NO880910L - Fremgangsmaate ved fremstilling av chromonderivater. - Google Patents
Fremgangsmaate ved fremstilling av chromonderivater.Info
- Publication number
- NO880910L NO880910L NO880910A NO880910A NO880910L NO 880910 L NO880910 L NO 880910L NO 880910 A NO880910 A NO 880910A NO 880910 A NO880910 A NO 880910A NO 880910 L NO880910 L NO 880910L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- benzopyran
- oxo
- compound
- nmr
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 100
- 150000002148 esters Chemical group 0.000 claims description 16
- FGHVMCFOHSEWFZ-UHFFFAOYSA-N 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 FGHVMCFOHSEWFZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000001408 amides Chemical group 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 238000003797 solvolysis reaction Methods 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- FLRTVCQICUEFBG-UHFFFAOYSA-N 2-[2-(cyclopenten-1-yl)-4-oxochromen-8-yl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCC1 FLRTVCQICUEFBG-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000013078 crystal Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- -1 propen-1-yl Chemical group 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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- 238000003756 stirring Methods 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 230000000259 anti-tumor effect Effects 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- OYGWYROFNMWVGW-UHFFFAOYSA-N 2-[2-(1-bromocyclohexyl)-4-oxochromen-8-yl]acetonitrile Chemical compound C=1C(=O)C2=CC=CC(CC#N)=C2OC=1C1(Br)CCCCC1 OYGWYROFNMWVGW-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 150000004777 chromones Chemical class 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- GUGXENROMIJRPN-UHFFFAOYSA-N 1-(2-hydroxy-3-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C)=C1O GUGXENROMIJRPN-UHFFFAOYSA-N 0.000 description 3
- JMNAWLAZQUSQIB-UHFFFAOYSA-N 1-(5-chloro-2-hydroxy-3-methylphenyl)-3-cyclohexylpropane-1,3-dione Chemical compound CC1=CC(Cl)=CC(C(=O)CC(=O)C2CCCCC2)=C1O JMNAWLAZQUSQIB-UHFFFAOYSA-N 0.000 description 3
- IRLGJTFDIGHCHX-UHFFFAOYSA-N 2-(1-bromocyclohexyl)-8-(bromomethyl)chromen-4-one Chemical compound BrCC1=CC=CC(C(C=2)=O)=C1OC=2C1(Br)CCCCC1 IRLGJTFDIGHCHX-UHFFFAOYSA-N 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- USNYPPUKIWBUDE-UHFFFAOYSA-N ethyl 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetate Chemical compound CCOC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 USNYPPUKIWBUDE-UHFFFAOYSA-N 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- ASTWMSSOIXWTNS-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetate Chemical compound O1C(C)(C)OCC1COC(=O)CC1=CC=CC2=C1OC(C=1CCCCC=1)=CC2=O ASTWMSSOIXWTNS-UHFFFAOYSA-N 0.000 description 2
- DTWIBMXVGQEBDH-UHFFFAOYSA-N (2-acetyl-6-methylphenyl) cyclohexanecarboxylate Chemical compound CC(=O)C1=CC=CC(C)=C1OC(=O)C1CCCCC1 DTWIBMXVGQEBDH-UHFFFAOYSA-N 0.000 description 2
- VDHSOXMNRWSQTC-UHFFFAOYSA-N 1-(5-chloro-2-hydroxy-3-methylphenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC(C)=C1O VDHSOXMNRWSQTC-UHFFFAOYSA-N 0.000 description 2
- BPOHUJFSPYRUHT-UHFFFAOYSA-N 1-cyclopentyl-3-(2-hydroxy-3-methylphenyl)propane-1,3-dione Chemical compound CC1=CC=CC(C(=O)CC(=O)C2CCCC2)=C1O BPOHUJFSPYRUHT-UHFFFAOYSA-N 0.000 description 2
- ONUOCMWTNFPKGZ-UHFFFAOYSA-N 2-(1-bromocyclohexyl)-8-(bromomethyl)-6-chlorochromen-4-one Chemical compound C=1C(=O)C2=CC(Cl)=CC(CBr)=C2OC=1C1(Br)CCCCC1 ONUOCMWTNFPKGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FNHYKEHBKGVXGP-UHFFFAOYSA-N 2-[2-(1-bromocyclohexyl)-6-chloro-4-oxochromen-8-yl]acetonitrile Chemical compound C=1C(=O)C2=CC(Cl)=CC(CC#N)=C2OC=1C1(Br)CCCCC1 FNHYKEHBKGVXGP-UHFFFAOYSA-N 0.000 description 2
- QYHIMXCQSZCMIZ-UHFFFAOYSA-N 2-[2-(1-bromocyclopentyl)-4-oxochromen-8-yl]acetonitrile Chemical compound C=1C(=O)C2=CC=CC(CC#N)=C2OC=1C1(Br)CCCC1 QYHIMXCQSZCMIZ-UHFFFAOYSA-N 0.000 description 2
- PJVOOAUWQSVCAT-UHFFFAOYSA-N 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 PJVOOAUWQSVCAT-UHFFFAOYSA-N 0.000 description 2
- XRGHUELPMQIWGR-UHFFFAOYSA-N 2-cyclohexyl-8-methylchromen-4-one Chemical compound CC1=CC=CC(C(C=2)=O)=C1OC=2C1CCCCC1 XRGHUELPMQIWGR-UHFFFAOYSA-N 0.000 description 2
- FJKXFWRVTLCMRB-UHFFFAOYSA-N 2-cyclopentyl-8-methylchromen-4-one Chemical compound CC1=CC=CC(C(C=2)=O)=C1OC=2C1CCCC1 FJKXFWRVTLCMRB-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 238000011740 C57BL/6 mouse Methods 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
- 239000007901 soft capsule Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- ROYRNCFEFJKZJP-UHFFFAOYSA-N (2-acetyl-4-chloro-6-methylphenyl) cyclohexanecarboxylate Chemical compound CC(=O)C1=CC(Cl)=CC(C)=C1OC(=O)C1CCCCC1 ROYRNCFEFJKZJP-UHFFFAOYSA-N 0.000 description 1
- CHZTUHQVJMIILT-UHFFFAOYSA-N 1-(2-hydroxy-3-methylphenyl)-4-propylheptane-1,3-dione Chemical compound CCCC(CCC)C(=O)CC(=O)C1=CC=CC(C)=C1O CHZTUHQVJMIILT-UHFFFAOYSA-N 0.000 description 1
- XHLLQIVDYYVJMD-UHFFFAOYSA-N 1-cycloheptyl-3-(2-hydroxy-3-methylphenyl)propane-1,3-dione Chemical compound CC1=CC=CC(C(=O)CC(=O)C2CCCCCC2)=C1O XHLLQIVDYYVJMD-UHFFFAOYSA-N 0.000 description 1
- QXIYTKDMAIOTLG-UHFFFAOYSA-N 1-cyclohexyl-3-(2-hydroxy-3-methylphenyl)propane-1,3-dione Chemical compound CC1=CC=CC(C(=O)CC(=O)C2CCCCC2)=C1O QXIYTKDMAIOTLG-UHFFFAOYSA-N 0.000 description 1
- OBHSHZJSNQXXEN-UHFFFAOYSA-N 2-(1-bromocycloheptyl)-8-(bromomethyl)chromen-4-one Chemical compound BrCC1=CC=CC(C(C=2)=O)=C1OC=2C1(Br)CCCCCC1 OBHSHZJSNQXXEN-UHFFFAOYSA-N 0.000 description 1
- VLIMOOKTXXLNSD-UHFFFAOYSA-N 2-(1-bromocyclopentyl)-8-(bromomethyl)chromen-4-one Chemical compound BrCC1=CC=CC(C(C=2)=O)=C1OC=2C1(Br)CCCC1 VLIMOOKTXXLNSD-UHFFFAOYSA-N 0.000 description 1
- UUTROXMCRNEGOQ-UHFFFAOYSA-N 2-(2-hept-3-en-4-yl-4-oxochromen-8-yl)acetic acid Chemical compound C1=CC(CC(O)=O)=C2OC(C(=CCC)CCC)=CC(=O)C2=C1 UUTROXMCRNEGOQ-UHFFFAOYSA-N 0.000 description 1
- TZZNWMJZDWYJAZ-UHFFFAOYSA-N 2-(4-oxo-2-phenylchromen-8-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CC=CC=C1 TZZNWMJZDWYJAZ-UHFFFAOYSA-N 0.000 description 1
- NPZMVGXGSLXQKK-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-8-(2-morpholin-4-yl-2-oxoethyl)chromen-4-one Chemical compound C1COCCN1C(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 NPZMVGXGSLXQKK-UHFFFAOYSA-N 0.000 description 1
- PXTOXFDSLXDHHK-UHFFFAOYSA-N 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 PXTOXFDSLXDHHK-UHFFFAOYSA-N 0.000 description 1
- BOKLSBXUEVFCPJ-UHFFFAOYSA-N 2-[6-chloro-2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetic acid Chemical compound OC(=O)CC1=CC(Cl)=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 BOKLSBXUEVFCPJ-UHFFFAOYSA-N 0.000 description 1
- QOKADFGNWYCUMM-UHFFFAOYSA-N 2-cycloheptyl-8-methylchromen-4-one Chemical compound CC1=CC=CC(C(C=2)=O)=C1OC=2C1CCCCCC1 QOKADFGNWYCUMM-UHFFFAOYSA-N 0.000 description 1
- SVLHBXCCJCZHIY-UHFFFAOYSA-N 2-heptan-4-yl-8-methylchromen-4-one Chemical compound C1=CC(C)=C2OC(C(CCC)CCC)=CC(=O)C2=C1 SVLHBXCCJCZHIY-UHFFFAOYSA-N 0.000 description 1
- PITHYUDHKJKJNQ-UHFFFAOYSA-N 2-propylpentanoyl chloride Chemical compound CCCC(C(Cl)=O)CCC PITHYUDHKJKJNQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYWPITMKEJTLLI-UHFFFAOYSA-N 6-chloro-2-cyclohexyl-8-methylchromen-4-one Chemical compound CC1=CC(Cl)=CC(C(C=2)=O)=C1OC=2C1CCCCC1 FYWPITMKEJTLLI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 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
- 229930006000 Sucrose Natural products 0.000 description 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SWMGXDBEGAZFEW-UHFFFAOYSA-N benzyl(trimethyl)azanium;cyanide Chemical compound N#[C-].C[N+](C)(C)CC1=CC=CC=C1 SWMGXDBEGAZFEW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- CIYPNZYEUZQIHN-UHFFFAOYSA-N cycloheptanecarbonyl chloride Chemical compound ClC(=O)C1CCCCCC1 CIYPNZYEUZQIHN-UHFFFAOYSA-N 0.000 description 1
- 125000000323 cyclohepten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
- 125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OLTZJZWJPHYTEJ-UHFFFAOYSA-N methyl 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetate Chemical compound COC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 OLTZJZWJPHYTEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- DJVKJPBYFJZNOE-UHFFFAOYSA-N propan-2-yl 2-[2-(cyclohexen-1-yl)-4-oxochromen-8-yl]acetate Chemical compound CC(C)OC(=O)CC1=CC=CC(C(C=2)=O)=C1OC=2C1=CCCCC1 DJVKJPBYFJZNOE-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 150000003586 thorium compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000003313 weakening effect Effects 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4952387 | 1987-03-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO880910D0 NO880910D0 (no) | 1988-03-01 |
| NO880910L true NO880910L (no) | 1988-09-05 |
Family
ID=12833496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO880910A NO880910L (no) | 1987-03-02 | 1988-03-01 | Fremgangsmaate ved fremstilling av chromonderivater. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4904690A (hu) |
| EP (1) | EP0283761A1 (hu) |
| KR (1) | KR880011139A (hu) |
| CN (1) | CN88101674A (hu) |
| AU (1) | AU610131B2 (hu) |
| DD (1) | DD272648A5 (hu) |
| DK (1) | DK110088A (hu) |
| FI (1) | FI880939A (hu) |
| HU (1) | HU200761B (hu) |
| IL (1) | IL85554A0 (hu) |
| NO (1) | NO880910L (hu) |
| PT (1) | PT86874B (hu) |
| ZA (1) | ZA881440B (hu) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USH1427H (en) * | 1988-04-06 | 1995-04-04 | Briet; Phillipe | Substituted flavonoid compounds, their salts, their manufacture and their use in combination with interleukin-2 |
| US5116954A (en) * | 1988-04-06 | 1992-05-26 | Lipha, Lyonnaise Industrielle Pharmaceutique | Pharmaceutically useful flavonoic compounds containing at least one substituent on the benzopyranone ring moiety |
| IL89840A (en) * | 1988-04-06 | 1996-10-31 | Lipha | Substituted flavonoid compounds and salts thereof their preparation and pharmaceutical composition containing them |
| WO1991004663A1 (en) * | 1989-09-26 | 1991-04-18 | The Regents Of The University Of California | 6-amino-1,2-benzopyrones useful for treatment of viral diseases |
| FR2661410B1 (fr) * | 1990-04-27 | 1994-06-03 | Caignard Daniel | Nouveaux derives heterocycliques: 2-styryl 4h-1-benzopyrane-4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5783599A (en) * | 1993-02-24 | 1998-07-21 | Octamer Inc | Methods of treating cancer and viral infections with 5-iodo-6-amino-and 5-iodo-6-nitroso-1 2-benzopyrones |
| EP1218002A4 (en) | 2000-01-24 | 2004-09-22 | Jozef S Mruk | USE OF FLAVON-8 ACETIC ACID IN VASCULAR AND CARDIOVASCULAR INTERVENTIONS AND ACUTE CORONARY SYNDROME |
| JP4664597B2 (ja) * | 2002-04-17 | 2011-04-06 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| AU2003252025A1 (en) * | 2002-07-17 | 2004-02-02 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| JP2005539062A (ja) * | 2002-09-13 | 2005-12-22 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| US20060241130A1 (en) * | 2003-01-31 | 2006-10-26 | Ehud Keinan | Anti-inflammatory compositions and uses thereof |
| WO2005042697A2 (en) * | 2003-10-06 | 2005-05-12 | Cytokinetics, Inc. | Compounds, compositions and methods |
| AU2009295948B2 (en) | 2008-09-29 | 2013-12-05 | GlaxoSmithKline, LLC | Quinazolinone, quinolone and related analogs as sirtuin modulators |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2516922A1 (fr) * | 1981-11-25 | 1983-05-27 | Lipha | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
| IL89840A (en) * | 1988-04-06 | 1996-10-31 | Lipha | Substituted flavonoid compounds and salts thereof their preparation and pharmaceutical composition containing them |
-
1988
- 1988-02-25 IL IL85554A patent/IL85554A0/xx unknown
- 1988-02-27 EP EP88102960A patent/EP0283761A1/en not_active Withdrawn
- 1988-03-01 PT PT86874A patent/PT86874B/pt not_active IP Right Cessation
- 1988-03-01 FI FI880939A patent/FI880939A/fi not_active Application Discontinuation
- 1988-03-01 DD DD88313285A patent/DD272648A5/de not_active IP Right Cessation
- 1988-03-01 US US07/162,765 patent/US4904690A/en not_active Expired - Fee Related
- 1988-03-01 DK DK110088A patent/DK110088A/da not_active Application Discontinuation
- 1988-03-01 ZA ZA881440A patent/ZA881440B/xx unknown
- 1988-03-01 NO NO880910A patent/NO880910L/no unknown
- 1988-03-02 AU AU12553/88A patent/AU610131B2/en not_active Ceased
- 1988-03-02 HU HU881014A patent/HU200761B/hu not_active IP Right Cessation
- 1988-03-02 KR KR1019880002168A patent/KR880011139A/ko not_active Application Discontinuation
- 1988-03-02 CN CN198888101674A patent/CN88101674A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT86874A (pt) | 1988-04-01 |
| IL85554A0 (en) | 1988-08-31 |
| HU200761B (en) | 1990-08-28 |
| ZA881440B (en) | 1988-08-19 |
| CN88101674A (zh) | 1988-10-05 |
| AU1255388A (en) | 1988-09-01 |
| FI880939A (fi) | 1988-09-03 |
| DK110088A (da) | 1988-09-03 |
| DK110088D0 (da) | 1988-03-01 |
| EP0283761A1 (en) | 1988-09-28 |
| NO880910D0 (no) | 1988-03-01 |
| KR880011139A (ko) | 1988-10-26 |
| HUT49598A (en) | 1989-10-30 |
| US4904690A (en) | 1990-02-27 |
| FI880939A0 (fi) | 1988-03-01 |
| PT86874B (pt) | 1992-05-29 |
| AU610131B2 (en) | 1991-05-16 |
| DD272648A5 (de) | 1989-10-18 |
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