NO331985B1 - Fremgangsmate for fremstilling av 5-[(R)(5,6-dietyl-indan-2-ylamino)-1-hydroksyetyl]-8-hydroksy-(1H)-kinolin-2-on-salt som er nyttig som adrenoreseptoragonist, samt mellomprodukter - Google Patents

Fremgangsmate for fremstilling av 5-[(R)(5,6-dietyl-indan-2-ylamino)-1-hydroksyetyl]-8-hydroksy-(1H)-kinolin-2-on-salt som er nyttig som adrenoreseptoragonist, samt mellomprodukter Download PDF

Info

Publication number: NO331985B1
Authority: NO; Norway
Prior art keywords: quinolin; formula; hydroxy; salt; diethyl
Prior art date: 2003-02-28

Application number

NO20054452A

Other languages

English (en)

Norwegian (no)

Other versions

NO20054452D0 (no

NO20054452L (no

Inventor

Olivier Lohse

Caspar Vogel

Original Assignee

Novartis Ag

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.)

2003-02-28

Filing date

2005-09-26

Publication date

2012-05-21

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32927689&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO331985(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2005-09-26 Application filed by Novartis Ag filed Critical Novartis Ag

2005-09-26 Publication of NO20054452D0 publication Critical patent/NO20054452D0/no

2005-11-28 Publication of NO20054452L publication Critical patent/NO20054452L/no

2012-05-21 Publication of NO331985B1 publication Critical patent/NO331985B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims abstract description 12
QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical class N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 title abstract description 4
239000000048 adrenergic agonist Substances 0.000 title 1
239000000543 intermediate Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 48
-1 5,6-diethyl-indan-2-ylamino Chemical group 0.000 claims abstract description 32
239000002904 solvent Substances 0.000 claims description 48
125000006239 protecting group Chemical group 0.000 claims description 27
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
239000002585 base Substances 0.000 claims description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
239000005711 Benzoic acid Substances 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
235000010233 benzoic acid Nutrition 0.000 claims description 8
238000001914 filtration Methods 0.000 claims description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
239000003638 chemical reducing agent Substances 0.000 claims description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
150000001558 benzoic acid derivatives Chemical class 0.000 claims description 5
239000011976 maleic acid Substances 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
239000000843 powder Substances 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
229910052697 platinum Inorganic materials 0.000 claims description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 4
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
229910000085 borane Inorganic materials 0.000 claims description 3
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
XNJGWTIQYUPOAF-UHFFFAOYSA-N 1,3,2-oxazaborole Chemical compound O1B=NC=C1 XNJGWTIQYUPOAF-UHFFFAOYSA-N 0.000 claims description 2
AFXKCBFBGDUFAM-UHFFFAOYSA-N 2-methylpropan-2-amine;hydrofluoride Chemical compound [F-].CC(C)(C)[NH3+] AFXKCBFBGDUFAM-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 claims description 2
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 2
239000011698 potassium fluoride Substances 0.000 claims description 2
235000003270 potassium fluoride Nutrition 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 3
239000004305 biphenyl Substances 0.000 claims 1
KHYAFFAGZNCWPT-UHFFFAOYSA-N boron;n,n-diethylaniline Chemical compound [B].CCN(CC)C1=CC=CC=C1 KHYAFFAGZNCWPT-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 10
239000012458 free base Substances 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 9
125000001931 aliphatic group Chemical group 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
239000004793 Polystyrene Substances 0.000 description 6
125000005233 alkylalcohol group Chemical group 0.000 description 6
239000003125 aqueous solvent Substances 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000001983 dialkylethers Chemical class 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
239000002608 ionic liquid Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
HXJUTPCZVOIRIF-UHFFFAOYSA-N Tetrahydrothiophene-1,1-dioxide, Natural products O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
150000003973 alkyl amines Chemical class 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
229940011051 isopropyl acetate Drugs 0.000 description 4
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
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125000005842 heteroatom Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000002950 monocyclic group Chemical group 0.000 description 3
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239000001301 oxygen Chemical group 0.000 description 3
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229920001223 polyethylene glycol Polymers 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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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 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
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 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
108060003345 Adrenergic Receptor Proteins 0.000 description 1
102000017910 Adrenergic receptor Human genes 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
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229910003849 O-Si Inorganic materials 0.000 description 1
229910003872 O—Si Inorganic materials 0.000 description 1
239000005864 Sulphur Chemical group 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
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208000006673 asthma Diseases 0.000 description 1
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229910000024 caesium carbonate Inorganic materials 0.000 description 1
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LISFMEBWQUVKPJ-UHFFFAOYSA-N carbostyril Natural products C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
IREJFXIHXRZFER-PCBAQXHCSA-N indacaterol maleate Chemical compound OC(=O)\C=C/C(O)=O.N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 IREJFXIHXRZFER-PCBAQXHCSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000001725 pyrenyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010583 slow cooling Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Materials Engineering (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO20054452A 2003-02-28 2005-09-26 Fremgangsmate for fremstilling av 5-[(R)(5,6-dietyl-indan-2-ylamino)-1-hydroksyetyl]-8-hydroksy-(1H)-kinolin-2-on-salt som er nyttig som adrenoreseptoragonist, samt mellomprodukter NO331985B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US45094503P	2003-02-28	2003-02-28
PCT/EP2004/001981 WO2004076422A1 (en)	2003-02-28	2004-02-27	Process for preparing 5-‘(r)-2-(5,6-diethyl-indian-2-ylamino)-1-hydroxy-ethyl!-8-hydroxy-(1h)-quinolin-2-one salt, useful as an adrenoceptor agonist

