FI60218C - Foerfarande foer framstaellning av terapeutiskt anvaendbara dubbelsalter av s-adenosyl-l-metionin - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara dubbelsalter av s-adenosyl-l-metionin Download PDFInfo
- Publication number
- FI60218C FI60218C FI1954/74A FI195474A FI60218C FI 60218 C FI60218 C FI 60218C FI 1954/74 A FI1954/74 A FI 1954/74A FI 195474 A FI195474 A FI 195474A FI 60218 C FI60218 C FI 60218C
- Authority
- FI
- Finland
- Prior art keywords
- sam
- solution
- salt
- acid
- methanol
- Prior art date
Links
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 title claims description 103
- 230000001225 therapeutic effect Effects 0.000 title description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 52
- 239000000243 solution Substances 0.000 claims description 46
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- OVFUUSPKWADLNJ-UHFFFAOYSA-N 5-methyl-4-nitro-2-(4-nitrophenyl)-4h-pyrazol-3-one Chemical compound O=C1C([N+]([O-])=O)C(C)=NN1C1=CC=C([N+]([O-])=O)C=C1 OVFUUSPKWADLNJ-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- -1 salt salt Chemical class 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 108090000790 Enzymes Proteins 0.000 description 21
- 102000004190 Enzymes Human genes 0.000 description 21
- 230000000694 effects Effects 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 230000004060 metabolic process Effects 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- 210000004185 liver Anatomy 0.000 description 10
- 229960004452 methionine Drugs 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 7
- 239000003610 charcoal Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- 230000002255 enzymatic effect Effects 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 150000004676 glycans Chemical class 0.000 description 6
- 229930182817 methionine Natural products 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 229920001282 polysaccharide Polymers 0.000 description 6
- 239000005017 polysaccharide Substances 0.000 description 6
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 5
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 4
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 229920002684 Sepharose Polymers 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229960004502 levodopa Drugs 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102000003960 Ligases Human genes 0.000 description 3
- 108090000364 Ligases Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 102000016397 Methyltransferase Human genes 0.000 description 3
- 108060004795 Methyltransferase Proteins 0.000 description 3
- ZJUKTBDSGOFHSH-WFMPWKQPSA-N S-Adenosylhomocysteine Chemical compound O[C@@H]1[C@H](O)[C@@H](CSCC[C@H](N)C(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZJUKTBDSGOFHSH-WFMPWKQPSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 230000003001 depressive effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 210000005253 yeast cell Anatomy 0.000 description 3
- UCTWMZQNUQWSLP-SECBINFHSA-N (S)-adrenaline Chemical compound CNC[C@@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-SECBINFHSA-N 0.000 description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000235646 Cyberlindnera jadinii Species 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 206010019708 Hepatic steatosis Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010029240 Neuritis Diseases 0.000 description 2
- 208000008457 Neurologic Manifestations Diseases 0.000 description 2
- NPWOOAHIGDMWDM-UHFFFAOYSA-N OS(O)(=O)=O.OS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 NPWOOAHIGDMWDM-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 208000030713 Parkinson disease and parkinsonism Diseases 0.000 description 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 230000001760 anti-analgesic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- 238000005842 biochemical reaction Methods 0.000 description 2
- 230000000035 biogenic effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- NGKZFDYBISXGGS-UHFFFAOYSA-N epinine Chemical compound CNCCC1=CC=C(O)C(O)=C1 NGKZFDYBISXGGS-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- BPMFZUMJYQTVII-UHFFFAOYSA-N guanidinoacetic acid Chemical compound NC(=N)NCC(O)=O BPMFZUMJYQTVII-UHFFFAOYSA-N 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 231100000869 headache Toxicity 0.000 description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 2
- 229960002456 hexobarbital Drugs 0.000 description 2
- KUBCEEMXQZUPDQ-UHFFFAOYSA-N hordenine Chemical compound CN(C)CCC1=CC=C(O)C=C1 KUBCEEMXQZUPDQ-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 206010022437 insomnia Diseases 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000012633 leachable Substances 0.000 description 2
- 230000037356 lipid metabolism Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000003908 liver function Effects 0.000 description 2
- 230000036244 malformation Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- PETSAYFQSGAEQY-UHFFFAOYSA-N ricinine Chemical compound COC=1C=CN(C)C(=O)C=1C#N PETSAYFQSGAEQY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 230000004622 sleep time Effects 0.000 description 2
- 230000008454 sleep-wake cycle Effects 0.000 description 2
- 229910021653 sulphate ion Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- MGBKJKDRMRAZKC-UHFFFAOYSA-N 3-aminobenzene-1,2-diol Chemical compound NC1=CC=CC(O)=C1O MGBKJKDRMRAZKC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SQASAHFPWITLNX-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;sulfo hydrogen sulfate Chemical compound OS(=O)(=O)OS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 SQASAHFPWITLNX-UHFFFAOYSA-N 0.000 description 1
- YPXFPFYXLHQFQR-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1 YPXFPFYXLHQFQR-UHFFFAOYSA-N 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 206010001605 Alcohol poisoning Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000002381 Brain Hypoxia Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 101100094968 Caenorhabditis elegans sam-10 gene Proteins 0.000 description 1
- 208000001378 Carbon Tetrachloride Poisoning Diseases 0.000 description 1
- QRYRORQUOLYVBU-VBKZILBWSA-N Carnosic acid Natural products CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 description 1
- 108010087806 Carnosine Proteins 0.000 description 1
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 101000720704 Homo sapiens Neuronal migration protein doublecortin Proteins 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010023230 Joint stiffness Diseases 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 108010007784 Methionine adenosyltransferase Proteins 0.000 description 1
- 102000007357 Methionine adenosyltransferase Human genes 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 102100025929 Neuronal migration protein doublecortin Human genes 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241001537210 Perna Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 108010051753 Spermidine Synthase Proteins 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010044074 Torticollis Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 206010000059 abdominal discomfort Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229960001570 ademetionine Drugs 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- ZGLIQORZYPZFPW-UHFFFAOYSA-K azanium;azane;chromium(3+);tetrathiocyanate Chemical compound N.N.[NH4+].[Cr+3].[S-]C#N.[S-]C#N.[S-]C#N.[S-]C#N ZGLIQORZYPZFPW-UHFFFAOYSA-K 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 description 1
- 229940044199 carnosine Drugs 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000132 chronic toxicity testing Toxicity 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 229960003624 creatine Drugs 0.000 description 1
- 239000006046 creatine Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 238000002565 electrocardiography Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229940071490 hordenine Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000018197 inherited torticollis Diseases 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000006372 lipid accumulation Effects 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- KRGPXXHMOXVMMM-UHFFFAOYSA-N nicotianamine Natural products OC(=O)C(N)CCNC(C(O)=O)CCN1CCC1C(O)=O KRGPXXHMOXVMMM-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229960000292 pectin Drugs 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 208000019629 polyneuritis Diseases 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000022558 protein metabolic process Effects 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1085—Transferases (2.) transferring alkyl or aryl groups other than methyl groups (2.5)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2589573 | 1973-06-27 | ||
IT2589573 | 1973-06-27 | ||
IT2314874 | 1974-05-24 | ||
IT2314874A IT1022036B (it) | 1974-05-24 | 1974-05-24 | Processo per la preparazione di sali enzimatici |
LU79038A LU79038A1 (fr) | 1973-06-27 | 1978-02-09 | Procede de preparation de sels enzymatiques |
LU79038 | 1978-02-09 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI195474A FI195474A (fr) | 1974-12-28 |
FI60218B FI60218B (fi) | 1981-08-31 |
FI60218C true FI60218C (fi) | 1981-12-10 |
Family
ID=27273344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI1954/74A FI60218C (fi) | 1973-06-27 | 1974-06-26 | Foerfarande foer framstaellning av terapeutiskt anvaendbara dubbelsalter av s-adenosyl-l-metionin |
Country Status (19)
Country | Link |
---|---|
US (1) | US3954726A (fr) |
JP (1) | JPS5235727B2 (fr) |
AR (1) | AR202219A1 (fr) |
AT (1) | AT347604B (fr) |
BE (1) | BE816915A (fr) |
CA (1) | CA1024088A (fr) |
CH (1) | CH592686A5 (fr) |
DD (1) | DD112451A5 (fr) |
DE (1) | DE2430999C2 (fr) |
DK (1) | DK137279B (fr) |
FI (1) | FI60218C (fr) |
FR (1) | FR2234891B1 (fr) |
GB (1) | GB1443587A (fr) |
HK (1) | HK31680A (fr) |
IE (1) | IE39517B1 (fr) |
LU (1) | LU79038A1 (fr) |
NL (1) | NL176276C (fr) |
RO (1) | RO64135A (fr) |
SE (1) | SE408712B (fr) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR221676A1 (es) * | 1974-07-12 | 1981-03-13 | Bioresearch Sas | Procedimiento para la preparacion de sales estables sulfonicas y/o sulfuricas de la s-adenosil-l-metionina,particularmente utiles como donadores especificos de metilo para las reacciones bioquimicas de transferencia del grupo ch3;asi como tambien las reacciones fundamentales en el metabolismo lipilico,protilico y glucidico |
DE2646269A1 (de) * | 1975-10-16 | 1977-04-28 | Yamasa Shoyu Kk | Stabilisierte s-adenosyl-l-methionin- zubereitung und verfahren zur herstellung derselben |
GB2001976B (en) * | 1977-08-03 | 1982-03-10 | Yamasa Shoyu Kk | S-adenosyl-l-methionine compositions and production thereof |
JPS5428808A (en) * | 1977-08-03 | 1979-03-03 | Yamasa Shoyu Co Ltd | Composition containing s-adenoyl-l-methionine and its preparation |
GB2064523B (en) * | 1979-12-04 | 1983-06-29 | Kanegafuchi Chemical Ind | Stable composition of s-adenosyl-l-methionine |
IT1137640B (it) | 1981-08-24 | 1986-09-10 | Bioresearch Srl | Sali stabili della s-adenosilmetionina,processo per la loro preparazione e composizioni terapeutiche che li comprendono come principio attivo |
US4376116A (en) * | 1981-09-01 | 1983-03-08 | Research Corporation | Polyamine biosynthesis inhibitors |
IT1139974B (it) * | 1981-09-11 | 1986-09-24 | Bioresearch Srl | Derivati della s-adenosilmetionina,processo per la preparazione e composizioni terapeutiche che li contengono come principio attivo |
JPS59196408U (ja) * | 1983-06-16 | 1984-12-27 | 株式会社 永幸 | 筒形容器 |
IT1169773B (it) * | 1983-08-24 | 1987-06-03 | Bioresearch Spa | Processo per la produzione di sali stabili della solfo-adenosil-l-metionina |
IT1173992B (it) * | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente idonei per uso farmaceutico orale |
IT1173990B (it) * | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente adatti per uso parenterale |
US4794174A (en) * | 1987-02-10 | 1988-12-27 | Southern Research Institute | 5'deoxy-5'-substituted adenosines |
ATE80165T1 (de) * | 1987-10-09 | 1992-09-15 | Vincenzo Zappia | Lipophile salze von s-adenosyl-l-methionin (sam) mit acyltaurinderivaten. |
JPH02290896A (ja) * | 1989-04-28 | 1990-11-30 | Fuji Kagaku Kogyo Kk | 新規なs―アデノシルメチオニン誘導体 |
JPH0576192U (ja) * | 1991-08-27 | 1993-10-15 | 株式会社河合楽器製作所 | 小型電子機器におけるマイクロフオンの保持機構 |
JP3491938B2 (ja) * | 1993-12-13 | 2004-02-03 | キヤノン株式会社 | Dnaの回収方法 |
IT1318535B1 (it) * | 2000-05-25 | 2003-08-27 | Chementecno Srl | Processo per la preparazione di sali farmaceuticamente accettabili di(ss,rs)-s-adenosil-l-metionina. |
US6759395B2 (en) * | 2000-12-18 | 2004-07-06 | Orchid Chemicals & Pharmaceuticals, Ltd. | Soft-gelatin capsule comprising S-adenosylmethionine and a method for producing the same |
US6649753B2 (en) | 2001-06-07 | 2003-11-18 | Orchid Chemicals & Pharmaceuticals Ltd. | Stable salts of S-adenosyl-L-methionine (SAMe) and the process for their preparation |
WO2002102823A1 (fr) * | 2001-06-14 | 2002-12-27 | Orchid Chemicals & Pharmaceuticals Limited | Sels stables de s-adenosyl-l-methionine (same) et procede de preparation |
US20050272687A1 (en) * | 2004-06-08 | 2005-12-08 | Hebert Rolland F | Stable S-adenosyl-l-methionine |
FR2884421B1 (fr) | 2005-04-15 | 2007-08-10 | Virbac Sa | Nouveaux moyens de regulation des troubles du comportement chez les animaux de compagnie |
AU2006237346B2 (en) * | 2005-04-20 | 2011-04-07 | Basf Plant Science Gmbh | Expression cassettes for seed-preferential expression in plants |
US20090012036A1 (en) * | 2005-05-24 | 2009-01-08 | Hebert Rolland F | Stable S-adenosyl-L-methionine |
ITRM20050344A1 (it) * | 2005-06-30 | 2007-01-01 | Luca Maria De | Sali o complessi di sostanze metil-donatrici con acido fitico o suoi derivati e relativo metodo di sintesi. |
JP5071112B2 (ja) * | 2006-01-17 | 2012-11-14 | 三菱瓦斯化学株式会社 | S−アデノシル−l−メチオニンの安定化法及び安定化された組成物 |
ITMI20060629A1 (it) | 2006-03-31 | 2007-10-01 | Daniele Giovannone | Composizioni solide orali a base di s-adenosilmetionina e processo per il loro ottenimento |
US20090197824A1 (en) * | 2008-01-31 | 2009-08-06 | Methylation Sciences International Srl | Extended Release Pharmaceutical Formulations of S-Adenosylmethionine |
AU2008210327B2 (en) * | 2007-01-31 | 2011-06-16 | Methylation Sciences International Srl | Extended release pharmaceutical formulations of S-adenosylmethionine |
US20090088404A1 (en) * | 2007-01-31 | 2009-04-02 | Methylation Sciences International Srl | Extended Release Pharmaceutical Formulations of S-Adenosylmethionine |
ITMI20071374A1 (it) * | 2007-07-10 | 2009-01-11 | Gnosis Spa | Sali stabili di s-adenosilmetionina e processo per il loro ottenimento. |
US20100004191A1 (en) * | 2008-07-01 | 2010-01-07 | Rolland F Hebert | Compositions of S-adenosyl-L-methionine. |
EP2189154A1 (fr) | 2008-11-25 | 2010-05-26 | Gnosis S.p.A. | Comprimés effervescents et granulés solubles dans la bouche de S-adénosy-L-méthionine et son procédé de préparation |
IT1393331B1 (it) * | 2009-02-09 | 2012-04-20 | Graal S R L | Composizioni orosolubili e/o effervescenti contenenti almeno un sale di s-adenosilmetionina (same) |
US20110027342A1 (en) | 2009-07-28 | 2011-02-03 | Msi Methylation Sciences, Inc. | S-adenosylmethionine formulations with enhanced bioavailability |
US8329208B2 (en) | 2009-07-28 | 2012-12-11 | Methylation Sciences International Srl | Pharmacokinetics of S-adenosylmethionine formulations |
WO2014113609A1 (fr) | 2013-01-16 | 2014-07-24 | Hebert Sam-E Llc | Sels d'indole-3-propionate stables de la s-adénosyl-l-méthionine |
WO2014163150A1 (fr) * | 2013-04-05 | 2014-10-09 | ライオン株式会社 | Composition à usage interne |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3642772A (en) * | 1968-09-04 | 1972-02-15 | Boehringer Mannheim Gmbh | Process for preparing s-adenosyl homocysteine |
DE1803978C2 (de) * | 1968-10-18 | 1985-05-02 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur Gewinnung von S-Adenosyl-l-methionin und S-Adenosyl-l-ethionin |
IE37913B1 (en) * | 1972-08-02 | 1977-11-09 | Bioresearch Sas | Salt of s-adenosyl-l-methionine |
-
1974
- 1974-06-20 IE IE1295/74A patent/IE39517B1/xx unknown
- 1974-06-24 US US05/482,153 patent/US3954726A/en not_active Expired - Lifetime
- 1974-06-24 GB GB2788874A patent/GB1443587A/en not_active Expired
- 1974-06-25 FR FR7422056A patent/FR2234891B1/fr not_active Expired
- 1974-06-26 DD DD179487A patent/DD112451A5/xx unknown
- 1974-06-26 BE BE145935A patent/BE816915A/fr not_active IP Right Cessation
- 1974-06-26 FI FI1954/74A patent/FI60218C/fi active
- 1974-06-26 CH CH877074A patent/CH592686A5/xx not_active IP Right Cessation
- 1974-06-26 AR AR254406A patent/AR202219A1/es active
- 1974-06-26 DK DK342974AA patent/DK137279B/da unknown
- 1974-06-26 SE SE7408388A patent/SE408712B/xx not_active IP Right Cessation
- 1974-06-27 AT AT532574A patent/AT347604B/de not_active IP Right Cessation
- 1974-06-27 NL NLAANVRAGE7408688,A patent/NL176276C/xx not_active IP Right Cessation
- 1974-06-27 CA CA203,583A patent/CA1024088A/fr not_active Expired
- 1974-06-27 JP JP49072882A patent/JPS5235727B2/ja not_active Expired
- 1974-06-27 RO RO7400085149A patent/RO64135A/fr unknown
- 1974-06-27 DE DE2430999A patent/DE2430999C2/de not_active Expired
-
1978
- 1978-02-09 LU LU79038A patent/LU79038A1/fr unknown
-
1980
- 1980-06-12 HK HK316/80A patent/HK31680A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DK137279B (da) | 1978-02-13 |
LU79038A1 (fr) | 1978-06-26 |
IE39517B1 (en) | 1978-10-25 |
FR2234891A1 (fr) | 1975-01-24 |
US3954726A (en) | 1976-05-04 |
FR2234891B1 (fr) | 1977-03-11 |
FI195474A (fr) | 1974-12-28 |
BE816915A (fr) | 1974-10-16 |
IE39517L (en) | 1974-12-27 |
SE7408388L (fr) | 1974-12-30 |
DK342974A (fr) | 1975-03-17 |
DD112451A5 (fr) | 1975-04-12 |
SE408712B (sv) | 1979-07-02 |
NL176276B (nl) | 1984-10-16 |
DE2430999C2 (de) | 1982-06-09 |
NL176276C (nl) | 1985-03-18 |
GB1443587A (en) | 1976-07-21 |
DE2430999A1 (de) | 1975-01-16 |
FI60218B (fi) | 1981-08-31 |
NL7408688A (fr) | 1974-12-31 |
CH592686A5 (fr) | 1977-11-15 |
JPS5076215A (fr) | 1975-06-21 |
JPS5235727B2 (fr) | 1977-09-10 |
RO64135A (fr) | 1978-11-15 |
AU7068974A (en) | 1976-01-08 |
HK31680A (en) | 1980-06-20 |
AT347604B (de) | 1979-01-10 |
ATA532574A (de) | 1978-05-15 |
AR202219A1 (es) | 1975-05-23 |
CA1024088A (fr) | 1978-01-10 |
DK137279C (fr) | 1978-07-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI60218C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara dubbelsalter av s-adenosyl-l-metionin | |
FI63037C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara stbila sulfonater av s-adenosyl-l-metionin | |
US3893999A (en) | Salt of S-adenosil-L-methionine and process of preparation | |
Ueland | Pharmacological and biochemical aspects of S-adenosylhomocysteine and S-adenosylhomocysteine hydrolase. | |
CA1256868A (fr) | Composes lipoidiques de biopterine | |
EP0072980B1 (fr) | Sels de S-adénosinylméthione stables, leur procédé de préparation, et compostions pharmaceutiques les contenant comme substance active | |
Bremer | Carnitine precursors in the rat | |
Cox et al. | Biosynthesis of carnitine and 4-N-trimethylaminobutyrate from lysine | |
Allen | Role of amantadine in the management of neuroleptic-induced extrapyramidal syndromes: overview and pharmacology | |
US4028183A (en) | Process of preparing double salts of S-adenosyl-L-methionine | |
JPH101436A (ja) | ウリジンまたはシチジンのアシル誘導体を含有する医薬組成物 | |
FI72525C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara stabila s-adenocylmetioninsalter. | |
US20050272687A1 (en) | Stable S-adenosyl-l-methionine | |
NZ201824A (en) | S-adenosylmethionine derivatives and pharmaceutical compositions | |
JPH06509350A (ja) | 新規なガングリオシド誘導体 | |
Chandra et al. | Effect of manganese on synthesis of brain catecholamines in growing rats | |
US20030144244A1 (en) | Stable compositions of S-adenosyl-l-methionine with dextran | |
JPS61176598A (ja) | シチジン−ジホスフエ−ト−コリンのアシル化誘導体、その製造方法及びその治療的使用 | |
JPH05506842A (ja) | 神経変性状態の処置方法 | |
US20120040923A1 (en) | Stable s-adenosyl-l-methionine | |
Porcelli et al. | Biosynthesis and metabolism of 9-[5′-deoxy-5′-(methylthio)-β-d-xylofuranosyl] adenine, a novel natural analogue of methylthioadenosine | |
NO139523B (no) | Fremgangsmaate for fremstilling av doble salter av s-adenosil-l-methionin | |
PL95666B1 (pl) | Sposob wytwarzania nowych podwojnych soli s-adenozylo-alfa-metioniny | |
Snyder et al. | Amines in schizophrenia | |
WAGNER et al. | Vitamin B12 |