IL31458A - Hydantoin derivatives - Google Patents
Hydantoin derivativesInfo
- Publication number
- IL31458A IL31458A IL31458A IL3145869A IL31458A IL 31458 A IL31458 A IL 31458A IL 31458 A IL31458 A IL 31458A IL 3145869 A IL3145869 A IL 3145869A IL 31458 A IL31458 A IL 31458A
- Authority
- IL
- Israel
- Prior art keywords
- nitro
- hydantoin
- amino
- furfuryliden
- butyl
- Prior art date
Links
- 150000001469 hydantoins Chemical class 0.000 title claims 4
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title description 2
- 229940091173 hydantoin Drugs 0.000 claims description 23
- 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 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- -1 butyl-3- ( 5 ' -nitro-furfuryliden-amino ) -hydantoin Chemical compound 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- MJWVOJJALJAWBK-UHFFFAOYSA-N 3-[(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione Chemical compound O1C([N+](=O)[O-])=CC=C1C=NN1C(=O)NCC1=O MJWVOJJALJAWBK-UHFFFAOYSA-N 0.000 claims 1
- DCROTKUJYXYESN-UHFFFAOYSA-N 3-aminoimidazolidine-2,4-dione Chemical class NN1C(=O)CNC1=O DCROTKUJYXYESN-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 241001058196 Tritrichomonas foetus Species 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical class O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- LPYIXHHGKPBPCF-UHFFFAOYSA-N acetic acid;5-nitrofuran-2-carbaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=C(C=O)O1 LPYIXHHGKPBPCF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 229940071089 sarcosinate Drugs 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KVYKDNGUEZRPGJ-UHFFFAOYSA-N 1-Aminohydantoin Chemical compound NN1CC(=O)NC1=O KVYKDNGUEZRPGJ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010020524 Hydronephrosis Diseases 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
- 208000015924 Lithiasis Diseases 0.000 description 1
- 235000006629 Prosopis spicigera Nutrition 0.000 description 1
- 240000000037 Prosopis spicigera Species 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
- ROGQHXXFNVNMSC-UHFFFAOYSA-N ethyl 2-(propan-2-ylamino)acetate Chemical compound CCOC(=O)CNC(C)C ROGQHXXFNVNMSC-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 239000003981 vehicle Substances 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1202968 | 1968-01-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31458A0 IL31458A0 (en) | 1969-03-27 |
| IL31458A true IL31458A (en) | 1972-06-28 |
Family
ID=11139342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31458A IL31458A (en) | 1968-01-26 | 1969-01-21 | Hydantoin derivatives |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT281863B (en)) |
| BE (1) | BE727366A (en)) |
| BR (1) | BR6905856D0 (en)) |
| CH (1) | CH513176A (en)) |
| DE (1) | DE1966142A1 (en)) |
| ES (1) | ES362888A1 (en)) |
| FR (1) | FR2000801A1 (en)) |
| GB (1) | GB1174760A (en)) |
| IL (1) | IL31458A (en)) |
| NL (1) | NL6900631A (en)) |
| NO (1) | NO122976B (en)) |
| SE (1) | SE348732B (en)) |
| YU (1) | YU33193B (en)) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT317662B (de) * | 1971-05-15 | 1974-09-10 | Farmaceutici Italia | Tierwachstumfördernde Futtermittel |
| AU668360B2 (en) * | 1991-08-14 | 1996-05-02 | Warner Chilcott Company, Llc | Novel 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents |
| CN116041345A (zh) * | 2022-11-07 | 2023-05-02 | 温州大学 | 一种具有光学活性的含海因骨架的化合物的制备方法 |
-
1969
- 1969-01-15 NL NL6900631A patent/NL6900631A/xx unknown
- 1969-01-20 YU YU0125/69A patent/YU33193B/xx unknown
- 1969-01-21 IL IL31458A patent/IL31458A/en unknown
- 1969-01-22 DE DE19691966142 patent/DE1966142A1/de active Pending
- 1969-01-23 GB GB3905/69A patent/GB1174760A/en not_active Expired
- 1969-01-23 AT AT68669A patent/AT281863B/de not_active IP Right Cessation
- 1969-01-24 NO NO0281/69A patent/NO122976B/no unknown
- 1969-01-24 BR BR205856/69A patent/BR6905856D0/pt unknown
- 1969-01-24 ES ES362888A patent/ES362888A1/es not_active Expired
- 1969-01-24 FR FR6901336A patent/FR2000801A1/fr active Granted
- 1969-01-24 BE BE727366D patent/BE727366A/xx unknown
- 1969-01-24 SE SE00946/69A patent/SE348732B/xx unknown
- 1969-01-24 CH CH109669A patent/CH513176A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6900631A (en)) | 1969-07-29 |
| BR6905856D0 (pt) | 1973-02-08 |
| GB1174760A (en) | 1969-12-17 |
| FR2000801A1 (en) | 1969-09-12 |
| DE1902985A1 (de) | 1970-07-30 |
| YU33193B (en) | 1976-06-30 |
| FR2000801B1 (en)) | 1975-03-07 |
| YU12569A (en) | 1975-12-31 |
| CH513176A (de) | 1971-09-30 |
| NO122976B (en)) | 1971-09-13 |
| IL31458A0 (en) | 1969-03-27 |
| ES362888A1 (es) | 1970-11-16 |
| AT281863B (de) | 1970-06-10 |
| DE1966142A1 (de) | 1971-11-18 |
| SE348732B (en)) | 1972-09-11 |
| BE727366A (en)) | 1969-07-24 |
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