CH617689A5 - - Google Patents

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Publication number: CH617689A5
Authority: CH; Switzerland
Prior art keywords: dichloro; methyl; phenyl; compounds; lower alkyl
Prior art date: 1975-02-24

Application number

CH193776A

Other languages

German (de)

English (en)

Inventor

Edward Jethro Cragoe Jr

Otto William Woltersdorf Jr

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.)

1975-02-24

Filing date

1976-02-17

Publication date

1980-06-13

1976-02-17 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1980-06-13 Publication of CH617689A5 publication Critical patent/CH617689A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 48
-1 alkyl radical Chemical class 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 22
SMNDYUVBFMFKNZ-UHFFFAOYSA-N pyromucic acid Natural products OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
238000000034 method Methods 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
150000003973 alkyl amines Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 4
150000005840 aryl radicals Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
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 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
125000000068 chlorophenyl group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 26
239000000243 solution Substances 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000000155 melt Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000001953 recrystallisation Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 14
AYQFTEQCBBWCNZ-UHFFFAOYSA-N 2H-indeno[2,1-b]furan Chemical class C1=CC=C2C3=CCOC3=CC2=C1 AYQFTEQCBBWCNZ-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 8
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
239000002934 diuretic Substances 0.000 description 7
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 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000003814 drug Substances 0.000 description 5
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
229910001414 potassium ion Inorganic materials 0.000 description 5
230000000894 saliuretic effect Effects 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 description 4
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 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
ACHKKGDWZVCSNH-UHFFFAOYSA-N amiloride hydrochloride Chemical compound Cl.NC(N)=NC(=O)C1=NC(Cl)=C(N)N=C1N ACHKKGDWZVCSNH-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
229940030606 diuretics Drugs 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 3
WZAAIPGXMLXIOD-UHFFFAOYSA-N 2h-cyclopenta[e][1]benzofuran-2-carboxylic acid Chemical compound C1=C2C=CC=C2C2=CC(C(=O)O)OC2=C1 WZAAIPGXMLXIOD-UHFFFAOYSA-N 0.000 description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 3
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 3
229960004104 amiloride hydrochloride Drugs 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000037396 body weight Effects 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
WNBSDCKJFDZMHT-UHFFFAOYSA-N n-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound NC(N)=NC(=O)C1=CN=CC=N1 WNBSDCKJFDZMHT-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910001415 sodium ion Inorganic materials 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
YBQTZXQUEQSBCJ-UHFFFAOYSA-N 1-(2,3-dichloro-4-methoxyphenyl)-2-methylprop-2-en-1-one Chemical compound COC1=CC=C(C(=O)C(C)=C)C(Cl)=C1Cl YBQTZXQUEQSBCJ-UHFFFAOYSA-N 0.000 description 2
LTVRGAWOEOKGJZ-UHFFFAOYSA-N 1-chloro-3-methoxy-2-methylbenzene Chemical compound COC1=CC=CC(Cl)=C1C LTVRGAWOEOKGJZ-UHFFFAOYSA-N 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
BLMBNEVGYRXFNA-UHFFFAOYSA-N 1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC=CC(C)=C1C BLMBNEVGYRXFNA-UHFFFAOYSA-N 0.000 description 2
WIHSAOYVGKVRJX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1Cl WIHSAOYVGKVRJX-UHFFFAOYSA-N 0.000 description 2
BGGKEDDFKBVTDK-UHFFFAOYSA-N 2-(3-methylphenyl)acetyl chloride Chemical compound CC1=CC=CC(CC(Cl)=O)=C1 BGGKEDDFKBVTDK-UHFFFAOYSA-N 0.000 description 2
UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 2
SIOJFYRPBYGHOO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetyl chloride Chemical compound FC1=CC=C(CC(Cl)=O)C=C1 SIOJFYRPBYGHOO-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
YYGRRRBCAPNFRK-UHFFFAOYSA-N 2-chloro-1-methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1Cl YYGRRRBCAPNFRK-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
ONXWHKYJIVVFPF-UHFFFAOYSA-N 2H-cyclopenta[e][1]benzofuran Chemical compound C1=C2C(OC1)=CC=C1C=CC=C12 ONXWHKYJIVVFPF-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
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 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000005821 Claisen rearrangement reaction Methods 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
201000005569 Gout Diseases 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
238000006683 Mannich reaction Methods 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
229940116731 Uricosuric agent Drugs 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
239000012050 conventional carrier Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
WMESGGAPKSNDLL-UHFFFAOYSA-M dithiophen-2-yliodanium;chloride Chemical compound [Cl-].C=1C=CSC=1[I+]C1=CC=CS1 WMESGGAPKSNDLL-UHFFFAOYSA-M 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000029142 excretion Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 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
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 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
230000003287 optical effect Effects 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
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238000011287 therapeutic dose Methods 0.000 description 2
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GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
229940116269 uric acid Drugs 0.000 description 2
239000003383 uricosuric agent Substances 0.000 description 2
LDDMACCNBZAMSG-BDVNFPICSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO LDDMACCNBZAMSG-BDVNFPICSA-N 0.000 description 1
KWTSXDURSIMDCE-MRVPVSSYSA-N (R)-amphetamine Chemical compound C[C@@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-MRVPVSSYSA-N 0.000 description 1
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
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 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
QDZAWVLWIMOXJT-UHFFFAOYSA-N 2-(4-methylphenyl)acetyl chloride Chemical compound CC1=CC=C(CC(Cl)=O)C=C1 QDZAWVLWIMOXJT-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
RNXIRXYZZGOBQG-UHFFFAOYSA-N 2h-indeno[2,1-b]thiophene Chemical class C1=CC=C2C3=CCSC3=CC2=C1 RNXIRXYZZGOBQG-UHFFFAOYSA-N 0.000 description 1
HGGLRBRQBKQOEP-UHFFFAOYSA-N 2h-indeno[2,1-b]thiophene-2-carboxylic acid Chemical compound C1=CC=C2C3=CC(C(=O)O)SC3=CC2=C1 HGGLRBRQBKQOEP-UHFFFAOYSA-N 0.000 description 1
IOCFOSLKHLCEJC-UHFFFAOYSA-N 4,5-dichloro-2-(hydroxymethyl)-7-methyl-7-phenyl-2,8-dihydro-1h-cyclopenta[e][1]benzofuran-6-one Chemical compound C1C2=C3CC(CO)OC3=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 IOCFOSLKHLCEJC-UHFFFAOYSA-N 0.000 description 1
VAIJWKARKIGGET-UHFFFAOYSA-N 4,5-dichloro-7-methyl-6-oxo-7-phenyl-2,8-dihydro-1h-cyclopenta[e][1]benzofuran-2-carboxylic acid Chemical compound C1C2=C3CC(C(O)=O)OC3=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 VAIJWKARKIGGET-UHFFFAOYSA-N 0.000 description 1
QOPRWBRNMPANKN-UHFFFAOYSA-N 5-methoxy-2,3-dihydroinden-1-one Chemical class COC1=CC=C2C(=O)CCC2=C1 QOPRWBRNMPANKN-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
206010014418 Electrolyte imbalance Diseases 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
201000001431 Hyperuricemia Diseases 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
208000010428 Muscle Weakness Diseases 0.000 description 1
206010028372 Muscular weakness Diseases 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-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
206010030113 Oedema Diseases 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
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 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
238000010521 absorption reaction Methods 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 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
229960002576 amiloride Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
239000011575 calcium Substances 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 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
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
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000012955 diaryliodonium Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-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
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
229940012017 ethylenediamine Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910001416 lithium ion Inorganic materials 0.000 description 1
230000007774 longterm Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000006069 physical mixture Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 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
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000003424 uricosuric effect Effects 0.000 description 1

Classifications

- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH193776A 1975-02-24 1976-02-17 CH617689A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/552,402 US3984552A (en)	1975-02-24	1975-02-24	6-Oxo-7-substituted and 7,7-disubstituted-6H-indeno-[5,4-b]furan (and thiophene) carboxylic acids

Publications (1)

Publication Number	Publication Date
CH617689A5 true CH617689A5 (fr)	1980-06-13

Family

ID=24205173

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH193776A CH617689A5 (fr)	1975-02-24	1976-02-17

Country Status (15)

Country	Link
US (1)	US3984552A (fr)
JP (1)	JPS6154794B2 (fr)
AU (1)	AU500514B2 (fr)
BE (1)	BE838828A (fr)
CA (1)	CA1072972A (fr)
CH (1)	CH617689A5 (fr)
DE (1)	DE2607305C2 (fr)
DK (1)	DK143339C (fr)
ES (1)	ES445380A1 (fr)
FR (1)	FR2301246A1 (fr)
GB (1)	GB1497382A (fr)
HU (1)	HU177120B (fr)
NL (1)	NL7601295A (fr)
SE (1)	SE425605B (fr)
ZA (1)	ZA761046B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1975
- 1975-02-24 US US05/552,402 patent/US3984552A/en not_active Expired - Lifetime
1976
- 1976-02-09 NL NL7601295A patent/NL7601295A/xx not_active Application Discontinuation
- 1976-02-10 SE SE7601422A patent/SE425605B/xx not_active IP Right Cessation
- 1976-02-11 DK DK56076A patent/DK143339C/da not_active IP Right Cessation
- 1976-02-13 HU HU76ME1946A patent/HU177120B/hu unknown
- 1976-02-17 AU AU11179/76A patent/AU500514B2/en not_active Expired
- 1976-02-17 CH CH193776A patent/CH617689A5/de not_active IP Right Cessation
- 1976-02-18 CA CA246,059A patent/CA1072972A/fr not_active Expired
- 1976-02-19 GB GB6654/76A patent/GB1497382A/en not_active Expired
- 1976-02-20 ES ES445380A patent/ES445380A1/es not_active Expired
- 1976-02-23 ZA ZA761046A patent/ZA761046B/xx unknown
- 1976-02-23 FR FR7604937A patent/FR2301246A1/fr active Granted
- 1976-02-23 DE DE2607305A patent/DE2607305C2/de not_active Expired
- 1976-02-23 BE BE164538A patent/BE838828A/fr not_active IP Right Cessation
- 1976-02-24 JP JP51018581A patent/JPS6154794B2/ja not_active Expired

Also Published As

Publication number	Publication date
FR2301246B1 (fr)	1980-06-20
ZA761046B (en)	1977-03-30
ES445380A1 (es)	1977-10-01
DE2607305A1 (de)	1976-09-02
HU177120B (en)	1981-07-28
AU1117976A (en)	1977-08-25
DK143339B (da)	1981-08-10
JPS51110558A (fr)	1976-09-30
SE7601422L (sv)	1976-08-25
SE425605B (sv)	1982-10-18
AU500514B2 (en)	1979-05-24
NL7601295A (nl)	1976-08-26
US3984552A (en)	1976-10-05
CA1072972A (fr)	1980-03-04
GB1497382A (en)	1978-01-12
BE838828A (fr)	1976-08-23
DK56076A (da)	1976-08-25
DE2607305C2 (de)	1987-04-30
DK143339C (da)	1981-12-07
FR2301246A1 (fr)	1976-09-17
JPS6154794B2 (fr)	1986-11-25

Legal Events

Date	Code	Title	Description
1992-10-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
CH624949A5 (fr)	1981-08-31
DE1470157A1 (de)	1969-05-14	Verfahren zur Herstellung substituierter Thioxanthensulfonamide und ihrer Saeureanlagerungssalze
DE2607305C2 (de)	1987-04-30	6-Oxo-6H-indeno[5,4-b]furan-2-carbonsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2624693A1 (de)	1977-07-14	Isochromanderivate und verfahren zu deren herstellung
DE3411993A1 (de)	1985-10-10	Substituierte benzopyrane, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimittel
DE2757680A1 (de)	1979-06-28	Neue 2-oxo-1-pyrrolidinessigsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3586411T2 (de)	1993-01-07	Dopamin-antagoniste.
DE2351411C2 (de)	1983-04-21	(1-Oxo-2,3-hydrocarbylen-6,7-dichlor-5- indanyloxy)-essigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
DE2523103A1 (de)	1976-12-09	Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
DE2839279A1 (de)	1979-03-29	Derivate des 1,2,3,3a,8,8a-hexahydropyrrolo eckige klammer auf 2,3-b eckige klammer zu indols, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
DE2426505A1 (de)	1975-01-09	Derivate der 1,3-benzodioxol-2-carbonsaeure
DE3587138T2 (de)	1993-09-09	Polycyclische verbindungen, ihre herstellung und sie enthaltende rezepturen.
EP0025109B1 (fr)	1985-05-15	Dérivés de 1-benzoxépin-5(2H)-ones et leurs sels, et procédés pour leur préparation
AT391316B (de)	1990-09-25	Neue thienyloxy-alkylamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2449205A1 (de)	1975-04-24	Diaromatische o-(aminoalkyl)-oxime, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen
DE2117358A1 (de)	1971-10-28	4-Aminomethyl-spiro eckige Klammer auf dibenzo eckige Klammer auf a,d eckige Klammer zu cycloheptadi-(oder tri) en-5,2-(1,3-dioxolan) eckige Klammer zu -Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittelwirkstoff
DE1915230B2 (de)	1978-02-23	Hydroxyphenylalkylaminderivate, verfahren zu deren herstellung und arzneimittel auf deren basis
EP0088323B1 (fr)	1987-05-06	Amides d'acides imidazothiadiazolealcanecarboxyliques, produits intermédiaires pour leur fabrication, leur fabrication et leur application en médicaments
DE2303427A1 (de)	1973-08-16	Dibenzo-(a,d)-cycloheptadiene und -triene, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
DE2029510C3 (de)	1980-06-19	Dibenzofuranderivate und deren pharmazeutisch verträgliche Säureadditionssalze sowie Verfahren zu deren Herstellung und Arzneimittel mit einem Gehalt dieser Verbindungen
DE69520876T2 (de)	2002-02-21	Gamma-diketonverbindung mit thrombozytenaggregationshemmender wirkung
DE3248094C1 (de)	1984-06-14	7H-Dibenzo(a,c)cyclohepten-5-on(7)-Derivate,Verfahren zu deren Herstellung und deren Verwendung bei der Bekaempfung psychischer Erkrankungen und von Magen-und/oder Darmgeschwueren
DE2166662A1 (de)	1975-01-23	Tricyclische derivate von aliphatischen omega-alkoholen und verfahren zu ihrer herstellung
DE3425452A1 (de)	1986-01-23	Phenylethylaminopropiophenon-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel