BE530119A - - Google Patents
Info
- Publication number
- BE530119A BE530119A BE530119DA BE530119A BE 530119 A BE530119 A BE 530119A BE 530119D A BE530119D A BE 530119DA BE 530119 A BE530119 A BE 530119A
- Authority
- BE
- Belgium
- Prior art keywords
- lower alkyl
- imidazolone
- alpha
- methyl
- acetal
- Prior art date
Links
- -1 mono-halo-phenyl Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000004202 carbamide Substances 0.000 claims description 14
- 150000003254 radicals Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IYGLNQREJHSNCL-UHFFFAOYSA-N C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(N(C=C1)C)=O Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(N(C=C1)C)=O IYGLNQREJHSNCL-UHFFFAOYSA-N 0.000 claims description 3
- WAVHIEUQFVRUHT-UHFFFAOYSA-N OC1=NC=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical class OC1=NC=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 WAVHIEUQFVRUHT-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating Effects 0.000 claims description 3
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 125000006177 alkyl benzyl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 241000209149 Zea Species 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- 239000003208 petroleum Substances 0.000 description 31
- 238000009835 boiling Methods 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000155 melt Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 238000007792 addition Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 7
- 150000001241 acetals Chemical class 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WZELXJBMMZFDDU-UHFFFAOYSA-N imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-N-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 4
- BNTDCSJFYZPOMC-UHFFFAOYSA-N N-ethyl-2,2-dimethoxyethanamine Chemical compound CCNCC(OC)OC BNTDCSJFYZPOMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- XGPXXSJFZSZULR-UHFFFAOYSA-N 1-isocyanatopropylbenzene Chemical compound O=C=NC(CC)C1=CC=CC=C1 XGPXXSJFZSZULR-UHFFFAOYSA-N 0.000 description 3
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 3
- SUIKMOVZRBDADL-UHFFFAOYSA-N COC(NC(C1=CC=CC=C1)C1=CC=CC=C1)(N(CC=O)C)OC Chemical compound COC(NC(C1=CC=CC=C1)C1=CC=CC=C1)(N(CC=O)C)OC SUIKMOVZRBDADL-UHFFFAOYSA-N 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- VSIMPIWSSKHLJK-UHFFFAOYSA-N 1-[isocyanato(phenyl)methyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(N=C=O)C1=CC=CC=C1 VSIMPIWSSKHLJK-UHFFFAOYSA-N 0.000 description 2
- LCPQMTUGLBIMHL-UHFFFAOYSA-N 1-benzhydryl-3-ethylimidazol-2-one Chemical compound O=C1N(CC)C=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LCPQMTUGLBIMHL-UHFFFAOYSA-N 0.000 description 2
- JJSCUXAFAJEQGB-UHFFFAOYSA-N 1-isocyanatoethylbenzene Chemical compound O=C=NC(C)C1=CC=CC=C1 JJSCUXAFAJEQGB-UHFFFAOYSA-N 0.000 description 2
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 2
- IGPOCNKINCDHKZ-UHFFFAOYSA-N BrC1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 Chemical compound BrC1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 IGPOCNKINCDHKZ-UHFFFAOYSA-N 0.000 description 2
- JPJXZDDQULUNQC-UHFFFAOYSA-N COC(N)(N)OC Chemical compound COC(N)(N)OC JPJXZDDQULUNQC-UHFFFAOYSA-N 0.000 description 2
- RNXOREWPZPQSOJ-UHFFFAOYSA-N COC1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 Chemical compound COC1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 RNXOREWPZPQSOJ-UHFFFAOYSA-N 0.000 description 2
- YLFVEJAVGTXRAC-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 Chemical compound ClC1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 YLFVEJAVGTXRAC-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BWLKKFSDKDJGDZ-UHFFFAOYSA-N [isocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)C1=CC=CC=C1 BWLKKFSDKDJGDZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- 101710028591 sam1 Proteins 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 1,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-Phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 1
- CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 description 1
- QGXMHCMPIAYMGT-UHFFFAOYSA-N 2-phenylbutanoyl chloride Chemical compound CCC(C(Cl)=O)C1=CC=CC=C1 QGXMHCMPIAYMGT-UHFFFAOYSA-N 0.000 description 1
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- JEVIEYZRIYPTPK-UHFFFAOYSA-N 4,4-diphenyl-1,3-oxazolidine-2,5-dione Chemical compound O=C1OC(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 JEVIEYZRIYPTPK-UHFFFAOYSA-N 0.000 description 1
- JMVQFRFKXOIRBI-UHFFFAOYSA-N 4-methylimidazol-2-one Chemical compound CC1=NC(=O)N=C1 JMVQFRFKXOIRBI-UHFFFAOYSA-N 0.000 description 1
- JFGXYIMVDHYWCW-UHFFFAOYSA-N C(C)C(C1=CC=CC=C1)N1C(N(C=C1)C)=O Chemical compound C(C)C(C1=CC=CC=C1)N1C(N(C=C1)C)=O JFGXYIMVDHYWCW-UHFFFAOYSA-N 0.000 description 1
- ILIHTGWFTSXJRO-UHFFFAOYSA-N C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(N(C=C1)C(CC)=O)=O Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(N(C=C1)C(CC)=O)=O ILIHTGWFTSXJRO-UHFFFAOYSA-N 0.000 description 1
- KDEVKILEHUBFCV-UHFFFAOYSA-N CCN(CC=O)C(NC(C1=CC=CC=C1)C1=CC=C(OC)C=C1)(OC)OC Chemical compound CCN(CC=O)C(NC(C1=CC=CC=C1)C1=CC=C(OC)C=C1)(OC)OC KDEVKILEHUBFCV-UHFFFAOYSA-N 0.000 description 1
- BDIXDEIBOUASIH-UHFFFAOYSA-N CCOC(NCC=O)(NC(C1=CC=CC=C1)C1=CC=C(Cl)C=C1)OCC Chemical compound CCOC(NCC=O)(NC(C1=CC=CC=C1)C1=CC=C(Cl)C=C1)OCC BDIXDEIBOUASIH-UHFFFAOYSA-N 0.000 description 1
- VAXSEHCLRWNUFK-UHFFFAOYSA-N CN1C=CN(C(C2=CC=CC=C2)C2=CC=C(C=C2)[N+]([O-])=O)C1=O Chemical compound CN1C=CN(C(C2=CC=CC=C2)C2=CC=C(C=C2)[N+]([O-])=O)C1=O VAXSEHCLRWNUFK-UHFFFAOYSA-N 0.000 description 1
- VRANYDMNWPDCHI-UHFFFAOYSA-N CN1C=CN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)C1=O Chemical compound CN1C=CN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)C1=O VRANYDMNWPDCHI-UHFFFAOYSA-N 0.000 description 1
- CGTRKAVNKIVWIU-UHFFFAOYSA-N COC(NC(C1=CC=C(C=C1)OC)C1=CC=CC=C1)(N(CC=O)C)OC Chemical compound COC(NC(C1=CC=C(C=C1)OC)C1=CC=CC=C1)(N(CC=O)C)OC CGTRKAVNKIVWIU-UHFFFAOYSA-N 0.000 description 1
- KIJJJSSNOQGNPS-UHFFFAOYSA-N COC(NC(C1=CC=CC=C1)CC)(N(CC=O)CC)OC Chemical compound COC(NC(C1=CC=CC=C1)CC)(N(CC=O)CC)OC KIJJJSSNOQGNPS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 241000152160 Ira Species 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N Isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XSANWVKVBMWAJI-UHFFFAOYSA-N [O-][N+](=O)C1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 Chemical compound [O-][N+](=O)C1=CC=C(C=C1)C(N=C=O)C1=CC=CC=C1 XSANWVKVBMWAJI-UHFFFAOYSA-N 0.000 description 1
- QNMQSTAQXWXXAS-UHFFFAOYSA-N [cyclohexyl(isocyanato)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)C1CCCCC1 QNMQSTAQXWXXAS-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000007864 aqueous solution Substances 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
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D233/70—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE530119A true BE530119A (ja) |
Family
ID=162872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE530119D BE530119A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE530119A (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0222664A2 (en) * | 1985-11-01 | 1987-05-20 | Merck & Co. Inc. | Novel cyclic ureas as dermal penetration enhancers |
-
0
- BE BE530119D patent/BE530119A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0222664A2 (en) * | 1985-11-01 | 1987-05-20 | Merck & Co. Inc. | Novel cyclic ureas as dermal penetration enhancers |
| EP0222664A3 (en) * | 1985-11-01 | 1988-03-30 | Merck & Co. Inc. | Novel cyclic ureas as dermal penetration enhancers |
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