CH533619A - Verfahren zur Herstellung von Pyrrolderivaten - Google Patents
Verfahren zur Herstellung von PyrrolderivatenInfo
- Publication number
- CH533619A CH533619A CH1373470A CH1373470A CH533619A CH 533619 A CH533619 A CH 533619A CH 1373470 A CH1373470 A CH 1373470A CH 1373470 A CH1373470 A CH 1373470A CH 533619 A CH533619 A CH 533619A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrrole
- lower alkyl
- acid
- bis
- methyl
- Prior art date
Links
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title abstract description 10
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 7
- 150000003233 pyrroles Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- -1 alkyl halogen Chemical class 0.000 abstract description 9
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JVOBPDIVTVIVKO-UHFFFAOYSA-N CC1=CC(=C(N1)C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C Chemical compound CC1=CC(=C(N1)C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C JVOBPDIVTVIVKO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OMJRXJFRYQJYHA-UHFFFAOYSA-N 1-[2-methyl-4,5-bis(4-methylphenyl)-1H-pyrrol-3-yl]ethanone Chemical compound CC1=C(C(=C(N1)C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C(C)=O OMJRXJFRYQJYHA-UHFFFAOYSA-N 0.000 description 1
- XPFYMFMMSNQKQC-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 XPFYMFMMSNQKQC-UHFFFAOYSA-N 0.000 description 1
- TYHYPWIXMCAVMD-UHFFFAOYSA-N 2,3-bis(4-chlorophenyl)-5-methyl-1H-pyrrole Chemical compound CC=1NC(=C(C1)C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl TYHYPWIXMCAVMD-UHFFFAOYSA-N 0.000 description 1
- WGVQZBURQZKDBN-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-1h-pyrrole Chemical group C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC=C1 WGVQZBURQZKDBN-UHFFFAOYSA-N 0.000 description 1
- WABWKXZHYGHSCI-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-5-methyl-1h-pyrrole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C)=C1 WABWKXZHYGHSCI-UHFFFAOYSA-N 0.000 description 1
- LAZYZKCHBCUTPQ-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-5-propyl-1H-pyrrole Chemical compound C(CC)C=1NC(=C(C1)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC LAZYZKCHBCUTPQ-UHFFFAOYSA-N 0.000 description 1
- BSJURRCNZZFQBW-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-pyrrole Chemical compound C1=CC(Cl)=CC=C1C1=CC=CN1 BSJURRCNZZFQBW-UHFFFAOYSA-N 0.000 description 1
- UTZMQFUWBQCYQR-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(4-methoxyphenyl)-5-methyl-1H-pyrrole Chemical compound CC1=CC(=C(N1)C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)OC UTZMQFUWBQCYQR-UHFFFAOYSA-N 0.000 description 1
- LRMKNDMDNZWNPB-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1h-pyrrole Chemical compound C1=CC(OC)=CC=C1C1=CC=CN1 LRMKNDMDNZWNPB-UHFFFAOYSA-N 0.000 description 1
- OLBYFEGTUWWPTR-UHFFFAOYSA-N 2-hydroxyimino-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(=NO)C(=O)C1=CC=CC=C1 OLBYFEGTUWWPTR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- SGYZRXDPUYQURP-UHFFFAOYSA-N 5-ethyl-2,3-bis(4-methoxyphenyl)-1H-pyrrole Chemical compound C(C)C=1NC(=C(C1)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC SGYZRXDPUYQURP-UHFFFAOYSA-N 0.000 description 1
- IJZPUNJYBSHEJK-UHFFFAOYSA-N 5-methyl-2,3-diphenyl-1h-pyrrole Chemical group N1C(C)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IJZPUNJYBSHEJK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XHZSXUHYLPFZGN-UHFFFAOYSA-N CC1=CC(=C(N1)C1=CC=C(C=C1)C)C1=CC=C(C=C1)C Chemical compound CC1=CC(=C(N1)C1=CC=C(C=C1)C)C1=CC=C(C=C1)C XHZSXUHYLPFZGN-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44073349A JPS4843117B1 (enrdf_load_html_response) | 1969-09-16 | 1969-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH533619A true CH533619A (de) | 1973-02-15 |
Family
ID=13515581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1373470A CH533619A (de) | 1969-09-16 | 1970-09-16 | Verfahren zur Herstellung von Pyrrolderivaten |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4843117B1 (enrdf_load_html_response) |
| AT (1) | AT295512B (enrdf_load_html_response) |
| CH (1) | CH533619A (enrdf_load_html_response) |
| ES (1) | ES383467A1 (enrdf_load_html_response) |
| NL (1) | NL7013607A (enrdf_load_html_response) |
| OA (1) | OA03484A (enrdf_load_html_response) |
| SE (1) | SE367191B (enrdf_load_html_response) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335136A (en) * | 1980-04-18 | 1982-06-15 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 4,5-diaryl-α-(polyfluoroalkyl)-1H-pyrrole-2-methanamines |
| US4318917A (en) * | 1981-01-21 | 1982-03-09 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2,3-diaryl-5-[2,2,2-trifluoro-1-(trifluoromethyl]ethyl-1H-pyrroles |
| JPS5769221U (enrdf_load_html_response) * | 1980-10-15 | 1982-04-26 | ||
| JPS61117231U (enrdf_load_html_response) * | 1984-12-29 | 1986-07-24 |
-
1969
- 1969-09-16 JP JP44073349A patent/JPS4843117B1/ja active Pending
-
1970
- 1970-09-08 ES ES383467A patent/ES383467A1/es not_active Expired
- 1970-09-08 AT AT812670A patent/AT295512B/de not_active IP Right Cessation
- 1970-09-10 OA OA54030A patent/OA03484A/xx unknown
- 1970-09-11 SE SE12356/70A patent/SE367191B/xx unknown
- 1970-09-15 NL NL7013607A patent/NL7013607A/xx unknown
- 1970-09-16 CH CH1373470A patent/CH533619A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT295512B (de) | 1972-01-10 |
| OA03484A (fr) | 1971-03-30 |
| JPS4843117B1 (enrdf_load_html_response) | 1973-12-17 |
| SE367191B (enrdf_load_html_response) | 1974-05-20 |
| ES383467A1 (es) | 1973-02-16 |
| NL7013607A (enrdf_load_html_response) | 1971-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |