FI59993C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-oxo-2-imidazolidinylidenurinaemnen - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-oxo-2-imidazolidinylidenurinaemnen Download PDFInfo
- Publication number
- FI59993C FI59993C FI3065/74A FI306574A FI59993C FI 59993 C FI59993 C FI 59993C FI 3065/74 A FI3065/74 A FI 3065/74A FI 306574 A FI306574 A FI 306574A FI 59993 C FI59993 C FI 59993C
- Authority
- FI
- Finland
- Prior art keywords
- oxo
- imidazolidinylidene
- urea
- methyl
- isocyanate
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- 230000001225 therapeutic effect Effects 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- -1 aryl isocyanate Chemical class 0.000 description 25
- 241000700159 Rattus Species 0.000 description 20
- 235000013877 carbamide Nutrition 0.000 description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
- 239000004202 carbamide Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229940109239 creatinine Drugs 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000008267 milk Substances 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 3
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
- 241001279009 Strychnos toxifera Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229960005453 strychnine Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 2
- NQLHETVWDMRIPV-UHFFFAOYSA-N 2-imino-1,3-dimethylimidazolidin-4-one Chemical compound CN1CC(=O)N(C)C1=N NQLHETVWDMRIPV-UHFFFAOYSA-N 0.000 description 2
- YQLRKXVEALTVCZ-UHFFFAOYSA-N 2-isocyanato-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1N=C=O YQLRKXVEALTVCZ-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003874 central nervous system depressant Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229960003624 creatine Drugs 0.000 description 2
- 239000006046 creatine Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WTHDKMILWLGDKL-UHFFFAOYSA-N urea;hydrate Chemical compound O.NC(N)=O WTHDKMILWLGDKL-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UYSMPPQHGXDNCQ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=C(C)C(C)=C1 UYSMPPQHGXDNCQ-UHFFFAOYSA-N 0.000 description 1
- UTEUJYOPYILQQB-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(1,3-dimethyl-4-oxoimidazolidin-2-ylidene)urea Chemical compound CN1CC(=O)N(C)C1=NC(=O)NC1=CC=CC(Cl)=C1 UTEUJYOPYILQQB-UHFFFAOYSA-N 0.000 description 1
- UVMJRAGOQOABOE-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(5-oxo-1,4-dihydroimidazol-2-yl)urea Chemical compound ClC1=CC=CC(NC(=O)N=C2NC(=O)CN2)=C1 UVMJRAGOQOABOE-UHFFFAOYSA-N 0.000 description 1
- ZYXFKTFNMNGRLX-UHFFFAOYSA-N 1-(3-ethyl-5-oxo-4h-imidazol-2-yl)-3-(3-ethylphenyl)urea Chemical compound CCN1CC(=O)NC1=NC(=O)NC1=CC=CC(CC)=C1 ZYXFKTFNMNGRLX-UHFFFAOYSA-N 0.000 description 1
- DORNEORKHCTYLV-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(3-nitrophenyl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC([N+]([O-])=O)=C1 DORNEORKHCTYLV-UHFFFAOYSA-N 0.000 description 1
- WZPYHYBZJMSGPN-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(3-propylphenyl)urea Chemical compound CCCC1=CC=CC(NC(=O)N=C2N(CC(=O)N2)C)=C1 WZPYHYBZJMSGPN-UHFFFAOYSA-N 0.000 description 1
- UGAKYEVNTSKJHX-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(4-methylphenyl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=C(C)C=C1 UGAKYEVNTSKJHX-UHFFFAOYSA-N 0.000 description 1
- GKNDGSKQRCQQNU-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(4-nitrophenyl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 GKNDGSKQRCQQNU-UHFFFAOYSA-N 0.000 description 1
- BSJGRAZXJZXELO-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-phenylurea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC=C1 BSJGRAZXJZXELO-UHFFFAOYSA-N 0.000 description 1
- PIQKQKFAZMYOOC-UHFFFAOYSA-N 1-(4-benzyl-3-methyl-5-oxo-4h-imidazol-2-yl)-3-(3-chlorophenyl)urea Chemical compound O=C1NC(=NC(=O)NC=2C=C(Cl)C=CC=2)N(C)C1CC1=CC=CC=C1 PIQKQKFAZMYOOC-UHFFFAOYSA-N 0.000 description 1
- SIQXOHSXPPLXBG-UHFFFAOYSA-N 1-chloro-3-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(Cl)C(C)=C1N=C=O SIQXOHSXPPLXBG-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- GFFGYTMCNVMFAJ-UHFFFAOYSA-N 1-isocyanato-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(N=C=O)=C1 GFFGYTMCNVMFAJ-UHFFFAOYSA-N 0.000 description 1
- KQXILPLMOFQVBH-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)NC(=O)NC2N(CC(=O)N2C)C Chemical compound CC1=C(C(=CC=C1)C)NC(=O)NC2N(CC(=O)N2C)C KQXILPLMOFQVBH-UHFFFAOYSA-N 0.000 description 1
- NGIXEVWWCZSINJ-UHFFFAOYSA-N CCN1C(=O)CN=C1NC(=O)NC2=CC(=CC=C2)Cl Chemical compound CCN1C(=O)CN=C1NC(=O)NC2=CC(=CC=C2)Cl NGIXEVWWCZSINJ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- GANYMSDHMBJFIL-UHFFFAOYSA-N acetonitrile;ethoxyethane Chemical compound CC#N.CCOCC GANYMSDHMBJFIL-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- DNKYMRIVXIQCFO-UHFFFAOYSA-N benzene pentane Chemical compound CCCCC.CCCCC.C1=CC=CC=C1 DNKYMRIVXIQCFO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- QSACPWSIIRFHHR-UHFFFAOYSA-N dimethylphenyl isocyanide Natural products CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40802273A | 1973-10-19 | 1973-10-19 | |
| US40802273 | 1973-10-19 | ||
| US50879574A | 1974-09-23 | 1974-09-23 | |
| US50879574 | 1974-09-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI306574A7 FI306574A7 (enrdf_load_stackoverflow) | 1975-04-20 |
| FI59993B FI59993B (fi) | 1981-07-31 |
| FI59993C true FI59993C (fi) | 1981-11-10 |
Family
ID=27020109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3065/74A FI59993C (fi) | 1973-10-19 | 1974-10-18 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-oxo-2-imidazolidinylidenurinaemnen |
Country Status (22)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI800559A7 (fi) * | 1979-03-14 | 1981-01-01 | F Hoffmann La Roche & Co | Virtsa-ainejohdannaiset. |
| US4265900A (en) * | 1979-10-29 | 1981-05-05 | Mcneilab, Inc. | N-Aryl-N'-imidazol-2-ylureas |
| RS52883B (en) * | 2003-12-15 | 2014-02-28 | Merck Sharp & Dohme Corp. | HETEROCYCLIC ASPARTYL PROTEASE INHIBITORS |
| EP3653609B1 (en) | 2013-02-12 | 2024-04-03 | Buck Institute for Research on Aging | Hydantoins that modulate bace-mediated app processing |
-
1974
- 1974-10-14 DE DE19742448869 patent/DE2448869A1/de not_active Withdrawn
- 1974-10-15 SE SE7412959A patent/SE414173B/xx unknown
- 1974-10-15 BE BE149558A patent/BE821099A/xx unknown
- 1974-10-16 AR AR256117A patent/AR210320A1/es active
- 1974-10-17 RO RO197480253A patent/RO64926A/ro unknown
- 1974-10-17 IL IL45865A patent/IL45865A/xx unknown
- 1974-10-17 CH CH1395174A patent/CH614198A5/xx not_active IP Right Cessation
- 1974-10-18 HU HU74ME00001786A patent/HU170857B/hu unknown
- 1974-10-18 JP JP49119494A patent/JPS5077367A/ja active Pending
- 1974-10-18 NO NO743771A patent/NO141162C/no unknown
- 1974-10-18 AT AT840974A patent/AT348536B/de not_active IP Right Cessation
- 1974-10-18 GB GB45246/74A patent/GB1479909A/en not_active Expired
- 1974-10-18 IE IE2146/74A patent/IE40067B1/xx unknown
- 1974-10-18 NL NL7413718A patent/NL7413718A/xx not_active Application Discontinuation
- 1974-10-18 ES ES431153A patent/ES431153A1/es not_active Expired
- 1974-10-18 FI FI3065/74A patent/FI59993C/fi active
- 1974-10-18 YU YU2797/74A patent/YU36932B/xx unknown
- 1974-10-18 FR FR7435155A patent/FR2248042B1/fr not_active Expired
- 1974-10-18 DK DK548874A patent/DK548874A/da not_active Application Discontinuation
- 1974-10-18 CA CA211,775A patent/CA1043339A/en not_active Expired
- 1974-10-21 DD DD181808A patent/DD114079A5/xx unknown
- 1974-11-07 IN IN2451/CAL/74A patent/IN139447B/en unknown
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