DE2530898C2 - - Google Patents
Info
- Publication number
- DE2530898C2 DE2530898C2 DE2530898A DE2530898A DE2530898C2 DE 2530898 C2 DE2530898 C2 DE 2530898C2 DE 2530898 A DE2530898 A DE 2530898A DE 2530898 A DE2530898 A DE 2530898A DE 2530898 C2 DE2530898 C2 DE 2530898C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sam
- solution
- salt
- sulfonic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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 claims description 125
- 239000000243 solution Substances 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 59
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 57
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical group OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000002244 precipitate Substances 0.000 claims description 21
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 19
- 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 18
- 239000000203 mixture Substances 0.000 claims description 18
- 235000011149 sulphuric acid Nutrition 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 15
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 150000003460 sulfonic acids Chemical class 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 10
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical group CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical group CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical group CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 7
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 6
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical group OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims description 6
- WQPMYSHJKXVTME-UHFFFAOYSA-N 3-hydroxypropane-1-sulfonic acid Chemical compound OCCCS(O)(=O)=O WQPMYSHJKXVTME-UHFFFAOYSA-N 0.000 claims description 5
- XDTYUYVIGLIFCW-UHFFFAOYSA-N 4-phenylbenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=CC=C1 XDTYUYVIGLIFCW-UHFFFAOYSA-N 0.000 claims description 5
- -1 5-sulfosalicyl Chemical group 0.000 claims description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 5
- CACRRXGTWZXOAU-UHFFFAOYSA-N octadecane-1-sulfonic acid Chemical group CCCCCCCCCCCCCCCCCCS(O)(=O)=O CACRRXGTWZXOAU-UHFFFAOYSA-N 0.000 claims description 5
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 claims description 4
- ACPXHHDRVABPNY-UHFFFAOYSA-N 4-acetylbenzenesulfonic acid Chemical compound CC(=O)C1=CC=C(S(O)(=O)=O)C=C1 ACPXHHDRVABPNY-UHFFFAOYSA-N 0.000 claims description 4
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims description 4
- XVOYSCVBGLVSOL-REOHCLBHSA-N L-cysteic acid Chemical compound OC(=O)[C@@H](N)CS(O)(=O)=O XVOYSCVBGLVSOL-REOHCLBHSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 description 21
- 230000004060 metabolic process Effects 0.000 description 19
- 238000001556 precipitation Methods 0.000 description 19
- 238000011282 treatment Methods 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 16
- 238000001914 filtration Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 238000006911 enzymatic reaction Methods 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 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 10
- 230000000694 effects Effects 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 230000002440 hepatic effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 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 6
- 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 6
- 238000010255 intramuscular injection Methods 0.000 description 6
- 238000010253 intravenous injection Methods 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 239000003245 coal Substances 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- 229960004452 methionine Drugs 0.000 description 5
- 235000018102 proteins Nutrition 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 4
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 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 4
- 229930182817 methionine Natural products 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 230000001575 pathological effect Effects 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000936 Agarose Polymers 0.000 description 3
- 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 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
- 102000003960 Ligases Human genes 0.000 description 3
- 108090000364 Ligases Proteins 0.000 description 3
- 102000016397 Methyltransferase Human genes 0.000 description 3
- 108060004795 Methyltransferase Proteins 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000003001 depressive effect Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229960004502 levodopa Drugs 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000000926 neurological effect Effects 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 230000004622 sleep time Effects 0.000 description 3
- 230000008454 sleep-wake cycle Effects 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- MGBKJKDRMRAZKC-UHFFFAOYSA-N 3-aminobenzene-1,2-diol Chemical class NC1=CC=CC(O)=C1O MGBKJKDRMRAZKC-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 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
- 108010007784 Methionine adenosyltransferase Proteins 0.000 description 2
- 102000007357 Methionine adenosyltransferase Human genes 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 206010029240 Neuritis Diseases 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
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- 229910006069 SO3H Inorganic materials 0.000 description 2
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 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
- 230000000146 antalgic effect Effects 0.000 description 2
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- 229940125717 barbiturate Drugs 0.000 description 2
- 238000005842 biochemical reaction Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007665 chronic toxicity Effects 0.000 description 2
- 231100000160 chronic toxicity Toxicity 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229960003624 creatine Drugs 0.000 description 2
- 239000006046 creatine Substances 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-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
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 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
- 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
- 229960000905 indomethacin Drugs 0.000 description 2
- 206010022437 insomnia Diseases 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 229940035429 isobutyl alcohol Drugs 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
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- 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
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2512874 | 1974-07-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2530898A1 DE2530898A1 (de) | 1976-01-29 |
| DE2530898C2 true DE2530898C2 (en, 2012) | 1988-08-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752530898 Granted DE2530898A1 (de) | 1974-07-12 | 1975-07-10 | Sulfonsaeuresalze von s-adenosylmethionin, verfahren zu deren herstellung und die genannten salze enthaltende therapeutische zusammensetzungen |
Country Status (27)
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| US (1) | US4057686A (en, 2012) |
| JP (1) | JPS51125717A (en, 2012) |
| AR (1) | AR221676A1 (en, 2012) |
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| AU (1) | AU498365B2 (en, 2012) |
| BE (1) | BE831310A (en, 2012) |
| CA (1) | CA1057681A (en, 2012) |
| CH (1) | CH606085A5 (en, 2012) |
| DD (1) | DD118643A5 (en, 2012) |
| DE (1) | DE2530898A1 (en, 2012) |
| DK (1) | DK144946C (en, 2012) |
| ES (1) | ES439316A1 (en, 2012) |
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| FR (1) | FR2277590A1 (en, 2012) |
| GB (1) | GB1506640A (en, 2012) |
| HU (1) | HU170264B (en, 2012) |
| IE (1) | IE41421B1 (en, 2012) |
| IL (1) | IL47656A (en, 2012) |
| NL (1) | NL171987C (en, 2012) |
| NO (1) | NO142175C (en, 2012) |
| NZ (1) | NZ178014A (en, 2012) |
| PL (1) | PL94268B1 (en, 2012) |
| RO (1) | RO77525A (en, 2012) |
| SE (1) | SE420204B (en, 2012) |
| SU (1) | SU676169A3 (en, 2012) |
| YU (1) | YU39271B (en, 2012) |
| ZA (1) | ZA754167B (en, 2012) |
Families Citing this family (51)
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| JPS5428808A (en) * | 1977-08-03 | 1979-03-03 | Yamasa Shoyu Co Ltd | Composition containing s-adenoyl-l-methionine and its preparation |
| GB2001976B (en) * | 1977-08-03 | 1982-03-10 | Yamasa Shoyu Kk | S-adenosyl-l-methionine compositions and production thereof |
| JPS5596099A (en) * | 1979-01-12 | 1980-07-21 | Tanabe Seiyaku Co Ltd | Production of s-adenosyl-l-methionine using enzyme |
| GB2064523B (en) * | 1979-12-04 | 1983-06-29 | Kanegafuchi Chemical Ind | Stable composition of s-adenosyl-l-methionine |
| IT1137892B (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 |
| 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 |
| 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 |
| US4419358A (en) * | 1981-11-12 | 1983-12-06 | Mead Johnson & Company | Isethionic acid salt of 9-cyclohexyl-2-propoxy-9H-purine-6-amine and compositions containing an effective bronchodilating concentration of it |
| IT1169772B (it) * | 1983-08-24 | 1987-06-03 | Bioresearch Spa | Composizioni terapeutiche per uso orale contenenti sali stabili della s-adenosil-l-metionina |
| IT1169774B (it) * | 1983-08-24 | 1987-06-03 | Bioresearch Spa | Composizioni terapeutiche iniettabili contenenti sali stabili della s-adenosil-l-metionina |
| 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 |
| IT1177373B (it) * | 1984-12-06 | 1987-08-26 | Bioresearch Spa | Sali della 5'-metiltio-5'-deossiadenosina con acidi solfonici a lunga catena alchilica |
| IT1200589B (it) * | 1985-02-14 | 1989-01-27 | Gibipharma Spa | Derivati naturali attivita farmagologica |
| US4962451A (en) * | 1985-11-07 | 1990-10-09 | International Business Machines Corporation | Cache-effective sort string generation method |
| EP0395656B1 (en) * | 1987-10-09 | 1992-09-02 | ZAPPIA, Vincenzo | Lipophilic salts of s-adenosyl-l-methionine (sam) with acylated taurine derivatives |
| FR2623396B1 (fr) * | 1987-11-25 | 1990-03-30 | Sanofi Sa | Utilisation de l'ademetionine contre le vieillissement de la peau |
| IT1229477B (it) * | 1989-03-13 | 1991-09-03 | Bioresearch Spa | Impiego di 5' deossi - 5' metiltioadenosina, s adenosilmetionina e dei loro sali per la preparazione di composizioni farmaceutiche atte a ridurre la seborrea e composizioni farmaceutiche relative |
| 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 |
| JPH03123514U (en, 2012) * | 1990-03-27 | 1991-12-16 | ||
| US6399093B1 (en) | 1999-05-19 | 2002-06-04 | Advanced Medical Instruments | Method and composition to treat musculoskeletal disorders |
| US6635615B1 (en) * | 1999-11-17 | 2003-10-21 | Rolland F. Hebert | Stable salts of S-adenosyl-l-methionine |
| DE10022856A1 (de) * | 2000-05-10 | 2001-11-15 | Basf Ag | Therapeutische Kombination von Liponsäure und C1-Donoren zur Behandlung von Störungen des Zentralen Nervensystems |
| 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 |
| FR2823211A1 (fr) * | 2001-04-10 | 2002-10-11 | Virbac Sa | Composition a base d'un polyphosphate de s-adenosyl-l-methionine et utilisations d'un tel polyphosphate |
| US6881837B2 (en) | 2001-06-07 | 2005-04-19 | Orchid Chemicals & Pharmaceuticals Ltd. | Chemical synthesis of S-adenosyl-L-methionine with enrichment of (S,S)-isomer |
| 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 (en) * | 2001-06-14 | 2002-12-27 | Orchid Chemicals & Pharmaceuticals Limited | Stable salts of s-adenosyl-l-methionine (same) and the process for their preparation |
| US20050272687A1 (en) * | 2004-06-08 | 2005-12-08 | Hebert Rolland F | Stable S-adenosyl-l-methionine |
| KR20070048700A (ko) | 2004-06-23 | 2007-05-09 | 오키드 케미칼즈 앤드 파마수티컬즈 리미티드 | （ｓ，ｓ）－이성질체가 풍부한ｓ－아데노실－ｌ－메티오닌의 화학 합성 |
| US8063024B2 (en) * | 2005-01-26 | 2011-11-22 | University Of Manitoba | Use of S-adenosylmethionine, vitamin E, and vitamin C for the treatment of oxidative liver injury and insulin resistance |
