IL93598A - [C-81C61) -3 (- Alkanesulfinyl- and sulfonyl-2-methoxy-methyl-propyl [-) trimethylammonioethyl (- phosphates, processes for their preparation and pharmaceutical preparations containing or - Google Patents
[C-81C61) -3 (- Alkanesulfinyl- and sulfonyl-2-methoxy-methyl-propyl [-) trimethylammonioethyl (- phosphates, processes for their preparation and pharmaceutical preparations containing orInfo
- Publication number
- IL93598A IL93598A IL9359890A IL9359890A IL93598A IL 93598 A IL93598 A IL 93598A IL 9359890 A IL9359890 A IL 9359890A IL 9359890 A IL9359890 A IL 9359890A IL 93598 A IL93598 A IL 93598A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- compound
- compounds
- trimethylammonioethyl
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 229910019142 PO4 Inorganic materials 0.000 title description 12
- 235000021317 phosphate Nutrition 0.000 title description 11
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- -1 sulphonyl-2-methoxymethylpropyl (2-trimethylammonioethyl)phosphates Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000005576 amination reaction Methods 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 229940006461 iodide ion Drugs 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 229940006460 bromide ion Drugs 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- ODEDPKNSRBCSDO-UHFFFAOYSA-N [2-(hexadecylsulfanylmethyl)-3-methoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCSCC(COC)COP([O-])(=O)OCC[N+](C)(C)C ODEDPKNSRBCSDO-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229950006905 ilmofosine Drugs 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 4
- SZQZSQFHECBPSV-UHFFFAOYSA-N CCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O Chemical compound CCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O SZQZSQFHECBPSV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- QXEQVPDRSQYMPV-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O Chemical compound CCCCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)(=O)=O QXEQVPDRSQYMPV-UHFFFAOYSA-N 0.000 description 2
- NAOCQLPMVZMQLW-UHFFFAOYSA-N CCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)=O Chemical compound CCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)=O NAOCQLPMVZMQLW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 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 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- ZURRKVIQUKNLHF-AYVLWNQUSA-N (4s)-4,7,7-trimethylbicyclo[2.2.1]heptane-3-carboxylic acid Chemical compound C1C[C@@]2(C)C(C(O)=O)CC1C2(C)C ZURRKVIQUKNLHF-AYVLWNQUSA-N 0.000 description 1
- YPGCWEMNNLXISK-ZETCQYMHSA-N (S)-hydratropic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC=C1 YPGCWEMNNLXISK-ZETCQYMHSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- DDGOBFWNNFNWDU-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)=O Chemical compound CCCCCCCCCCCCCCCCCCS(CC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC)=O DDGOBFWNNFNWDU-UHFFFAOYSA-N 0.000 description 1
- BUZGBYJEPIARLG-UHFFFAOYSA-N CCCCCCCCCCCCCCCCSCC(C(C)C(COP([O-])(O)=O)[N+](C)(C)C)OC Chemical compound CCCCCCCCCCCCCCCCSCC(C(C)C(COP([O-])(O)=O)[N+](C)(C)C)OC BUZGBYJEPIARLG-UHFFFAOYSA-N 0.000 description 1
- CPULMFMEGVQFEJ-UHFFFAOYSA-N CCCCCCCCCCCCCCCCSCC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC Chemical compound CCCCCCCCCCCCCCCCSCC(CC(COP([O-])(O)=O)[N+](C)(C)C)COC CPULMFMEGVQFEJ-UHFFFAOYSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- PPQNQXQZIWHJRB-UHFFFAOYSA-N Methylcholanthrene Chemical compound C1=CC=C2C3=CC4=CC=C(C)C(CC5)=C4C5=C3C=CC2=C1 PPQNQXQZIWHJRB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N alpha-phenylpropionic acid Natural products OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical group [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3906952A DE3906952A1 (de) | 1989-03-04 | 1989-03-04 | (3-(c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)6(pfeil abwaerts)-c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)8(pfeil abwaerts))alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl)-(2-trimethylammonio-ethyl) phosphate, verfahren zu deren herstellung diese verbindungen enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL93598A0 IL93598A0 (en) | 1990-12-23 |
| IL93598A true IL93598A (en) | 1994-06-24 |
Family
ID=6375519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9359890A IL93598A (en) | 1989-03-04 | 1990-03-01 | [C-81C61) -3 (- Alkanesulfinyl- and sulfonyl-2-methoxy-methyl-propyl [-) trimethylammonioethyl (- phosphates, processes for their preparation and pharmaceutical preparations containing or |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5543402A (ru) |
| EP (1) | EP0395849B1 (ru) |
| JP (1) | JPH0341027A (ru) |
| KR (1) | KR900014412A (ru) |
| AT (1) | ATE121409T1 (ru) |
| AU (1) | AU633304B2 (ru) |
| CA (1) | CA2011209A1 (ru) |
| DD (1) | DD292259A5 (ru) |
| DE (2) | DE3906952A1 (ru) |
| FI (1) | FI93122C (ru) |
| HU (1) | HU204057B (ru) |
| IE (1) | IE900743L (ru) |
| IL (1) | IL93598A (ru) |
| MX (1) | MX19722A (ru) |
| NO (1) | NO901008L (ru) |
| NZ (1) | NZ232692A (ru) |
| PT (1) | PT93324B (ru) |
| RU (1) | RU2035466C1 (ru) |
| ZA (1) | ZA901601B (ru) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3929217A1 (de) * | 1989-09-02 | 1991-03-07 | Boehringer Mannheim Gmbh | Verwendung von phospholipid-derivaten als antivirale arzneimittel und neue phospholipide |
| GB8928580D0 (en) * | 1989-12-19 | 1990-02-21 | Scras | 3-(n-methyl-n-alkylamino)-methoxymethyl-propanol phosphocholine derivatives |
| US6172050B1 (en) | 1992-07-11 | 2001-01-09 | Asta Medica Aktiengesellschaft | Phospholipid derivatives |
| DE4222910A1 (de) * | 1992-07-11 | 1994-01-13 | Asta Medica Ag | Neue Phospholipidderivate |
| WO1994002153A1 (en) * | 1992-07-22 | 1994-02-03 | Boehringer Mannheim Gmbh | Use of sulphur containing phospholipids for treating leishmaniasis |
| BR0112969A (pt) | 2000-08-04 | 2004-06-22 | Dmi Biosciences Inc | Método de utilização de dicetopiperazinas e composições contendo-as |
| KR100469556B1 (ko) * | 2001-11-17 | 2005-02-02 | 주식회사 건축사사무소다인그룹 | 도어 잠금장치 |
| NZ533094A (en) * | 2001-11-21 | 2006-01-27 | Heidelberg Pharma Gmbh | Phospholipid derivatives of nucleosides as antitumoral medicaments |
| EP1571970B1 (en) * | 2002-10-02 | 2011-08-17 | DMI Biosciences, Inc. | Diagnosis and monitoring of diseases |
| US7732403B2 (en) * | 2003-05-15 | 2010-06-08 | Dmi Biosciences, Inc. | Treatment of T-cell mediated diseases |
| US8217047B2 (en) * | 2008-05-27 | 2012-07-10 | Dmi Acquisition Corp. | Therapeutic methods and compounds |
| CA2810844C (en) | 2010-09-07 | 2017-03-21 | Dmi Acquisition Corp. | Diketopiperazine compositions for the treatment of metabolic syndrome and related conditions |
| PL2766029T3 (pl) | 2011-10-10 | 2020-08-24 | Ampio Pharmaceuticals, Inc. | Leczenie choroby zwyrodnieniowej stawów |
| WO2013055749A1 (en) | 2011-10-10 | 2013-04-18 | Ampio Pharmaceuticals, Inc. | Implantable medical devices with increased immune tolerance, and methods for making and implanting |
| JP6231484B2 (ja) | 2011-10-28 | 2017-11-15 | アンピオ ファーマシューティカルズ，インコーポレイテッド | 鼻炎の処置 |
| CN105101965B (zh) | 2013-03-15 | 2021-03-09 | 安皮奥制药股份有限公司 | 用于干细胞活动化、归巢、扩增和分化的组合物及其使用方法 |
| RU2736513C2 (ru) | 2014-08-18 | 2020-11-17 | Ампио Фармасьютикалз, Инк. | Лечение патологических состояний суставов |
| EP3310375A4 (en) | 2015-06-22 | 2019-02-20 | Ampio Pharmaceuticals, Inc. | USE OF LOW MOLECULAR WEIGHT HUMAN SERUM ALBUMIN FRACTIONS FOR TREATING DISEASES |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2009341C3 (de) * | 1970-02-27 | 1979-06-21 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | 3-Octadecyloxy-propanol-(l)-phosphorsäure-monocholinester und Verfahren zu dessen Herstellung |
| DE2619686C2 (de) * | 1976-05-04 | 1986-08-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Verwendung eines Lysolecithins zur Tumorbehandlung |
| DE2619715A1 (de) * | 1976-05-04 | 1977-11-24 | Max Planck Gesellschaft | Tumor-antigen und verfahren zu dessen herstellung |
| GB2046092B (en) * | 1979-03-05 | 1983-11-02 | Toyama Chemical Co Ltd | Pharmaceutical composition containing a lysophospholid and a phospholipid |
| US4444766A (en) * | 1980-10-21 | 1984-04-24 | Boehringer Mannheim Gmbh | Sulfur-containing phospholipid compounds and therapeutic compositions |
| DE3127503A1 (de) * | 1981-07-11 | 1983-02-17 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3304870A1 (de) * | 1983-02-12 | 1984-08-16 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
-
1989
- 1989-03-04 DE DE3906952A patent/DE3906952A1/de not_active Withdrawn
-
1990
- 1990-02-26 EP EP90103661A patent/EP0395849B1/de not_active Expired - Lifetime
- 1990-02-26 AT AT90103661T patent/ATE121409T1/de not_active IP Right Cessation
- 1990-02-26 DE DE59008915T patent/DE59008915D1/de not_active Expired - Fee Related
- 1990-02-27 NZ NZ232692A patent/NZ232692A/en unknown
- 1990-02-28 DD DD90338238A patent/DD292259A5/de not_active IP Right Cessation
- 1990-02-28 AU AU50596/90A patent/AU633304B2/en not_active Ceased
- 1990-03-01 IL IL9359890A patent/IL93598A/en not_active IP Right Cessation
- 1990-03-01 MX MX1972290A patent/MX19722A/es unknown
- 1990-03-02 PT PT93324A patent/PT93324B/pt not_active IP Right Cessation
- 1990-03-02 HU HU901280A patent/HU204057B/hu not_active IP Right Cessation
- 1990-03-02 IE IE900743A patent/IE900743L/xx unknown
- 1990-03-02 JP JP2051584A patent/JPH0341027A/ja active Pending
- 1990-03-02 RU SU904743486A patent/RU2035466C1/ru active
- 1990-03-02 FI FI901096A patent/FI93122C/fi not_active IP Right Cessation
- 1990-03-02 ZA ZA901601A patent/ZA901601B/xx unknown
- 1990-03-02 NO NO90901008A patent/NO901008L/no unknown
- 1990-03-05 KR KR1019900002942A patent/KR900014412A/ko not_active Application Discontinuation
- 1990-03-05 CA CA002011209A patent/CA2011209A1/en not_active Abandoned
-
1993
- 1993-07-23 US US08/095,478 patent/US5543402A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FI901096A0 (fi) | 1990-03-02 |
| ZA901601B (en) | 1990-12-28 |
| DD292259A5 (de) | 1991-07-25 |
| PT93324A (pt) | 1990-11-07 |
| DE59008915D1 (de) | 1995-05-24 |
| NO901008L (no) | 1990-09-05 |
| IE900743L (en) | 1990-09-04 |
| ATE121409T1 (de) | 1995-05-15 |
| NZ232692A (en) | 1992-06-25 |
| DE3906952A1 (de) | 1990-09-06 |
| FI93122C (fi) | 1995-02-27 |
| CA2011209A1 (en) | 1990-09-04 |
| US5543402A (en) | 1996-08-06 |
| NO901008D0 (no) | 1990-03-02 |
| MX19722A (es) | 1993-11-01 |
| JPH0341027A (ja) | 1991-02-21 |
| FI93122B (fi) | 1994-11-15 |
| PT93324B (pt) | 1996-02-29 |
| EP0395849B1 (de) | 1995-04-19 |
| EP0395849A1 (de) | 1990-11-07 |
| HU204057B (en) | 1991-11-28 |
| KR900014412A (ko) | 1990-10-23 |
| RU2035466C1 (ru) | 1995-05-20 |
| HUT53111A (en) | 1990-09-28 |
| IL93598A0 (en) | 1990-12-23 |
| AU5059690A (en) | 1990-09-06 |
| HU901280D0 (en) | 1990-05-28 |
| AU633304B2 (en) | 1993-01-28 |
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| KB | Patent renewed | ||
| RH | Patent void |