CH626081A5 - Process for the preparation of 1-tert-alkyl-3-(substituted furyl) urea compounds - Google Patents
Process for the preparation of 1-tert-alkyl-3-(substituted furyl) urea compounds Download PDFInfo
- Publication number
- CH626081A5 CH626081A5 CH364777A CH364777A CH626081A5 CH 626081 A5 CH626081 A5 CH 626081A5 CH 364777 A CH364777 A CH 364777A CH 364777 A CH364777 A CH 364777A CH 626081 A5 CH626081 A5 CH 626081A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- methyl
- preparation
- tert
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003672 ureas Chemical class 0.000 title claims description 5
- 125000002541 furyl group Chemical group 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000007858 starting material Substances 0.000 claims abstract description 7
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 3
- 230000007017 scission Effects 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- -1 methyloxy, phenyl Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 235000013877 carbamide Nutrition 0.000 claims description 8
- 238000002955 isolation Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- IAODRFIZLKITMK-UHFFFAOYSA-N furan-2,3-dione Chemical compound O=C1OC=CC1=O IAODRFIZLKITMK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000011109 contamination Methods 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 230000036772 blood pressure Effects 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- SABBJFPNIAIRGR-UHFFFAOYSA-N 3-amino-2h-furan-5-one Chemical class NC1=CC(=O)OC1 SABBJFPNIAIRGR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 6
- 229940067157 phenylhydrazine Drugs 0.000 description 6
- IXOOBJLFCYIKSF-UHFFFAOYSA-N 3-amino-2-methyl-2h-furan-5-one Chemical compound CC1OC(=O)C=C1N IXOOBJLFCYIKSF-UHFFFAOYSA-N 0.000 description 5
- OPXIGKNSHMVEKG-UHFFFAOYSA-N 2-methyl-3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound CC1OC(=O)C=C1NNC1=CC=CC=C1 OPXIGKNSHMVEKG-UHFFFAOYSA-N 0.000 description 4
- QJDKEKAREQSWGS-UHFFFAOYSA-N 3-amino-4-methyl-2h-furan-5-one Chemical compound CC1=C(N)COC1=O QJDKEKAREQSWGS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- XYYGVTGRQFCJOF-UHFFFAOYSA-N 1-tert-butyl-3-(2-methyl-5-oxo-2h-furan-3-yl)urea Chemical compound CC1OC(=O)C=C1NC(=O)NC(C)(C)C XYYGVTGRQFCJOF-UHFFFAOYSA-N 0.000 description 3
- KPHAOJZGBJAKLI-UHFFFAOYSA-N 1-tert-butyl-3-(4-methyl-5-oxo-2h-furan-3-yl)urea Chemical compound CC1=C(NC(=O)NC(C)(C)C)COC1=O KPHAOJZGBJAKLI-UHFFFAOYSA-N 0.000 description 3
- LIFKUSYPFYXJOQ-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)hydrazinyl]-4-methyl-2h-furan-5-one Chemical compound C1OC(=O)C(C)=C1NNC1=CC=C(Cl)C=C1 LIFKUSYPFYXJOQ-UHFFFAOYSA-N 0.000 description 3
- FOTOFVUOURYGNI-UHFFFAOYSA-N 3-amino-2-ethyl-2h-furan-5-one Chemical compound CCC1OC(=O)C=C1N FOTOFVUOURYGNI-UHFFFAOYSA-N 0.000 description 3
- VEJKNMIKSYFETD-UHFFFAOYSA-N 4-methyl-3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound C1OC(=O)C(C)=C1NNC1=CC=CC=C1 VEJKNMIKSYFETD-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 3
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PMCRZTSZEWFKDR-UHFFFAOYSA-N 1-tert-butyl-3-(2-ethyl-5-oxo-2h-furan-3-yl)urea Chemical compound CCC1OC(=O)C=C1NC(=O)NC(C)(C)C PMCRZTSZEWFKDR-UHFFFAOYSA-N 0.000 description 2
- WQPWMAYLHFRFPP-UHFFFAOYSA-N 2-ethyl-3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical compound CCC1OC(=O)C=C1NNC1=CC=CC=C1 WQPWMAYLHFRFPP-UHFFFAOYSA-N 0.000 description 2
- AWGPWASAORSKKR-UHFFFAOYSA-N 3-methyloxolane-2,4-dione Chemical compound CC1C(=O)COC1=O AWGPWASAORSKKR-UHFFFAOYSA-N 0.000 description 2
- DZMHRWJWFDJBHD-UHFFFAOYSA-N 5-ethyloxolane-2,4-dione Chemical compound CCC1OC(=O)CC1=O DZMHRWJWFDJBHD-UHFFFAOYSA-N 0.000 description 2
- ZIQFRNVCLDSOAB-UHFFFAOYSA-N 5-methyloxolane-2,4-dione Chemical compound CC1OC(=O)CC1=O ZIQFRNVCLDSOAB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 description 1
- VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical compound CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 1
- XVXRHJRJIGTRIF-UHFFFAOYSA-N 3-(2-phenylhydrazinyl)-2h-furan-5-one Chemical class O=C1OCC(NNC=2C=CC=CC=2)=C1 XVXRHJRJIGTRIF-UHFFFAOYSA-N 0.000 description 1
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67007876A | 1976-03-24 | 1976-03-24 | |
| US76227377A | 1977-01-25 | 1977-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626081A5 true CH626081A5 (en) | 1981-10-30 |
Family
ID=27100248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH364777A CH626081A5 (en) | 1976-03-24 | 1977-03-23 | Process for the preparation of 1-tert-alkyl-3-(substituted furyl) urea compounds |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS52139056A (cs) |
| AR (1) | AR211956A1 (cs) |
| AT (1) | AT354460B (cs) |
| CA (1) | CA1097365A (cs) |
| CH (1) | CH626081A5 (cs) |
| DD (1) | DD130480A5 (cs) |
| DK (1) | DK143274C (cs) |
| ES (1) | ES457102A1 (cs) |
| FI (1) | FI770929A7 (cs) |
| GR (1) | GR62563B (cs) |
| HU (1) | HU173840B (cs) |
| LU (1) | LU77009A1 (cs) |
| NL (1) | NL7703155A (cs) |
| NO (1) | NO771021L (cs) |
| PT (1) | PT66336B (cs) |
| SE (1) | SE7702004L (cs) |
| SU (1) | SU625609A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO4970714A1 (es) * | 1997-09-05 | 2000-11-07 | Boehringer Mannheim Gmbh | Derivados ureido y tioureido de 4-amino-2(5h)-furanonas y 4-amino-2(5h) tiofenonas como agentes antitumorales |
-
1977
- 1977-02-23 SE SE7702004A patent/SE7702004L/xx not_active Application Discontinuation
- 1977-03-22 CA CA274,514A patent/CA1097365A/en not_active Expired
- 1977-03-22 AT AT199577A patent/AT354460B/de not_active IP Right Cessation
- 1977-03-22 ES ES457102A patent/ES457102A1/es not_active Expired
- 1977-03-22 PT PT66336A patent/PT66336B/pt unknown
- 1977-03-23 GR GR53079A patent/GR62563B/el unknown
- 1977-03-23 HU HU77DU263A patent/HU173840B/hu unknown
- 1977-03-23 NL NL7703155A patent/NL7703155A/xx not_active Application Discontinuation
- 1977-03-23 DK DK127977A patent/DK143274C/da active
- 1977-03-23 NO NO771021A patent/NO771021L/no unknown
- 1977-03-23 SU SU772463803A patent/SU625609A3/ru active
- 1977-03-23 CH CH364777A patent/CH626081A5/de not_active IP Right Cessation
- 1977-03-24 AR AR269971D patent/AR211956A1/es active
- 1977-03-24 FI FI770929A patent/FI770929A7/fi not_active Application Discontinuation
- 1977-03-24 JP JP3166277A patent/JPS52139056A/ja active Pending
- 1977-03-24 DD DD7700198044A patent/DD130480A5/xx unknown
- 1977-03-24 LU LU77009A patent/LU77009A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU625609A3 (ru) | 1978-09-25 |
| AT354460B (de) | 1979-01-10 |
| PT66336B (en) | 1978-08-16 |
| AR211956A1 (es) | 1978-04-14 |
| SE7702004L (sv) | 1977-09-25 |
| JPS52139056A (en) | 1977-11-19 |
| LU77009A1 (cs) | 1977-10-03 |
| GR62563B (en) | 1979-05-10 |
| DK143274B (da) | 1981-08-03 |
| NO771021L (no) | 1977-09-27 |
| DK143274C (da) | 1981-12-07 |
| FI770929A7 (cs) | 1977-09-25 |
| DK127977A (da) | 1977-09-25 |
| DD130480A5 (de) | 1978-04-05 |
| ES457102A1 (es) | 1978-08-16 |
| PT66336A (en) | 1977-04-01 |
| HU173840B (hu) | 1979-09-28 |
| CA1097365A (en) | 1981-03-10 |
| NL7703155A (nl) | 1977-09-27 |
| ATA199577A (de) | 1979-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3232672A1 (de) | (omega)-(4-(pyrid-2'-yl)-piperazin-1-yl)-alkylcarbonylanilide, verfahren und zwischenprodukte zu ihrer herstellung und die ersteren enthaltende arzneimittel | |
| EP0039844A2 (de) | Verfahren zur Herstellung von O-substituierten Derivaten des (+)-Cyanidan-3-ols | |
| CH493528A (de) | Verfahren zur Herstellung neuer substituierter Aminopyrimidine | |
| DE2845417C2 (cs) | ||
| EP0358595A1 (de) | N-Hetaryl-imidazolderivate | |
| CH634567A5 (de) | Verfahren zur herstellung von uracilderivaten. | |
| EP0380712A1 (de) | Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten | |
| DE1116221B (de) | Verfahren zur Herstellung von ªú¼ª-Pentamethylenbutyrolacton bzw. Salzen der 3,3-Pentamethylen-4-hydroxybuttersaeure | |
| DE2220256C3 (de) | N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselben | |
| DE3883891T2 (de) | Benzimidazol-Derivate und Verfahren zu deren Herstellung. | |
| DE2715785C2 (de) | Verfahren zur Herstellung von aromatischen oder heterocyclischen Hydroxylamino- oder Aminoverbindungen | |
| DE2065714A1 (de) | Neue benzodiazepinderivate | |
| CH626081A5 (en) | Process for the preparation of 1-tert-alkyl-3-(substituted furyl) urea compounds | |
| EP0004529B1 (de) | Tantomere Arylaminoimidazolinderivate, deren Herstellung und sie enthaltende Arzneimittel zur Bekämpfung von Schmerzzuständen | |
| DE2525852C2 (cs) | ||
| DE2752361A1 (de) | Neue indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE1817791C3 (de) | 2-Aminomethyl-3-phenylindole und ihre Salze mit Säuren | |
| DE1935671A1 (de) | 2-Aminomethylindole und ihre Salze | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| CH650772A5 (de) | Verfahren zur herstellung von pyrrolidin-2-onen aus 3-pyrrolin-2-onen und verfahren zur herstellung der 3-pyrrolin-2-on-ausgangsstoffe. | |
| DE1813241C3 (cs) | ||
| AT237623B (de) | Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten | |
| DE2628469A1 (de) | Gamma-aminoalkohole und verfahren zu ihrer herstellung | |
| AT268271B (de) | Verfahren zur Herstellung von neuen Imidazolcarboxylaten und ihren Salzen | |
| DE951364C (de) | Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |