CS238601B2 - Preparation method of o-methylate hydroxyaporphines - Google Patents

Preparation method of o-methylate hydroxyaporphines Download PDF

Info

Publication number: CS238601B2
Authority: CS; Czechoslovakia
Prior art keywords: carbon atoms; substituents; formula; reaction; solvent
Prior art date: 1977-12-22

Application number

CS788857A

Other languages

Czech (cs)

English (en)

Inventor

Johannes Hartenstein

Gerhard Satzinger

Original Assignee

Warner Lambert Co

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.)

1977-12-22

Filing date

1978-12-22

Publication date

1985-12-16

1978-12-22 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1985-12-16 Publication of CS238601B2 publication Critical patent/CS238601B2/cs

Links

MVRYYBFJTYHDQY-UHFFFAOYSA-N 6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-1-ol Chemical class C12=CC=CC=C2CC2N(C)CCC3=CC=C(O)C1=C32 MVRYYBFJTYHDQY-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims description 9
238000000034 method Methods 0.000 claims abstract description 33
238000007069 methylation reaction Methods 0.000 claims abstract description 23
ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 claims abstract description 9
239000002168 alkylating agent Substances 0.000 claims abstract description 4
229940100198 alkylating agent Drugs 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
-1 methylenedioxy Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
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
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
239000011877 solvent mixture Substances 0.000 claims description 2
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 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
239000000047 product Substances 0.000 description 13
230000011987 methylation Effects 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
BZKUYNBAFQJRDM-UHFFFAOYSA-N aporphine Chemical group C12=CC=CC=C2CC2N(C)CCC3=CC=CC1=C32 BZKUYNBAFQJRDM-UHFFFAOYSA-N 0.000 description 5
150000008441 aporphines Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012022 methylating agents‎ Substances 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000001035 methylating effect Effects 0.000 description 3
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
HLUNBGMOGGEWFX-FQEVSTJZSA-N 2-[[(6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-yl]oxy]-4,5-dimethoxybenzaldehyde Chemical compound COc1cc(Oc2cc3C[C@@H]4N(C)CCc5cc(OC)c(OC)c(-c3cc2OC)c45)c(C=O)cc1OC HLUNBGMOGGEWFX-FQEVSTJZSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
HLUNBGMOGGEWFX-UHFFFAOYSA-N Hernandaline Natural products C1=C(OC)C(OC)=CC(OC=2C(=CC=3C=4C(OC)=C(OC)C=C5CCN(C)C(C=45)CC=3C=2)OC)=C1C=O HLUNBGMOGGEWFX-UHFFFAOYSA-N 0.000 description 2
LINHZVMHXABQLB-ZDUSSCGKSA-N Isoboldine Chemical compound CN1CCC2=CC(OC)=C(O)C3=C2[C@@H]1CC1=C3C=C(OC)C(O)=C1 LINHZVMHXABQLB-ZDUSSCGKSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
QCMQEZNBBPGFKQ-UHFFFAOYSA-N Thalisopynine Natural products CN1CCC2=C(OC)C(OC)=C(OC)C3=C2C1CC1=C3C=C(OC)C(O)=C1 QCMQEZNBBPGFKQ-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
CRSMCADHSFQBLA-UHFFFAOYSA-N isoboldine Natural products COc1cc-2c(CC3N(C)CCc4cccc-2c34)cc1O CRSMCADHSFQBLA-UHFFFAOYSA-N 0.000 description 2
FVRABHGHBLRNNR-UHFFFAOYSA-N liriodenine Natural products O=C1C=CC=c2c1cc3nccc4cc5OCOc5c2c34 FVRABHGHBLRNNR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229960005181 morphine Drugs 0.000 description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
DYAAXURJUVSJEZ-AWEZNQCLSA-N (+)-Mecambroline Chemical compound C12=C3C4=CC(O)=CC=C4C[C@@H]1N(C)CCC2=CC1=C3OCO1 DYAAXURJUVSJEZ-AWEZNQCLSA-N 0.000 description 1
MAWRLMCDVKBYJB-UHFFFAOYSA-N (+-)-normecambroline Natural products C12=C3C4=CC(O)=CC=C4CC2NCCC1=CC1=C3OCO1 MAWRLMCDVKBYJB-UHFFFAOYSA-N 0.000 description 1
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
YRYCIFUZSUMAAY-UHFFFAOYSA-N (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1CC1=CC=CC=C1 YRYCIFUZSUMAAY-UHFFFAOYSA-N 0.000 description 1
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical group C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
ISQZUTSKBGVRCP-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-phenylmethoxy-2-propyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=C2C(CC=3C=C(OC)C(OC)=CC=3)N(CCC)CCC2=CC(OC)=C1OCC1=CC=CC=C1 ISQZUTSKBGVRCP-UHFFFAOYSA-N 0.000 description 1
QJNKQDCTABVPGW-UHFFFAOYSA-N 1-methoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline Chemical class C1CN(C)C2CC3=CC=CC=C3C3=C2C1=CC=C3OC QJNKQDCTABVPGW-UHFFFAOYSA-N 0.000 description 1
HCXDSTXYBRCIQC-UHFFFAOYSA-N 10,11-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline Chemical compound CN1CCC2=CC=CC3=C2C1CC1=CC=C(OC)C(OC)=C13 HCXDSTXYBRCIQC-UHFFFAOYSA-N 0.000 description 1
LINHZVMHXABQLB-UHFFFAOYSA-N 2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-1,9-diol Chemical compound CN1CCC2=CC(OC)=C(O)C3=C2C1CC1=C3C=C(OC)C(O)=C1 LINHZVMHXABQLB-UHFFFAOYSA-N 0.000 description 1
RLIPQCDHACHPJW-UHFFFAOYSA-N 2,3,4-trimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1C RLIPQCDHACHPJW-UHFFFAOYSA-N 0.000 description 1
PLEOQAHCVRVCDL-UHFFFAOYSA-N 2,9-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,10-diol Natural products CN1CCC2=CC(OC)=C(O)C3=C2C1CC1=C3C=C(O)C(OC)=C1 PLEOQAHCVRVCDL-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
ZVSSFDDZYJFDDC-UHFFFAOYSA-N 6-methyl-1-phenoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline Chemical compound O(C1=CC=CC=C1)C1=CC=C2CCN(C)C3CC4=CC=CC=C4C1=C23 ZVSSFDDZYJFDDC-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
RELZHBBKERFUAJ-UHFFFAOYSA-N Apoglaziovin Natural products N1CCC2=CC(OC)=C(O)C3=C2C1CC1=CC=C(OC)C=C13 RELZHBBKERFUAJ-UHFFFAOYSA-N 0.000 description 1
LZJRNLRASBVRRX-ZDUSSCGKSA-N Boldine Chemical compound CN1CCC2=CC(O)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(O)=C1 LZJRNLRASBVRRX-ZDUSSCGKSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
LMZPADPFSOKFTR-UHFFFAOYSA-N CCCN(CCC1=C2)C(CC(C=C3)=CC(OC)=C3OC)C1=CC(OCC1=CC=CC=C1)=C2OC.I Chemical compound CCCN(CCC1=C2)C(CC(C=C3)=CC(OC)=C3OC)C1=CC(OCC1=CC=CC=C1)=C2OC.I LMZPADPFSOKFTR-UHFFFAOYSA-N 0.000 description 1
108700018454 CDC15 Proteins 0.000 description 1
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DYAAXURJUVSJEZ-UHFFFAOYSA-N DL-Mecambrolin Natural products C12=C3C4=CC(O)=CC=C4CC1N(C)CCC2=CC1=C3OCO1 DYAAXURJUVSJEZ-UHFFFAOYSA-N 0.000 description 1
ZTXGGRMVULLHNF-UHFFFAOYSA-N Dehydroneolitsine Natural products CN1CCc2cc3OCOc3c4c5cc6OCOc6cc5cc1c24 ZTXGGRMVULLHNF-UHFFFAOYSA-N 0.000 description 1
TWHQHABOPHKTTM-UHFFFAOYSA-N Isocorydin Natural products C1C2=CC=C(OC)C(O)=C2C2=CC(OC)=CC3=C2C1N(C)CC3 TWHQHABOPHKTTM-UHFFFAOYSA-N 0.000 description 1
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229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
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VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000006399 behavior Effects 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
244000309464 bull Species 0.000 description 1
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230000000711 cancerogenic effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
101150081467 cdc15 gene Proteins 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
HORZNQYQXBFWNZ-UHFFFAOYSA-N dl-Norisoboldin Natural products N1CCC2=CC(OC)=C(O)C3=C2C1CC1=C3C=C(OC)C(O)=C1 HORZNQYQXBFWNZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
DRVVGOFZCWCCSA-UHFFFAOYSA-N isocorydine Natural products COc1cc2CCN(C)C3Cc4cccc(C)c4c(c1O)c23 DRVVGOFZCWCCSA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229930013397 isoquinoline alkaloid Natural products 0.000 description 1
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
RQCOQZNIQLKGTN-ZDUSSCGKSA-N isothebaine Chemical compound C1C2=CC=CC(OC)=C2C2=C(O)C(OC)=CC3=C2[C@H]1N(C)CC3 RQCOQZNIQLKGTN-ZDUSSCGKSA-N 0.000 description 1
UFOCZRJLUKCVKZ-UHFFFAOYSA-N isothebaine Natural products CN1CCC2=CC(OC)=C(O)C3=C2C1CC1=CC=C(OC)C=C13 UFOCZRJLUKCVKZ-UHFFFAOYSA-N 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229930013053 morphinan alkaloid Natural products 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (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)

CS788857A 1977-12-22 1978-12-22 Preparation method of o-methylate hydroxyaporphines CS238601B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2757335A DE2757335C3 (de)	1977-12-22	1977-12-22	Verfahren zur O-Methylierung von Hydroxyaporphinen

Publications (1)

Publication Number	Publication Date
CS238601B2 true CS238601B2 (en)	1985-12-16

Family

ID=6026924

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS788857A CS238601B2 (en)	1977-12-22	1978-12-22	Preparation method of o-methylate hydroxyaporphines

Country Status (14)

Country	Link
US (1)	US4309542A (fr)
JP (1)	JPS54119474A (fr)
AT (1)	AT362535B (fr)
BE (1)	BE872843A (fr)
CH (1)	CH645629A5 (fr)
CS (1)	CS238601B2 (fr)
DD (1)	DD141830A5 (fr)
DE (1)	DE2757335C3 (fr)
FI (1)	FI68222C (fr)
FR (1)	FR2430942A1 (fr)
GB (1)	GB2010841B (fr)
HU (1)	HU177060B (fr)
NL (1)	NL7812394A (fr)
SU (1)	SU925249A3 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3118521A1 (de) *	1981-05-09	1982-12-02	Gödecke AG, 1000 Berlin	Dibenzo(de,g)chinolin-derivate, verfahren zu deren herstellung und deren verwendung bei der bekaempfung von erkaeltungskrankheiten und allergien
US4795759A (en) *	1985-07-27	1989-01-03	Sandoz Ltd.	Use of dibenz(CD,F)indoles
US6210680B1 (en)	1999-06-11	2001-04-03	Univera Pharmaceuticals, Inc.	Method for the prevention and treatment of chronic venous insufficiency
TWI225397B (en) *	2000-05-04	2004-12-21	Nat Science Council	Uses of thaliporphine or its derivatives in treatment of cardiac diseases and preparation of the same
KR100522008B1 (ko) *	2000-08-23	2005-10-18	로터스 파마세티컬 리미티드 컴퍼니	심장병 치료 및 예방에 있어서의 탈리포르핀 또는 그유도체의 용도
JP2006527699A (ja) *	2003-06-19	2006-12-07	美時化学製薬股▲ふん▼有限公司	アポルフィン、及び、ケトンアポルフィン化合物とその用途
CN1884265A (zh) *	2005-06-20	2006-12-27	美时化学制药股份有限公司	治疗糖尿病的阿朴芬及次阿朴芬化合物
WO2007134485A1 (fr) *	2006-05-22	2007-11-29	Lotus Pharmaceutical Co., Ltd.	Composés aporphiniques et oxoaporphiniques et utilisation pharmaceutique correspondante
TWI531369B (zh) *	2014-05-30	2016-05-01	資元堂生物科技股份有限公司	阿朴啡生物鹼衍生物用於製備促進ａｍｐｋ活性的藥物之用途
CN111196801B (zh) *	2020-01-14	2022-10-14	中国药科大学	阿朴菲类生物碱衍生物及其制备方法与用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1100998A (en) *	1912-05-06	1914-06-23	Firm Of Mckesson & Robbins	Process of manufacuring alkyl-ethers of morphin.
GB1364318A (en) *	1971-03-15	1974-08-21	Bellon Labor Sa Roger	Laurotetanine derivatives
DE2337507A1 (de) *	1973-07-24	1975-02-13	Research Corp	Verfahren zur herstellung von aporphinen ueber neue zwischenprodukte
DE2625116C2 (de) *	1976-06-04	1984-01-26	Gödecke AG, 1000 Berlin	Verfahren zur Herstellung von 4-Hydroxy-aporphin-Derivaten

1977
- 1977-12-22 DE DE2757335A patent/DE2757335C3/de not_active Expired
1978
- 1978-12-14 FR FR7835193A patent/FR2430942A1/fr active Granted
- 1978-12-18 BE BE192382A patent/BE872843A/fr not_active IP Right Cessation
- 1978-12-19 US US05/971,143 patent/US4309542A/en not_active Expired - Lifetime
- 1978-12-19 GB GB7849004A patent/GB2010841B/en not_active Expired
- 1978-12-20 DD DD78209943A patent/DD141830A5/de unknown
- 1978-12-21 FI FI783951A patent/FI68222C/fi not_active IP Right Cessation
- 1978-12-21 JP JP15695578A patent/JPS54119474A/ja active Pending
- 1978-12-21 NL NL7812394A patent/NL7812394A/xx not_active Application Discontinuation
- 1978-12-21 CH CH1305678A patent/CH645629A5/de not_active IP Right Cessation
- 1978-12-21 HU HU78WA355A patent/HU177060B/hu unknown
- 1978-12-21 AT AT913578A patent/AT362535B/de not_active IP Right Cessation
- 1978-12-21 SU SU782700555A patent/SU925249A3/ru active
- 1978-12-22 CS CS788857A patent/CS238601B2/cs unknown

