IL34516A - Phenyl-imidazolyl-alkanoic acid derivatives,their production and pharmaceutical compositions containing them - Google Patents
Phenyl-imidazolyl-alkanoic acid derivatives,their production and pharmaceutical compositions containing themInfo
- Publication number
- IL34516A IL34516A IL34516A IL3451670A IL34516A IL 34516 A IL34516 A IL 34516A IL 34516 A IL34516 A IL 34516A IL 3451670 A IL3451670 A IL 3451670A IL 34516 A IL34516 A IL 34516A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- acid methyl
- imidazolyl
- acetic acid
- compounds according
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 57
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 150000004702 methyl esters Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 150000001722 carbon compounds Chemical class 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- -1 carbalkox Chemical group 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- OMLSYNQYPRJYAR-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 OMLSYNQYPRJYAR-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- IZPXHZWRFDQWLT-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1-morpholin-4-yl-2,2-diphenylethanone Chemical compound N=1C=CNC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(=O)N1CCOCC1 IZPXHZWRFDQWLT-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- PYWZPEZFSGYRGA-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2,2-bis(4-nitrophenyl)acetate;hydrochloride Chemical compound Cl.C=1C=C([N+]([O-])=O)C=CC=1C(C=1C=CC(=CC=1)[N+]([O-])=O)(C(=O)OCC)C1=NC=CN1 PYWZPEZFSGYRGA-UHFFFAOYSA-N 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- IQDLKFJCEIJFGN-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)C1=NC=CN1 IQDLKFJCEIJFGN-UHFFFAOYSA-N 0.000 description 6
- PRRHXUDAIBCCOD-UHFFFAOYSA-N propyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCC)C1=NC=CN1 PRRHXUDAIBCCOD-UHFFFAOYSA-N 0.000 description 6
- 241001480043 Arthrodermataceae Species 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 230000001857 anti-mycotic effect Effects 0.000 description 5
- 230000037304 dermatophytes Effects 0.000 description 5
- YCMAVBIZWABQFF-UHFFFAOYSA-N methyl 2,2-bis(4-bromophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(Br)C=CC=1C(C=1C=CC(Br)=CC=1)(C(=O)OC)C1=NC=CN1 YCMAVBIZWABQFF-UHFFFAOYSA-N 0.000 description 5
- WMHPZAWGENFCAS-UHFFFAOYSA-N methyl 2,2-bis(4-fluorophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(F)C=CC=1C(C=1C=CC(F)=CC=1)(C(=O)OC)C1=NC=CN1 WMHPZAWGENFCAS-UHFFFAOYSA-N 0.000 description 5
- XEZZSIVYLCTXPO-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N)C1=NC=CN1 XEZZSIVYLCTXPO-UHFFFAOYSA-N 0.000 description 4
- SEHVKRKEBXXVIB-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-n,n-dimethyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)C1=NC=CN1 SEHVKRKEBXXVIB-UHFFFAOYSA-N 0.000 description 4
- LCDMIMDUWFHYFQ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)NC)C1=NC=CN1 LCDMIMDUWFHYFQ-UHFFFAOYSA-N 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002543 antimycotic Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 4
- JMZZTLWBBMADOK-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-3-methyl-2-phenylbutanoate Chemical compound C=1C=CC=CC=1C(C(C)C)(C(=O)OCC)C1=NC=CN1 JMZZTLWBBMADOK-UHFFFAOYSA-N 0.000 description 4
- UQLDRUBJKYZDRV-UHFFFAOYSA-N ethyl 2-benzyl-2-(1h-imidazol-2-yl)-5-methylhexanoate Chemical compound N=1C=CNC=1C(CCC(C)C)(C(=O)OCC)CC1=CC=CC=C1 UQLDRUBJKYZDRV-UHFFFAOYSA-N 0.000 description 4
- BMEHATQTULZMSC-UHFFFAOYSA-N methyl 2,2-bis(4-chlorophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OC)C1=NC=CN1 BMEHATQTULZMSC-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- AVKUPUSZQPSBOD-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=NC=CN1 AVKUPUSZQPSBOD-UHFFFAOYSA-N 0.000 description 3
- RQCVNIVJMBXZRT-UHFFFAOYSA-N 2-methylpropyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC(C)C)C1=NC=CN1 RQCVNIVJMBXZRT-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- HJNNMNQHFFMNKH-UHFFFAOYSA-N benzyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound N=1C=CNC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 HJNNMNQHFFMNKH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- WTZLWKGRTJYAQR-UHFFFAOYSA-N decyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCCCCCCCCC)C1=NC=CN1 WTZLWKGRTJYAQR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- KQPURLPHEFAXQG-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-bis(4-methoxyphenyl)acetate Chemical compound C=1C=C(OC)C=CC=1C(C=1C=CC(OC)=CC=1)(C(=O)OC)C1=NC=CN1 KQPURLPHEFAXQG-UHFFFAOYSA-N 0.000 description 3
- RUBGLSZHUAFIBO-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 RUBGLSZHUAFIBO-UHFFFAOYSA-N 0.000 description 3
- DKQFBMYNBRIZCA-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)Cl)(C(=O)OC)C1=NC=CN1 DKQFBMYNBRIZCA-UHFFFAOYSA-N 0.000 description 3
- FPFJKVGMDIAFJI-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OC)C1=NC=CN1 FPFJKVGMDIAFJI-UHFFFAOYSA-N 0.000 description 3
- CJXUYNZKJHUHLE-UHFFFAOYSA-N octyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCCCCCCC)C1=NC=CN1 CJXUYNZKJHUHLE-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- FEAODWWVYMFEKL-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid methyl 2-(1H-imidazol-2-yl)-2,2-diphenylacetate Chemical compound OC(=O)C(O)C(O)C(O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 FEAODWWVYMFEKL-UHFFFAOYSA-N 0.000 description 2
- XQYVDDAXTYTKDB-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)N)C1=CC=CC=C1 XQYVDDAXTYTKDB-UHFFFAOYSA-N 0.000 description 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010007134 Candida infections Diseases 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 208000007163 Dermatomycoses Diseases 0.000 description 2
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 2
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- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 2
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- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 2
- 229960003942 amphotericin b Drugs 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 2
- 229960002867 griseofulvin Drugs 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 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
- MQGDDUZWULUNTO-UHFFFAOYSA-N methanesulfonic acid;methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound CS(O)(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 MQGDDUZWULUNTO-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- AHODWVIRUBFRBH-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 AHODWVIRUBFRBH-UHFFFAOYSA-N 0.000 description 2
- RBIZUCWGJMRQKS-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2-(4-methylphenyl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(C)=CC=1)(C(=O)OC)C1=NC=CN1 RBIZUCWGJMRQKS-UHFFFAOYSA-N 0.000 description 2
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- 244000000231 Sesamum indicum Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
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- 239000008272 agar Substances 0.000 description 1
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- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- CFGHWLWBJBVEJC-UHFFFAOYSA-N benzyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C(=O)OCC1=CC=CC=C1 CFGHWLWBJBVEJC-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HLPZYNMTXLNHJS-UHFFFAOYSA-N decyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCCCCCCCCC)C1=CC=CC=C1 HLPZYNMTXLNHJS-UHFFFAOYSA-N 0.000 description 1
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
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- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
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- XMDPMEQXOUQJOG-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2,2-bis(4-nitrophenyl)acetate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C=1C=CC(=CC=1)[N+]([O-])=O)(C(=O)OCC)C1=NC=CN1 XMDPMEQXOUQJOG-UHFFFAOYSA-N 0.000 description 1
- DRNQRIRVMLZTTF-UHFFFAOYSA-N ethyl 2-benzyl-2-(1h-imidazol-2-yl)-3-methylbutanoate Chemical compound N=1C=CNC=1C(C(=O)OCC)(C(C)C)CC1=CC=CC=C1 DRNQRIRVMLZTTF-UHFFFAOYSA-N 0.000 description 1
- MSBGLMWCKRSNHW-UHFFFAOYSA-N ethyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCC)C1=CC=CC=C1 MSBGLMWCKRSNHW-UHFFFAOYSA-N 0.000 description 1
- XJCMYFYVAGRANC-UHFFFAOYSA-N ethyl 2-chloro-3-methyl-2-phenylbutanoate Chemical compound CCOC(=O)C(Cl)(C(C)C)C1=CC=CC=C1 XJCMYFYVAGRANC-UHFFFAOYSA-N 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
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- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
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- 239000002054 inoculum Substances 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
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- KGYNKXFCPICMMI-UHFFFAOYSA-N methyl 2,2-bis(4-chlorophenyl)-2-hydroxyacetate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OC)C1=CC=C(Cl)C=C1 KGYNKXFCPICMMI-UHFFFAOYSA-N 0.000 description 1
- CLZGROCYYPFPAG-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-bis(4-methylphenyl)acetate Chemical compound C=1C=C(C)C=CC=1C(C=1C=CC(C)=CC=1)(C(=O)OC)C1=NC=CN1 CLZGROCYYPFPAG-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 description 1
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- RYQZDZLSAGLCHR-UHFFFAOYSA-N octyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCCCCCCC)C1=CC=CC=C1 RYQZDZLSAGLCHR-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ZKSUJTQPJAGLCM-UHFFFAOYSA-N propyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCC)C1=CC=CC=C1 ZKSUJTQPJAGLCM-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691925994 DE1925994C3 (de) | 1969-05-21 | Phenyl-imidazolyl-fettsäurederivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34516A0 IL34516A0 (en) | 1970-07-19 |
| IL34516A true IL34516A (en) | 1973-01-30 |
Family
ID=5734834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34516A IL34516A (en) | 1969-05-21 | 1970-05-13 | Phenyl-imidazolyl-alkanoic acid derivatives,their production and pharmaceutical compositions containing them |
Country Status (7)
| Country | Link |
|---|---|
| ES (1) | ES379870A1 (de) |
| IE (1) | IE34289B1 (de) |
| IL (1) | IL34516A (de) |
| NO (1) | NO128571B (de) |
| PH (1) | PH12184A (de) |
| PL (1) | PL80851B1 (de) |
| RO (1) | RO56292A (de) |
-
1970
- 1970-05-13 IL IL34516A patent/IL34516A/en unknown
- 1970-05-13 IE IE63070A patent/IE34289B1/xx unknown
- 1970-05-19 PH PH11460A patent/PH12184A/en unknown
- 1970-05-20 PL PL14074470A patent/PL80851B1/pl unknown
- 1970-05-20 NO NO93170A patent/NO128571B/no unknown
- 1970-05-20 RO RO6340570A patent/RO56292A/ro unknown
- 1970-05-21 ES ES379870A patent/ES379870A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL34516A0 (en) | 1970-07-19 |
| RO56292A (de) | 1974-08-01 |
| IE34289B1 (en) | 1975-04-02 |
| PH12184A (en) | 1978-11-21 |
| IE34289L (en) | 1970-11-21 |
| PL80851B1 (de) | 1975-08-30 |
| NO128571B (de) | 1973-12-10 |
| ES379870A1 (es) | 1972-09-16 |
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