CH616410A5 - - Google Patents

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Info

Publication number: CH616410A5
Authority: CH; Switzerland
Prior art keywords: indole; phenyl; compound; methyl; linear
Prior art date: 1975-03-21

Application number

CH319876A

Other languages

English (en)

French (fr)

Inventor

Paul De Cointet De Fillain

Souli Nanthavong

Charles Pigerol

Original Assignee

Labaz

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.)

1975-03-21

Filing date

1976-03-15

Publication date

1980-03-31

1976-03-15 Application filed by Labaz filed Critical Labaz

1980-03-31 Publication of CH616410A5 publication Critical patent/CH616410A5/fr

Links

150000001875 compounds Chemical class 0.000 claims description 44
238000000034 method Methods 0.000 claims description 23
239000003381 stabilizer Substances 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
229920000642 polymer Polymers 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 5
229920001577 copolymer Polymers 0.000 claims description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 2
230000017858 demethylation Effects 0.000 claims description 2
238000010520 demethylation reaction Methods 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
238000006243 chemical reaction Methods 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 91
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 44
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 41
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 18
-1 C12 alkyloxy radical Chemical class 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 16
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000000203 mixture Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000000605 extraction Methods 0.000 description 7
239000004800 polyvinyl chloride Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
235000013305 food Nutrition 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
238000004806 packaging method and process Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
230000000087 stabilizing effect Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 6
RAEPNARTKQGOEP-UHFFFAOYSA-N 2-phenyl-1h-indol-5-ol Chemical compound C=1C2=CC(O)=CC=C2NC=1C1=CC=CC=C1 RAEPNARTKQGOEP-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229920000915 polyvinyl chloride Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
WDNQXBINWCYPJI-UHFFFAOYSA-N 5-dodecoxy-2-phenyl-1h-indole Chemical compound C=1C2=CC(OCCCCCCCCCCCC)=CC=C2NC=1C1=CC=CC=C1 WDNQXBINWCYPJI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
KGWPHCDTOLQQEP-UHFFFAOYSA-N 7-methylindole Chemical compound CC1=CC=CC2=C1NC=C2 KGWPHCDTOLQQEP-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000000470 constituent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
231100000053 low toxicity Toxicity 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
OPNPAIWYDKHYFB-UHFFFAOYSA-N 2-phenyl-1h-indol-6-ol Chemical compound N1C2=CC(O)=CC=C2C=C1C1=CC=CC=C1 OPNPAIWYDKHYFB-UHFFFAOYSA-N 0.000 description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 2
JLVHJFKZSFKVHO-UHFFFAOYSA-N 6-methoxy-2-phenyl-1h-indole Chemical compound N1C2=CC(OC)=CC=C2C=C1C1=CC=CC=C1 JLVHJFKZSFKVHO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920001756 Polyvinyl chloride acetate Polymers 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
238000003490 calendering Methods 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125797 compound 12 Drugs 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
230000003750 conditioning effect Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000013508 migration Methods 0.000 description 2
230000005012 migration Effects 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
239000003643 water by type Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
CPHAKIQSOMATHD-UHFFFAOYSA-N 1-(2-chloro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(Cl)=C1 CPHAKIQSOMATHD-UHFFFAOYSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
FUWVMBCPMRAWPG-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-hydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)OCC(O)CO FUWVMBCPMRAWPG-UHFFFAOYSA-N 0.000 description 1
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 1
YPKBCLZFIYBSHK-UHFFFAOYSA-N 5-methylindole Chemical compound CC1=CC=C2NC=CC2=C1 YPKBCLZFIYBSHK-UHFFFAOYSA-N 0.000 description 1
ONYNOPPOVKYGRS-UHFFFAOYSA-N 6-methylindole Natural products CC1=CC=C2C=CNC2=C1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
LIEYAZJYCTUZBM-UHFFFAOYSA-N C(CCCCC)(=O)O.CC[K] Chemical compound C(CCCCC)(=O)O.CC[K] LIEYAZJYCTUZBM-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
150000008062 acetophenones Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000007664 blowing Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007398 colorimetric assay Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920000131 polyvinylidene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
238000001149 thermolysis Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
229920006163 vinyl copolymer Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1

Classifications

- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- 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
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Indole Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)

CH319876A 1975-03-21 1976-03-15 CH616410A5 (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7508871A FR2304606A1 (fr)	1975-03-21	1975-03-21	Nouveaux stabilisants des polymeres et copolymeres du chlorure de vinyle

Publications (1)

Publication Number	Publication Date
CH616410A5 true CH616410A5 (xx)	1980-03-31

Family

ID=9152890

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH319876A CH616410A5 (xx)	1975-03-21	1976-03-15

Country Status (9)

Country	Link
US (1)	US4113736A (xx)
JP (1)	JPS51117743A (xx)
BE (1)	BE839762A (xx)
CH (1)	CH616410A5 (xx)
DE (1)	DE2612057A1 (xx)
FR (1)	FR2304606A1 (xx)
GB (1)	GB1488464A (xx)
NL (1)	NL7602888A (xx)
SE (1)	SE415757B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2407236A1 (fr) *	1977-10-28	1979-05-25	Labaz	Nouvelle association stabilisante pour resines vinyliques
US4543360A (en) *	1981-09-10	1985-09-24	Degussa Aktiengesellschaft	2-(Hydroxy-phenyl)-indoles and process for their production
US5428052A (en) *	1984-09-19	1995-06-27	Centre Internationale De Recherches Dermatologiques (C.I.R.D.)	Aromatic heterocyclic derivatives and their therapeutic and cosmetic use
FR2811324B1 (fr) *	2000-07-04	2003-08-29	Rhodia Chimie Sa	Stabilisation de polymeres halogenes au moyen de pyrroles ou derives et compositions les comprenant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3076814A (en) *	1954-04-28	1963-02-05	Upjohn Co	Novel process for the preparation of tryptophols and to novel compounds produced therein
US3352856A (en) *	1965-12-20	1967-11-14	Upjohn Co	2-(p-alkoxyphenyl)-3-substituted indoles
US4024155A (en) *	1974-06-05	1977-05-17	Labaz	2-(3'-Methoxy-4'-hydroxy-phenol)-indole

1975
- 1975-03-21 FR FR7508871A patent/FR2304606A1/fr active Granted
1976
- 1976-02-25 SE SE7602335A patent/SE415757B/xx unknown
- 1976-03-12 JP JP51027624A patent/JPS51117743A/ja active Pending
- 1976-03-15 CH CH319876A patent/CH616410A5/fr not_active IP Right Cessation
- 1976-03-17 US US05/667,557 patent/US4113736A/en not_active Expired - Lifetime
- 1976-03-19 GB GB11306/76A patent/GB1488464A/en not_active Expired
- 1976-03-19 BE BE165327A patent/BE839762A/xx unknown
- 1976-03-19 NL NL7602888A patent/NL7602888A/xx not_active Application Discontinuation
- 1976-03-22 DE DE19762612057 patent/DE2612057A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
JPS51117743A (en)	1976-10-16
FR2304606B1 (xx)	1978-02-03
DE2612057A1 (de)	1977-02-17
NL7602888A (nl)	1976-09-23
SE415757B (sv)	1980-10-27
FR2304606A1 (fr)	1976-10-15
US4113736A (en)	1978-09-12
SE7602335L (sv)	1976-09-22
BE839762A (fr)	1976-09-20
GB1488464A (en)	1977-10-12

Publication	Publication Date	Title
WO2011107705A1 (fr)	2011-09-09	Derives de cetobenzofurane ainsi que leur procede de synthese et le intermediaires
CH619933A5 (xx)	1980-10-31
CZ290535B6 (cs)	2002-08-14	Způsob výroby beta-diketonů
FR2663935A1 (fr)	1992-01-03	Nouveaux 1,2,3,4,5,6-hexahydroazepino [4,5-b] indoles et 1,2,3,4-tetrahydrobethacarbolines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
EP0011059A1 (fr)	1980-05-14	Procédé de préparation de la (+,-) vincadifformine et d'autres dérivés pentacycliques apparentés
Fieser et al.	1942	Reaction of Grignard reagents with acyloxyanthrones
CH616410A5 (xx)	1980-03-31
DE1961778A1 (de)	1970-06-18	Verfahren zur Herstellung von Brenzcatechin-Derivaten
BE1007245A3 (fr)	1995-05-02	Derives di-substitues des n, n'-ditrimethoxybenzoyle piperazine, un procede pour leur preparation et compositions therapeutiques en contenant.
CA1067085A (fr)	1979-11-27	Stabilisants des polymeres et copolymeres du chlorure de vinyle
FR2493147A1 (fr)	1982-05-07	Compositions pharmaceutiques contenant des pyranones substituees en position 6
Kirby et al.	1956	Some naturally occurring dimethylchromenes. II. Alloevodione
EP0685473B1 (fr)	1997-05-14	Composés benzohétérocycliques, en tant qu'antioxydants
EP0038731B1 (fr)	1983-10-26	Dérivés de thiazole, leur préparation et leur application en thérapeutique
EP0017578A1 (fr)	1980-10-15	Acides 5-(2-hydroxy-3-thiopropoxy)chromone-2-carboxyliques, leurs sels et esters, procédé de préparation et médicaments
EP0025383B1 (fr)	1982-09-22	Nouveaux dérivés substitués du cyclopropène, leur préparation et leur application dans la synthèse de précurseurs de l'acide dl cis chrysanthémique
BE806848A (fr)	1974-04-30	Medicament a base d'un derive de la quinoleine
FR2551751A1 (fr)	1985-03-15	Nouveau procede de preparation d'un derive pyroglutamique, nouveaux derives pyroglutamiques, nouveaux intermediaires de synthese de preparation de ceux-ci et utilisation ou application des derives pyroglutamiques comme agents antibacteriens ou antifongiques
FR2580644A1 (fr)	1986-10-24	Derives de l'acide ascorbique
EP0376824A1 (fr)	1990-07-04	Procédé de préparaton de dérivés du chromanne et intermédiaires de synthèse
EP0017523A1 (fr)	1980-10-15	Nouveaux dérivés du dithiépinno (1,4)(2,3-c)pyrrole, leur préparation et les médicaments qui les contiennent
FR2558833A1 (fr)	1985-08-02	Nouveaux derives de la 4,4-dimethyl tetrahydro-2-pyran-2-one, leur procede de preparation et leur application a la synthese de derives cyclopropaniques
DE918929C (de)	1954-10-07	Verfahren zur Herstellung von Furano-(4', 5':6, 7)-chromonen
CH622778A5 (en)	1981-04-30	2-Phenylindole derivatives
CH617935A5 (en)	1980-06-30	Preparation of new isoindoline derivatives

Legal Events

Date	Code	Title	Description
1981-11-13	PFA	Name/firm changed	Owner name: SANOFI
1981-11-13	PUE	Assignment	Owner name: OMNIUM FINANCIER AQUITAINE POUR L'HYGIENE ET LA SA
1983-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased