GB997638A - Indole derivatives - Google Patents
Indole derivativesInfo
- Publication number
- GB997638A GB997638A GB10695/62A GB1069562A GB997638A GB 997638 A GB997638 A GB 997638A GB 10695/62 A GB10695/62 A GB 10695/62A GB 1069562 A GB1069562 A GB 1069562A GB 997638 A GB997638 A GB 997638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- prepared
- acid
- alkyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002475 indoles Chemical class 0.000 title abstract 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract 2
- -1 aromatic radical Chemical group 0.000 abstract 22
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 150000001408 amides Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 abstract 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 abstract 1
- OEHYXZZWECLGIA-UHFFFAOYSA-N 2,4-dimethylbenzenecarbothioyl chloride Chemical compound CC1=CC=C(C(Cl)=S)C(C)=C1 OEHYXZZWECLGIA-UHFFFAOYSA-N 0.000 abstract 1
- CPNZUBUZLOFWJZ-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-2-yl)acetaldehyde Chemical compound COC1=CC=C2NC(CC=O)=CC2=C1 CPNZUBUZLOFWJZ-UHFFFAOYSA-N 0.000 abstract 1
- NSERAHRFYKFCNH-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-2-yl)acetyl chloride Chemical compound COC1=CC=C2NC(CC(Cl)=O)=CC2=C1 NSERAHRFYKFCNH-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 abstract 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 230000009435 amidation Effects 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 150000001502 aryl halides Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 238000006480 benzoylation reaction Methods 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- XHTOMLSFAGLWMR-UHFFFAOYSA-N ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetate Chemical compound CC=1NC2=CC=C(C=C2C1C(C(=O)OCC)=O)OC XHTOMLSFAGLWMR-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000002337 glycosamines Chemical class 0.000 abstract 1
- OCDGBSUVYYVKQZ-UHFFFAOYSA-N gramine Chemical class C1=CC=C2C(CN(C)C)=CNC2=C1 OCDGBSUVYYVKQZ-UHFFFAOYSA-N 0.000 abstract 1
- GOERTRUXQHDLHC-UHFFFAOYSA-N gramine Natural products COC1=CC=C2NC=C(CN(C)C)C2=C1 GOERTRUXQHDLHC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000004031 phenylhydrazines Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9743461A | 1961-03-22 | 1961-03-22 | |
| US16461562A | 1962-01-05 | 1962-01-05 | |
| US28693563 US3161654A (en) | 1962-01-05 | 1963-06-11 | alpha-(1-aroyl-3-indolyl) alkanoic acids |
| US296451A US3201414A (en) | 1963-07-22 | 1963-07-22 | New 1-heteroacyl-3-indolyl aliphatic acids |
| US31047763A | 1963-09-20 | 1963-09-20 | |
| US31045463A | 1963-09-20 | 1963-09-20 | |
| US314503A US3242185A (en) | 1963-10-07 | 1963-10-07 | Lower aliphatic acids, salts and derivatives thereof |
| US32386363A | 1963-11-04 | 1963-11-04 | |
| US321328A US3275644A (en) | 1962-01-05 | 1963-11-04 | Certain 1-azolylindol-3-ylaliphatic acids |
| US321686A US3275645A (en) | 1962-01-05 | 1963-11-06 | N-(1-acyl-3-indolyl)-acids |
| US437338A US3338921A (en) | 1962-01-05 | 1965-01-26 | Thenoic and furoic acids |
| US442152A US3328423A (en) | 1962-01-05 | 1965-03-23 | alpha-(3-indolyl)-cyclopropyl lower aliphatic acids |
| US528020A US3316267A (en) | 1962-01-05 | 1966-02-15 | Indolyl acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB997638A true GB997638A (en) | 1965-07-07 |
Family
ID=27584499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10695/62A Expired GB997638A (en) | 1961-03-22 | 1962-03-20 | Indole derivatives |
Country Status (9)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228160A (en) | 1978-01-27 | 1980-10-14 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Inclusion complex of cyclodextrin and indomethacin and a process for the preparation thereof, method of use and pharmaceutical composition |
| WO2003022814A1 (fr) * | 2001-09-07 | 2003-03-20 | Ono Pharmaceutical Co., Ltd. | Derives d'indole |
| US7135495B2 (en) | 2000-03-09 | 2006-11-14 | Ono Pharmaceutical Co., Ltd. | Indole derivatives |
| CN113248419A (zh) * | 2021-06-09 | 2021-08-13 | 云南中医药大学 | 一种新型HuR抑制剂1-苯磺酰基-3-苯基吲哚-4,5-二酮的合成方法 |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| CN115417804A (zh) * | 2022-09-16 | 2022-12-02 | 天津药明康德新药开发有限公司 | 一种7-甲基-1h-吲哚-5-羧酸的合成方法 |
-
1962
- 1962-03-16 DE DE1795543A patent/DE1795543C3/de not_active Expired
- 1962-03-16 FI FI0561/62A patent/FI41158B/fi active
- 1962-03-16 DE DE1962M0070802 patent/DE1620030B1/de active Pending
- 1962-03-16 DE DE1962M0070803 patent/DE1620031B1/de active Pending
- 1962-03-20 GB GB10695/62A patent/GB997638A/en not_active Expired
- 1962-03-21 CH CH1737266A patent/CH445493A/de unknown
- 1962-03-21 CH CH1736766A patent/CH450419A/de unknown
- 1962-03-21 CH CH335362A patent/CH426822A/de unknown
- 1962-03-21 CH CH1737066A patent/CH445491A/de unknown
- 1962-03-21 SE SE11783/66A patent/SE315592B/xx unknown
- 1962-03-21 CH CH1736966A patent/CH445490A/de unknown
- 1962-03-21 CH CH1737166A patent/CH445492A/de unknown
- 1962-03-21 CH CH1737366A patent/CH449018A/de unknown
- 1962-03-21 CH CH1736866A patent/CH450420A/de unknown
-
1966
- 1966-05-25 DK DK268166AA patent/DK111959B/da unknown
- 1966-06-03 CY CY34866A patent/CY348A/xx unknown
- 1966-09-01 SE SE1178266A patent/SE314984B/xx unknown
- 1966-09-01 SE SE1178166A patent/SE315282B/xx unknown
- 1966-09-01 SE SE1178466A patent/SE315593B/xx unknown
- 1966-09-01 SE SE1178062A patent/SE315281B/xx unknown
- 1966-11-11 DK DK586366AA patent/DK120637B/da unknown
- 1966-11-11 DK DK586166AA patent/DK120340B/da unknown
- 1966-11-11 DK DK586266AA patent/DK116737B/da unknown
- 1966-12-28 FI FI3456/66A patent/FI41159B/fi active
- 1966-12-31 MY MY196692A patent/MY6600092A/xx unknown
-
1967
- 1967-02-13 DK DK77067AA patent/DK114975B/da unknown
-
1968
- 1968-04-01 NO NO1234/68A patent/NO135064C/no unknown
-
1969
- 1969-11-11 NO NO445869A patent/NO122372B/no unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228160A (en) | 1978-01-27 | 1980-10-14 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Inclusion complex of cyclodextrin and indomethacin and a process for the preparation thereof, method of use and pharmaceutical composition |
| US7135495B2 (en) | 2000-03-09 | 2006-11-14 | Ono Pharmaceutical Co., Ltd. | Indole derivatives |
| WO2003022814A1 (fr) * | 2001-09-07 | 2003-03-20 | Ono Pharmaceutical Co., Ltd. | Derives d'indole |
| US7291644B2 (en) | 2001-09-07 | 2007-11-06 | Ono Pharmaceuticals Co., Ltd. | Indole derivatives |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| CN113248419A (zh) * | 2021-06-09 | 2021-08-13 | 云南中医药大学 | 一种新型HuR抑制剂1-苯磺酰基-3-苯基吲哚-4,5-二酮的合成方法 |
| CN115417804A (zh) * | 2022-09-16 | 2022-12-02 | 天津药明康德新药开发有限公司 | 一种7-甲基-1h-吲哚-5-羧酸的合成方法 |
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