CH646421A5 - Thioalkanoylalkansaeureverbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel. - Google Patents

Thioalkanoylalkansaeureverbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel. Download PDF

Info

Publication number: CH646421A5
Authority: CH; Switzerland
Prior art keywords: compounds according; value; hydrogen atoms; acid; compounds
Prior art date: 1978-03-27

Application number

CH1302878A

Other languages

German (de)

English (en)

Inventor

Michael Edward Condon

Miguel Angel Ondetti

Original Assignee

Squibb & Sons 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.)

1978-03-27

Filing date

1978-12-21

Publication date

1984-11-30

1978-12-21 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1984-11-30 Publication of CH646421A5 publication Critical patent/CH646421A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 63
239000002253 acid Substances 0.000 title claims description 21
238000000034 method Methods 0.000 title claims description 15
229940126601 medicinal product Drugs 0.000 title 1
239000000203 mixture Substances 0.000 claims description 58
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 21
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 100
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 80
239000000243 solution Substances 0.000 description 74
239000003921 oil Substances 0.000 description 52
235000019198 oils Nutrition 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
239000000047 product Substances 0.000 description 40
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
-1 alkanoyl radical Chemical class 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
239000010410 layer Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000000741 silica gel Substances 0.000 description 27
229910002027 silica gel Inorganic materials 0.000 description 27
239000000463 material Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 19
238000001816 cooling Methods 0.000 description 18
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
239000002178 crystalline material Substances 0.000 description 13
239000012044 organic layer Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
239000007787 solid Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000000908 ammonium hydroxide Substances 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
229910000343 potassium bisulfate Inorganic materials 0.000 description 7
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
LNKQHINVIVNFGD-GUJYYOPSSA-N (1r,2r)-2-(3-acetylsulfanyl-2-methylpropanoyl)cyclohexane-1-carboxylic acid Chemical compound CC(=O)SCC(C)C(=O)[C@@H]1CCCC[C@H]1C(O)=O LNKQHINVIVNFGD-GUJYYOPSSA-N 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
239000005977 Ethylene Substances 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 6
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
238000004821 distillation Methods 0.000 description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
KGTDSOQGIXSSNO-NXEZZACHSA-N (1r,2r)-2-(3-acetylsulfanylpropanoyl)cyclohexane-1-carboxylic acid Chemical compound CC(=O)SCCC(=O)[C@@H]1CCCC[C@H]1C(O)=O KGTDSOQGIXSSNO-NXEZZACHSA-N 0.000 description 4
LHOLEONMIKFQIF-UHFFFAOYSA-N 6-acetylsulfanyl-4-oxohexanoic acid Chemical compound CC(=O)SCCC(=O)CCC(O)=O LHOLEONMIKFQIF-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229940117975 chromium trioxide Drugs 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
SNWJQIQVLLKOKM-RNFRBKRXSA-N (1r,2r)-2-(2-sulfanylacetyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1C(=O)CS SNWJQIQVLLKOKM-RNFRBKRXSA-N 0.000 description 3
RQQKHZYZISXLAD-PHDIDXHHSA-N (1r,2r)-2-(3-sulfanylpropanoyl)cyclobutane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CC[C@H]1C(=O)CCS RQQKHZYZISXLAD-PHDIDXHHSA-N 0.000 description 3
NDKQKQJPRJGDLG-HTQZYQBOSA-N (1r,2r)-2-(3-sulfanylpropanoyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1C(=O)CCS NDKQKQJPRJGDLG-HTQZYQBOSA-N 0.000 description 3
LMEHQSIFTHFMQS-UHFFFAOYSA-N 4-oxohex-5-enoic acid Chemical compound OC(=O)CCC(=O)C=C LMEHQSIFTHFMQS-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
239000007818 Grignard reagent Substances 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
WPTPRESBMDGEQD-MGRQHWMJSA-N (1r,2r)-2-(1-hydroxy-2-methylprop-2-enyl)cyclohexane-1-carboxylic acid Chemical compound CC(=C)C(O)[C@@H]1CCCC[C@H]1C(O)=O WPTPRESBMDGEQD-MGRQHWMJSA-N 0.000 description 2
WLQOEPGGWNHJGZ-CFCGPWAMSA-N (1r,2r)-2-(2-methyl-3-sulfanylpropanoyl)cyclohexane-1-carboxylic acid Chemical compound SCC(C)C(=O)[C@@H]1CCCC[C@H]1C(O)=O WLQOEPGGWNHJGZ-CFCGPWAMSA-N 0.000 description 2
LAHFUCPFJAURPL-RKDXNWHRSA-N (1r,2r)-2-(3-acetylsulfanylpropanoyl)cyclopentane-1-carboxylic acid Chemical compound CC(=O)SCCC(=O)[C@@H]1CCC[C@H]1C(O)=O LAHFUCPFJAURPL-RKDXNWHRSA-N 0.000 description 2
CATDZUWIADLDNG-RNFRBKRXSA-N (1r,2r)-2-(3-sulfanylpropanoyl)cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)CCS CATDZUWIADLDNG-RNFRBKRXSA-N 0.000 description 2
BOVPVRGRPPYECC-RNFRBKRXSA-N (1r,2r)-2-methoxycarbonylcyclohexane-1-carboxylic acid Chemical compound COC(=O)[C@@H]1CCCC[C@H]1C(O)=O BOVPVRGRPPYECC-RNFRBKRXSA-N 0.000 description 2
MUTGBJKUEZFXGO-WDSKDSINSA-N (3as,7as)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@H]21 MUTGBJKUEZFXGO-WDSKDSINSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
SGXMEMIIHIDHDJ-YHNBSYBMSA-N 2-[3-[[3-[(1r,2r)-2-carboxycyclohexyl]-3-oxopropyl]disulfanyl]propanoyl]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)CCSSCCC(=O)[C@H]1[C@H](C(O)=O)CCCC1 SGXMEMIIHIDHDJ-YHNBSYBMSA-N 0.000 description 2
GORGSUGLHDAEQO-UHFFFAOYSA-N 4-oxo-6-sulfanylhexanoic acid Chemical compound OC(=O)CCC(=O)CCS GORGSUGLHDAEQO-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
108010064733 Angiotensins Proteins 0.000 description 2
102000015427 Angiotensins Human genes 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
150000001844 chromium Chemical class 0.000 description 2
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
JDHOCWRIAQDGEY-UHFFFAOYSA-N cyclopentene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCC1 JDHOCWRIAQDGEY-UHFFFAOYSA-N 0.000 description 2
238000004042 decolorization Methods 0.000 description 2
238000001514 detection method Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
DGHWGHPZRYEZDI-JGVFFNPUSA-N methyl (1R,2R)-2-formylcyclohexane-1-carboxylate Chemical compound C(=O)[C@H]1[C@@H](CCCC1)C(=O)OC DGHWGHPZRYEZDI-JGVFFNPUSA-N 0.000 description 2
OWNNQFMHLFDOKY-NKWVEPMBSA-N methyl (1r,2r)-2-formylcyclopentane-1-carboxylate Chemical compound COC(=O)[C@@H]1CCC[C@H]1C=O OWNNQFMHLFDOKY-NKWVEPMBSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
WLGGHBQPWGTFRH-GCJDJSOWSA-N (1r,2r)-2-(1-hydroxyprop-2-enyl)cyclopentane-1-carboxylic acid Chemical compound C=CC(O)[C@@H]1CCC[C@H]1C(O)=O WLGGHBQPWGTFRH-GCJDJSOWSA-N 0.000 description 1
IFOLMFDGXWBJGJ-HTQZYQBOSA-N (1r,2r)-2-prop-2-enoylcyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1C(=O)C=C IFOLMFDGXWBJGJ-HTQZYQBOSA-N 0.000 description 1
MWZMEYJIRMEBRH-RNFRBKRXSA-N (1r,2r)-2-prop-2-enoylcyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C=C MWZMEYJIRMEBRH-RNFRBKRXSA-N 0.000 description 1
ASJCSAKCMTWGAH-RFZPGFLSSA-N (1r,2r)-cyclopentane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(O)=O ASJCSAKCMTWGAH-RFZPGFLSSA-N 0.000 description 1
NMSRALOLNIBERV-SYDPRGILSA-N (3as,6ar)-4,5,6,6a-tetrahydro-3ah-cyclopenta[c]furan-1,3-dione Chemical compound C1CC[C@@H]2C(=O)OC(=O)[C@@H]21 NMSRALOLNIBERV-SYDPRGILSA-N 0.000 description 1
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IKKJHPGBHKMIFM-UHFFFAOYSA-N 2,2-dibromoethenone Chemical compound BrC(Br)=C=O IKKJHPGBHKMIFM-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
FMDKREDOOZUHMD-UHFFFAOYSA-N 2-acetylsulfanylcyclohexane-1-carboxylic acid Chemical compound CC(=O)SC1CCCCC1C(O)=O FMDKREDOOZUHMD-UHFFFAOYSA-N 0.000 description 1
PHMRPWPDDRGGGF-UHFFFAOYSA-N 2-bromoprop-1-ene Chemical compound CC(Br)=C PHMRPWPDDRGGGF-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
ZYJSTSMEUKNCEV-UHFFFAOYSA-N 3-diazo-1-diazonioprop-1-en-2-olate Chemical compound [N-]=[N+]=CC(=O)C=[N+]=[N-] ZYJSTSMEUKNCEV-UHFFFAOYSA-N 0.000 description 1
PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
NMNZZIMBGSGRPN-UHFFFAOYSA-N 3-oxabicyclo[3.2.0]heptane-2,4-dione Chemical compound O=C1OC(=O)C2CCC12 NMNZZIMBGSGRPN-UHFFFAOYSA-N 0.000 description 1
FHSUFDYFOHSYHI-UHFFFAOYSA-N 3-oxopentanoic acid Chemical class CCC(=O)CC(O)=O FHSUFDYFOHSYHI-UHFFFAOYSA-N 0.000 description 1
102000005862 Angiotensin II Human genes 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
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244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
235000003434 Sesamum indicum Nutrition 0.000 description 1
NIDINIHOPRFWFJ-SFYZADRCSA-N [(1r,2r)-2-methylcyclohexyl]methanol Chemical compound C[C@@H]1CCCC[C@H]1CO NIDINIHOPRFWFJ-SFYZADRCSA-N 0.000 description 1
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 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
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239000013543 active substance Substances 0.000 description 1
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229910052783 alkali metal Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
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150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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238000010171 animal model Methods 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
HCIWSLYRQVKYDT-LEAGNCFPSA-N benzhydryl (1R,2R)-2-(1-hydroxyprop-2-enyl)cyclopentane-1-carboxylate Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)[C@H]1[C@@H](CCC1)C(C=C)O HCIWSLYRQVKYDT-LEAGNCFPSA-N 0.000 description 1
HSZGCPVDLXEEMZ-UHFFFAOYSA-N benzhydryl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 HSZGCPVDLXEEMZ-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 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
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238000011109 contamination Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
GQPRMLJTQCSXQR-PHDIDXHHSA-N methyl (1r,2r)-2-(dibromomethyl)cyclopentane-1-carboxylate Chemical compound COC(=O)[C@@H]1CCC[C@H]1C(Br)Br GQPRMLJTQCSXQR-PHDIDXHHSA-N 0.000 description 1
KZNXMMWIDJRYAG-JGVFFNPUSA-N methyl (1r,2r)-2-(hydroxymethyl)cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1CCCC[C@H]1CO KZNXMMWIDJRYAG-JGVFFNPUSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000010409 thin film Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/53—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Inorganic Compounds Of Heavy Metals (AREA)

CH1302878A 1978-03-27 1978-12-21 Thioalkanoylalkansaeureverbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel. CH646421A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US89044678A	1978-03-27	1978-03-27

Publications (1)

Publication Number	Publication Date
CH646421A5 true CH646421A5 (de)	1984-11-30

Family

ID=25396691

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1302878A CH646421A5 (de)	1978-03-27	1978-12-21	Thioalkanoylalkansaeureverbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel.

Country Status (16)

Country	Link
JP (1)	JPS54128516A (fr)
AU (1)	AU522896B2 (fr)
BE (1)	BE873219A (fr)
CA (1)	CA1125783A (fr)
CH (1)	CH646421A5 (fr)
DE (1)	DE2855835A1 (fr)
DK (1)	DK586778A (fr)
FR (2)	FR2435467A1 (fr)
GB (1)	GB2017081B (fr)
IE (1)	IE48041B1 (fr)
IT (1)	IT1110882B (fr)
LU (1)	LU80731A1 (fr)
NL (1)	NL7812598A (fr)
NO (1)	NO784398L (fr)
SE (1)	SE7813279L (fr)
ZA (1)	ZA786929B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4235885A (en) *	1979-06-25	1980-11-25	E. R. Squibb & Sons, Inc.	Inhibitors of mammalian collagenase
FR2605630B1 (fr) *	1986-10-22	1989-06-30	Roussel Uclaf	Procede de preparation de derives de l'octahydroindole et intermediaires de preparation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB762575A (en) *	1952-04-24	1956-11-28	American Cyanamid Co	Omega [3-(1,2-dithiolanyl)] aliphatic acids, salts and esters and the preparation thereof
US2828321A (en) *	1953-10-19	1958-03-25	American Cyanamid Co	Keto aliphatic acid esters and method of preparing the same

1978
- 1978-12-08 CA CA317,663A patent/CA1125783A/fr not_active Expired
- 1978-12-11 ZA ZA00786929A patent/ZA786929B/xx unknown
- 1978-12-15 IE IE2481/78A patent/IE48041B1/en unknown
- 1978-12-15 AU AU42604/78A patent/AU522896B2/en not_active Expired
- 1978-12-21 CH CH1302878A patent/CH646421A5/de not_active IP Right Cessation
- 1978-12-22 DE DE19782855835 patent/DE2855835A1/de not_active Ceased
- 1978-12-22 SE SE7813279A patent/SE7813279L/xx not_active Application Discontinuation
- 1978-12-22 GB GB7849941A patent/GB2017081B/en not_active Expired
- 1978-12-27 JP JP16450578A patent/JPS54128516A/ja active Pending
- 1978-12-28 IT IT52478/78A patent/IT1110882B/it active
- 1978-12-28 LU LU80731A patent/LU80731A1/fr unknown
- 1978-12-28 NO NO784398A patent/NO784398L/no unknown
- 1978-12-28 NL NL7812598A patent/NL7812598A/xx not_active Application Discontinuation
- 1978-12-28 FR FR7836793A patent/FR2435467A1/fr active Granted
- 1978-12-29 DK DK586778A patent/DK586778A/da unknown
- 1978-12-29 BE BE192684A patent/BE873219A/fr not_active IP Right Cessation
1979
- 1979-04-02 FR FR7908240A patent/FR2421165A1/fr active Granted

Also Published As

Publication number	Publication date
LU80731A1 (fr)	1979-04-13
FR2435467B1 (fr)	1983-08-19
NL7812598A (nl)	1979-10-01
FR2421165A1 (fr)	1979-10-26
SE7813279L (sv)	1979-09-28
GB2017081B (en)	1982-07-28
AU522896B2 (en)	1982-07-01
JPS54128516A (en)	1979-10-05
DK586778A (da)	1979-09-28
IT7852478A0 (it)	1978-12-28
GB2017081A (en)	1979-10-03
IE48041B1 (en)	1984-09-05
IT1110882B (it)	1986-01-06
FR2421165B1 (fr)	1982-02-19
AU4260478A (en)	1979-10-04
IE782481L (en)	1979-09-27
ZA786929B (en)	1979-12-27
NO784398L (no)	1979-09-28
BE873219A (fr)	1979-06-29
CA1125783A (fr)	1982-06-15
DE2855835A1 (de)	1979-10-04
FR2435467A1 (fr)	1980-04-04

Legal Events

Date	Code	Title	Description
1987-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DD127966B3 (de)	1983-03-30	Verfahren zur herstellung von pyrrolidinderivaten
DE2807623C2 (de)	1982-07-01	2-Phenoxyphenyl-pyrrolidinderivate, deren Salze, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE1695044A1 (de)	1972-04-20	Verfahren zur Herstellung von neuen,substituierten Phenylessigsaeuren und deren Estern
DE69708130T2 (de)	2002-06-20	A-oxo-butansäuren enthaltende pharmazeutische zusammensetzung
EP0150015B1 (fr)	1987-06-16	Amides d'acides carboxyliques de norbornane et norbornène, et procédé de leur préparation
DE2854877A1 (de)	1979-06-28	N-substituierte omega-thiobutyramide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2511647A1 (de)	1975-09-25	Neue benzopyranderivate
DE3107743A1 (de)	1981-12-03	Neue klasse von acylderivaten des carnitins, verfahren zu deren herstellung sowie ihre therapeutische verwendung
CH621780A5 (fr)	1981-02-27
EP0086453B1 (fr)	1988-09-28	Dérivés de thiazaspiro, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0024030B1 (fr)	1983-03-30	Dérivés de la pyrrolidine, procédés pour leur préparation et compositions pharmaceutiques les contenant
CH646421A5 (de)	1984-11-30	Thioalkanoylalkansaeureverbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel.
CH517066A (de)	1971-12-31	Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäuren und ihren Alkali- und Erdalkalimetallsalzen
DE2113455A1 (de)	1971-10-07	Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansaeuren,ihren Salzen und funktionellen Derivaten
EP0009777A1 (fr)	1980-04-16	N-(carboxy)phényl amides de l'acide rétinoique et 7,8-déhydro-rétinoique, procédé de préparation et compositions pharmaceutiques les contenant
EP0371342B1 (fr)	1994-12-14	2-Halogéno N-indolyléthyl sulfonamides, procédé pour leur préparation et leur utilisation en thérapeutique
EP0339342A1 (fr)	1989-11-02	N-aminopyrrols N-substitués
DE2412388A1 (de)	1974-09-19	Dibenzothiophenderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE2458911A1 (de)	1975-06-26	11,12-secoprostaglandine und verfahren zu ihrer herstellung
EP0007347B1 (fr)	1981-12-30	Dérivés de alkylène glycol abaissant le taux en lipide et procédés pour leur préparation
EP0051247B1 (fr)	1985-01-09	Dérivés 4-thia- et 4-sulfinyl-PGI1, leur procédé de préparation et leurs compositions pharmaceutiques
DE3586150T2 (de)	1993-01-14	Amidderivate der 2-(p-aminobenzyl)-buttersaeure und ihrer ester mit blutfettgehaltsenkender wirkung.
DE2234706A1 (de)	1973-02-01	Derivate von 9-oxo-13-trans-prostensaeureestern
DE1643460C (de)	1972-05-04	(3-Trifluormethylphenoxy)-(4-chlorphenyl)-essigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0334147A1 (fr)	1989-09-27	Pyrroles disubstitués