IL33025A - Process for the preparation of therapeutically useful 1-amino-hydantoin derivatives,and new 1-amino-hydantoin derivatives and pharmaceutical compositions containing them - Google Patents
Process for the preparation of therapeutically useful 1-amino-hydantoin derivatives,and new 1-amino-hydantoin derivatives and pharmaceutical compositions containing themInfo
- Publication number
- IL33025A IL33025A IL33025A IL3302566A IL33025A IL 33025 A IL33025 A IL 33025A IL 33025 A IL33025 A IL 33025A IL 3302566 A IL3302566 A IL 3302566A IL 33025 A IL33025 A IL 33025A
- Authority
- IL
- Israel
- Prior art keywords
- nitro
- furfurylideneamino
- formula
- amino
- alkyl group
- Prior art date
Links
- KVYKDNGUEZRPGJ-UHFFFAOYSA-N 1-Aminohydantoin Chemical class NN1CC(=O)NC1=O KVYKDNGUEZRPGJ-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- -1 2-hydrazinoacetic acid ester Chemical class 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WHNSJMMQNFSFBX-UHFFFAOYSA-N 2-[amino(carbamoyl)amino]acetic acid Chemical compound NC(=O)N(N)CC(O)=O WHNSJMMQNFSFBX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 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 2
- 239000006187 pill Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000194033 Enterococcus Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 238000009835 boiling Methods 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heat Treatment Of Steel (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 |
|---|---|
| IL33025A true IL33025A (en) | 1970-02-19 |
Family
ID=9762731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33025A IL33025A (en) | 1965-01-27 | 1966-01-23 | Process for the preparation of therapeutically useful 1-amino-hydantoin derivatives,and new 1-amino-hydantoin derivatives and pharmaceutical compositions containing them |
| IL25030A IL25030A (en) | 1965-01-27 | 1966-01-23 | Esters of n'-5-nitro-2-furfurylidene-n-carbamoyl-hydrazino acetic acid,processes for their preparation and pharmaceutical compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25030A IL25030A (en) | 1965-01-27 | 1966-01-23 | Esters of n'-5-nitro-2-furfurylidene-n-carbamoyl-hydrazino acetic acid,processes for their preparation and pharmaceutical compositions containing them |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3452053A (xx) |
| BE (1) | BE675699A (xx) |
| CH (1) | CH454167A (xx) |
| DE (2) | DE1543788A1 (xx) |
| DK (1) | DK115775B (xx) |
| FR (1) | FR1555474A (xx) |
| GB (2) | GB1121311A (xx) |
| IL (2) | IL33025A (xx) |
| NL (1) | NL6601004A (xx) |
| NO (1) | NO117593B (xx) |
| SE (1) | SE336344B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5544752B2 (xx) * | 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 (xx) * | 1963-02-09 | 1900-01-01 |
-
1965
- 1965-01-27 GB GB3670/65A patent/GB1121311A/en not_active Expired
- 1965-01-27 GB GB53706/67A patent/GB1121312A/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 NL NL6601004A patent/NL6601004A/xx unknown
- 1966-01-26 DE DE19661543788 patent/DE1543788A1/de active Pending
- 1966-01-26 SE SE00993/66A patent/SE336344B/xx unknown
- 1966-01-26 DE DE19661770790 patent/DE1770790A1/de active Pending
- 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 |
|---|---|
| GB1121311A (en) | 1968-07-24 |
| BE675699A (xx) | 1966-07-27 |
| NO117593B (xx) | 1969-09-01 |
| US3452053A (en) | 1969-06-24 |
| IL25030A (en) | 1970-02-19 |
| FR1555474A (xx) | 1969-01-31 |
| DE1543788A1 (de) | 1969-12-11 |
| CH454167A (de) | 1968-04-15 |
| SE336344B (xx) | 1971-07-05 |
| DE1770790A1 (de) | 1971-12-16 |
| DK115775B (da) | 1969-11-10 |
| NL6601004A (xx) | 1966-07-28 |
| GB1121312A (en) | 1968-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0180798B1 (ko) | 결정성 페니실린 유도체, 그의 제법 및 용도 | |
| JPS62161728A (ja) | 抗菌剤 | |
| HU194819B (en) | Process for producing pleuromutilin derivatives and pharmaceutical compositions containing them | |
| US3769295A (en) | Nitrofuryl derivatives of 5-substituted isoxazolines | |
| DE2204574A1 (de) | Verfahren zur herstellung von 3-aminobenzo-1,2,4-triazin-di-n-oxiden (1,4) | |
| FR2476071A1 (fr) | Nouveaux acides 2-amino-3-(a-hydroxybenzyl)-phenylacetiques et leurs esters et amides, utiles notamment comme agents anti-inflammatoires, et compositions pharmaceutiques les contenant | |
| US4044130A (en) | Compositions for the control of microorganisms | |
| IL33025A (en) | Process for the preparation of therapeutically useful 1-amino-hydantoin derivatives,and new 1-amino-hydantoin derivatives and pharmaceutical compositions containing them | |
| US4049816A (en) | Antiviral 2-amino-5-[1-(indol-3-yl)alkyl]-2-thiazolin-4-ones | |
| CH646138A5 (fr) | Amino-2-benzoyl-3-phenylacetamides et leurs homologues cycliques utiles comme medicaments et compositions pharmaceutiques les contenant. | |
| US3852292A (en) | 2-(pyridyl)-imidazole-4,5-dicarboxylic acid and derivatives | |
| US4159380A (en) | Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols | |
| DE1670097C3 (de) | 5-[l (4-Chlorbenzoyl)- 3-indolylmethyl] -tetrazol und Verfahren zu dessen Herstellung | |
| DE2629926A1 (de) | Clavulansaeureamide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| US3705903A (en) | 2-carbamido and thiocarbamido oxazoles | |
| US3407195A (en) | 4-methyl-1-(5-nitrofurfurylideneamino)-2-imidazolidinone | |
| US3682956A (en) | Substituted 3-(5-nitro-2-furyl)-pyrazoles | |
| US3809755A (en) | Certain 2-oxazolylthioureas as fungicides | |
| US3632577A (en) | 5-nitrofuryl derivatives | |
| US3575998A (en) | Oxadiazolyl-substituted nitroimidazoles | |
| US3720668A (en) | Nitrofuryl-oxadiazole amides | |
| US3427387A (en) | Antibacterial composition containing 5-nitro-2-furyl-1,2,4-triazoles | |
| US3682953A (en) | Substituted 5-nitrofuryl-pyrazoles | |
| US3835165A (en) | Nitrofuryl-alpha-halo-hydrazones | |
| US3562286A (en) | Nitrofuryl isoxazole derivatives |