DD297647A5 - Neue thienylcarbonsaeureester von aminoalkoholen, ihre quaternierungsprodukte sowie die herstellung und verwendung dieser verbindungen - Google Patents

Neue thienylcarbonsaeureester von aminoalkoholen, ihre quaternierungsprodukte sowie die herstellung und verwendung dieser verbindungen Download PDF

Info

Publication number: DD297647A5
Authority: DD; German Democratic Republic
Prior art keywords: thienyl; compounds; tropanyl; formula; methobromide
Prior art date: 1989-09-16

Application number

DD90343854A

Other languages

German (de)

English (en)

Inventor

Rolf Banholzer

Rudolf Bauer

Richard Reichl

Original Assignee

��@��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-09-16

Filing date

1990-09-06

Publication date

1992-01-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6389619&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD297647(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-09-06 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1992-01-16 Publication of DD297647A5 publication Critical patent/DD297647A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 48
-1 AMINO Chemical class 0.000 title claims description 13
239000002253 acid Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 7
230000001476 alcoholic effect Effects 0.000 title 1
239000004480 active ingredient Substances 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 4
239000003814 drug Substances 0.000 claims abstract 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
125000001544 thienyl group Chemical group 0.000 claims description 13
238000005809 transesterification reaction Methods 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000000543 intermediate Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
239000000155 melt Substances 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
206010040741 Sinus bradycardia Diseases 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
150000001414 amino alcohols Chemical class 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
208000023504 respiratory system disease Diseases 0.000 claims description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
230000001078 anti-cholinergic effect Effects 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229940079593 drug Drugs 0.000 abstract 1
239000004593 Epoxy Substances 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 8
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 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
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 5
FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
SYHWYWHVEQQDMO-UHFFFAOYSA-N methyl 2-hydroxy-2,2-dithiophen-2-ylacetate Chemical compound C=1C=CSC=1C(O)(C(=O)OC)C1=CC=CS1 SYHWYWHVEQQDMO-UHFFFAOYSA-N 0.000 description 4
FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
GIWRVUADKUVEGU-UHFFFAOYSA-N 2-oxo-2-thiophen-2-ylacetic acid Chemical compound OC(=O)C(=O)C1=CC=CS1 GIWRVUADKUVEGU-UHFFFAOYSA-N 0.000 description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FVEJUHUCFCAYRP-UHFFFAOYSA-N 2-hydroxy-2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(O)(C(=O)O)C1=CC=CS1 FVEJUHUCFCAYRP-UHFFFAOYSA-N 0.000 description 2
WPAQIMRFMFRJTP-UHFFFAOYSA-N 3-fluorothiophene Chemical compound FC=1C=CSC=1 WPAQIMRFMFRJTP-UHFFFAOYSA-N 0.000 description 2
XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 2
QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000000812 cholinergic antagonist Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
HTJPDOPKPWUNBX-UHFFFAOYSA-M magnesium;2h-thiophen-2-ide;bromide Chemical compound [Mg+2].[Br-].C=1C=[C-]SC=1 HTJPDOPKPWUNBX-UHFFFAOYSA-M 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 2
ICMJIOARABGYHC-UHFFFAOYSA-N 2-(furan-3-yl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C=1C=COC=1 ICMJIOARABGYHC-UHFFFAOYSA-N 0.000 description 1
CEGNDKAALPVWLG-UHFFFAOYSA-N 2-bromo-3-fluorothiophene Chemical group FC=1C=CSC=1Br CEGNDKAALPVWLG-UHFFFAOYSA-N 0.000 description 1
WMCDDNAETBQBMJ-UHFFFAOYSA-N 2-bromo-5-fluorothiophene Chemical compound FC1=CC=C(Br)S1 WMCDDNAETBQBMJ-UHFFFAOYSA-N 0.000 description 1
DXHCHIJMMKQRKR-UHFFFAOYSA-N 2-fluorothiophene Chemical compound FC1=CC=CS1 DXHCHIJMMKQRKR-UHFFFAOYSA-N 0.000 description 1
150000005749 2-halopyridines Chemical class 0.000 description 1
HLBOAQSKBNNHMW-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyridine Chemical compound COC1=CC=CC(C=2C=NC=CC=2)=C1 HLBOAQSKBNNHMW-UHFFFAOYSA-N 0.000 description 1
XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
150000005750 3-halopyridines Chemical class 0.000 description 1
150000005751 4-halopyridines Chemical class 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920008712 Copo Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
101150084935 PTER gene Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
XQJMXPAEFMWDOZ-PBWFPOADSA-N [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] benzoate Chemical compound C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-PBWFPOADSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
244000309464 bull Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
YGGQOQVOGNCEBH-UHFFFAOYSA-N ethyl 2-hydroxy-2-phenyl-2-thiophen-2-ylacetate Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC)C1=CC=CS1 YGGQOQVOGNCEBH-UHFFFAOYSA-N 0.000 description 1
BDYPNJQVKHKGPQ-UHFFFAOYSA-N ethyl 2-hydroxy-2-thiophen-2-ylacetate Chemical compound CCOC(=O)C(O)C1=CC=CS1 BDYPNJQVKHKGPQ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
CCKXJTLFNDEZDU-UHFFFAOYSA-N furan-3-carbonyl cyanide Chemical compound N#CC(=O)C=1C=COC=1 CCKXJTLFNDEZDU-UHFFFAOYSA-N 0.000 description 1
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229960001361 ipratropium bromide Drugs 0.000 description 1
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 description 1
239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000002502 liposome Substances 0.000 description 1
SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
TWMBHJJCUUXOKM-UHFFFAOYSA-N methyl 2-oxo-2-thiophen-2-ylacetate Chemical compound COC(=O)C(=O)C1=CC=CS1 TWMBHJJCUUXOKM-UHFFFAOYSA-N 0.000 description 1
WXJHRBGDHJRFBK-UHFFFAOYSA-N methyl 2-oxo-2-thiophen-3-ylacetate Chemical class COC(=O)C(=O)C=1C=CSC=1 WXJHRBGDHJRFBK-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
230000004899 motility Effects 0.000 description 1
239000002547 new drug Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
FIMXSEMBHGTNKT-UPGAHCIJSA-N scopine Chemical compound C([C@@H]1N2C)C(O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-UPGAHCIJSA-N 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Glass Compositions (AREA)
Compositions Of Oxide Ceramics (AREA)
Disintegrating Or Milling (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

DD90343854A 1989-09-16 1990-09-06 Neue thienylcarbonsaeureester von aminoalkoholen, ihre quaternierungsprodukte sowie die herstellung und verwendung dieser verbindungen DD297647A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3931041A DE3931041C2 (de)	1989-09-16	1989-09-16	Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
DD297647A5 true DD297647A5 (de)	1992-01-16

Family

ID=6389619

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343854A DD297647A5 (de)	1989-09-16	1990-09-06	Neue thienylcarbonsaeureester von aminoalkoholen, ihre quaternierungsprodukte sowie die herstellung und verwendung dieser verbindungen

Country Status (33)

Country	Link
US (1)	USRE39820E1 (fr)
EP (1)	EP0418716B1 (fr)
JP (1)	JPH0730074B2 (fr)
KR (1)	KR0168432B1 (fr)
AT (1)	ATE103914T1 (fr)
AU (1)	AU642913B2 (fr)
BG (1)	BG61295B2 (fr)
CA (1)	CA2066248C (fr)
CZ (1)	CZ284589B6 (fr)
DD (1)	DD297647A5 (fr)
DE (3)	DE3931041C2 (fr)
DK (1)	DK0418716T3 (fr)
ES (1)	ES2052125T3 (fr)
FI (1)	FI114395B (fr)
HR (1)	HRP940723B1 (fr)
HU (2)	HU208823B (fr)
IE (1)	IE65528B1 (fr)
IL (1)	IL95691A (fr)
LU (1)	LU90949I2 (fr)
MX (1)	MX9203150A (fr)
NL (1)	NL300084I2 (fr)
NO (2)	NO301478B1 (fr)
NZ (1)	NZ235306A (fr)
PH (1)	PH31617A (fr)
PL (1)	PL168468B1 (fr)
PT (1)	PT95312B (fr)
RU (1)	RU2073677C1 (fr)
SI (1)	SI9011744B (fr)
SK (1)	SK279453B6 (fr)
UA (1)	UA41272C2 (fr)
WO (1)	WO1991004252A1 (fr)
YU (1)	YU47800B (fr)
ZA (1)	ZA907338B (fr)

Families Citing this family (152)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3931041C2 (de)	1989-09-16	2000-04-06	Boehringer Ingelheim Kg	Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE4108393A1 (de) *	1991-03-15	1992-09-17	Boehringer Ingelheim Kg	Neue ester bi- und tricyclischer aminoalkohole, ihre herstellung und ihre verwendung in arzneimitteln
US5770738A (en) *	1992-03-05	1998-06-23	Boehringer Ingelheim Kg	Esters of bi- and tricyclic amino alcohols, their preparation and their use in pharmaceutical compositions
DE19921693A1 (de)	1999-05-12	2000-11-16	Boehringer Ingelheim Pharma	Neuartige Arzneimittelkompositionen auf der Basis von anticholinergisch wirksamen Verbindungen und ß-Mimetika
ES2165768B1 (es)	1999-07-14	2003-04-01	Almirall Prodesfarma Sa	Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen.
US7214687B2 (en)	1999-07-14	2007-05-08	Almirall Ag	Quinuclidine derivatives and medicinal compositions containing the same
GB0009592D0 (en) *	2000-04-18	2000-06-07	Glaxo Group Ltd	Respiratory combinations
GB0009583D0 (en) *	2000-04-18	2000-06-07	Glaxo Group Ltd	Respiratory formulations
GB0009605D0 (en) *	2000-04-18	2000-06-07	Glaxo Group Ltd	Medicaments
GB0009606D0 (en) *	2000-04-18	2000-06-07	Glaxo Group Ltd	Therapeutic combinations
US6750210B2 (en)	2000-08-05	2004-06-15	Smithkline Beecham Corporation	Formulation containing novel anti-inflammatory androstane derivative
CA2417826A1 (fr)	2000-08-05	2002-02-14	Glaxo Group Limited	Derives de 17-beta-carbothioate-17-alpha-arylcarbonyloxyloxy androstane utilises comme anti-inflammatoires
US6777400B2 (en)	2000-08-05	2004-08-17	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
US6777399B2 (en)	2000-08-05	2004-08-17	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
US6858593B2 (en)	2000-08-05	2005-02-22	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative compositions
US6858596B2 (en)	2000-08-05	2005-02-22	Smithkline Beecham Corporation	Formulation containing anti-inflammatory androstane derivative
US6787532B2 (en)	2000-08-05	2004-09-07	Smithkline Beecham Corporation	Formulation containing anti-inflammatory androstane derivatives
GB0019172D0 (en)	2000-08-05	2000-09-27	Glaxo Group Ltd	Novel compounds
US6759398B2 (en)	2000-08-05	2004-07-06	Smithkline Beecham Corporation	Anti-inflammatory androstane derivative
US6908928B2 (en)	2000-10-12	2005-06-21	Bi Pharma Kg.	Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions
AU2002214996B2 (en) *	2000-10-12	2007-03-15	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Crystalline monohydrate, method for producing the same and the use thereof in the production of a medicament
AP1712A (en)	2000-10-12	2007-01-24	Boehringer Ingelheim Pharma	Novel tiotropium-containing inhalation powder
EA007604B1 (ru) *	2000-10-31	2006-12-29	Бёрингер Ингельхайм Фарма Гмбх Унд Ко. Кг	Ингаляционная композиция в виде раствора с солью тиотропия
DE10064816A1 (de) *	2000-12-22	2002-06-27	Boehringer Ingelheim Pharma	Verfahren zur Herstellung eines Anticholinergikums
SI1353919T1 (sl)	2000-12-28	2006-12-31	Almirall Prodesfarma Ag	Novi derivati kinuklidina in medicinske zmesi, kijih vsebujejo.
US6506900B1 (en)	2001-01-31	2003-01-14	Boehringer Ingelheim Pharma Ag	Process for preparing a scopine ester intermediate
UA77656C2 (en)	2001-04-07	2007-01-15	Glaxo Group Ltd	S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent
AR033290A1 (es)	2001-04-30	2003-12-10	Glaxo Group Ltd	Derivados antiinflamatorios de androstano
DE10126924A1 (de) *	2001-06-01	2002-12-05	Boehringer Ingelheim Pharma	Inhalationskapseln
US6608055B2 (en)	2001-06-22	2003-08-19	Boehringer Ingelheim Pharma Kg	Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition
CA2450961C (fr) *	2001-06-22	2010-03-30	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substance anticholinergique cristalline, procedes de production et son utilisation pour la production de composition pharmaceutique
US6610849B2 (en) *	2001-06-28	2003-08-26	Boehringer Ingelheim Pharma Kg	Process for the manufacture of tropenol
DE10141377A1 (de)	2001-08-23	2003-03-13	Boehringer Ingelheim Pharma	Aufstreuverfahren zur Herstellung von Pulverformulierungen
US6890920B2 (en)	2001-10-26	2005-05-10	Pharmacia & Upjohn Company	Quaternary ammonium compounds
DE10200943A1 (de) *	2002-01-12	2003-07-24	Boehringer Ingelheim Pharma	Verfahren zur Herstellung von Scopinestern
DE10203749A1 (de) *	2002-01-31	2003-08-14	Boehringer Ingelheim Pharma	Neue Anticholinergika, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel
US6696462B2 (en)	2002-01-31	2004-02-24	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Anticholinergics, processes for the preparation thereof, and pharmaceutical compositions
GB0202635D0 (en) *	2002-02-05	2002-03-20	Glaxo Wellcome Mfg Pte Ltd	Formulation containing novel anti-inflammatory androstane derivative
AU2003201745A1 (en) *	2002-02-11	2003-09-04	Pfizer Limited	Nicotinamide derivatives and a tiotropium salt in combination for the treatment of e.g. inflammatory, allergic and respiratory diseases
GB0203193D0 (en) *	2002-02-11	2002-03-27	Pfizer Ltd	Nicotinamide derivatives useful as pde4 inhibitors
DE10212264A1 (de) *	2002-03-20	2003-10-02	Boehringer Ingelheim Pharma	Kristallines Mikronisat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung eines Arzneimittels
US7309707B2 (en) *	2002-03-20	2007-12-18	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Crystalline micronisate, process for the manufacture thereof and use thereof for the preparation of a medicament
DE10214264A1 (de) *	2002-03-28	2003-10-16	Boehringer Ingelheim Pharma	HFA-Suspensionsformulierungen eines Anhydrats
US7244415B2 (en)	2002-03-28	2007-07-17	Boehringer Ingelheim Pharma Gmbh & Co. Kg	HFA suspension formulations of an anhydrate
UA80123C2 (en)	2002-04-09	2007-08-27	Boehringer Ingelheim Pharma	Inhalation kit comprising inhalable powder of tiotropium
DE10216036A1 (de)	2002-04-11	2003-10-23	Boehringer Ingelheim Pharma	Aerosolformulierung für die Inhalation enthaltend ein Tiotropiumsalz
DE10224091A1 (de) *	2002-05-31	2003-12-11	Boehringer Ingelheim Pharma	Technisches Verfahren zur Herstellung von Tropenol
GB2389530B (en)	2002-06-14	2007-01-10	Cipla Ltd	Pharmaceutical compositions
US7763280B2 (en)	2002-11-28	2010-07-27	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Tiotropium containing powder formulation for inhalation
CA2513188A1 (fr) *	2003-01-16	2004-08-05	University Of Rochester	Composes antimuscariniques quaternaires destines au traitement de maladies vesicales
US20040226556A1 (en)	2003-05-13	2004-11-18	Deem Mark E.	Apparatus for treating asthma using neurotoxin
ES2329133T3 (es)	2003-05-28	2009-11-23	Theravance, Inc.	Compuestos azabicicloalcanicos como antagonistas de receptores de muscarinicos.
DK1682543T3 (da) *	2003-11-03	2010-12-13	Boehringer Ingelheim Int	Fremgangsmåde til fremstilling af nye tiotropiumsalte
DK1682541T3 (da)	2003-11-03	2010-06-28	Boehringer Ingelheim Int	Fremgangsmåde til fremstilling af tiotropiumsalte
WO2005042527A1 (fr) *	2003-11-03	2005-05-12	Boehringer Ingelheim International Gmbh	Nouvel anhydrate cristallin a effet anticholinergique
US7968717B2 (en)	2003-11-03	2011-06-28	Boehringer Ingelhein International Gmbh	Crystalline anhydrate with anticholinergic efficacy
SE0303570L (sv)	2003-12-03	2005-06-04	Microdrug Ag	Fukt-känslig medicinsk produkt
DE102004041253A1 (de) *	2004-08-26	2006-03-02	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neues Verfahren zur Herstellung von Tiotropiumsalzen
EP1785421A1 (fr) *	2004-08-30	2007-05-16	Ono Pharmaceutical Co., Ltd.	Dérivé du tropane
KR20080012932A (ko)	2005-05-02	2008-02-12	베링거 인겔하임 인터내셔날 게엠베하	티오트로퓸 브로마이드의 신규한 결정형
EP1879888A2 (fr) *	2005-05-02	2008-01-23	Boehringer Ingelheim International GmbH	Formes cristallines de bromure de tiotropium
DE102005035112A1 (de)	2005-07-27	2007-02-15	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neues Verfahren zur Herstellung von Tiotropiumsalzen unter Anwendung von in organischen Lösungsmitteln löslichen N-Methylscopiniumsalzen
KR20080039974A (ko) *	2005-08-06	2008-05-07	베링거 인겔하임 인터내셔날 게엠베하	중증 지속성 천식의 치료에서 티오트로퓸 염의 용도
RU2442771C2 (ru)	2005-08-08	2012-02-20	Арджента Дискавери Лтд	Производные бицикло[2,2,1]гепт-7-иламина и их применения
TWI389692B (zh)	2005-10-10	2013-03-21	Boehringer Ingelheim Int	用以吸入β-共效劑的氣溶膠調配物
US20070086957A1 (en) *	2005-10-10	2007-04-19	Thierry Bouyssou	Combination of medicaments for the treatment of respiratory diseases
DE102005059602A1 (de)	2005-12-14	2007-06-21	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verfahren zur Mikronisierung
US20070167480A1 (en) *	2005-12-19	2007-07-19	Sicor Inc.	Pure and stable tiotropium bromide
PT1869035E (pt) *	2005-12-19	2013-01-10	Sicor Inc	Novas formas de brometo de tiotrópio e processos para sua preparação
US9108962B2 (en)	2005-12-19	2015-08-18	Sicor, Inc.	Forms of tiotropium bromide and processes for preparation thereof
KR20080083060A (ko) *	2006-01-04	2008-09-12	베링거 인겔하임 인터내셔날 게엠베하	중등 지속성 천식의 치료에서 티오트로퓸 염의 용도
ES2298049B1 (es)	2006-07-21	2009-10-20	Laboratorios Almirall S.A.	Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano.
NZ574533A (en)	2006-08-01	2011-05-27	Glaxo Group Ltd	Pyrazolo[3,4-b]pyridine compounds, and their use as pde4 inhibitors
EP1923393A1 (fr) *	2006-11-17	2008-05-21	Boehringer Ingelheim Pharma GmbH & Co. KG	Forme cristalline de tiotropium bromide avec urée
EP1925295A1 (fr) *	2006-11-22	2008-05-28	Boehringer Ingelheim Pharma GmbH & Co. KG	Formule de poudre stable contenant un nouveau anticholinergique
GB0716026D0 (en)	2007-08-16	2007-09-26	Norton Healthcare Ltd	An inhalable medicament
CA2608561A1 (fr) *	2007-10-29	2009-04-29	Carl Paluszkiewicz	Support d'accessoires de deflecteur pour motocyclette
WO2009087419A1 (fr) *	2008-01-10	2009-07-16	Generics [Uk] Limited	Nouveau procédé de préparation d'esters de scopine
US8483831B1 (en)	2008-02-15	2013-07-09	Holaira, Inc.	System and method for bronchial dilation
EP2100598A1 (fr) *	2008-03-13	2009-09-16	Laboratorios Almirall, S.A.	Composition à inhaler comprenant aclidinium pour le traitement de l'asthme et de maladies respiratoires obstructives chroniques
EP2100599A1 (fr)	2008-03-13	2009-09-16	Laboratorios Almirall, S.A.	Composition à inhaler comprenant aclidinium pour le traitement de l'asthme et de maladies respiratoires obstructives chroniques
EP2320821B2 (fr)	2008-05-09	2020-12-30	Nuvaira, Inc.	Système pour le traitement d'un arbre bronchique
EP2172190A1 (fr)	2008-10-02	2010-04-07	Laboratorios Liconsa, S.A.	Particules inhalables comprenant du tiotropium
EP2403851B1 (fr)	2009-03-06	2015-06-17	Mahmut Bilgic	Nouvelles formes cristallines de bromure de tiotropium
US8815258B2 (en)	2009-05-29	2014-08-26	Pearl Therapeutics, Inc.	Compositions, methods and systems for respiratory delivery of two or more active agents
PT2435025T (pt)	2009-05-29	2016-11-11	Pearl Therapeutics Inc	Administração, por via respiratória, de agentes activos
WO2011015884A1 (fr)	2009-08-07	2011-02-10	Generics [Uk] Limited	Procédé pour préparer des esters de scopine
CA2768553C (fr)	2009-08-07	2016-08-02	Generics [Uk] Limited	Anhydrate de bromure de tiotropium
WO2011015883A1 (fr)	2009-08-07	2011-02-10	Generics [Uk] Limited	Solvate de dichlorométhane du bromure de tiotropium et son utilisation
TR200907236A2 (tr)	2009-09-23	2011-04-21	Bi̇lgi̇ç Mahmut	Tiotropyum kuru toz formülasyonunun blister ambalajda taşınması.
TR200907237A2 (tr)	2009-09-23	2011-04-21	B�Lg�� Mahmut	Tiotropyum kuru toz kombinasyonu
CN104856757B (zh)	2009-10-27	2017-06-23	赫莱拉公司	具有可冷却的能量发射组件的递送装置
EP4111995A1 (fr)	2009-11-11	2023-01-04	Nuvaira, Inc.	Appareil pour traiter un tissu et contrôler une sténose
US8911439B2 (en)	2009-11-11	2014-12-16	Holaira, Inc.	Non-invasive and minimally invasive denervation methods and systems for performing the same
TR200909789A2 (tr)	2009-12-25	2011-07-21	B�Lg�� Mahmut	Tiotropyum, budesonid ve bir kromoglisik asit türevi kombinasyonu içeren kuru toz kombinasyonu
TR200909793A2 (tr)	2009-12-25	2011-07-21	B�Lg�� Mahmut	Tiotropyum, mometazon ve bir kromoglisik asit türevi kombinasyonu içeren kuru toz kombinasyonu.
WO2011093809A2 (fr)	2010-01-28	2011-08-04	Mahmut Bilgic	Composition pharmaceutique en poudre sèche comprenant du tiotropium et du ciclésonide
WO2011093812A2 (fr)	2010-01-28	2011-08-04	Mahmut Bilgic	Formulation pharmaceutique comprenant du tiotropium et du budésonide sous forme de poudre sèche
TR200909790A2 (tr)	2009-12-25	2011-07-21	Bi̇lgi̇ç Mahmut	Tiotropyum, formoterol ve bir kromoglisik asit türevi kombinasyonu içeren kuru toz kombinasyonu.
TR201000681A2 (tr) *	2010-01-29	2011-08-22	B�Lg�� Mahmut	İnhalasyon yoluyla alınan kuru toz formülasyonları.
TR200909788A2 (tr)	2009-12-25	2011-07-21	Bi̇lgi̇ç Mahmut	Tiotropyum içeren inhalasyona uygun kuru toz formülasyonu
TR201000679A2 (tr) *	2010-01-29	2011-08-22	B�Lg�� Mahmut	Farmasötik bir kombinasyon içeren kuru toz formülasyonları.
WO2011093810A2 (fr)	2010-01-28	2011-08-04	Bilgic Mahmut	Composition pharmaceutique de poudre sèche comprenant du tiotropium et de la mométasone
US8834931B2 (en)	2009-12-25	2014-09-16	Mahmut Bilgic	Dry powder formulation containing tiotropium for inhalation
TR200909792A2 (tr)	2009-12-25	2011-07-21	B�Lg�� Mahmut	Tiotropyum, kortikosteroid ve bir kromoglisik asit türevi kombinasyonu içeren kuru toz kombinasyonu
EP2528600B1 (fr)	2010-01-28	2016-06-29	Mahmut Bilgic	Composition pharmaceutique de poudre sèche comprenant le tiotropium et le fluticasone
TR201000733A2 (tr)	2010-02-02	2011-08-22	Bi̇lgi̇ç Mahmut	Flutikazon, tiotropyum ve sodyum kromoglikat içeren farmasötik bileşimler.
TR201005222A2 (tr)	2010-04-01	2011-10-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür sentez yöntemi
TR201002520A2 (tr)	2010-04-01	2010-05-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür imalat metodu.
US8957209B2 (en)	2010-04-01	2015-02-17	Mahmut Bilgic	Methods for the synthesis of tiotropium bromide
TR201005221A2 (tr)	2010-04-01	2012-01-23	Bi̇lgi̇ç Mahmut	Geliştirilmiş sentez metodu.
TR201007108A2 (tr)	2010-08-25	2012-03-21	B�Lg�� Mahmut	Yeni tiotropyum bromür kristali ve üretim yöntemi.@
TR201101897A2 (tr)	2011-02-28	2012-09-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür içeren kristal madde
TR201111589A2 (tr)	2011-03-03	2012-09-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür susuz kristal formu.
TR201102068A2 (tr)	2011-03-03	2012-09-21	Bi̇lgi̇ç Mahmut	Tiotropyum bromür içeren kristal maddeler
EP2510928A1 (fr)	2011-04-15	2012-10-17	Almirall, S.A.	Aclidinium pour l'amélioration du sommeil des patients avec des maldadies respiratoires
ITRM20110508A1 (it)	2011-09-27	2013-03-28	Lusochimica Spa	Processo per la preparazione degli esteri della scopina.
US8680297B2 (en)	2011-10-06	2014-03-25	Drug Process Licensing Assoc., LLC	Manufacturing process for tiotropium bromide
CZ304368B6 (cs)	2011-11-28	2014-04-02	Zentiva, K.S.	Směsný solvát tiotropium bromidu a způsob jeho přípravy
GB201200525D0 (en)	2011-12-19	2012-02-29	Teva Branded Pharmaceutical Prod R & D Inc	An inhalable medicament
ES2625498T3 (es) *	2011-12-22	2017-07-19	Cerbios-Pharma S.A.	Proceso continuo para la alquilación de aminas terciarias cíclicas
WO2013109216A2 (fr)	2012-01-16	2013-07-25	Mahmut Bilgic	Préparation de formulations en poudre sèche comprenant du tiotropium
CZ201241A3 (cs)	2012-01-20	2013-07-31	Zentiva, K.S.	Nové polymorfní formy tiotropium jodidu a zpusob jejich prípravy
PT106142B (pt)	2012-02-10	2014-07-18	Hovione Farmaci Ncia S A	Processo para a preparação de brometo de tiotrópio
US20150165038A1 (en)	2012-02-10	2015-06-18	Arven llac Sanayi Ve Ticaret A.S.	Compositions comprising muscarinic receptor antagonist and sorbitol
WO2013127738A1 (fr)	2012-02-28	2013-09-06	Boehringer Ingelheim International Gmbh	Nouvelle formulation de tiotropium contenant un gaz propulseur
CZ304808B6 (cs) *	2012-03-16	2014-11-05	Zentiva, K.S.	Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu a jeho nová forma
CZ305012B6 (cs)	2012-03-30	2015-03-25	Zentiva, K.S.	Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu
US20150174064A1 (en)	2012-07-05	2015-06-25	Arven IIac Sanayi Ve Ticaret A.S.	Compositions comprising muscarinic receptor antagonist and glucose anhydrous
US10105316B2 (en)	2012-07-05	2018-10-23	Arven llac Sanayi Ve Ticaret A.S.	Inhalation compositions comprising muscarinic receptor antagonist
EP2705838A1 (fr)	2012-09-06	2014-03-12	Xspray Microparticles Ab	Préparations de tiotropium
ES2620758T3 (es)	2012-11-05	2017-06-29	Zentiva K.S.	Estabilización de solvatos de tiotropio
US9398933B2 (en)	2012-12-27	2016-07-26	Holaira, Inc.	Methods for improving drug efficacy including a combination of drug administration and nerve modulation
JP6454323B2 (ja)	2013-03-15	2019-01-16	パールセラピューティクス，インコーポレイテッド	粒子状結晶性材料のコンディショニングのための方法及びシステム
KR20150135328A (ko)	2013-04-01	2015-12-02	풀매트릭스 인코퍼레이티드	티오트로피움 건조 분말
EP2913332A1 (fr)	2014-02-27	2015-09-02	Euticals S.P.A.	Forme cristalline de bromure de tiotropium et de lactose
US10034866B2 (en)	2014-06-19	2018-07-31	Teva Branded Pharmaceutical Products R&D, Inc.	Inhalable medicament comprising tiotropium
EP3297607B1 (fr)	2015-05-18	2020-07-22	Glenmark Specialty S.A.	Solution d'inhalation de tiotropium à nébuliser
US9987260B2 (en)	2015-05-18	2018-06-05	Glenmark Specialty S.A.	Tiotropium inhalation solution for nebulization
US10653683B2 (en)	2015-05-18	2020-05-19	Glenmark Specialty S.A.	Tiotropium inhalation solution for nebulization
KR101748796B1 (ko)	2015-09-30	2017-06-19	한미약품 주식회사	활성성분의 전달량이 향상된 흡입용 캡슐제
CA3002300A1 (fr)	2015-10-23	2017-04-27	Arven Ilac Sanayi Ve Ticaret A.S.	Emballage-coque pour formulation inhalable de bromure de tiotropium
EP3159278A1 (fr)	2015-10-23	2017-04-26	Arven Ilac Sanayi Ve Ticaret A.S.	Blister pour formulation pour inhalation à base de bromure de tiotropium
WO2017138896A1 (fr)	2016-02-11	2017-08-17	Sima Patent Ve Lisanslama Hizmetleri Ltd. Şti	Forme cristalline d'anhydrate de bromure de tiotropium
CN106467535A (zh) *	2016-08-28	2017-03-01	杭州百诚医药科技股份有限公司	一种制备2,2‑双(2‑噻吩基)乙醇酸东莨菪酯的纯化工艺
WO2018055642A1 (fr) *	2016-09-23	2018-03-29	Gbr Laboratories Pvt. Ltd.	Procédé de préparation de bromure de tiotropium et de ses intermédiaires
US10555903B2 (en)	2016-10-14	2020-02-11	Glenmark Specialty S.A.	Nebulizable compositions of tiotropium and formoterol
EP3541369A4 (fr)	2016-11-16	2020-06-10	Glenmark Specialty S.A.	Tiotropium nébulisé
WO2020141472A1 (fr)	2019-01-03	2020-07-09	Glenmark Specialty S.A.	Composition de nébulisation comprenant du tiotropium et de l'indacatérol
CA3226155A1 (fr)	2021-07-09	2023-01-12	Astrazeneca Pharmaceuticals Lp	Compositions, methodes et systemes pour l'administration d'un medicament en aerosol
CN114213408B (zh) *	2021-12-15	2023-03-31	台州仙琚药业有限公司	一种噻托溴铵的制备方法
JP2024545816A (ja)	2021-12-20	2024-12-12	アストラゼネカ・アクチエボラーグ	エアロゾル薬物送達のための組成物、方法及びシステム

