GB1195628A - Aroyl-Substituted Pyrroles - Google Patents
Aroyl-Substituted PyrrolesInfo
- Publication number
- GB1195628A GB1195628A GB3527768A GB3527768A GB1195628A GB 1195628 A GB1195628 A GB 1195628A GB 3527768 A GB3527768 A GB 3527768A GB 3527768 A GB3527768 A GB 3527768A GB 1195628 A GB1195628 A GB 1195628A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lower alkyl
- pyrrole
- formula
- acid
- cooh
- 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.)
- Expired
Links
- 150000003233 pyrroles Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 20
- 239000002253 acid Chemical class 0.000 abstract 14
- 150000001875 compounds Chemical class 0.000 abstract 12
- -1 monosubstituted phenyl Chemical group 0.000 abstract 10
- 230000007062 hydrolysis Effects 0.000 abstract 8
- 238000006460 hydrolysis reaction Methods 0.000 abstract 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 150000007513 acids Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000003973 alkyl amines Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000007517 lewis acids Chemical class 0.000 abstract 2
- 150000002923 oximes Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- LFWGWEFPIXJCOV-UHFFFAOYSA-N 1-(1-benzylpyrrol-2-yl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CN1CC1=CC=CC=C1 LFWGWEFPIXJCOV-UHFFFAOYSA-N 0.000 abstract 1
- GVUHUYQEAGMUNJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CN1 GVUHUYQEAGMUNJ-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- IMYGTWMJKVNQNY-UHFFFAOYSA-N 3-(1h-pyrrol-2-yl)prop-2-enoic acid Chemical class OC(=O)C=CC1=CC=CN1 IMYGTWMJKVNQNY-UHFFFAOYSA-N 0.000 abstract 1
- XDNDSAQVXNZKGP-UHFFFAOYSA-N 3-(1h-pyrrol-2-yl)propanoic acid Chemical class OC(=O)CCC1=CC=CN1 XDNDSAQVXNZKGP-UHFFFAOYSA-N 0.000 abstract 1
- 241001502050 Acis Species 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001447 alkali salts Chemical class 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 125000004802 cyanophenyl group Chemical group 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- ZSANYRMTSBBUCA-UHFFFAOYSA-N diethyl 3-oxopentanedioate Chemical compound CCOC(=O)CC(=O)CC(=O)OCC ZSANYRMTSBBUCA-UHFFFAOYSA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- BYXVWIJUIQYESP-UHFFFAOYSA-N ethyl 2-(1-methylpyrrol-2-yl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=CN1C BYXVWIJUIQYESP-UHFFFAOYSA-N 0.000 abstract 1
- LCFHAQAPRWNYAX-UHFFFAOYSA-N ethyl 2-(2,4-dimethyl-1h-pyrrol-3-yl)acetate Chemical class CCOC(=O)CC=1C(C)=CNC=1C LCFHAQAPRWNYAX-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- CGYVDYLHQYNGFC-UHFFFAOYSA-N methyl 2-(1-methylpyrrol-2-yl)acetate Chemical compound COC(=O)CC1=CC=CN1C CGYVDYLHQYNGFC-UHFFFAOYSA-N 0.000 abstract 1
- JIPKLZVKWCJYEX-UHFFFAOYSA-N methyl 2-(1h-pyrrol-2-yl)acetate Chemical compound COC(=O)CC1=CC=CN1 JIPKLZVKWCJYEX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical class O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65607467A | 1967-07-26 | 1967-07-26 | |
| US74134868A | 1968-07-01 | 1968-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1195628A true GB1195628A (en) | 1970-06-17 |
Family
ID=27097103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3527768A Expired GB1195628A (en) | 1967-07-26 | 1968-07-24 | Aroyl-Substituted Pyrroles |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT289096B (enrdf_load_stackoverflow) |
| BE (1) | BE718594A (enrdf_load_stackoverflow) |
| CH (1) | CH518929A (enrdf_load_stackoverflow) |
| DK (1) | DK136059B (enrdf_load_stackoverflow) |
| ES (1) | ES356485A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1574570A (enrdf_load_stackoverflow) |
| GB (1) | GB1195628A (enrdf_load_stackoverflow) |
| IL (1) | IL30426A (enrdf_load_stackoverflow) |
| NL (1) | NL162638C (enrdf_load_stackoverflow) |
| SE (1) | SE338993B (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1983001774A1 (en) * | 1981-11-23 | 1983-05-26 | Riker Laboratories Inc | Substituted pyrrole |
| US4396626A (en) | 1980-10-09 | 1983-08-02 | Beecham Group Limited | Cyclic compounds and their use |
| FR2522324A1 (fr) * | 1982-02-26 | 1983-09-02 | Sigma Tau Ind Farmaceuti | Pyrrole-acetamides, leur procede de preparation et composition therapeutique les contenant |
| EP0115424A1 (en) * | 1983-01-26 | 1984-08-08 | McNeilab, Inc. | Pyrrole-2-acetylamino acid derivatives |
| WO1996010013A1 (en) * | 1994-09-27 | 1996-04-04 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| US7544711B2 (en) | 1996-09-04 | 2009-06-09 | Nicox S.A. | Use of nitroderivatives in urinary incontinence |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2068425B1 (enrdf_load_stackoverflow) * | 1969-11-12 | 1973-01-12 | Roussel Uclaf | |
| FR2128205B1 (enrdf_load_stackoverflow) * | 1971-03-11 | 1974-05-24 | Roussel Uclaf | |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| DE3026402A1 (de) * | 1980-07-11 | 1982-02-04 | Syntex Corp., Palo Alto, Calif. | Die verwendung analgetischer und nicht-hormonaler, entzuendungshemmender mittel bei der behandlung von mikrovaskulaeren erkrankungen |
| IT1308633B1 (it) | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
| AU2004210082B2 (en) * | 2003-02-06 | 2011-03-17 | Dompe' Farmaceutici S.P.A. | 2-aryl-acetic acids, their derivatives and pharmaceutical compositions containing them |
-
1968
- 1968-07-24 ES ES356485A patent/ES356485A1/es not_active Expired
- 1968-07-24 SE SE1007068A patent/SE338993B/xx unknown
- 1968-07-24 GB GB3527768A patent/GB1195628A/en not_active Expired
- 1968-07-25 BE BE718594D patent/BE718594A/xx not_active IP Right Cessation
- 1968-07-25 CH CH1116368A patent/CH518929A/de not_active IP Right Cessation
- 1968-07-25 FR FR1574570D patent/FR1574570A/fr not_active Expired
- 1968-07-25 IL IL3042668A patent/IL30426A/en unknown
- 1968-07-26 AT AT730768A patent/AT289096B/de not_active IP Right Cessation
- 1968-07-26 DK DK361168A patent/DK136059B/da not_active IP Right Cessation
- 1968-07-26 NL NL6810664A patent/NL162638C/xx not_active IP Right Cessation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4396626A (en) | 1980-10-09 | 1983-08-02 | Beecham Group Limited | Cyclic compounds and their use |
| WO1983001774A1 (en) * | 1981-11-23 | 1983-05-26 | Riker Laboratories Inc | Substituted pyrrole |
| US4418074A (en) | 1981-11-23 | 1983-11-29 | Riker Laboratories, Inc. | 2,6 Di(t-butyl)-4-(2'-pyrrol)-phenol and anti-inflammatory use thereof |
| FR2522324A1 (fr) * | 1982-02-26 | 1983-09-02 | Sigma Tau Ind Farmaceuti | Pyrrole-acetamides, leur procede de preparation et composition therapeutique les contenant |
| EP0115424A1 (en) * | 1983-01-26 | 1984-08-08 | McNeilab, Inc. | Pyrrole-2-acetylamino acid derivatives |
| WO1996010013A1 (en) * | 1994-09-27 | 1996-04-04 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| US7544711B2 (en) | 1996-09-04 | 2009-06-09 | Nicox S.A. | Use of nitroderivatives in urinary incontinence |
Also Published As
| Publication number | Publication date |
|---|---|
| SE338993B (enrdf_load_stackoverflow) | 1971-09-27 |
| NL162638C (nl) | 1980-06-16 |
| NL162638B (nl) | 1980-01-15 |
| IL30426A (en) | 1972-02-29 |
| CH518929A (de) | 1972-02-15 |
| AT289096B (de) | 1971-04-13 |
| DE1770984A1 (de) | 1972-04-06 |
| DK136059B (da) | 1977-08-08 |
| NL6810664A (enrdf_load_stackoverflow) | 1969-01-28 |
| ES356485A1 (es) | 1970-01-16 |
| BE718594A (enrdf_load_stackoverflow) | 1969-01-27 |
| DE1770984B2 (de) | 1975-05-22 |
| DK136059C (enrdf_load_stackoverflow) | 1978-01-09 |
| FR1574570A (enrdf_load_stackoverflow) | 1969-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |