GB1061639A - Pyrrole derivatives - Google Patents

Pyrrole derivatives

Info

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
Application number
GB2902565A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of GB1061639A publication Critical patent/GB1061639A/en
Expired legal-status Critical Current

Links

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

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.
GB2902565A 1963-07-26 1965-07-08 Pyrrole derivatives Expired GB1061639A (en)

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) FR90359E (en)
GB (1) GB1061639A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
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

Cited By (7)

* Cited by examiner, † Cited by third party
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
FR141F (en)
FR90359E (en) 1968-02-14

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