DE1227464B - Verfahren zur Herstellung der trans-Form des neuen 1-(4'-Methylphenyl)-1-(2''-pyridyl)-3-pyrrolidinopropens-(1) - Google Patents
Verfahren zur Herstellung der trans-Form des neuen 1-(4'-Methylphenyl)-1-(2''-pyridyl)-3-pyrrolidinopropens-(1)Info
- Publication number
- DE1227464B DE1227464B DEW9428A DEW0009428A DE1227464B DE 1227464 B DE1227464 B DE 1227464B DE W9428 A DEW9428 A DE W9428A DE W0009428 A DEW0009428 A DE W0009428A DE 1227464 B DE1227464 B DE 1227464B
- Authority
- DE
- Germany
- Prior art keywords
- trans
- pyridyl
- acid
- methylphenyl
- cis
- 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
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000003891 oxalate salts Chemical class 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- WRSWNYCNECGVNL-UHFFFAOYSA-N 1-phenyl-3-pyrrolidin-1-ylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)CCN1CCCC1 WRSWNYCNECGVNL-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000004793 Polystyrene Substances 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004044 bronchoconstricting agent Substances 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- GUFUWKKDHIABBW-UHFFFAOYSA-N pyrrolidin-1-ylmethanol Chemical compound OCN1CCCC1 GUFUWKKDHIABBW-UHFFFAOYSA-N 0.000 description 1
- -1 pyrrolidinomethylene groups Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US245969A US2712020A (en) | 1948-07-20 | 1951-09-10 | Heterocyclic allylamines |
| US302821A US2712023A (en) | 1948-07-20 | 1952-08-05 | Alkyl substituted antihistamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1227464B true DE1227464B (de) | 1966-10-27 |
Family
ID=26673905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEW9428A Pending DE1227464B (de) | 1951-09-10 | 1952-09-08 | Verfahren zur Herstellung der trans-Form des neuen 1-(4'-Methylphenyl)-1-(2''-pyridyl)-3-pyrrolidinopropens-(1) |
Country Status (5)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085959A3 (en) * | 1982-02-04 | 1984-07-18 | The Wellcome Foundation Limited | Aromatic compounds |
| US4501893A (en) * | 1982-02-04 | 1985-02-26 | Findlay John W A | 3-{6-[3-Pyrrolidino-1-(4-tolyl)prop-1-enyl]-2-pyridyl}acrylic acid and pharmaceutically acceptable salts thereof |
| US4564685A (en) * | 1983-03-10 | 1986-01-14 | Findlay John W A | Diphenylmethane compounds |
| US4584382A (en) * | 1983-02-01 | 1986-04-22 | Findlay John W A | Pyridyl acrylate compound |
| US4621094A (en) * | 1983-03-10 | 1986-11-04 | Findlay John W A | Anti-histaminic pyridyl compounds |
| US4639459A (en) * | 1983-02-01 | 1987-01-27 | Burroughs Wellcome Co. | Use of trifluoromethyl compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124585A (en) * | 1964-03-10 | Z-pymibyl |
-
1952
- 1952-09-08 DE DEW9428A patent/DE1227464B/de active Pending
- 1952-09-09 BE BE514068D patent/BE514068A/fr unknown
- 1952-09-09 FR FR1080465D patent/FR1080465A/fr not_active Expired
- 1952-09-09 NL NL172357A patent/NL84175C/nl active
- 1952-09-09 CH CH308141D patent/CH308141A/fr unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085959A3 (en) * | 1982-02-04 | 1984-07-18 | The Wellcome Foundation Limited | Aromatic compounds |
| US4501893A (en) * | 1982-02-04 | 1985-02-26 | Findlay John W A | 3-{6-[3-Pyrrolidino-1-(4-tolyl)prop-1-enyl]-2-pyridyl}acrylic acid and pharmaceutically acceptable salts thereof |
| US4650807A (en) * | 1982-02-04 | 1987-03-17 | Burroughs Wellcome Co. | Antihistaminic compositions and methods containing pyridine derivatives |
| US4584382A (en) * | 1983-02-01 | 1986-04-22 | Findlay John W A | Pyridyl acrylate compound |
| US4639459A (en) * | 1983-02-01 | 1987-01-27 | Burroughs Wellcome Co. | Use of trifluoromethyl compounds |
| US4564685A (en) * | 1983-03-10 | 1986-01-14 | Findlay John W A | Diphenylmethane compounds |
| US4621094A (en) * | 1983-03-10 | 1986-11-04 | Findlay John W A | Anti-histaminic pyridyl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| BE514068A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1952-09-30 |
| CH308141A (fr) | 1955-06-30 |
| NL84175C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1957-02-15 |
| FR1080465A (fr) | 1954-12-09 |
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