FI77023C - Foerfarande foer framstaellning av 1-alkyl- eller 1,4-dialkyl-1h-pyrrol-2-aettiksyraestrar. - Google Patents
Foerfarande foer framstaellning av 1-alkyl- eller 1,4-dialkyl-1h-pyrrol-2-aettiksyraestrar. Download PDFInfo
- Publication number
- FI77023C FI77023C FI832262A FI832262A FI77023C FI 77023 C FI77023 C FI 77023C FI 832262 A FI832262 A FI 832262A FI 832262 A FI832262 A FI 832262A FI 77023 C FI77023 C FI 77023C
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- general formula
- dialkyl
- pyrrole
- acetic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- AFMGAYVTENHETH-UHFFFAOYSA-N N=1C(C=CC=1)CC(=O)O Chemical class N=1C(C=CC=1)CC(=O)O AFMGAYVTENHETH-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 150000005690 diesters Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GVUHUYQEAGMUNJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CN1 GVUHUYQEAGMUNJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- BRYSLWVZCAFHIZ-UHFFFAOYSA-N 2-[1-(4-methylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)N1C(CC(O)=O)=CC=C1 BRYSLWVZCAFHIZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- -1 diester compound Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- OORBYQVSQSXKRG-UHFFFAOYSA-N ethyl 2-(1-methylpyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC=CN1C OORBYQVSQSXKRG-UHFFFAOYSA-N 0.000 description 1
- YWLMDVDPKZKLNL-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1,4-dimethylpyrrole-3-carboxylate Chemical compound CCOC(=O)CC1=C(C(=O)OCC)C(C)=CN1C YWLMDVDPKZKLNL-UHFFFAOYSA-N 0.000 description 1
- WIDHUKOADYLKIO-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1-methylpyrrole-3-carboxylate Chemical compound CCOC(=O)CC1=C(C(=O)OCC)C=CN1C WIDHUKOADYLKIO-UHFFFAOYSA-N 0.000 description 1
- ZAWLAWMGFLGCFR-UHFFFAOYSA-N ethyl 2-(4,5-dimethyl-1h-pyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC(C)=C(C)N1 ZAWLAWMGFLGCFR-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
- 229960003414 zomepirac Drugs 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
- C07D207/33—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
- C07D207/337—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)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU201382 | 1982-06-22 | ||
| HU822013A HU187137B (en) | 1982-06-22 | 1982-06-22 | Process for producing esters of 1-alkyl- orl,4-dialkyl-1h-pyrrol-acetic acid |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI832262A0 FI832262A0 (fi) | 1983-06-21 |
| FI832262L FI832262L (fi) | 1983-12-23 |
| FI77023B FI77023B (fi) | 1988-09-30 |
| FI77023C true FI77023C (fi) | 1989-01-10 |
Family
ID=10957298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI832262A FI77023C (fi) | 1982-06-22 | 1983-06-21 | Foerfarande foer framstaellning av 1-alkyl- eller 1,4-dialkyl-1h-pyrrol-2-aettiksyraestrar. |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS597162A (enrdf_load_stackoverflow) |
| AT (1) | AT377255B (enrdf_load_stackoverflow) |
| CA (1) | CA1188306A (enrdf_load_stackoverflow) |
| DK (1) | DK287183A (enrdf_load_stackoverflow) |
| ES (1) | ES523478A0 (enrdf_load_stackoverflow) |
| FI (1) | FI77023C (enrdf_load_stackoverflow) |
| HU (1) | HU187137B (enrdf_load_stackoverflow) |
| IN (1) | IN160016B (enrdf_load_stackoverflow) |
| SE (1) | SE454441B (enrdf_load_stackoverflow) |
| SU (1) | SU1179921A3 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987002662A2 (en) * | 1985-10-25 | 1987-05-07 | Sandoz Ag | Heterocyclic analogs of mevalonolactone and derivatives thereof, processes for their production and their use as pharmaceuticals |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
-
1982
- 1982-06-22 HU HU822013A patent/HU187137B/hu not_active IP Right Cessation
-
1983
- 1983-06-21 FI FI832262A patent/FI77023C/fi not_active IP Right Cessation
- 1983-06-21 ES ES523478A patent/ES523478A0/es active Granted
- 1983-06-21 CA CA000430840A patent/CA1188306A/en not_active Expired
- 1983-06-21 AT AT0228383A patent/AT377255B/de not_active IP Right Cessation
- 1983-06-21 IN IN422/DEL/83A patent/IN160016B/en unknown
- 1983-06-21 DK DK287183A patent/DK287183A/da not_active Application Discontinuation
- 1983-06-21 SE SE8303565A patent/SE454441B/sv not_active IP Right Cessation
- 1983-06-22 SU SU833611594A patent/SU1179921A3/ru active
- 1983-06-22 JP JP58111141A patent/JPS597162A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS597162A (ja) | 1984-01-14 |
| FI77023B (fi) | 1988-09-30 |
| SU1179921A3 (ru) | 1985-09-15 |
| SE8303565D0 (sv) | 1983-06-21 |
| ES8500227A1 (es) | 1984-10-01 |
| IN160016B (enrdf_load_stackoverflow) | 1987-06-20 |
| DK287183A (da) | 1983-12-23 |
| FI832262L (fi) | 1983-12-23 |
| HU187137B (en) | 1985-11-28 |
| JPH0136825B2 (enrdf_load_stackoverflow) | 1989-08-02 |
| AT377255B (de) | 1985-02-25 |
| ATA228383A (de) | 1984-07-15 |
| ES523478A0 (es) | 1984-10-01 |
| DK287183D0 (da) | 1983-06-21 |
| FI832262A0 (fi) | 1983-06-21 |
| SE8303565L (sv) | 1983-12-23 |
| CA1188306A (en) | 1985-06-04 |
| SE454441B (sv) | 1988-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYAR R.T. |