ZA200407104B - Pharmaceutical composition of a PDE4 of a PDE3/4 inhibitor and a histamine receptor antagonist - Google Patents
Pharmaceutical composition of a PDE4 of a PDE3/4 inhibitor and a histamine receptor antagonist Download PDFInfo
- Publication number
- ZA200407104B ZA200407104B ZA200407104A ZA200407104A ZA200407104B ZA 200407104 B ZA200407104 B ZA 200407104B ZA 200407104 A ZA200407104 A ZA 200407104A ZA 200407104 A ZA200407104 A ZA 200407104A ZA 200407104 B ZA200407104 B ZA 200407104B
- Authority
- ZA
- South Africa
- Prior art keywords
- inn
- phthalazin
- tetrahydro
- piperidin
- methyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 37
- 101100135868 Dictyostelium discoideum pde3 gene Proteins 0.000 title claims description 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 35
- 229940122236 Histamine receptor antagonist Drugs 0.000 title claims description 30
- 239000000739 antihistaminic agent Substances 0.000 title claims description 24
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 title description 13
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 title description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
- 239000004480 active ingredient Substances 0.000 claims description 75
- 239000002253 acid Substances 0.000 claims description 63
- SFOVDSLXFUGAIV-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-piperidin-4-ylbenzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCNCC1 SFOVDSLXFUGAIV-UHFFFAOYSA-N 0.000 claims description 54
- -1 1C-485 Chemical compound 0.000 claims description 46
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims description 46
- 238000002360 preparation method Methods 0.000 claims description 45
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 43
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 claims description 40
- 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 39
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 35
- 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 claims description 34
- 229960001271 desloratadine Drugs 0.000 claims description 33
- DIGXMFZQXQUVMR-UHFFFAOYSA-N 5-hexyl-7-(methylsulfonimidoyl)-9-oxoxanthene-2-carboxylic acid Chemical compound O1C2=CC=C(C(O)=O)C=C2C(=O)C2=C1C(CCCCCC)=CC(S(C)(=N)=O)=C2 DIGXMFZQXQUVMR-UHFFFAOYSA-N 0.000 claims description 31
- 229960003088 loratadine Drugs 0.000 claims description 31
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 30
- 229960001803 cetirizine Drugs 0.000 claims description 30
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 29
- 229960004574 azelastine Drugs 0.000 claims description 29
- 229960000351 terfenadine Drugs 0.000 claims description 28
- 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 claims description 27
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 27
- KBUZBQVCBVDWKX-UHFFFAOYSA-N emedastine Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1N1CCCN(C)CC1 KBUZBQVCBVDWKX-UHFFFAOYSA-N 0.000 claims description 27
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 27
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- PWACSDKDOHSSQD-IUTFFREVSA-N acrivastine Chemical compound C1=CC(C)=CC=C1C(\C=1N=C(\C=C\C(O)=O)C=CC=1)=C/CN1CCCC1 PWACSDKDOHSSQD-IUTFFREVSA-N 0.000 claims description 25
- 229960003592 fexofenadine Drugs 0.000 claims description 25
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 25
- 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 claims description 24
- 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 claims description 24
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 claims description 24
- HIANJWSAHKJQTH-UHFFFAOYSA-N pemirolast Chemical compound CC1=CC=CN(C2=O)C1=NC=C2C=1N=NNN=1 HIANJWSAHKJQTH-UHFFFAOYSA-N 0.000 claims description 24
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- MJJALKDDGIKVBE-UHFFFAOYSA-N ebastine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)CCCN1CCC(OC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MJJALKDDGIKVBE-UHFFFAOYSA-N 0.000 claims description 23
- 229950010090 pumafentrine Drugs 0.000 claims description 23
- 229960002586 roflumilast Drugs 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 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 claims description 22
- PVLJETXTTWAYEW-UHFFFAOYSA-N Mizolastine Chemical compound N=1C=CC(=O)NC=1N(C)C(CC1)CCN1C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 PVLJETXTTWAYEW-UHFFFAOYSA-N 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229960001144 mizolastine Drugs 0.000 claims description 22
- YWGDOWXRIALTES-NRFANRHFSA-N bepotastine Chemical compound C1CN(CCCC(=O)O)CCC1O[C@H](C=1N=CC=CC=1)C1=CC=C(Cl)C=C1 YWGDOWXRIALTES-NRFANRHFSA-N 0.000 claims description 21
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 21
- 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 claims description 20
- KSPYMJJKQMWWNB-UHFFFAOYSA-N cipamfylline Chemical compound O=C1N(CC2CC2)C(=O)C=2NC(N)=NC=2N1CC1CC1 KSPYMJJKQMWWNB-UHFFFAOYSA-N 0.000 claims description 20
- BAWMMJAUVBLLEE-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BAWMMJAUVBLLEE-UHFFFAOYSA-N 0.000 claims description 19
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 claims description 19
- 229960002881 clemastine Drugs 0.000 claims description 19
- 229950003420 efletirizine Drugs 0.000 claims description 19
- 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 claims description 19
- WUZYKBABMWJHDL-UHFFFAOYSA-N rupatadine Chemical compound CC1=CN=CC(CN2CCC(CC2)=C2C3=NC=CC=C3CCC3=CC(Cl)=CC=C32)=C1 WUZYKBABMWJHDL-UHFFFAOYSA-N 0.000 claims description 19
- VBSPHZOBAOWFCL-UHFFFAOYSA-N setastine Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C)OCCN1CCCCCC1 VBSPHZOBAOWFCL-UHFFFAOYSA-N 0.000 claims description 19
- 229950003911 setastine Drugs 0.000 claims description 19
- ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 claims description 18
- UFLGIAIHIAPJJC-UHFFFAOYSA-N Tripelennamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 UFLGIAIHIAPJJC-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 18
- 229960002071 bepotastine Drugs 0.000 claims description 18
- 229960000325 emedastine Drugs 0.000 claims description 18
- 229960001120 levocabastine Drugs 0.000 claims description 18
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 claims description 18
- 229960001508 levocetirizine Drugs 0.000 claims description 18
- 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 claims description 18
- 229960005328 rupatadine Drugs 0.000 claims description 18
- 229960003223 tripelennamine Drugs 0.000 claims description 18
- CWNCDQYLHMXURI-UHFFFAOYSA-N 3-[4-(8-fluoro-5h-[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidin-1-yl]propanoic acid;dihydrate Chemical compound O.O.C1CN(CCC(=O)O)CCC1=C1C2=NC=CC=C2COC2=CC(F)=CC=C21 CWNCDQYLHMXURI-UHFFFAOYSA-N 0.000 claims description 17
- 229960000383 azatadine Drugs 0.000 claims description 17
- SOYKEARSMXGVTM-HNNXBMFYSA-N dexchlorpheniramine Chemical compound C1([C@H](CCN(C)C)C=2N=CC=CC=2)=CC=C(Cl)C=C1 SOYKEARSMXGVTM-HNNXBMFYSA-N 0.000 claims description 17
- 229960001882 dexchlorpheniramine Drugs 0.000 claims description 17
- 229960003449 epinastine Drugs 0.000 claims description 17
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 claims description 17
- 229960004439 pemirolast Drugs 0.000 claims description 17
- 229940127557 pharmaceutical product Drugs 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 229960001971 ebastine Drugs 0.000 claims description 16
- 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 claims description 16
- 229950001539 sudexanox Drugs 0.000 claims description 16
- 229960003792 acrivastine Drugs 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
- 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 claims description 13
- 229950009746 arofylline Drugs 0.000 claims description 13
- 229950006944 atizoram Drugs 0.000 claims description 13
- 229960001158 nortriptyline Drugs 0.000 claims description 13
- 235000019260 propionic acid Nutrition 0.000 claims description 13
- 229950002405 cipamfylline Drugs 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 229950008068 tecastemizole Drugs 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 11
- 229950001653 cilomilast Drugs 0.000 claims description 11
- 229950008462 lirimilast Drugs 0.000 claims description 11
- 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 claims description 10
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 10
- 229950000393 darbufelone Drugs 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 10
- HCLXLZGAYCTHQJ-UHFFFAOYSA-N 1h-cyclohepta[b]pyridine Chemical compound C1=CC=CC=C2NC=CC=C21 HCLXLZGAYCTHQJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
- 208000023504 respiratory system disease Diseases 0.000 claims description 8
- 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 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 7
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- YWHBSFAATHJDAA-VQTJNVASSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-(1-pyrimidin-2-ylpiperidin-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=2N=CC=CN=2)CC1 YWHBSFAATHJDAA-VQTJNVASSA-N 0.000 claims description 6
- XHJIETATODEJOS-LOSJGSFVSA-N 4-[(4as,8ar)-4-(3,4-diethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2-yl]-n-phenylpiperidine-1-carboxamide Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)NC=2C=CC=CC=2)CC1 XHJIETATODEJOS-LOSJGSFVSA-N 0.000 claims description 6
- LWBCVAKHMSFVIE-FCHUYYIVSA-N 4-[(4as,8ar)-4-(3,4-diethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2-yl]-n-tert-butylpiperidine-1-carboxamide Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)NC(C)(C)C)CC1 LWBCVAKHMSFVIE-FCHUYYIVSA-N 0.000 claims description 6
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 claims description 6
- IRQAORMVIRUVSL-IZZNHLLZSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-(4-methylphenyl)sulfonylpiperidin-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(=O)(=O)C=2C=CC(C)=CC=2)CC1 IRQAORMVIRUVSL-IZZNHLLZSA-N 0.000 claims description 5
- 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 description 5
- AIZALTNNDIGFRS-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-2-(1-propan-2-ylpiperidin-4-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C1CC=CCC1C1=O)=NN1C1CCN(C(C)C)CC1 AIZALTNNDIGFRS-UHFFFAOYSA-N 0.000 claims description 5
- HPAKPHNDMHWESA-FCHUYYIVSA-N 5-[4-[(4as,8ar)-4-(3,4-diethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2-yl]piperidin-1-yl]-5-oxopentanoic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)CCCC(O)=O)CC1 HPAKPHNDMHWESA-FCHUYYIVSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229940075420 xanthine Drugs 0.000 claims description 5
- ZLSJEILNOWSWRS-VQTJNVASSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-(1-thieno[2,3-d]pyrimidin-4-ylpiperidin-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=3C=CSC=3N=CN=2)CC1 ZLSJEILNOWSWRS-VQTJNVASSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 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 description 3
- MUYFRCCWVDCNOJ-XZOQPEGZSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-(morpholine-4-carbonyl)piperidin-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(C(=O)N2CCOCC2)CC1 MUYFRCCWVDCNOJ-XZOQPEGZSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006187 phenyl benzyl group Chemical group 0.000 claims description 3
- 239000003380 propellant Substances 0.000 claims description 3
- 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 description 2
- CEDBOSAGZPVJAF-LOSJGSFVSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-[[4-(thiadiazol-4-yl)phenyl]methyl]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(CC=2C=CC(=CC=2)C=2N=NSC=2)CC1 CEDBOSAGZPVJAF-LOSJGSFVSA-N 0.000 claims description 2
- 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 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- ZKVAJTFDCLEYKT-AEFFLSMTSA-N (4ar,8as)-4-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)-2-(thian-4-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical group C1=2CC(C)(C)OC=2C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCSCC1 ZKVAJTFDCLEYKT-AEFFLSMTSA-N 0.000 claims 1
- DZUJGZGLPQEEDQ-LEWJYISDSA-N (4as,8ar)-2-[1-[2-(4-amino-3,5-dichlorophenyl)-2-oxoethyl]piperidin-4-yl]-4-(3,4-dimethoxyphenyl)-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(CC(=O)C=2C=C(Cl)C(N)=C(Cl)C=2)CC1 DZUJGZGLPQEEDQ-LEWJYISDSA-N 0.000 claims 1
- RLBQZJLGPGGCRU-BJKOFHAPSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-(pyridine-4-carbonyl)piperidin-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(C(=O)C=2C=CN=CC=2)CC1 RLBQZJLGPGGCRU-BJKOFHAPSA-N 0.000 claims 1
- WGTSMCZWJIQJKN-WUFINQPMSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-[2-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]acetyl]piperidin-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(C(=O)CN2CCN(CCN(C)C)CC2)CC1 WGTSMCZWJIQJKN-WUFINQPMSA-N 0.000 claims 1
- LWTZEJDQHWUMON-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(pyridin-4-ylmethyl)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(CC=2C=CN=CC=2)CC1 LWTZEJDQHWUMON-XZOQPEGZSA-N 0.000 claims 1
- MNNXYABGSPITFF-LEWJYISDSA-N 1-[4-[(4as,8ar)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2-yl]piperidine-1-carbonyl]-4-ethylpiperazine-2,3-dione Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N1CCC(N2C([C@@H]3CC=CC[C@@H]3C(=N2)C=2C=C(OC)C(OC)=CC=2)=O)CC1 MNNXYABGSPITFF-LEWJYISDSA-N 0.000 claims 1
- GSDIOOSPCUFPSE-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2h-phthalazin-1-one Chemical compound C1C=CC=C2C(=O)NNCC21 GSDIOOSPCUFPSE-UHFFFAOYSA-N 0.000 claims 1
- LPPPSUULWDSNAQ-UHFFFAOYSA-N 4-(1,2,3,4,4a,5-hexahydrobenzo[c][1,6]naphthyridin-6-yl)-N,N-di(propan-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1C(N1)=C(C=CC=C2)C2=C2C1CCNC2 LPPPSUULWDSNAQ-UHFFFAOYSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- OEFNVAZNTGKKSO-CTNGQTDRSA-N C1=2CC(C)(C)OC=2C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(=O)NC(C)(C)C)CC1 Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(=O)NC(C)(C)C)CC1 OEFNVAZNTGKKSO-CTNGQTDRSA-N 0.000 claims 1
- 229940112141 dry powder inhaler Drugs 0.000 claims 1
- 229940071648 metered dose inhaler Drugs 0.000 claims 1
- AINNLJVIAONTCV-UHFFFAOYSA-N n-ethyl-8-propan-2-yl-7h-purin-6-amine Chemical compound N1=CNC2=NC(C(C)C)=NC2=C1NCC AINNLJVIAONTCV-UHFFFAOYSA-N 0.000 claims 1
- RUOGJYKOQBFJIG-UHFFFAOYSA-N SCH-351591 Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)NC1=C(Cl)C=[N+]([O-])C=C1Cl RUOGJYKOQBFJIG-UHFFFAOYSA-N 0.000 description 10
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 10
- 229940095574 propionic acid Drugs 0.000 description 10
- 235000011054 acetic acid Nutrition 0.000 description 9
- 239000000443 aerosol Substances 0.000 description 8
- 208000006673 asthma Diseases 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 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 5
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 5
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 230000002757 inflammatory effect Effects 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- JBXODHBHAPVHDX-LEWJYISDSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(morpholine-4-carbonyl)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(=O)N2CCOCC2)CC1 JBXODHBHAPVHDX-LEWJYISDSA-N 0.000 description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 3
- YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 description 3
- WQZBPYDORYTARJ-CVEARBPZSA-N C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCSCC1 Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCSCC1 WQZBPYDORYTARJ-CVEARBPZSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 206010006451 bronchitis Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 description 2
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 2
- 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 2
- 206010066091 Bronchial Hyperreactivity Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108060003951 Immunoglobulin Proteins 0.000 description 2
- 102000015696 Interleukins Human genes 0.000 description 2
- 108010063738 Interleukins Proteins 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
