DE2534410A1 - Verfahren zur herstellung von 1-hydroxy-2-methoxy-proaporphinen - Google Patents
Verfahren zur herstellung von 1-hydroxy-2-methoxy-proaporphinenInfo
- Publication number
- DE2534410A1 DE2534410A1 DE19752534410 DE2534410A DE2534410A1 DE 2534410 A1 DE2534410 A1 DE 2534410A1 DE 19752534410 DE19752534410 DE 19752534410 DE 2534410 A DE2534410 A DE 2534410A DE 2534410 A1 DE2534410 A1 DE 2534410A1
- Authority
- DE
- Germany
- Prior art keywords
- selective hydrolysis
- methoxy
- aporphines
- dimethoxy
- proaporphines
- Prior art date
- 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.)
- Withdrawn
Links
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 9
- 239000001257 hydrogen Substances 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 title claims description 3
- -1 hydrogen halides Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 12
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 5
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 5
- ORJVQPIHKOARKV-UHFFFAOYSA-N 1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline Chemical compound C1C2=CC=CC=C2C2=C(OC)C(OC)=CC3=C2C1N(C)CC3 ORJVQPIHKOARKV-UHFFFAOYSA-N 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- OLMDPVRISKOBIT-UHFFFAOYSA-N N-methylcrotsparine Natural products COc1cc2CCN(C)C3c2c(CC34C=CC(=O)C=C4)c1O OLMDPVRISKOBIT-UHFFFAOYSA-N 0.000 abstract description 7
- 229930013930 alkaloid Natural products 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 241000909583 Ocotea Species 0.000 abstract description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 230000003001 depressive effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- OGJKMZVUJJYWKO-UHFFFAOYSA-N proaporphine Natural products C1=2C3=C(OC)C(OC)=CC=2CCNC1CC13C=CC(=O)C=C1 OGJKMZVUJJYWKO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- PNJUPRNTSWJWAX-ZDUSSCGKSA-N glaziovine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C3C=21)O)OC)C13C=CC(=O)C=C1 PNJUPRNTSWJWAX-ZDUSSCGKSA-N 0.000 abstract 1
- 229950005847 glaziovine Drugs 0.000 abstract 1
- 229930004040 glaziovine Natural products 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- URYIHIIOFWGCIU-UHFFFAOYSA-N Roehybrin Natural products COC1CC2(CCC1=O)CC3N(C)CCc4cc(OC)c(O)c2c34 URYIHIIOFWGCIU-UHFFFAOYSA-N 0.000 description 5
- WTVDRHSULHNSJV-UHFFFAOYSA-N isoamuronine Natural products C1=2C3=C(OC)C(OC)=CC=2CCN(C)C1CC13CCC(=O)C=C1 WTVDRHSULHNSJV-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- WUYQEGNOQLRQAQ-CQSZACIVSA-N (+)-pronuciferine Chemical compound C([C@H]1N(C)CCC=2C=C(C(=C3C=21)OC)OC)C13C=CC(=O)C=C1 WUYQEGNOQLRQAQ-CQSZACIVSA-N 0.000 description 3
- WUYQEGNOQLRQAQ-UHFFFAOYSA-N (+)-pronuciferine Natural products C1=2C3=C(OC)C(OC)=CC=2CCN(C)C1CC13C=CC(=O)C=C1 WUYQEGNOQLRQAQ-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 description 1
- 241000766026 Coregonus nasus Species 0.000 description 1
- BIQCPSFLUXLSBH-UHFFFAOYSA-N N-Methyl-dihydro-crotsparinin Natural products C1=2C3=C(O)C(OC)=CC=2CCN(C)C1CC13CCC(=O)CC1 BIQCPSFLUXLSBH-UHFFFAOYSA-N 0.000 description 1
- 241000404883 Pisa Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008441 aporphines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940081090 cefa Drugs 0.000 description 1
- NFDFQCUYFHCNBW-SCGPFSFSSA-N dienestrol Chemical compound C=1C=C(O)C=CC=1\C(=C/C)\C(=C\C)\C1=CC=C(O)C=C1 NFDFQCUYFHCNBW-SCGPFSFSSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1077674A CH605782A5 (enrdf_load_stackoverflow) | 1974-08-07 | 1974-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2534410A1 true DE2534410A1 (de) | 1976-02-26 |
Family
ID=4366761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752534410 Withdrawn DE2534410A1 (de) | 1974-08-07 | 1975-08-01 | Verfahren zur herstellung von 1-hydroxy-2-methoxy-proaporphinen |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5141363A (enrdf_load_stackoverflow) |
| CH (1) | CH605782A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2534410A1 (enrdf_load_stackoverflow) |
-
1974
- 1974-08-07 CH CH1077674A patent/CH605782A5/xx not_active IP Right Cessation
-
1975
- 1975-08-01 DE DE19752534410 patent/DE2534410A1/de not_active Withdrawn
- 1975-08-04 JP JP9427975A patent/JPS5141363A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH605782A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| JPS5141363A (en) | 1976-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |