PL197306B1 - Nowe pochodne 4-[2-(3,4-dimetoksybenzoilo)allilo]piperydyny - Google Patents

Nowe pochodne 4-[2-(3,4-dimetoksybenzoilo)allilo]piperydyny

Info

Publication number: PL197306B1
Authority: PL; Poland
Prior art keywords: compound; formula; alkyl; reaction; dimethoxy
Prior art date: 1995-12-15

Application number

PL327512A

Other languages

English (en)

Polish (pl)

Other versions

PL327512A1 (en

Inventor

Keith M. Devries

Original Assignee

Pfizer

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.)

1995-12-15

Filing date

1996-10-11

Publication date

2008-03-31

1996-10-11 Application filed by Pfizer filed Critical Pfizer

1998-12-21 Publication of PL327512A1 publication Critical patent/PL327512A1/xx

2008-03-31 Publication of PL197306B1 publication Critical patent/PL197306B1/pl

Links

150000001875 compounds Chemical class 0.000 title abstract description 50
238000000034 method Methods 0.000 title description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical class CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 title 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
-1 benzyl halide Chemical class 0.000 claims abstract description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
150000003053 piperidines Chemical class 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 abstract description 6
239000000543 intermediate Substances 0.000 abstract description 6
239000002253 acid Substances 0.000 abstract description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
125000001475 halogen functional group Chemical group 0.000 abstract 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
125000001424 substituent group Chemical group 0.000 abstract 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
238000004128 high performance liquid chromatography Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 7
IHMQOBPGHZFGLC-UHFFFAOYSA-N 5,6-dimethoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)CC2 IHMQOBPGHZFGLC-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
208000024827 Alzheimer disease Diseases 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010039966 Senile dementia Diseases 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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 3
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
PGBZORAISITZTF-UHFFFAOYSA-N Donepezil metabolite M4 Chemical class O=C1C=2C=C(OC)C(OC)=CC=2CC1CC1CCNCC1 PGBZORAISITZTF-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
208000026106 cerebrovascular disease Diseases 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WBGBLGWWFQCJAI-UHFFFAOYSA-N 1-(methylsulfanylmethyl)piperidine Chemical compound CSCN1CCCCC1 WBGBLGWWFQCJAI-UHFFFAOYSA-N 0.000 description 1
VFYIKWMHUOXSDY-UHFFFAOYSA-N 3-(1-methoxycarbonylpiperidin-4-yl)propanoic acid Chemical compound COC(=O)N1CCC(CCC(O)=O)CC1 VFYIKWMHUOXSDY-UHFFFAOYSA-N 0.000 description 1
AUYQMCCWFNSFGV-UHFFFAOYSA-N 3-piperidin-1-ium-4-ylpropanoate Chemical compound OC(=O)CCC1CCNCC1 AUYQMCCWFNSFGV-UHFFFAOYSA-N 0.000 description 1
TWBKFRCIBBFNED-UHFFFAOYSA-N 4-(3-chloro-3-oxopropyl)piperidine-1-carboxylic acid Chemical compound ClC(=O)CCC1CCN(CC1)C(=O)O TWBKFRCIBBFNED-UHFFFAOYSA-N 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
206010008111 Cerebral haemorrhage Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
201000011240 Frontotemporal dementia Diseases 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
208000026139 Memory disease Diseases 0.000 description 1
206010033864 Paranoia Diseases 0.000 description 1
208000027099 Paranoid disease Diseases 0.000 description 1
208000000609 Pick Disease of the Brain Diseases 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
206010043118 Tardive Dyskinesia Diseases 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-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
150000007513 acids Chemical class 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
206010008118 cerebral infarction Diseases 0.000 description 1
206010008129 cerebral palsy Diseases 0.000 description 1
238000000451 chemical ionisation Methods 0.000 description 1
239000000544 cholinesterase inhibitor Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
206010014599 encephalitis Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000036252 glycation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000003400 hallucinatory effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WRZOOPVTTSTZQW-UHFFFAOYSA-N methyl 4-[(5,6-dimethoxy-3-oxo-1,2-dihydroinden-2-yl)methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1CC1C(=O)C2=CC(OC)=C(OC)C=C2C1 WRZOOPVTTSTZQW-UHFFFAOYSA-N 0.000 description 1
CVYYGOUULIWMMC-UHFFFAOYSA-N methyl 4-[3-(3,4-dimethoxyphenyl)-3-oxopropyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1CCC(=O)C1=CC=C(OC)C(OC)=C1 CVYYGOUULIWMMC-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000002245 particle Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
239000012066 reaction slurry Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
208000027765 speech disease Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
UKKLUBWWAGMMAG-UHFFFAOYSA-N tris(2-hydroxyethyl)azanium;bromide Chemical compound Br.OCCN(CCO)CCO UKKLUBWWAGMMAG-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

PL327512A 1995-12-15 1996-10-11 Nowe pochodne 4-[2-(3,4-dimetoksybenzoilo)allilo]piperydyny PL197306B1 (pl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US875395P	1995-12-15	1995-12-15
PCT/IB1996/001076 WO1997022584A1 (fr)	1995-12-15	1996-10-11	Procedes de preparation de 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine et intermediaires utilises a cet effet

Publications (2)

Publication Number	Publication Date
PL327512A1 PL327512A1 (en)	1998-12-21
PL197306B1 true PL197306B1 (pl)	2008-03-31

Family

ID=21733469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL327512A PL197306B1 (pl)	1995-12-15	1996-10-11	Nowe pochodne 4-[2-(3,4-dimetoksybenzoilo)allilo]piperydyny

Country Status (33)

