SU419029A3 - Способ получения третичных аминокислотили их солей - Google Patents
Способ получения третичных аминокислотили их солейInfo
- Publication number
- SU419029A3 SU419029A3 SU1493628A SU1493628A SU419029A3 SU 419029 A3 SU419029 A3 SU 419029A3 SU 1493628 A SU1493628 A SU 1493628A SU 1493628 A SU1493628 A SU 1493628A SU 419029 A3 SU419029 A3 SU 419029A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ether
- chloro
- ethanol
- sulfuric
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 9
- 238000000034 method Methods 0.000 title description 3
- 150000001413 amino acids Chemical group 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 alkali metal cyanide Chemical class 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000284 extract Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- MRRWPCWICIRLDJ-UHFFFAOYSA-N [S].CCO Chemical compound [S].CCO MRRWPCWICIRLDJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GZDHVZCNDDAJPE-UHFFFAOYSA-N 3-chloro-4-morpholin-4-ylbenzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1N1CCOCC1 GZDHVZCNDDAJPE-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HPZLCXOOZSLFPW-UHFFFAOYSA-N methyl 4-morpholin-4-yl-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1N1CCOCC1 HPZLCXOOZSLFPW-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- GPXQKANEMLHMTK-UHFFFAOYSA-N 1-(3-chloro-4-piperidin-1-ylphenyl)-N,N-dimethylmethanamine Chemical compound CN(C)CC1=CC(=C(C=C1)N1CCCCC1)Cl GPXQKANEMLHMTK-UHFFFAOYSA-N 0.000 description 1
- DXGDUVKWYKPONA-UHFFFAOYSA-N 1-[2-chloro-4-(chloromethyl)phenyl]piperidine Chemical compound ClC1=CC(CCl)=CC=C1N1CCCCC1 DXGDUVKWYKPONA-UHFFFAOYSA-N 0.000 description 1
- KUUHZTPQGSAFLW-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylphenyl)acetic acid Chemical compound ClC=1C=C(C=CC1N1CCOCC1)CC(=O)O KUUHZTPQGSAFLW-UHFFFAOYSA-N 0.000 description 1
- WIZLBAWBLOXKCW-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylphenyl)acetonitrile Chemical compound ClC1=CC(CC#N)=CC=C1N1CCOCC1 WIZLBAWBLOXKCW-UHFFFAOYSA-N 0.000 description 1
- OAUICQGWQVBNOJ-UHFFFAOYSA-N 2-(3-chloro-4-piperidin-1-ylphenyl)acetonitrile Chemical compound ClC1=CC(CC#N)=CC=C1N1CCCCC1 OAUICQGWQVBNOJ-UHFFFAOYSA-N 0.000 description 1
- HSVFCSUZDDBOJW-UHFFFAOYSA-N 2-(3-piperidin-1-ylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(N2CCCCC2)=C1 HSVFCSUZDDBOJW-UHFFFAOYSA-N 0.000 description 1
- JCUCSMGLJLRTMT-UHFFFAOYSA-N 2-(4-morpholin-4-ylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1N1CCOCC1 JCUCSMGLJLRTMT-UHFFFAOYSA-N 0.000 description 1
- PKFJXCSNOKGOFC-UHFFFAOYSA-N 2-(4-piperidin-1-ylphenyl)acetonitrile Chemical compound C1=CC(CC#N)=CC=C1N1CCCCC1 PKFJXCSNOKGOFC-UHFFFAOYSA-N 0.000 description 1
- ZFNIWSXJLHQUHT-UHFFFAOYSA-N 2-(4-pyrrolidin-1-ylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1N1CCCC1 ZFNIWSXJLHQUHT-UHFFFAOYSA-N 0.000 description 1
- OZJNQHRPTQSJDF-UHFFFAOYSA-N 2-morpholin-4-yl-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)N1CCOCC1 OZJNQHRPTQSJDF-UHFFFAOYSA-N 0.000 description 1
- YXQFQHYAVDIHNM-UHFFFAOYSA-N 3-amino-4-morpholin-4-ylbenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1N1CCOCC1 YXQFQHYAVDIHNM-UHFFFAOYSA-N 0.000 description 1
- STYXVHJLERNGOJ-UHFFFAOYSA-N 3-chloro-4-piperidin-1-ylbenzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1N1CCCCC1 STYXVHJLERNGOJ-UHFFFAOYSA-N 0.000 description 1
- NSOINYDWBSICCH-UHFFFAOYSA-N 4-[2-chloro-4-(chloromethyl)phenyl]morpholine Chemical compound ClC1=CC(CCl)=CC=C1N1CCOCC1 NSOINYDWBSICCH-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- SREBONXEMNOUKV-UHFFFAOYSA-N 4-morpholino-3-nitrobenzoic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)O)=CC=C1N1CCOCC1 SREBONXEMNOUKV-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- USPZLHIREOKXLF-UHFFFAOYSA-N CC(C)O.[S] Chemical compound CC(C)O.[S] USPZLHIREOKXLF-UHFFFAOYSA-N 0.000 description 1
- HJBYCSKALCQJTM-UHFFFAOYSA-N CC(C1=CC=CC=C1)(C(=O)O)N2CCC(CC2)O Chemical compound CC(C1=CC=CC=C1)(C(=O)O)N2CCC(CC2)O HJBYCSKALCQJTM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QFHYHYSMAHUARD-UHFFFAOYSA-N [S].CO Chemical compound [S].CO QFHYHYSMAHUARD-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QMPBGXKGFCGWPA-UHFFFAOYSA-N methyl 3-amino-4-morpholin-4-ylbenzoate Chemical compound NC1=CC(C(=O)OC)=CC=C1N1CCOCC1 QMPBGXKGFCGWPA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- 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
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71634768A | 1968-03-27 | 1968-03-27 | |
US75713668A | 1968-09-03 | 1968-09-03 | |
US79086369A | 1969-01-13 | 1969-01-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU419029A3 true SU419029A3 (ru) | 1974-03-05 |
Family
ID=27418953
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1493628A SU419029A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислотили их солей |
SU1815022A SU459886A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получени -(аминофенил)алифатических карбоновых кислот или их солей |
SU1493629A SU421191A3 (ru) | 1968-03-27 | 1969-03-25 | СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ |
SU1493626A SU428600A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислот или их солей |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1815022A SU459886A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получени -(аминофенил)алифатических карбоновых кислот или их солей |
SU1493629A SU421191A3 (ru) | 1968-03-27 | 1969-03-25 | СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ АЛ1ИНОКИСЛОТ ИЛИ ИХ СЛОЖНЫХ ЭФИРОВ, или АМИДОВ, или их СОЛЕЙ |
SU1493626A SU428600A3 (ru) | 1968-03-27 | 1969-03-25 | Способ получения третичных аминокислот или их солей |
Country Status (26)
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2025518A1 (enrdf_load_stackoverflow) * | 1969-06-05 | 1970-12-10 | ||
DE2013376A1 (de) * | 1970-03-20 | 1971-10-07 | Merck Patent Gmbh | Substituierte Phenylessigsauren und Verfahren zu ihrer Herstellung |
-
1969
- 1969-02-17 CH CH1447071A patent/CH563986A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1447371A patent/CH563989A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1446871A patent/CH554859A/xx not_active IP Right Cessation
- 1969-02-17 CH CH1446771A patent/CH563984A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1396773A patent/CH559755A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1371573A patent/CH563985A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1446671A patent/CH563983A5/xx not_active IP Right Cessation
- 1969-02-17 CH CH1447271A patent/CH563988A5/xx not_active IP Right Cessation
- 1969-03-03 NL NL6903273.A patent/NL162647C/xx not_active IP Right Cessation
- 1969-03-18 DE DE19691913743 patent/DE1913743A1/de active Pending
- 1969-03-20 IL IL31861A patent/IL31861A/xx unknown
- 1969-03-24 SE SE6904047A patent/SE382812B/xx unknown
- 1969-03-25 SU SU1493628A patent/SU419029A3/ru active
- 1969-03-25 IE IE397/69A patent/IE33153B1/xx unknown
- 1969-03-25 SU SU1815022A patent/SU459886A3/ru active
- 1969-03-25 SU SU1493629A patent/SU421191A3/ru active
- 1969-03-25 FR FR6908705A patent/FR2004827A1/fr active Pending
- 1969-03-25 SU SU1493626A patent/SU428600A3/ru active
- 1969-03-25 PL PL13255169A patent/PL74820B1/pl unknown
- 1969-03-26 GB GB05859/69A patent/GB1268831A/en not_active Expired
- 1969-03-26 BE BE730520A patent/BE730520A/xx not_active IP Right Cessation
- 1969-03-26 AT AT281270A patent/AT291234B/de not_active IP Right Cessation
- 1969-03-26 AT AT281570A patent/AT291237B/de not_active IP Right Cessation
- 1969-03-26 FI FI690885A patent/FI52579C/fi active
- 1969-03-26 AT AT298169A patent/AT287685B/de active
- 1969-03-26 AT AT281970A patent/AT291241B/de not_active IP Right Cessation
- 1969-03-26 DK DK167569A patent/DK145226C/da not_active IP Right Cessation
- 1969-03-26 CY CY809A patent/CY809A/xx unknown
- 1969-03-26 AT AT281870A patent/AT291240B/de not_active IP Right Cessation
- 1969-03-26 AT AT281370A patent/AT291235B/de not_active IP Right Cessation
- 1969-03-26 NO NO1264/69A patent/NO132199C/no unknown
- 1969-03-26 AT AT281770A patent/AT291239B/de not_active IP Right Cessation
- 1969-03-26 AT AT282070A patent/AT291242B/de not_active IP Right Cessation
- 1969-03-27 RO RO6978690A patent/RO66269A/ro unknown
- 1969-03-27 CS CS726070A patent/CS153508B2/cs unknown
- 1969-03-27 RO RO59517A patent/RO61382A/ro unknown
- 1969-03-27 RO RO6979091A patent/RO66273A/ro unknown
- 1969-03-27 BG BG019310A patent/BG20339A3/xx unknown
- 1969-03-27 RO RO6978689A patent/RO64901A/ro unknown
- 1969-03-27 CS CS726370A patent/CS153511B2/cs unknown
- 1969-03-27 OA OA53565A patent/OA03609A/xx unknown
- 1969-03-27 CS CS726270A patent/CS153510B2/cs unknown
- 1969-03-27 CS CS725570A patent/CS153503B2/cs unknown
- 1969-03-27 BG BG019345A patent/BG20567A3/xx unknown
- 1969-03-27 CS CS725870A patent/CS153506B2/cs unknown
- 1969-03-27 CS CS725770A patent/CS153505B2/cs unknown
- 1969-03-27 BG BG019132A patent/BG20340A3/xx unknown
- 1969-03-27 CS CS220869A patent/CS153502B2/cs unknown
- 1969-03-27 CS CS725670A patent/CS153504B2/cs unknown
-
1970
- 1970-08-03 AR AR230412A patent/AR193194A1/es active
- 1970-08-03 AR AR230413A patent/AR193024A1/es active
- 1970-08-03 AR AR230415A patent/AR192699A1/es active
- 1970-08-03 AR AR230414A patent/AR192560A1/es active
- 1970-08-03 AR AR230419A patent/AR192864A1/es active
- 1970-08-03 AR AR230420A patent/AR193025A1/es active
-
1971
- 1971-05-13 AR AR235528A patent/AR194569A1/es active
-
1972
- 1972-03-23 JP JP2863972A patent/JPS5330712B1/ja active Pending
-
1973
- 1973-09-07 PH PH15001A patent/PH12640A/en unknown
-
1974
- 1974-07-17 YU YU2000/74A patent/YU39653B/xx unknown
- 1974-07-17 YU YU2001/74A patent/YU39926B/xx unknown
- 1974-08-22 CH CH238069A patent/CH566990A5/xx not_active IP Right Cessation
- 1974-11-01 CH CH238069A patent/CH563381A5/xx not_active IP Right Cessation
-
1975
- 1975-02-21 CH CH238069A patent/CH566991A5/xx not_active IP Right Cessation
- 1975-06-10 YU YU1499/75A patent/YU39532B/xx unknown
- 1975-07-10 KE KE2542*UA patent/KE2542A/xx unknown
- 1975-12-30 MY MY152/75A patent/MY7500152A/xx unknown
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