SU509219A3 - Способ получени индолкарбоновойкислоты или ее эфиров - Google Patents
Способ получени индолкарбоновойкислоты или ее эфировInfo
- Publication number
- SU509219A3 SU509219A3 SU1886348A SU1886348A SU509219A3 SU 509219 A3 SU509219 A3 SU 509219A3 SU 1886348 A SU1886348 A SU 1886348A SU 1886348 A SU1886348 A SU 1886348A SU 509219 A3 SU509219 A3 SU 509219A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- chloro
- carboxylic acid
- methyl
- methoxy
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 7
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 title claims 6
- 238000000034 method Methods 0.000 title claims 3
- 239000002253 acid Substances 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- -1 methyl-6-nitrophenyl Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 3
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 229940107700 pyruvic acid Drugs 0.000 claims 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 claims 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 claims 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 claims 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims 1
- UJBDTQSXJVUFTC-UHFFFAOYSA-N 4-methoxy-5-methyl-1h-indole-2-carboxylic acid Chemical compound COC1=C(C)C=CC2=C1C=C(C(O)=O)N2 UJBDTQSXJVUFTC-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- FHGPOPGCRIYJLE-UHFFFAOYSA-N 5-chloro-4-methyl-1h-indole-2-carboxylic acid Chemical compound CC1=C(Cl)C=CC2=C1C=C(C(O)=O)N2 FHGPOPGCRIYJLE-UHFFFAOYSA-N 0.000 claims 1
- 101000931108 Mus musculus DNA (cytosine-5)-methyltransferase 1 Proteins 0.000 claims 1
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 claims 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical class CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- HBPWZZBSVWZXTN-UHFFFAOYSA-N 1,2,3-trimethyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=C1C HBPWZZBSVWZXTN-UHFFFAOYSA-N 0.000 description 1
- CKFXYMTUUVNCIX-UHFFFAOYSA-N 3-methoxy-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(OC)=C(C(O)=O)NC2=C1 CKFXYMTUUVNCIX-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722203542 DE2203542A1 (de) | 1972-01-26 | 1972-01-26 | Blutzuckersenkende indolcarbonsaeurederivate und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU509219A3 true SU509219A3 (ru) | 1976-03-30 |
Family
ID=5834053
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1886348A SU509219A3 (ru) | 1972-01-26 | 1973-01-26 | Способ получени индолкарбоновойкислоты или ее эфиров |
| SU2056253A SU530642A3 (ru) | 1972-01-26 | 1974-08-30 | Способ получени производных индол-2-карбоновой кислоты или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2056253A SU530642A3 (ru) | 1972-01-26 | 1974-08-30 | Способ получени производных индол-2-карбоновой кислоты или их солей |
Country Status (25)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5579169A (en) * | 1978-12-12 | 1980-06-14 | Seiko Epson Corp | Ink jet type recorder |
| US4510157A (en) * | 1982-12-27 | 1985-04-09 | Ayerst, Mckenna & Harrison, Inc. | 6,7,8,9-Tetrahydro-1H-benz(g)indol-8-amine derivatives |
| US4470990A (en) * | 1983-03-14 | 1984-09-11 | Ayerst, Mckenna & Harrison Inc. | 6,7,8,9-Tetrahydronaphtho(1,2-B)furan-8-amine derivatives and their use as dopamine receptor stimulants |
| FR2768146B1 (fr) * | 1997-09-05 | 2000-05-05 | Oreal | Nouveaux composes de la famille des indole-carboxyliques et leur utilisation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3332846A (en) * | 1965-03-02 | 1967-07-25 | American Cyanamid Co | Method of inducing hypoglycemia with a substituted indole |
-
0
- BE BE794483D patent/BE794483A/xx not_active IP Right Cessation
-
1972
- 1972-01-26 DE DE19722203542 patent/DE2203542A1/de active Granted
-
1973
- 1973-01-21 IL IL41350A patent/IL41350A/xx unknown
- 1973-01-22 GB GB616774A patent/GB1369578A/en not_active Expired
- 1973-01-22 EG EG23/73A patent/EG10793A/xx active
- 1973-01-22 YU YU00174/73A patent/YU17473A/xx unknown
- 1973-01-22 CH CH85973A patent/CH586677A5/xx not_active IP Right Cessation
- 1973-01-22 GB GB318573A patent/GB1369577A/en not_active Expired
- 1973-01-22 DD DD168375A patent/DD103642A5/xx unknown
- 1973-01-22 AR AR246234A patent/AR194640A1/es active
- 1973-01-22 CH CH1530476A patent/CH587816A5/xx not_active IP Right Cessation
- 1973-01-22 NL NL737300871A patent/NL154420B/xx not_active IP Right Cessation
- 1973-01-23 AU AU51374/73A patent/AU465326B2/en not_active Expired
- 1973-01-23 FI FI177/73A patent/FI55829C/fi active
- 1973-01-24 FR FR7302419A patent/FR2169181B1/fr not_active Expired
- 1973-01-24 CS CS537A patent/CS164221B2/cs unknown
- 1973-01-24 CA CA161,918A patent/CA983511A/en not_active Expired
- 1973-01-24 CS CS8086*A patent/CS164222B2/cs unknown
- 1973-01-24 ES ES410934A patent/ES410934A1/es not_active Expired
- 1973-01-25 AT AT64073A patent/AT320634B/de not_active IP Right Cessation
- 1973-01-25 AT AT62074*7A patent/AT327885B/de active
- 1973-01-25 PL PL1973182916A patent/PL92384B1/pl unknown
- 1973-01-25 HU HUBO1411A patent/HU164871B/hu unknown
- 1973-01-25 ZA ZA730545A patent/ZA73545B/xx unknown
- 1973-01-25 NO NO307/73A patent/NO140007C/no unknown
- 1973-01-25 SE SE7301029A patent/SE388196B/xx unknown
- 1973-01-25 AT AT62074*A patent/ATA62074A/de unknown
- 1973-01-25 DK DK42173A patent/DK134517C/da active
- 1973-01-25 PL PL1973160407A patent/PL89093B1/pl unknown
- 1973-01-26 JP JP48010925A patent/JPS5930703B2/ja not_active Expired
- 1973-01-26 SU SU1886348A patent/SU509219A3/ru active
- 1973-07-12 AR AR249042A patent/AR195134A1/es active
-
1974
- 1974-08-30 SU SU2056253A patent/SU530642A3/ru active
-
1979
- 1979-07-23 YU YU01795/79A patent/YU179579A/xx unknown
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