Country	Link
EP (1)	EP0883607A1 (fr)
JP (1)	JP3066083B2 (fr)
KR (1)	KR20000064387A (fr)
AP (1)	AP708A (fr)
AR (1)	AR004368A1 (fr)
AU (1)	AU716462B2 (fr)
BG (1)	BG102525A (fr)
BR (1)	BR9612018A (fr)
CA (1)	CA2237647A1 (fr)
CO (1)	CO4750831A1 (fr)
CZ (1)	CZ180898A3 (fr)
DZ (1)	DZ2141A1 (fr)
GT (1)	GT199600092A (fr)
HN (1)	HN1996000065A (fr)
HR (1)	HRP960592A2 (fr)
HU (1)	HUP9904275A3 (fr)
IL (3)	IL136421A0 (fr)
IS (1)	IS4752A (fr)
MA (1)	MA24032A1 (fr)
NO (1)	NO982712L (fr)
NZ (1)	NZ318843A (fr)
OA (1)	OA10694A (fr)
PE (1)	PE25698A1 (fr)
PL (1)	PL197306B1 (fr)
RO (1)	RO121382B1 (fr)
RU (1)	RU2160731C2 (fr)
SK (1)	SK75498A3 (fr)
TN (1)	TNSN96153A1 (fr)
TW (1)	TW414787B (fr)
UY (1)	UY24401A1 (fr)
WO (1)	WO1997022584A1 (fr)
YU (1)	YU49486B (fr)
ZA (1)	ZA9610533B (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE292116T1 (de)	1998-01-16	2005-04-15	Eisai Co Ltd	Verfahren zur herstellung von donepezilderivaten
IL125809A (en)	1998-08-17	2005-08-31	Finetech Lab Ltd	Process and intermediates for production of donepezil and related compounds
US7148354B2 (en) *	2002-07-24	2006-12-12	Dr. Reddy's Laboratories Limited	Process for preparation of donepezil
IL150982A (en)	2002-07-30	2007-02-11	Ori Lerman	Process for making Donafzil
IL151253A0 (en) *	2002-08-14	2003-04-10	Finetech Lab Ltd	Process for production of highly pure donepezil hydrochloride
US6649765B1 (en)	2003-02-12	2003-11-18	Usv Limited, Bsd Marg.	Process for the preparation of 1-benzyl-4(5,6-dimethoxy-1-indanon)-2-yl) methyl piperidine hydrochloride (Donepezil HCL)
US6953856B2 (en)	2003-02-12	2005-10-11	Usv, Limited	Process for the preparation of 1-benzyl-4-(5,6-dimethoxy-1-indanon)-2-yl) methyl piperidine hydrochloride (Donepezil HCI)
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1996
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- 1996-10-11 EP EP96931937A patent/EP0883607A1/fr not_active Withdrawn
- 1996-10-11 AU AU70925/96A patent/AU716462B2/en not_active Ceased
- 1996-10-11 IL IL13642196A patent/IL136421A0/xx unknown
- 1996-10-11 WO PCT/IB1996/001076 patent/WO1997022584A1/fr not_active Ceased
- 1996-10-11 PL PL327512A patent/PL197306B1/pl not_active IP Right Cessation
- 1996-10-11 CA CA002237647A patent/CA2237647A1/fr not_active Abandoned
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- 1996-10-11 JP JP9522607A patent/JP3066083B2/ja not_active Expired - Lifetime
- 1996-10-11 BR BR9612018A patent/BR9612018A/pt not_active Application Discontinuation
- 1996-10-11 KR KR1019980704423A patent/KR20000064387A/ko not_active Ceased
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- 1996-12-11 DZ DZ960186A patent/DZ2141A1/fr active
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1998
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Also Published As

Publication number	Publication date
AU7092596A (en)	1997-07-14
IL136421A0 (en)	2001-06-14
MX9804820A (es)	1998-10-31
NZ318843A (en)	2000-01-28
EP0883607A1 (fr)	1998-12-16
AP708A (en)	1998-12-04
OA10694A (en)	2001-05-04
NO982712D0 (no)	1998-06-12
JP3066083B2 (ja)	2000-07-17
CA2237647A1 (fr)	1997-06-26
HRP960592A2 (en)	1998-06-30
HUP9904275A2 (hu)	2000-05-28
PE25698A1 (es)	1998-05-21
IL124452A0 (en)	1998-12-06
CO4750831A1 (es)	1999-03-31
NO982712L (no)	1998-06-12
KR20000064387A (ko)	2000-11-06
MA24032A1 (fr)	1997-07-01
HN1996000065A (es)	1997-06-26
YU66096A (en)	1999-11-22
ZA9610533B (en)	1998-06-15
AP9600892A0 (en)	1997-01-31
PL327512A1 (en)	1998-12-21
AR004368A1 (es)	1998-11-04
BG102525A (en)	1999-05-31
IL136420A0 (en)	2001-06-14
BR9612018A (pt)	1999-02-17
WO1997022584A1 (fr)	1997-06-26
HUP9904275A3 (en)	2001-05-28
CZ180898A3 (cs)	1999-05-12
JPH11500756A (ja)	1999-01-19
AU716462B2 (en)	2000-02-24
RU2160731C2 (ru)	2000-12-20
UY24401A1 (es)	1997-06-09
GT199600092A (es)	1998-05-12
IS4752A (is)	1998-05-22
TW414787B (en)	2000-12-11
DZ2141A1 (fr)	2002-07-23
RO121382B1 (ro)	2007-04-30
YU49486B (sh)	2006-08-17
TNSN96153A1 (fr)	2005-03-15
SK75498A3 (en)	1999-08-06

Legal Events

Date	Code	Title	Description
2009-12-31	LAPS	Decisions on the lapse of the protection rights	Effective date: 20081011

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