IL44114A - Xanthene derivatives and process for their preparation - Google Patents

Xanthene derivatives and process for their preparation

Info

Publication number: IL44114A
Authority: IL; Israel
Prior art keywords: formula; xanthenyl; compound; group; radical
Prior art date: 1973-02-01

Application number

IL44114A

Other languages

English (en)

Other versions

IL44114A0 (en

Original Assignee

Merck Patent Gmbh

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.)

1973-02-01

Filing date

1974-01-29

Publication date

1977-03-31

1974-01-29 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1974-05-16 Publication of IL44114A0 publication Critical patent/IL44114A0/xx

1977-03-31 Publication of IL44114A publication Critical patent/IL44114A/en

Links

238000000034 method Methods 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title claims description 9
125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
150000003732 xanthenes Chemical class 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 88
PTZNOISFQBASDW-UHFFFAOYSA-N 2-(9h-xanthen-2-yl)propan-1-ol Chemical compound C1=CC=C2CC3=CC(C(CO)C)=CC=C3OC2=C1 PTZNOISFQBASDW-UHFFFAOYSA-N 0.000 claims description 30
229910052783 alkali metal Inorganic materials 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 4
SMPOFIBSPGWSDD-UHFFFAOYSA-N 2-(9h-xanthen-2-yl)propyl acetate Chemical compound C1=CC=C2CC3=CC(C(COC(C)=O)C)=CC=C3OC2=C1 SMPOFIBSPGWSDD-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
-1 2-xanthenyl Chemical group 0.000 abstract description 47
230000001741 anti-phlogistic effect Effects 0.000 abstract description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
239000000243 solution Substances 0.000 description 54
239000000203 mixture Substances 0.000 description 53
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000002253 acid Substances 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
239000002904 solvent Substances 0.000 description 18
150000002148 esters Chemical class 0.000 description 17
238000009835 boiling Methods 0.000 description 14
239000003054 catalyst Substances 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
239000007858 starting material Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 9
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
239000011777 magnesium Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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 7
150000004820 halides Chemical class 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003797 solvolysis reaction Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000011701 zinc Chemical group 0.000 description 6
229910052725 zinc Chemical group 0.000 description 6
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 5
230000001476 alcoholic effect Effects 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000013067 intermediate product Substances 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000003826 tablet Substances 0.000 description 5
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 5
CWDKFUVUMIFANO-UHFFFAOYSA-N 2-(1-hydroxypropan-2-yl)xanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(CO)C)=CC=C3OC2=C1 CWDKFUVUMIFANO-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000011575 calcium Substances 0.000 description 4
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 3
VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
239000004411 aluminium Substances 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical group B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000010949 copper Substances 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
239000008298 dragée Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
150000002902 organometallic compounds Chemical class 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
XXCRRUUDMVPMKA-UHFFFAOYSA-N 2-(9h-xanthen-2-yl)propanoic acid Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=C1 XXCRRUUDMVPMKA-UHFFFAOYSA-N 0.000 description 2
MRRXBIOFCGUXQX-UHFFFAOYSA-N 2-bromo-9h-xanthene Chemical compound C1=CC=C2CC3=CC(Br)=CC=C3OC2=C1 MRRXBIOFCGUXQX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VRBNEIWVCZNVEA-UHFFFAOYSA-N C1=CC=C2CC3=CC([Cd]C4=CC=C5OC6=CC=CC=C6CC5=C4)=CC=C3OC2=C1 Chemical compound C1=CC=C2CC3=CC([Cd]C4=CC=C5OC6=CC=CC=C6CC5=C4)=CC=C3OC2=C1 VRBNEIWVCZNVEA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 2
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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
229910020282 Pb(OH) Inorganic materials 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical group 0.000 description 2
235000010210 aluminium Nutrition 0.000 description 2
229910000091 aluminium hydride Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 2
229910001507 metal halide Inorganic materials 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
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125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000001105 regulatory effect 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
229910052707 ruthenium Inorganic materials 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 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
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
229910000018 strontium carbonate Inorganic materials 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000007970 thio esters Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
JFRMYMMIJXLMBB-UHFFFAOYSA-N xanthydrol Chemical class C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 description 1

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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)

IL44114A 1973-02-01 1974-01-29 Xanthene derivatives and process for their preparation IL44114A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2304763A DE2304763A1 (de)	1973-02-01	1973-02-01	Xanthenderivate

Publications (2)

Publication Number	Publication Date
IL44114A0 IL44114A0 (en)	1974-05-16
IL44114A true IL44114A (en)	1977-03-31

Family

ID=5870528

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL44114A IL44114A (en)	1973-02-01	1974-01-29	Xanthene derivatives and process for their preparation

Country Status (17)

Country	Link
US (1)	US3948949A (de)
JP (1)	JPS49102677A (de)
AT (1)	AT339296B (de)
AU (1)	AU471340B2 (de)
BE (1)	BE810427A (de)
CA (1)	CA1023371A (de)
CH (1)	CH603618A5 (de)
CS (1)	CS176262B2 (de)
DD (1)	DD109382A5 (de)
DE (1)	DE2304763A1 (de)
DK (1)	DK136249C (de)
FR (1)	FR2215959B1 (de)
GB (1)	GB1405869A (de)
HU (1)	HU170466B (de)
IL (1)	IL44114A (de)
NL (1)	NL7401346A (de)
ZA (1)	ZA74247B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4007205A (en) *	1976-03-16	1977-02-08	Warner-Lambert Company	7-Substituted-9-oxoxanthene-2-carboxaldehydes
US4743694A (en) *	1986-04-11	1988-05-10	Mercek & Co., Inc.	Diastereocontrolled synthesis of 2-amino alcohols
EP0360622B1 (de) *	1988-09-22	1999-07-28	Sumitomo Chemical Company Limited	Optisch aktive Benzol-Derivate, Verfahren zu ihrer Herstellung und flüssigkristalline Zusammensetzung, welche solche Derivate als flüssigkristalline Verbindung enthält und Licht-Ausschaltelemente
DE102004017398A1 (de) *	2004-04-05	2005-10-20	Clariant Internat Ltd Muttenz	Fluorierte Xanthene und ihre Verwendung in Flüssigkristallmischungen
DE102004019098A1 (de) *	2004-04-20	2005-11-10	Chemogenix Gmbh	Photolabile Schutzgruppen
US10597515B2 (en)	2016-09-02	2020-03-24	Igm Group B.V.	Polycyclic glyoxylates as photoinitiators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3639612A (en) *	1969-05-16	1972-02-01	Lilly Co Eli	Chalcogen containing heterocyclics as an in vitro anti-viral agent

1973
- 1973-02-01 DE DE2304763A patent/DE2304763A1/de active Pending
1974
- 1974-01-14 ZA ZA740247A patent/ZA74247B/xx unknown
- 1974-01-17 CH CH62674A patent/CH603618A5/xx not_active IP Right Cessation
- 1974-01-21 AU AU64729/74A patent/AU471340B2/en not_active Expired
- 1974-01-28 US US05/436,849 patent/US3948949A/en not_active Expired - Lifetime
- 1974-01-28 AT AT67474A patent/AT339296B/de not_active IP Right Cessation
- 1974-01-29 DK DK46074A patent/DK136249C/da active
- 1974-01-29 IL IL44114A patent/IL44114A/en unknown
- 1974-01-30 DD DD176269A patent/DD109382A5/xx unknown
- 1974-01-30 GB GB432974A patent/GB1405869A/en not_active Expired
- 1974-01-30 FR FR7403033A patent/FR2215959B1/fr not_active Expired
- 1974-01-31 JP JP49013269A patent/JPS49102677A/ja active Pending
- 1974-01-31 BE BE140393A patent/BE810427A/xx unknown
- 1974-01-31 CA CA191,442A patent/CA1023371A/en not_active Expired
- 1974-01-31 NL NL7401346A patent/NL7401346A/xx not_active Application Discontinuation
- 1974-01-31 HU HUME1700A patent/HU170466B/hu unknown
- 1974-02-01 CS CS694A patent/CS176262B2/cs unknown

Also Published As

Publication number	Publication date
CA1023371A (en)	1977-12-27
FR2215959A1 (de)	1974-08-30
AT339296B (de)	1977-10-10
FR2215959B1 (de)	1977-07-01
CH603618A5 (de)	1978-08-31
DK136249B (da)	1977-09-12
AU6472974A (en)	1975-07-24
CS176262B2 (de)	1977-06-30
IL44114A0 (en)	1974-05-16
ATA67474A (de)	1977-02-15
AU471340B2 (en)	1976-04-15
NL7401346A (de)	1974-08-05
JPS49102677A (de)	1974-09-27
DD109382A5 (de)	1974-11-05
DE2304763A1 (de)	1974-08-08
BE810427A (fr)	1974-07-31
ZA74247B (en)	1974-12-24
HU170466B (de)	1977-06-28
US3948949A (en)	1976-04-06
GB1405869A (en)	1975-09-10
DK136249C (da)	1978-02-13

Publication	Publication Date	Title
Boekelheide et al.	1959	Syntheses of pyrrocolines unsubstituted in the five-membered ring1
Finch et al.	1975	Total synthesis of dl-9-deoxyprostaglandin E1
IL44114A (en)	1977-03-31	Xanthene derivatives and process for their preparation
Letsinger et al.	1965	Intramolecular Catalysis in Addition of Carboxyl to Carbon-Carbon Triple Bonds1
IL34897A (en)	1973-08-29	History of tetrahydropyridoxylethane, mixtures containing them and their preparation
IL34881A (en)	1974-07-31	Imidazole propellants that are active against bacteria
Cole et al.	1962	45. A stereoselective total synthesis of œstrone, and related studies
CA1199635A (en)	1986-01-21	Derivatives of benzofuranones
Arya et al.	1961	Chemistry of the natural order cupressales—41: the structure and stereochemistry of communic acid
US3555043A (en)	1971-01-12	Tertiary-amino-lower-alkoxy-9-benzylxanthenes and thioxanthenes
PL103733B1 (pl)	1979-07-31	Sposob wytwarzania nowego kwasu 3-/5-fluoro-1-hydroksy-2-metylo/indanylooctowego
NO136092B (de)	1977-04-12
DE2434658A1 (de)	1975-02-06	3-alkenyldibenzo eckige klammer auf b,d eckige klammer zu pyrane, verfahren zu ihrer herstellung und arzneimittel
US3981887A (en)	1976-09-21	Sulfoxides and sulfones
Walker	1953	Podophyllotoxin Studies. Reductive Methods in the Synthesis of Tetralin Lactones from α-Tetralone Derivatives
JPS6016426B2 (ja)	1985-04-25	新規なベンゾ〔ｃ〕キノリン類
US3704249A (en)	1972-11-28	Synthesis of the biologically active diastereoisomer of (-) zearalanol
CA1099269A (en)	1981-04-14	Process for the production of 9-hydroxydibenzo ¬b, d\| pyrans and intermediates therefor
US3969419A (en)	1976-07-13	3-(2-Halo-4-biphenylyl)-1-butanols and derivatives thereof
IE42406B1 (en)	1980-07-30	Diphenyl ether derivatives and processes for their preparation
US4083852A (en)	1978-04-11	Oxa- and thia-steroids
US3555047A (en)	1971-01-12	3 - lower alkyl or alkoxy - 6 - hydroxy flavans and ester derivatives thereof
Robinson et al.	1960	884. Indoles. Part IV. The reaction between 1, 3-dimethylindole and mesityl oxide
US3819694A (en)	1974-06-25	6-(2-(3-hydroxyalkyl)-3,5-disubstituted-phenyl)hexanoic acids and salts thereof
Bennett et al.	1969	Chemistry of the Podocarpaceae. XIX. Oxidation of some Podocarpa-8, 11, 13-trien-19-oic acid derivatives with lead tetraacetate