- 108010003541 Platelet Activating Factor Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000013566 allergen Substances 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229960003291 chlorphenamine Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 210000003630 histaminocyte Anatomy 0.000 description 2
- 102000018358 immunoglobulin Human genes 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000012153 long-term therapy Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 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
- 102000003390 tumor necrosis factor Human genes 0.000 description 2
- VUNOKMWSRYYBGQ-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(pyridin-2-ylmethyl)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(CC=2N=CC=CC=2)CC1 VUNOKMWSRYYBGQ-XZOQPEGZSA-N 0.000 description 1
- HTHOGIQHWPPOOJ-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(pyridin-3-ylmethyl)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(CC=2C=NC=CC=2)CC1 HTHOGIQHWPPOOJ-XZOQPEGZSA-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
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-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
- VVJQGUSMDLABEG-UHFFFAOYSA-N 11h-benzo[1,2]cyclohepta[3,4-b]pyridine Chemical compound C1=CC2=CC=CN=C2CC2=CC=CC=C21 VVJQGUSMDLABEG-UHFFFAOYSA-N 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-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
- 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
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 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
- KKWWESVWJKAKNI-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-thiazole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(C(N)=O)=N1 KKWWESVWJKAKNI-UHFFFAOYSA-N 0.000 description 1
- DIUFONOIVHRUKS-UHFFFAOYSA-N 4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-11-ylidene)piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 DIUFONOIVHRUKS-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
- 208000000884 Airway Obstruction 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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 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
- 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
- 102000009109 Fc receptors Human genes 0.000 description 1
- 108010087819 Fc receptors Proteins 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 108090000526 Papain Proteins 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 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
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 206010039094 Rhinitis perennial Diseases 0.000 description 1
- 208000036284 Rhinitis seasonal Diseases 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
- 241000282887 Suidae Species 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
- 230000009471 action Effects 0.000 description 1
- 208000037883 airway inflammation Diseases 0.000 description 1
- 230000008369 airway response Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 201000010105 allergic rhinitis 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
- 239000004411 aluminium Substances 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
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036427 bronchial hyperreactivity Effects 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
- 239000000969 carrier Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 210000003979 eosinophil Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 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
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 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
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 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
- 229940055729 papain Drugs 0.000 description 1
- 235000019834 papain Nutrition 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002821 scintillation proximity assay Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- 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
- A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02004987 | 2002-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200407104B true ZA200407104B (en) | 2006-12-27 |
Family
ID=27771841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200407104A ZA200407104B (en) | 2002-03-06 | 2004-09-06 | Pharmaceutical composition of a PDE4 of a PDE3/4 inhibitor and a histamine receptor antagonist |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US20050112069A1 (enExample) |
| EP (2) | EP1849468B1 (enExample) |
| JP (1) | JP5150034B2 (enExample) |
| KR (1) | KR20040095255A (enExample) |
| CN (1) | CN101257904A (enExample) |
| AR (1) | AR038858A1 (enExample) |
| AT (1) | ATE369134T1 (enExample) |
| AU (1) | AU2003212268B2 (enExample) |
| BR (1) | BR0308220A (enExample) |
| CA (1) | CA2478612C (enExample) |
| CO (1) | CO5611148A2 (enExample) |
| CY (2) | CY1106927T1 (enExample) |
| DE (1) | DE60315426T2 (enExample) |
| DK (2) | DK1482938T3 (enExample) |
| EA (2) | EA010886B1 (enExample) |
| ES (2) | ES2291618T3 (enExample) |
| HR (1) | HRP20040909B1 (enExample) |
| IL (1) | IL163336A (enExample) |
| IS (2) | IS2536B (enExample) |
| MX (1) | MXPA04008460A (enExample) |
| NO (1) | NO335254B1 (enExample) |
| NZ (1) | NZ535611A (enExample) |
| PL (1) | PL211574B1 (enExample) |
| PT (2) | PT1849468E (enExample) |
| RS (1) | RS51018B (enExample) |
| SG (1) | SG160197A1 (enExample) |
| SI (2) | SI1482938T1 (enExample) |
| TW (1) | TWI347845B (enExample) |
| UA (1) | UA80117C2 (enExample) |
| WO (1) | WO2003074055A1 (enExample) |
| ZA (1) | ZA200407104B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067433B2 (en) * | 2005-11-09 | 2011-11-29 | Zalicus Inc. | Methods, compositions, and kits for the treatment of ophthalmic disorders |
| EP2091538B1 (en) * | 2006-12-20 | 2010-03-03 | Glaxo Group Limited | 4-benzyl-1(2h)-phthalazinones as h1 receptor antagonists |
| US20090182035A1 (en) * | 2007-04-11 | 2009-07-16 | Alcon Research, Ltd. | Use of a combination of olopatadine and cilomilast to treat non-infectious rhinitis and allergic conjunctivitis |
| US20080254029A1 (en) * | 2007-04-11 | 2008-10-16 | Alcon Research, Ltd. | Use of an Inhibitor of TNFa Plus an Antihistamine to Treat Allergic Rhinitis and Allergic Conjunctivitis |
| WO2009067597A1 (en) * | 2007-11-21 | 2009-05-28 | Decode Genetics Ehf | 4- (or 5-) substituted catechol derivatives |
| KR20090061972A (ko) * | 2007-12-12 | 2009-06-17 | 한미약품 주식회사 | 베포타스틴 ｐ-톨루엔술폰산염의 결정형, 이의 제조방법 및이를 포함하는 약학 조성물 |
| KR101852222B1 (ko) | 2011-02-07 | 2018-04-25 | 에스씨아이팜 에스에이알엘 | 낭포성 섬유증의 치료를 위한 신규 조성물 |
| KR102226833B1 (ko) * | 2013-06-28 | 2021-03-12 | 한미약품 주식회사 | 레보세티리진 및 몬테루카스트를 포함하는 안정성이 개선된 복합 과립 제형 |
| JP2017525721A (ja) * | 2014-08-26 | 2017-09-07 | ファンダシオン パラ ラ インベスティガシオン メディカ アプリカダＦｕｎｄａｃｉｏｎ Ｐａｒａ Ｌａ Ｉｎｖｅｓｔｉｇａｓｉｏｎ Ｍｅｄｉｃａ Ａｐｌｉｃａｄａ | 認知欠損または認知障害に伴って進行する神経障害のおよび神経変性疾患の処置および予防のための製品 |
| BR112017007194B1 (pt) | 2014-10-09 | 2023-11-07 | Guangdong Raynovent Biotech Co., Ltd | Compostos de hidroxil purina e uso dos mesmos |
| CN109956947A (zh) * | 2017-12-25 | 2019-07-02 | 江苏恒瑞医药股份有限公司 | 一种cns抑制剂的新晶型、制备方法及用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| AU650953B2 (en) | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| HU220041B (hu) * | 1993-07-02 | 2001-10-28 | Byk Gulden Lomberg Chemische Fabrik Gmbh. | Fluor-alkoxi-helyettesített benzamidszármazékok, eljárás előállításukra és ezeket a vegyületeket tartalmazó gyógyászati készítmények |
| US5900421A (en) * | 1997-02-11 | 1999-05-04 | Sepracor Inc. | Methods and compositions for treating allergic asthma and dermatitis using descarboethoxyloratadine |
| US5990147A (en) * | 1997-11-07 | 1999-11-23 | Schering Corporation | H3 receptor ligands of the phenyl-alkyl-imidazoles type |
| BR9804993A (pt) * | 1998-11-10 | 2000-06-06 | Panacea Biotec Ltd | Composição antialérgica e antiinflamatória |
| US6174878B1 (en) * | 1999-08-31 | 2001-01-16 | Alcon Laboratories, Inc. | Topical use of kappa opioid agonists to treat otic pain |
| EP1244654A1 (en) * | 1999-10-25 | 2002-10-02 | ALTANA Pharma AG | Tetrahydrothiopy ranphthalazinone derivatives as pde4 inhibitors |
