SU520035A3 - Способ получени производных бензаламина или их солей - Google Patents
Способ получени производных бензаламина или их солейInfo
- Publication number
- SU520035A3 SU520035A3 SU2101049A SU2101049A SU520035A3 SU 520035 A3 SU520035 A3 SU 520035A3 SU 2101049 A SU2101049 A SU 2101049A SU 2101049 A SU2101049 A SU 2101049A SU 520035 A3 SU520035 A3 SU 520035A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- hydrochloride
- bromo
- diethylbenzylamine
- residue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- 150000003839 salts Chemical class 0.000 title claims 5
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical class N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- 230000008018 melting Effects 0.000 claims 7
- 238000002844 melting Methods 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 238000000354 decomposition reaction Methods 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- -1 benzyl halide Chemical class 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- 239000000741 silica gel Substances 0.000 claims 4
- 229910002027 silica gel Inorganic materials 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 3
- 239000012346 acetyl chloride Substances 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 235000019439 ethyl acetate Nutrition 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000007858 starting material Substances 0.000 claims 3
- CHRAJVQLWOMYQI-SCZZXKLOSA-N (1s,5r)-5,8,8-trimethyl-3-azabicyclo[3.2.1]octane Chemical group C1NC[C@H]2CC[C@]1(C)C2(C)C CHRAJVQLWOMYQI-SCZZXKLOSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001409 amidines Chemical class 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 150000003939 benzylamines Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 229910052736 halogen Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 229960004011 methenamine Drugs 0.000 claims 2
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- YZCDGFWKOILDHB-UHFFFAOYSA-N (1,5-diethylcyclohexa-2,4-dien-1-yl)methanamine Chemical compound C(C)C1(CN)CC(=CC=C1)CC YZCDGFWKOILDHB-UHFFFAOYSA-N 0.000 claims 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 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 claims 1
- QPRIOPMWGXBPOQ-JOCQHMNTSA-N O[C@H]1CC[C@@H](CC1)NCc1ccccc1 Chemical compound O[C@H]1CC[C@@H](CC1)NCc1ccccc1 QPRIOPMWGXBPOQ-JOCQHMNTSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 241001481789 Rupicapra Species 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- OHEDMAIVEXQCOZ-UHFFFAOYSA-N piperidine;dihydrochloride Chemical compound Cl.Cl.C1CCNCC1 OHEDMAIVEXQCOZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000006488 t-butyl benzyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/24—Camphidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742405322 DE2405322A1 (de) | 1974-02-05 | 1974-02-05 | Neue verfahren zur herstellung von benzylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU520035A3 true SU520035A3 (ru) | 1976-06-30 |
Family
ID=5906596
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2101049A SU520035A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензаламина или их солей |
| SU2101058A SU523634A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101064A SU528866A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU7502101047A SU575021A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU752101062A SU640657A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101060A SU527134A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101063A SU521838A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2101058A SU523634A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101064A SU528866A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU7502101047A SU575021A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU752101062A SU640657A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101060A SU527134A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
| SU2101063A SU521838A3 (ru) | 1974-02-05 | 1975-01-30 | Способ получени производных бензиламина или их солей |
Country Status (5)
| Country | Link |
|---|---|
| CH (7) | CH609036A5 (OSRAM) |
| DE (1) | DE2405322A1 (OSRAM) |
| ES (1) | ES433900A1 (OSRAM) |
| PL (7) | PL94232B1 (OSRAM) |
| SU (7) | SU520035A3 (OSRAM) |
-
1974
- 1974-02-05 DE DE19742405322 patent/DE2405322A1/de active Pending
- 1974-04-09 CH CH528977A patent/CH609036A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529477A patent/CH592609A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529177A patent/CH609038A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529077A patent/CH609037A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH528877A patent/CH609035A5/xx not_active IP Right Cessation
- 1974-04-09 CH CH529277A patent/CH609329A5/xx not_active IP Right Cessation
- 1974-04-12 PL PL18143674A patent/PL94232B1/pl unknown
- 1974-04-12 PL PL18143274A patent/PL94279B1/pl unknown
- 1974-04-12 PL PL18143174A patent/PL96532B1/pl unknown
- 1974-04-12 PL PL18143774A patent/PL94234B1/pl unknown
- 1974-04-12 PL PL18143574A patent/PL94231B1/pl unknown
- 1974-04-12 PL PL18143474A patent/PL95668B1/pl unknown
- 1974-04-12 PL PL18143374A patent/PL96785B1/pl unknown
-
1975
- 1975-01-17 ES ES433900A patent/ES433900A1/es not_active Expired
- 1975-01-30 SU SU2101049A patent/SU520035A3/ru active
- 1975-01-30 SU SU2101058A patent/SU523634A3/ru active
- 1975-01-30 SU SU2101064A patent/SU528866A3/ru active
- 1975-01-30 SU SU7502101047A patent/SU575021A3/ru active
- 1975-01-30 SU SU752101062A patent/SU640657A3/ru active
- 1975-01-30 SU SU2101060A patent/SU527134A3/ru active
- 1975-01-30 SU SU2101063A patent/SU521838A3/ru active
-
1977
- 1977-04-28 CH CH529377A patent/CH617662A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH609036A5 (en) | 1979-02-15 |
| CH592609A5 (OSRAM) | 1977-10-31 |
| PL94279B1 (OSRAM) | 1977-07-30 |
| PL94234B1 (OSRAM) | 1977-07-30 |
| CH609037A5 (en) | 1979-02-15 |
| PL96785B1 (pl) | 1978-01-31 |
| PL94232B1 (OSRAM) | 1977-07-30 |
| DE2405322A1 (de) | 1975-09-04 |
| ES433900A1 (es) | 1976-12-01 |
| SU521838A3 (ru) | 1976-07-15 |
| SU527134A3 (ru) | 1976-08-30 |
| SU640657A3 (ru) | 1978-12-30 |
| CH609329A5 (en) | 1979-02-28 |
| SU523634A3 (ru) | 1976-07-30 |
| SU575021A3 (ru) | 1977-09-30 |
| PL95668B1 (pl) | 1977-11-30 |
| PL94231B1 (OSRAM) | 1977-07-30 |
| CH609035A5 (en) | 1979-02-15 |
| CH609038A5 (en) | 1979-02-15 |
| PL96532B1 (pl) | 1977-12-31 |
| SU528866A3 (ru) | 1976-09-15 |
| CH617662A5 (en) | 1980-06-13 |
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