CA1050986A - Composes d'isoquinoline - Google Patents

Composes d'isoquinoline

Info

Publication number: CA1050986A
Authority: CA; Canada
Prior art keywords: tetrahydro; isoquinoline; propoxy; hydroxy; methoxy
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

CA241,417A

Other languages

English (en)

Inventor

Manfred Raschack

Dirk Wuppermann

Frank Zimmermann

Albert Westermann

Ludwig Friedrich

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.)

Abbott GmbH and Co KG

Original Assignee

Knoll GmbH

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

1975-12-10

Publication date

1979-03-20

1975-12-10 Application filed by Knoll GmbH filed Critical Knoll GmbH

1979-03-20 Application granted granted Critical

1979-03-20 Publication of CA1050986A publication Critical patent/CA1050986A/fr

Status Expired legal-status Critical Current

Links

125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 56
150000001875 compounds Chemical class 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract 3
239000000126 substance Substances 0.000 claims description 33
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 15
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 12
-1 isoquinoline compound Chemical class 0.000 claims description 10
AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
DVRXCMRXLKMMSL-UHFFFAOYSA-N 1-[6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=CC(OCC(O)CNC(C)C)=CC=C21 DVRXCMRXLKMMSL-UHFFFAOYSA-N 0.000 claims description 3
AJLVCVJPQIDMLV-UHFFFAOYSA-N 5-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=C1C=CC=C2OCC(O)CNC(C)C AJLVCVJPQIDMLV-UHFFFAOYSA-N 0.000 claims description 3
AVNBXHHPSLIAFU-UHFFFAOYSA-N 6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-7-methoxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)C)=C2 AVNBXHHPSLIAFU-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
150000002537 isoquinolines Chemical class 0.000 claims description 3
SBJSXRGEXNGDCA-UHFFFAOYSA-N 1-[6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C=1C=C2CN(C(=O)C)CCC2=CC=1OCC1CO1 SBJSXRGEXNGDCA-UHFFFAOYSA-N 0.000 claims description 2
NMNMMLVRTDWRHH-UHFFFAOYSA-N 1-[6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound CC1N(C(C)=O)CCC2=CC(OCC(O)CNC(C)C)=CC=C21 NMNMMLVRTDWRHH-UHFFFAOYSA-N 0.000 claims description 2
FEQWTAZFEOTUKZ-UHFFFAOYSA-N 1-[7-methoxy-8-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound COC1=CC=C2CCN(C(C)=O)CC2=C1OCC1CO1 FEQWTAZFEOTUKZ-UHFFFAOYSA-N 0.000 claims description 2
FHKXBLWFZZQMER-UHFFFAOYSA-N 6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C=1C=C2CN(C=O)CCC2=CC=1OCC1CO1 FHKXBLWFZZQMER-UHFFFAOYSA-N 0.000 claims description 2
ZSOPVLDSQNKSIB-UHFFFAOYSA-N 7-methoxy-1-methyl-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound COC1=CC=2C(C)N(C=O)CCC=2C=C1OCC1CO1 ZSOPVLDSQNKSIB-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
NAXTXOKAQGHJFA-UHFFFAOYSA-N 1-[5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1=CC=C(OCC(O)CNC(C)(C)C)C2=C1CN(C(=O)C)CC2 NAXTXOKAQGHJFA-UHFFFAOYSA-N 0.000 claims 2
RTCHUYAJCIJOIH-UHFFFAOYSA-N 1-[5-[3-(tert-butylamino)-2-hydroxypropoxy]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=C(OCC(O)CNC(C)(C)C)C(OC)=CC=C21 RTCHUYAJCIJOIH-UHFFFAOYSA-N 0.000 claims 2
DYJWGBLOWUSKCN-UHFFFAOYSA-N 1-[6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]propan-1-one Chemical compound CC(C)NCC(O)COC1=C(OC)C=C2CN(C(=O)CC)CCC2=C1 DYJWGBLOWUSKCN-UHFFFAOYSA-N 0.000 claims 2
LCSJKMNBFMONQB-UHFFFAOYSA-N 1-[6-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound CC(C)(C)NCC(O)COC1=CC=C2CN(C(=O)C)CCC2=C1 LCSJKMNBFMONQB-UHFFFAOYSA-N 0.000 claims 2
FNDFUHMQAHEIAM-UHFFFAOYSA-N 1-[6-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methoxy-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound CC1N(C(C)=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)(C)C)=C2 FNDFUHMQAHEIAM-UHFFFAOYSA-N 0.000 claims 2
HUWVAOSRLWAYTO-UHFFFAOYSA-N 1-[7-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1=C(OCC(O)CNC(C)(C)C)C=C2CN(C(=O)C)CCC2=C1 HUWVAOSRLWAYTO-UHFFFAOYSA-N 0.000 claims 2
FGOJJBOEGJEZFI-UHFFFAOYSA-N 1-[7-methoxy-1-methyl-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound COC1=CC=2C(C)N(C(C)=O)CCC=2C=C1OCC1CO1 FGOJJBOEGJEZFI-UHFFFAOYSA-N 0.000 claims 2
WAJJRRYXWISHGP-UHFFFAOYSA-N 1-[7-methoxy-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound COC1=CC=2CN(C(C)=O)CCC=2C=C1OCC1CO1 WAJJRRYXWISHGP-UHFFFAOYSA-N 0.000 claims 2
ZTSYBAFKRSQLAY-UHFFFAOYSA-N 1-[7-methoxy-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]propan-1-one Chemical compound COC=1C=C2CN(C(=O)CC)CCC2=CC=1OCC1CO1 ZTSYBAFKRSQLAY-UHFFFAOYSA-N 0.000 claims 2
DMGALLXUWXRUOM-UHFFFAOYSA-N 1-[8-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1CN(C(C)=O)CC2=C(OCC(O)CNC(C)(C)C)C(OC)=CC=C21 DMGALLXUWXRUOM-UHFFFAOYSA-N 0.000 claims 2
BDUNUNCKIPQCGF-UHFFFAOYSA-N 5-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=C1C=CC=C2OCC1CO1 BDUNUNCKIPQCGF-UHFFFAOYSA-N 0.000 claims 2
FRZFHNKLXIMBRF-UHFFFAOYSA-N 5-[3-(tert-butylamino)-2-hydroxypropoxy]-6-methoxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=C(OCC(O)CNC(C)(C)C)C(OC)=CC=C21 FRZFHNKLXIMBRF-UHFFFAOYSA-N 0.000 claims 2
CFVQRDGDSMXDOR-UHFFFAOYSA-N 6-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=CC(OCC(O)CNC(C)(C)C)=CC=C21 CFVQRDGDSMXDOR-UHFFFAOYSA-N 0.000 claims 2
QVLMMAMWNXYOSY-UHFFFAOYSA-N 6-methoxy-5-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound COC1=CC=C2CN(C=O)CCC2=C1OCC1CO1 QVLMMAMWNXYOSY-UHFFFAOYSA-N 0.000 claims 2
GMJHUSJLZXFFQJ-UHFFFAOYSA-N soquinolol Chemical compound C1N(C=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C GMJHUSJLZXFFQJ-UHFFFAOYSA-N 0.000 claims 2
HBAFZSBUICTQGD-UHFFFAOYSA-N 1-[1-methyl-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C=1C=C2C(C)N(C(C)=O)CCC2=CC=1OCC1CO1 HBAFZSBUICTQGD-UHFFFAOYSA-N 0.000 claims 1
KHEBTZWXZFCWRU-UHFFFAOYSA-N 1-[5-(3-amino-2-hydroxy-4-methylpentoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=C1C=CC=C2OCC(O)C(N)C(C)C KHEBTZWXZFCWRU-UHFFFAOYSA-N 0.000 claims 1
HJGVZPVRLJMHLZ-UHFFFAOYSA-N 1-[5-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(=O)C)CCC2=C1C=CC=C2OCC1CO1 HJGVZPVRLJMHLZ-UHFFFAOYSA-N 0.000 claims 1
UWIYVDARIRFERZ-UHFFFAOYSA-N 1-[5-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=C1C=CC=C2OCC(O)CNC(C)C UWIYVDARIRFERZ-UHFFFAOYSA-N 0.000 claims 1
BMVPUDSSHJZURY-UHFFFAOYSA-N 1-[6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)C)=C2 BMVPUDSSHJZURY-UHFFFAOYSA-N 0.000 claims 1
XQUUMEVHTHUXGO-UHFFFAOYSA-N 1-[6-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)(C)C)=C2 XQUUMEVHTHUXGO-UHFFFAOYSA-N 0.000 claims 1
KXNSHTRGCHCJHF-UHFFFAOYSA-N 1-[6-methoxy-5-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound COC1=CC=C2CN(C(C)=O)CCC2=C1OCC1CO1 KXNSHTRGCHCJHF-UHFFFAOYSA-N 0.000 claims 1
QAQVBIZWNSHRCJ-UHFFFAOYSA-N 1-[7-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C)CCC2=CC=C1OCC1CO1 QAQVBIZWNSHRCJ-UHFFFAOYSA-N 0.000 claims 1
JKEQHZZKYMHIHP-UHFFFAOYSA-N 5-[2-hydroxy-3-(propan-2-ylamino)propoxy]-6-methoxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=C(OCC(O)CNC(C)C)C(OC)=CC=C21 JKEQHZZKYMHIHP-UHFFFAOYSA-N 0.000 claims 1
KFDZREAPSAUXNE-UHFFFAOYSA-N 6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=CC(OCC(O)CNC(C)C)=CC=C21 KFDZREAPSAUXNE-UHFFFAOYSA-N 0.000 claims 1
VNXLVPSZXFPODM-UHFFFAOYSA-N 6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-7-methoxy-1-methyl-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound CC1N(C=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)C)=C2 VNXLVPSZXFPODM-UHFFFAOYSA-N 0.000 claims 1
LZKWUQAZPICEGC-UHFFFAOYSA-N 6-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methoxy-1-methyl-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound CC1N(C=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)(C)C)=C2 LZKWUQAZPICEGC-UHFFFAOYSA-N 0.000 claims 1
LFJMSMXUOMXUMK-UHFFFAOYSA-N 6-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methoxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=C1C=C(OC)C(OCC(O)CNC(C)(C)C)=C2 LFJMSMXUOMXUMK-UHFFFAOYSA-N 0.000 claims 1
AXWNTORKYNWNRD-UHFFFAOYSA-N 7-methoxy-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound COC1=CC=2CN(C=O)CCC=2C=C1OCC1CO1 AXWNTORKYNWNRD-UHFFFAOYSA-N 0.000 claims 1
XIMLCIZPDHAENW-UHFFFAOYSA-N 8-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methoxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1CN(C=O)CC2=C(OCC(O)CNC(C)(C)C)C(OC)=CC=C21 XIMLCIZPDHAENW-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 4
230000000903 blocking effect Effects 0.000 abstract description 3
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 13
229940073584 methylene chloride Drugs 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 7
238000009835 boiling Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
210000004204 blood vessel Anatomy 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229940093499 ethyl acetate Drugs 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940099112 cornstarch Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
USVPGYXADKFDAI-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-6-ol;hydrobromide Chemical compound Br.C1NCCC2=CC(O)=CC=C21 USVPGYXADKFDAI-UHFFFAOYSA-N 0.000 description 2
YMOUCXCQZXIWHR-UHFFFAOYSA-N 6-methoxy-5-phenylmethoxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound COC1=CC=C2CN(C=O)CCC2=C1OCC1=CC=CC=C1 YMOUCXCQZXIWHR-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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 2
241001465754 Metazoa Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 2
238000011835 investigation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229960001375 lactose Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000009923 sugaring Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
231100000816 toxic dose Toxicity 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
OETVYRJDJWKUNX-UHFFFAOYSA-N 1-(6-hydroxy-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound OC1=CC=C2C(C)N(C(C)=O)CCC2=C1 OETVYRJDJWKUNX-UHFFFAOYSA-N 0.000 description 1
KXTIMMJONYFHCM-UHFFFAOYSA-N 1-(6-hydroxy-3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound OC1=CC=C2CN(C(=O)C)CCC2=C1 KXTIMMJONYFHCM-UHFFFAOYSA-N 0.000 description 1
KXROHCCJTQGRAG-UHFFFAOYSA-N 1-(6-hydroxy-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl)propan-1-one Chemical compound OC1=C(OC)C=C2CN(C(=O)CC)CCC2=C1 KXROHCCJTQGRAG-UHFFFAOYSA-N 0.000 description 1
AFWHVAFMAIDVTH-UHFFFAOYSA-N 1-methoxyisoquinoline Chemical compound C1=CC=C2C(OC)=NC=CC2=C1 AFWHVAFMAIDVTH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
VHKOSSFXJPIOLB-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1N(C=O)CCC2=CC(O)=CC=C21 VHKOSSFXJPIOLB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010058177 Hyperkinetic heart syndrome Diseases 0.000 description 1
206010020852 Hypertonia Diseases 0.000 description 1
241000820057 Ithone Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
206010033557 Palpitations Diseases 0.000 description 1
241001163743 Perlodes Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
241001385887 Tachys Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
FYUWIEKAVLOHSE-UHFFFAOYSA-N ethenyl acetate;1-ethenylpyrrolidin-2-one Chemical compound CC(=O)OC=C.C=CN1CCCC1=O FYUWIEKAVLOHSE-UHFFFAOYSA-N 0.000 description 1
HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
230000004907 flux Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 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
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
208000009157 neurocirculatory asthenia Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 1
229960001749 practolol Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
230000000213 tachycardiac effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA241,417A 1975-04-30 1975-12-10 Composes d'isoquinoline Expired CA1050986A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2519163A DE2519163C2 (de)	1975-04-30	1975-04-30	2-Formyl-1,2,3,4-tetrahydro-5-(2-hydroxy-3-tert.butyl-aminopropoxy)-isochinolin, dessen Salze, Verfahren zu deren Herstellung und ihre Verwendung

Publications (1)

Publication Number	Publication Date
CA1050986A true CA1050986A (fr)	1979-03-20

Family

ID=5945358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA241,417A Expired CA1050986A (fr)	1975-04-30	1975-12-10	Composes d'isoquinoline

Country Status (3)

Country	Link
JP (1)	JPS6032633B2 (fr)
CA (1)	CA1050986A (fr)
DE (1)	DE2519163C2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5280667A (en) *	1975-12-26	1977-07-06	Kazuo Tsumura	High frequency heating type deodorizing apparatus

1975
- 1975-04-30 DE DE2519163A patent/DE2519163C2/de not_active Expired
- 1975-12-10 CA CA241,417A patent/CA1050986A/fr not_active Expired
1976
- 1976-01-01 JP JP51000401A patent/JPS6032633B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2519163A1 (de)	1976-11-11
DE2519163C2 (de)	1983-12-01
JPS6032633B2 (ja)	1985-07-29
JPS51131882A (en)	1976-11-16

Publication	Publication Date	Title
US4276304A (en)	1981-06-30	Novel benzylalcohol derivative and process for preparing the same
CA1296011C (fr)	1992-02-18	Acide de type ¬(phenyl-sulfamoyl ou sulfonamido)-1,2,3,4-tetrahydroisoquinoline-2-yl\| alkyle
IL49205A (en)	1977-05-31	5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole its production and pharmaceutical compositions containing it
US3671570A (en)	1972-06-20	Derivatives of 9-oxo-15-hydroxyprostanoic acid, homologs thereof and their preparation
CA1050986A (fr)	1979-03-20	Composes d'isoquinoline
US4013663A (en)	1977-03-22	Isoquinoline compounds
US3998835A (en)	1976-12-21	1-Substituted amino-3-thieno-[3,2-c]pyridinyloxy-2-propanols
EP0113910B1 (fr)	1989-10-11	Dérivés de l'isocarbostyrile, procédé pour leur préparation et compositions pharmaceutiques les contenant
US3067203A (en)	1962-12-04	Tetrahybroisqquinoline derivatives
US3459755A (en)	1969-08-05	Process of producing 2-lower alkyl-5,6,7 or 8-hydroxy decahydroisoquinolines
US4054659A (en)	1977-10-18	5,7 Dihydroxy-1-(trimethoxybenzyl)-1,2,3,H-tetrahydroisoquinolines and use thereof
DK171299B1 (da)	1996-08-26	4-Amino-6,7-dimethoxy-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)quinolin-forbindelser, farmaceutiske præparater indeholdende disse og deres anvendelse til fremstilling af antiarytmiske lægemidler
US4067873A (en)	1978-01-10	Certain 1-amino-3-(1-isoquinolinyl)oxy-2-propanol derivatives
US4143143A (en)	1979-03-06	Substituted imidazo[5,1-a]isoquinolines
JPS5943946B2 (ja)	1984-10-25	Ｎ−アルケニルモラノリン誘導体
CA1093079A (fr)	1981-01-06	Procede d'obtention et emploi comme antidepressifs de 4-phenyl-8-amino-tetrahydroisoquinolines et de medicaments les contenant
US4302458A (en)	1981-11-24	Phthalidyl-isoquinoline derivatives
US3146266A (en)	1964-08-25	Novel ketone compounds
US4121036A (en)	1978-10-17	3-Amino-2-Hydrazinopyridine derivatives
CA1098129A (fr)	1981-03-24	Derives de la pyridil-piperazine et procede de preparation
CA1331005C (fr)	1994-07-26	Pyridylethanolamines, compositions pharmaceutiques en contenant et procedes pour leur preparation
US3583994A (en)	1971-06-08	5-benzoyloxy-2-lower alkyl decahydroisoquinolines
JPS5943947B2 (ja)	1984-10-25	Ｎ−置換モラノリン誘導体
KR820001081B1 (ko)	1982-06-21	모라노린 유도체의 제법
KR820001122B1 (ko)	1982-06-26	N-알케닐 몰라노린 유도체의 제조방법