HU196172B - Process for producing new n-/2-hydroxy-alkyi/-amino-acids and derivatives and pharmaceutical compositions containing them as active agents - Google Patents
Process for producing new n-/2-hydroxy-alkyi/-amino-acids and derivatives and pharmaceutical compositions containing them as active agents Download PDFInfo
- Publication number
- HU196172B HU196172B HU854953A HU495385A HU196172B HU 196172 B HU196172 B HU 196172B HU 854953 A HU854953 A HU 854953A HU 495385 A HU495385 A HU 495385A HU 196172 B HU196172 B HU 196172B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- dimethyl
- hydrogen
- ammonio
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 239000013543 active substance Substances 0.000 title description 2
- 229940093740 amino acid and derivative Drugs 0.000 title 1
- -1 alkali metal salt Chemical class 0.000 claims description 139
- 150000001875 compounds Chemical class 0.000 claims description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 10
- 229940100198 alkylating agent Drugs 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 229960003237 betaine Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000012430 organic reaction media Substances 0.000 claims description 2
- 150000007519 polyprotic acids Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003862 amino acid derivatives Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 86
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 description 50
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- 150000008064 anhydrides Chemical class 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 11
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- GRKUXCWELVWVMZ-UHFFFAOYSA-N amino acetate Chemical compound CC(=O)ON GRKUXCWELVWVMZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- URWUYFIUUYGIBY-UHFFFAOYSA-N 1-(dimethylamino)octadecan-2-yl acetate Chemical compound CCCCCCCCCCCCCCCCC(CN(C)C)OC(C)=O URWUYFIUUYGIBY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- TWOYDRFPPVTQOY-UHFFFAOYSA-N (4-ethoxy-4-oxobutyl)-(2-hydroxyoctadecyl)-methylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCC(O)C[NH+](C)CCCC(=O)OCC TWOYDRFPPVTQOY-UHFFFAOYSA-N 0.000 description 2
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical class CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 2
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FBWMYSQUTZRHAT-HZJYTTRNSA-N (9z,12z)-octadeca-9,12-dienoyl chloride Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O FBWMYSQUTZRHAT-HZJYTTRNSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- JSDXLVNTRGRJRY-UHFFFAOYSA-N 1-(dimethylamino)octadecan-2-ol Chemical compound CCCCCCCCCCCCCCCCC(O)CN(C)C JSDXLVNTRGRJRY-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- XFEWMFDVBLLXFE-UHFFFAOYSA-N 1-isocyanatodecane Chemical compound CCCCCCCCCCN=C=O XFEWMFDVBLLXFE-UHFFFAOYSA-N 0.000 description 1
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
- XIFGNGCAPGVNJX-UHFFFAOYSA-N 1-isocyanatoheptadecane Chemical compound CCCCCCCCCCCCCCCCCN=C=O XIFGNGCAPGVNJX-UHFFFAOYSA-N 0.000 description 1
- RFXBSYPBSRSQDU-UHFFFAOYSA-N 1-isocyanatoheptane Chemical compound CCCCCCCN=C=O RFXBSYPBSRSQDU-UHFFFAOYSA-N 0.000 description 1
- GFLXBRUGMACJLQ-UHFFFAOYSA-N 1-isocyanatohexadecane Chemical compound CCCCCCCCCCCCCCCCN=C=O GFLXBRUGMACJLQ-UHFFFAOYSA-N 0.000 description 1
- DLGUAUVHTOCKTB-UHFFFAOYSA-N 1-isocyanatononane Chemical compound CCCCCCCCCN=C=O DLGUAUVHTOCKTB-UHFFFAOYSA-N 0.000 description 1
- HULTVDSPXGVYBQ-UHFFFAOYSA-N 1-isocyanatopentadecane Chemical compound CCCCCCCCCCCCCCCN=C=O HULTVDSPXGVYBQ-UHFFFAOYSA-N 0.000 description 1
- VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical compound CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- CSMJMAQKBKGDQX-UHFFFAOYSA-N 1-isocyanatotetradecane Chemical compound CCCCCCCCCCCCCCN=C=O CSMJMAQKBKGDQX-UHFFFAOYSA-N 0.000 description 1
- BAZBBHGFCBVAQU-UHFFFAOYSA-N 1-isocyanatotridecane Chemical compound CCCCCCCCCCCCCN=C=O BAZBBHGFCBVAQU-UHFFFAOYSA-N 0.000 description 1
- JXAYHHMVMJVFPQ-UHFFFAOYSA-N 1-isocyanatoundecane Chemical compound CCCCCCCCCCCN=C=O JXAYHHMVMJVFPQ-UHFFFAOYSA-N 0.000 description 1
- KKASGUHLXWAKEZ-UHFFFAOYSA-N 1-isothiocyanatopropane Chemical compound CCCN=C=S KKASGUHLXWAKEZ-UHFFFAOYSA-N 0.000 description 1
- VTDADTAVOJGNSQ-UHFFFAOYSA-N 10-bromo-2,2-dimethyldecanoic acid Chemical compound BrCCCCCCCCC(C(O)=O)(C)C VTDADTAVOJGNSQ-UHFFFAOYSA-N 0.000 description 1
- PGVRSPIEZYGOAD-UHFFFAOYSA-N 10-bromodecanoic acid Chemical compound OC(=O)CCCCCCCCCBr PGVRSPIEZYGOAD-UHFFFAOYSA-N 0.000 description 1
- RYQHADMKPSNIEC-UHFFFAOYSA-N 10-chloro-2,2-dimethyldecanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCCCCl RYQHADMKPSNIEC-UHFFFAOYSA-N 0.000 description 1
- FQQUDTHUGUIYAQ-UHFFFAOYSA-N 10-chloro-2-methyldecanoic acid Chemical compound OC(=O)C(C)CCCCCCCCCl FQQUDTHUGUIYAQ-UHFFFAOYSA-N 0.000 description 1
- FEXSVCTUDASSOQ-UHFFFAOYSA-N 10-chlorodecanoic acid Chemical compound OC(=O)CCCCCCCCCCl FEXSVCTUDASSOQ-UHFFFAOYSA-N 0.000 description 1
- YAPMKYQTZFGOPY-UHFFFAOYSA-N 11-bromo-2,2-dimethylundecanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCCCCBr YAPMKYQTZFGOPY-UHFFFAOYSA-N 0.000 description 1
- YHYSFJBAAMODHY-UHFFFAOYSA-N 11-bromododecanoic acid Chemical compound CC(Br)CCCCCCCCCC(O)=O YHYSFJBAAMODHY-UHFFFAOYSA-N 0.000 description 1
- GVZXFVFTBUYBJD-UHFFFAOYSA-N 11-chloroundecanoic acid Chemical compound OC(=O)CCCCCCCCCCCl GVZXFVFTBUYBJD-UHFFFAOYSA-N 0.000 description 1
- XNMSFLKPBJLACJ-UHFFFAOYSA-N 12-bromo-2-methyldodecanoic acid Chemical compound OC(=O)C(C)CCCCCCCCCCBr XNMSFLKPBJLACJ-UHFFFAOYSA-N 0.000 description 1
- YYKBWYBUCFHYPR-UHFFFAOYSA-N 12-bromododecanoic acid Chemical compound OC(=O)CCCCCCCCCCCBr YYKBWYBUCFHYPR-UHFFFAOYSA-N 0.000 description 1
- XMGNQMNFUQYMLV-UHFFFAOYSA-N 12-chloro-2,2-dimethyldodecanoic acid Chemical compound ClCCCCCCCCCCC(C(=O)O)(C)C XMGNQMNFUQYMLV-UHFFFAOYSA-N 0.000 description 1
- FESMIWFYLBYKSD-UHFFFAOYSA-N 12-chloro-2-methyldodecanoic acid Chemical compound OC(=O)C(C)CCCCCCCCCCCl FESMIWFYLBYKSD-UHFFFAOYSA-N 0.000 description 1
- CSQLFBKZQRLUFP-UHFFFAOYSA-N 12-chloro-dodecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCl CSQLFBKZQRLUFP-UHFFFAOYSA-N 0.000 description 1
- RHOZYFCZKHHXOR-UHFFFAOYSA-N 2-[2-(ethylcarbamoyloxy)icosyl-dimethylazaniumyl]acetate Chemical compound CCCCCCCCCCCCCCCCCCC(C[N+](C)(C)CC([O-])=O)OC(=O)NCC RHOZYFCZKHHXOR-UHFFFAOYSA-N 0.000 description 1
- GLVFBHBVOIWTAG-UHFFFAOYSA-N 2-acetyloxyoctadecyl-(3-carboxypropyl)-methylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCC(OC(C)=O)C[NH+](C)CCCC(O)=O GLVFBHBVOIWTAG-UHFFFAOYSA-N 0.000 description 1
- WAKFRZBXTKUFIW-UHFFFAOYSA-N 2-bromo-2-phenylacetic acid Chemical compound OC(=O)C(Br)C1=CC=CC=C1 WAKFRZBXTKUFIW-UHFFFAOYSA-N 0.000 description 1
- FNIBRUOFKCBDGB-UHFFFAOYSA-N 2-bromo-2-phenylpropanoic acid Chemical compound OC(=O)C(Br)(C)C1=CC=CC=C1 FNIBRUOFKCBDGB-UHFFFAOYSA-N 0.000 description 1
- GQZXYZIKUQUVKE-UHFFFAOYSA-N 2-bromo-3-methylpentanoic acid Chemical compound CCC(C)C(Br)C(O)=O GQZXYZIKUQUVKE-UHFFFAOYSA-N 0.000 description 1
- WDRSCFNERFONKU-UHFFFAOYSA-N 2-bromo-3-phenylpropanoic acid Chemical compound OC(=O)C(Br)CC1=CC=CC=C1 WDRSCFNERFONKU-UHFFFAOYSA-N 0.000 description 1
- NNFDHJQLIFECSR-UHFFFAOYSA-N 2-bromo-4-methylpentanoic acid Chemical compound CC(C)CC(Br)C(O)=O NNFDHJQLIFECSR-UHFFFAOYSA-N 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 1
- HZTPKMIMXLTOSK-UHFFFAOYSA-N 2-bromohexanoic acid Chemical compound CCCCC(Br)C(O)=O HZTPKMIMXLTOSK-UHFFFAOYSA-N 0.000 description 1
- SALJMWGDEHMNSS-UHFFFAOYSA-N 2-bromopentanethioic S-acid Chemical compound BrC(C(=S)O)CCC SALJMWGDEHMNSS-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
- QYDWVWHHWQRBEA-UHFFFAOYSA-N 2-chloro-2-phenylpropanoic acid Chemical compound OC(=O)C(Cl)(C)C1=CC=CC=C1 QYDWVWHHWQRBEA-UHFFFAOYSA-N 0.000 description 1
- DDTJFSPKEIAZAM-UHFFFAOYSA-N 2-chloro-3-methylbutanoic acid Chemical compound CC(C)C(Cl)C(O)=O DDTJFSPKEIAZAM-UHFFFAOYSA-N 0.000 description 1
- QMYSXXQDOZTXAE-UHFFFAOYSA-N 2-chloro-3-methylpentanoic acid Chemical compound CCC(C)C(Cl)C(O)=O QMYSXXQDOZTXAE-UHFFFAOYSA-N 0.000 description 1
- LIDRHDRWTSPELB-UHFFFAOYSA-N 2-chloro-3-phenylpropanoic acid Chemical compound OC(=O)C(Cl)CC1=CC=CC=C1 LIDRHDRWTSPELB-UHFFFAOYSA-N 0.000 description 1
- CBQBIPRPIHIKPW-UHFFFAOYSA-N 2-chloro-4-methylpentanoic acid Chemical compound CC(C)CC(Cl)C(O)=O CBQBIPRPIHIKPW-UHFFFAOYSA-N 0.000 description 1
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
- OMPRMWFZHLNRQJ-UHFFFAOYSA-N 2-chlorohexanoic acid Chemical compound CCCCC(Cl)C(O)=O OMPRMWFZHLNRQJ-UHFFFAOYSA-N 0.000 description 1
- UERWBAKOACKYSH-UHFFFAOYSA-N 2-chloropentanethioic s-acid Chemical compound CCCC(Cl)C(S)=O UERWBAKOACKYSH-UHFFFAOYSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- ADGCVKXNAIBOQJ-UHFFFAOYSA-N 2-decyloxirene Chemical compound CCCCCCCCCCC1=CO1 ADGCVKXNAIBOQJ-UHFFFAOYSA-N 0.000 description 1
- IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 1
- QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
- MDJCCLDIFSDFTH-UHFFFAOYSA-N 2-icosyloxirane Chemical compound CCCCCCCCCCCCCCCCCCCCC1CO1 MDJCCLDIFSDFTH-UHFFFAOYSA-N 0.000 description 1
- XSNXNMMWBCZUSS-UHFFFAOYSA-N 2-pentadecyloxirane Chemical compound CCCCCCCCCCCCCCCC1CO1 XSNXNMMWBCZUSS-UHFFFAOYSA-N 0.000 description 1
- QMIBIXKZPBEGTE-UHFFFAOYSA-N 2-tridecyloxirane Chemical compound CCCCCCCCCCCCCC1CO1 QMIBIXKZPBEGTE-UHFFFAOYSA-N 0.000 description 1
- KAOCOYOXDKAJCL-UHFFFAOYSA-N 3-[2-hydroxydocosyl(dimethyl)azaniumyl]propanoate Chemical compound CCCCCCCCCCCCCCCCCCCCC(O)C[N+](C)(C)CCC([O-])=O KAOCOYOXDKAJCL-UHFFFAOYSA-N 0.000 description 1
- WYYCHYJIBKOZJY-UHFFFAOYSA-N 3-[dimethyl(2-propanoyloxyicosyl)azaniumyl]propanoate Chemical compound CCCCCCCCCCCCCCCCCCC(C[N+](C)(C)CCC(=O)[O-])OC(=O)CC WYYCHYJIBKOZJY-UHFFFAOYSA-N 0.000 description 1
- FYHBVTYDATZUEE-UHFFFAOYSA-N 3-bromo-2,2-dimethylpropanoic acid Chemical compound BrCC(C)(C)C(O)=O FYHBVTYDATZUEE-UHFFFAOYSA-N 0.000 description 1
- BUPXDXGYFXDDAA-UHFFFAOYSA-N 3-bromo-2-methylpropanoic acid Chemical compound BrCC(C)C(O)=O BUPXDXGYFXDDAA-UHFFFAOYSA-N 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
- AWSSTZZQBPIWKZ-UHFFFAOYSA-N 3-chloro-2-methylpropanoic acid Chemical compound ClCC(C)C(O)=O AWSSTZZQBPIWKZ-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- GQVYBECSNBLQJV-VAWYXSNFSA-N 3-n-decyl acrylic acid Chemical compound CCCCCCCCCC\C=C\C(O)=O GQVYBECSNBLQJV-VAWYXSNFSA-N 0.000 description 1
- IYHCFKZRBPCJQL-UHFFFAOYSA-N 4-bromo-2,2-dimethylbutanoic acid Chemical compound OC(=O)C(C)(C)CCBr IYHCFKZRBPCJQL-UHFFFAOYSA-N 0.000 description 1
- AFUWKGZPMVUKIN-UHFFFAOYSA-N 4-bromo-2-methylbutanoic acid Chemical compound OC(=O)C(C)CCBr AFUWKGZPMVUKIN-UHFFFAOYSA-N 0.000 description 1
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 description 1
- YKFFACBRWIUUOD-UHFFFAOYSA-N 4-chloro-2,2-dimethylbutanoic acid Chemical compound OC(=O)C(C)(C)CCCl YKFFACBRWIUUOD-UHFFFAOYSA-N 0.000 description 1
- CSVRBZABWINVSH-UHFFFAOYSA-N 4-chloro-2-ethylbutanoic acid Chemical compound CCC(C(O)=O)CCCl CSVRBZABWINVSH-UHFFFAOYSA-N 0.000 description 1
- JACOJLDLXBNEMP-UHFFFAOYSA-N 4-chloro-2-methylbutanoic acid Chemical compound OC(=O)C(C)CCCl JACOJLDLXBNEMP-UHFFFAOYSA-N 0.000 description 1
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 description 1
- LCFXALBDNIVOCD-UHFFFAOYSA-N 5-[2-hydroxyoctadecyl(dimethyl)azaniumyl]pentanoate Chemical compound C[N+](CC(CCCCCCCCCCCCCCCC)O)(C)CCCCC(=O)[O-] LCFXALBDNIVOCD-UHFFFAOYSA-N 0.000 description 1
- KZAMQAAMEOXHBU-UHFFFAOYSA-N 5-bromo-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCBr KZAMQAAMEOXHBU-UHFFFAOYSA-N 0.000 description 1
- QAZIIRDSXYZNAI-UHFFFAOYSA-N 5-chloro-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCCl QAZIIRDSXYZNAI-UHFFFAOYSA-N 0.000 description 1
- XBLBTILEUDNPQJ-UHFFFAOYSA-N 6-bromo-2,2-dimethylhexanoic acid Chemical compound OC(=O)C(C)(C)CCCCBr XBLBTILEUDNPQJ-UHFFFAOYSA-N 0.000 description 1
- IPKFFYBHMDNBSC-UHFFFAOYSA-N 6-bromo-2-methylhexanoic acid Chemical compound OC(=O)C(C)CCCCBr IPKFFYBHMDNBSC-UHFFFAOYSA-N 0.000 description 1
- NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 description 1
- WHZYFSOMRWBOBI-UHFFFAOYSA-N 6-chloro-2,2-dimethylhexanoic acid Chemical compound OC(=O)C(C)(C)CCCCCl WHZYFSOMRWBOBI-UHFFFAOYSA-N 0.000 description 1
- PYDJXNLBAMMUES-UHFFFAOYSA-N 6-chloro-2-methylhexanoic acid Chemical compound OC(=O)C(C)CCCCCl PYDJXNLBAMMUES-UHFFFAOYSA-N 0.000 description 1
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 description 1
- WTCJJEJMYYASNT-UHFFFAOYSA-N 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F WTCJJEJMYYASNT-UHFFFAOYSA-N 0.000 description 1
- CHEOMMCWENGKKI-UHFFFAOYSA-N 7-chloro-2-methylheptanoic acid Chemical compound ClCCCCCC(C(=O)O)C CHEOMMCWENGKKI-UHFFFAOYSA-N 0.000 description 1
- ZRJDOTOHSGMNJK-UHFFFAOYSA-N 8-bromo-2,2-dimethyloctanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCBr ZRJDOTOHSGMNJK-UHFFFAOYSA-N 0.000 description 1
- GHBKZAJXCXDEAK-UHFFFAOYSA-N 8-bromo-2-methyloctanoic acid Chemical compound OC(=O)C(C)CCCCCCBr GHBKZAJXCXDEAK-UHFFFAOYSA-N 0.000 description 1
- BKJFDZSBZWHRNH-UHFFFAOYSA-N 8-bromooctanoic acid Chemical compound OC(=O)CCCCCCCBr BKJFDZSBZWHRNH-UHFFFAOYSA-N 0.000 description 1
- SJHCDMKHMIJAIW-UHFFFAOYSA-N 8-chloro-2,2-dimethyloctanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCCl SJHCDMKHMIJAIW-UHFFFAOYSA-N 0.000 description 1
- BGYPPYWDTVHCLI-UHFFFAOYSA-N 8-chloro-2-methyloctanoic acid Chemical compound OC(=O)C(C)CCCCCCCl BGYPPYWDTVHCLI-UHFFFAOYSA-N 0.000 description 1
- SCTRLHIAVHHIEJ-UHFFFAOYSA-N 8-chlorooctanoic acid Chemical compound OC(=O)CCCCCCCCl SCTRLHIAVHHIEJ-UHFFFAOYSA-N 0.000 description 1
- AYNBRHSYIBNQAI-UHFFFAOYSA-N 9-bromo-2,2-dimethylnonanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCCBr AYNBRHSYIBNQAI-UHFFFAOYSA-N 0.000 description 1
- XEGRKZRPTBNSMN-UHFFFAOYSA-N 9-bromononanoic acid Chemical compound OC(=O)CCCCCCCCBr XEGRKZRPTBNSMN-UHFFFAOYSA-N 0.000 description 1
- ACNWRUZNRFEPLZ-UHFFFAOYSA-N 9-chloro-2,2-dimethylnonanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCCCl ACNWRUZNRFEPLZ-UHFFFAOYSA-N 0.000 description 1
- UTDAPYREGQHAOM-UHFFFAOYSA-N 9-chloro-2-methylnonanoic acid Chemical compound OC(=O)C(C)CCCCCCCCl UTDAPYREGQHAOM-UHFFFAOYSA-N 0.000 description 1
- DFJLDESPZKERQH-UHFFFAOYSA-N 9-chlorononanoic acid Chemical compound OC(=O)CCCCCCCCCl DFJLDESPZKERQH-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- YYKGRDLZJGVEQW-WXXKFALUSA-N C(\C=C\C(=O)[O-])(=O)[O-].C(C)OC(=O)C[NH+](CC(CCCCCCCCCCCCCCCC)OC)C.C(C)OC(=O)C[NH+](C)CC(CCCCCCCCCCCCCCCC)OC Chemical compound C(\C=C\C(=O)[O-])(=O)[O-].C(C)OC(=O)C[NH+](CC(CCCCCCCCCCCCCCCC)OC)C.C(C)OC(=O)C[NH+](C)CC(CCCCCCCCCCCCCCCC)OC YYKGRDLZJGVEQW-WXXKFALUSA-N 0.000 description 1
- LNFDPNIGZPQUCT-UHFFFAOYSA-N CC(C)(CCCCCCCCCCBr)C(=O)O Chemical compound CC(C)(CCCCCCCCCCBr)C(=O)O LNFDPNIGZPQUCT-UHFFFAOYSA-N 0.000 description 1
- XZOLAUSLTBKEJE-UHFFFAOYSA-N CC(C)(CCCCCCCCCCl)C(=O)O Chemical compound CC(C)(CCCCCCCCCCl)C(=O)O XZOLAUSLTBKEJE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 208000007093 Leukemia L1210 Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
- MRJCCJRBMBZXDY-UHFFFAOYSA-N OC(=O)C(C)CCCCCCCCCBr Chemical compound OC(=O)C(C)CCCCCCCCCBr MRJCCJRBMBZXDY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process 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
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- LXKYGQCVPGFMOE-UHFFFAOYSA-N butanoic acid carbonochloridic acid Chemical compound C(CCC)(=O)O.ClC(=O)O LXKYGQCVPGFMOE-UHFFFAOYSA-N 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- AZZCHVHSWUYCQA-UHFFFAOYSA-N decyl carbonochloridate Chemical compound CCCCCCCCCCOC(Cl)=O AZZCHVHSWUYCQA-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- AFPOMDNRTZLRMD-UHFFFAOYSA-N dodecyl carbonochloridate Chemical compound CCCCCCCCCCCCOC(Cl)=O AFPOMDNRTZLRMD-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- ICDQUAGMQCUEMY-UHFFFAOYSA-N heptadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCC(Cl)=O ICDQUAGMQCUEMY-UHFFFAOYSA-N 0.000 description 1
- SATRZZYUXUGZIE-UHFFFAOYSA-N heptyl carbonochloridate Chemical compound CCCCCCCOC(Cl)=O SATRZZYUXUGZIE-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- HOQUWXSARQBQCW-UHFFFAOYSA-N hexadecyl carbonochloridate Chemical compound CCCCCCCCCCCCCCCCOC(Cl)=O HOQUWXSARQBQCW-UHFFFAOYSA-N 0.000 description 1
- KIWBRXCOTCXSSZ-UHFFFAOYSA-N hexyl carbonochloridate Chemical compound CCCCCCOC(Cl)=O KIWBRXCOTCXSSZ-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical group IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- XZVYDRLPXWFRIS-UHFFFAOYSA-N n-ethyl-n-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- VLSTXUUYLIALPB-UHFFFAOYSA-N n-propan-2-ylpropan-1-amine Chemical compound CCCNC(C)C VLSTXUUYLIALPB-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- BASNZTUXPUAQLZ-UHFFFAOYSA-N nonadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCC(Cl)=O BASNZTUXPUAQLZ-UHFFFAOYSA-N 0.000 description 1
- VKOFPDUSOTWTPX-UHFFFAOYSA-N nonyl carbonochloridate Chemical compound CCCCCCCCCOC(Cl)=O VKOFPDUSOTWTPX-UHFFFAOYSA-N 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical class CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- PQZWQGNQOVDTRF-UHFFFAOYSA-N pentadecanoyl chloride Chemical compound CCCCCCCCCCCCCCC(Cl)=O PQZWQGNQOVDTRF-UHFFFAOYSA-N 0.000 description 1
- YBMUKVZQKMYTSX-UHFFFAOYSA-N pentadecyl carbonochloridate Chemical compound CCCCCCCCCCCCCCCOC(Cl)=O YBMUKVZQKMYTSX-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000126 substance 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
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 1
- KQHBSKZGPQPRIT-UHFFFAOYSA-N tetradecyl carbonochloridate Chemical compound CCCCCCCCCCCCCCOC(Cl)=O KQHBSKZGPQPRIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical class CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- YQCPEOLHTKYQSR-UHFFFAOYSA-N undecyl carbonochloridate Chemical compound CCCCCCCCCCCOC(Cl)=O YQCPEOLHTKYQSR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3447295 | 1984-12-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT39415A HUT39415A (en) | 1986-09-29 |
| HU196172B true HU196172B (en) | 1988-10-28 |
Family
ID=6253822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU854953A HU196172B (en) | 1984-12-24 | 1985-12-23 | Process for producing new n-/2-hydroxy-alkyi/-amino-acids and derivatives and pharmaceutical compositions containing them as active agents |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0186083A3 (en, 2012) |
| JP (1) | JPS61191654A (en, 2012) |
| DD (1) | DD258005A5 (en, 2012) |
| DK (1) | DK603085A (en, 2012) |
| ES (1) | ES8705847A1 (en, 2012) |
| FI (1) | FI855149A7 (en, 2012) |
| GR (1) | GR853136B (en, 2012) |
| HU (1) | HU196172B (en, 2012) |
| PT (1) | PT81758B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4829536B2 (ja) * | 2004-06-08 | 2011-12-07 | 川研ファインケミカル株式会社 | ベタイン型化合物およびそれを含有する洗浄剤組成物 |
| WO2011016033A1 (en) * | 2009-08-04 | 2011-02-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Amino-alcohol analogues and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965014A (en) * | 1972-12-07 | 1976-06-22 | Colgate-Palmolive Company | Anionic fabric conditioners |
-
1985
- 1985-12-14 EP EP85115997A patent/EP0186083A3/de not_active Withdrawn
- 1985-12-23 GR GR853136A patent/GR853136B/el unknown
- 1985-12-23 PT PT81758A patent/PT81758B/pt unknown
- 1985-12-23 DK DK603085A patent/DK603085A/da not_active Application Discontinuation
- 1985-12-23 FI FI855149A patent/FI855149A7/fi not_active IP Right Cessation
- 1985-12-23 DD DD85285098A patent/DD258005A5/de unknown
- 1985-12-23 ES ES550337A patent/ES8705847A1/es not_active Expired
- 1985-12-23 HU HU854953A patent/HU196172B/hu unknown
- 1985-12-24 JP JP60289528A patent/JPS61191654A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK603085D0 (da) | 1985-12-23 |
| ES8705847A1 (es) | 1987-05-16 |
| EP0186083A3 (de) | 1987-08-26 |
| HUT39415A (en) | 1986-09-29 |
| JPS61191654A (ja) | 1986-08-26 |
| EP0186083A2 (de) | 1986-07-02 |
| PT81758B (de) | 1987-04-30 |
| DK603085A (da) | 1986-06-25 |
| PT81758A (de) | 1986-01-02 |
| DD258005A5 (de) | 1988-07-06 |
| FI855149A7 (fi) | 1986-06-25 |
| GR853136B (en, 2012) | 1986-04-24 |
| ES550337A0 (es) | 1987-05-16 |
| FI855149A0 (fi) | 1985-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI87766B (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva n-(2'-aminofenyl)bensamidderivat | |
| JP2801401B2 (ja) | 新規な製法 | |
| US5434304A (en) | Process for preparing formoterol and related compounds | |
| DK159264B (da) | Analogifremgangsmaade til fremstilling af d-(threo)-1-aryl-2-acylamido-3-fluor-1-propanolforbindelser | |
| DE1695556B2 (de) | 3Alkyl-l,2,3,4,4a,9-hexahydropyrazino [1,2-f] morphanthridinderivate | |
| DE69330639T2 (de) | Methotrexat-derivate | |
| CA2104776C (en) | Thalidomide derivatives, method of manufacture and use thereof in medicaments | |
| CH521355A (de) | Verfahren zur Herstellung von aromatischen Äthern | |
| NL8204126A (nl) | Werkwijze voor het bereiden van een farmaceutisch preparaat met locaal-anesthetische werking dat een dialylamino-2',6'acetoxylidide en/of een farmaceutisch aanvaardbaar zout daarvan bevat, alsmede de onder toepassing van deze werkwijze verkregen gevormde farmaceutische preparaten en werkwijze voor het bereiden van dialkylamino-2',6'acetoxylididen en de farmaceutisch aanvaardbare zouten daarvan. | |
| EP0101574B1 (de) | 2-Substituierte 1-Aminoalkyl-1,2,3,4-tetrahydro-beta-carboline, ihre Herstellung und Verwendung als Arzneimittel | |
| EP0096870B1 (en) | Ester of metronidazole with n,n-dimethylglycine and acid addition salt thereof | |
| DE69401177T2 (de) | 1-Aryloxy-3-alkylamino-2 propanol nitrat Ester, ihre Anwendung und korrespondierende pharmazeutische Zusammensetzungen | |
| HU196172B (en) | Process for producing new n-/2-hydroxy-alkyi/-amino-acids and derivatives and pharmaceutical compositions containing them as active agents | |
| US20060135785A1 (en) | Alpha-phenyl acetanilide derivatives having an acat inhibiting activity and the therapeutic application thereof | |
| US4318915A (en) | Substituted guandines and methods of preparation thereof | |
| DE69217087T2 (de) | Indolderivat mit verlängerter immunostimmulierender wirkung und pharmazeutische zusammensetzungen daraus | |
| EP0358571A1 (fr) | Thioformamidines, leur préparation et leur application en tant que médicaments | |
| US3655752A (en) | Isomers of 2 4 6-trihalo-n n n' n'-tetraalkylisophthalamides | |
| JPH02250896A (ja) | ３―ピログルタミル―チアゾリジン―４―カルボン酸誘導体 | |
| SK279646B6 (sk) | Jódované benzénové deriváty, spôsob ich výroby a k | |
| FI80440C (fi) | Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara afidkolanderivat. | |
| EP0345163A1 (fr) | Nouveau composé triiodobenzénique non ionique iodé, son procédé de préparation et produit de contraste le contenant | |
| EP4293032A1 (en) | Benzazepine compounds, preparation method therefor and pharmaceutical use thereof | |
| KR19990073143A (ko) | 할로에틸-2-[(2,6-디클로로페닐)아미노]페닐아세톡시아세테이트유도체와이를중간체로사용하는아세클로페낙의제조방법 | |
| AT389703B (de) | Verfahren zur herstellung von neuen 3-amino-substituierten steroidderivaten und von deren salzen |