DK141096B - Analogifremgangsmåde til fremstilling af substituerede xanthon-2-carboxylsyrer eller farmaceutisk acceptable, ikke-toxiske estere, amider eller salte deraf. - Google Patents

Analogifremgangsmåde til fremstilling af substituerede xanthon-2-carboxylsyrer eller farmaceutisk acceptable, ikke-toxiske estere, amider eller salte deraf. Download PDF

Info

Publication number: DK141096B
Authority: DK; Denmark
Prior art keywords: carboxylic acid; alkyl; compound; acid; mixture
Prior art date: 1971-07-14

Application number

DK347772A

Other languages

Danish (da)

English (en)

Other versions

DK141096C (de

Inventor

John H Fried

Jurg R Pfister

Ian T Harrison

Original Assignee

Syntex Inc

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.)

1971-07-14

Filing date

1972-07-12

Publication date

1980-01-14

1972-01-12 Priority claimed from US217383A external-priority patent/US3873714A/en

1972-06-05 Priority claimed from US00259853A external-priority patent/US3818042A/en

1972-07-12 Application filed by Syntex Inc filed Critical Syntex Inc

1974-07-11 Priority to DK373274A priority Critical patent/DK134699B/da

1976-07-28 Priority to DK339376A priority patent/DK339376A/da

1980-01-14 Publication of DK141096B publication Critical patent/DK141096B/da

1980-07-14 Application granted granted Critical

1980-07-14 Publication of DK141096C publication Critical patent/DK141096C/da

Links

150000003839 salts Chemical class 0.000 title claims description 9
231100000252 nontoxic Toxicity 0.000 title claims description 5
230000003000 nontoxic effect Effects 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 16
238000000034 method Methods 0.000 title description 15
150000002148 esters Chemical class 0.000 title description 10
150000001408 amides Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 23
-1 phenethyl-substituted amides Chemical class 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 10
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 7
241000700198 Cavia Species 0.000 claims description 6
229940047135 glycate Drugs 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
SZGPJHJDNRNHIP-UHFFFAOYSA-N [Cr].[Na].[Na] Chemical compound [Cr].[Na].[Na] SZGPJHJDNRNHIP-UHFFFAOYSA-N 0.000 claims description 4
229960001340 histamine Drugs 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000002314 glycerols Chemical class 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
230000029058 respiratory gaseous exchange Effects 0.000 claims 2
206010003591 Ataxia Diseases 0.000 claims 1
206010013975 Dyspnoeas Diseases 0.000 claims 1
230000002920 convulsive effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
239000002585 base Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
JNPRWSKMJDGYAN-UHFFFAOYSA-N 9-oxoxanthene-2-carboxylic acid Chemical class C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 JNPRWSKMJDGYAN-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000007858 starting material Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 5
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 5
229940112669 cuprous oxide Drugs 0.000 description 5
239000000284 extract Substances 0.000 description 5
208000024891 symptom Diseases 0.000 description 5
SYMSHCCNDCDLPA-UHFFFAOYSA-N 9h-xanthene-2-carboxylic acid Chemical compound C1=CC=C2CC3=CC(C(=O)O)=CC=C3OC2=C1 SYMSHCCNDCDLPA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
230000000172 allergic effect Effects 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
208000010668 atopic eczema Diseases 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000012430 organic reaction media Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
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 3
241001465754 Metazoa Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
208000030961 allergic reaction Diseases 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
229960004592 isopropanol Drugs 0.000 description 3
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 3
DWYSGMAREQOQEG-UHFFFAOYSA-N methyl 9h-xanthene-2-carboxylate Chemical compound C1=CC=C2CC3=CC(C(=O)OC)=CC=C3OC2=C1 DWYSGMAREQOQEG-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 3
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
LVMOFEBTIXUQDP-UHFFFAOYSA-N 4-(4-acetylphenoxy)benzene-1,3-dicarboxylic acid Chemical compound C(=O)(O)C1=CC(=C(C=C1)OC1=CC=C(C=C1)C(C)=O)C(=O)O LVMOFEBTIXUQDP-UHFFFAOYSA-N 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000036783 anaphylactic response Effects 0.000 description 2
208000003455 anaphylaxis Diseases 0.000 description 2
239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
UYODQUJOZNRODS-UHFFFAOYSA-N dimethyl 4-(2-ethylphenoxy)benzene-1,3-dicarboxylate Chemical compound C(=O)(OC)C1=CC(=C(C=C1)OC1=C(C=CC=C1)CC)C(=O)OC UYODQUJOZNRODS-UHFFFAOYSA-N 0.000 description 2
ADXCABFZLVXCNW-UHFFFAOYSA-N dimethyl 4-bromobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=C(Br)C(C(=O)OC)=C1 ADXCABFZLVXCNW-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229940127557 pharmaceutical product Drugs 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
239000003826 tablet Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
NHXNFHLWXMAHCV-UHFFFAOYSA-N 1,2-dimethyl-4-phenoxybenzene Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=CC=C1 NHXNFHLWXMAHCV-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SENXPIKGBCATSH-UHFFFAOYSA-N 1-acetylxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)C SENXPIKGBCATSH-UHFFFAOYSA-N 0.000 description 1
IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
ZMFQOAXYOBAXOH-UHFFFAOYSA-N 4-phenoxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 ZMFQOAXYOBAXOH-UHFFFAOYSA-N 0.000 description 1
WNKRYYFWYMHTGV-UHFFFAOYSA-N 9-oxoxanthene-1-carboxylic acid Chemical class O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)O WNKRYYFWYMHTGV-UHFFFAOYSA-N 0.000 description 1
238000008941 Albumin Reagent Methods 0.000 description 1
206010027654 Allergic conditions Diseases 0.000 description 1
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 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DK347772A 1971-07-14 1972-07-12 Analogifremgangsmåde til fremstilling af substituerede xanthon-2-carboxylsyrer eller farmaceutisk acceptable, ikke-toxiske estere, amider eller salte deraf. DK141096B (da)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DK373274A DK134699B (da)	1971-07-14	1974-07-11	Analogifremgangsmåde til fremstilling af xanthon-2-carboxylsyreforbindelser.
DK339376A DK339376A (da)	1971-07-14	1976-07-28	Analogifremgangsmade til fremstilling af substituerede xanthon-2-carboxylsyrer eller farmaceutisk acceptable, ikke-toxiske estere, amider eller salte deraf

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US16269671A	1971-07-14	1971-07-14
US16269671		1971-07-14
US217383A US3873714A (en)	1971-07-14	1972-01-12	Xanthone carboxylic acids and derivatives
US21738372		1972-01-12
US25985372		1972-06-05
US00259853A US3818042A (en)	1972-01-12	1972-06-05	Xanthone carboxylic acids and derivatives

Publications (2)

Publication Number	Publication Date
DK141096B true DK141096B (da)	1980-01-14
DK141096C DK141096C (de)	1980-07-14

Family

ID=27388786

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK347772A DK141096B (da)	1971-07-14	1972-07-12	Analogifremgangsmåde til fremstilling af substituerede xanthon-2-carboxylsyrer eller farmaceutisk acceptable, ikke-toxiske estere, amider eller salte deraf.

Country Status (11)

Country	Link
AT (1)	AT326121B (de)
BE (1)	BE786169A (de)
CH (1)	CH580093A5 (de)
DE (1)	DE2234256A1 (de)
DK (1)	DK141096B (de)
ES (6)	ES404786A1 (de)
FR (1)	FR2145654B1 (de)
GB (1)	GB1386436A (de)
IL (1)	IL39890A (de)
NL (1)	NL7209628A (de)
SE (1)	SE388421B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4242267A (en)	1980-02-04	1980-12-30	Roussel Uclaf	Process for preparing 5-alkyl-7-(S-alkyl-sulfonimidoyl)-xanthone-2-carboxylic acids
US4585876A (en) *	1982-11-25	1986-04-29	Ciba-Geigy Corporation	Novel xanthones and thioxanthones

0
- BE BE786169D patent/BE786169A/xx unknown
1972
- 1972-07-12 GB GB3253372A patent/GB1386436A/en not_active Expired
- 1972-07-12 FR FR7225353A patent/FR2145654B1/fr not_active Expired
- 1972-07-12 IL IL3989072A patent/IL39890A/en unknown
- 1972-07-12 NL NL7209628A patent/NL7209628A/xx unknown
- 1972-07-12 ES ES404786A patent/ES404786A1/es not_active Expired
- 1972-07-12 DE DE19722234256 patent/DE2234256A1/de active Pending
- 1972-07-12 DK DK347772A patent/DK141096B/da unknown
- 1972-07-12 SE SE919672A patent/SE388421B/xx unknown
- 1972-07-12 AT AT599372A patent/AT326121B/de not_active IP Right Cessation
- 1972-07-12 CH CH1045672A patent/CH580093A5/xx not_active IP Right Cessation
1975
- 1975-03-15 ES ES435673A patent/ES435673A1/es not_active Expired
- 1975-03-15 ES ES435672A patent/ES435672A1/es not_active Expired
- 1975-03-15 ES ES435671A patent/ES435671A1/es not_active Expired
- 1975-03-15 ES ES435670A patent/ES435670A1/es not_active Expired
- 1975-03-15 ES ES435669A patent/ES435669A1/es not_active Expired

Also Published As

Publication number	Publication date
GB1386436A (en)	1975-03-05
BE786169A (fr)	1973-01-12
IL39890A (en)	1976-02-29
ES435671A1 (es)	1977-05-01
CH580093A5 (de)	1976-09-30
AU4445672A (en)	1974-01-17
FR2145654A1 (de)	1973-02-23
FR2145654B1 (de)	1975-06-20
AT326121B (de)	1975-11-25
ES435673A1 (es)	1977-07-01
DE2234256A1 (de)	1973-01-25
ES404786A1 (es)	1976-01-01
ES435672A1 (es)	1977-05-01
ATA599372A (de)	1975-02-15
ES435669A1 (es)	1977-05-01
NL7209628A (de)	1973-01-16
SE388421B (sv)	1976-10-04
ES435670A1 (es)	1977-05-01
DK141096C (de)	1980-07-14

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