GB1348088A - Nitrofuran and nitrothiophene derivatives - Google Patents
Nitrofuran and nitrothiophene derivativesInfo
- Publication number
- GB1348088A GB1348088A GB4893772A GB4893772A GB1348088A GB 1348088 A GB1348088 A GB 1348088A GB 4893772 A GB4893772 A GB 4893772A GB 4893772 A GB4893772 A GB 4893772A GB 1348088 A GB1348088 A GB 1348088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- reacting
- nitro
- prepared
- formula
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1348088 Nitrofuran and nitrothiophene derivatives BOEHRINGER MANNHEIM GmbH 24 Oct 1972 [29 Oct 1971] 48937/72 Addition to 1318013 Heading C2C Novel compounds of Formula I (in which X is S or O, Het is atriazolopyridazine or thiadiazole system and R is an acylamino, acylaminoalkylamino, carbalkoxyalkylamino or cycloalkylamino radical or a piperidino or 1- piperazinyl radical substituted in the 4-position by a hydroxyl or hydroxyalkyl group) and pharmacologically acceptable acid addition salts thereof, are prepared by (a) reacting a compound of Formula II (in which R 1 is C 1-6 alkyl) or a salt thereof with a compound of Formula HR, or (b) condensing a compound of Formula III with a compound Z=CH-R (in which Z is O or S) or with a reactive derivative thereof, or (c) nitrating a compound of Formula IV and, if desired, converting a compound I obtained into a pharmalogically acceptable acid addition salt. The compounds I in which R is acylamino or cycloalkylamino can also be prepared by reacting a compound I in which R is NH 2 with an acylating or cycloalkylating agent. Starting materials of Formula II are prepared by reacting a compound III with appropriate ortho esters, or by reacting corresponding N- (C 1-6 acyl) derivatives of compounds III with trialkoxonium fluoborates. 3 - (5 - Nitro - 2 - furyl) - 5 - amino - 1,2,4- thiadiazole is prepared by reacting 5-nitro-2- furamidine hydrochloride with trichloromethylsulphenyl chloride to give 3-(5-nitro-2-furyl)-5- chloro-1,2,4-thiadiazole and reacting this with ammonia. 3 - (5 - Nitro - 2 - -furyl) - 6 - (aminomethyleneamino) - s - triazolo[4,3-b] - pyridazine is prepared by reacting 3-(5-nitro-2-furyl)-6-ethoxymethyleneamino - s - triazolo[4,3-b] - pyridazine with ammonia. 3 - (5 - Nitro - 2 - thienyl) - 6 - amino - striazolo[4,3-b]-pyridazine is prepared by reacting 5 - nitrothiophene - 2 - aldehyde with 3- hydrazino - 6 - chloropyridazine to give the corresponding hydrazone, cyclizing this to give 3 - (5 - nitro - 2 - thienyl) - 6 - chloro - s - triazolo- [4,3-b]pyridazine and aminating this by treating with potassium phthalimide followed by acidic fission to give the desired compound. Pharmaceutical compositions having antimicrobial activity, for oral or parenteral administration, comprise a compound I, or a pharmalogically acceptable acid addition salt thereof, together with a pharmaceutical carrier.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2153902A DE2153902A1 (en) | 1971-10-29 | 1971-10-29 | ANTIMICROBIALLY EFFECTIVE NITROFURA DERIVATIVES AND METHOD FOR PRODUCING THE SAME |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1348088A true GB1348088A (en) | 1974-03-13 |
Family
ID=5823698
