CH618683A5 - - Google Patents

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Info

Publication number: CH618683A5
Authority: CH; Switzerland
Prior art keywords: phenyl; indole; compound; formula; compounds
Prior art date: 1974-06-18

Application number

CH668678A

Other languages

English (en)

French (fr)

Inventor

Charles Pigerol

Paul De Cointet De Fillain

Souli Nanthavong

Jacques Le Blay

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.)

1974-06-18

Filing date

1978-06-20

Publication date

1980-08-15

1978-06-20 Application filed by Labaz filed Critical Labaz

1980-08-15 Publication of CH618683A5 publication Critical patent/CH618683A5/fr

Links

SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 126
150000001875 compounds Chemical class 0.000 description 125
KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 73
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 60
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 60
239000003381 stabilizer Substances 0.000 description 51
238000012360 testing method Methods 0.000 description 46
238000000034 method Methods 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
-1 alkyl radical Chemical class 0.000 description 23
JNQYGSNJDUQYJB-UHFFFAOYSA-N C(CCCCCCCCCCC)OC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCC)OC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 JNQYGSNJDUQYJB-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
239000000047 product Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
229920000642 polymer Polymers 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 12
239000004800 polyvinyl chloride Substances 0.000 description 12
239000011347 resin Substances 0.000 description 12
229920005989 resin Polymers 0.000 description 12
239000002904 solvent Substances 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 10
229920000915 polyvinyl chloride Polymers 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
229910052736 halogen Inorganic materials 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
239000000470 constituent Substances 0.000 description 8
150000002367 halogens Chemical class 0.000 description 8
230000000087 stabilizing effect Effects 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229940125833 compound 23 Drugs 0.000 description 7
238000000605 extraction Methods 0.000 description 7
235000013305 food Nutrition 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
QWGDBFAEHKZSGA-UHFFFAOYSA-N 2-phenyl-1h-indol-4-ol Chemical compound C=1C=2C(O)=CC=CC=2NC=1C1=CC=CC=C1 QWGDBFAEHKZSGA-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 6
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 description 6
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
229940126208 compound 22 Drugs 0.000 description 6
238000004806 packaging method and process Methods 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
235000012424 soybean oil Nutrition 0.000 description 6
239000003549 soybean oil Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000000859 sublimation Methods 0.000 description 6
230000008022 sublimation Effects 0.000 description 6
VGZGORSVTYLFCS-UHFFFAOYSA-N (2-phenyl-1H-indol-4-yl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 VGZGORSVTYLFCS-UHFFFAOYSA-N 0.000 description 5
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 5
ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 5
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 5
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 5
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000007664 blowing Methods 0.000 description 5
229940125797 compound 12 Drugs 0.000 description 5
229940125810 compound 20 Drugs 0.000 description 5
229940125846 compound 25 Drugs 0.000 description 5
229920001577 copolymer Polymers 0.000 description 5
238000001125 extrusion Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
125000003396 thiol group Chemical group [H]S* 0.000 description 5
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 4
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 4
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 4
239000004925 Acrylic resin Substances 0.000 description 4
229920000178 Acrylic resin Polymers 0.000 description 4
DZNFFYRMGXXQFI-UHFFFAOYSA-N C(=O)(O)COC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 Chemical compound C(=O)(O)COC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 DZNFFYRMGXXQFI-UHFFFAOYSA-N 0.000 description 4
WPQUVBSVRVWPHU-UHFFFAOYSA-N C(C)(=O)OC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 Chemical compound C(C)(=O)OC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 WPQUVBSVRVWPHU-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003910 behenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
235000013539 calcium stearate Nutrition 0.000 description 4
239000008116 calcium stearate Substances 0.000 description 4
239000003086 colorant Substances 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
229940126543 compound 14 Drugs 0.000 description 4
229940126214 compound 3 Drugs 0.000 description 4
229940125898 compound 5 Drugs 0.000 description 4
238000004455 differential thermal analysis Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000007429 general method Methods 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000002411 thermogravimetry Methods 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
CWJVVYLURLZFDN-UHFFFAOYSA-N 2,3-di(octacosanoyloxy)propyl octacosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCC CWJVVYLURLZFDN-UHFFFAOYSA-N 0.000 description 3
CUNPFWJYDIERFL-UHFFFAOYSA-N 2,4-diphenyl-1h-indole Chemical compound C=12C=C(C=3C=CC=CC=3)NC2=CC=CC=1C1=CC=CC=C1 CUNPFWJYDIERFL-UHFFFAOYSA-N 0.000 description 3
WKZRPPBUMLPCRF-UHFFFAOYSA-N 2-(1h-indol-2-yl)phenol Chemical class OC1=CC=CC=C1C1=CC2=CC=CC=C2N1 WKZRPPBUMLPCRF-UHFFFAOYSA-N 0.000 description 3
LDPRSTALQSYFJB-UHFFFAOYSA-N 2-phenyl-1h-indol-4-amine Chemical compound C=1C=2C(N)=CC=CC=2NC=1C1=CC=CC=C1 LDPRSTALQSYFJB-UHFFFAOYSA-N 0.000 description 3
QENFMLJOCSQJLH-UHFFFAOYSA-N 2-phenylindol-2-amine Chemical compound C1=C2C=CC=CC2=NC1(N)C1=CC=CC=C1 QENFMLJOCSQJLH-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
PVJOGMTYQPKSDX-UHFFFAOYSA-N CCCCSC1=C(C=C(C2=CC=CC=C2)N2)C2=CC=C1 Chemical compound CCCCSC1=C(C=C(C2=CC=CC=C2)N2)C2=CC=C1 PVJOGMTYQPKSDX-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
BXFBGHMPNDOCHA-UHFFFAOYSA-N SC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 Chemical compound SC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 BXFBGHMPNDOCHA-UHFFFAOYSA-N 0.000 description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
231100000053 low toxicity Toxicity 0.000 description 3
238000005259 measurement Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
230000003068 static effect Effects 0.000 description 3
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 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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 2
IAKRGXQCKYFJCB-UHFFFAOYSA-N 2-(1h-indol-2-yl)aniline Chemical class NC1=CC=CC=C1C1=CC2=CC=CC=C2N1 IAKRGXQCKYFJCB-UHFFFAOYSA-N 0.000 description 2
IFQFHKMOAIYTMC-UHFFFAOYSA-N 2-benzyl-2-phenyloxirane Chemical compound C1OC1(C=1C=CC=CC=1)CC1=CC=CC=C1 IFQFHKMOAIYTMC-UHFFFAOYSA-N 0.000 description 2
VSCZLWVXNLUNPM-UHFFFAOYSA-N 2-phenyl-4-phenylmethoxy-1H-indole Chemical compound C=1C=CC=CC=1COC(C=1C=2)=CC=CC=1NC=2C1=CC=CC=C1 VSCZLWVXNLUNPM-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
229940126657 Compound 17 Drugs 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
229920001756 Polyvinyl chloride acetate Polymers 0.000 description 2
229920001328 Polyvinylidene chloride Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
235000019484 Rapeseed oil Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
206010070863 Toxicity to various agents Diseases 0.000 description 2
150000008062 acetophenones Chemical class 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000003490 calendering Methods 0.000 description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
238000004040 coloring Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940126142 compound 16 Drugs 0.000 description 2
229940126086 compound 21 Drugs 0.000 description 2
229940125961 compound 24 Drugs 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000017858 demethylation Effects 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000002475 indoles Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910002055 micronized silica Inorganic materials 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000005033 polyvinylidene chloride Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BLGUIMKBRCQORR-UHFFFAOYSA-M potassium;hexanoate Chemical compound [K+].CCCCCC([O-])=O BLGUIMKBRCQORR-UHFFFAOYSA-M 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
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 1
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 1
HNLLCWHRCMJZGB-UHFFFAOYSA-N 1-(3-chloro-4-phenylphenyl)ethanone Chemical compound ClC1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 HNLLCWHRCMJZGB-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
XGKAJJZDQGRYJI-UHFFFAOYSA-N 2-phenyl-1h-indol-3-amine Chemical compound N1C2=CC=CC=C2C(N)=C1C1=CC=CC=C1 XGKAJJZDQGRYJI-UHFFFAOYSA-N 0.000 description 1
MUKVHEAFWKTUCA-UHFFFAOYSA-N 2-phenyl-1h-indole-4-carboxylic acid Chemical compound C=1C=2C(C(=O)O)=CC=CC=2NC=1C1=CC=CC=C1 MUKVHEAFWKTUCA-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-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
XKZGPYZIGPGXQJ-UHFFFAOYSA-N CSC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 Chemical compound CSC1=C2C=C(NC2=CC=C1)C1=CC=CC=C1 XKZGPYZIGPGXQJ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
238000005903 acid hydrolysis reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FIASKJZPIYCESA-UHFFFAOYSA-L calcium;octacosanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O FIASKJZPIYCESA-UHFFFAOYSA-L 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007398 colorimetric assay Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 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
230000002045 lasting effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
RWZVFCIPMBYBCY-UHFFFAOYSA-N methyl 2,2-dihydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)(O)C(=O)OC RWZVFCIPMBYBCY-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-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
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012071 phase Substances 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
FHALLNHVVFMRCA-UHFFFAOYSA-N propane-1,2,3-triol 18,18,18-trihydroxyoctadecanoic acid Chemical compound OC(CCCCCCCCCCCCCCCCC(=O)O)(O)O.OCC(O)CO FHALLNHVVFMRCA-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000001757 thermogravimetry curve Methods 0.000 description 1
238000001149 thermolysis Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
239000003643 water by type Substances 0.000 description 1
235000014101 wine Nutrition 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
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
- 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
- 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)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Indole Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH668678A 1974-06-18 1978-06-20 CH618683A5 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7421042A FR2275461A1 (fr)	1974-06-18	1974-06-18	Nouveaux stabilisants des polymeres et copolymeres du chlorure de vinyle

Publications (1)

Publication Number	Publication Date
CH618683A5 true CH618683A5 (ru)	1980-08-15

Family

ID=9140177

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH793375A CH619933A5 (ru)	1974-06-18	1975-06-18
CH668678A CH618683A5 (ru)	1974-06-18	1978-06-20

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH793375A CH619933A5 (ru)	1974-06-18	1975-06-18

Country Status (21)

Country	Link
US (1)	US4057530A (ru)
JP (1)	JPS5116659A (ru)
AT (1)	AT342040B (ru)
BE (1)	BE830310A (ru)
BG (2)	BG31949A3 (ru)
CA (1)	CA1044242A (ru)
CH (2)	CH619933A5 (ru)
CS (1)	CS216151B2 (ru)
DE (1)	DE2526317A1 (ru)
DK (1)	DK144655C (ru)
ES (1)	ES438684A1 (ru)
FR (1)	FR2275461A1 (ru)
GB (1)	GB1487659A (ru)
HU (1)	HU172039B (ru)
IT (1)	IT1039021B (ru)
NL (1)	NL7507135A (ru)
NO (1)	NO145507C (ru)
PL (1)	PL97670B1 (ru)
RO (2)	RO71963A (ru)
SE (1)	SE408707B (ru)
SU (2)	SU614748A3 (ru)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2844130A1 (de) *	1977-10-14	1979-04-26	Labaz	Neue dihydropyridine und deren verwendung
FR2405937A1 (fr) *	1977-10-14	1979-05-11	Labaz	Nouveaux derives de dihydropyridine, leur procede de preparation et leur application
US4543360A (en) *	1981-09-10	1985-09-24	Degussa Aktiengesellschaft	2-(Hydroxy-phenyl)-indoles and process for their production
DE3204334A1 (de) *	1982-02-09	1983-08-11	Bayer Ag, 5090 Leverkusen	Witterungsstabile polyamide
US5166170A (en) *	1989-07-03	1992-11-24	Hoechst-Roussel Pharmaceuticals Incorporated	2-(aminoaryl) indoles and indolines as topical antiinflammatory agents for the treatment of skin disorders
DE4037004A1 (de) *	1990-11-21	1992-05-27	Bayer Ag	Verfahren zur herstellung von indolen
JP2503851B2 (ja) *	1992-12-24	1996-06-05	タイガー魔法瓶株式会社	電気オ―ブン
US20050282814A1 (en) *	2002-10-03	2005-12-22	Targegen, Inc.	Vasculostatic agents and methods of use thereof
KR20120032574A (ko) *	2002-10-03	2012-04-05	탈자진 인코포레이티드	혈관항상성 유지제 및 그의 사용 방법
KR20060036091A (ko) *	2003-07-15	2006-04-27	스미스클라인 비참 코포레이션	신규 화합물
RU2006139258A (ru)	2004-04-08	2008-05-20	Таргеджен, Инк. (US)	Бензотриазиновые ингибиторы киназ
US7868037B2 (en)	2004-07-14	2011-01-11	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
US7781478B2 (en) *	2004-07-14	2010-08-24	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
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1974
- 1974-06-18 FR FR7421042A patent/FR2275461A1/fr active Granted
1975
- 1975-05-23 GB GB22747/75A patent/GB1487659A/en not_active Expired
- 1975-06-02 US US05/582,915 patent/US4057530A/en not_active Expired - Lifetime
- 1975-06-10 HU HU74LA00000868A patent/HU172039B/hu unknown
- 1975-06-10 DK DK260475A patent/DK144655C/da active
- 1975-06-10 RO RO7591560A patent/RO71963A/ro unknown
- 1975-06-10 RO RO7582484A patent/RO72873A/ro unknown
- 1975-06-12 DE DE19752526317 patent/DE2526317A1/de not_active Ceased
- 1975-06-12 CS CS754143A patent/CS216151B2/cs unknown
- 1975-06-16 BG BG030281A patent/BG31949A3/xx unknown
- 1975-06-16 BG BG036516A patent/BG28074A4/xx unknown
- 1975-06-16 PL PL1975181263A patent/PL97670B1/pl unknown
- 1975-06-16 NL NL7507135A patent/NL7507135A/xx not_active Application Discontinuation
- 1975-06-17 IT IT24413/75A patent/IT1039021B/it active
- 1975-06-17 NO NO752155A patent/NO145507C/no unknown
- 1975-06-17 CA CA229,563A patent/CA1044242A/en not_active Expired
- 1975-06-17 SU SU752147425A patent/SU614748A3/ru active
- 1975-06-17 BE BE157387A patent/BE830310A/xx unknown
- 1975-06-17 SE SE7506951A patent/SE408707B/xx unknown
- 1975-06-18 ES ES438684A patent/ES438684A1/es not_active Expired
- 1975-06-18 AT AT467775A patent/AT342040B/de not_active IP Right Cessation
- 1975-06-18 CH CH793375A patent/CH619933A5/fr not_active IP Right Cessation
- 1975-06-18 JP JP50074965A patent/JPS5116659A/ja active Pending
1976
- 1976-04-15 SU SU762343007A patent/SU621315A3/ru active
1978
- 1978-06-20 CH CH668678A patent/CH618683A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
SE7506951L (sv)	1975-12-19
DK260475A (da)	1975-12-19
BG31949A3 (en)	1982-04-15
GB1487659A (en)	1977-10-05
US4057530A (en)	1977-11-08
ATA467775A (de)	1977-07-15
NO752155L (ru)	1975-12-19
DE2526317A1 (de)	1976-01-08
FR2275461A1 (fr)	1976-01-16
PL97670B1 (pl)	1978-03-30
NO145507B (no)	1981-12-28
CH619933A5 (ru)	1980-10-31
HU172039B (hu)	1978-05-28
SU614748A3 (ru)	1978-07-05
RO71963A (ro)	1982-10-26
NO145507C (no)	1982-04-07
DK144655B (da)	1982-05-03
RO72873A (ro)	1982-04-12
BE830310A (fr)	1975-12-17
CA1044242A (en)	1978-12-12
NL7507135A (nl)	1975-12-22
JPS5116659A (en)	1976-02-10
SU621315A3 (ru)	1978-08-25
FR2275461B1 (ru)	1979-02-09
SE408707B (sv)	1979-07-02
ES438684A1 (es)	1977-03-01
CS216151B2 (en)	1982-10-29
AT342040B (de)	1978-03-10
BG28074A4 (en)	1980-02-25
IT1039021B (it)	1979-12-10
DK144655C (da)	1982-10-11

Publication	Publication Date	Title
CH618683A5 (ru)	1980-08-15
CH617919A5 (en)	1980-06-30	Process for the preparation of new derivatives of esters of phenyl-acetic acid
FR2961205A1 (fr)	2011-12-16	Procede de preparation de composes esteramides
EP0929603B1 (fr)	2003-12-03	Compositions de polymeres plastifies
JPH05310640A (ja)	1993-11-22	ヒドロキシフェニルカルボキシレートの製造方法
CA1067085A (fr)	1979-11-27	Stabilisants des polymeres et copolymeres du chlorure de vinyle
JPH0379364B2 (ru)	1991-12-18
US2437389A (en)	1948-03-09	Oxazoeidones and erocesstok
CH616410A5 (ru)	1980-03-31
DE1545885A1 (de)	1969-12-04	Verfahren zur Herstellung von neuen,kondensierten heterocyclischen Verbindungen
DE2526230A1 (de)	1976-12-16	Neue benzoxazol-derivate, verfahren zu ihrer herstellung und ihre anwendung als optische aufheller
CH633775A5 (fr)	1982-12-31	N-(2-methyl-1-naphtyl)maleimide, utile comme biocide, et son procede de preparation.
FR2687667A1 (fr)	1993-08-27	Esters d'acides carboxyliques d'hydroxyphenylalcanols comme stabilisants.
LU83145A1 (fr)	1981-09-11	Compositions de polyolefines stabilisees contre les radiations ultraviolettes par des derives de la pyrrolidine,stabilisants et procede de stabilisation utilises
US2623897A (en)	1952-12-30	Process for the preparation of gallic acid esters of alcohols having at least 7 carbon atoms
EP0348317A1 (fr)	1989-12-27	Nouveaux polyphosphites et leur utilisation comme stabilisants des polymères halogénés
DE60313124T2 (de)	2007-08-23	Verfahren zur herstellung einer 1,2,3-triazolverbindung
FR2961206A1 (fr)	2011-12-16	Procede de preparation de composes esteramides
Kohler et al.	1926	ISOXAZOLINE OXIDES V. CARBOXYL DERIVATIVES
KR910009415B1 (ko)	1991-11-15	비스(펜옥시)아세틸 nn-디메틸 아미드의 제조방법
Warren et al.	1962	The synthesis and antibacterial activity of analogs of citrinin and dihydrocitrinin
BE817388R (fr)	1975-01-08	Stabilisation de matieres organiques au moyen de derives du pyrazole
Clarke et al.	1911	THE FORMATION OF BENZALDEHYDE AND 2, 4, 6-TRIBROMOANILINE FROM 3, 5-DIBROMO-4-AMINOBENZHYDROL BY THE ACTION OF BROMINE.
Vanderhaeghe	1960	Phenoxazines. I. Ring-Substituted Derivatives
Stanley	1931	STEREOCHEMISTRY OF DIPHENYL COMPOUNDS. THE RESOLUTION OF 8, 8′-DICARBOXY-1, 1′-DINAPHTHYL

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
1984-02-29	PL	Patent ceased
2024-10-31	PL	Patent ceased