SU455534A3 - Method for preparing nitrofurilamidine or nitrothienylamidine derivatives - Google Patents
Method for preparing nitrofurilamidine or nitrothienylamidine derivativesInfo
- Publication number
- SU455534A3 SU455534A3 SU1842826A SU1842826A SU455534A3 SU 455534 A3 SU455534 A3 SU 455534A3 SU 1842826 A SU1842826 A SU 1842826A SU 1842826 A SU1842826 A SU 1842826A SU 455534 A3 SU455534 A3 SU 455534A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- derivatives
- nitrothienylamidine
- nitrofurilamidine
- preparing
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 nitrofuryl amidine Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ НИТРОФУРИЛАМИДИНА ИЛИ НИТРОТИЕНИЛАМИДИНА(54) METHOD FOR OBTAINING DERIVATIVES NITROFURYLAMIDINE OR NITROTHYENYLAMIDINE
1one
Изобретение относитс к способу получени новых производных нитрофуриламидина или нитротиениламидина, обладающих значительным антибактериальным действием.This invention relates to a process for the preparation of new derivatives of nitrofuryl amidine or nitrothienyl amidine, which have a significant antibacterial effect.
Основанный на известной реакции альдольной конденсации охватываемый насто щим изобретением, способ позвол ет получать новые соединени , обладающие лучшими свойствами , чем известные аналоги подобного действи .Based on the known aldol condensation reaction covered by the present invention, the method allows to obtain new compounds with better properties than the known analogues of similar effect.
Предложен способ получени соединений общей формулы IA method for the preparation of compounds of general formula I is provided.
RiRi
CH-He-t- N- C-NCH-He-t-N-C-N
ff
R9R9
где Ri, и Rs - водород или низщие алкил , алкоксиалкил или алкилмеркаптоалкил, причем два остатка вместе с атомами, с которыми они св заны могут образовывать 5- 6-членные кольца, которые могут дополнительно содержать один или два атома азота, кислорода или серы;where Ri and Rs are hydrogen or lower alkyl, alkoxyalkyl or alkyl mercaptoalkyl, two of which, together with the atoms to which they are attached, can form 5-6 membered rings, which may additionally contain one or two nitrogen, oxygen or sulfur atoms;
X - атом кислорода или атом серы:X is an oxygen atom or a sulfur atom:
Het - системы нафтиридина или s-триазоло- 4 ,3-6 -пиридазина, которые, при известных услови х, могут быть замещены низщими алкильными, амино- или гидроксильными группами,Het - naphthyridine or s-triazolo-4, 3-6 -pyridazine systems, which, under certain conditions, can be substituted by lower alkyl, amino or hydroxyl groups,
или их солей.or their salts.
Согласно изобретению соединение формулы I получают взаимодействием соединений формулы ПAccording to the invention, a compound of formula I is obtained by reacting compounds of the formula P
/RI/ RI
ОНз Het-N C-NCOHZ Het-N C-NC
I R2I R2
5П5P
где RI, R2, Ra и Het имеют выщеуказанные значени , с 5-нитрофурфуролом или соответственно 5-нитротиофенальдегидом-2 или их реакционноспособными производными.where RI, R2, Ra and Het are as defined above, with 5-nitrofurfurol or 5-nitrothiophenaldehyde-2, respectively, or their reactive derivatives.
Конденсацию 5-нитрофурфурола или соответственно 5-нитротиофенальдегида-2 с соединени ми формулы II можно провести лишьThe condensation of 5-nitrofurfurol or 5-nitrothiophenaldehyde-2, respectively, with compounds of formula II can only be carried out
в том случае, если метильна группа находитс в орто- или параположении, по крайней мере, к одному активирующему азоту. Реакif the methyl group is in the ortho or para position at least to one of the activating nitrogen. Reak
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702030581 DE2030581A1 (en) | 1970-06-20 | 1970-06-20 | Nitrofuryl amidine derivatives and process for making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU455534A3 true SU455534A3 (en) | 1974-12-30 |
Family
ID=5774553
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1842000A SU468410A3 (en) | 1970-06-20 | 1971-06-18 | Method for preparing nitrofurilamidine derivatives |
| SU1677748A SU421188A3 (en) | 1970-06-20 | 1971-06-18 | METHOD OF OBTAINING DERIVATIVE NITROFURIL (OR THIENYL) AMIDIN |
| SU1842826A SU455534A3 (en) | 1970-06-20 | 1971-06-18 | Method for preparing nitrofurilamidine or nitrothienylamidine derivatives |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1842000A SU468410A3 (en) | 1970-06-20 | 1971-06-18 | Method for preparing nitrofurilamidine derivatives |
| SU1677748A SU421188A3 (en) | 1970-06-20 | 1971-06-18 | METHOD OF OBTAINING DERIVATIVE NITROFURIL (OR THIENYL) AMIDIN |
Country Status (11)
| Country | Link |
|---|---|
| AT (3) | AT304520B (en) |
| CA (1) | CA942304A (en) |
| DE (1) | DE2030581A1 (en) |
| ES (1) | ES392288A1 (en) |
| FR (1) | FR2100800B1 (en) |
| GB (1) | GB1309727A (en) |
| IE (1) | IE35388B1 (en) |
| NL (1) | NL7108264A (en) |
| SE (1) | SE372769B (en) |
| SU (3) | SU468410A3 (en) |
| ZA (1) | ZA713906B (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 |
| RS55630B1 (en) | 2005-12-21 | 2017-06-30 | Janssen Pharmaceutica Nv | TRIAZOLOPYRIDASINES AS TYROSINE KINASE MODULATORS |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1485277A (en) * | 1965-07-02 | 1967-06-16 | Boehringer & Soehne Gmbh | Process for the preparation of novel 5-nitrofuryl and 5-nitrothienyl compounds |
| US3658796A (en) * | 1968-04-10 | 1972-04-25 | Boehringer Mannheim Gmbh | 5-nitrofuran derivatives |
-
1970
- 1970-06-20 DE DE19702030581 patent/DE2030581A1/en active Pending
-
1971
- 1971-06-15 ZA ZA713906A patent/ZA713906B/en unknown
- 1971-06-16 NL NL7108264A patent/NL7108264A/xx unknown
- 1971-06-16 ES ES392288A patent/ES392288A1/en not_active Expired
- 1971-06-16 GB GB2821771A patent/GB1309727A/en not_active Expired
- 1971-06-18 AT AT530171A patent/AT304520B/en not_active IP Right Cessation
- 1971-06-18 AT AT127272A patent/AT309407B/en not_active IP Right Cessation
- 1971-06-18 IE IE789/71A patent/IE35388B1/en unknown
- 1971-06-18 SU SU1842000A patent/SU468410A3/en active
- 1971-06-18 AT AT127172A patent/AT309406B/en not_active IP Right Cessation
- 1971-06-18 SE SE7107953A patent/SE372769B/xx unknown
- 1971-06-18 CA CA116,103A patent/CA942304A/en not_active Expired
- 1971-06-18 SU SU1677748A patent/SU421188A3/en active
- 1971-06-18 FR FR7122199A patent/FR2100800B1/fr not_active Expired
- 1971-06-18 SU SU1842826A patent/SU455534A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2100800B1 (en) | 1975-10-10 |
| SU468410A3 (en) | 1975-04-25 |
| DE2030581A1 (en) | 1971-12-30 |
| AT309406B (en) | 1973-08-27 |
| ES392288A1 (en) | 1973-10-01 |
| IE35388B1 (en) | 1976-02-04 |
| CA942304A (en) | 1974-02-19 |
| SU421188A3 (en) | 1974-03-25 |
| FR2100800A1 (en) | 1972-03-24 |
| IE35388L (en) | 1971-12-20 |
| NL7108264A (en) | 1971-12-22 |
| AT304520B (en) | 1973-01-10 |
| ZA713906B (en) | 1972-02-23 |
| SE372769B (en) | 1975-01-13 |
| AT309407B (en) | 1973-08-27 |
| GB1309727A (en) | 1973-03-14 |
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