ES429446A1 - Aminopyrrole derivatives - Google Patents
Aminopyrrole derivativesInfo
- Publication number
- ES429446A1 ES429446A1 ES429446A ES429446A ES429446A1 ES 429446 A1 ES429446 A1 ES 429446A1 ES 429446 A ES429446 A ES 429446A ES 429446 A ES429446 A ES 429446A ES 429446 A1 ES429446 A1 ES 429446A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- group
- see formula
- temperature
- 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
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical class NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- -1 p-benzyloxyphenyl Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- UDSNIGGFYHWMEH-UHFFFAOYSA-N 3-amino-2h-pyran-2-ol Chemical class NC1=CC=COC1O UDSNIGGFYHWMEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D207/34—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D207/34—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Abstract
Procedure for preparing aminopyrol derivatives, of the following general formula: **(See formula)** and its pharmaceutically acceptable acid salts, in which it represents hydrogen, (C1-4) alkyl, phenyl, o-(C1-4) alkyl phenyl, m-C1-4 alkyl phenyl, p-C1-4 alkyl. phenyl, p-halogenophenyl, p-C1-4 alkoxy phenyl or p-benzyloxyphenyl; R2 and R3 represent hydrogen; R4 represents (C2-4) aliphatic acyl, benzoyl, p-(C2-4) alkoxy benzoyl, p-halogenobenzoyl, carbalkoxy (C1-4), carbamyl, methylcarbamyl or phenylcarbamyl; R5 is chosen from the group consisting of hydrogen, (C1-4) alkyl, (C1-4) carbalkoxy, [C1-4) carbalkoxy] methyl and trifluoromethyl; Taken together, R4 and R5 may also represent the group -CO- (CH2) 3- and in which the carbonyl group is connected to the carbon atom of the pyrrole ring bearing the R4 substituent; on the condition that, when R1 and R5 simultaneously represent methyl, R4 cannot be carbetoxyl; characterized in that substantially equimolar amounts of an alpha-aminonitrile of the general formula are reacted: **(See formula)** or an acid addition salt thereof, wherein R1 has the same meanings as indicated above, and of a compound of the general formula: **(See formula)** where R4 and R5 have the same meanings as indicated in claim 1, and X represents the groups, (see formula) or (see formula) where the -CH2 part is linked to the substituent R4, in an organic solvent chosen from the group consisting of benzene, tetrahydrofuran and alkanols (C1-4), in the presence of an acid catalyst for 1 to 28 hours at a temperature comprised between room temperature and reflux temperature of the reaction mixture, subsequently add a basic condensing agent chosen from the group consisting of alkali and alkaline earth metal amides, hydroxides, alkoxides, carbonates and hydrides, and maintain the reaction mixture thus obtained, for 1 to 30 hours at a temperature between room temperature and the boiling temperature of the reaction mixture. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3979073A GB1427945A (en) | 1973-08-22 | 1973-08-22 | Aminopyrrole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES429446A1 true ES429446A1 (en) | 1977-02-16 |
Family
ID=10411528
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES429446A Expired ES429446A1 (en) | 1973-08-22 | 1974-08-22 | Aminopyrrole derivatives |
| ES449425A Expired ES449425A1 (en) | 1973-08-22 | 1976-07-01 | Aminopyrrole derivatives |
| ES449426A Expired ES449426A1 (en) | 1973-08-22 | 1976-07-01 | Aminopyrrole derivatives |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES449425A Expired ES449425A1 (en) | 1973-08-22 | 1976-07-01 | Aminopyrrole derivatives |
| ES449426A Expired ES449426A1 (en) | 1973-08-22 | 1976-07-01 | Aminopyrrole derivatives |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5328914B2 (en) |
| AR (3) | AR210246A1 (en) |
| AT (1) | AT336600B (en) |
| BE (1) | BE819088A (en) |
| CA (1) | CA1050556A (en) |
| CH (1) | CH605741A5 (en) |
