CA2555035C - Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)phenoxy]ethyl}pyrrolidine - Google Patents

Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)phenoxy]ethyl}pyrrolidine Download PDF

Info

Publication number: CA2555035C
Authority: CA; Canada
Prior art keywords: phenyl; methoxy; ethyl; benzyloxy; bromo
Prior art date: 1999-05-24
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA002555035A

Other languages

English (en)

Other versions

CA2555035A1 (fr

Inventor

Charles Kwok-Fung Chiu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Pfizer Products Inc

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.)

1999-05-24

Filing date

2000-05-19

Publication date

2009-06-09

2000-05-19 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2000-05-19 Priority claimed from CA002308922A external-priority patent/CA2308922C/fr

2000-11-24 Publication of CA2555035A1 publication Critical patent/CA2555035A1/fr

2009-06-09 Application granted granted Critical

2009-06-09 Publication of CA2555035C publication Critical patent/CA2555035C/fr

2020-05-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 9
NAPIZYZVKMASNP-PXJZQJOASA-N 1-[2-[4-[(1r,2s)-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenoxy]ethyl]pyrrolidine Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)OC)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 NAPIZYZVKMASNP-PXJZQJOASA-N 0.000 title abstract description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 11
-1 4-(4-benzyloxy-phenyl)-7-methoxy-phenyl-1,2-dihydro-naphthalene Chemical compound 0.000 claims description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
GXAWUBYOPVAHKZ-UHFFFAOYSA-N 7-methoxy-3-phenyl-4-(4-phenylmethoxyphenyl)-1,2-dihydronaphthalene Chemical compound C1CC2=CC(OC)=CC=C2C(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1C1=CC=CC=C1 GXAWUBYOPVAHKZ-UHFFFAOYSA-N 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
YMAFPDBITYFGPO-UHFFFAOYSA-N 3-(2-bromo-5-methoxyphenyl)-1-phenylpropan-1-one Chemical compound COC1=CC=C(Br)C(CCC(=O)C=2C=CC=CC=2)=C1 YMAFPDBITYFGPO-UHFFFAOYSA-N 0.000 claims description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 7
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 7
WQRDHSBFQYMBGZ-UHFFFAOYSA-N 3-[5-methoxy-2-(4-phenylmethoxybenzoyl)phenyl]-1-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC(OC)=CC=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 WQRDHSBFQYMBGZ-UHFFFAOYSA-N 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims description 5
MURVUTUZSUEIGI-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(Br)C(CBr)=C1 MURVUTUZSUEIGI-UHFFFAOYSA-N 0.000 claims description 4
BLZNSXFQRKVFRP-UHFFFAOYSA-N 1-bromo-4-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Br)C(C)=C1 BLZNSXFQRKVFRP-UHFFFAOYSA-N 0.000 claims description 4
UDAOJHAASAWVIQ-UHFFFAOYSA-N 4-phenylmethoxybenzonitrile Chemical compound C1=CC(C#N)=CC=C1OCC1=CC=CC=C1 UDAOJHAASAWVIQ-UHFFFAOYSA-N 0.000 claims description 4
238000006114 decarboxylation reaction Methods 0.000 claims description 4
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims description 4
NAPIZYZVKMASNP-UHFFFAOYSA-N 1-[2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]ethyl]pyrrolidine Chemical compound C1CC2=CC(OC)=CC=C2C(C=2C=CC(OCCN3CCCC3)=CC=2)C1C1=CC=CC=C1 NAPIZYZVKMASNP-UHFFFAOYSA-N 0.000 claims description 2
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 claims description 2
229910001115 Zinc-copper couple Inorganic materials 0.000 claims description 2
XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 5
208000001132 Osteoporosis Diseases 0.000 abstract description 2
GXESHMAMLJKROZ-IAPPQJPRSA-N lasofoxifene Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 GXESHMAMLJKROZ-IAPPQJPRSA-N 0.000 abstract description 2
239000000243 solution Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000000047 product Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
150000001204 N-oxides Chemical class 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