Publications (3)

Publication Number	Publication Date
NO20054452D0 NO20054452D0 (no)	2005-09-26
NO20054452L NO20054452L (no)	2005-11-28
NO331985B1 true NO331985B1 (no)	2012-05-21

Family

ID=32927689

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20054452A NO331985B1 (no)	2003-02-28	2005-09-26	Fremgangsmate for fremstilling av 5-[(R)(5,6-dietyl-indan-2-ylamino)-1-hydroksyetyl]-8-hydroksy-(1H)-kinolin-2-on-salt som er nyttig som adrenoreseptoragonist, samt mellomprodukter

Country Status (30)

Country	Link
US (1)	US7534890B2 (es)
EP (1)	EP1599450B1 (es)
JP (1)	JP4802089B2 (es)
KR (1)	KR101076929B1 (es)
CN (1)	CN100363349C (es)
AR (1)	AR043406A1 (es)
AT (1)	ATE434609T1 (es)
AU (1)	AU2004215647B2 (es)
BR (1)	BRPI0407904B1 (es)
CA (1)	CA2517033C (es)
CL (1)	CL2004000381A1 (es)
CY (1)	CY1109442T1 (es)
DE (1)	DE602004021675D1 (es)
DK (1)	DK1599450T3 (es)
EC (1)	ECSP055977A (es)
ES (1)	ES2326974T3 (es)
HK (1)	HK1086255A1 (es)
IL (1)	IL170138A (es)
MX (1)	MXPA05009156A (es)
MY (1)	MY142491A (es)
NO (1)	NO331985B1 (es)
NZ (1)	NZ541727A (es)
PE (1)	PE20040956A1 (es)
PL (1)	PL213932B1 (es)
PT (1)	PT1599450E (es)
RU (1)	RU2332405C2 (es)
SI (1)	SI1599450T1 (es)
TW (1)	TWI324150B (es)
WO (1)	WO2004076422A1 (es)
ZA (1)	ZA200506060B (es)

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PE20050211A1 (es) *	2003-04-02	2005-04-27	Novartis Ag	Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas
BRPI0409198A (pt) *	2003-04-04	2006-05-02	Novartis Ag	derivados quinolin-2-ona para o tratamento de doenças de vias aéreas
GB0411056D0 (en)	2004-05-18	2004-06-23	Novartis Ag	Organic compounds
GB0413960D0 (en) *	2004-06-22	2004-07-28	Novartis Ag	Organic compounds
DK2044025T3 (da)	2006-06-30	2013-01-14	Novartis Ag	Quinolinonderivater samt farmaceutiske sammensætninger deraf
JP2010520188A (ja)	2007-02-28	2010-06-10	シプラ・リミテッド	カルモテロールの異性体を調製する方法
WO2011056929A1 (en) *	2009-11-04	2011-05-12	Massachusetts Institute Of Technology	Continuous flow synthesis of amino alcohols using microreactors
US8680303B2 (en)	2010-03-01	2014-03-25	Massachusetts Institute Of Technology	Epoxidation catalysts
WO2013132514A2 (en) *	2012-03-09	2013-09-12	Rao Davuluri Ramamohan	A novel process for the preparation of (r)-5-[2-[(5, 6-diethyl-2, 3-dihydro-1h-inden-2-yl) amino]-1-hydroxyethyl]-8-hydroxy quinolin-2(1h)-one
WO2014008639A1 (zh) *	2012-07-11	2014-01-16	上海威智医药科技有限公司	制备茚达特罗的方法
CN104379566B (zh) *	2012-07-11	2016-08-24	上海威智医药科技有限公司	茚达特罗中间体及茚达特罗的合成方法
WO2014044288A1 (en) *	2012-09-21	2014-03-27	Crystal Pharma Sa	Methods for the preparation of indacaterol and pharmaceutically acceptable salts thereof
EP3138837B1 (en)	2012-09-21	2021-11-24	Crystal Pharma, S.A.U.	Indacaterol free base in solid form
CZ306252B6 (cs)	2013-03-15	2016-10-26	Zentiva, K.S.	Způsob přípravy 5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-(1H)-chinolin-2-onu (indacaterolu)
ES2626829T3 (es) *	2013-03-27	2017-07-26	Laboratorios Lesvi, S.L.	Procedimiento para la fabricación de (R)-5[2-(5,6-dietil-indan-2-ilamino)-1-hidroxietil]-8-hidroxi-(1H)-quinolin-2-ona
WO2015104718A2 (en)	2014-01-09	2015-07-16	Davuluri, Ramamohan Rao	A novel process for preparation of indacaterol or its pharmaceutically acceptable salts
WO2016027283A2 (en)	2014-08-22	2016-02-25	Reddy G Pratap	A process for preparing indacaterol and salts thereof
CN105693603B (zh) *	2014-11-24	2019-11-29	上海医药工业研究院	改良的马来酸茚达特罗制备工艺
WO2016161956A1 (zh) *	2015-04-09	2016-10-13	正大天晴药业集团股份有限公司	茚达特罗或其盐的制备方法
US20190185461A1 (en) *	2015-07-21	2019-06-20	Sichuan Haisco Pharmaceutical Co., Ltd.	Benzocyclic derivative having b2-receptor agonist activity and m3-receptor antagonist activity and medical use thereof
WO2017055506A1 (en)	2015-09-29	2017-04-06	Laboratorios Lesvi, S.L.	Mixed solvate of (r)-5-[2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl] -8-hydroxy-1h-quinolin-2-one l-tartrate
CN107021921A (zh) *	2016-02-02	2017-08-08	常州爱诺新睿医药技术有限公司	一种茚达特罗中间体的盐及其制备方法
CN107868045A (zh) *	2016-09-28	2018-04-03	四川海思科制药有限公司	一种茚达特罗中间体的制备方法
CN108101841B (zh) *	2016-11-24	2021-04-06	江苏恒瑞医药股份有限公司	一种制备茚达特罗或其盐的方法
CN108264483A (zh) *	2016-12-31	2018-07-10	天津金耀集团有限公司	一种马来酸茚达特罗的制备方法
CN109516974B (zh) *	2017-09-19	2022-05-27	南京圣和药业股份有限公司	取代嘧啶类pi3k抑制剂的制备方法
WO2019135101A1 (en)	2018-01-02	2019-07-11	Deva Holding Anonim Sirketi	A process for preparation of 5-(2-(substituted-amino)-1-hydroxyethyl)-8-(substituted-oxy) quinolin-2(1h)-one
CN109721534B (zh) *	2018-09-25	2022-05-20	四川海思科制药有限公司	一种马来酸茚达特罗中间体及其制备方法和用途
CN109988111A (zh) *	2019-05-06	2019-07-09	淮北师范大学	一种马来酸茚达特罗的杂质及其合成方法
CN110128339B (zh) *	2019-05-31	2022-03-08	苏州芝宇生物科技有限公司	一种茚达特罗及其盐衍生物的合成方法和合成用中间体
CN113731406B (zh) *	2021-10-12	2023-07-28	南京工业大学	一种提高钯碳活性加氢脱除保护基的方法

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2004
- 2004-02-25 TW TW093104788A patent/TWI324150B/zh not_active IP Right Cessation
- 2004-02-26 PE PE2004000198A patent/PE20040956A1/es not_active Application Discontinuation
- 2004-02-26 AR ARP040100606A patent/AR043406A1/es not_active Application Discontinuation
- 2004-02-27 MX MXPA05009156A patent/MXPA05009156A/es active IP Right Grant
- 2004-02-27 WO PCT/EP2004/001981 patent/WO2004076422A1/en active Application Filing
- 2004-02-27 AU AU2004215647A patent/AU2004215647B2/en not_active Expired
- 2004-02-27 SI SI200431222T patent/SI1599450T1/sl unknown
- 2004-02-27 JP JP2006501972A patent/JP4802089B2/ja not_active Expired - Lifetime
- 2004-02-27 ES ES04715306T patent/ES2326974T3/es not_active Expired - Lifetime
- 2004-02-27 PT PT04715306T patent/PT1599450E/pt unknown
- 2004-02-27 DE DE602004021675T patent/DE602004021675D1/de not_active Expired - Lifetime
- 2004-02-27 CL CL200400381A patent/CL2004000381A1/es unknown
- 2004-02-27 RU RU2005129547/04A patent/RU2332405C2/ru active
- 2004-02-27 PL PL378358A patent/PL213932B1/pl unknown
- 2004-02-27 CN CNB2004800054167A patent/CN100363349C/zh not_active Expired - Lifetime
- 2004-02-27 AT AT04715306T patent/ATE434609T1/de active
- 2004-02-27 CA CA2517033A patent/CA2517033C/en not_active Expired - Lifetime
- 2004-02-27 MY MYPI20040645A patent/MY142491A/en unknown
- 2004-02-27 EP EP04715306A patent/EP1599450B1/en not_active Expired - Lifetime
- 2004-02-27 DK DK04715306T patent/DK1599450T3/da active
- 2004-02-27 NZ NZ541727A patent/NZ541727A/en not_active IP Right Cessation
- 2004-02-27 US US10/546,941 patent/US7534890B2/en active Active
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2005
- 2005-07-28 ZA ZA200506060A patent/ZA200506060B/en unknown
- 2005-08-07 IL IL170138A patent/IL170138A/en active IP Right Grant
- 2005-08-24 EC EC2005005977A patent/ECSP055977A/es unknown
- 2005-08-26 KR KR1020057015981A patent/KR101076929B1/ko active IP Right Grant
- 2005-09-26 NO NO20054452A patent/NO331985B1/no unknown
2006
- 2006-05-24 HK HK06105984.1A patent/HK1086255A1/xx not_active IP Right Cessation
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Also Published As

Publication number	Publication date
AU2004215647B2 (en)	2006-12-21
ECSP055977A (es)	2006-01-16
AR043406A1 (es)	2005-07-27
PT1599450E (pt)	2009-08-31
RU2332405C2 (ru)	2008-08-27
PE20040956A1 (es)	2005-01-20
JP4802089B2 (ja)	2011-10-26
NO20054452D0 (no)	2005-09-26
TW200505864A (en)	2005-02-16
CN1753874A (zh)	2006-03-29
WO2004076422A1 (en)	2004-09-10
EP1599450B1 (en)	2009-06-24
SI1599450T1 (sl)	2009-12-31
NO20054452L (no)	2005-11-28
MXPA05009156A (es)	2005-10-20
MY142491A (en)	2010-11-30
KR101076929B1 (ko)	2011-10-26
DK1599450T3 (da)	2009-10-05
JP2006519206A (ja)	2006-08-24
CY1109442T1 (el)	2014-08-13
CL2004000381A1 (es)	2005-01-14
RU2005129547A (ru)	2007-04-10
US7534890B2 (en)	2009-05-19
DE602004021675D1 (de)	2009-08-06
ZA200506060B (en)	2006-07-26
PL378358A1 (pl)	2006-03-20
ES2326974T3 (es)	2009-10-22
HK1086255A1 (en)	2006-09-15
BRPI0407904A (pt)	2006-02-14
EP1599450A1 (en)	2005-11-30
AU2004215647A1 (en)	2004-09-10
CN100363349C (zh)	2008-01-23
KR20050105258A (ko)	2005-11-03
ATE434609T1 (de)	2009-07-15
IL170138A (en)	2011-09-27
TWI324150B (en)	2010-05-01
CA2517033C (en)	2011-11-15
CA2517033A1 (en)	2004-09-10
NZ541727A (en)	2008-07-31
BRPI0407904B1 (pt)	2016-09-20
PL213932B1 (pl)	2013-05-31
US20060252794A1 (en)	2006-11-09

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