| FR2884421B1 (fr) | 2005-04-15 | 2007-08-10 | Virbac Sa | Nouveaux moyens de regulation des troubles du comportement chez les animaux de compagnie |
| WO2006111541A2 (en) * | 2005-04-20 | 2006-10-26 | 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 |
| ITMI20060629A1 (it) * | 2006-03-31 | 2007-10-01 | Daniele Giovannone | Composizioni solide orali a base di s-adenosilmetionina e processo per il loro ottenimento |
| KR101070494B1 (ko) * | 2006-05-10 | 2011-10-05 | 미쓰비시 타나베 파마 코퍼레이션 | Ｓ-아데노실-ｌ-메티오닌 함유 건조 효모의 제조방법 및 경구 섭취용 조성물 |
| US20090197824A1 (en) * | 2008-01-31 | 2009-08-06 | Methylation Sciences International Srl | Extended Release Pharmaceutical Formulations of S-Adenosylmethionine |
| CN101677543A (zh) * | 2007-01-31 | 2010-03-24 | 甲基化物科学国际有限公司 | S-腺苷甲硫氨酸的延时释放药物制剂 |
| 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. |
| EP2193787A1 (en) * | 2008-12-02 | 2010-06-09 | Giorgio Stramentinoli | Formulations for systemic buccal delivery comprising s-adenosylmethionine, their preparation and use |
| US8329208B2 (en) | 2009-07-28 | 2012-12-11 | Methylation Sciences International Srl | Pharmacokinetics of S-adenosylmethionine formulations |
| US20110027342A1 (en) * | 2009-07-28 | 2011-02-03 | Msi Methylation Sciences, Inc. | S-adenosylmethionine formulations with enhanced bioavailability |
| WO2012139227A1 (en) | 2011-04-15 | 2012-10-18 | Scimar Ltd. | Use of s-adenosylmethionine, vitamin e, and vitamin c for the prevention and treatment of cardiovascular dysfunction |
| CN102321136B (zh) * | 2011-09-19 | 2014-10-22 | 北京化工大学 | S-腺苷-l-甲硫氨酸对甲苯磺酸硫酸双盐的制备方法 |
| KR20160094451A (ko) | 2012-10-17 | 2016-08-09 | 메틸레이션 사이언시즈 인터내셔널 에스알엘 | S-아데노실메티오닌 및 갈산 에스테르가 포함된 조성물 |
| JP6479681B2 (ja) | 2013-01-16 | 2019-03-06 | ヘーベルト サム−イー エルエルシー | Ｓ−アデノシル−ｌ−メチオニンの安定なインドール−３−プロピオネート塩 |
| RU2537556C1 (ru) * | 2013-07-30 | 2015-01-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Способ получения соли адеметионина с хондроитинсульфокислотой |
| WO2024238657A2 (en) | 2023-05-15 | 2024-11-21 | Bonafide Health, Llc | Sleep-improving compositions and methods of use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IE39517B1 (en) * | 1973-06-27 | 1978-10-25 | Bioresearch Sas | Double salts of s-adenosyl-l-methhionine |
-
1975
- 1975-01-01 AR AR259529A patent/AR221676A1/es active
- 1975-06-30 ZA ZA00754167A patent/ZA754167B/xx unknown
- 1975-06-30 IE IE1448/75A patent/IE41421B1/en unknown
- 1975-07-02 FR FR7520778A patent/FR2277590A1/fr active Granted
- 1975-07-03 NZ NZ178014A patent/NZ178014A/xx unknown
- 1975-07-03 FI FI751946A patent/FI63037C/fi not_active IP Right Cessation
- 1975-07-07 IL IL47656A patent/IL47656A/xx unknown
- 1975-07-07 AT AT0521275A patent/AT366064B/de not_active IP Right Cessation
- 1975-07-09 US US05/594,601 patent/US4057686A/en not_active Expired - Lifetime
- 1975-07-09 YU YU1744/75A patent/YU39271B/xx unknown
- 1975-07-09 HU HUEE2357A patent/HU170264B/hu unknown
- 1975-07-10 GB GB28984/75A patent/GB1506640A/en not_active Expired
- 1975-07-10 CA CA231,185A patent/CA1057681A/en not_active Expired
- 1975-07-10 DE DE19752530898 patent/DE2530898A1/de active Granted
- 1975-07-11 AU AU82959/75A patent/AU498365B2/en not_active Expired
- 1975-07-11 NO NO752499A patent/NO142175C/no unknown
- 1975-07-11 DK DK315375A patent/DK144946C/da not_active IP Right Cessation
- 1975-07-11 ES ES439316A patent/ES439316A1/es not_active Expired
- 1975-07-11 SU SU752152821A patent/SU676169A3/ru active
- 1975-07-11 RO RO7582833A patent/RO77525A/ro unknown
- 1975-07-11 SE SE7507966A patent/SE420204B/xx not_active IP Right Cessation
- 1975-07-11 BE BE158248A patent/BE831310A/xx not_active IP Right Cessation
- 1975-07-11 CH CH913575A patent/CH606085A5/xx not_active IP Right Cessation
- 1975-07-11 NL NLAANVRAGE7508316,A patent/NL171987C/xx not_active IP Right Cessation
- 1975-07-11 DD DD187262A patent/DD118643A5/xx unknown
- 1975-07-11 JP JP50085200A patent/JPS51125717A/ja active Granted
- 1975-07-12 PL PL1975182042A patent/PL94268B1/pl unknown
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