DE1770790A1 - 1-Aminohydantoinderivate,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipraeparate - Google Patents
1-Aminohydantoinderivate,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende ArzneipraeparateInfo
- Publication number
- DE1770790A1 DE1770790A1 DE19661770790 DE1770790A DE1770790A1 DE 1770790 A1 DE1770790 A1 DE 1770790A1 DE 19661770790 DE19661770790 DE 19661770790 DE 1770790 A DE1770790 A DE 1770790A DE 1770790 A1 DE1770790 A1 DE 1770790A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- nitro
- furfurylideneamino
- hitro
- inert
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 7
- KVYKDNGUEZRPGJ-UHFFFAOYSA-N 1-Aminohydantoin Chemical class NN1CC(=O)NC1=O KVYKDNGUEZRPGJ-UHFFFAOYSA-N 0.000 title claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- -1 carbamoyl halide Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 241000607760 Shigella sonnei Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- PFEVLHPHNQFASW-UHFFFAOYSA-N cyclohexyl cyanate Chemical compound N#COC1CCCCC1 PFEVLHPHNQFASW-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229940115939 shigella sonnei Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- LWKXFZOGEJOYQI-UHFFFAOYSA-N 3-hexylimidazolidine-2,4-dione Chemical compound CCCCCCN1C(=O)CNC1=O LWKXFZOGEJOYQI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- IYYXRVUUBHBXGF-UHFFFAOYSA-N acetic acid;aminourea Chemical compound CC(O)=O.NNC(N)=O IYYXRVUUBHBXGF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- PPMIZXCHYPWITO-UHFFFAOYSA-N ethyl acetate;hydrazine Chemical compound NN.CCOC(C)=O PPMIZXCHYPWITO-UHFFFAOYSA-N 0.000 description 1
- JXBPSENIJJPTCI-UHFFFAOYSA-N ethyl cyanate Chemical compound CCOC#N JXBPSENIJJPTCI-UHFFFAOYSA-N 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 102220169347 rs201929423 Human genes 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000015149 toffees Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
- C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
- C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heat Treatment Of Steel (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3670/65A GB1121311A (en) | 1965-01-27 | 1965-01-27 | N-carbamoyl-hydrazinoacetic acid esters, processes for their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770790A1 true DE1770790A1 (de) | 1971-12-16 |
Family
ID=9762731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661770790 Pending DE1770790A1 (de) | 1965-01-27 | 1966-01-26 | 1-Aminohydantoinderivate,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipraeparate |
| DE19661543788 Pending DE1543788A1 (de) | 1965-01-27 | 1966-01-26 | N-Carbamoylhydrazinessigsaeureester,Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneipraeparate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543788 Pending DE1543788A1 (de) | 1965-01-27 | 1966-01-26 | N-Carbamoylhydrazinessigsaeureester,Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneipraeparate |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3452053A (enExample) |
| BE (1) | BE675699A (enExample) |
| CH (1) | CH454167A (enExample) |
| DE (2) | DE1770790A1 (enExample) |
| DK (1) | DK115775B (enExample) |
| FR (1) | FR1555474A (enExample) |
| GB (2) | GB1121312A (enExample) |
| IL (2) | IL33025A (enExample) |
| NL (1) | NL6601004A (enExample) |
| NO (1) | NO117593B (enExample) |
| SE (1) | SE336344B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5544752B2 (enExample) * | 1973-02-01 | 1980-11-13 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL171628C (nl) * | 1950-05-29 | Inst Francais Du Petrole | Inrichting voor het uitzenden van akoestische golven in een vloeibaar milieu. | |
| NL302010A (enExample) * | 1963-02-09 | 1900-01-01 |
-
1965
- 1965-01-27 GB GB53706/67A patent/GB1121312A/en not_active Expired
- 1965-01-27 GB GB3670/65A patent/GB1121311A/en not_active Expired
-
1966
- 1966-01-22 NO NO161377A patent/NO117593B/no unknown
- 1966-01-23 IL IL33025A patent/IL33025A/en unknown
- 1966-01-23 IL IL25030A patent/IL25030A/en unknown
- 1966-01-25 CH CH94166A patent/CH454167A/de unknown
- 1966-01-26 DE DE19661770790 patent/DE1770790A1/de active Pending
- 1966-01-26 SE SE00993/66A patent/SE336344B/xx unknown
- 1966-01-26 DE DE19661543788 patent/DE1543788A1/de active Pending
- 1966-01-26 NL NL6601004A patent/NL6601004A/xx unknown
- 1966-01-27 FR FR1555474D patent/FR1555474A/fr not_active Expired
- 1966-01-27 US US523279A patent/US3452053A/en not_active Expired - Lifetime
- 1966-01-27 BE BE675699A patent/BE675699A/fr unknown
-
1967
- 1967-04-25 DK DK219667AA patent/DK115775B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6601004A (enExample) | 1966-07-28 |
| GB1121311A (en) | 1968-07-24 |
| DE1543788A1 (de) | 1969-12-11 |
| IL33025A (en) | 1970-02-19 |
| CH454167A (de) | 1968-04-15 |
| FR1555474A (enExample) | 1969-01-31 |
| NO117593B (enExample) | 1969-09-01 |
| US3452053A (en) | 1969-06-24 |
| BE675699A (enExample) | 1966-07-27 |
| DK115775B (da) | 1969-11-10 |
| IL25030A (en) | 1970-02-19 |
| SE336344B (enExample) | 1971-07-05 |
| GB1121312A (en) | 1968-07-24 |
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