JPS6225148B2 - - Google Patents
Info
- Publication number
- JPS6225148B2 JPS6225148B2 JP52124129A JP12412977A JPS6225148B2 JP S6225148 B2 JPS6225148 B2 JP S6225148B2 JP 52124129 A JP52124129 A JP 52124129A JP 12412977 A JP12412977 A JP 12412977A JP S6225148 B2 JPS6225148 B2 JP S6225148B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- stirred
- mol
- solution
- mixture
- 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.)
- Expired
Links
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000012265 solid product Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000001914 filtration Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- -1 1-[[[5-(3,4-dichlorophenyl)-2 -oxazolyl]methylene]amino]-2.4 -Imidazolidinedione Chemical compound 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 11
- 239000004312 hexamethylene tetramine Substances 0.000 description 9
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- YWNKNCQONKYNJB-UHFFFAOYSA-N 1-phenylethanone;hydrochloride Chemical compound Cl.CC(=O)C1=CC=CC=C1 YWNKNCQONKYNJB-UHFFFAOYSA-N 0.000 description 2
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WEOHANUVLKERQI-UHFFFAOYSA-N (2,4-dioxoimidazolidin-1-yl)azanium;chloride Chemical compound Cl.NN1CC(=O)NC1=O WEOHANUVLKERQI-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 1
- GNWAWPILIXDRDH-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone hydrochloride Chemical compound Cl.CC(=O)C1=CC=C(F)C=C1 GNWAWPILIXDRDH-UHFFFAOYSA-N 0.000 description 1
- ABXGMGUHGLQMAW-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(F)(F)F)=C1 ABXGMGUHGLQMAW-UHFFFAOYSA-N 0.000 description 1
- GUHJJKBRVDQTDE-UHFFFAOYSA-N 1-[[5-(4-chlorophenyl)-1,3-oxazol-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1C(O1)=CN=C1C=NN1C(=O)NC(=O)C1 GUHJJKBRVDQTDE-UHFFFAOYSA-N 0.000 description 1
- NSILJEIZFWTIGC-UHFFFAOYSA-N 1-[[5-(4-fluorophenyl)-1,3-oxazol-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C(O1)=CN=C1C=NN1C(=O)NC(=O)C1 NSILJEIZFWTIGC-UHFFFAOYSA-N 0.000 description 1
- WKHNBDMOAQQLDD-UHFFFAOYSA-N 1-[[5-(4-nitrophenyl)-1,3-oxazol-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CN=C1C=NN1C(=O)NC(=O)C1 WKHNBDMOAQQLDD-UHFFFAOYSA-N 0.000 description 1
- JLGNBZNUPRFZII-UHFFFAOYSA-N 2-(2,4-dioxoimidazolidin-1-yl)iminoacetic acid Chemical compound OC(=O)C=NN1CC(=O)NC1=O JLGNBZNUPRFZII-UHFFFAOYSA-N 0.000 description 1
- YFICQJRJZJMPIH-UHFFFAOYSA-N 2-(2,4-dioxoimidazolidin-1-yl)iminoacetyl chloride Chemical compound ClC(=O)C=NN1CC(=O)NC1=O YFICQJRJZJMPIH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IDRFAFYEURFRFD-UHFFFAOYSA-N 2-amino-1-(3,4-dichlorophenyl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=C(Cl)C(Cl)=C1 IDRFAFYEURFRFD-UHFFFAOYSA-N 0.000 description 1
- DVMAOBMOGUURBU-UHFFFAOYSA-N 2-amino-1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound NCC(=O)C1=CC=CC(C(F)(F)F)=C1 DVMAOBMOGUURBU-UHFFFAOYSA-N 0.000 description 1
- HEPPSEJUYWXQJV-UHFFFAOYSA-N 2-amino-1-[3-(trifluoromethyl)phenyl]ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=CC(C(F)(F)F)=C1 HEPPSEJUYWXQJV-UHFFFAOYSA-N 0.000 description 1
- XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ALNFHFBRFRQDEG-UHFFFAOYSA-N N-[2-(4-chlorophenyl)-2-oxoethyl]-N-[(2,4-dioxoimidazolidin-1-yl)iminomethyl]formamide Chemical compound ClC1=CC=C(C=C1)C(CN(C=O)C=NN1C(NC(C1)=O)=O)=O ALNFHFBRFRQDEG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- FJYQSDXMBNMMCH-UHFFFAOYSA-N n-[(2,4-dioxoimidazolidin-1-yl)iminomethyl]-n-phenacylformamide Chemical compound C1C(=O)NC(=O)N1N=CN(C=O)CC(=O)C1=CC=CC=C1 FJYQSDXMBNMMCH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/733,296 US4049650A (en) | 1976-10-18 | 1976-10-18 | 1-[[[5-(Substituted phenyl)-2-oxazolyl]methylene]amino]-2,4-imidazolidinediones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5350167A JPS5350167A (en) | 1978-05-08 |
| JPS6225148B2 true JPS6225148B2 (en, 2012) | 1987-06-01 |
Family
