BE514068A - - Google Patents
Info
- Publication number
- BE514068A BE514068A BE514068DA BE514068A BE 514068 A BE514068 A BE 514068A BE 514068D A BE514068D A BE 514068DA BE 514068 A BE514068 A BE 514068A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- millimicrons
- compound
- absorption
- sulfuric acid
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 22
- 239000000155 melt Substances 0.000 claims description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000000926 separation method Methods 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
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 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 22
- 230000031700 light absorption Effects 0.000 description 14
- 230000008569 process Effects 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 150000003891 oxalate salts Chemical class 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000004076 pyridyl group Chemical class 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- YZBVIYJNUQVTTQ-UHFFFAOYSA-N 1-prop-2-enylpyrrolidine Chemical compound C=CCN1CCCC1 YZBVIYJNUQVTTQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- -1 dimethylamino, pyrrolidino group Chemical group 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KYZUPGAUPFMUNE-UHFFFAOYSA-N 1-(2-methylphenyl)-1-pyridin-2-yl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound CC1=CC=CC=C1C(O)(C=1N=CC=CC=1)CCN1CCCC1 KYZUPGAUPFMUNE-UHFFFAOYSA-N 0.000 description 1
- WVMGNUZRSDZOTK-UHFFFAOYSA-N 1-(4-ethylphenyl)-1-pyridin-2-yl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound C(C)C1=CC=C(C=C1)C(CCN1CCCC1)(O)C1=NC=CC=C1 WVMGNUZRSDZOTK-UHFFFAOYSA-N 0.000 description 1
- KORJOGPPKPWOLT-UHFFFAOYSA-N 1-prop-1-enylpyrrolidine Chemical compound CC=CN1CCCC1 KORJOGPPKPWOLT-UHFFFAOYSA-N 0.000 description 1
- OBUPVPZCSVEBQN-UHFFFAOYSA-N 1-pyridin-2-ylpropan-1-ol Chemical compound CCC(O)C1=CC=CC=N1 OBUPVPZCSVEBQN-UHFFFAOYSA-N 0.000 description 1
- WOXAJEQDQZMIPR-UHFFFAOYSA-N 2-[1-(2-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine Chemical class CC1=C(C=CC=C1)C(=CCN1CCCC1)C1=NC=CC=C1 WOXAJEQDQZMIPR-UHFFFAOYSA-N 0.000 description 1
- HBOKHKUQVIUURV-UHFFFAOYSA-N 2-[1-(4-methylphenyl)-3-piperidin-1-ylprop-1-enyl]pyridine Chemical class CC1=CC=C(C=C1)C(=CCN1CCCCC1)C1=NC=CC=C1 HBOKHKUQVIUURV-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 238000009489 vacuum treatment Methods 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 |
|---|---|
| BE514068A true BE514068A (en:Method) | 1952-09-30 |
Family
ID=26673905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE514068D BE514068A (en:Method) | 1951-09-10 | 1952-09-09 |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE514068A (en:Method) |
| CH (1) | CH308141A (en:Method) |
| DE (1) | DE1227464B (en:Method) |
| FR (1) | FR1080465A (en:Method) |
| NL (1) | NL84175C (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124585A (en) * | 1964-03-10 | Z-pymibyl | ||
| SI8310221A8 (en) * | 1982-02-04 | 1995-10-31 | Wellcome Found | Process for obtaining new pyridil 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 |
| US4639459A (en) * | 1983-02-01 | 1987-01-27 | Burroughs Wellcome Co. | Use of trifluoromethyl compounds |
| US4584382A (en) * | 1983-02-01 | 1986-04-22 | Findlay John W A | Pyridyl acrylate compound |
| 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 |
-
1952
- 1952-09-08 DE DEW9428A patent/DE1227464B/de active Pending
- 1952-09-09 CH CH308141D patent/CH308141A/fr unknown
- 1952-09-09 BE BE514068D patent/BE514068A/fr unknown
- 1952-09-09 NL NL172357A patent/NL84175C/nl active
- 1952-09-09 FR FR1080465D patent/FR1080465A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH308141A (fr) | 1955-06-30 |
| NL84175C (en:Method) | 1957-02-15 |
| DE1227464B (de) | 1966-10-27 |
| FR1080465A (fr) | 1954-12-09 |
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