JP2007517067A5 - - Google Patents
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- JP2007517067A5 JP2007517067A5 JP2006547613A JP2006547613A JP2007517067A5 JP 2007517067 A5 JP2007517067 A5 JP 2007517067A5 JP 2006547613 A JP2006547613 A JP 2006547613A JP 2006547613 A JP2006547613 A JP 2006547613A JP 2007517067 A5 JP2007517067 A5 JP 2007517067A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- formulation
- corticosteroid
- hydroxy
- sae
- 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.)
- Withdrawn
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- 239000000203 mixture Substances 0.000 claims description 33
- 239000003246 corticosteroid Substances 0.000 claims description 27
- 238000009472 formulation Methods 0.000 claims description 25
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 5
- 239000000812 cholinergic antagonist Substances 0.000 claims description 5
- 239000003607 modifier Substances 0.000 claims description 5
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 claims description 4
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 4
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims description 4
- 229960003638 dopamine Drugs 0.000 claims description 4
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 claims description 4
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims description 4
- 229940044601 receptor agonist Drugs 0.000 claims description 4
- 239000000018 receptor agonist Substances 0.000 claims description 4
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 claims description 4
- DHSSDEDRBUKTQY-UHFFFAOYSA-N 6-prop-2-enyl-4,5,7,8-tetrahydrothiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC=C)CCC2=C1N=C(N)S2 DHSSDEDRBUKTQY-UHFFFAOYSA-N 0.000 claims description 3
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
- BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 claims description 3
- 230000003113 alkalizing effect Effects 0.000 claims description 3
- 229940092705 beclomethasone Drugs 0.000 claims description 3
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 3
- 229960004436 budesonide Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229960004502 levodopa Drugs 0.000 claims description 3
- NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 claims description 2
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002535 acidifier Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 229960004046 apomorphine Drugs 0.000 claims description 2
- 229960002802 bromocriptine Drugs 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 229960004596 cabergoline Drugs 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims description 2
- 229960001334 corticosteroids Drugs 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 235000003599 food sweetener Nutrition 0.000 claims description 2
- 229960001361 ipratropium bromide Drugs 0.000 claims description 2
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 claims description 2
- 229960003587 lisuride Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229960004851 pergolide Drugs 0.000 claims description 2
- 229960003089 pramipexole Drugs 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- FTSUPYGMFAPCFZ-ZWNOBZJWSA-N quinpirole Chemical compound C([C@H]1CCCN([C@@H]1C1)CCC)C2=C1C=NN2 FTSUPYGMFAPCFZ-ZWNOBZJWSA-N 0.000 claims description 2
- 229950001037 quinpirole Drugs 0.000 claims description 2
- 229960001879 ropinirole Drugs 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000003765 sweetening agent Substances 0.000 claims description 2
- 229960000257 tiotropium bromide Drugs 0.000 claims description 2
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 2
- -1 dimethylcarbamate 5- ( 2-((1,1-dimethylethyl) amino) -1-hydroxyethyl) -1,3-phenylene ester Chemical class 0.000 claims 10
- 239000000243 solution Substances 0.000 claims 8
- 239000006199 nebulizer Substances 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 239000012669 liquid formulation Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229960002052 salbutamol Drugs 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims 3
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 2
- 102000000743 Interleukin-5 Human genes 0.000 claims 2
- 108010002616 Interleukin-5 Proteins 0.000 claims 2
- 239000000048 adrenergic agonist Substances 0.000 claims 2
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims 2
- 229950000210 beclometasone dipropionate Drugs 0.000 claims 2
- 229960004217 benzyl alcohol Drugs 0.000 claims 2
- JBRBWHCVRGURBA-UHFFFAOYSA-N broxaterol Chemical compound CC(C)(C)NCC(O)C1=CC(Br)=NO1 JBRBWHCVRGURBA-UHFFFAOYSA-N 0.000 claims 2
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229960000676 flunisolide Drugs 0.000 claims 2
- 229940043075 fluocinolone Drugs 0.000 claims 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 claims 2
- 229960000289 fluticasone propionate Drugs 0.000 claims 2
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate 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](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[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 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000003589 local anesthetic agent Substances 0.000 claims 2
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 claims 2
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 claims 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 claims 2
- WVLAAKXASPCBGT-UHFFFAOYSA-N reproterol Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 WVLAAKXASPCBGT-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 229960002117 triamcinolone acetonide Drugs 0.000 claims 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims 2
- NUBLQEKABJXICM-FQEVSTJZSA-N (1r)-1-(4-amino-3,5-dichlorophenyl)-2-[6-(2-pyridin-2-ylethoxy)hexylamino]ethanol Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1[C@@H](O)CNCCCCCCOCCC1=CC=CC=N1 NUBLQEKABJXICM-FQEVSTJZSA-N 0.000 claims 1
- NBMKJKDGKREAPL-CXSFZGCWSA-N (8s,9r,10s,11s,13s,14s,16r,17r)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-CXSFZGCWSA-N 0.000 claims 1
- GIIZNNXWQWCKIB-VWLOTQADSA-N (R)-salmeterol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-VWLOTQADSA-N 0.000 claims 1
- RKUNBYITZUJHSG-FXUDXRNXSA-N (S)-atropine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 RKUNBYITZUJHSG-FXUDXRNXSA-N 0.000 claims 1
- NUBLQEKABJXICM-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[6-(2-pyridin-2-ylethoxy)hexylamino]ethanol Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(O)CNCCCCCCOCCC1=CC=CC=N1 NUBLQEKABJXICM-UHFFFAOYSA-N 0.000 claims 1
- RGVPOXRFEPSFGH-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 RGVPOXRFEPSFGH-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- ZUGRYLJRHKHZLR-UHFFFAOYSA-N 1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=CC2=C1 ZUGRYLJRHKHZLR-UHFFFAOYSA-N 0.000 claims 1
- ADUOECRTBIGRQZ-UHFFFAOYSA-N 2-(tert-butylamino)-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(C)(C)C)=C1 ADUOECRTBIGRQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 229940124125 5 Lipoxygenase inhibitor Drugs 0.000 claims 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 claims 1
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone 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@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 claims 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 claims 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims 1
- 241001106067 Atropa Species 0.000 claims 1
- QGBIFMJAQARMNQ-QISPFCDLSA-N C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(SC)[C@@]2(C)C[C@@H]1O Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(SC)[C@@]2(C)C[C@@H]1O QGBIFMJAQARMNQ-QISPFCDLSA-N 0.000 claims 1
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- BQTXJHAJMDGOFI-NJLPOHDGSA-N Dexamethasone 21-(4-Pyridinecarboxylate) Chemical compound O=C([C@]1(O)[C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)COC(=O)C1=CC=NC=C1 BQTXJHAJMDGOFI-NJLPOHDGSA-N 0.000 claims 1
- VTUSIVBDOCDNHS-UHFFFAOYSA-N Etidocaine Chemical compound CCCN(CC)C(CC)C(=O)NC1=C(C)C=CC=C1C VTUSIVBDOCDNHS-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 claims 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
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| JP2016133094A Expired - Lifetime JP6186478B2 (ja) | 2003-12-31 | 2016-07-05 | スルホアルキルエーテルシクロデキストリンおよびコルチコステロイドを含む吸入製剤 |
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| JP (6) | JP2007517068A (https=) |
| KR (3) | KR20070007075A (https=) |
| CN (3) | CN1921830A (https=) |
| AU (3) | AU2004311478A1 (https=) |
| BR (3) | BRPI0418386A (https=) |
| CA (3) | CA2552641A1 (https=) |
| DK (1) | DK1732512T3 (https=) |
| HU (1) | HUE032527T2 (https=) |
| IL (6) | IL176577A0 (https=) |
| MX (2) | MX348041B (https=) |
| NZ (1) | NZ548225A (https=) |
| PT (1) | PT1732512T (https=) |
| RU (3) | RU2390330C2 (https=) |
| WO (3) | WO2005065435A2 (https=) |
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- 2004-12-31 EP EP05704920A patent/EP1729724A4/en not_active Withdrawn
- 2004-12-31 KR KR1020067015494A patent/KR20070007075A/ko not_active Ceased
- 2004-12-31 KR KR1020067015501A patent/KR20070005586A/ko not_active Withdrawn
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- 2004-12-31 RU RU2006127467/15A patent/RU2390330C2/ru active
- 2004-12-31 DK DK05704917.3T patent/DK1732512T3/en active
- 2004-12-31 CN CNA2004800422281A patent/CN1921830A/zh active Pending
- 2004-12-31 KR KR1020067015502A patent/KR20070007076A/ko not_active Ceased
- 2004-12-31 WO PCT/US2005/000082 patent/WO2005065435A2/en not_active Ceased
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- 2004-12-31 BR BRPI0418386-0A patent/BRPI0418386A/pt not_active IP Right Cessation
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- 2004-12-31 HU HUE05704917A patent/HUE032527T2/en unknown
- 2004-12-31 CA CA002551826A patent/CA2551826A1/en not_active Abandoned
- 2004-12-31 AU AU2004312095A patent/AU2004312095A1/en not_active Abandoned
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2005
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- 2005-01-03 EP EP05704919A patent/EP1718276A4/en not_active Withdrawn
- 2005-01-03 WO PCT/US2005/000084 patent/WO2005065651A1/en not_active Ceased
-
2006
- 2006-06-27 IL IL176577A patent/IL176577A0/en unknown
- 2006-06-27 IL IL176575A patent/IL176575A0/en unknown
- 2006-06-27 IL IL176576A patent/IL176576A0/en unknown
-
2012
- 2012-08-24 JP JP2012184694A patent/JP5782413B2/ja not_active Expired - Lifetime
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2013
- 2013-04-25 IL IL225946A patent/IL225946A/en active IP Right Grant
- 2013-04-25 IL IL251496A patent/IL251496B/en active IP Right Grant
-
2015
- 2015-03-04 JP JP2015041915A patent/JP2015129173A/ja active Pending
-
2016
- 2016-07-05 JP JP2016133094A patent/JP6186478B2/ja not_active Expired - Lifetime
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2017
- 2017-04-02 IL IL251496A patent/IL251496A0/en unknown
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