| US7585847B2 (en) * | 2000-02-03 | 2009-09-08 | Coley Pharmaceutical Group, Inc. | Immunostimulatory nucleic acids for the treatment of asthma and allergy |
| GB0115181D0 (en) * | 2001-06-20 | 2001-08-15 | Glaxo Group Ltd | Novel use |
-
2003
- 2003-02-20 TW TW092103525A patent/TWI347845B/zh not_active IP Right Cessation
- 2003-02-25 CA CA2478612A patent/CA2478612C/en not_active Expired - Fee Related
- 2003-02-25 HR HR20040909 patent/HRP20040909B1/xx not_active IP Right Cessation
- 2003-02-25 EA EA200601592A patent/EA010886B1/ru not_active IP Right Cessation
- 2003-02-25 ES ES03708130T patent/ES2291618T3/es not_active Expired - Lifetime
- 2003-02-25 DE DE60315426T patent/DE60315426T2/de not_active Expired - Lifetime
- 2003-02-25 SG SG200606154-3A patent/SG160197A1/en unknown
- 2003-02-25 MX MXPA04008460A patent/MXPA04008460A/es active IP Right Grant
- 2003-02-25 EA EA200401137A patent/EA007903B1/ru not_active IP Right Cessation
- 2003-02-25 JP JP2003572572A patent/JP5150034B2/ja not_active Expired - Fee Related
- 2003-02-25 PL PL371056A patent/PL211574B1/pl unknown
- 2003-02-25 EP EP07112823A patent/EP1849468B1/en not_active Expired - Lifetime
- 2003-02-25 US US10/506,875 patent/US20050112069A1/en not_active Abandoned
- 2003-02-25 SI SI200330970T patent/SI1482938T1/sl unknown
- 2003-02-25 DK DK03708130T patent/DK1482938T3/da active
- 2003-02-25 ES ES07112823T patent/ES2400670T3/es not_active Expired - Lifetime
- 2003-02-25 DK DK07112823.5T patent/DK1849468T3/da active
- 2003-02-25 NZ NZ535611A patent/NZ535611A/xx not_active IP Right Cessation
- 2003-02-25 CN CNA038053349A patent/CN101257904A/zh active Pending
- 2003-02-25 KR KR10-2004-7013742A patent/KR20040095255A/ko not_active Ceased
- 2003-02-25 WO PCT/EP2003/001876 patent/WO2003074055A1/en not_active Ceased
- 2003-02-25 AU AU2003212268A patent/AU2003212268B2/en not_active Ceased
- 2003-02-25 EP EP03708130A patent/EP1482938B1/en not_active Expired - Lifetime
- 2003-02-25 BR BR0308220-2A patent/BR0308220A/pt not_active Application Discontinuation
- 2003-02-25 UA UA20041008055A patent/UA80117C2/uk unknown
- 2003-02-25 AT AT03708130T patent/ATE369134T1/de active
- 2003-02-25 PT PT71128235T patent/PT1849468E/pt unknown
- 2003-02-25 PT PT03708130T patent/PT1482938E/pt unknown
- 2003-02-25 RS YUP-780/04A patent/RS51018B/sr unknown
- 2003-02-25 SI SI200332245T patent/SI1849468T1/sl unknown
- 2003-02-27 AR ARP030100646A patent/AR038858A1/es unknown
-
2004
- 2004-08-03 IL IL163336A patent/IL163336A/en not_active IP Right Cessation
- 2004-09-03 IS IS7438A patent/IS2536B/is unknown
- 2004-09-03 CO CO04086713A patent/CO5611148A2/es active IP Right Grant
- 2004-09-06 ZA ZA200407104A patent/ZA200407104B/en unknown
- 2004-10-06 NO NO20044230A patent/NO335254B1/no not_active IP Right Cessation
-
2007
- 2007-10-11 CY CY20071101307T patent/CY1106927T1/el unknown
-
2008
- 2008-09-04 IS IS8760A patent/IS8760A/is unknown
-
2013
- 2013-02-21 CY CY20131100163T patent/CY1113894T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8486923B2 (en) | Use of the combination of ciclesonide and antihistamines for the treatment of allergic rhinitis | |
| ZA200407104B (en) | Pharmaceutical composition of a PDE4 of a PDE3/4 inhibitor and a histamine receptor antagonist | |
| JP2004518727A (ja) | 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 | |
| KR20250133980A (ko) | Ccr3-억제제의 용도 | |
| CZ2002497A3 (cs) | Farmaceutický prostředek pro potlačení menopauzálních návalů horka | |
| TW200423932A (en) | Combination of a PDE IV inhibitor and a TNF-alpha antagonist | |
| KR20170141774A (ko) | 항바이러스 및 항염증 치료제의 치료 조합물 | |
| TW202523323A (zh) | 用於治療慢性心臟衰竭的吡唑並〔３，４－ｄ〕嘧啶酮化合物 | |
| AU2003229771A1 (en) | Combination of a proton pump inhibitor and a respiratory agent for the treatment of respiratory diseases | |
| HK1080744A (en) | The use of the combination of ciclesonide and antihistamines for the treatment of allergic ehinitis | |
| HK40015701A (en) | Use of ccr3-inhibitors | |
| HK1071308B (en) | Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist | |
| KR20050034760A (ko) | 선택적 포스포디에스테라제-4 억제제에 의한 비알레르기성비염의 치료방법 |