101100272976 Panax ginseng CYP716A53v2 gene Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910007565 Zn—Cu Inorganic materials 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000001076 estrogenic effect Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
CZOYXKZXMKSRQD-UHFFFAOYSA-N 2-[2-(2-bromo-5-methoxyphenyl)ethyl]-2-phenyl-1,3-dioxolane Chemical compound COC1=CC=C(Br)C(CCC2(OCCO2)C=2C=CC=CC=2)=C1 CZOYXKZXMKSRQD-UHFFFAOYSA-N 0.000 description 2
KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 description 2
229910010062 TiCl3 Inorganic materials 0.000 description 2
SIMZFBKLJVJWHL-UHFFFAOYSA-N [4-methoxy-2-[2-(2-phenyl-1,3-dioxolan-2-yl)ethyl]phenyl]-(4-phenylmethoxyphenyl)methanone Chemical compound O1CCOC1(C=1C=CC=CC=1)CCC1=CC(OC)=CC=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 SIMZFBKLJVJWHL-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000003509 anti-fertility effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
229940011871 estrogen Drugs 0.000 description 2
239000000262 estrogen Substances 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
230000000871 hypocholesterolemic effect Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 description 1
GJPUJYUDFUYBLU-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)-4-methoxybenzene;bromomethylbenzene Chemical compound BrCC1=CC=CC=C1.COC1=CC=C(Br)C(CBr)=C1 GJPUJYUDFUYBLU-UHFFFAOYSA-N 0.000 description 1
MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
GMOYUTKNPLBTMT-UHFFFAOYSA-N 2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 GMOYUTKNPLBTMT-UHFFFAOYSA-N 0.000 description 1
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
JEYWNNAZDLFBFF-UHFFFAOYSA-N Nafoxidine Chemical compound C1CC2=CC(OC)=CC=C2C(C=2C=CC(OCCN3CCCC3)=CC=2)=C1C1=CC=CC=C1 JEYWNNAZDLFBFF-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000006241 alcohol protecting group Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
150000005840 aryl radicals Chemical group 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
239000012267 brine Substances 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229950002366 nafoxidine Drugs 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA002555035A 1999-05-24 2000-05-19 Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)phenoxy]ethyl}pyrrolidine Expired - Lifetime CA2555035C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US13557899P	1999-05-24	1999-05-24
US60/135,578		1999-05-24
CA002308922A CA2308922C (fr)	1999-05-24	2000-05-19	Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)pheno xy!ethyl}pyrrolidine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002308922A Division CA2308922C (fr)	1999-05-24	2000-05-19	Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)pheno xy!ethyl}pyrrolidine

Publications (2)

Publication Number	Publication Date
CA2555035A1 CA2555035A1 (fr)	2000-11-24
CA2555035C true CA2555035C (fr)	2009-06-09

Family

ID=37055157

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA002555035A Expired - Lifetime CA2555035C (fr)	1999-05-24	2000-05-19	Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)phenoxy]ethyl}pyrrolidine
CA002555051A Expired - Lifetime CA2555051C (fr)	1999-05-24	2000-05-19	Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)pheno xy!ethyl}pyrrolidine

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA002555051A Expired - Lifetime CA2555051C (fr)	1999-05-24	2000-05-19	Synthese de cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphtalen-1-yl)pheno xy!ethyl}pyrrolidine

Country Status (1)

Country	Link
CA (2)	CA2555035C (fr)

2000
- 2000-05-19 CA CA002555035A patent/CA2555035C/fr not_active Expired - Lifetime
- 2000-05-19 CA CA002555051A patent/CA2555051C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2555035A1 (fr)	2000-11-24
CA2555051A1 (fr)	2000-11-24
CA2555051C (fr)	2007-09-11

Legal Events

Date	Code	Title	Description
2006-08-21	EEER	Examination request
2020-07-21	MKEX	Expiry	Effective date: 20200519

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