DE2262553A1 - 4- eckige klammer auf 1'-alkyl-5'nitroimidazolyl-2'-methylen-imino eckige klammer zu - tetrahydro-1,4-thiazin-1,1dioxide und verfahren zu ihrer herstellung - Google Patents
4- eckige klammer auf 1'-alkyl-5'nitroimidazolyl-2'-methylen-imino eckige klammer zu - tetrahydro-1,4-thiazin-1,1dioxide und verfahren zu ihrer herstellungInfo
- Publication number
- DE2262553A1 DE2262553A1 DE2262553A DE2262553A DE2262553A1 DE 2262553 A1 DE2262553 A1 DE 2262553A1 DE 2262553 A DE2262553 A DE 2262553A DE 2262553 A DE2262553 A DE 2262553A DE 2262553 A1 DE2262553 A1 DE 2262553A1
- Authority
- DE
- Germany
- Prior art keywords
- thiazine
- tetrahydro
- nitroimidazolyl
- methyl
- dioxide
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- YDKNASMIEZGJEJ-UHFFFAOYSA-N 1,1-dioxo-1,4-thiazinan-4-amine Chemical class NN1CCS(=O)(=O)CC1 YDKNASMIEZGJEJ-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 description 21
- 244000052769 pathogen Species 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 230000001717 pathogenic effect Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 6
- 229960000282 metronidazole Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 206010019692 hepatic necrosis Diseases 0.000 description 5
- 231100000149 liver necrosis Toxicity 0.000 description 5
- 241000699800 Cricetinae Species 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 241000224432 Entamoeba histolytica Species 0.000 description 3
- 241000699673 Mesocricetus auratus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001502500 Trichomonadida Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000224526 Trichomonas Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940007078 entamoeba histolytica Drugs 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- JLQLFVSTEDRFAD-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbaldehyde Chemical compound CN1C(C=O)=NC=C1[N+]([O-])=O JLQLFVSTEDRFAD-UHFFFAOYSA-N 0.000 description 1
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 1
- MESFXNGUDNODTJ-UHFFFAOYSA-N 2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)NC=CC=C1 MESFXNGUDNODTJ-UHFFFAOYSA-N 0.000 description 1
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 1
- 241000224489 Amoeba Species 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000224421 Heterolobosea Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 206010044620 Trichomoniasis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 210000003001 amoeba Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- -1 methoxymethyl-tetrahydro-1,4-thiazine-1,1-dioxide Chemical compound 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2262553A DE2262553A1 (de) | 1972-12-21 | 1972-12-21 | 4- eckige klammer auf 1'-alkyl-5'nitroimidazolyl-2'-methylen-imino eckige klammer zu - tetrahydro-1,4-thiazin-1,1dioxide und verfahren zu ihrer herstellung |
| NL7317189A NL7317189A (enExample) | 1972-12-21 | 1973-12-14 | |
| US425979A US3884913A (en) | 1972-12-21 | 1973-12-19 | 4-(1{40 -Alkyl-5{40 -nitroimidazolyl-2{40 -methylene -imino)-tetrahydro-1,4-thiazine-1,1-dioxides and process for their manufacture |
| JP48142595A JPS4988884A (enExample) | 1972-12-21 | 1973-12-21 | |
| FR7346187A FR2211255A1 (enExample) | 1972-12-21 | 1973-12-21 | |
| BE139183A BE808997A (fr) | 1972-12-21 | 1973-12-21 | 1,1,-dioxydes de 4-(1'-alcoyl-5'-nitroimidazolyl-2'-methylene-imino) -tetrahydro-1,4-thiazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2262553A DE2262553A1 (de) | 1972-12-21 | 1972-12-21 | 4- eckige klammer auf 1'-alkyl-5'nitroimidazolyl-2'-methylen-imino eckige klammer zu - tetrahydro-1,4-thiazin-1,1dioxide und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2262553A1 true DE2262553A1 (de) | 1974-06-27 |
Family
ID=5865018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2262553A Pending DE2262553A1 (de) | 1972-12-21 | 1972-12-21 | 4- eckige klammer auf 1'-alkyl-5'nitroimidazolyl-2'-methylen-imino eckige klammer zu - tetrahydro-1,4-thiazin-1,1dioxide und verfahren zu ihrer herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3884913A (enExample) |
| JP (1) | JPS4988884A (enExample) |
| BE (1) | BE808997A (enExample) |
| DE (1) | DE2262553A1 (enExample) |
| FR (1) | FR2211255A1 (enExample) |
| NL (1) | NL7317189A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8193180B2 (en) * | 2007-01-24 | 2012-06-05 | Women & Infants Hospital | N-amino tetrahydrothiazine derivatives, method of manufacture and use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3472864A (en) * | 1964-03-18 | 1969-10-14 | Merck & Co Inc | 2-carbonyl-5-nitroimidazoles |
| US3784543A (en) * | 1970-10-28 | 1974-01-08 | Ciba Geigy Corp | 4-(n-(5-nitro-2-thiazolyl)-formimidoyl)-thiomorpholines and oxides |
-
1972
- 1972-12-21 DE DE2262553A patent/DE2262553A1/de active Pending
-
1973
- 1973-12-14 NL NL7317189A patent/NL7317189A/xx unknown
- 1973-12-19 US US425979A patent/US3884913A/en not_active Expired - Lifetime
- 1973-12-21 BE BE139183A patent/BE808997A/xx unknown
- 1973-12-21 FR FR7346187A patent/FR2211255A1/fr not_active Withdrawn
- 1973-12-21 JP JP48142595A patent/JPS4988884A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2211255A1 (enExample) | 1974-07-19 |
| JPS4988884A (enExample) | 1974-08-24 |
| BE808997A (fr) | 1974-06-21 |
| US3884913A (en) | 1975-05-20 |
| NL7317189A (enExample) | 1974-06-25 |
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