FI61866C - Foerfarande foer framstaellning av diuretisk eller saluretisk (1-oxo-2-fenyl- eller -tienyl-2-substituerad-5-indanyloxi)aettiksyra eller dess derivat - Google Patents

Foerfarande foer framstaellning av diuretisk eller saluretisk (1-oxo-2-fenyl- eller -tienyl-2-substituerad-5-indanyloxi)aettiksyra eller dess derivat Download PDF

Info

Publication number: FI61866C
Authority: FI; Finland
Prior art keywords: formula; phenyl; dichloro; methyl; compound
Prior art date: 1973-10-11

Application number

FI2789/74A

Other languages

English (en)

Finnish (fi)

Other versions

FI278974A7 (da

FI61866B (fi

Inventor

Jr Edward Jethro Cragoe

Jr Otto William Woltersdorf

Jr Warren Kenneth Russ

George Gustave Hazen

Earl Martin Chamberlin

Original Assignee

Merck & Co 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.)

1973-10-11

Filing date

1974-09-25

Publication date

1982-10-11

1974-07-30 Priority claimed from US05/492,652 external-priority patent/US3981888A/en

1974-09-25 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1975-04-12 Publication of FI278974A7 publication Critical patent/FI278974A7/fi

1980-02-11 Priority to FI800415A priority Critical patent/FI60388C/fi

1982-06-30 Application granted granted Critical

1982-06-30 Publication of FI61866B publication Critical patent/FI61866B/fi

1982-10-11 Publication of FI61866C publication Critical patent/FI61866C/fi

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 63
238000000034 method Methods 0.000 title claims description 36
150000001875 compounds Chemical class 0.000 claims description 66
-1 methoxy, nitro, amino Chemical group 0.000 claims description 37
238000002360 preparation method Methods 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
239000000047 product Substances 0.000 claims description 17
PRKWVSHZYDOZLP-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 PRKWVSHZYDOZLP-UHFFFAOYSA-N 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
239000002934 diuretic Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
125000005059 halophenyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
230000000894 saliuretic effect Effects 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 6
230000001882 diuretic effect Effects 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 4
239000012467 final product Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
229940030606 diuretics Drugs 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
102100038239 Protein Churchill Human genes 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
238000009472 formulation Methods 0.000 claims 6
239000003086 colorant Substances 0.000 claims 1
238000006114 decarboxylation reaction Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
210000005036 nerve Anatomy 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 108
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 39
239000002904 solvent Substances 0.000 description 39
238000000921 elemental analysis Methods 0.000 description 37
239000000243 solution Substances 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
238000002425 crystallisation Methods 0.000 description 33
230000008025 crystallization Effects 0.000 description 33
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 30
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 28
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 27
238000010992 reflux Methods 0.000 description 27
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
229960000583 acetic acid Drugs 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000012258 stirred mixture Substances 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
239000005457 ice water Substances 0.000 description 19
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 13
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
239000000155 melt Substances 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 description 8
ARIBNFLJQYPMIT-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2-methyl-2-phenyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C)C1=CC=CC=C1 ARIBNFLJQYPMIT-UHFFFAOYSA-N 0.000 description 8
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
238000001816 cooling Methods 0.000 description 7
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 7
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 7
XCQVCKFRFDYRJG-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2-phenyl-2,3-dihydroinden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1C1=CC=CC=C1 XCQVCKFRFDYRJG-UHFFFAOYSA-N 0.000 description 6
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 5
RXGLMGBMIGKLHR-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2-methyl-2,3-dihydroinden-1-one Chemical compound ClC1=C(Cl)C(OC)=CC2=C1C(=O)C(C)C2 RXGLMGBMIGKLHR-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
238000000197 pyrolysis Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
229940116269 uric acid Drugs 0.000 description 5
ZRKQOVXGDIZYDS-UHFFFAOYSA-N 5-hydroxy-2,3-dihydroinden-1-one Chemical compound OC1=CC=C2C(=O)CCC2=C1 ZRKQOVXGDIZYDS-UHFFFAOYSA-N 0.000 description 4
238000005727 Friedel-Crafts reaction Methods 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000005661 deetherification reaction Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
230000001376 precipitating effect Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
DJJABNMSRSWWKQ-UHFFFAOYSA-N 2-(4-bromophenyl)-1-(2,3-dichloro-4-methoxyphenyl)ethanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)CC1=CC=C(Br)C=C1 DJJABNMSRSWWKQ-UHFFFAOYSA-N 0.000 description 3
CYOHLLBVSYWSFD-UHFFFAOYSA-N 2-[(6,7-dichloro-1-oxo-2,2-diphenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound O=C1C=2C(Cl)=C(Cl)C(OCC(=O)O)=CC=2CC1(C=1C=CC=CC=1)C1=CC=CC=C1 CYOHLLBVSYWSFD-UHFFFAOYSA-N 0.000 description 3
NPTDHYOKDFDEJI-UHFFFAOYSA-N 2-[(6,7-dichloro-2-cyclopentyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound O=C1C=2C(Cl)=C(Cl)C(OCC(=O)O)=CC=2CC1(C=1C=CC=CC=1)C1CCCC1 NPTDHYOKDFDEJI-UHFFFAOYSA-N 0.000 description 3
FTHBZOYULCSOCU-UHFFFAOYSA-N 2-[(6,7-dichloro-2-ethyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(CC)C1=CC=CC=C1 FTHBZOYULCSOCU-UHFFFAOYSA-N 0.000 description 3
COZVJBYJTPJKFR-UHFFFAOYSA-N 2-bromo-1-(2,3-dichloro-4-methoxyphenyl)-2-methylpropan-1-one Chemical compound COC1=CC=C(C(=O)C(C)(C)Br)C(Cl)=C1Cl COZVJBYJTPJKFR-UHFFFAOYSA-N 0.000 description 3
HDEJFOUALAMENO-UHFFFAOYSA-N 4-(4,5-dichloro-6-hydroxy-2-methyl-3-oxo-1h-inden-2-yl)benzonitrile Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=C(C#N)C=C1 HDEJFOUALAMENO-UHFFFAOYSA-N 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
DQKQSGSQOZEZGX-UHFFFAOYSA-N 6,7-dichloro-2-(4-fluorophenyl)-5-hydroxy-2-methyl-3h-inden-1-one Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=C(F)C=C1 DQKQSGSQOZEZGX-UHFFFAOYSA-N 0.000 description 3
AXNPYAZYXZDXSE-UHFFFAOYSA-N 6,7-dichloro-2-(4-fluorophenyl)-5-methoxy-2-methyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C)C1=CC=C(F)C=C1 AXNPYAZYXZDXSE-UHFFFAOYSA-N 0.000 description 3
FNFBPEKLXGAWDR-UHFFFAOYSA-N 6,7-dichloro-2-cyclopentyl-5-hydroxy-2-phenyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(O)=CC=2CC1(C=1C=CC=CC=1)C1CCCC1 FNFBPEKLXGAWDR-UHFFFAOYSA-N 0.000 description 3
SOCNDNMQAGMZCC-UHFFFAOYSA-N 6,7-dichloro-2-ethyl-5-hydroxy-2-phenyl-3h-inden-1-one Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(CC)C1=CC=CC=C1 SOCNDNMQAGMZCC-UHFFFAOYSA-N 0.000 description 3
WREDCDVPROYNHH-UHFFFAOYSA-N 6,7-dichloro-2-ethyl-5-methoxy-2-phenyl-3h-inden-1-one Chemical compound C1C2=CC(OC)=C(Cl)C(Cl)=C2C(=O)C1(CC)C1=CC=CC=C1 WREDCDVPROYNHH-UHFFFAOYSA-N 0.000 description 3
MFQTYBMQDIRRMK-UHFFFAOYSA-N 6,7-dichloro-2-methyl-5-phenylmethoxy-2,3-dihydroinden-1-one Chemical compound ClC=1C(Cl)=C2C(=O)C(C)CC2=CC=1OCC1=CC=CC=C1 MFQTYBMQDIRRMK-UHFFFAOYSA-N 0.000 description 3
OHBIJKPDXHABFK-UHFFFAOYSA-N 6,7-dichloro-5-hydroxy-2,2-diphenyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(O)=CC=2CC1(C=1C=CC=CC=1)C1=CC=CC=C1 OHBIJKPDXHABFK-UHFFFAOYSA-N 0.000 description 3
SAFNSSIFZSJJIY-UHFFFAOYSA-N 6,7-dichloro-5-hydroxy-2-methyl-2,3-dihydroinden-1-one Chemical compound OC1=C(Cl)C(Cl)=C2C(=O)C(C)CC2=C1 SAFNSSIFZSJJIY-UHFFFAOYSA-N 0.000 description 3
IVVYMAKIXVXQDQ-UHFFFAOYSA-N 6,7-dichloro-5-hydroxy-2-methyl-2-(4-nitrophenyl)-3h-inden-1-one Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=C([N+]([O-])=O)C=C1 IVVYMAKIXVXQDQ-UHFFFAOYSA-N 0.000 description 3
NMCNUPJNSNJHHZ-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2,2-diphenyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C=1C=CC=CC=1)C1=CC=CC=C1 NMCNUPJNSNJHHZ-UHFFFAOYSA-N 0.000 description 3
RYQLUQGJAAYVFW-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2-methyl-2-(4-nitrophenyl)-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C)C1=CC=C([N+]([O-])=O)C=C1 RYQLUQGJAAYVFW-UHFFFAOYSA-N 0.000 description 3
RKSQSDFCBCQJOA-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2-methyl-2-thiophen-2-yl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C)C1=CC=CS1 RKSQSDFCBCQJOA-UHFFFAOYSA-N 0.000 description 3
201000005569 Gout 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
229930040373 Paraformaldehyde Natural products 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
VRQYDYLUERJKTM-UHFFFAOYSA-N 1-(2,3-dichloro-4-methoxyphenyl)-2-methylpropan-1-one Chemical compound COC1=CC=C(C(=O)C(C)C)C(Cl)=C1Cl VRQYDYLUERJKTM-UHFFFAOYSA-N 0.000 description 2
RHUCGJFEPAJWNX-UHFFFAOYSA-N 1-(2,3-dichloro-4-methoxyphenyl)-2-phenylprop-2-en-1-one Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C(=C)C1=CC=CC=C1 RHUCGJFEPAJWNX-UHFFFAOYSA-N 0.000 description 2
FDXZDHGNCGMXKY-UHFFFAOYSA-N 1-(2,3-dichloro-4-methoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C(Cl)=C1Cl FDXZDHGNCGMXKY-UHFFFAOYSA-N 0.000 description 2
IPBNLJNJBSFZBD-UHFFFAOYSA-N 1-(3,4-dichloro-5-methoxyphenyl)-2-phenylethanone Chemical compound ClC1=C(Cl)C(OC)=CC(C(=O)CC=2C=CC=CC=2)=C1 IPBNLJNJBSFZBD-UHFFFAOYSA-N 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
RBJIGQRZLITQJG-UHFFFAOYSA-N 2-(2,3-dichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(Cl)=C1Cl RBJIGQRZLITQJG-UHFFFAOYSA-N 0.000 description 2
WTZNKHZUHRAZIU-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetonitrile Chemical compound C1C2=CC(OCC#N)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 WTZNKHZUHRAZIU-UHFFFAOYSA-N 0.000 description 2
NIDHHPPZZUQCEL-UHFFFAOYSA-N 2-[[6,7-dichloro-2-(4-chlorophenyl)-2-methyl-1-oxo-3h-inden-5-yl]oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=C(Cl)C=C1 NIDHHPPZZUQCEL-UHFFFAOYSA-N 0.000 description 2
SUOULRRZNVFSJY-UHFFFAOYSA-N 4-(4,5-dichloro-6-methoxy-2-methyl-3-oxo-1h-inden-2-yl)benzonitrile Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C)C1=CC=C(C#N)C=C1 SUOULRRZNVFSJY-UHFFFAOYSA-N 0.000 description 2
OPUWUVFUMAPOGK-UHFFFAOYSA-N 6,7-dichloro-2-(4-chlorophenyl)-5-hydroxy-2-methyl-3h-inden-1-one Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=C(Cl)C=C1 OPUWUVFUMAPOGK-UHFFFAOYSA-N 0.000 description 2
ZKBHMRDIUQMTJC-UHFFFAOYSA-N 6,7-dichloro-2-(4-chlorophenyl)-5-methoxy-2-methyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C)C1=CC=C(Cl)C=C1 ZKBHMRDIUQMTJC-UHFFFAOYSA-N 0.000 description 2
BMHAAPMUIOEMKR-UHFFFAOYSA-N 6,7-dichloro-2-cyclopentyl-5-methoxy-2-phenyl-3h-inden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1(C=1C=CC=CC=1)C1CCCC1 BMHAAPMUIOEMKR-UHFFFAOYSA-N 0.000 description 2
FNKRIDAPUUDBPN-UHFFFAOYSA-N 6,7-dichloro-5-hydroxy-2-methyl-2-phenyl-3h-inden-1-one Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 FNKRIDAPUUDBPN-UHFFFAOYSA-N 0.000 description 2
ODNPOXCNIYZLFR-UHFFFAOYSA-N 6,7-dichloro-5-hydroxy-2-methyl-2-thiophen-2-yl-3h-inden-1-one Chemical compound C1C2=CC(O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CS1 ODNPOXCNIYZLFR-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
201000001431 Hyperuricemia Diseases 0.000 description 2
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
DTZZPSFWFUOGAM-UHFFFAOYSA-N cyclohexyl-(2,3-dichloro-4-methoxyphenyl)methanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C1CCCCC1 DTZZPSFWFUOGAM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
238000002156 mixing Methods 0.000 description 2
VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
OOBFPVBXKRNFRW-UHFFFAOYSA-N tert-butyl 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetate Chemical compound O=C1C=2C(Cl)=C(Cl)C(OCC(=O)OC(C)(C)C)=CC=2CC1(C)C1=CC=CC=C1 OOBFPVBXKRNFRW-UHFFFAOYSA-N 0.000 description 2
230000003424 uricosuric effect Effects 0.000 description 2
PRCCZDFRGZGFQL-UHFFFAOYSA-N (1-bromocyclohexyl)-(2,3-dichloro-4-methoxyphenyl)methanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C1(Br)CCCCC1 PRCCZDFRGZGFQL-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
GMQPXSIUBYYIEO-UHFFFAOYSA-N 1-(2,3-dichloro-4-methoxyphenyl)-2-phenylethanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)CC1=CC=CC=C1 GMQPXSIUBYYIEO-UHFFFAOYSA-N 0.000 description 1
OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
CYXGYDSWPPXXKA-UHFFFAOYSA-N 2,2-dichloro-3h-inden-1-one Chemical compound C1=CC=C2C(=O)C(Cl)(Cl)CC2=C1 CYXGYDSWPPXXKA-UHFFFAOYSA-N 0.000 description 1
UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
UOEQDMMGZPLUEM-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)thiophene Chemical compound C1CC2=CC=CC=C2C1C1=CC=CS1 UOEQDMMGZPLUEM-UHFFFAOYSA-N 0.000 description 1
ULUULEQOBVSPGG-UHFFFAOYSA-N 2-(4-bromophenyl)-1-(2,3-dichloro-4-methoxyphenyl)prop-2-en-1-one Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C(=C)C1=CC=C(Br)C=C1 ULUULEQOBVSPGG-UHFFFAOYSA-N 0.000 description 1
WNMJGSPJQCCLCP-UHFFFAOYSA-N 2-(4-bromophenyl)-6,7-dichloro-5-methoxy-2,3-dihydroinden-1-one Chemical compound O=C1C=2C(Cl)=C(Cl)C(OC)=CC=2CC1C1=CC=C(Br)C=C1 WNMJGSPJQCCLCP-UHFFFAOYSA-N 0.000 description 1
VQVBNWUUKLBHGI-UHFFFAOYSA-N 2-(4-bromophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Br)C=C1 VQVBNWUUKLBHGI-UHFFFAOYSA-N 0.000 description 1
XYWPPIGFTRBUQZ-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2,3-diphenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound C12=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C(C)(C=2C=CC=CC=2)C1C1=CC=CC=C1 XYWPPIGFTRBUQZ-UHFFFAOYSA-N 0.000 description 1
JQIFZOWZSCBOTJ-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]propanedioic acid Chemical compound C1C2=CC(OC(C(O)=O)C(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 JQIFZOWZSCBOTJ-UHFFFAOYSA-N 0.000 description 1
DPESQQIBUVKMFX-UHFFFAOYSA-N 2-[[6,7-dichloro-2-(4-fluorophenyl)-2-methyl-1-oxo-3h-inden-5-yl]oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=C(F)C=C1 DPESQQIBUVKMFX-UHFFFAOYSA-N 0.000 description 1
REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
VXYDXULHYXNWKC-UHFFFAOYSA-N 2-chloro-2-(2-chloro-3-oxo-1,3-diphenylpropyl)cyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(Cl)C(C1(Cl)C(CCCC1)=O)C1=CC=CC=C1 VXYDXULHYXNWKC-UHFFFAOYSA-N 0.000 description 1
VODKOOOHHCAWFR-UHFFFAOYSA-N 2-iodoacetonitrile Chemical compound ICC#N VODKOOOHHCAWFR-UHFFFAOYSA-N 0.000 description 1
BEKNOGMQVKBMQN-UHFFFAOYSA-N 2-methyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(C)CC2=C1 BEKNOGMQVKBMQN-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
FOTITZRWZUAVPH-UHFFFAOYSA-N 2-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC=C1 FOTITZRWZUAVPH-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
PWNFGWMGTHLRFS-UHFFFAOYSA-N 6,7-dichloro-2-(4-methoxyphenyl)-2-methyl-5-phenylmethoxy-3h-inden-1-one Chemical compound C1=CC(OC)=CC=C1C1(C)C(=O)C2=C(Cl)C(Cl)=C(OCC=3C=CC=CC=3)C=C2C1 PWNFGWMGTHLRFS-UHFFFAOYSA-N 0.000 description 1
GLTBGFOWHBFZHT-UHFFFAOYSA-N 6,7-dichloro-2-methyl-5-(2-nitroethoxy)-2-phenyl-3h-inden-1-one Chemical compound C1C2=CC(OCC[N+]([O-])=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 GLTBGFOWHBFZHT-UHFFFAOYSA-N 0.000 description 1
CGOQYYNSRCYWNA-UHFFFAOYSA-N 6,7-dichloro-5-hydroxy-2-methyl-2-phenyl-3H-inden-1-one 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3H-inden-5-yl)oxy]acetonitrile Chemical compound CC1(C(C2=C(C(=C(C=C2C1)O)Cl)Cl)=O)C1=CC=CC=C1.O=C1C(CC2=CC(=C(C(=C12)Cl)Cl)OCC#N)(C1=CC=CC=C1)C CGOQYYNSRCYWNA-UHFFFAOYSA-N 0.000 description 1
LZDKOEFJMQLXLN-UHFFFAOYSA-N 6,7-dichloro-5-methoxy-2-methyl-3-phenyl-2,3-dihydroinden-1-one Chemical compound CC1C(=O)C=2C(Cl)=C(Cl)C(OC)=CC=2C1C1=CC=CC=C1 LZDKOEFJMQLXLN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
FXULEYVOQYTJJD-UHFFFAOYSA-N C1(CCCCC1)C(=O)C1=C(C(=CC(=C1)OC)Cl)Cl Chemical compound C1(CCCCC1)C(=O)C1=C(C(=CC(=C1)OC)Cl)Cl FXULEYVOQYTJJD-UHFFFAOYSA-N 0.000 description 1
PFNUWJZKUOPHBS-UHFFFAOYSA-N C1=CC=C(C=C1)C(CBr)C(=O)Br Chemical compound C1=CC=C(C=C1)C(CBr)C(=O)Br PFNUWJZKUOPHBS-UHFFFAOYSA-N 0.000 description 1
HPZBURRVSHAKEI-UHFFFAOYSA-N C1=CC=C(C=C1)C2=C3C(=CC(=C2)OCC(=O)O)C4=CC=CC=C4C3=O Chemical compound C1=CC=C(C=C1)C2=C3C(=CC(=C2)OCC(=O)O)C4=CC=CC=C4C3=O HPZBURRVSHAKEI-UHFFFAOYSA-N 0.000 description 1
MDAATRUKCHVFSA-UHFFFAOYSA-N C1CC(C2=CC=CC=C21)(C3=CC=CS3)C(=O)O Chemical compound C1CC(C2=CC=CC=C21)(C3=CC=CS3)C(=O)O MDAATRUKCHVFSA-UHFFFAOYSA-N 0.000 description 1
AHRHUNXJTOTXFN-UHFFFAOYSA-N CC1(CC2=CC(=C(C(=C2C1)Cl)Cl)OCC(=O)O)C3=CC=C(C=C3)N=O Chemical compound CC1(CC2=CC(=C(C(=C2C1)Cl)Cl)OCC(=O)O)C3=CC=C(C=C3)N=O AHRHUNXJTOTXFN-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YWADMZFJVNHRNT-UHFFFAOYSA-N ClC1=C(C=CC(=C1Cl)OC)C(C(=C)C1=CC=CC=C1)=O.C1(=CC=CC=C1)C1C(C2=C(C(=C(C=C2C1)OC)Cl)Cl)=O Chemical compound ClC1=C(C=CC(=C1Cl)OC)C(C(=C)C1=CC=CC=C1)=O.C1(=CC=CC=C1)C1C(C2=C(C(=C(C=C2C1)OC)Cl)Cl)=O YWADMZFJVNHRNT-UHFFFAOYSA-N 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
241001279009 Strychnos toxifera Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
229940116731 Uricosuric agent Drugs 0.000 description 1
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 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
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
FSVKRVWUMCWDIA-UHFFFAOYSA-N bis[5-(1-bromocyclohexyl)-2,3-dichloro-4-methoxyphenyl]methanone Chemical compound COC1=C(Cl)C(Cl)=C(C(=O)C=2C(=C(Cl)C(OC)=C(C=2)C2(Br)CCCCC2)Cl)C=C1C1(Br)CCCCC1 FSVKRVWUMCWDIA-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
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 1
239000007810 chemical reaction solvent Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
239000013058 crude material Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
SQDLGFFLAUHDDL-UHFFFAOYSA-N cyclohexen-1-yl-(2,3-dichloro-4-methoxyphenyl)methanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C1=CCCCC1 SQDLGFFLAUHDDL-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
WMESGGAPKSNDLL-UHFFFAOYSA-M dithiophen-2-yliodanium;chloride Chemical compound [Cl-].C=1C=CSC=1[I+]C1=CC=CS1 WMESGGAPKSNDLL-UHFFFAOYSA-M 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
239000011356 non-aqueous organic solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
ROMWNDGABOQKIW-UHFFFAOYSA-N phenyliodanuidylbenzene Chemical group C=1C=CC=CC=1[I-]C1=CC=CC=C1 ROMWNDGABOQKIW-UHFFFAOYSA-N 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class 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
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000565 sealant Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229960005453 strychnine Drugs 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000003383 uricosuric agent Substances 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000036325 urinary excretion Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI2789/74A 1973-10-11 1974-09-25 Foerfarande foer framstaellning av diuretisk eller saluretisk (1-oxo-2-fenyl- eller -tienyl-2-substituerad-5-indanyloxi)aettiksyra eller dess derivat FI61866C (fi)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
FI800415A FI60388C (fi)	1973-10-11	1980-02-11	Foerfarande foer framstaellning av (1-oxo-2-(4-hydroxifenyl)-2-metyl-6,7-diklor-5-indanyloxi)aettiksyra med diuretisk och saluretisk verkan

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US40573673A	1973-10-11	1973-10-11
US40573673		1973-10-11
US49265174A	1974-07-30	1974-07-30
US49265374A	1974-07-30	1974-07-30
US49265174		1974-07-30
US05/492,652 US3981888A (en)	1974-07-30	1974-07-30	Process for preparing (1-oxo-2-phenyl, halophenyl or thienyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid
US49265374		1974-07-30
US49265274		1974-07-30

Publications (3)

Publication Number	Publication Date
FI278974A7 FI278974A7 (da)	1975-04-12
FI61866B FI61866B (fi)	1982-06-30
FI61866C true FI61866C (fi)	1982-10-11

Family

ID=27503519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI2789/74A FI61866C (fi)	1973-10-11	1974-09-25	Foerfarande foer framstaellning av diuretisk eller saluretisk (1-oxo-2-fenyl- eller -tienyl-2-substituerad-5-indanyloxi)aettiksyra eller dess derivat

Country Status (4)

Country	Link
DK (1)	DK143553C (da)
FI (1)	FI61866C (da)
NO (1)	NO147747C (da)
SE (1)	SE423990B (da)

1974
- 1974-09-25 SE SE7412046A patent/SE423990B/xx not_active IP Right Cessation
- 1974-09-25 FI FI2789/74A patent/FI61866C/fi active
- 1974-09-26 DK DK506674A patent/DK143553C/da not_active IP Right Cessation
- 1974-09-27 NO NO743495A patent/NO147747C/no unknown

Also Published As

Publication number	Publication date
DK506674A (da)	1975-06-09
NO147747B (no)	1983-02-28
NO743495L (da)	1975-05-05
DK143553C (da)	1982-02-15
NO147747C (no)	1983-06-08
FI278974A7 (da)	1975-04-12
DK143553B (da)	1981-09-07
SE7412046L (da)	1975-04-14
FI61866B (fi)	1982-06-30
SE423990B (sv)	1982-06-21

Publication	Publication Date	Title
US4096267A (en)	1978-06-20	(1-Oxo-2-aryl or thienyl-2-substituted-5-indanyloxy (or thio) alkanoic acids, and derivatives thereof
FI72712B (fi)	1987-03-31	Foerfarande foer framstaellning av estrar av 2-(6'-metoxi-2'-naftyl-propionsyra med hjaelp av omlagring av nya ketaler av 2-halogen-1-(6'-metoxi-2'-naftyl)-propan-1-on samt nya ketaler.
Kwang et al.	1982	Calixarenes. 8. Short, stepwise synthesis of p-phenylcalix [4] arene and p-phenyl-p-tert-butylcalix [4] arene and derived products
AU2007344310B2 (en)	2013-08-15	Substituted 3-phenyl-1-(phenylthienyl)propan-1-one and 3-phenyl-1-(phenylfuranyl)propan-1-one derivatives, and preparation and use of same
Stacy et al.	1965	2-Aminobenzo [b] thiophene. An aromatic ring tautomer1, 2
JPS6412264B2 (da)	1989-02-28
Elias et al.	1988	Synthesis and anti-inflammatory activity of substituted (E)-4-phenyl-3-buten-2-ones
US4182764A (en)	1980-01-08	Tetrazole derivatives of [1-oxo-2-aryl or thienyl-2-substituted-5-indanyloxy(or thio)]alkanoic acids
Jutz	2006	Aromatic and heteroaromatic compounds by electrocyclic ring-closure with elimination
FI60195B (fi)	1981-08-31	Foerfarande foer framstaellning av substituerade fenylaettiksyror med inflammationshaemmande verkan
US4177285A (en)	1979-12-04	[1-Oxo-2-thienyl-2-substituted-5-indanyloxy (or thio)]alkanoic acids and derivatives thereof
FI61866C (fi)	1982-10-11	Foerfarande foer framstaellning av diuretisk eller saluretisk (1-oxo-2-fenyl- eller -tienyl-2-substituerad-5-indanyloxi)aettiksyra eller dess derivat
Keserü et al.	1992	Total synthesis of plagiochins C and D, macrocyclic bis (bibenzyl) constituents of plagiochila acantophylla
DK146444B (da)	1983-10-10	Analogifremgangsmaade til fremstilling af 1-oxo-2,3-hydrocarbylen-5-indanyloxy-eddikesyrer eller salte deraf med baser
Koparır et al.	2004	Cyclobutane‐substituted diacetamido sulfides and 2, 5‐diacylthiophenes
CA2513310C (en)	2012-11-27	Indenoncarboxylic acids derivatives and their use for the treatment of and preventing diabetes and dyslipidaemia
Grützmacher et al.	1994	A convenient synthesis of macrocyclic [2.1. 2.1] paracyclophanes
KR870000034B1 (ko)	1987-02-07	〔1-옥소-2-아릴 또는 티에닐-2-치환-5-인다닐옥시〕알칸산의 제조방법
FI80882C (fi)	1990-08-10	Foerfarande foer framstaellning av 2-tiofenaettiksyraderivat.
US3947469A (en)	1976-03-30	3-(1,3-Dithian-2-yl)-4-cyclo-pentene-2-carboxylic acids, esters and amides
Tseng et al.	1973	Synthesis of aminobenzofurans and aminonaphtho [1, 2-b] furans
US4013692A (en)	1977-03-22	Certain 3-phenyl-benzofuran lower alkanoic acids and esters thereof
US4133959A (en)	1979-01-09	Aryloxyalkyl diketones
FI56671C (fi)	1980-03-10	Foerfarande foer framstaellning av indan-1-karboxylsyraderivat
Ramadas et al.	1987	NEW POLYHETEROPOLYCYCLIC RING SYSTEMS PART XXV. SYNTHESIS OF STEROID-TYPE COMPOUNDS DERIVED FROM 5, 5-DIMETHYL-2, 3, 5, 6-TETRAHYDRO-4H-THIOPYRANO [3, 2-g]-BENZTHIADIAZOLE-4-ONE