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB845056A (en)	1957-07-05	1960-08-17	Egyt Gyogyszervegyeszeti Gyar	Improvements in or relating to tropane derivatives
DE1166787B (de) *	1960-07-09	1964-04-02	Boehringer & Soehne Gmbh	Verfahren zur Herstellung von neuen Granatanol-(3ª‰)-estern und ihren Hydrohalogeniden
GB955535A (en) *	1962-10-22	1964-04-15	Boehringer & Soehne Gmbh	New n-substituted norgranatanol-(3ª‰)-esters
DE2046659A1 (fr)	1970-01-28	1972-03-23
US3808263A (en) *	1970-05-12	1974-04-30	Tanabe Seiyaku Co	6,6-dimethyl-9-alkyl-9-azabicyclo(3.3.1)nonan-3-ols
US3673195A (en) *	1970-05-25	1972-06-27	Tanabe Seiyaku Co	Derivatives of 6,6,9-tri-lower alkyl-9-azabicyclo(3.3.1) nonan-3{60 -or 3{62 -ol
US4353922A (en) *	1981-03-13	1982-10-12	Syntex (U.S.A.) Inc.	Anticholinergic bronchodilators
DE3546218A1 (de)	1985-12-27	1987-07-02	Madaus & Co Dr	Azoniaspironortropanolester, verfahren zu deren herstellung und pharmazeutisches mittel
DE3931041C2 (de)	1989-09-16	2000-04-06	Boehringer Ingelheim Kg	Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel

1989
- 1989-09-16 DE DE3931041A patent/DE3931041C2/de not_active Expired - Lifetime
1990
- 1990-09-06 DD DD90343854A patent/DD297647A5/de not_active IP Right Cessation
- 1990-09-08 CA CA002066248A patent/CA2066248C/fr not_active Expired - Lifetime
- 1990-09-08 AU AU64318/90A patent/AU642913B2/en not_active Expired
- 1990-09-08 HU HU9200857A patent/HU208823B/hu unknown
- 1990-09-08 UA UA93060616A patent/UA41272C2/uk unknown
- 1990-09-08 JP JP2513253A patent/JPH0730074B2/ja not_active Expired - Lifetime
- 1990-09-08 WO PCT/EP1990/001517 patent/WO1991004252A1/fr not_active Ceased
- 1990-09-08 RU SU905011520A patent/RU2073677C1/ru active
- 1990-09-12 EP EP90117554A patent/EP0418716B1/fr not_active Expired - Lifetime
- 1990-09-12 AT AT90117554T patent/ATE103914T1/de active
- 1990-09-12 ES ES90117554T patent/ES2052125T3/es not_active Expired - Lifetime
- 1990-09-12 DE DE2002199026 patent/DE10299026I2/de active Active
- 1990-09-12 DE DE90117554T patent/DE59005250D1/de not_active Expired - Lifetime
- 1990-09-12 DK DK90117554.7T patent/DK0418716T3/da active
- 1990-09-13 SI SI9011744A patent/SI9011744B/sl unknown
- 1990-09-13 YU YU174490A patent/YU47800B/sh unknown
- 1990-09-14 PT PT95312A patent/PT95312B/pt not_active IP Right Cessation
- 1990-09-14 PH PH41212A patent/PH31617A/en unknown
- 1990-09-14 KR KR1019900014543A patent/KR0168432B1/ko not_active Expired - Lifetime
- 1990-09-14 ZA ZA907338A patent/ZA907338B/xx unknown
- 1990-09-14 NZ NZ235306A patent/NZ235306A/en unknown
- 1990-09-14 IL IL9569190A patent/IL95691A/en active Protection Beyond IP Right Term
- 1990-09-17 CZ CS904523A patent/CZ284589B6/cs not_active IP Right Cessation
- 1990-09-17 SK SK4523-90A patent/SK279453B6/sk not_active IP Right Cessation
1992
- 1992-03-13 IE IE334290A patent/IE65528B1/en active Protection Beyond IP Right Term
- 1992-03-13 FI FI921087A patent/FI114395B/fi active Protection Beyond IP Right Term
- 1992-03-13 NO NO921002A patent/NO301478B1/no not_active IP Right Cessation
- 1992-03-13 PL PL90286900A patent/PL168468B1/pl active Protection Beyond IP Right Term
- 1992-06-23 MX MX9203150A patent/MX9203150A/es unknown
1994
- 1994-02-23 BG BG098532A patent/BG61295B2/bg unknown
- 1994-10-21 HR HRP-1744/90A patent/HRP940723B1/xx not_active IP Right Cessation
- 1994-12-15 HU HU94P/P00055P patent/HU210612A9/hu unknown
2002
- 2002-02-14 NL NL300084C patent/NL300084I2/nl unknown
- 2002-08-30 LU LU90949C patent/LU90949I2/fr unknown
- 2002-09-17 NO NO2002009C patent/NO2002009I2/no unknown
2005
- 2005-10-18 US US11/254,213 patent/USRE39820E1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU642913B2 (en)	1993-11-04
IE65528B1 (en)	1995-11-01
DE10299026I2 (de)	2004-07-01
NO921002D0 (no)	1992-03-13
NO2002009I2 (no)	2004-10-11
HU208823B (en)	1994-01-28
HRP940723B1 (en)	1999-10-31
IE903342A1 (en)	1991-04-10
NO921002L (no)	1992-03-13
DE59005250D1 (de)	1994-05-11
ZA907338B (en)	1992-08-26
HU9200857D0 (en)	1992-05-28
DE10299026I1 (de)	2002-11-07
WO1991004252A1 (fr)	1991-04-04
YU174490A (sh)	1993-10-20
SI9011744A (en)	1997-10-31
RU2073677C1 (ru)	1997-02-20
NZ235306A (en)	1997-06-24
PL168468B1 (pl)	1996-02-29
SI9011744B (sl)	1999-12-31
USRE39820E1 (en)	2007-09-04
KR0168432B1 (ko)	1999-01-15
EP0418716B1 (fr)	1994-04-06
NL300084I1 (nl)	2002-05-01
NL300084I2 (nl)	2002-08-01
LU90949I2 (fr)	2002-10-30
HUT60740A (en)	1992-10-28
CA2066248A1 (fr)	1991-03-17
DE3931041A1 (de)	1991-03-28
AU6431890A (en)	1991-04-18
FI921087A0 (fi)	1992-03-13
PT95312A (pt)	1991-05-22
DK0418716T3 (da)	1994-05-02
JPH0730074B2 (ja)	1995-04-05
NO301478B1 (no)	1997-11-03
HRP940723A2 (en)	1997-06-30
EP0418716A1 (fr)	1991-03-27
PL286900A1 (en)	1991-12-02
ES2052125T3 (es)	1994-07-01
CA2066248C (fr)	1998-08-04
PH31617A (en)	1999-01-12
SK452390A3 (en)	1998-11-04
IL95691A (en)	1996-07-23
SK279453B6 (sk)	1998-11-04
CZ452390A3 (cs)	1998-11-11
JPH05502438A (ja)	1993-04-28
BG61295B2 (bg)	1997-04-30
IL95691A0 (en)	1991-06-30
HU210612A9 (en)	1995-05-29
KR910006272A (ko)	1991-04-29
PT95312B (pt)	1997-06-30
CZ284589B6 (cs)	1999-01-13
MX9203150A (es)	1992-07-01
DE3931041C2 (de)	2000-04-06
UA41272C2 (uk)	2001-09-17
ATE103914T1 (de)	1994-04-15
FI114395B (fi)	2004-10-15
YU47800B (sr)	1996-01-09

Legal Events

Date	Code	Title	Description
1997-07-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0418716B1 (fr)	1994-04-06	Esters aminoalcohol d'acide thienylcarboxyliques leurs produits quaternaires, leur préparation et l'utilisation de ces composés
EP0579615B1 (fr)	2001-07-04	Esters nouveaux d'amino-alcools bicycliques et tricycliques, leur preparation et leur utilisation dans des medicaments
EP1426373B1 (fr)	2006-08-23	Procédé de fabrication d'un précurseur de l'agent anticholinergique bromure de tiotropium
DE3687980T2 (de)	1993-06-17	Indolderivate mit einer azabicyclischen seitenkette, verfahren zu ihrer herstellung, zwischenprodukte und pharmazeutische zusammensetzungen.
DE69929235T2 (de)	2006-08-24	Spiro-indole als y5-rezeptor antagonisten
DE3785507T2 (de)	1993-07-29	Azabicyclische verbindungen, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung.
DE3850742T2 (de)	1994-10-27	Neue 4-Oxobenzotriazine und 4-Oxochinazoline.
DE3852145T2 (de)	1995-04-06	Indolderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, die diese enthalten.
DE3782107T2 (de)	1993-04-01	Azabicyclische verbindungen, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung.
WO1984000166A1 (fr)	1984-01-19	Derives d'ester piperidyl d'acide benzoique et procede de production et d'utilisation de ces composes
DE3881950T2 (de)	1993-09-30	Azabicyclische Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen.
DE69200290T2 (de)	1995-02-16	Thienopyridin -Derivative und diese enthaltende Arzneimittel.
EP1527073B1 (fr)	2007-08-22	Urees de benzothiophene, de benzofuranne et d'indole et utilisation de ces urees comme agonistes des achr alpha 7
DE69133295T2 (de)	2004-03-18	3,9-diazabicyclo-[3.3.1]-nonanylderivate, verfahren und intermediate für ihre darstellung und sie enthaltende pharmazeutische zusammensetzungen
EP1475379B1 (fr)	2007-04-11	Utilisation des derivés de ester des scopine pour la fabrication de medicaments
DE69205312T2 (de)	1996-03-14	Substituierte Imidazol-2-one Derivate und Verfahren zu deren Herstellung.
DE69113284T2 (de)	1996-02-22	Chinolinderivat.
DE3687515T2 (de)	1993-05-13	Oxa-, thia- und diazabicycloalkanderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.
DE4123587A1 (de)	1993-01-14	2,14-disubstituierte ergoline, deren herstellung und verwendung in arzneimitteln
DE69328701T2 (de)	2000-11-02	Diazabicycloderivate als 5-HT3-Antagonisten
US3502683A (en)	1970-03-24	Certain n-substituted noratropine and nortropidine tropic acid esters and derivatives thereof
EP2036898A2 (fr)	2009-03-18	Procédé de fabrication de 1,3-dioxolan-2ons ainsi qu'éthers d'acide carbonique par transacylation à liaisons de réactions basiques
US3583996A (en)	1971-06-08	Process for the preparation of certain alkaloid alcohol esters of tropic acid
DD299430A5 (de)	1992-04-16	Neue 1-oxa-2-oxo-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung
EP1513838B1 (fr)	2006-07-26	Procede technique de fabrication de tropenol