DE1174792B - Verfahren zur Herstellung von neuen 3-Phenyl-granaten-(2)-derivaten und ihren Hydrochloriden - Google Patents
Verfahren zur Herstellung von neuen 3-Phenyl-granaten-(2)-derivaten und ihren HydrochloridenInfo
- Publication number
- DE1174792B DE1174792B DEB69480A DEB0069480A DE1174792B DE 1174792 B DE1174792 B DE 1174792B DE B69480 A DEB69480 A DE B69480A DE B0069480 A DEB0069480 A DE B0069480A DE 1174792 B DE1174792 B DE 1174792B
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- general formula
- recrystallization
- derivatives
- hydrochlorides
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 150000003840 hydrochlorides Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
- -1 alkyl radicals Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000001953 recrystallisation Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 6
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000002223 garnet Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940048346 phenethylamine hydrochloride Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007363 regulatory process Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE639446D BE639446A (en:Method) | 1962-11-03 | ||
| DEB69480A DE1174792B (de) | 1962-11-03 | 1962-11-03 | Verfahren zur Herstellung von neuen 3-Phenyl-granaten-(2)-derivaten und ihren Hydrochloriden |
| LU44663D LU44663A1 (en:Method) | 1962-11-03 | 1963-10-21 | |
| DK508263A DK104065C (da) | 1962-11-03 | 1963-10-29 | Fremgangsmåde til fremstilling af 3-phenylgranaten-(2)-derivater. |
| CH1339563A CH436324A (de) | 1962-11-03 | 1963-10-31 | Verfahren zur Herstellung neuer 3-Phenyl-granaten-(2)-derivate |
| AT875863A AT241698B (de) | 1962-11-03 | 1963-10-31 | Verfahren zur Herstellung neuer 3-Phenyl-granaten-(2)-Derivate |
| GB4331563A GB983628A (en) | 1962-11-03 | 1963-11-01 | New 3-phenyl-granatene-(2) derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB69480A DE1174792B (de) | 1962-11-03 | 1962-11-03 | Verfahren zur Herstellung von neuen 3-Phenyl-granaten-(2)-derivaten und ihren Hydrochloriden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1174792B true DE1174792B (de) | 1964-07-30 |
Family
ID=6976304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB69480A Pending DE1174792B (de) | 1962-11-03 | 1962-11-03 | Verfahren zur Herstellung von neuen 3-Phenyl-granaten-(2)-derivaten und ihren Hydrochloriden |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT241698B (en:Method) |
| BE (1) | BE639446A (en:Method) |
| CH (1) | CH436324A (en:Method) |
| DE (1) | DE1174792B (en:Method) |
| DK (1) | DK104065C (en:Method) |
| GB (1) | GB983628A (en:Method) |
| LU (1) | LU44663A1 (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053744A1 (de) * | 1980-12-04 | 1982-06-16 | C.H. Boehringer Sohn | Neue 8-Arylalkyl-3-phenyl-3-nortropanole, deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
-
0
- BE BE639446D patent/BE639446A/xx unknown
-
1962
- 1962-11-03 DE DEB69480A patent/DE1174792B/de active Pending
-
1963
- 1963-10-21 LU LU44663D patent/LU44663A1/xx unknown
- 1963-10-29 DK DK508263A patent/DK104065C/da active
- 1963-10-31 CH CH1339563A patent/CH436324A/de unknown
- 1963-10-31 AT AT875863A patent/AT241698B/de active
- 1963-11-01 GB GB4331563A patent/GB983628A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053744A1 (de) * | 1980-12-04 | 1982-06-16 | C.H. Boehringer Sohn | Neue 8-Arylalkyl-3-phenyl-3-nortropanole, deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US4393069A (en) * | 1980-12-04 | 1983-07-12 | C. H. Boehringer Sohn | 8-Arylalkyl-3-phenyl-3-nortropanols and salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DK104065C (da) | 1966-03-28 |
| GB983628A (en) | 1965-02-17 |
| BE639446A (en:Method) | |
| LU44663A1 (en:Method) | 1963-12-21 |
| AT241698B (de) | 1965-08-10 |
| CH436324A (de) | 1967-05-31 |
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