CH523248A - Verfahren zur Herstellung neuartiger antiphlogistischer und anticholesterolemischer, in 3-Stellung durch eine aliphatische Gruppe substituierter Indole von niederer Toxizität - Google Patents

Verfahren zur Herstellung neuartiger antiphlogistischer und anticholesterolemischer, in 3-Stellung durch eine aliphatische Gruppe substituierter Indole von niederer Toxizität

Info

Publication number: CH523248A
Authority: CH; Switzerland
Prior art keywords: acid; group; phenoxyacetyl; methyl; formula
Prior art date: 1966-06-10

Application number

CH820467A

Other languages

German (de)

English (en)

Inventor

Yamamoto Hisao

Nakamura Yasushi

Nakao Masaru

Kobayashi Tsuyoshi

Original Assignee

Sumitomo Chemical Co

Priority date (The priority date 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 date listed.)

1966-06-10

Filing date

1967-06-10

Publication date

1972-05-31

1967-06-10 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1972-05-31 Publication of CH523248A publication Critical patent/CH523248A/de

Links

150000002475 indoles Chemical class 0.000 title description 4
229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
-1 benzyloxy, tetrahydropyranyloxy Chemical group 0.000 claims abstract description 87
230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 38
238000000034 method Methods 0.000 claims description 31
150000007857 hydrazones Chemical class 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 16
230000002484 anti-cholesterolemic effect Effects 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
231100000053 low toxicity Toxicity 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 4
239000002221 antipyretic Substances 0.000 abstract description 4
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
230000001754 anti-pyretic effect Effects 0.000 abstract description 3
230000000259 anti-tumor effect Effects 0.000 abstract description 3
230000000855 fungicidal effect Effects 0.000 abstract description 3
150000002367 halogens Chemical class 0.000 abstract description 3
239000000730 antalgic agent Substances 0.000 abstract description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
239000003529 anticholesteremic agent Substances 0.000 abstract 1
230000003236 psychic effect Effects 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
238000002844 melting Methods 0.000 description 37
230000008018 melting Effects 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
239000000203 mixture Substances 0.000 description 25
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
239000013078 crystal Substances 0.000 description 22
150000004031 phenylhydrazines Chemical class 0.000 description 22
235000019441 ethanol Nutrition 0.000 description 17
239000002904 solvent Substances 0.000 description 17
229960000583 acetic acid Drugs 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 13
235000011054 acetic acid Nutrition 0.000 description 12
238000004452 microanalysis Methods 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 10
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
239000002244 precipitate Substances 0.000 description 9
AQWPFVMWKYADAH-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-1-(2-phenoxyacetyl)indol-3-yl]acetic acid Chemical compound O(C1=CC=CC=C1)CC(=O)N1C(=C(C2=CC(=CC=C12)OC)CC(=O)O)C AQWPFVMWKYADAH-UHFFFAOYSA-N 0.000 description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
235000019260 propionic acid Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
150000007522 mineralic acids Chemical class 0.000 description 5
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000008096 xylene Substances 0.000 description 5
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229960002895 phenylbutazone Drugs 0.000 description 4
239000012286 potassium permanganate Substances 0.000 description 4
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
MBBOMCVGYCRMEA-UHFFFAOYSA-N tryptophol Chemical class C1=CC=C2C(CCO)=CNC2=C1 MBBOMCVGYCRMEA-UHFFFAOYSA-N 0.000 description 4
235000005074 zinc chloride Nutrition 0.000 description 4
239000011592 zinc chloride Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
230000000740 bleeding effect Effects 0.000 description 3
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
239000012024 dehydrating agents‎ Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
150000002429 hydrazines Chemical class 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
229940040102 levulinic acid Drugs 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910001507 metal halide Inorganic materials 0.000 description 3
150000005309 metal halides Chemical class 0.000 description 3
239000012454 non-polar solvent Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
239000007858 starting material Substances 0.000 description 3
NEQWAHHMTOUABY-UHFFFAOYSA-N 2-(2-oxopropyl)propanedioic acid Chemical compound CC(=O)CC(C(O)=O)C(O)=O NEQWAHHMTOUABY-UHFFFAOYSA-N 0.000 description 2
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 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JGZOYTLMNHVXBF-UHFFFAOYSA-N ClC1=CC=C(OCC(=O)N2C(=C(C3=CC(=CC=C23)OC)CC(=O)O)C)C=C1 Chemical compound ClC1=CC=C(OCC(=O)N2C(=C(C3=CC(=CC=C23)OC)CC(=O)O)C)C=C1 JGZOYTLMNHVXBF-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
239000005750 Copper hydroxide Substances 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
208000035150 Hypercholesterolemia Diseases 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
QVRKLZVEAOHVTM-UHFFFAOYSA-N N-(4-methoxyphenyl)-2-phenoxyacetohydrazide hydrochloride Chemical compound Cl.O(C1=CC=CC=C1)CC(=O)N(N)C1=CC=C(C=C1)OC QVRKLZVEAOHVTM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
YJJWIVCWMNTBCL-UHFFFAOYSA-N O(C1=CC=CC=C1)CC(=O)N(N)C1=CC(=CC=C1)OC Chemical compound O(C1=CC=CC=C1)CC(=O)N(N)C1=CC(=CC=C1)OC YJJWIVCWMNTBCL-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000003627 anti-cholesterol Effects 0.000 description 2
229940124599 anti-inflammatory drug Drugs 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229910001956 copper hydroxide Inorganic materials 0.000 description 2
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000843 powder Substances 0.000 description 2
229910001923 silver oxide Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
231100001274 therapeutic index Toxicity 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
CRKDNNLDFYKBEE-RMKNXTFCSA-N (e)-benzylidenehydrazine Chemical compound N\N=C\C1=CC=CC=C1 CRKDNNLDFYKBEE-RMKNXTFCSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 description 1
DHBPCLVYRILLIN-UHFFFAOYSA-N 2-(2,3-dihydro-1h-indol-3-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)CNC2=C1 DHBPCLVYRILLIN-UHFFFAOYSA-N 0.000 description 1
DBOGTKNFUYCYKE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-N-(4-methoxyphenyl)acetohydrazide hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)N(N)C(=O)COC1=CC=C(Cl)C=C1 DBOGTKNFUYCYKE-UHFFFAOYSA-N 0.000 description 1
UADKDQMKSIZFCV-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-1-(2-phenoxyacetyl)-2,3-dihydroindol-3-yl]acetic acid Chemical compound O(C1=CC=CC=C1)CC(=O)N1C(C(C2=CC(=CC=C12)OC)CC(=O)O)C UADKDQMKSIZFCV-UHFFFAOYSA-N 0.000 description 1
SFGXGUPNFNITAS-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-1-(3-phenylpropanethioyl)indol-3-yl]acetic acid Chemical compound C1(=CC=CC=C1)CCC(=S)N1C(=C(C2=CC(=CC=C12)OC)CC(=O)O)C SFGXGUPNFNITAS-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
FHSUFDYFOHSYHI-UHFFFAOYSA-N 3-oxopentanoic acid Chemical compound CCC(=O)CC(O)=O FHSUFDYFOHSYHI-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
MMPJSUFZVKPTIU-UHFFFAOYSA-N COC(C=C1)=CC=C1N(C(CCC(O)=O)C=O)C(COC1=CC=CC=C1)=O Chemical compound COC(C=C1)=CC=C1N(C(CCC(O)=O)C=O)C(COC1=CC=CC=C1)=O MMPJSUFZVKPTIU-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
SLVLZLKGXLEKMF-UHFFFAOYSA-N Cl.C(C)(C)(C)C1=CC=C(OCC(=O)N(N)C2=CC=C(C=C2)OC)C=C1 Chemical compound Cl.C(C)(C)(C)C1=CC=C(OCC(=O)N(N)C2=CC=C(C=C2)OC)C=C1 SLVLZLKGXLEKMF-UHFFFAOYSA-N 0.000 description 1
ZYMWKXAMYWAAJX-UHFFFAOYSA-N Cl.O(C1=CC=CC=C1)CC(=N)N(N)C1=CC=C(C=C1)OC Chemical compound Cl.O(C1=CC=CC=C1)CC(=N)N(N)C1=CC=C(C=C1)OC ZYMWKXAMYWAAJX-UHFFFAOYSA-N 0.000 description 1
238000006641 Fischer synthesis reaction Methods 0.000 description 1
206010017815 Gastric perforation Diseases 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
OSBRRBGGLHRCNW-UHFFFAOYSA-N Hydrazone-Acetone Natural products CC(=O)N=N OSBRRBGGLHRCNW-UHFFFAOYSA-N 0.000 description 1
DKEGGFXVQFWOLW-UHFFFAOYSA-N Hydrazone-Acetophenone Natural products N=NC(C)C1=CC=CC=C1 DKEGGFXVQFWOLW-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
BKWYSJOJSIEKOY-UHFFFAOYSA-N N-(4-methoxyphenyl)-2-phenoxyacetohydrazide Chemical compound O(C1=CC=CC=C1)CC(=O)N(N)C1=CC=C(C=C1)OC BKWYSJOJSIEKOY-UHFFFAOYSA-N 0.000 description 1
ULCPZXMJYBSKGJ-UHFFFAOYSA-N N-(4-methylphenyl)-2-phenoxyacetohydrazide Chemical compound O(C1=CC=CC=C1)CC(=O)N(N)C1=CC=C(C=C1)C ULCPZXMJYBSKGJ-UHFFFAOYSA-N 0.000 description 1
TXWGINUZLBAKDF-UHFFFAOYSA-N N-Deschlorobenzoyl indomethacin Chemical compound COC1=CC=C2NC(C)=C(CC(O)=O)C2=C1 TXWGINUZLBAKDF-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
HWACYKBQCDCMJJ-UHFFFAOYSA-N O(C1=CC=CC=C1)CC(=O)N1C(=C(C2=CC(=CC=C12)OC)CC=O)C Chemical compound O(C1=CC=CC=C1)CC(=O)N1C(=C(C2=CC(=CC=C12)OC)CC=O)C HWACYKBQCDCMJJ-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000000326 anti-hypercholesterolaemic effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000037406 food intake Effects 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
WHOOUMGHGSPMGR-UHFFFAOYSA-N indol-3-ylacetaldehyde Chemical class C1=CC=C2C(CC=O)=CNC2=C1 WHOOUMGHGSPMGR-UHFFFAOYSA-N 0.000 description 1
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
LIRDJALZRPAZOR-UHFFFAOYSA-N indolin-3-one Chemical class C1=CC=C2C(=O)CNC2=C1 LIRDJALZRPAZOR-UHFFFAOYSA-N 0.000 description 1
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
206010022694 intestinal perforation Diseases 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
LVSSYINVRUSJDA-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-phenoxyacetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)COC1=CC=CC=C1 LVSSYINVRUSJDA-UHFFFAOYSA-N 0.000 description 1
JKTLJMSCIJYDAN-UHFFFAOYSA-N n-(ethylideneamino)-4-methoxyaniline Chemical compound COC1=CC=C(NN=CC)C=C1 JKTLJMSCIJYDAN-UHFFFAOYSA-N 0.000 description 1
NOOJOVSUISWZIV-UHFFFAOYSA-N n-ethylaniline;pyridine Chemical compound C1=CC=NC=C1.CCNC1=CC=CC=C1 NOOJOVSUISWZIV-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
CELWCAITJAEQNL-UHFFFAOYSA-N oxan-2-ol Chemical compound OC1CCCCO1 CELWCAITJAEQNL-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- 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
- 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
- C07D209/26—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 with an acyl radical attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B19/00—Liquid-phase epitaxial-layer growth
- C30B19/02—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux
- C30B19/04—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux the solvent being a component of the crystal composition
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B19/00—Liquid-phase epitaxial-layer growth
- C30B19/06—Reaction chambers; Boats for supporting the melt; Substrate holders
- C30B19/061—Tipping system, e.g. by rotation
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/10—Inorganic compounds or compositions
- C30B29/40—AIIIBV compounds wherein A is B, Al, Ga, In or Tl and B is N, P, As, Sb or Bi
- C30B29/42—Gallium arsenide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Crystallography & Structural Chemistry (AREA)
Materials Engineering (AREA)
Metallurgy (AREA)
Medicinal Chemistry (AREA)
Inorganic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH820467A 1966-06-10 1967-06-10 Verfahren zur Herstellung neuartiger antiphlogistischer und anticholesterolemischer, in 3-Stellung durch eine aliphatische Gruppe substituierter Indole von niederer Toxizität CH523248A (de)

Applications Claiming Priority (13)

Application Number	Priority Date	Filing Date
JP3762866		1966-06-10
JP4272066		1966-06-30
JP4272266		1966-06-30
JP4806266		1966-07-21
JP205967		1967-01-10
JP205867		1967-01-10
JP237067		1967-01-11
JP261867		1967-01-13
JP1332867		1967-03-01
JP1332967		1967-03-01
JP1434767		1967-03-06
JP1434667		1967-03-06
FR109823A FR6774M (cs)	1966-06-10	1967-06-09

Publications (1)

Publication Number	Publication Date
CH523248A true CH523248A (de)	1972-05-31

Family

ID=27584020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH820467A CH523248A (de)	1966-06-10	1967-06-10	Verfahren zur Herstellung neuartiger antiphlogistischer und anticholesterolemischer, in 3-Stellung durch eine aliphatische Gruppe substituierter Indole von niederer Toxizität

Country Status (6)

Country	Link
AT (1)	AT277993B (cs)
CH (1)	CH523248A (cs)
CS (1)	CS167222B2 (cs)
FR (2)	FR6774M (cs)
GB (1)	GB1170620A (cs)
SE (4)	SE334883B (cs)

1967
- 1967-05-29 SE SE08124/68A patent/SE334883B/xx unknown
- 1967-05-29 SE SE7517/67A patent/SE313566B/xx unknown
- 1967-05-29 SE SE08126/68A patent/SE334885B/xx unknown
- 1967-06-09 CS CS4254A patent/CS167222B2/cs unknown
- 1967-06-09 FR FR109823A patent/FR6774M/fr not_active Expired
- 1967-06-10 CH CH820467A patent/CH523248A/de not_active IP Right Cessation
- 1967-06-12 GB GB26965/67A patent/GB1170620A/en not_active Expired
- 1967-06-12 AT AT544167A patent/AT277993B/de not_active IP Right Cessation
- 1967-08-22 FR FR118588A patent/FR1543321A/fr not_active Expired
1968
- 1968-06-14 SE SE812568A patent/SE334884B/xx unknown

Also Published As

Publication number	Publication date
GB1170620A (en)	1969-11-12
SE334883B (cs)	1971-05-10
FR1543321A (fr)	1968-10-25
SE313566B (cs)	1969-08-18
CS167222B2 (cs)	1976-04-29
AT277993B (de)	1970-01-12
FR6774M (cs)	1969-03-10
SE334884B (cs)	1971-05-10
SE334885B (cs)	1971-05-10

Legal Events

Date	Code	Title	Description
1978-01-13	PL	Patent ceased

Publication	Publication Date	Title
DE1795613C3 (de)	1973-10-18	Indolylessigsäuren, Verfahren zu ihrer Herstellung und Arzneimittel. Ausscheidung aus: 1620358
CH633515A5 (de)	1982-12-15	Substituierte phenylessigsaeurederivate und verfahren zu ihrer herstellung.
EP0048911B1 (de)	1984-12-05	O-substituierte alpha-Ketocarbonsäureoxime, Verfahren zu ihrer Herstellung, sowie Arzneimittel, die diese Verbindungen enthalten
DE1620442C3 (de)	1975-07-03	Verfahren zur Herstellung von 1-Acylindolverbindungen
EP0087655B1 (de)	1986-07-16	Verfahren zur Herstellung von Acemetacin
EP0380712B1 (de)	1995-01-04	Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten
EP0072960B1 (de)	1989-06-07	1,5-Diphenylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3102769A1 (de)	1982-02-04	"bis-moranolinderivate"
DE2057840C3 (de)	1980-05-29	Verfahren zur Herstellung von Indolderivaten
DE2056173A1 (de)	1971-05-19	3,5 Diphenyl 4 pyrazolessigsaure. ihre m 1 Stellung substituierten Derivate und Verfahren zur Herstellung dieser Verbin düngen
DE2241027A1 (de)	1973-03-01	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE1949987B2 (de)	1976-11-04	Neue alpha-phenylfettsaeureverbindungen
AT234103B (de)	1964-06-10	Verfahren zur Herstellung von neuen, benzylindolylsubstituierten niedrigen aliphatischen Säuren sowie deren Salzen und Estern
DE2164662A1 (de)	1972-07-27	Indanderivate und Verfahren zu ihrer Herstellung
DE2640884A1 (de)	1977-03-24	Neue entzuendungshemmende l-oxo-isoindolin-derivate und verfahren zu ihrer herstellung
EP0345464B1 (de)	1993-03-17	Verfahren zur Herstellung von substituierten 3-Amino-2(benzoyl)-acrylsäureestern sowie ein Verfahren zur Herstellung von Zwischenprodukten für antibakterielle Wirkstoffe aus diesen Verbindungen
DE1695722C3 (de)	1975-01-16	i-Acyl-3-lndolylcarbonsäurederivate und Verfahren zu ihrer Herstellung
DE1695804A1 (de)	1972-03-02	1-Acryl-3-indolylcarbonsaeureverbindungen und Verfahren zu ihrer Herstellung
DE1695734C (de)	1974-01-31	l-Acyl-3-indoly !carbonsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE1695734A1 (de)	1972-03-02	Verfahren zur Herstellung von 1-Acryl-3-indolylfettsaeurederivaten
DE1795671C3 (de)	1976-03-18	Verfahren zur Herstellung von i-Acyl-3-indolylcarbonsäureverbindungen
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