical compound CC(C)(S)C(=O)N[C@H](CS)C(O)=O VUAFHZCUKUDDBC-SCSAIBSYSA-N 0.000 description 1
- LGFLRHWJJKLPCC-ZDUSSCGKSA-N (2s)-2-[[4-[2-(2,4-diaminopteridin-6-yl)ethyl]benzoyl]amino]pentanedioic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 LGFLRHWJJKLPCC-ZDUSSCGKSA-N 0.000 description 1
- AKTXOQVMWSFEBQ-LCYFTJDESA-N (5z)-2-amino-5-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(\C=C/2C(N=C(N)S\2)=O)=C1 AKTXOQVMWSFEBQ-LCYFTJDESA-N 0.000 description 1
- JANOHXQLZGWZKW-NTNOATJHSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-6-methylidene-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-3-one Chemical compound C=C1C[C@H]2[C@@H]3CC[C@H](C(C)=O)[C@]3(CC[C@@H]2[C@]2(C=CC(C=C12)=O)C)C JANOHXQLZGWZKW-NTNOATJHSA-N 0.000 description 1
- ISNWPDWXSHAYEL-RTDHNQHTSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-6,10,13-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)=CC(=O)C=C1C(C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 ISNWPDWXSHAYEL-RTDHNQHTSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- LITNEAPWQHVPOK-FFSVYQOJSA-N 2(1h)-pyrimidinone, 5-[3-[(1s,2s,4r)-bicyclo[2.2.1]hept-2-yloxy]-4-methoxyphenyl]tetrahydro- Chemical compound C1=C(O[C@@H]2[C@H]3CC[C@H](C3)C2)C(OC)=CC=C1C1CNC(=O)NC1 LITNEAPWQHVPOK-FFSVYQOJSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QCFOHJJGMFEJSE-UHFFFAOYSA-N 2-[8-chloro-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-6-yl]acetic acid Chemical compound N1C(C(F)(F)F)CCC2=CC(CC(=O)O)=CC(Cl)=C21 QCFOHJJGMFEJSE-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- CGFRGBQJWVFTRF-UHFFFAOYSA-N 3-[(3-cyclopentyloxy-4-methoxyphenyl)methyl]-n-ethyl-8-propan-2-ylpurin-6-amine Chemical compound C12=NC(C(C)C)=NC2=C(NCC)N=CN1CC(C=1)=CC=C(OC)C=1OC1CCCC1 CGFRGBQJWVFTRF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RHQGNGVPYGWSJI-UHFFFAOYSA-N 3-cyclopropyl-n-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)-2-methoxybenzamide Chemical compound COC1=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=CC(OC(F)F)=C1C1CC1 RHQGNGVPYGWSJI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 206010052613 Allergic bronchitis Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- ISNWPDWXSHAYEL-PFOMDNQCSA-N C[C@@H]1C[C@H]2[C@@H]3CC[C@H](C(C)=O)[C@]3(CC[C@@H]2[C@]2(C=CC(C=C12)=O)C)C Chemical compound C[C@@H]1C[C@H]2[C@@H]3CC[C@H](C(C)=O)[C@]3(CC[C@@H]2[C@]2(C=CC(C=C12)=O)C)C ISNWPDWXSHAYEL-PFOMDNQCSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010009137 Chronic sinusitis Diseases 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 102000000503 Collagen Type II Human genes 0.000 description 1
- 108010041390 Collagen Type II Proteins 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- QIEPWCSVQYUPIY-LEKSSAKUSA-N Delta(1)-progesterone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QIEPWCSVQYUPIY-LEKSSAKUSA-N 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- ANMATWQYLIFGOK-UHFFFAOYSA-N Iguratimod Chemical compound CS(=O)(=O)NC1=CC=2OC=C(NC=O)C(=O)C=2C=C1OC1=CC=CC=C1 ANMATWQYLIFGOK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- 239000004201 L-cysteine Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- RBCGOSAFAPGFGD-UHFFFAOYSA-N [2-(4-methylphenyl)-1,3-benzothiazol-4-yl] acetate Chemical compound N=1C=2C(OC(=O)C)=CC=CC=2SC=1C1=CC=C(C)C=C1 RBCGOSAFAPGFGD-UHFFFAOYSA-N 0.000 description 1
- HSJYWBXYCFIGLA-UHFFFAOYSA-N [5-[(3-cyclopentyloxy-4-methoxyphenyl)methylamino]-1h-pyrazol-4-yl]methanol Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1CNC1=NNC=C1CO HSJYWBXYCFIGLA-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 208000004631 alopecia areata Diseases 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229950009746 arofylline Drugs 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- SERHTTSLBVGRBY-UHFFFAOYSA-N atiprimod Chemical compound C1CC(CCC)(CCC)CCC11CN(CCCN(CC)CC)CC1 SERHTTSLBVGRBY-UHFFFAOYSA-N 0.000 description 1
- 229950006944 atizoram Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229960004272 bucillamine Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000546 chi-square test Methods 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 201000009151 chronic rhinitis Diseases 0.000 description 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 description 1
- 229950001653 cilomilast Drugs 0.000 description 1
- KSPYMJJKQMWWNB-UHFFFAOYSA-N cipamfylline Chemical compound O=C1N(CC2CC2)C(=O)C=2NC(N)=NC=2N1CC1CC1 KSPYMJJKQMWWNB-UHFFFAOYSA-N 0.000 description 1
- 229950002405 cipamfylline Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 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 description 1
- 229950000393 darbufelone Drugs 0.000 description 1
- PCCPERGCFKIYIS-AWEZNQCLSA-N daxalipram Chemical compound C1=C(OC)C(OCCC)=CC([C@@]2(C)OC(=O)NC2)=C1 PCCPERGCFKIYIS-AWEZNQCLSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229960003973 fluocortolone Drugs 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 229960002475 halometasone Drugs 0.000 description 1
- GGXMRPUKBWXVHE-MIHLVHIWSA-N halometasone Chemical compound C1([C@@H](F)C2)=CC(=O)C(Cl)=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O GGXMRPUKBWXVHE-MIHLVHIWSA-N 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229950000844 mizoribine Drugs 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- DPHDSIQHVGSITN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxyindol-3-yl]-2-oxoacetamide Chemical compound C1=C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 DPHDSIQHVGSITN-UHFFFAOYSA-N 0.000 description 1
- QUVHZANTGRHKML-UHFFFAOYSA-N n-[1-[4-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]phenyl]cyclopropyl]acetamide Chemical compound C=1C=C(CN2CCN(CC2)C=2N=CC=CN=2)C=CC=1C1(NC(=O)C)CC1 QUVHZANTGRHKML-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 210000001331 nose Anatomy 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
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- 229960002858 paramethasone Drugs 0.000 description 1
- 210000003695 paranasal sinus Anatomy 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 238000002821 scintillation proximity assay Methods 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- 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
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P11/08—Bronchodilators
-
- 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
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01000607 | 2001-11-09 | ||
| EP01000607.0 | 2001-11-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2399840A1 CA2399840A1 (en) | 2003-05-09 |
| CA2399840C true CA2399840C (en) | 2010-10-19 |
Family
ID=8176085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2399840A Expired - Fee Related CA2399840C (en) | 2001-11-09 | 2002-08-27 | Use of roflumilast or pumafentrine in combination with methotrexate for the treatment of arthritic diseases |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20030092706A1 (enExample) |
| EP (1) | EP1448202A1 (enExample) |
| JP (1) | JP2005508983A (enExample) |
| AU (1) | AU2002300754B2 (enExample) |
| CA (1) | CA2399840C (enExample) |
| WO (1) | WO2003039552A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7718644B2 (en) * | 2004-01-22 | 2010-05-18 | The Trustees Of Columbia University In The City Of New York | Anti-arrhythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) and uses thereof |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| HUE039709T2 (hu) * | 2002-05-28 | 2019-01-28 | Astrazeneca Ab | Helyileg alkalmazandó gyógyászati készítmény |
| US6727272B1 (en) * | 2002-07-15 | 2004-04-27 | Unitech Pharmaceuticals, Inc. | Leflunomide analogs for treating rheumatoid arthritis |
| UA82323C2 (uk) * | 2002-08-09 | 2008-04-10 | Меда Фарма Гмбх & Ко. Кг | Нова комбінація глюкокортикоїду та pde-інгібітору для лікування респіраторних захворювань, алергічних захворювань, астми та хронічних обструктивних легеневих захворювань |
| ES2335498T3 (es) | 2003-03-10 | 2010-03-29 | Nycomed Gmbh | Nuevo proceso para la preparacion de reflumilast. |
| US20070254928A1 (en) * | 2004-05-10 | 2007-11-01 | Altana Pharma Ag | Use of Roflumilast for the Prophylaxis or Treatment of Emphysema |
| WO2006049215A1 (ja) * | 2004-11-02 | 2006-05-11 | Dainippon Sumitomo Pharma Co., Ltd. | 自己免疫疾患を治療するための併用薬 |
| US8242149B2 (en) * | 2005-03-11 | 2012-08-14 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| EP2258350B1 (en) * | 2005-03-16 | 2014-12-24 | Takeda GmbH | Taste masked dosage form containing roflumilast |
| KR100838702B1 (ko) * | 2007-02-08 | 2008-06-16 | 한국화학연구원 | 1-[1-(3,4-디알콕시아릴)-피리딜메틸]-1ｈ-피라졸 화합물의제조방법 |
| WO2010091381A2 (en) * | 2009-02-09 | 2010-08-12 | Callisto Pharmaceuticals, Inc. | An intermittent dosing strategy for treating rheumatoid arthrtis |
| EP2736489A4 (en) * | 2011-07-28 | 2015-01-14 | Cellworks Res India Private Ltd | COMPOSITIONS, METHOD FOR THE PRODUCTION THEREOF, AND METHOD FOR THE TREATMENT OF INFLAMMATORY DISEASES |
| EA201591360A1 (ru) | 2013-02-19 | 2016-03-31 | Пфайзер Инк. | Азабензимидазолы в качестве ингибиторов изозимов фдэ4 для лечения цнс и других расстройств |
| EP3172210B1 (en) | 2014-07-24 | 2020-01-15 | Pfizer Inc | Pyrazolopyrimidine compounds |
| PT3177624T (pt) | 2014-08-06 | 2019-07-11 | Pfizer | Compostos de imidazopiridazina |
| US11977085B1 (en) | 2023-09-05 | 2024-05-07 | Elan Ehrlich | Date rape drug detection device and method of using same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1161239E (pt) * | 1999-03-10 | 2005-02-28 | Altana Pharma Ag | 3-ciclopropilmetoxi-4-difluorometoxi-n-(3,5-dicloropirid-4-il)-benzamida para o tratamento da esclerose multipla |
-
2002
- 2002-06-28 US US10/184,068 patent/US20030092706A1/en not_active Abandoned
- 2002-08-27 AU AU2002300754A patent/AU2002300754B2/en not_active Ceased
- 2002-08-27 CA CA2399840A patent/CA2399840C/en not_active Expired - Fee Related
- 2002-11-07 EP EP02792742A patent/EP1448202A1/en not_active Withdrawn
- 2002-11-07 WO PCT/EP2002/012415 patent/WO2003039552A1/en not_active Ceased
- 2002-11-07 JP JP2003541843A patent/JP2005508983A/ja active Pending
-
2007
- 2007-07-19 US US11/826,876 patent/US20070270441A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005508983A (ja) | 2005-04-07 |
| US20070270441A1 (en) | 2007-11-22 |
| WO2003039552A1 (en) | 2003-05-15 |
| AU2002300754B2 (en) | 2008-05-15 |
| EP1448202A1 (en) | 2004-08-25 |
| CA2399840A1 (en) | 2003-05-09 |
| US20030092706A1 (en) | 2003-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20070270441A1 (en) | Combination | |
| US12329753B2 (en) | Phosphodiesterase inhibitor treatment | |
| US20240366578A1 (en) | Treatment of pain and vasoconstriction | |
| US20060083714A1 (en) | Combination of a pde iv inhibitor and a tnf-alpha antagonist | |
| RS52730B (sr) | Kompozicija koja sadrži pde4 inhibitor i pde5 inhibitor | |
| WO2021216754A1 (en) | Use of p38 mapk inhibitors for prevention and treatment of aging and aging-related disorders and for boosting an immune system | |
| JP2024178420A (ja) | 多発性硬化症を治療するためのｌｏｕ０６４ | |
| JP2005508983A5 (enExample) | ||
| JP2007526285A (ja) | Ｐｄｅ５阻害剤のための新規の使用 | |
| US11744829B2 (en) | Methods for treating neurological conditions and exposure to nerve agents | |
| JP2023536944A (ja) | 疾患の治療におけるｂｔｋ阻害剤の使用 | |
| AU2018290288A1 (en) | Epichaperome inhibitor therapy for traumatic brain injury and sequelae thereof | |
| US20250017878A1 (en) | Use of nadolol to treat chronic obstructive pulmonary disease by blockage of the arrestin-2 pathway | |
| WO2020014072A1 (en) | Neostigmine pharmaceutical combination for treating myasthenia gravis | |
| WO2023034466A1 (en) | Cgrp antagonists for treating psoriasis | |
| EP4316518A1 (en) | Drug combination of toll-like receptor 7 agonist and anti-pd-l1 antibody | |
| TW202421196A (zh) | 免疫性血小板減少症之治療 | |
| KR20230171918A (ko) | 소아-발병 유창성 장애의 치료 방법 | |
| CN117157077A (zh) | 儿童期发病的流畅性障碍的治疗方法 | |
| WO2019023318A1 (en) | PHARMACEUTICAL COMPOSITIONS AND METHODS USING PYRIDOSTIGMINE AND AN ANTAGONIST OF NK-1 FOR TREATING SEVERE MYASTHENIA |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160829 |