ID=24947035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12412977A Granted JPS5350167A (en) | 1976-10-18 | 1977-10-18 | 11***55*substituted**22oxazolyl*methlene*amino** 2*44imidalizinedione and its preparation |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4049650A (en, 2012) |
| JP (1) | JPS5350167A (en, 2012) |
| AU (1) | AU505351B2 (en, 2012) |
| BE (1) | BE859819A (en, 2012) |
| CA (1) | CA1084510A (en, 2012) |
| CH (1) | CH629800A5 (en, 2012) |
| DE (1) | DE2746550A1 (en, 2012) |
| ES (1) | ES463297A1 (en, 2012) |
| FR (1) | FR2367763A1 (en, 2012) |
| GB (1) | GB1530770A (en, 2012) |
| MX (1) | MX5011E (en, 2012) |
| NL (1) | NL7711416A (en, 2012) |
| SE (1) | SE435382B (en, 2012) |
| ZA (1) | ZA775228B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2657559A1 (de) * | 1976-12-18 | 1978-06-22 | Bayer Ag | Dioxopiperazinderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel und als zwischenprodukte fuer beta-lactamantibiotika |
| US4128711A (en) * | 1977-10-06 | 1978-12-05 | Morton-Norwich Products, Inc. | 1-[[1H-Pyrrol-2-ylmethylene]amino]-2,4-imidazolidinedione |
| US4822629A (en) * | 1986-12-12 | 1989-04-18 | Norwich Eaton Pharmaceuticals, Inc. | Azumolene dosage form |
| US4861790A (en) * | 1987-10-28 | 1989-08-29 | Norwich Eaton Pharmaceuticals, Inc. | Use of azumolene for the treatment of malignant hyperthermia |
| WO2007145203A1 (ja) * | 2006-06-13 | 2007-12-21 | Daiichi Fine Chemical Co., Ltd. | 光学活性２－アミノ－１－（４－フルオロフェニル）エタノール |
| RU2503454C1 (ru) | 2009-09-30 | 2014-01-10 | Сисейдо Компани, Лтд. | Ингибитор гепараназной активности |
| HUP1300720A2 (hu) * | 2013-12-12 | 2015-06-29 | Univ Szegedi | Gyógyászati készítmények sebgyógyulás elõsegítésére |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415821A (en) * | 1965-09-07 | 1968-12-10 | Norwich Pharma Co | 1-(5-substituted)furfurylideneamino hydantoins and imidazolidinones |
| DE2106298A1 (en, 2012) * | 1971-02-10 | 1972-10-12 | ||
| US3803136A (en) * | 1972-08-23 | 1974-04-09 | Morton Norwich Products Inc | 5-hydroxy-1-((5-(substituted phenyl)furfurylidene)amino)hydrantoins |
| US3843636A (en) * | 1974-01-25 | 1974-10-22 | Morton Norwich Products Inc | 1-(5-(p-methoxyphenyl)furfurylidene)amino)hydantoin |
| US4001222A (en) * | 1975-10-14 | 1977-01-04 | Morton-Norwich Products, Inc. | 3-(Aminoacyl)-1-{[5-(substituted phenyl)furfurylidene]amino}hydantoins and process for their preparation thereof |
-
1976
- 1976-10-18 US US05/733,296 patent/US4049650A/en not_active Expired - Lifetime
-
1977
- 1977-08-19 AU AU28036/77A patent/AU505351B2/en not_active Expired
- 1977-08-23 MX MX776040U patent/MX5011E/es unknown
- 1977-08-29 ZA ZA00775228A patent/ZA775228B/xx unknown
- 1977-09-08 SE SE7710086A patent/SE435382B/xx not_active IP Right Cessation
- 1977-09-16 GB GB38790/77A patent/GB1530770A/en not_active Expired
- 1977-09-19 CH CH1140977A patent/CH629800A5/de not_active IP Right Cessation
- 1977-10-12 CA CA288,542A patent/CA1084510A/en not_active Expired
- 1977-10-17 BE BE181820A patent/BE859819A/xx not_active IP Right Cessation
- 1977-10-17 DE DE19772746550 patent/DE2746550A1/de active Granted
- 1977-10-17 ES ES463297A patent/ES463297A1/es not_active Expired
- 1977-10-18 NL NL7711416A patent/NL7711416A/xx active Search and Examination
- 1977-10-18 FR FR7731344A patent/FR2367763A1/fr active Granted
- 1977-10-18 JP JP12412977A patent/JPS5350167A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7711416A (nl) | 1978-04-20 |
| GB1530770A (en) | 1978-11-01 |
| ZA775228B (en) | 1979-04-25 |
| JPS5350167A (en) | 1978-05-08 |
| AU505351B2 (en) | 1979-11-15 |
| CH629800A5 (de) | 1982-05-14 |
| SE435382B (sv) | 1984-09-24 |
| SE7710086L (sv) | 1978-04-19 |
| DE2746550C2 (en, 2012) | 1987-10-15 |
| MX5011E (es) | 1983-02-16 |
| DE2746550A1 (de) | 1978-04-20 |
| ES463297A1 (es) | 1978-11-16 |
| AU2803677A (en) | 1979-02-22 |
| FR2367763A1 (fr) | 1978-05-12 |
| CA1084510A (en) | 1980-08-26 |
| FR2367763B1 (en, 2012) | 1980-06-27 |
| US4049650A (en) | 1977-09-20 |
| BE859819A (fr) | 1978-04-17 |
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