SU510470A1 - Способ получени производных уреидофеноксиалканоламина - Google Patents
Способ получени производных уреидофеноксиалканоламинаInfo
- Publication number
- SU510470A1 SU510470A1 SU1908717A SU1908717A SU510470A1 SU 510470 A1 SU510470 A1 SU 510470A1 SU 1908717 A SU1908717 A SU 1908717A SU 1908717 A SU1908717 A SU 1908717A SU 510470 A1 SU510470 A1 SU 510470A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenoxy
- hydroxy
- tert
- cyclohexylureido
- carbon atoms
- Prior art date
Links
- -1 ureidophenoxy Chemical group 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 4
- LJQGARKSJMMQBX-UHFFFAOYSA-N 2-methyl-n-propylpropan-2-amine Chemical compound CCCNC(C)(C)C LJQGARKSJMMQBX-UHFFFAOYSA-N 0.000 claims 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 239000001384 succinic acid Substances 0.000 claims 2
- QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 claims 1
- OXUBFNFJCLTHCF-UHFFFAOYSA-N 1-(hexylamino)propan-2-ol Chemical compound CCCCCCNCC(C)O OXUBFNFJCLTHCF-UHFFFAOYSA-N 0.000 claims 1
- RNFDZDMIFOFNMC-UHFFFAOYSA-N 1-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(C)O RNFDZDMIFOFNMC-UHFFFAOYSA-N 0.000 claims 1
- YUCNSPHIRYBLFF-UHFFFAOYSA-N 3-(3-methylbutylamino)propan-1-ol Chemical compound CC(C)CCNCCCO YUCNSPHIRYBLFF-UHFFFAOYSA-N 0.000 claims 1
- DFOAUWHTDKZVPW-UHFFFAOYSA-N 3-(cyclohexylamino)propan-1-ol Chemical compound OCCCNC1CCCCC1 DFOAUWHTDKZVPW-UHFFFAOYSA-N 0.000 claims 1
- PGOFJDZYVIIGGD-UHFFFAOYSA-N 3-(tert-butylamino)propan-1-ol Chemical compound CC(C)(C)NCCCO PGOFJDZYVIIGGD-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 235000007173 Abies balsamea Nutrition 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 241000218685 Tsuga Species 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- QNBOYTNTNXHZKH-UHFFFAOYSA-N butan-1-amine propane Chemical compound CCC.C(CCC)N QNBOYTNTNXHZKH-UHFFFAOYSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- VLSTXUUYLIALPB-UHFFFAOYSA-N n-propan-2-ylpropan-1-amine Chemical compound CCCNC(C)C VLSTXUUYLIALPB-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 230000002085 persistent effect Effects 0.000 claims 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- MXFWWQICDIZSOA-UHFFFAOYSA-N talinolol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=CC=C1NC(=O)NC1CCCCC1 MXFWWQICDIZSOA-UHFFFAOYSA-N 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MBHQWSSJIBMVIA-UHFFFAOYSA-N 1-(4-aminophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C(N)C=C1 MBHQWSSJIBMVIA-UHFFFAOYSA-N 0.000 description 1
- WWCSRBJGECHTEY-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]urea Chemical group C1=CC(OCC(O)CNC(C)C)=CC=C1NC(=O)NC1CCCCC1 WWCSRBJGECHTEY-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GZCPWFOPXIDRDP-UHFFFAOYSA-N 3-(propan-2-ylamino)propan-1-ol Chemical compound CC(C)NCCCO GZCPWFOPXIDRDP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003245 coal Substances 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- AXIFAUVPXCABHW-UHFFFAOYSA-N ethyl n-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(OCC(O)CNC(C)C)C=C1 AXIFAUVPXCABHW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical class [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- JPTWQLAZZAKCPR-UHFFFAOYSA-N phenyl N-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]carbamate Chemical compound O(C1=CC=CC=C1)C(=O)NC1=CC=C(OCC(CNC(C)C)O)C=C1 JPTWQLAZZAKCPR-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD15123670 | 1970-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU510470A1 true SU510470A1 (ru) | 1976-04-15 |
Family
ID=5483145
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1908717A SU510470A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU7101908715A SU580207A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU1714257A SU521262A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU1908721A SU511316A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU1908723A SU496268A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных урейдофеноксиалканоламина |
| SU1908719A SU504758A1 (ru) | 1970-11-13 | 1973-04-13 | Способ получени производных уреидофеноксиалканоламина |
| SU7301908722A SU578304A1 (ru) | 1970-11-13 | 1973-04-13 | Способ получени производных уреидофеноксиалканоламина |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7101908715A SU580207A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU1714257A SU521262A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU1908721A SU511316A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных уреидофеноксиалканоламина |
| SU1908723A SU496268A1 (ru) | 1970-11-13 | 1971-11-12 | Способ получени производных урейдофеноксиалканоламина |
| SU1908719A SU504758A1 (ru) | 1970-11-13 | 1973-04-13 | Способ получени производных уреидофеноксиалканоламина |
| SU7301908722A SU578304A1 (ru) | 1970-11-13 | 1973-04-13 | Способ получени производных уреидофеноксиалканоламина |
Country Status (13)
| Country | Link |
|---|---|
| BG (7) | BG20898A1 (en:Method) |
| CH (1) | CH565750A5 (en:Method) |
| CS (7) | CS177497B1 (en:Method) |
| DE (1) | DE2153024C3 (en:Method) |
| DK (1) | DK136712C (en:Method) |
| FI (1) | FI56374C (en:Method) |
| FR (1) | FR2113982A1 (en:Method) |
| HU (1) | HU172438B (en:Method) |
| PL (7) | PL95744B1 (en:Method) |
| RO (7) | RO63448A (en:Method) |
| SE (1) | SE373838B (en:Method) |
| SU (7) | SU510470A1 (en:Method) |
| YU (4) | YU36491B (en:Method) |
-
1971
- 1971-10-25 DE DE19712153024 patent/DE2153024C3/de not_active Expired
- 1971-10-27 CH CH1564971A patent/CH565750A5/xx not_active IP Right Cessation
- 1971-11-06 BG BG2093571A patent/BG20898A1/xx unknown
- 1971-11-06 BG BG2093971A patent/BG18958A1/xx unknown
- 1971-11-06 BG BG2093871A patent/BG18957A1/xx unknown
- 1971-11-06 BG BG2093771A patent/BG18956A1/xx unknown
- 1971-11-06 BG BG1894571A patent/BG20897A1/xx unknown
- 1971-11-06 BG BG2093471A patent/BG18955A1/xx unknown
- 1971-11-06 BG BG2093671A patent/BG19907A1/xx unknown
- 1971-11-09 RO RO7522071A patent/RO63448A/ro unknown
- 1971-11-09 RO RO7521871A patent/RO62905A/ro unknown
- 1971-11-09 RO RO7486571A patent/RO64022A/ro unknown
- 1971-11-09 RO RO7521971A patent/RO62906A/ro unknown
- 1971-11-09 RO RO7487271A patent/RO64200A/ro unknown
- 1971-11-09 RO RO6869271A patent/RO62250A/ro unknown
- 1971-11-09 RO RO7522171A patent/RO62907A/ro unknown
- 1971-11-10 CS CS801274A patent/CS177497B1/cs unknown
- 1971-11-10 CS CS801471A patent/CS177498B1/cs unknown
- 1971-11-10 CS CS801374A patent/CS183020B1/cs unknown
- 1971-11-10 CS CS801174A patent/CS177496B1/cs unknown
- 1971-11-10 CS CS801071A patent/CS177495B1/cs unknown
- 1971-11-10 CS CS801574A patent/CS177499B1/cs unknown
- 1971-11-10 CS CS787871A patent/CS177451B1/cs unknown
- 1971-11-11 PL PL17847071A patent/PL95744B1/pl unknown
- 1971-11-11 PL PL17846971A patent/PL95743B1/pl unknown
- 1971-11-11 HU HU71AE00000345A patent/HU172438B/hu unknown
- 1971-11-11 PL PL17846571A patent/PL95648B1/pl unknown
- 1971-11-11 PL PL17846671A patent/PL94028B1/pl unknown
- 1971-11-11 YU YU283671A patent/YU36491B/xx unknown
- 1971-11-11 PL PL17846771A patent/PL94027B1/pl unknown
- 1971-11-11 PL PL15149071A patent/PL89374B1/pl unknown
- 1971-11-11 DK DK551371A patent/DK136712C/da not_active IP Right Cessation
- 1971-11-11 PL PL17846871A patent/PL94076B1/pl unknown
- 1971-11-12 SE SE1455471A patent/SE373838B/xx unknown
- 1971-11-12 SU SU1908717A patent/SU510470A1/ru active
- 1971-11-12 SU SU7101908715A patent/SU580207A1/ru active
- 1971-11-12 SU SU1714257A patent/SU521262A1/ru active
- 1971-11-12 SU SU1908721A patent/SU511316A1/ru active
- 1971-11-12 SU SU1908723A patent/SU496268A1/ru active
- 1971-11-15 FR FR7140829A patent/FR2113982A1/fr active Granted
- 1971-11-15 FI FI325671A patent/FI56374C/fi active
-
1973
- 1973-04-13 SU SU1908719A patent/SU504758A1/ru active
- 1973-04-13 SU SU7301908722A patent/SU578304A1/ru active
-
1979
- 1979-02-20 YU YU41079A patent/YU41079A/xx unknown
- 1979-03-08 YU YU56479A patent/YU56479A/xx unknown
- 1979-03-15 YU YU62579A patent/YU62579A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2629736A (en) | Basically substituted n-alkyl derivatives of alpha, beta, beta-triarylpropionamides | |
| EP0171636A1 (en) | Pharmacologically active piperazino derivatives and the process for their preparation | |
| JPS6399043A (ja) | ジアミノエーテル類の製造法 | |
| CA1259329A (en) | PROCESS FOR PRODUCING N-SUBSTITUTED .alpha.-AMINO ACIDES | |
| US3647807A (en) | N-alkyl-1 4-dihydropyridines | |
| US3621043A (en) | N-substituted octadecadienoic acid amides as cholesterol lowering agents | |
| SU510470A1 (ru) | Способ получени производных уреидофеноксиалканоламина | |
| US2891066A (en) | 4,o-substituted phenyl 1 alkanol piperidines and esters thereof | |
| US3340298A (en) | Phenylalkanolamine derivatives | |
| PL80293B1 (en) | Phenyl esters of t-amcha[us3699149a] | |
| US5686625A (en) | Process for the preparation of N-substituted glycine acids or glycine esters and the use of the process for indigo synthesis | |
| EP0179408A2 (de) | Neue Amidoalkylmelamine und Aminoalkylmelamine und Verfahren zu ihrer Herstellung | |
| US2721211A (en) | Substituted phenylenediamines and process of preparing same | |
| EP0002066B1 (en) | 2-adamantyl hydrazines and pharmaceutical compositions containing them | |
| US2721207A (en) | Process for the production of amino diols and intermediate products utilized in said process | |
| US2951849A (en) | Hydrazine derivatives | |
| US3674806A (en) | 1,3,3,4,4-pentasubstituted pyrrolidines | |
| US3305549A (en) | Production of substituted biurets | |
| US3919310A (en) | Preparation of free sulfoximines by hydrolysis of N-(ortho- and para-nitrobenzoyl)-sulfoximines | |
| US2863863A (en) | Mercuration products of 1-pyridyl-3-allylureas | |
| US2923735A (en) | Process for the manufacture of derivatives of 4-hydroxy-isophthalic acid | |
| JPS60163851A (ja) | Ｎ‐置換α，β‐不飽和カルボン酸アミドの製造方法 | |
| US2662889A (en) | Tertiary-aminoalkyl 4-alkylamino-2-benzyloxybenzoates and debenzylation thereof | |
| US2674615A (en) | 1-arylcycloalkane 1-thiocar-boxylates | |
| US3096374A (en) | New carboxylic acid amides substituted at the nitrogen atom and beta-carbon atom and process for their manufacture |