NO121210B - - Google Patents
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- Publication number
- NO121210B NO121210B NO158284A NO15828465A NO121210B NO 121210 B NO121210 B NO 121210B NO 158284 A NO158284 A NO 158284A NO 15828465 A NO15828465 A NO 15828465A NO 121210 B NO121210 B NO 121210B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- mixture
- urea
- ether
- product
- Prior art date
Links
- 239000004202 carbamide Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- -1 2,2-dichloro-1-methylcyclopropylacetyl chloride Chemical compound 0.000 claims description 11
- 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 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- XEZHXOZFNONJLU-UHFFFAOYSA-N 2,2-dichloro-1-phenylcyclopropane-1-carbonyl chloride Chemical compound C=1C=CC=CC=1C1(C(=O)Cl)CC1(Cl)Cl XEZHXOZFNONJLU-UHFFFAOYSA-N 0.000 claims description 2
- OJJYTODFFFMXNA-UHFFFAOYSA-N 2,2-dichlorocyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1CC1(Cl)Cl OJJYTODFFFMXNA-UHFFFAOYSA-N 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000009835 boiling Methods 0.000 description 22
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012259 ether extract Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229960004815 meprobamate Drugs 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZZQWHIVRLNQEDZ-UHFFFAOYSA-N 2,2-dibromocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1(Br)Br ZZQWHIVRLNQEDZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- KRHRPJKHUHTSDK-UHFFFAOYSA-N (2,2-dichlorocyclopropyl)methanol Chemical compound OCC1CC1(Cl)Cl KRHRPJKHUHTSDK-UHFFFAOYSA-N 0.000 description 2
- NLWCHSBIPUKUTF-UHFFFAOYSA-N 2,2-dibromocyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1CC1(Br)Br NLWCHSBIPUKUTF-UHFFFAOYSA-N 0.000 description 2
- AUVFGQDYJGWIJS-UHFFFAOYSA-N 2,2-dichloro-1-methylcyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1(C)CC1(Cl)Cl AUVFGQDYJGWIJS-UHFFFAOYSA-N 0.000 description 2
- KEZQSZUPYPHPKE-UHFFFAOYSA-N 2-(bromomethyl)-1,1-dichlorocyclopropane Chemical compound ClC1(Cl)CC1CBr KEZQSZUPYPHPKE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- ATTLDOZXPZCOGK-UHFFFAOYSA-N (2-phenylcyclopropyl)methanamine Chemical compound NCC1CC1C1=CC=CC=C1 ATTLDOZXPZCOGK-UHFFFAOYSA-N 0.000 description 1
- AVVMSHVXSGLTEZ-UHFFFAOYSA-N (2-phenylcyclopropyl)urea Chemical compound NC(=O)NC1CC1C1=CC=CC=C1 AVVMSHVXSGLTEZ-UHFFFAOYSA-N 0.000 description 1
- PMZBTQHSPQUSAV-UHFFFAOYSA-N 1,1-dibromo-2-ethenyl-2-methylcyclopropane Chemical compound C=CC1(C)CC1(Br)Br PMZBTQHSPQUSAV-UHFFFAOYSA-N 0.000 description 1
- RTBUVGWEJCPSFF-UHFFFAOYSA-N 1,1-dibromo-2-ethenylcyclopropane Chemical compound BrC1(Br)CC1C=C RTBUVGWEJCPSFF-UHFFFAOYSA-N 0.000 description 1
- GAAAGAHNGGKSQH-UHFFFAOYSA-N 1,1-dichloro-2-ethenylcyclopropane Chemical compound ClC1(Cl)CC1C=C GAAAGAHNGGKSQH-UHFFFAOYSA-N 0.000 description 1
- HZSXCMNVIABPFO-UHFFFAOYSA-N 1-cyclopropyl-1-phenylurea Chemical class C=1C=CC=CC=1N(C(=O)N)C1CC1 HZSXCMNVIABPFO-UHFFFAOYSA-N 0.000 description 1
- GVGFEJPTKINGLP-UHFFFAOYSA-N 2,2-dichlorocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1(Cl)Cl GVGFEJPTKINGLP-UHFFFAOYSA-N 0.000 description 1
- WYBGYUVVQBMZJQ-UHFFFAOYSA-N 2-(2,2-dichloro-1-methylcyclopropyl)acetic acid Chemical compound OC(=O)CC1(C)CC1(Cl)Cl WYBGYUVVQBMZJQ-UHFFFAOYSA-N 0.000 description 1
- FVVDYMMSTXTQKI-UHFFFAOYSA-N 2-(2,2-dichlorocyclopropyl)acetic acid Chemical compound OC(=O)CC1CC1(Cl)Cl FVVDYMMSTXTQKI-UHFFFAOYSA-N 0.000 description 1
- BELYRRZZXNBKRI-UHFFFAOYSA-N 2-(2,2-dichlorocyclopropyl)acetyl chloride Chemical compound ClC(=O)CC1CC1(Cl)Cl BELYRRZZXNBKRI-UHFFFAOYSA-N 0.000 description 1
- IOWKRFFHXWDUIS-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxamide Chemical class NC(=O)C1CC1C1=CC=CC=C1 IOWKRFFHXWDUIS-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VXWCDIJTBDQWJQ-UHFFFAOYSA-N N-carbamoyl-2,2-dichloro-1-methylcyclopropane-1-carboxamide Chemical compound ClC1(C(C1)(C(=O)NC(=O)N)C)Cl VXWCDIJTBDQWJQ-UHFFFAOYSA-N 0.000 description 1
- LEIQYJHEAVFNOO-UHFFFAOYSA-N N-carbamoyl-2,2-dichlorocyclopropane-1-carboxamide Chemical compound ClC1(C(C1)C(=O)NC(=O)N)Cl LEIQYJHEAVFNOO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005187 foaming Methods 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
- 230000000147 hypnotic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- OCHYJSATRBHPLB-UHFFFAOYSA-N n-phenylcyclopropanecarboxamide Chemical class C1CC1C(=O)NC1=CC=CC=C1 OCHYJSATRBHPLB-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/44—Halogenated alcohols containing saturated rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22579/64A GB1033517A (en) | 1964-06-01 | 1964-06-01 | Improvements in or relating to 1-(cyclopropylcarbonyl) ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121210B true NO121210B (de) | 1971-02-01 |
Family
ID=10181696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO158284A NO121210B (de) | 1964-06-01 | 1965-05-31 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3301896A (de) |
| BE (1) | BE664781A (de) |
| BR (1) | BR6570102D0 (de) |
| CH (1) | CH450400A (de) |
| DE (1) | DE1234711B (de) |
| DK (1) | DK119459B (de) |
| FR (1) | FR1462985A (de) |
| GB (1) | GB1033517A (de) |
| NL (1) | NL6506881A (de) |
| NO (1) | NO121210B (de) |
| SE (1) | SE314674B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627778A (en) * | 1967-08-19 | 1971-12-14 | Schering Ag | N- and n{40 -substituted n-bromoacetyl ureas |
| NZ190994A (en) | 1978-07-24 | 1981-10-19 | Merck & Co Inc | Z-2-acylamino-3-monosubstituted propenoates |
| HU184062B (en) * | 1979-10-19 | 1984-06-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted acyl urea |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3129246A (en) * | 1961-06-23 | 1964-04-14 | Dow Chemical Co | 3, 5-dinitrobenzoylureas |
-
0
- BE BE664781D patent/BE664781A/xx unknown
-
1964
- 1964-06-01 GB GB22579/64A patent/GB1033517A/en not_active Expired
-
1965
- 1965-05-26 FR FR18460A patent/FR1462985A/fr not_active Expired
- 1965-05-28 US US459889A patent/US3301896A/en not_active Expired - Lifetime
- 1965-05-31 NO NO158284A patent/NO121210B/no unknown
- 1965-05-31 DE DEB82184A patent/DE1234711B/de active Pending
- 1965-05-31 NL NL6506881A patent/NL6506881A/xx unknown
- 1965-06-01 DK DK276765AA patent/DK119459B/da unknown
- 1965-06-01 BR BR170102/65A patent/BR6570102D0/pt unknown
- 1965-06-01 CH CH761665A patent/CH450400A/de unknown
- 1965-06-01 SE SE7131/65A patent/SE314674B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3301896A (en) | 1967-01-31 |
| FR1462985A (fr) | 1966-12-23 |
| NL6506881A (de) | 1965-12-02 |
| CH450400A (de) | 1968-01-31 |
| BR6570102D0 (pt) | 1973-04-26 |
| SE314674B (de) | 1969-09-15 |
| DK119459B (da) | 1971-01-11 |
| BE664781A (de) | |
| DE1234711B (de) | 1967-02-23 |
| GB1033517A (en) | 1966-06-22 |
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