DE1695591A1 - Verfahren zur Herstellung von 2-[2-Thienyl-(2)-aethyl]-delta1-pyrrolin und -tetrahydropyridin - Google Patents
Verfahren zur Herstellung von 2-[2-Thienyl-(2)-aethyl]-delta1-pyrrolin und -tetrahydropyridinInfo
- Publication number
- DE1695591A1 DE1695591A1 DE19651695591 DE1695591A DE1695591A1 DE 1695591 A1 DE1695591 A1 DE 1695591A1 DE 19651695591 DE19651695591 DE 19651695591 DE 1695591 A DE1695591 A DE 1695591A DE 1695591 A1 DE1695591 A1 DE 1695591A1
- Authority
- DE
- Germany
- Prior art keywords
- thienyl
- pyrroline
- tetrahydropyridine
- formula
- addition salts
- 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 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 206010061217 Infestation Diseases 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241001126260 Nippostrongylus Species 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 241001478880 Streptobacillus moniliformis Species 0.000 description 2
- 241000975692 Syphacia obvelata Species 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- -1 G-luconate Chemical compound 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241001126263 Strongylidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000243792 Trichostrongylidae Species 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229950003153 amsonate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000282 effect on parasite Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- 229960003750 ethyl chloride Drugs 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
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 244000000050 gastrointestinal parasite Species 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 239000000155 melt Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3700/64A GB1045838A (en) | 1964-01-28 | 1964-01-28 | 2-substituted thiophen derivatives |
| GB32987/64A GB1049047A (en) | 1964-01-28 | 1964-08-13 | 2-ethylthiophen derivatives |
| GB3933164 | 1964-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695591A1 true DE1695591A1 (de) | 1972-03-16 |
Family
ID=27254315
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651695591 Pending DE1695591A1 (de) | 1964-01-28 | 1965-01-28 | Verfahren zur Herstellung von 2-[2-Thienyl-(2)-aethyl]-delta1-pyrrolin und -tetrahydropyridin |
| DE1745778A Expired DE1745778C3 (de) | 1964-01-28 | 1965-01-28 | 1-Methyl-2- eckige Klammer auf 2-(2-thienyl)-vinyl eckige Klammer zu -Delta hoch 2- tetrahydropyrimidin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1745778A Expired DE1745778C3 (de) | 1964-01-28 | 1965-01-28 | 1-Methyl-2- eckige Klammer auf 2-(2-thienyl)-vinyl eckige Klammer zu -Delta hoch 2- tetrahydropyrimidin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3336323A (forum.php) |
| BE (1) | BE658987A (forum.php) |
| BR (1) | BR6566538D0 (forum.php) |
| CY (1) | CY405A (forum.php) |
| DE (2) | DE1695591A1 (forum.php) |
| ES (1) | ES308607A1 (forum.php) |
| FR (1) | FR1466244A (forum.php) |
| GB (2) | GB1045838A (forum.php) |
| IT (1) | IT1061754B (forum.php) |
| MY (1) | MY6700157A (forum.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4369175A (en) | 1981-07-27 | 1983-01-18 | Ciba-Geigy Corporation | Process for the manufacture of prolonged action vincamine preparations, the vincamine preparations so obtained, and medicaments containing them |
| JP2012184201A (ja) * | 2011-03-07 | 2012-09-27 | Nippon Zeon Co Ltd | 環状エーテル化合物、非水系電池電極用バインダー組成物、非水系電池電極用スラリー組成物、非水系電池用電極及び非水系電池 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526319A (en) * | 1946-07-27 | 1950-10-17 | Sprague Electric Co | Thienyl ethylene compounds |
-
1964
- 1964-01-28 GB GB3700/64A patent/GB1045838A/en not_active Expired
- 1964-08-13 GB GB32987/64A patent/GB1049047A/en not_active Expired
-
1965
- 1965-01-27 IT IT01432/65A patent/IT1061754B/it active
- 1965-01-27 FR FR3458A patent/FR1466244A/fr not_active Expired
- 1965-01-27 BR BR166538/65A patent/BR6566538D0/pt unknown
- 1965-01-27 ES ES0308607A patent/ES308607A1/es not_active Expired
- 1965-01-28 DE DE19651695591 patent/DE1695591A1/de active Pending
- 1965-01-28 DE DE1745778A patent/DE1745778C3/de not_active Expired
- 1965-01-28 BE BE658987D patent/BE658987A/xx unknown
- 1965-07-23 US US474463A patent/US3336323A/en not_active Expired - Lifetime
-
1967
- 1967-09-07 CY CY40567A patent/CY405A/xx unknown
- 1967-12-31 MY MY1967157A patent/MY6700157A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES308607A1 (es) | 1965-09-01 |
| CY405A (en) | 1967-09-07 |
| DE1745778B2 (de) | 1974-07-11 |
| DE1745778C3 (de) | 1975-03-20 |
| FR1466244A (fr) | 1967-01-20 |
| IT1061754B (it) | 1983-04-30 |
| DE1745778A1 (de) | 1972-04-20 |
| BR6566538D0 (pt) | 1973-08-02 |
| MY6700157A (en) | 1967-12-31 |
| GB1045838A (en) | 1966-10-19 |
| BE658987A (forum.php) | 1965-07-28 |
| GB1049047A (en) | 1966-11-23 |
| US3336323A (en) | 1967-08-15 |
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