CA1242448A - Fabrication de benzophenones nouveau genre - Google Patents

Fabrication de benzophenones nouveau genre

Info

Publication number: CA1242448A
Authority: CA; Canada
Prior art keywords: carboxylic acid; hydroxybenzocyclobutene; formula; salt; group
Prior art date: 1984-06-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000455777A

Other languages

English (en)

Inventor

Georges Haas

Andreas Von Sprecher

Pier G. Ferrini

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1984-06-04

Filing date

1984-06-04

Publication date

1988-09-27

1984-06-04 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1984-06-04 Priority to CA000455777A priority Critical patent/CA1242448A/fr

1988-09-27 Application granted granted Critical

1988-09-27 Publication of CA1242448A publication Critical patent/CA1242448A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 72
230000008569 process Effects 0.000 title claims abstract description 59
238000004519 manufacturing process Methods 0.000 title claims abstract description 26
239000012965 benzophenone Substances 0.000 title claims abstract description 7
150000008366 benzophenones Chemical class 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 207
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 75
239000000203 mixture Substances 0.000 claims abstract description 44
239000001257 hydrogen Substances 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
238000010306 acid treatment Methods 0.000 claims abstract description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
-1 carboxy, carboxy Chemical group 0.000 claims description 158
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 148
150000003839 salts Chemical class 0.000 claims description 140
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 85
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 58
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 38
239000002904 solvent Substances 0.000 claims description 34
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 33
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
238000010438 heat treatment Methods 0.000 claims description 15
125000004423 acyloxy group Chemical group 0.000 claims description 14
NLYMATAMJXFUPF-UHFFFAOYSA-N methyl 4-methoxybicyclo[4.2.0]octa-1(6),2,4,7-tetraene-7-carboxylate Chemical compound C1=C(OC)C=C2C(C(=O)OC)=CC2=C1 NLYMATAMJXFUPF-UHFFFAOYSA-N 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 13
238000003797 solvolysis reaction Methods 0.000 claims description 12
239000000725 suspension Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
230000003647 oxidation Effects 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
RFTGTPDELXQFKQ-UHFFFAOYSA-N 3-benzoyl-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC=C1 RFTGTPDELXQFKQ-UHFFFAOYSA-N 0.000 claims description 7
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
LFHYQTPJWIGZBQ-UHFFFAOYSA-N methyl 3-(2-fluorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1F LFHYQTPJWIGZBQ-UHFFFAOYSA-N 0.000 claims description 6
WBTXDROLEVBESJ-UHFFFAOYSA-N 3-(2,6-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxamide Chemical compound OC=1C=C2C(C(=O)N)=CC2=CC=1C(=O)C1=C(Cl)C=CC=C1Cl WBTXDROLEVBESJ-UHFFFAOYSA-N 0.000 claims description 5
YCUSSPORSYISFP-UHFFFAOYSA-N methyl 3-(2-bromobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1Br YCUSSPORSYISFP-UHFFFAOYSA-N 0.000 claims description 5
QSJVNBYIOCGHPD-UHFFFAOYSA-N methyl 3-benzoyl-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1 QSJVNBYIOCGHPD-UHFFFAOYSA-N 0.000 claims description 5
RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 claims description 4
CJGCTGSBRIEGJV-UHFFFAOYSA-N 3-(2-fluorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC=C1F CJGCTGSBRIEGJV-UHFFFAOYSA-N 0.000 claims description 4
LYKNJWQOGHMIJD-UHFFFAOYSA-N 3-(2,6-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=C(Cl)C=CC=C1Cl LYKNJWQOGHMIJD-UHFFFAOYSA-N 0.000 claims description 3
XAPMZZMNIJRBLK-UHFFFAOYSA-N methyl 3-(2-chlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1Cl XAPMZZMNIJRBLK-UHFFFAOYSA-N 0.000 claims description 3
LNUZGRSIJSJSJU-UHFFFAOYSA-N methyl 3-(3-chlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC(Cl)=C1 LNUZGRSIJSJSJU-UHFFFAOYSA-N 0.000 claims description 3
DUYBYJREWVWPPX-UHFFFAOYSA-N methyl 4-hydroxy-3-(2-methylbenzenecarbothioyl)bicyclo[4.2.0]octa-1(8),2,4,6-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=S)C1=CC=CC=C1C DUYBYJREWVWPPX-UHFFFAOYSA-N 0.000 claims description 3
LYGDSNMRBNESJM-UHFFFAOYSA-N 3-(2,4-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(Cl)C=C1Cl LYGDSNMRBNESJM-UHFFFAOYSA-N 0.000 claims description 2
MOVHXZZIXCFKSW-UHFFFAOYSA-N 3-(2,6-dimethoxybenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound COC1=CC=CC(OC)=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 MOVHXZZIXCFKSW-UHFFFAOYSA-N 0.000 claims description 2
HFIRBPMNILDQCO-UHFFFAOYSA-N 3-(2,6-dimethylbenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound CC1=CC=CC(C)=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 HFIRBPMNILDQCO-UHFFFAOYSA-N 0.000 claims description 2
PKBLCIJSWTVMAV-UHFFFAOYSA-N 3-(2-acetyloxybenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound CC(=O)OC1=CC=CC=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 PKBLCIJSWTVMAV-UHFFFAOYSA-N 0.000 claims description 2
JXLQZEFBKDJVHM-UHFFFAOYSA-N 3-(2-bromobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC=C1Br JXLQZEFBKDJVHM-UHFFFAOYSA-N 0.000 claims description 2
WZIYGCNLGPZYMF-UHFFFAOYSA-N 3-(3,4-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(Cl)C(Cl)=C1 WZIYGCNLGPZYMF-UHFFFAOYSA-N 0.000 claims description 2
LOCOEUICWADHGA-UHFFFAOYSA-N 3-(3-chlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC(Cl)=C1 LOCOEUICWADHGA-UHFFFAOYSA-N 0.000 claims description 2
KNXWHBNIMWQCCL-UHFFFAOYSA-N 3-(4-cyanobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(C#N)C=C1 KNXWHBNIMWQCCL-UHFFFAOYSA-N 0.000 claims description 2
GEUNRUSKMAECCE-UHFFFAOYSA-N 4-hydroxy-3-(2-methoxybenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound COC1=CC=CC=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 GEUNRUSKMAECCE-UHFFFAOYSA-N 0.000 claims description 2
NXWBPCCTMRVABQ-UHFFFAOYSA-N 4-hydroxy-3-(2-methylbenzenecarbothioyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 NXWBPCCTMRVABQ-UHFFFAOYSA-N 0.000 claims description 2
YMXXMSGFXGHXST-UHFFFAOYSA-N 4-hydroxy-3-(2-methylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 YMXXMSGFXGHXST-UHFFFAOYSA-N 0.000 claims description 2
AWTDHYPQRGXFMD-UHFFFAOYSA-N 4-hydroxy-3-(3-methylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound CC1=CC=CC(C(=O)C=2C(=CC=3C(C(O)=O)=CC=3C=2)O)=C1 AWTDHYPQRGXFMD-UHFFFAOYSA-N 0.000 claims description 2
RYAKHRNPFRWNSC-UHFFFAOYSA-N 4-hydroxy-3-(4-methoxybenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 RYAKHRNPFRWNSC-UHFFFAOYSA-N 0.000 claims description 2
FOKCQEXKDOJUCD-UHFFFAOYSA-N 4-hydroxy-3-(4-methylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(C(=C1)O)=CC2=C1C(C(O)=O)=C2 FOKCQEXKDOJUCD-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
OYZUNPHYXFXLGN-UHFFFAOYSA-N methyl 3-(2,4-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=C(Cl)C=C1Cl OYZUNPHYXFXLGN-UHFFFAOYSA-N 0.000 claims description 2
UTNNLYJZDJJWMJ-UHFFFAOYSA-N methyl 3-(2,6-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=C(Cl)C=CC=C1Cl UTNNLYJZDJJWMJ-UHFFFAOYSA-N 0.000 claims description 2
IQQBLIFQURHUDQ-UHFFFAOYSA-N methyl 3-(2,6-dimethylbenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=C(C)C=CC=C1C IQQBLIFQURHUDQ-UHFFFAOYSA-N 0.000 claims description 2
FQNUFKAEJQKGFS-UHFFFAOYSA-N methyl 3-(3,4-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=C(Cl)C(Cl)=C1 FQNUFKAEJQKGFS-UHFFFAOYSA-N 0.000 claims description 2
KRQQNATVMKUIID-UHFFFAOYSA-N methyl 4-hydroxy-3-(2-methoxybenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1OC KRQQNATVMKUIID-UHFFFAOYSA-N 0.000 claims description 2
KNLLHOIKMIBEEN-UHFFFAOYSA-N methyl 4-hydroxy-3-(2-methylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1C KNLLHOIKMIBEEN-UHFFFAOYSA-N 0.000 claims description 2
KCXMMUPWELNYHL-UHFFFAOYSA-N methyl 4-hydroxy-3-(3-methoxycarbonylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC(C(=O)OC)=C1 KCXMMUPWELNYHL-UHFFFAOYSA-N 0.000 claims description 2
XFSJITVGSFDWGZ-UHFFFAOYSA-N methyl 4-hydroxy-3-(3-methylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC(C)=C1 XFSJITVGSFDWGZ-UHFFFAOYSA-N 0.000 claims description 2
AXIAYRZFKREQGY-UHFFFAOYSA-N methyl 4-hydroxy-3-(4-methoxybenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=C(OC)C=C1 AXIAYRZFKREQGY-UHFFFAOYSA-N 0.000 claims description 2
FZKAFCAZLKYYDV-UHFFFAOYSA-N methyl 4-hydroxy-3-[2-(trifluoromethyl)benzoyl]bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1C(F)(F)F FZKAFCAZLKYYDV-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims 9
NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 claims 2
ZHWPJRANBOULBW-UHFFFAOYSA-N 3-(2-chlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC=C1Cl ZHWPJRANBOULBW-UHFFFAOYSA-N 0.000 claims 2
229960000443 hydrochloric acid Drugs 0.000 claims 2
235000011167 hydrochloric acid Nutrition 0.000 claims 2
ILFMXFKEBZZMOH-UHFFFAOYSA-N 3-(4-chlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(Cl)C=C1 ILFMXFKEBZZMOH-UHFFFAOYSA-N 0.000 claims 1
QLOJMSRUABRBBB-UHFFFAOYSA-N 4-hydroxy-3-(3-methylbenzenecarbothioyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound CC1=CC=CC(C(=S)C=2C(=CC=3C(C(O)=O)=CC=3C=2)O)=C1 QLOJMSRUABRBBB-UHFFFAOYSA-N 0.000 claims 1
PBEHJUPFKVYTPF-UHFFFAOYSA-N 4-hydroxy-3-[2-(trifluoromethyl)benzoyl]bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC=C1C(F)(F)F PBEHJUPFKVYTPF-UHFFFAOYSA-N 0.000 claims 1
BMTMJOSWHXZAIQ-UHFFFAOYSA-N 4-hydroxy-3-[3-(trifluoromethyl)benzoyl]bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)=CC2=CC=1C(=O)C1=CC=CC(C(F)(F)F)=C1 BMTMJOSWHXZAIQ-UHFFFAOYSA-N 0.000 claims 1
125000003368 amide group Chemical group 0.000 claims 1
MJRBPUQSNPCDIQ-UHFFFAOYSA-N methyl 3-(2,6-dimethoxybenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=C(OC)C=CC=C1OC MJRBPUQSNPCDIQ-UHFFFAOYSA-N 0.000 claims 1
ZAIJNLBGJHASMT-UHFFFAOYSA-N methyl 3-(2-acetyloxybenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1OC(C)=O ZAIJNLBGJHASMT-UHFFFAOYSA-N 0.000 claims 1
HFYCWDXZMDHQIU-UHFFFAOYSA-N methyl 3-(4-chlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=C(Cl)C=C1 HFYCWDXZMDHQIU-UHFFFAOYSA-N 0.000 claims 1
RNHSKODZWDGLLF-UHFFFAOYSA-N methyl 3-(4-cyanobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=C(C#N)C=C1 RNHSKODZWDGLLF-UHFFFAOYSA-N 0.000 claims 1
PERFDCXPAYYYQF-UHFFFAOYSA-N methyl 4-hydroxy-3-(3-methylbenzenecarbothioyl)bicyclo[4.2.0]octa-1(8),2,4,6-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=S)C1=CC=CC(C)=C1 PERFDCXPAYYYQF-UHFFFAOYSA-N 0.000 claims 1
MNSABWHTEKQFEQ-UHFFFAOYSA-N methyl 4-hydroxy-3-(4-methylbenzoyl)bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=C(C)C=C1 MNSABWHTEKQFEQ-UHFFFAOYSA-N 0.000 claims 1
VOLSCANUTRZADS-UHFFFAOYSA-N methyl 4-hydroxy-3-[3-(trifluoromethyl)benzoyl]bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound OC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC(C(F)(F)F)=C1 VOLSCANUTRZADS-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 26
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
230000001760 anti-analgesic effect Effects 0.000 abstract 1
239000002253 acid Substances 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
125000004356 hydroxy functional group Chemical group O* 0.000 description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
239000002585 base Substances 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
150000007513 acids Chemical class 0.000 description 33
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 32
239000007858 starting material Substances 0.000 description 31
238000003756 stirring Methods 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
239000003795 chemical substances by application Substances 0.000 description 28
238000001704 evaporation Methods 0.000 description 28
230000008020 evaporation Effects 0.000 description 28
238000002844 melting Methods 0.000 description 27
239000000243 solution Substances 0.000 description 27
230000008018 melting Effects 0.000 description 26
150000003254 radicals Chemical class 0.000 description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
238000006460 hydrolysis reaction Methods 0.000 description 21
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 20
230000007062 hydrolysis Effects 0.000 description 20
239000012074 organic phase Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229910052783 alkali metal Inorganic materials 0.000 description 18
229910052751 metal Inorganic materials 0.000 description 18
239000002184 metal Substances 0.000 description 18
229910052500 inorganic mineral Inorganic materials 0.000 description 17
229910052943 magnesium sulfate Inorganic materials 0.000 description 17
235000019341 magnesium sulphate Nutrition 0.000 description 17
235000010755 mineral Nutrition 0.000 description 17
239000011707 mineral Substances 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
150000001412 amines Chemical class 0.000 description 16
229910021529 ammonia Inorganic materials 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
230000002378 acidificating effect Effects 0.000 description 15
239000003921 oil Substances 0.000 description 15
239000003826 tablet Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
235000011054 acetic acid Nutrition 0.000 description 14
150000001735 carboxylic acids Chemical class 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
239000008346 aqueous phase Substances 0.000 description 13
238000001816 cooling Methods 0.000 description 13
229930195733 hydrocarbon Natural products 0.000 description 13
229920001223 polyethylene glycol Polymers 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 12
235000014113 dietary fatty acids Nutrition 0.000 description 12
239000000194 fatty acid Substances 0.000 description 12
229930195729 fatty acid Natural products 0.000 description 12
239000011734 sodium Substances 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
150000008064 anhydrides Chemical class 0.000 description 11
150000002430 hydrocarbons Chemical class 0.000 description 11
239000011261 inert gas Substances 0.000 description 11
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
125000004043 oxo group Chemical group O=* 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
239000001117 sulphuric acid Substances 0.000 description 11
235000011149 sulphuric acid Nutrition 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
150000001340 alkali metals Chemical class 0.000 description 10
150000002431 hydrogen Chemical group 0.000 description 10
125000001841 imino group Chemical group [H]N=* 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
239000007800 oxidant agent Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
239000000454 talc Substances 0.000 description 10
229910052623 talc Inorganic materials 0.000 description 10
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 9
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
229920002472 Starch Polymers 0.000 description 9
238000009833 condensation Methods 0.000 description 9
230000005494 condensation Effects 0.000 description 9
239000003085 diluting agent Substances 0.000 description 9
239000008101 lactose Substances 0.000 description 9
239000012071 phase Substances 0.000 description 9
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000002202 Polyethylene glycol Substances 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 8
150000008044 alkali metal hydroxides Chemical class 0.000 description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
229910001507 metal halide Inorganic materials 0.000 description 8
150000005309 metal halides Chemical class 0.000 description 8
239000000825 pharmaceutical preparation Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
235000019698 starch Nutrition 0.000 description 8
229910052784 alkaline earth metal Inorganic materials 0.000 description 7
150000003973 alkyl amines Chemical class 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
239000012442 inert solvent Substances 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 6
108010010803 Gelatin Proteins 0.000 description 6
239000002841 Lewis acid Substances 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
238000006136 alcoholysis reaction Methods 0.000 description 6
125000005103 alkyl silyl group Chemical group 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
239000008273 gelatin Substances 0.000 description 6
229920000159 gelatin Polymers 0.000 description 6
229940014259 gelatin Drugs 0.000 description 6
235000019322 gelatine Nutrition 0.000 description 6
235000011852 gelatine desserts Nutrition 0.000 description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
150000007517 lewis acids Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
239000008107 starch Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 5
239000000654 additive Substances 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000003513 alkali Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
150000002191 fatty alcohols Chemical class 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
150000002561 ketenes Chemical class 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
239000002674 ointment Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
150000004707 phenolate Chemical class 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000600 sorbitol Substances 0.000 description 5
235000010356 sorbitol Nutrition 0.000 description 5
125000004953 trihalomethyl group Chemical group 0.000 description 5
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
229930195725 Mannitol Natural products 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
239000005662 Paraffin oil Substances 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
150000001241 acetals Chemical group 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
125000004849 alkoxymethyl group Chemical group 0.000 description 4
239000004411 aluminium Substances 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
238000007098 aminolysis reaction Methods 0.000 description 4
238000005915 ammonolysis reaction Methods 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
229960000541 cetyl alcohol Drugs 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
229940117975 chromium trioxide Drugs 0.000 description 4
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 4
239000006071 cream Substances 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 4
150000002084 enol ethers Chemical class 0.000 description 4
125000001072 heteroaryl group Chemical group 0.000 description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
150000002463 imidates Chemical class 0.000 description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
239000000594 mannitol Substances 0.000 description 4
235000010355 mannitol Nutrition 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
125000003431 oxalo group Chemical group 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 4
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000004332 silver Substances 0.000 description 4
229910052709 silver Inorganic materials 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
239000008117 stearic acid Substances 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 4
125000000464 thioxo group Chemical group S=* 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000005708 Sodium hypochlorite Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical compound OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
239000008298 dragée Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
150000002736 metal compounds Chemical class 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000002905 orthoesters Chemical class 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000012188 paraffin wax Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
150000003180 prostaglandins Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
239000001993 wax Substances 0.000 description 3
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical group CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
CCYVSQDMEQFEOV-UHFFFAOYSA-N 3-(2,6-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1(8),2,4,6-tetraene-7-carbonyl chloride Chemical compound OC1=CC2=C(C(Cl)=O)C=C2C=C1C(=O)C1=C(Cl)C=CC=C1Cl CCYVSQDMEQFEOV-UHFFFAOYSA-N 0.000 description 2
SADXPADQRLNXRW-UHFFFAOYSA-N 3-(2,6-dichlorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carbonitrile Chemical compound OC1=CC=2C(C#N)=CC=2C=C1C(=O)C1=C(Cl)C=CC=C1Cl SADXPADQRLNXRW-UHFFFAOYSA-N 0.000 description 2
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
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 2
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 2
239000004166 Lanolin Substances 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
208000025747 Rheumatic disease Diseases 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
241000534944 Thia Species 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
XYDQMRVDDPZFMM-UHFFFAOYSA-N [Ag+2] Chemical compound [Ag+2] XYDQMRVDDPZFMM-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
229910000272 alkali metal oxide Inorganic materials 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000005530 alkylenedioxy group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
229910000416 bismuth oxide Inorganic materials 0.000 description 2
JDBJCLFKHBHOBN-UHFFFAOYSA-N bismuth(2+) Chemical class [Bi+2] JDBJCLFKHBHOBN-UHFFFAOYSA-N 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
150000004651 carbonic acid esters Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
UUMMHAPECIIHJR-UHFFFAOYSA-N chromium(4+) Chemical compound [Cr+4] UUMMHAPECIIHJR-UHFFFAOYSA-N 0.000 description 2
150000001869 cobalt compounds Chemical class 0.000 description 2
239000000470 constituent Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 2
125000006371 dihalo methyl group Chemical group 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
238000004945 emulsification Methods 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
ANQVKHGDALCPFZ-UHFFFAOYSA-N ethyl 2-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]acetate Chemical compound C1=C2NC(CC(=O)OCC)=NC2=CC=C1N1CCN(C)CC1 ANQVKHGDALCPFZ-UHFFFAOYSA-N 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000010685 fatty oil Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
239000003906 humectant Substances 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
239000011572 manganese Substances 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
229910000474 mercury oxide Inorganic materials 0.000 description 2
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
KPRPRHRSZPIITL-UHFFFAOYSA-N methyl 3-(2-fluorobenzoyl)-4-methoxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylate Chemical compound COC=1C=C2C(C(=O)OC)=CC2=CC=1C(=O)C1=CC=CC=C1F KPRPRHRSZPIITL-UHFFFAOYSA-N 0.000 description 2
PUUPLAJKLHLZQV-UHFFFAOYSA-N methyl 4-benzoyloxybicyclo[4.2.0]octa-1(6),2,4,7-tetraene-7-carboxylate Chemical compound C1=C2C(C(=O)OC)=CC2=CC=C1OC(=O)C1=CC=CC=C1 PUUPLAJKLHLZQV-UHFFFAOYSA-N 0.000 description 2
ACHJNROXLDVAED-UHFFFAOYSA-N methyl 4-hydroxybicyclo[4.2.0]octa-1(6),2,4,7-tetraene-7-carboxylate Chemical compound C1=C(O)C=C2C(C(=O)OC)=CC2=C1 ACHJNROXLDVAED-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
229960002900 methylcellulose Drugs 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000001477 organic nitrogen group Chemical group 0.000 description 2
150000004967 organic peroxy acids Chemical class 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000002304 perfume Substances 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
229940031826 phenolate Drugs 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 2
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 2
239000001230 potassium iodate Substances 0.000 description 2
235000006666 potassium iodate Nutrition 0.000 description 2
229940093930 potassium iodate Drugs 0.000 description 2
239000004323 potassium nitrate Substances 0.000 description 2
235000010333 potassium nitrate Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
230000000552 rheumatic effect Effects 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
229910001923 silver oxide Inorganic materials 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
238000006884 silylation reaction Methods 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000002511 suppository base Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
229940100445 wheat starch Drugs 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
SDOFMBGMRVAJNF-SLPGGIOYSA-N (2r,3r,4r,5s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-SLPGGIOYSA-N 0.000 description 1
FCNWBOLILAEBPO-UHFFFAOYSA-N (4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methanol Chemical compound COC1=CC=C2C=C(CO)C2=C1 FCNWBOLILAEBPO-UHFFFAOYSA-N 0.000 description 1
PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
SXVRSCIZJBGJGB-UHFFFAOYSA-N 1-chloropropan-2-ylbenzene Chemical compound ClCC(C)C1=CC=CC=C1 SXVRSCIZJBGJGB-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
DMVXVRUUBZGVTC-UHFFFAOYSA-N 2-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=S DMVXVRUUBZGVTC-UHFFFAOYSA-N 0.000 description 1
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
UXGOPSNPVZWHOB-UHFFFAOYSA-N 3-(2-fluorobenzoyl)-4-hydroxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxamide Chemical compound OC=1C=C2C(C(=O)N)=CC2=CC=1C(=O)C1=CC=CC=C1F UXGOPSNPVZWHOB-UHFFFAOYSA-N 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
UWQCJRXDYQRGSS-UHFFFAOYSA-N 3-formyl-4-methoxybicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound C1=C(C=O)C(OC)=CC2=C1C=C2C(O)=O UWQCJRXDYQRGSS-UHFFFAOYSA-N 0.000 description 1
GDECAEYOMYOEDP-UHFFFAOYSA-N 3-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=CC(C(Cl)=S)=C1 GDECAEYOMYOEDP-UHFFFAOYSA-N 0.000 description 1
USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 1
UNCXQCVDOMXCOF-UHFFFAOYSA-N 4-methoxybicyclo[4.2.0]octa-1(8),2,4,6-tetraene-7-carboxylic acid Chemical compound COC1=CC=C2C=C(C(O)=O)C2=C1 UNCXQCVDOMXCOF-UHFFFAOYSA-N 0.000 description 1
ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
101150052147 ALLC gene Proteins 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
WNEZFWYVBVVCNA-UHFFFAOYSA-N C[Si](C)(C)C1([Li])SCCCS1 Chemical compound C[Si](C)(C)C1([Li])SCCCS1 WNEZFWYVBVVCNA-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
241001024304 Mino Species 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
241000700159 Rattus Species 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
FGUZFFWTBWJBIL-XWVZOOPGSA-N [(1r)-1-[(2s,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)O[C@H](CO)[C@H]1OC[C@H](O)[C@H]1O FGUZFFWTBWJBIL-XWVZOOPGSA-N 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
WTFWSGRGVQJQHA-UHFFFAOYSA-N [4-hydroxy-7-(hydroxymethyl)-3-bicyclo[4.2.0]octa-1,3,5,7-tetraenyl]-phenylmethanone Chemical compound OC=1C=C2C(CO)=CC2=CC=1C(=O)C1=CC=CC=C1 WTFWSGRGVQJQHA-UHFFFAOYSA-N 0.000 description 1
AQMHNCQZLQUNJI-UHFFFAOYSA-N [CH2]CCCCCC Chemical compound [CH2]CCCCCC AQMHNCQZLQUNJI-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000008063 acylals Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000003502 anti-nociceptive effect Effects 0.000 description 1
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
AASGLWBTIQEPOB-UHFFFAOYSA-N bicyclo[4.2.0]octa-1,3,5,7-tetraene-7-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC2=C1 AASGLWBTIQEPOB-UHFFFAOYSA-N 0.000 description 1
HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004650 carbonic acid diesters Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-L carboxylato carbonate Chemical compound [O-]C(=O)OC([O-])=O ZFTFAPZRGNKQPU-UHFFFAOYSA-L 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
230000001055 chewing effect Effects 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
230000006324 decarbonylation Effects 0.000 description 1
238000006606 decarbonylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000003438 dodecyl group Chemical group [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])* 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000004997 halocarbonyl group Chemical group 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
238000005286 illumination Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
229910001092 metal group alloy Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000004972 metal peroxides Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical class SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
MWZDDLZEOAULRV-UHFFFAOYSA-N methyl 8-formyl-4-methoxybicyclo[4.2.0]octa-1(6),2,4,7-tetraene-7-carboxylate Chemical compound COC(=O)C1=C(C2=C1C=C(C=C2)OC)C=O MWZDDLZEOAULRV-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
125000002092 orthoester group Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([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 1
239000006072 paste Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
FEMRXDWBWXQOGV-UHFFFAOYSA-N potassium amide Chemical class [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001308 pyruvoyl group Chemical group O=C([*])C(=O)C([H])([H])[H] 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
230000009183 running Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229940100890 silver compound Drugs 0.000 description 1
150000003379 silver compounds Chemical class 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
229940057429 sorbitan isostearate Drugs 0.000 description 1
229950004959 sorbitan oleate Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000455777A 1984-06-04 1984-06-04 Fabrication de benzophenones nouveau genre Expired CA1242448A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000455777A CA1242448A (fr)	1984-06-04	1984-06-04	Fabrication de benzophenones nouveau genre

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000455777A CA1242448A (fr)	1984-06-04	1984-06-04	Fabrication de benzophenones nouveau genre

Publications (1)

Publication Number	Publication Date
CA1242448A true CA1242448A (fr)	1988-09-27

Family

ID=4128017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000455777A Expired CA1242448A (fr)	1984-06-04	1984-06-04	Fabrication de benzophenones nouveau genre

Country Status (1)

Country	Link
CA (1)	CA1242448A (fr)

1984
- 1984-06-04 CA CA000455777A patent/CA1242448A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-09-27	MKEX	Expiry

Publication	Publication Date	Title
JP3499553B2 (ja)	2004-02-23	レチノイド様生物学的活性を有するヘテロアリール置換フェニルエテニル化合物
DE2822848A1 (de)	1978-11-30	Mevalonolacton-derivate und verfahren zu deren herstellung
JPS63264578A (ja)	1988-11-01	レチノイド様活性を有する２置換アセチレン
NZ205559A (en)	1987-08-31	Leukotriene antagonists, pharmaceutical compositions, and intermediates
EP0465802A1 (fr)	1992-01-15	Esters aromatiques sensibles et insensibles à l'oxydation comme inhibiteurs de l'elastase neutrophile humaine
US4548948A (en)	1985-10-22	Anti-inflammatory and analgesic benzothiophene and benzafuran derivatives, compositions, and method of use therefor
US4966907A (en)	1990-10-30	6-substituted 5-hydroxy-2,3-dihydrobenzofurans as inhibitors of leukotriene biosynthesis
US4523030A (en)	1985-06-11	Benzophenones
US4665226A (en)	1987-05-12	Process for preparing 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid
NO742802L (fr)	1975-03-17
US4360688A (en)	1982-11-23	Precursors and synthesis of d1-(methyl)-16,16-(dimethyl)-11-alpha, 15-alpha, beta-dihydroxy-9-oxo-2,13,-trans, trans-prostadienoates
NZ208517A (en)	1987-10-30	Substituted 4-benzoyl-5-hydroxybenzocyclobutenes
US4533747A (en)	1985-08-06	Leukotriene antagonists intermediates
US4730005A (en)	1988-03-08	Leukotriene antagonist
PL168679B1 (en)	1996-03-29	Method of obtaining novel chromates and thiochromates of activity similar to that of retidiones
US4230719A (en)	1980-10-28	Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain
US4179452A (en)	1979-12-18	3α,6α-Dihydroxy-5β-cholestan-24-one derivatives and process for preparing the same
CA2021995A1 (fr)	1991-01-28	Derives de l'acide arylalkenoique comme antagonistes des leukotrienes
Naito et al.	1980	Syntheses of (.+-.)-cinnamodial and (.+-.)-cinnamosmolide.
IE902836A1 (en)	1991-03-27	Substituted dibenzofurans and methods of using same
US4213905A (en)	1980-07-22	Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid salts
US4644079A (en)	1987-02-17	Precursors and synthesis of d1-(methyl)-16,16-(dimethyl)-11-alpha, 15-alpha, beta-dihydroxy-9-oxo-2,13,-trans, trans-prostadienoates
US4927945A (en)	1990-05-22	Process for preparing diphenyl ethers
US4474979A (en)	1984-10-02	Synthesis of d1-(methyl)-16,16-(dimethyl-11-alpha, 15-alpha, beta-dihydroxy-9-oxo-2,13,-trans,trans-prostadienoates
US5258559A (en)	1993-11-02	Process for the preparation of [1R-(1β(R*), 3aα, 4β, 7aβ)] octahydro-1-(5-hydroxy-1,5-dimethylhexyl)-7a-methyl-4H-inden-4-one