Also Published As

Publication number	Publication date
CH645629A5 (de)	1984-10-15
DE2757335C3 (de)	1982-03-25
FI68222B (fi)	1985-04-30
HU177060B (hu)	1981-06-28
FI68222C (fi)	1985-08-12
FI783951A7 (fi)	1979-06-23
ATA913578A (de)	1980-10-15
US4309542A (en)	1982-01-05
SU925249A3 (ru)	1982-04-30
DE2757335A1 (de)	1979-06-28
FR2430942A1 (fr)	1980-02-08
NL7812394A (nl)	1979-06-26
JPS54119474A (en)	1979-09-17
BE872843A (fr)	1979-04-17
GB2010841A (en)	1979-07-04
GB2010841B (en)	1982-08-18
AT362535B (de)	1981-05-25
DE2757335B2 (de)	1981-05-27
FR2430942B1 (fr)	1985-02-22
DD141830A5 (de)	1980-05-21

Publication	Publication Date	Title
GB2141716A (en)	1985-01-03	Oxazolidines
CS238601B2 (en)	1985-12-16	Preparation method of o-methylate hydroxyaporphines
JPS6113472B2 (fr)	1986-04-14
KR20120006057A (ko)	2012-01-17	벤제노이드 다이아조늄 염의 교차-커플링 산물의 제조 방법
EP2170840A1 (fr)	2010-04-07	Procédé perfectionné pour la préparation d'un dérivé de la purine
EP0099303B1 (fr)	1987-08-19	Nouvelles benzothiopyranopyridinones et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant
US4013666A (en)	1977-03-22	(8α,13Aβ)-8-CARBOCYCLIC/CARBOCYCLIC METHYL-5,8,13,13A-TETRAHYDRO-2,3,10,11-TETRAMETHOXY-6H-dibenzo[a,g]quinolizines and intermediates thereto
FR2510575A1 (fr)	1983-02-04	Nouveaux composes bicycliques, leur procede de preparation et composition pharmaceutique les renfermant
EP0202950B1 (fr)	1993-09-29	Dérivés de berbane et leur préparation et composition pharmaceutique
US4336192A (en)	1982-06-22	5,6-Dihydro-11-alkylene-morphanthridin-6-ones
US4656179A (en)	1987-04-07	Isoquinoline derivatives, and pharmaceutical compositions containing them
DK141629B (da)	1980-05-12	Analogifremgangsmaade til fremstilling af 7alfasubstituerede n-(furylmethyl)-6,14-endoetheno-eller-6,14-endoethano-tetrahydronororipaviner eller syreadditionssalte deraf
SU493965A3 (ru)	1975-11-28	Способ получени д-2-замещенных-6-алкил8-замещенных эрголинов
FI85702B (fi)	1992-02-14	Foerfarande foer framstaellning av tert.-butyl-ergolinderivat.
Shutske et al.	1993	Synthesis of Some amino‐4, 5‐dihydropyrazolo [3, 4‐a] acridines as potential cholinesterase inhibitors
PL140164B1 (en)	1987-03-31	Process for preparing novel derivatives of 8-carbonylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinoline
EP0026505A1 (fr)	1981-04-08	1-Phényl-2,3,4,5-tétrahydro 1-H-3-benzazépines 7,8-substituées
EP0015786B1 (fr)	1982-04-21	Imidazo et pyrimido-pyrido-indoles, leur préparation et médicaments les contenant
Kotick et al.	1981	8β‐Substituted dihydrocodeinones having heteroatoms in the side chain
US3635962A (en)	1972-01-18	4 - bis-morpholino- and 2
CS196323B2 (en)	1980-03-31	Method of producing novel derivatives of isoindoline
US4013644A (en)	1977-03-22	[8 α(E), 13aβ]-5,8,13,13a-tetrahydro-2,3,10,11-tetramethoxy-8-(2-phenylethenyl)-6H-dibenzo[a,g]quinolizines and intermediates thereto
CS208741B2 (en)	1981-09-15	Method of making the new derivatives of the 6,7-dimetoxyisochinolinacetamide
GB2099812A (en)	1982-12-15	Process for the preparation of benz (e) indolines
KR800001551B1 (ko)	1980-12-27	환상 화합물의 제조방법