GB1061639A - Pyrrole derivatives - Google Patents
Pyrrole derivativesInfo
- Publication number
- GB1061639A GB1061639A GB2902565A GB2902565A GB1061639A GB 1061639 A GB1061639 A GB 1061639A GB 2902565 A GB2902565 A GB 2902565A GB 2902565 A GB2902565 A GB 2902565A GB 1061639 A GB1061639 A GB 1061639A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- methyl
- formula
- nitropyrrole
- compound
- 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 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- GEGNYFQOFWUIFG-UHFFFAOYSA-N 1-methyl-4-nitro-1h-pyrrole-2-carboxylic acid Chemical compound CN1C=C([N+]([O-])=O)C=C1C(O)=O GEGNYFQOFWUIFG-UHFFFAOYSA-N 0.000 abstract 1
- ZBXBOVMIODZOBQ-UHFFFAOYSA-N 1-methyl-4-nitropyrrole-2-carbonyl chloride Chemical compound CN1C=C([N+]([O-])=O)C=C1C(Cl)=O ZBXBOVMIODZOBQ-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
- ZGBAXLDWBCJVGN-UHFFFAOYSA-N 3-nitro-1H-pyrrole-2-carboximidamide hydrochloride Chemical compound Cl.[N+](=O)([O-])C1=C(NC=C1)C(=N)N ZGBAXLDWBCJVGN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 230000022244 formylation Effects 0.000 abstract 1
- 238000006170 formylation reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 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
-
- 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
- C07D207/42—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of formula <FORM:1061639/C2/1> wherein n is 2 or 3 and X is a p-phenylene group or a group -(CH2)ywherein y is 1, 3, 4, 5, or 6, or n is 4, 5, or 6, and X is a p-phenylene group or a group -(CH2)y-, wherein y is 1, 2, 3, 4, 5 or 6, and R is a hydrogen atom or a formyl group, non-toxic acid addition salts thereof, and their preparation by reaction of a compound of formula <FORM:1061639/C2/2> under anhydrous conditions with a C1- 4 aliphati alcohol and hydrogen chloride to form a compound of formula <FORM:1061639/C2/3> reacting this under anhydrous conditions with ammonia in a C1- 4 aliphatic alcohol to form the corresponding nitro-pyrrole amidine hydrochloride, and catalytically hydrogenating the nitro group to an amino group, followed, if desired, by formylation. Nitrile starting materials of the second formula above are prepared by reaction of 1-methyl-4-nitropyrrole-2-carboxylic acid with thionyl chloride and then with a compound H2N-X-CN to form a 1-methyl-4-nitropyrrole-2-carboxamido-alkyl-or-benzo-nitrile, catalytically hydrogenating this to form a 1-methyl-4-aminopyrrole-2-carboxamido-alkyl- or benzo-nitrile, and condensing this with 1-methyl-4-nitropyrrole-2-carboxylic acid chloride, followed, if desired, by the requisite number of successive catalytic hydrogenations and condensations with the above acid chloride. The compounds of the invention have anti-viral, anti-protozoal and anthelmintic activity and may be used in pharmaceutical compositions in combination with a carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1570163 | 1963-07-26 | ||
| IT1539064 | 1964-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1061639A true GB1061639A (en) | 1967-03-15 |
Family
ID=26326790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2902565A Expired GB1061639A (en) | 1963-07-26 | 1965-07-08 | Pyrrole derivatives |
Country Status (2)
| Country | Link |
|---|---|
| FR (2) | FR141F (en) |
| GB (1) | GB1061639A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4738980A (en) * | 1985-07-16 | 1988-04-19 | Farmitalia Carlo Erba, S.P.A. | Distamycin derivatives and process for their preparation |
| US4766142A (en) * | 1985-07-16 | 1988-08-23 | Farmitalia Carlo Erba S.R.L. | Poly-4-aminopyrrole-2-carboxamido derivatives and their use as antiuiral or antitumor agents |
| US5017599A (en) * | 1986-05-20 | 1991-05-21 | Farmitalia Carlo Erba, Spa | Site specific alkylating agents |
| US5049579A (en) * | 1986-05-20 | 1991-09-17 | Farmitalia Carlo Erba, S.R.L. | Site specific alkylating agents |
| US5175182A (en) * | 1989-03-23 | 1992-12-29 | Farmitalia Carlo Erba Srl | Acryloyl substituted pyrrole derivatives |
| GB2260134A (en) * | 1991-10-04 | 1993-04-07 | Erba Carlo Spa | Derivatives of poly-5-amino-3-carboxy-1-methyl compounds |
| US5310752A (en) * | 1986-05-20 | 1994-05-10 | Farmitalia Carlo Erba Spa | Site specific alkylating agents |
-
0
- FR FR90359D patent/FR90359E/fr not_active Expired
- FR FR141D patent/FR141F/fr active Active
-
1965
- 1965-07-08 GB GB2902565A patent/GB1061639A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4738980A (en) * | 1985-07-16 | 1988-04-19 | Farmitalia Carlo Erba, S.P.A. | Distamycin derivatives and process for their preparation |
| US4766142A (en) * | 1985-07-16 | 1988-08-23 | Farmitalia Carlo Erba S.R.L. | Poly-4-aminopyrrole-2-carboxamido derivatives and their use as antiuiral or antitumor agents |
| US5017599A (en) * | 1986-05-20 | 1991-05-21 | Farmitalia Carlo Erba, Spa | Site specific alkylating agents |
| US5049579A (en) * | 1986-05-20 | 1991-09-17 | Farmitalia Carlo Erba, S.R.L. | Site specific alkylating agents |
| US5310752A (en) * | 1986-05-20 | 1994-05-10 | Farmitalia Carlo Erba Spa | Site specific alkylating agents |
| US5175182A (en) * | 1989-03-23 | 1992-12-29 | Farmitalia Carlo Erba Srl | Acryloyl substituted pyrrole derivatives |
| GB2260134A (en) * | 1991-10-04 | 1993-04-07 | Erba Carlo Spa | Derivatives of poly-5-amino-3-carboxy-1-methyl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR90359E (en) | 1968-02-14 |
| FR141F (en) |
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