UA79986C2 - Intermediate and process for the preparation of oxabispidine compounds using thereof - Google Patents

Intermediate and process for the preparation of oxabispidine compounds using thereof Download PDF

Info

Publication number: UA79986C2
Authority: UA; Ukraine
Prior art keywords: aryl; alkyl; salt; optionally substituted; independently represent
Prior art date: 2002-10-14

Application number

UAA200502926A

Other languages

English (en)

Ukrainian (uk)

Inventor

David Cladingboel

Original Assignee

Astrazeneca Ab

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.)

2002-10-14

Filing date

2003-10-13

Publication date

2007-08-10

2003-10-13 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-08-10 Publication of UA79986C2 publication Critical patent/UA79986C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 37
238000000034 method Methods 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title description 4
230000008569 process Effects 0.000 title description 2
125000003118 aryl group Chemical group 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 22
125000001424 substituent group Chemical group 0.000 claims abstract description 19
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
125000004104 aryloxy group Chemical group 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
239000007787 solid Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 13
-1 C.ialkyloxy Chemical group 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
LXFQSRIDYRFTJW-UHFFFAOYSA-M 2,4,6-trimethylbenzenesulfonate Chemical group CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-M 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims description 2
SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
229940077388 benzenesulfonate Drugs 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000012634 fragment Substances 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
230000003993 interaction Effects 0.000 claims 2
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
NAASACDEWDVNER-UHFFFAOYSA-N tert-butyl 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S(=O)(=O)OC(C)(C)C)C(C)=C1 NAASACDEWDVNER-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 20
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 18
239000012071 phase Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
238000003756 stirring Methods 0.000 description 11
239000000047 product Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
238000004821 distillation Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
239000012265 solid product Substances 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
230000008901 benefit Effects 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000005406 washing Methods 0.000 description 3
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241001150538 Iria Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 2
NHDLUSFFYRBOLY-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-benzyl-1,5-diazocane-3,7-diol Chemical compound C1C(O)CN(S(=O)(=O)C=2C=CC=CC=2)CC(O)CN1CC1=CC=CC=C1 NHDLUSFFYRBOLY-UHFFFAOYSA-N 0.000 description 1
LEKJAKPBCODASB-UHFFFAOYSA-N 1-hydroxy-1,5-diazocan-3-ol Chemical class OC1CNCCCN(O)C1 LEKJAKPBCODASB-UHFFFAOYSA-N 0.000 description 1
XNJVIJQATFJERB-UHFFFAOYSA-N 2,3,4-trimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C)=C1C XNJVIJQATFJERB-UHFFFAOYSA-N 0.000 description 1
LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 1
PBZZGDPOFJLGAA-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S(=O)(=O)OCCNC(=O)OC(C)(C)C)C(C)=C1 PBZZGDPOFJLGAA-UHFFFAOYSA-N 0.000 description 1
HMXJZAZRNMXNIF-UHFFFAOYSA-N 6-oxa-1,3-diazatricyclo[3.3.1.13,7]decane Chemical class C1N(C2)CC3CN2CC1O3 HMXJZAZRNMXNIF-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000013014 purified material Substances 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
ISTGQSQWSKCNFJ-UHFFFAOYSA-N tert-butyl n-ethylcarbamate Chemical class CCNC(=O)OC(C)(C)C ISTGQSQWSKCNFJ-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Extraction Or Liquid Replacement (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UAA200502926A 2002-10-14 2003-10-13 Intermediate and process for the preparation of oxabispidine compounds using thereof UA79986C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0223712.1A GB0223712D0 (en)	2002-10-14	2002-10-14	Chemical intermediate
PCT/SE2003/001594 WO2004035592A1 (en)	2002-10-14	2003-10-13	Chemical intermediate

Publications (1)

Publication Number	Publication Date
UA79986C2 true UA79986C2 (en)	2007-08-10

Family

ID=9945773

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200502926A UA79986C2 (en)	2002-10-14	2003-10-13	Intermediate and process for the preparation of oxabispidine compounds using thereof

Country Status (25)

Country	Link
US (2)	US7314931B2 (pl)
EP (1)	EP1554285B1 (pl)
JP (1)	JP4476810B2 (pl)
KR (1)	KR20050056239A (pl)
CN (1)	CN1319976C (pl)
AT (1)	ATE455118T1 (pl)
AU (1)	AU2003269768B2 (pl)
BR (1)	BR0315112A (pl)
CA (1)	CA2501413A1 (pl)
DE (1)	DE60330982D1 (pl)
DK (1)	DK1554285T3 (pl)
ES (1)	ES2337998T3 (pl)
GB (1)	GB0223712D0 (pl)
IL (1)	IL167778A (pl)
IS (1)	IS7841A (pl)
MX (1)	MXPA05003812A (pl)
NO (1)	NO20051627L (pl)
NZ (1)	NZ539371A (pl)
PL (1)	PL375100A1 (pl)
PT (1)	PT1554285E (pl)
RU (1)	RU2326122C2 (pl)
SI (1)	SI1554285T1 (pl)
UA (1)	UA79986C2 (pl)
WO (1)	WO2004035592A1 (pl)
ZA (1)	ZA200502579B (pl)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR030756A1 (es) *	2000-10-02	2003-09-03	Astrazeneca Ab	Compuesto de oxabispidina util en el tratamiento de arritmias cardiacas
GB0223712D0 (en) *	2002-10-14	2002-11-20	Astrazeneca Ab	Chemical intermediate
SE0401539D0 (sv)	2004-06-15	2004-06-15	Astrazeneca Ab	New compounds
JP2008543750A (ja) *	2005-06-13	2008-12-04	アストラゼネカアクチボラグ	心不整脈の処置用の新規オキサビスピジン化合物
US20100222335A1 (en) *	2005-06-20	2010-09-02	Astrazeneca Ab	Process For The Preparation Of N,N'-Disubstituted Oxabispidines
WO2006137772A1 (en) *	2005-06-20	2006-12-28	Astrazeneca Ab	New physical form of n,n´- disubstituted oxabispidines
CA2610093A1 (en) *	2005-06-20	2006-12-28	Astrazeneca Ab	Process for the preparation of sulfonic acid salts of oxabispidines
AR054391A1 (es) *	2005-06-20	2007-06-20	Astrazeneca Ab	Procedimiento para la preparacion de 3,7- dihidroxi-1,5-diazaciclooctanos
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2002
- 2002-10-14 GB GBGB0223712.1A patent/GB0223712D0/en not_active Ceased
2003
- 2003-10-13 KR KR1020057006247A patent/KR20050056239A/ko not_active Ceased
- 2003-10-13 JP JP2004545133A patent/JP4476810B2/ja not_active Expired - Lifetime
- 2003-10-13 WO PCT/SE2003/001594 patent/WO2004035592A1/en not_active Ceased
- 2003-10-13 DE DE60330982T patent/DE60330982D1/de not_active Expired - Lifetime
- 2003-10-13 SI SI200331761T patent/SI1554285T1/sl unknown
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- 2003-10-13 AU AU2003269768A patent/AU2003269768B2/en not_active Ceased
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- 2003-10-13 RU RU2005109158/04A patent/RU2326122C2/ru not_active IP Right Cessation
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Also Published As

Publication number	Publication date
CN1319976C (zh)	2007-06-06
US20060199814A1 (en)	2006-09-07
EP1554285B1 (en)	2010-01-13
JP4476810B2 (ja)	2010-06-09
EP1554285A1 (en)	2005-07-20
IL167778A (en)	2010-04-29
HK1078861A1 (en)	2006-03-24
HK1082498A1 (en)	2006-06-09
ATE455118T1 (de)	2010-01-15
GB0223712D0 (en)	2002-11-20
US7314931B2 (en)	2008-01-01
MXPA05003812A (es)	2005-06-08
SI1554285T1 (sl)	2010-04-30
BR0315112A (pt)	2005-08-16
DK1554285T3 (da)	2010-04-19
ZA200502579B (en)	2006-02-22
KR20050056239A (ko)	2005-06-14
RU2326122C2 (ru)	2008-06-10
DE60330982D1 (de)	2010-03-04
ES2337998T3 (es)	2010-05-03
WO2004035592A1 (en)	2004-04-29
NZ539371A (en)	2006-10-27
US20090062532A1 (en)	2009-03-05
IS7841A (is)	2005-05-12
CN1705671A (zh)	2005-12-07
AU2003269768A1 (en)	2004-05-04
JP2006505565A (ja)	2006-02-16
NO20051627L (no)	2005-05-06
CA2501413A1 (en)	2004-04-29
PT1554285E (pt)	2010-03-08
RU2005109158A (ru)	2006-01-20
AU2003269768B2 (en)	2007-08-23
PL375100A1 (pl)	2005-11-14

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US20090062532A1 (en)	2009-03-05	Chemical Intermediate
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HK1078861B (en)	2010-07-23	Chemical intermediate
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