SE501393C2 - Glycerolderivat, ett framställningsförfarande för desamma samt terapeutiska kompositioner innehållande dem - Google Patents
Glycerolderivat, ett framställningsförfarande för desamma samt terapeutiska kompositioner innehållande demInfo
- Publication number
- SE501393C2 SE501393C2 SE9003973A SE9003973A SE501393C2 SE 501393 C2 SE501393 C2 SE 501393C2 SE 9003973 A SE9003973 A SE 9003973A SE 9003973 A SE9003973 A SE 9003973A SE 501393 C2 SE501393 C2 SE 501393C2
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- methoxy
- tlc
- compounds
- iib
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000002314 glycerols Chemical class 0.000 title claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 125000005131 dialkylammonium group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- OHTPZWRWJRNDGC-UHFFFAOYSA-N [1-hydroxy-3-[methyl(octadecyl)amino]propan-2-yl] n-methylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(CO)OC(=O)NC OHTPZWRWJRNDGC-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000003480 eluent Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- -1 N-Methyl-octadecylamino Chemical group 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UMVHFZWXXHZDMR-UHFFFAOYSA-N 3-methoxy-2-[methyl(octadecyl)amino]propan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCN(C)C(CO)COC UMVHFZWXXHZDMR-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- DHILWXDGDAHFPS-UHFFFAOYSA-N 1-methoxy-3-[methyl(octadecyl)amino]propan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(O)COC DHILWXDGDAHFPS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XWFZEOQPMROJSH-UHFFFAOYSA-N 2-methoxy-3-phenylmethoxypropan-1-ol Chemical compound COC(CO)COCC1=CC=CC=C1 XWFZEOQPMROJSH-UHFFFAOYSA-N 0.000 description 4
- VGRWLSCCYCJYST-UHFFFAOYSA-N 5-methoxy-2-phenyl-1,3-dioxane Chemical compound O1CC(OC)COC1C1=CC=CC=C1 VGRWLSCCYCJYST-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052754 neon Inorganic materials 0.000 description 4
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IYNSPGKFJQIGAI-UHFFFAOYSA-N (3-methoxy-2-phenylmethoxypropyl) methanesulfonate Chemical compound CS(=O)(=O)OCC(COC)OCC1=CC=CC=C1 IYNSPGKFJQIGAI-UHFFFAOYSA-N 0.000 description 3
- OPGDPALMUNOHNY-UHFFFAOYSA-N 3-methoxy-2-phenylmethoxypropan-1-ol Chemical compound COCC(CO)OCC1=CC=CC=C1 OPGDPALMUNOHNY-UHFFFAOYSA-N 0.000 description 3
- XRCNTWXLLFNXRS-UHFFFAOYSA-N 4-(methoxymethyl)-2-phenyl-1,3-dioxolane Chemical compound O1C(COC)COC1C1=CC=CC=C1 XRCNTWXLLFNXRS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 3
- MAVZHVYMTQPFSW-UHFFFAOYSA-N 1-[methyl(octadecyl)amino]-3-trityloxypropan-2-ol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC(O)CN(C)CCCCCCCCCCCCCCCCCC)C1=CC=CC=C1 MAVZHVYMTQPFSW-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SBMUNILHNJLMBF-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound ClP1(=O)OCCO1 SBMUNILHNJLMBF-UHFFFAOYSA-N 0.000 description 2
- CJLGREYPKZVCDD-UHFFFAOYSA-N 2-ethoxy-3-[methyl(octadecyl)amino]propan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(CO)OCC CJLGREYPKZVCDD-UHFFFAOYSA-N 0.000 description 2
- MJYLNDRKTQCKNI-UHFFFAOYSA-N 2-methoxy-3-[methyl(octadecyl)amino]propan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(CO)OC MJYLNDRKTQCKNI-UHFFFAOYSA-N 0.000 description 2
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 201000005296 lung carcinoma Diseases 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000004565 tumor cell growth Effects 0.000 description 2
- JMMIQBNIFUGPOJ-UHFFFAOYSA-N (2-ethoxy-3-phenylmethoxypropyl) methanesulfonate Chemical compound CS(=O)(=O)OCC(OCC)COCC1=CC=CC=C1 JMMIQBNIFUGPOJ-UHFFFAOYSA-N 0.000 description 1
- UZRODHKANBIDEQ-UHFFFAOYSA-N (2-methoxy-3-phenylmethoxypropyl) methanesulfonate Chemical compound CS(=O)(=O)OCC(OC)COCC1=CC=CC=C1 UZRODHKANBIDEQ-UHFFFAOYSA-N 0.000 description 1
- DVMSBLKKOUDZGO-UHFFFAOYSA-N 1-(18-benzylsulfonyloctadecylamino)-2-methoxypropan-1-ol Chemical compound C(C1=CC=CC=C1)S(=O)(=O)CCCCCCCCCCCCCCCCCCNC(C(C)OC)O DVMSBLKKOUDZGO-UHFFFAOYSA-N 0.000 description 1
- XJKSISNAIWKYAG-UHFFFAOYSA-N 1-bromo-5-isocyanatopentane Chemical compound BrCCCCCN=C=O XJKSISNAIWKYAG-UHFFFAOYSA-N 0.000 description 1
- BRFKGNAQKMAVPT-UHFFFAOYSA-N 18-benzylsulfonyl-n-(3-methoxy-2-phenylmethoxypropyl)octadecan-1-amine Chemical compound C=1C=CC=CC=1COC(COC)CNCCCCCCCCCCCCCCCCCCS(=O)(=O)CC1=CC=CC=C1 BRFKGNAQKMAVPT-UHFFFAOYSA-N 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethyl hydrogen phosphate Chemical class C[N+](C)(C)CCOP(O)([O-])=O YHHSONZFOIEMCP-UHFFFAOYSA-N 0.000 description 1
- AUDDNHGBAJNKEH-UHFFFAOYSA-N 2-Phenyl-1,3-dioxolane-4-methanol Chemical compound O1C(CO)COC1C1=CC=CC=C1 AUDDNHGBAJNKEH-UHFFFAOYSA-N 0.000 description 1
- IVFZIJPESUHPAP-UHFFFAOYSA-N 2-ethoxy-3-phenylmethoxypropan-1-ol Chemical compound CCOC(CO)COCC1=CC=CC=C1 IVFZIJPESUHPAP-UHFFFAOYSA-N 0.000 description 1
- PJYHMYSEOAAVMH-UHFFFAOYSA-N 2-methoxy-1-phenylmethoxypropan-1-amine Chemical compound NC(C(C)OC)OCC1=CC=CC=C1 PJYHMYSEOAAVMH-UHFFFAOYSA-N 0.000 description 1
- UFNGFGYICQRXIY-UHFFFAOYSA-N 5-bromohexanoyl chloride Chemical compound CC(Br)CCCC(Cl)=O UFNGFGYICQRXIY-UHFFFAOYSA-N 0.000 description 1
- ISACIJFHWGFOIU-UHFFFAOYSA-N 5-ethoxy-2-phenyl-1,3-dioxane Chemical compound O1CC(OCC)COC1C1=CC=CC=C1 ISACIJFHWGFOIU-UHFFFAOYSA-N 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 101150061618 Cnga1 gene Proteins 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006799 invasive growth in response to glucose limitation Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- KCDCBSGCJLVZND-UHFFFAOYSA-N n-(2-ethoxy-3-phenylmethoxypropyl)-n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(OCC)COCC1=CC=CC=C1 KCDCBSGCJLVZND-UHFFFAOYSA-N 0.000 description 1
- SIYUYHKHJHZJRV-UHFFFAOYSA-N n-(2-methoxy-3-phenylmethoxypropyl)-n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(OC)COCC1=CC=CC=C1 SIYUYHKHJHZJRV-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- 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
- 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
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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Hydrogenated Pyridines (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898929074A GB8929074D0 (en) | 1989-12-22 | 1989-12-22 | Glycerol derivatives |
| GB898929075A GB8929075D0 (en) | 1989-12-22 | 1989-12-22 | Glycerol derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9003973D0 SE9003973D0 (sv) | 1990-12-12 |
| SE9003973L SE9003973L (sv) | 1991-06-23 |
| SE501393C2 true SE501393C2 (sv) | 1995-02-06 |
Family
ID=26296423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9003973A SE501393C2 (sv) | 1989-12-22 | 1990-12-12 | Glycerolderivat, ett framställningsförfarande för desamma samt terapeutiska kompositioner innehållande dem |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5116992A (fr) |
| JP (1) | JP2648730B2 (fr) |
| KR (1) | KR950012533B1 (fr) |
| AR (1) | AR247875A1 (fr) |
| AT (1) | AT398423B (fr) |
| AU (1) | AU635991B2 (fr) |
| BE (1) | BE1004091A3 (fr) |
| CA (1) | CA2032254C (fr) |
| CH (1) | CH681225A5 (fr) |
| DE (1) | DE4041449A1 (fr) |
| DK (1) | DK171021B1 (fr) |
| ES (1) | ES2027550A6 (fr) |
| FI (1) | FI906203A (fr) |
| FR (2) | FR2656221B1 (fr) |
| GR (1) | GR1000688B (fr) |
| HK (1) | HK117993A (fr) |
| IE (1) | IE65821B1 (fr) |
| IT (1) | IT1243413B (fr) |
| LU (1) | LU87860A1 (fr) |
| NL (1) | NL9002742A (fr) |
| NO (1) | NO178698C (fr) |
| NZ (1) | NZ236483A (fr) |
| OA (1) | OA09336A (fr) |
| PT (1) | PT96322B (fr) |
| SE (1) | SE501393C2 (fr) |
| TN (1) | TNSN90153A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8928580D0 (en) * | 1989-12-19 | 1990-02-21 | Scras | 3-(n-methyl-n-alkylamino)-methoxymethyl-propanol phosphocholine derivatives |
| US5206027A (en) * | 1990-09-13 | 1993-04-27 | Fuji Photo Film Co., Ltd. | Amphipathic compound and liposome comprising the same |
| US5962437A (en) | 1994-08-29 | 1999-10-05 | Wake Forest University | Lipid analogs for treating viral infections |
| US7135584B2 (en) * | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| US5707978A (en) * | 1994-11-22 | 1998-01-13 | Clarion Pharmaceuticals Inc. | Heteroaryl-substituted deoxy glycero-phosphoethanolamines |
| US5665714A (en) * | 1995-12-07 | 1997-09-09 | Clarion Pharmaceuticals Inc. | N-substituted glycerophosphoethanolamines |
| US5703062A (en) * | 1995-12-07 | 1997-12-30 | Clarion Pharmaceuticals Inc. | N-het-substituted glycerophosphoethanolamines |
| US5730157A (en) * | 1995-12-07 | 1998-03-24 | Clarion Pharmaceuticals Inc. | Method for treating viral infection |
| US5827836A (en) * | 1996-11-15 | 1998-10-27 | Clarion Pharmaceuticals Inc. | Retinoid glycerol phospholipid conjugates |
| US5891881A (en) * | 1997-11-21 | 1999-04-06 | Clarion Pharmaceuticals Inc. | Aminoheterocycle-substituted glycerols |
| US20050187192A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Pharmaceutical Company | Phospholipids for the treatment of infection by togaviruses, herpes viruses and coronaviruses |
| PL2574341T3 (pl) | 2004-03-29 | 2017-09-29 | University Of South Florida | Efektywne leczenie guzów i raka fosforanem tricyrybiny |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2820893C2 (de) * | 1978-05-12 | 1986-02-20 | A. Nattermann & Cie GmbH, 5000 Köln | Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen |
| US4562179A (en) * | 1982-04-19 | 1985-12-31 | Fujisawa Pharmaceutical Co., Ltd. | Phospholipid derivatives, and pharmaceutical composition of the same |
| DE3323871A1 (de) * | 1983-07-02 | 1985-01-03 | A. Nattermann & Cie GmbH, 5000 Köln | Neue 1-o-alkyl-3-amino-propan-1,2-diol-2-o-phospholipide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4863941A (en) * | 1985-06-18 | 1989-09-05 | Hoffmann-La Roche Inc. | Glycerol derivatives |
-
1990
- 1990-12-07 GR GR900100847A patent/GR1000688B/el unknown
- 1990-12-12 SE SE9003973A patent/SE501393C2/sv unknown
- 1990-12-12 NO NO905377A patent/NO178698C/no unknown
- 1990-12-13 NL NL9002742A patent/NL9002742A/nl not_active Application Discontinuation
- 1990-12-14 LU LU87860A patent/LU87860A1/fr unknown
- 1990-12-14 CA CA002032254A patent/CA2032254C/fr not_active Expired - Fee Related
- 1990-12-17 FI FI906203A patent/FI906203A/fi not_active Application Discontinuation
- 1990-12-17 CH CH4007/90A patent/CH681225A5/fr not_active IP Right Cessation
- 1990-12-17 NZ NZ236483A patent/NZ236483A/xx unknown
- 1990-12-18 AR AR90318644A patent/AR247875A1/es active
- 1990-12-18 BE BE9001220A patent/BE1004091A3/fr not_active IP Right Cessation
- 1990-12-19 FR FR909015903A patent/FR2656221B1/fr not_active Expired - Fee Related
- 1990-12-19 FR FR9015902A patent/FR2656308B1/fr not_active Expired - Fee Related
- 1990-12-19 IT IT02243990A patent/IT1243413B/it active IP Right Grant
- 1990-12-19 US US07/630,296 patent/US5116992A/en not_active Expired - Fee Related
- 1990-12-19 TN TNTNSN90153A patent/TNSN90153A1/fr unknown
- 1990-12-20 IE IE461890A patent/IE65821B1/en not_active IP Right Cessation
- 1990-12-20 AT AT0260590A patent/AT398423B/de not_active IP Right Cessation
- 1990-12-21 PT PT96322A patent/PT96322B/pt not_active IP Right Cessation
- 1990-12-21 ES ES9003271A patent/ES2027550A6/es not_active Expired - Fee Related
- 1990-12-21 DE DE4041449A patent/DE4041449A1/de not_active Ceased
- 1990-12-21 AU AU68379/90A patent/AU635991B2/en not_active Ceased
- 1990-12-21 DK DK304090A patent/DK171021B1/da not_active IP Right Cessation
- 1990-12-21 OA OA59931A patent/OA09336A/fr unknown
- 1990-12-21 KR KR1019900021354A patent/KR950012533B1/ko not_active IP Right Cessation
- 1990-12-21 JP JP2419284A patent/JP2648730B2/ja not_active Expired - Lifetime
-
1993
- 1993-11-04 HK HK1179/93A patent/HK117993A/xx not_active IP Right Cessation
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