ZA200605784B - Process for preparation of 1-(2S,3S)-2-benzhydryl-N-(5-Tert-Butyl-2-methoxybenzyl)quinuclidin-3-amine - Google Patents
Process for preparation of 1-(2S,3S)-2-benzhydryl-N-(5-Tert-Butyl-2-methoxybenzyl)quinuclidin-3-amine Download PDFInfo
- Publication number
- ZA200605784B ZA200605784B ZA200605784A ZA200605784A ZA200605784B ZA 200605784 B ZA200605784 B ZA 200605784B ZA 200605784 A ZA200605784 A ZA 200605784A ZA 200605784 A ZA200605784 A ZA 200605784A ZA 200605784 B ZA200605784 B ZA 200605784B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- process according
- palladium
- carbon
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 66
- 230000008569 process Effects 0.000 title claims description 63
- 238000002360 preparation method Methods 0.000 title description 23
- 150000001875 compounds Chemical class 0.000 claims description 165
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 58
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 32
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- -1 2,4-dimethoxybenzyl Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 238000006268 reductive amination reaction Methods 0.000 claims description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 description 115
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 238000001914 filtration Methods 0.000 description 13
- 238000004821 distillation Methods 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
- 238000007792 addition Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229960004106 citric acid Drugs 0.000 description 9
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- 239000011369 resultant mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- REUAXQZIRFXQML-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2C(N)CN1CC2 REUAXQZIRFXQML-UHFFFAOYSA-N 0.000 description 5
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010956 selective crystallization Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OBYAZZBWVOYPRX-UHFFFAOYSA-N 5-tert-butyl-2-methoxybenzaldehyde Chemical compound COC1=CC=C(C(C)(C)C)C=C1C=O OBYAZZBWVOYPRX-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- MIOPJNTWMNEORI-MHPPCMCBSA-N [(4r)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-MHPPCMCBSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical class C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 description 1
- WGRCQSJMPSCJPV-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine 2-hydroxypropane-1,2,3-tricarboxylic acid hydrate Chemical compound O.NC1CN2CCC1CC2.OC(=O)CC(O)(CC(O)=O)C(O)=O WGRCQSJMPSCJPV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ATUOYWHBWRKTHZ-WFVSFCRTSA-N 2-deuteriopropane Chemical compound [2H]C(C)C ATUOYWHBWRKTHZ-WFVSFCRTSA-N 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101000685956 Homo sapiens SAP domain-containing ribonucleoprotein Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 description 1
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 102100023361 SAP domain-containing ribonucleoprotein Human genes 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004543 anhydrous citric acid Drugs 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 108010037444 diisopropylglutathione ester Proteins 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000002742 neurokinin 1 receptor antagonist Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001144 powder X-ray diffraction data Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54132304P | 2004-02-02 | 2004-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605784B true ZA200605784B (en) | 2007-11-28 |
Family
ID=34837478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605784A ZA200605784B (en) | 2004-02-02 | 2006-07-13 | Process for preparation of 1-(2S,3S)-2-benzhydryl-N-(5-Tert-Butyl-2-methoxybenzyl)quinuclidin-3-amine |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20090099364A1 (de) |
| EP (1) | EP1713801B1 (de) |
| JP (1) | JP2007519710A (de) |
| KR (1) | KR100812046B1 (de) |
| CN (1) | CN1914202A (de) |
| AR (1) | AR047523A1 (de) |
| AT (1) | ATE380811T1 (de) |
| AU (1) | AU2005210259A1 (de) |
| BR (1) | BRPI0507334A (de) |
| CA (1) | CA2554360A1 (de) |
| CY (1) | CY1107141T1 (de) |
| DE (1) | DE602005003791T2 (de) |
| DK (1) | DK1713801T3 (de) |
| ES (1) | ES2296131T3 (de) |
| IL (1) | IL176817A0 (de) |
| NO (1) | NO20063268L (de) |
| PL (1) | PL1713801T3 (de) |
| PT (1) | PT1713801E (de) |
| RU (1) | RU2320659C9 (de) |
| SI (1) | SI1713801T1 (de) |
| WO (1) | WO2005075473A1 (de) |
| ZA (1) | ZA200605784B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101090735A (zh) | 2004-01-30 | 2007-12-19 | 辉瑞产品有限公司 | 用于使用液体剂型用β－环糊精制备多剂量制剂的抗菌防腐剂 |
| EP2571847B1 (de) | 2010-05-19 | 2016-09-21 | Sandoz AG | Verfahren zur herstellung chiraler hydrazide |
| WO2011144657A1 (en) | 2010-05-19 | 2011-11-24 | Sandoz Ag | Purification of posaconazole and posaconazole intermediates |
| RU2580318C2 (ru) | 2010-05-19 | 2016-04-10 | Сандоз Аг | Получение промежуточных продуктов для синтеза позаконазола |
| US9446029B2 (en) | 2010-07-27 | 2016-09-20 | Colorado State University Research Foundation | Use of NK-1 receptor antagonists in management of visceral pain |
| DE102011100534A1 (de) | 2011-05-05 | 2012-11-08 | Howaldtswerke-Deutsche Werft Gmbh | Verfahren zum Betreiben einer Reformer-Brennstoffzellenanlage |
| CN103635465A (zh) | 2011-06-16 | 2014-03-12 | 桑多斯股份公司 | 制备手性化合物的方法 |
| CN108341812A (zh) * | 2017-01-23 | 2018-07-31 | 科贝源(北京)生物医药科技有限公司 | 一种含奎宁环化合物的制备方法 |
| CN108341811A (zh) * | 2017-01-23 | 2018-07-31 | 科贝源(北京)生物医药科技有限公司 | 马罗皮坦杂质的制备方法 |
| CN106977512B (zh) * | 2017-05-04 | 2019-01-01 | 海门慧聚药业有限公司 | 制备马罗匹坦游离碱的方法 |
| CN110577522B (zh) * | 2018-06-07 | 2022-12-27 | 东莞市东阳光动物保健药品有限公司 | 马罗匹坦柠檬酸盐新晶型及其制备方法 |
| CN109320510B (zh) * | 2018-11-27 | 2021-04-27 | 江苏慧聚药业有限公司 | 一种马罗匹坦游离碱的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992021677A1 (en) | 1991-05-31 | 1992-12-10 | Pfizer Inc. | bibNUCLIDINE DERIVATIVES |
| US5393762A (en) * | 1993-06-04 | 1995-02-28 | Pfizer Inc. | Pharmaceutical agents for treatment of emesis |
| PE8798A1 (es) * | 1995-07-17 | 1998-03-02 | Pfizer | Procedimiento de separacion de los enantiomeros del 1-azabiciclo[2.2.2] octan-3-amina, 2-(difenilmetil) -n- [[2-metoxi-5-(1-metiletil) fenil] metil] |
| US6255320B1 (en) * | 1999-06-01 | 2001-07-03 | Pfizer Inc. | Polymorphs of a crystalline azo-bicyclo (2,2,2) octan-3-amine citrate and their pharmaceutical compositions |
| US6861526B2 (en) * | 2002-10-16 | 2005-03-01 | Pfizer Inc. | Process for the preparation of (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine |
-
2005
- 2005-01-26 US US10/588,049 patent/US20090099364A1/en not_active Abandoned
- 2005-01-26 ES ES05702373T patent/ES2296131T3/es active Active
- 2005-01-26 AU AU2005210259A patent/AU2005210259A1/en not_active Abandoned
- 2005-01-26 EP EP05702373A patent/EP1713801B1/de active Active
- 2005-01-26 BR BRPI0507334-0A patent/BRPI0507334A/pt not_active IP Right Cessation
- 2005-01-26 PL PL05702373T patent/PL1713801T3/pl unknown
- 2005-01-26 DK DK05702373T patent/DK1713801T3/da active
- 2005-01-26 AT AT05702373T patent/ATE380811T1/de not_active IP Right Cessation
- 2005-01-26 RU RU2006127969/04A patent/RU2320659C9/ru not_active IP Right Cessation
- 2005-01-26 DE DE602005003791T patent/DE602005003791T2/de not_active Expired - Fee Related
- 2005-01-26 PT PT05702373T patent/PT1713801E/pt unknown
- 2005-01-26 KR KR1020067015573A patent/KR100812046B1/ko not_active IP Right Cessation
- 2005-01-26 SI SI200530124T patent/SI1713801T1/sl unknown
- 2005-01-26 CN CNA2005800038987A patent/CN1914202A/zh active Pending
- 2005-01-26 JP JP2006550351A patent/JP2007519710A/ja not_active Withdrawn
- 2005-01-26 CA CA002554360A patent/CA2554360A1/en not_active Abandoned
- 2005-01-26 WO PCT/IB2005/000221 patent/WO2005075473A1/en active IP Right Grant
- 2005-01-31 AR ARP050100351A patent/AR047523A1/es not_active Application Discontinuation
-
2006
- 2006-07-12 IL IL176817A patent/IL176817A0/en unknown
- 2006-07-13 NO NO20063268A patent/NO20063268L/no not_active Application Discontinuation
- 2006-07-13 ZA ZA200605784A patent/ZA200605784B/en unknown
-
2008
- 2008-01-15 CY CY20081100055T patent/CY1107141T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20063268L (no) | 2006-08-15 |
| ES2296131T3 (es) | 2008-04-16 |
| EP1713801B1 (de) | 2007-12-12 |
| CY1107141T1 (el) | 2012-10-24 |
| US20090099364A1 (en) | 2009-04-16 |
| SI1713801T1 (sl) | 2008-04-30 |
| CA2554360A1 (en) | 2005-08-18 |
| RU2320659C1 (ru) | 2008-03-27 |
| KR20060127966A (ko) | 2006-12-13 |
| DE602005003791D1 (de) | 2008-01-24 |
| PL1713801T3 (pl) | 2008-04-30 |
| DE602005003791T2 (de) | 2008-05-29 |
| CN1914202A (zh) | 2007-02-14 |
| EP1713801A1 (de) | 2006-10-25 |
| RU2320659C9 (ru) | 2008-07-20 |
| AR047523A1 (es) | 2006-01-25 |
| JP2007519710A (ja) | 2007-07-19 |
| DK1713801T3 (da) | 2008-03-17 |
| AU2005210259A1 (en) | 2005-08-18 |
| BRPI0507334A (pt) | 2007-07-03 |
| PT1713801E (pt) | 2008-02-11 |
| WO2005075473A1 (en) | 2005-08-18 |
| IL176817A0 (en) | 2006-10-31 |
| ATE380811T1 (de) | 2007-12-15 |
| KR100812046B1 (ko) | 2008-03-10 |
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