CA1068708A - Produits de type 1,3-dihydrospiro (isobenzofurane-1,4'-piperidine)s et methodes pour leur preparation - Google Patents

Produits de type 1,3-dihydrospiro (isobenzofurane-1,4'-piperidine)s et methodes pour leur preparation

Info

Publication number: CA1068708A
Authority: CA; Canada
Prior art keywords: piperidine; isobenzofuran; dihydro; formula; carbon atoms
Prior art date: 1975-04-30
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

Application number

CA320,142A

Other languages

English (en)

Inventor

Victor J. Bauer

Solomon S. Klioze

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.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-04-30

Filing date

1979-01-23

Publication date

1979-12-25

1975-04-30 Priority claimed from US05/573,145 external-priority patent/US4024263A/en

1979-01-23 Application filed by Hoechst AG filed Critical Hoechst AG

1979-01-23 Priority to CA320,142A priority Critical patent/CA1068708A/fr

1979-12-25 Application granted granted Critical

1979-12-25 Publication of CA1068708A publication Critical patent/CA1068708A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 24
BYOIMOJOKVUNTP-UHFFFAOYSA-N spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C12=CC=CC=C2COC21CCNCC2 BYOIMOJOKVUNTP-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 11
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
229960000583 acetic acid Drugs 0.000 claims description 8
239000012362 glacial acetic acid Substances 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
XAEOQMBNJVPZDF-UHFFFAOYSA-N 1'-methyl-1'-oxido-1-phenylspiro[1h-2-benzofuran-3,4'-piperidin-1-ium] Chemical compound C1C[N+](C)([O-])CCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 XAEOQMBNJVPZDF-UHFFFAOYSA-N 0.000 claims description 2
CMGBHCCDZXPUIG-UHFFFAOYSA-N 1'-methyl-1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CN(C)CCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 CMGBHCCDZXPUIG-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229940099408 Oxidizing agent Drugs 0.000 claims 3
239000000126 substance Substances 0.000 claims 3
STABAPSYCQFWOK-UHFFFAOYSA-N 4-chlorobenzenecarboperoxoic acid Chemical group OOC(=O)C1=CC=C(Cl)C=C1 STABAPSYCQFWOK-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
229910052757 nitrogen Inorganic materials 0.000 description 24
239000000243 solution Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 15
229960001701 chloroform Drugs 0.000 description 15
239000007787 solid Substances 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
-1 nitroso, amino Chemical group 0.000 description 6
125000003003 spiro group Chemical group 0.000 description 6
239000003208 petroleum Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000001665 trituration Methods 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
ZFJQWOMHWFYLPD-UHFFFAOYSA-N 1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CNCCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 ZFJQWOMHWFYLPD-UHFFFAOYSA-N 0.000 description 2
ZQBMIDLBCFJEFK-UHFFFAOYSA-N 1-phenylspiro[1h-2-benzofuran-3,4'-piperidine]-1'-amine Chemical compound C1CN(N)CCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 ZQBMIDLBCFJEFK-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229960003328 benzoyl peroxide Drugs 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
150000002832 nitroso derivatives Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
GKMAQGUYMXDMSK-UHFFFAOYSA-N (1-phenylspiro[1h-2-benzofuran-3,4'-piperidine]-1'-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)ON(CC1)CCC1(C1=CC=CC=C11)OC1C1=CC=CC=C1 GKMAQGUYMXDMSK-UHFFFAOYSA-N 0.000 description 1
FXPSDKQKMFMACP-UHFFFAOYSA-N 1'-benzyl-1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C=1C=CC=CC=1CN(CC1)CCC1(C1=CC=CC=C11)OC1C1=CC=CC=C1 FXPSDKQKMFMACP-UHFFFAOYSA-N 0.000 description 1
YLLSCHUCIDOSDK-UHFFFAOYSA-N 1'-hydroxy-1-(4-methoxyphenyl)spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1=CC(OC)=CC=C1C1C2=CC=CC=C2C2(CCN(O)CC2)O1 YLLSCHUCIDOSDK-UHFFFAOYSA-N 0.000 description 1
NNJRHUFLMMOXCG-UHFFFAOYSA-N 1'-nitroso-1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CN(N=O)CCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 NNJRHUFLMMOXCG-UHFFFAOYSA-N 0.000 description 1
ORJPAXGWPZSLLO-UHFFFAOYSA-N 1'-oxido-1-phenyl-1'-(2-phenylethyl)spiro[1h-2-benzofuran-3,4'-piperidin-1-ium] Chemical compound C1CC2(C3=CC=CC=C3C(O2)C=2C=CC=CC=2)CC[N+]1([O-])CCC1=CC=CC=C1 ORJPAXGWPZSLLO-UHFFFAOYSA-N 0.000 description 1
JFWWJFRTGUIZEA-UHFFFAOYSA-N 1-(4-fluorophenyl)spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1=CC(F)=CC=C1C1C2=CC=CC=C2C2(CCNCC2)O1 JFWWJFRTGUIZEA-UHFFFAOYSA-N 0.000 description 1
MZPRTWARTUFADN-UHFFFAOYSA-N 1-phenyl-n-propan-2-ylspiro[1h-2-benzofuran-3,4'-piperidine]-1'-amine Chemical compound C1CN(NC(C)C)CCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 MZPRTWARTUFADN-UHFFFAOYSA-N 0.000 description 1
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
QWCRXNXWCCUESX-UHFFFAOYSA-N 5-methoxy-1-(4-methoxyphenyl)-n-pentylspiro[1h-2-benzofuran-3,4'-piperidine]-1'-amine Chemical compound C1CN(NCCCCC)CCC21C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)O2 QWCRXNXWCCUESX-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
229940123150 Chelating agent Drugs 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
NMDZYGISUDHTDN-UHFFFAOYSA-N [1-(4-methoxyphenyl)spiro[1h-2-benzofuran-3,4'-piperidine]-1'-yl] benzoate Chemical compound C1=CC(OC)=CC=C1C1C2=CC=CC=C2C2(CCN(CC2)OC(=O)C=2C=CC=CC=2)O1 NMDZYGISUDHTDN-UHFFFAOYSA-N 0.000 description 1
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125000003282 alkyl amino group Chemical group 0.000 description 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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229910052725 zinc Inorganic materials 0.000 description 1

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Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA320,142A 1975-04-30 1979-01-23 Produits de type 1,3-dihydrospiro (isobenzofurane-1,4'-piperidine)s et methodes pour leur preparation Expired CA1068708A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA320,142A CA1068708A (fr)	1975-04-30	1979-01-23	Produits de type 1,3-dihydrospiro (isobenzofurane-1,4'-piperidine)s et methodes pour leur preparation

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US05/573,145 US4024263A (en)	1975-04-30	1975-04-30	1,3-Dihydrospiro[isobenzofuran-1,4'-piperidine]s
CA251,487A CA1067081A (fr)	1975-04-30	1976-04-29	Preparation de 1,3-dihydrospiro (isobenzofuran-1,4'-piperidine) s
CA320,142A CA1068708A (fr)	1975-04-30	1979-01-23	Produits de type 1,3-dihydrospiro (isobenzofurane-1,4'-piperidine)s et methodes pour leur preparation

Publications (1)

Publication Number	Publication Date
CA1068708A true CA1068708A (fr)	1979-12-25

Family

ID=27164447

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA320,142A Expired CA1068708A (fr)	1975-04-30	1979-01-23	Produits de type 1,3-dihydrospiro (isobenzofurane-1,4'-piperidine)s et methodes pour leur preparation

Country Status (1)

Country	Link
CA (1)	CA1068708A (fr)

1979
- 1979-01-23 CA CA320,142A patent/CA1068708A/fr not_active Expired

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