| CS (1) | CS188201B2 (en) |
| DD (1) | DD113756A5 (en) |
| DE (4) | DE2439284C2 (en) |
| DK (1) | DK156391C (en) |
| ES (3) | ES429446A1 (en) |
| FI (1) | FI61879C (en) |
| FR (1) | FR2241308B1 (en) |
| GB (1) | GB1427945A (en) |
| HU (1) | HU169728B (en) |
| IE (1) | IE40290B1 (en) |
| IL (1) | IL45368A (en) |
| IN (1) | IN140329B (en) |
| LU (1) | LU70764A1 (en) |
| NL (1) | NL7411092A (en) |
| NO (1) | NO143845C (en) |
| PL (2) | PL96806B1 (en) |
| RO (3) | RO70535A (en) |
| SE (1) | SE394429B (en) |
| SU (1) | SU843738A3 (en) |
| YU (1) | YU36926B (en) |
| ZA (1) | ZA744754B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1492663A (en) * | 1975-02-20 | 1977-11-23 | Lepetit Spa | 4-amino-3-pyrrole carboxamides |
| GB1548398A (en) * | 1975-06-05 | 1979-07-11 | Lilly Industries Ltd | Acylamino pyrroles furans and thiophenes |
| DE3212591A1 (en) * | 1982-04-03 | 1983-10-13 | Gödecke AG, 1000 Berlin | 2-PYRROLIN-3-CARBONITRIL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THE SAME |
| JPH0216740U (en) * | 1988-07-21 | 1990-02-02 | ||
| DE59009489D1 (en) * | 1989-03-28 | 1995-09-14 | Ciba Geigy Ag | Substituted aminopyrroles as stabilizers, chlorine-containing polymers. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1148908A (en) * | 1965-04-19 | 1969-04-16 | Sumitomo Chemical Co | Indole derivatives and processes for making them |
| GB1187903A (en) * | 1967-09-29 | 1970-04-15 | Sumitomo Chemical Co | Glucuronides of 3-Indolylaliphatic Acid Derivatives and Processes for Producing them |
-
1973
- 1973-08-22 GB GB3979073A patent/GB1427945A/en not_active Expired
-
1974
- 1974-07-27 ZA ZA00744754A patent/ZA744754B/en unknown
- 1974-07-29 IL IL45368A patent/IL45368A/en unknown
- 1974-08-01 YU YU2141/74A patent/YU36926B/en unknown
- 1974-08-08 NO NO742862A patent/NO143845C/en unknown
- 1974-08-08 IE IE1672/74A patent/IE40290B1/en unknown
- 1974-08-16 DE DE2439284A patent/DE2439284C2/en not_active Expired
- 1974-08-16 DD DD180545A patent/DD113756A5/xx unknown
- 1974-08-16 DE DE2462967A patent/DE2462967C2/en not_active Expired
- 1974-08-16 DE DE2462966A patent/DE2462966C2/en not_active Expired
- 1974-08-16 DE DE2462963A patent/DE2462963C2/en not_active Expired
- 1974-08-19 RO RO7491735A patent/RO70535A/en unknown
- 1974-08-19 RO RO79830A patent/RO72882B/en unknown
- 1974-08-19 RO RO7491734A patent/RO70534A/en unknown
- 1974-08-20 LU LU70764A patent/LU70764A1/xx unknown
- 1974-08-20 IN IN1864/CAL/1974A patent/IN140329B/en unknown
- 1974-08-20 NL NL7411092A patent/NL7411092A/en unknown
- 1974-08-21 CA CA207,472A patent/CA1050556A/en not_active Expired
- 1974-08-21 CH CH1142674A patent/CH605741A5/xx not_active IP Right Cessation
- 1974-08-21 SE SE7410636A patent/SE394429B/en not_active IP Right Cessation
- 1974-08-21 DK DK445974A patent/DK156391C/en active
- 1974-08-21 SU SU742055571A patent/SU843738A3/en active
- 1974-08-21 HU HULE754A patent/HU169728B/hu not_active IP Right Cessation
- 1974-08-21 JP JP9600974A patent/JPS5328914B2/ja not_active Expired
- 1974-08-21 FI FI2462/74A patent/FI61879C/en active
- 1974-08-22 AT AT684774A patent/AT336600B/en not_active IP Right Cessation
- 1974-08-22 PL PL1974189700A patent/PL96806B1/en unknown
- 1974-08-22 ES ES429446A patent/ES429446A1/en not_active Expired
- 1974-08-22 PL PL1974173617A patent/PL95235B1/pl unknown
- 1974-08-22 CS CS745833A patent/CS188201B2/en unknown
- 1974-08-22 BE BE147818A patent/BE819088A/en not_active IP Right Cessation
- 1974-08-22 FR FR7428894A patent/FR2241308B1/fr not_active Expired
- 1974-08-27 AR AR255253A patent/AR210246A1/en active
-
1976
- 1976-06-03 AR AR263502A patent/AR210132A1/en active
- 1976-06-03 AR AR263503A patent/AR210133A1/en active
- 1976-07-01 ES ES449425A patent/ES449425A1/en not_active Expired
- 1976-07-01 ES ES449426A patent/ES449426A1/en not_active Expired
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