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4893772A Expired GB1348088A (en) | 1971-10-29 | 1972-10-24 | Nitrofuran and nitrothiophene derivatives |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS4852769A (en) |
AR (3) | AR197008A1 (en) |
AT (5) | AT320628B (en) |
AU (1) | AU467712B2 (en) |
DD (1) | DD102387A5 (en) |
DE (1) | DE2153902A1 (en) |
ES (1) | ES407933A2 (en) |
FR (1) | FR2158313B2 (en) |
GB (1) | GB1348088A (en) |
HU (1) | HU164715B (en) |
IL (1) | IL40639A0 (en) |
NL (1) | NL7214621A (en) |
PL (1) | PL82632B1 (en) |
SU (2) | SU509235A3 (en) |
ZA (1) | ZA727504B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2222834A1 (en) * | 1972-05-10 | 1973-11-29 | Boehringer Mannheim Gmbh | NITROFURYL AMIDINE DERIVATIVES AND METHOD FOR PREPARING THE SAME |
MXPA05006478A (en) * | 2002-12-18 | 2005-09-08 | Vertex Pharma | Triazolopyridazines as protein kinases inhibitors. |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1527537A (en) * | 1966-06-18 | 1968-05-31 | Boehringer & Soehne Gmbh | Process for the preparation of new derivatives of 5-nitrofuran and 5-nitrothiophene |
-
1971
- 1971-10-29 DE DE2153902A patent/DE2153902A1/en active Pending
-
1972
- 1972-10-22 IL IL40639A patent/IL40639A0/en unknown
- 1972-10-23 ZA ZA727504A patent/ZA727504B/en unknown
- 1972-10-23 DD DD166425A patent/DD102387A5/xx unknown
- 1972-10-24 ES ES407933A patent/ES407933A2/en not_active Expired
- 1972-10-24 GB GB4893772A patent/GB1348088A/en not_active Expired
- 1972-10-25 AR AR244808A patent/AR197008A1/en active
- 1972-10-27 AT AT917072A patent/AT320628B/en not_active IP Right Cessation
- 1972-10-27 FR FR7238198A patent/FR2158313B2/fr not_active Expired
- 1972-10-27 AT AT61874*7A patent/AT327883B/en not_active IP Right Cessation
- 1972-10-27 AT AT61874*A patent/ATA61874A/en not_active IP Right Cessation
- 1972-10-27 AT AT61774*7A patent/AT327882B/en not_active IP Right Cessation
- 1972-10-27 AU AU48277/72A patent/AU467712B2/en not_active Expired
- 1972-10-27 NL NL7214621A patent/NL7214621A/xx unknown
- 1972-10-27 AT AT61774*A patent/ATA61774A/en not_active IP Right Cessation
- 1972-10-27 HU HUBO1401A patent/HU164715B/hu unknown
- 1972-10-28 PL PL1972158524A patent/PL82632B1/pl unknown
- 1972-10-30 JP JP47108772A patent/JPS4852769A/ja active Pending
-
1973
- 1973-07-30 AR AR249346A patent/AR197055A1/en active
- 1973-07-30 AR AR249345A patent/AR197054A1/en active
-
1974
- 1974-04-19 SU SU2018983A patent/SU509235A3/en active
- 1974-04-19 SU SU2018982A patent/SU511006A3/en active
Also Published As
Publication number | Publication date |
---|---|
NL7214621A (en) | 1973-05-02 |
IL40639A0 (en) | 1972-12-29 |
FR2158313A2 (en) | 1973-06-15 |
HU164715B (en) | 1974-04-11 |
FR2158313B2 (en) | 1976-04-23 |
DE2153902A1 (en) | 1973-05-03 |
AT320628B (en) | 1975-02-25 |
SU511006A3 (en) | 1976-04-15 |
AT327882B (en) | 1976-02-25 |
PL82632B1 (en) | 1975-10-31 |
ZA727504B (en) | 1973-08-29 |
ATA61874A (en) | 1975-05-15 |
AU467712B2 (en) | 1975-12-11 |
AR197055A1 (en) | 1974-03-08 |
SU509235A3 (en) | 1976-03-30 |
AR197008A1 (en) | 1974-03-08 |
AR197054A1 (en) | 1974-03-08 |
ATA61774A (en) | 1975-05-15 |
JPS4852769A (en) | 1973-07-24 |
AT327883B (en) | 1976-02-25 |
ES407933A2 (en) | 1975-11-01 |
DD102387A5 (en) | 1973-12-12 |
AU4827772A (en) | 1974-05-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLNP | Patent lapsed through nonpayment of renewal fees |