CH509315A - Verfahren zur Herstellung von Salzen der optisch aktiven Formen von 1-(3,4,5-Trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisochinolin - Google Patents
Verfahren zur Herstellung von Salzen der optisch aktiven Formen von 1-(3,4,5-Trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisochinolinInfo
- Publication number
- CH509315A CH509315A CH625368A CH625368A CH509315A CH 509315 A CH509315 A CH 509315A CH 625368 A CH625368 A CH 625368A CH 625368 A CH625368 A CH 625368A CH 509315 A CH509315 A CH 509315A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydroisoquinoline
- optically active
- acid
- trimethoxybenzyl
- dihydroxy
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000001640 fractional crystallisation Methods 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- RGVPOXRFEPSFGH-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 RGVPOXRFEPSFGH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 12
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229960001270 d- tartaric acid Drugs 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000003182 bronchodilatating effect Effects 0.000 abstract description 3
- 230000003177 cardiotonic effect Effects 0.000 abstract description 2
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000013078 crystal Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- -1 alkyl acetates Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 229940095064 tartrate Drugs 0.000 description 4
- 239000011345 viscous material Substances 0.000 description 4
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 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
- 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
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- PDZYOCOHQGFKLC-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)acetaldehyde Chemical compound COC1=CC(CC=O)=CC(OC)=C1OC PDZYOCOHQGFKLC-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 238000006929 Pictet-Spengler synthesis reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- MIOPJNTWMNEORI-ZDFGOMNRSA-N [2,2,3,3,4,5,5-heptadeuterio-7-methyl-6-oxo-7-(trideuteriomethyl)-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C12(C(=O)C(C(C(C1([2H])[2H])([2H])[2H])(C2(C([2H])([2H])[2H])C)[2H])([2H])[2H])CS(=O)(=O)O MIOPJNTWMNEORI-ZDFGOMNRSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2724167 | 1967-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH509315A true CH509315A (de) | 1971-06-30 |
Family
ID=12215566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH625368A CH509315A (de) | 1967-04-27 | 1968-04-26 | Verfahren zur Herstellung von Salzen der optisch aktiven Formen von 1-(3,4,5-Trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisochinolin |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT280288B (en:Method) |
| BE (1) | BE714193A (en:Method) |
| BR (1) | BR6898628D0 (en:Method) |
| CH (1) | CH509315A (en:Method) |
| CS (1) | CS150953B2 (en:Method) |
| DE (1) | DE1770286A1 (en:Method) |
| DK (1) | DK120082B (en:Method) |
| ES (1) | ES353219A1 (en:Method) |
| FI (1) | FI50335C (en:Method) |
| FR (2) | FR1584255A (en:Method) |
| GB (1) | GB1173719A (en:Method) |
| IL (1) | IL29832A (en:Method) |
| MY (1) | MY7000174A (en:Method) |
| NL (1) | NL6805964A (en:Method) |
| SE (1) | SE328575B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BG38182A1 (en) * | 1983-06-21 | 1985-11-15 | Ivanova | Tocolytic means |
-
1968
- 1968-04-05 BR BR198628/68*7A patent/BR6898628D0/pt unknown
- 1968-04-16 IL IL29832A patent/IL29832A/xx unknown
- 1968-04-25 FI FI681156A patent/FI50335C/fi active
- 1968-04-25 BE BE714193D patent/BE714193A/xx not_active IP Right Cessation
- 1968-04-25 GB GB09533/68A patent/GB1173719A/en not_active Expired
- 1968-04-26 CH CH625368A patent/CH509315A/de not_active IP Right Cessation
- 1968-04-26 AT AT408868A patent/AT280288B/de active
- 1968-04-26 SE SE05743/68A patent/SE328575B/xx unknown
- 1968-04-26 DK DK194068AA patent/DK120082B/da unknown
- 1968-04-26 DE DE19681770286 patent/DE1770286A1/de active Pending
- 1968-04-26 NL NL6805964A patent/NL6805964A/xx unknown
- 1968-04-26 FR FR1584255D patent/FR1584255A/fr not_active Expired
- 1968-04-26 ES ES353219A patent/ES353219A1/es not_active Expired
- 1968-04-26 CS CS3106A patent/CS150953B2/cs unknown
- 1968-07-25 FR FR307D patent/FR307F/fr not_active Expired
-
1970
- 1970-12-31 MY MY1970174A patent/MY7000174A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6898628D0 (pt) | 1973-03-08 |
| AT280288B (de) | 1970-04-10 |
| NL6805964A (en:Method) | 1968-10-28 |
| FR1584255A (en:Method) | 1969-12-19 |
| SE328575B (en:Method) | 1970-09-21 |
| BE714193A (en:Method) | 1968-09-16 |
| ES353219A1 (es) | 1969-09-01 |
| GB1173719A (en) | 1969-12-10 |
| IL29832A (en) | 1971-04-28 |
| MY7000174A (en) | 1970-12-31 |
| FI50335C (fi) | 1976-02-10 |
| IL29832A0 (en) | 1968-06-20 |
| FR307F (en:Method) | 1970-04-13 |
| DK120082B (da) | 1971-04-05 |
| CS150953B2 (en:Method) | 1973-09-17 |
| FI50335B (en:Method) | 1975-10-31 |
| DE1770286A1 (de) | 1970-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |