SU460619A3 - Способ получени -(аминофенил) -алифатических карбоновых кислот - Google Patents
Способ получени -(аминофенил) -алифатических карбоновых кислотInfo
- Publication number
- SU460619A3 SU460619A3 SU1688519A SU1688519A SU460619A3 SU 460619 A3 SU460619 A3 SU 460619A3 SU 1688519 A SU1688519 A SU 1688519A SU 1688519 A SU1688519 A SU 1688519A SU 460619 A3 SU460619 A3 SU 460619A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- residue
- solution
- evaporated
- acid
- Prior art date
Links
- -1 aminophenyl Chemical group 0.000 title description 20
- 238000000034 method Methods 0.000 title description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- 239000000203 mixture Substances 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 22
- 230000008020 evaporation Effects 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RMXLHIUHKIVPAB-OWOJBTEDSA-N (e)-1,4-dibromobut-2-ene Chemical compound BrC\C=C\CBr RMXLHIUHKIVPAB-OWOJBTEDSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FQDIANVAWVHZIR-UPHRSURJSA-N (z)-1,4-dichlorobut-2-ene Chemical compound ClC\C=C/CCl FQDIANVAWVHZIR-UPHRSURJSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CFNDVXUTYPXOPG-UHFFFAOYSA-N ethyl 2-(4-aminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C=C1 CFNDVXUTYPXOPG-UHFFFAOYSA-N 0.000 description 2
- DWDRNKYLWMKWTH-UHFFFAOYSA-N ethyl 2-(4-nitrophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C([N+]([O-])=O)C=C1 DWDRNKYLWMKWTH-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- KYFVOFGTDCECTN-UHFFFAOYSA-M iron(2+) hydroxide nitrate Chemical compound [OH-].[N+](=O)([O-])[O-].[Fe+2] KYFVOFGTDCECTN-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- CSEWAUGPAQPMDC-UHFFFAOYSA-N 2-(4-aminophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1 CSEWAUGPAQPMDC-UHFFFAOYSA-N 0.000 description 1
- HHAWCKJIQFQNDU-UHFFFAOYSA-N 2-[4-(2,5-dihydropyrrol-1-yl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1N1CC=CC1 HHAWCKJIQFQNDU-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- MNPMLNAWAYZISG-UHFFFAOYSA-N C(C)OC(C(C)(C1=CC=CC=C1)N1CC=CC1)=O Chemical compound C(C)OC(C(C)(C1=CC=CC=C1)N1CC=CC1)=O MNPMLNAWAYZISG-UHFFFAOYSA-N 0.000 description 1
- DHSYHUWQVXIWPA-UHFFFAOYSA-N C(C)OC(C(C1=CC=C(C=C1)N1CC=CC1)CC)=O Chemical compound C(C)OC(C(C1=CC=C(C=C1)N1CC=CC1)CC)=O DHSYHUWQVXIWPA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- JRLLKLDNWBDTKN-UHFFFAOYSA-N ethyl 2-(4-acetamido-3-chlorophenyl)propanoate Chemical compound C(C)OC(C(C)C1=CC(=C(C=C1)NC(C)=O)Cl)=O JRLLKLDNWBDTKN-UHFFFAOYSA-N 0.000 description 1
- RAQHRNZSOAQGIK-UHFFFAOYSA-N ethyl 2-[4-(2,5-dihydropyrrol-1-yl)phenyl]acetate Chemical group C1=CC(CC(=O)OCC)=CC=C1N1CC=CC1 RAQHRNZSOAQGIK-UHFFFAOYSA-N 0.000 description 1
- NVJXVNWZEODSEW-UHFFFAOYSA-N ethyl 2-[4-(3,6-dihydro-2h-pyridin-1-yl)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1N1CC=CCC1 NVJXVNWZEODSEW-UHFFFAOYSA-N 0.000 description 1
- VWKGPFHYXWGWEI-UHFFFAOYSA-N ethyl 2-amino-2-phenylacetate Chemical compound CCOC(=O)C(N)C1=CC=CC=C1 VWKGPFHYXWGWEI-UHFFFAOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012074 organic phase Substances 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase 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
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84324469A | 1969-07-18 | 1969-07-18 | |
| CH1383069A CH574921A5 (en) | 1969-09-12 | 1969-09-12 | Anti-inflammatory alpha-aminophenyl carboxylic acids |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1413657A Division SU511850A3 (ru) | 1969-03-18 | 1970-03-17 | Способ получени -(аминофенил)алифатических карбоновых кислот |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU460619A3 true SU460619A3 (ru) | 1975-02-15 |
Family
ID=25713102
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1688519A SU460619A3 (ru) | 1969-07-18 | 1970-03-17 | Способ получени -(аминофенил) -алифатических карбоновых кислот |
| SU1703509A SU468400A3 (ru) | 1969-07-18 | 1970-03-17 | Способ получени (аминофенил)-алифатических производных карбоновых кислот или их солей,или их -окисей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1703509A SU468400A3 (ru) | 1969-07-18 | 1970-03-17 | Способ получени (аминофенил)-алифатических производных карбоновых кислот или их солей,или их -окисей |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPS5339433B1 (enExample) |
| AR (2) | AR195193A1 (enExample) |
| AT (3) | AT301532B (enExample) |
| BG (1) | BG17519A3 (enExample) |
| CS (2) | CS181677B2 (enExample) |
| SU (2) | SU460619A3 (enExample) |
| YU (19) | YU66470A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5935931U (ja) * | 1982-08-27 | 1984-03-06 | 菅谷 貞 | カメラのフイルムカウンタ |
-
1970
- 1970-03-17 SU SU1688519A patent/SU460619A3/ru active
- 1970-03-17 SU SU1703509A patent/SU468400A3/ru active
- 1970-03-17 AT AT111171A patent/AT301532B/de not_active IP Right Cessation
- 1970-03-17 YU YU66470A patent/YU66470A/xx unknown
- 1970-03-17 AT AT885471A patent/AT305998B/de not_active IP Right Cessation
- 1970-03-17 AT AT111071A patent/AT301531B/de not_active IP Right Cessation
- 1970-03-18 CS CS702673A patent/CS181677B2/cs unknown
- 1970-03-18 BG BG016945A patent/BG17519A3/xx unknown
- 1970-03-18 CS CS702970A patent/CS181680B2/cs unknown
- 1970-07-17 YU YU181870A patent/YU181870A/xx unknown
-
1972
- 1972-09-29 AR AR24436972A patent/AR195193A1/es active
- 1972-09-29 AR AR24437272A patent/AR195195A1/es active
-
1975
- 1975-09-03 JP JP10751675A patent/JPS5339433B1/ja active Pending
- 1975-09-03 JP JP10751975A patent/JPS5341152B1/ja active Pending
-
1977
- 1977-03-17 YU YU71477A patent/YU71477A/xx unknown
- 1977-03-17 YU YU71277A patent/YU71277A/xx unknown
- 1977-03-17 YU YU72177A patent/YU72177A/xx unknown
- 1977-03-17 YU YU71677A patent/YU71677A/xx unknown
- 1977-03-17 YU YU71577A patent/YU71577A/xx unknown
- 1977-03-17 YU YU72077A patent/YU72077A/xx unknown
- 1977-03-17 YU YU71977A patent/YU71977A/xx unknown
- 1977-03-17 YU YU71377A patent/YU71377A/xx unknown
- 1977-03-17 YU YU70977A patent/YU70977A/xx unknown
- 1977-03-17 YU YU72477A patent/YU72477A/xx unknown
- 1977-03-17 YU YU71777A patent/YU71777A/xx unknown
- 1977-03-17 YU YU71177A patent/YU71177A/xx unknown
- 1977-03-17 YU YU71877A patent/YU71877A/xx unknown
- 1977-03-17 YU YU72377A patent/YU72377A/xx unknown
- 1977-03-17 YU YU71077A patent/YU71077A/xx unknown
-
1982
- 1982-09-24 YU YU213182A patent/YU213182A/xx unknown
- 1982-09-24 YU YU213382A patent/YU213382A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU468400A3 (ru) | 1975-04-25 |
| YU71677A (en) | 1982-06-30 |
| YU71377A (en) | 1983-01-21 |
| SU442594A3 (ru) | 1974-09-05 |
| CS181677B2 (en) | 1978-03-31 |
| YU71477A (en) | 1982-06-30 |
| BG17519A3 (bg) | 1973-11-10 |
| CS181680B2 (en) | 1978-03-31 |
| YU72477A (en) | 1983-01-21 |
| AR195193A1 (es) | 1973-09-19 |
| YU71277A (en) | 1983-02-28 |
| YU72377A (en) | 1982-06-30 |
| AT305998B (de) | 1973-03-26 |
| YU181870A (en) | 1983-01-21 |
| YU71977A (en) | 1982-06-30 |
| YU70977A (en) | 1983-01-21 |
| JPS5339433B1 (enExample) | 1978-10-21 |
| AT301531B (de) | 1972-09-11 |
| YU213382A (en) | 1983-10-31 |
| YU71877A (en) | 1983-01-21 |
| YU71177A (en) | 1983-01-21 |
| YU71077A (en) | 1983-02-28 |
| AT301532B (de) | 1972-09-11 |
| YU71577A (en) | 1983-01-21 |
| YU72077A (en) | 1983-01-21 |
| YU66470A (en) | 1983-02-28 |
| YU213182A (en) | 1983-10-31 |
| YU71777A (en) | 1983-01-21 |
| JPS5341152B1 (enExample) | 1978-10-31 |
| AR195195A1 (es) | 1973-09-19 |
| YU72177A (en) | 1983-02-28 |
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