SE446864B - Disulfidforeningar, forfaranden for framstellning derav samt farmaceutisk komposition innehallande nemnda disulfidforeningar som aktiv komponent - Google Patents

Disulfidforeningar, forfaranden for framstellning derav samt farmaceutisk komposition innehallande nemnda disulfidforeningar som aktiv komponent

Info

Publication number: SE446864B
Authority: SE; Sweden
Prior art keywords: compound; formula; acid; low; denotes
Prior art date: 1978-12-30

Application number

SE7910554A

Other languages

English (en)

Swedish (sv)

Other versions

SE7910554L (sv

Inventor

J-I Iwao

M Oya

T Iso

Original Assignee

Santen Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1978-12-30

Filing date

1979-12-20

Publication date

1986-10-13

1978-12-30 Priority claimed from JP53163964A external-priority patent/JPS6048511B2/ja

1979-01-29 Priority claimed from JP939279A external-priority patent/JPS55102560A/ja

1979-03-17 Priority claimed from JP3133479A external-priority patent/JPS55124757A/ja

1979-06-26 Priority claimed from JP8104379A external-priority patent/JPS565415A/ja

1979-07-03 Priority claimed from JP8482779A external-priority patent/JPS568317A/ja

1979-12-20 Application filed by Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd

1980-07-01 Publication of SE7910554L publication Critical patent/SE7910554L/xx

1986-10-13 Publication of SE446864B publication Critical patent/SE446864B/sv

Links

238000000034 method Methods 0.000 title claims abstract description 35
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
150000002019 disulfides Chemical class 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 139
-1 amino, phenoxy Chemical group 0.000 claims abstract description 132
125000000217 alkyl group Chemical group 0.000 claims abstract description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 7
208000002249 Diabetes Complications Diseases 0.000 claims abstract description 5
206010012655 Diabetic complications Diseases 0.000 claims abstract description 5
125000002541 furyl group Chemical group 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
230000036772 blood pressure Effects 0.000 claims abstract description 4
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 7
239000001257 hydrogen Substances 0.000 claims abstract 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
125000001624 naphthyl group Chemical group 0.000 claims abstract 3
125000001544 thienyl group Chemical group 0.000 claims abstract 3
150000002431 hydrogen Chemical class 0.000 claims abstract 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
239000002253 acid Substances 0.000 claims description 49
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 15
LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229950001139 timonacic Drugs 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
208000002177 Cataract Diseases 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 2
206010012601 diabetes mellitus Diseases 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
AZDYQBFYMBALBY-UHFFFAOYSA-N 2-phenyl-1,3-thiazolidin-3-ium-4-carboxylate Chemical compound N1C(C(=O)O)CSC1C1=CC=CC=C1 AZDYQBFYMBALBY-UHFFFAOYSA-N 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
208000017442 Retinal disease Diseases 0.000 claims 1
206010038923 Retinopathy Diseases 0.000 claims 1
241000347391 Umbrina cirrosa Species 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000005530 alkylenedioxy group Chemical group 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
208000017169 kidney disease Diseases 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
201000001119 neuropathy Diseases 0.000 claims 1
230000007823 neuropathy Effects 0.000 claims 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
208000033808 peripheral neuropathy Diseases 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
125000004076 pyridyl group Chemical group 0.000 abstract 2
239000005864 Sulphur Substances 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 59
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000007864 aqueous solution Substances 0.000 description 23
239000000047 product Substances 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 20
239000013078 crystal Substances 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 15
239000008101 lactose Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
229940125904 compound 1 Drugs 0.000 description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000003513 alkali Substances 0.000 description 10
239000012267 brine Substances 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
102000016912 Aldehyde Reductase Human genes 0.000 description 9
108010053754 Aldehyde reductase Proteins 0.000 description 9
241001446467 Mama Species 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
239000001913 cellulose Substances 0.000 description 8
229920002678 cellulose Polymers 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
239000000155 melt Substances 0.000 description 8
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239000000843 powder Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
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239000011575 calcium Substances 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
229920002134 Carboxymethyl cellulose Polymers 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
239000001768 carboxy methyl cellulose Substances 0.000 description 6
235000010948 carboxy methyl cellulose Nutrition 0.000 description 6
239000008112 carboxymethyl-cellulose Substances 0.000 description 6
239000008119 colloidal silica Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000005457 ice water Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 5
230000009471 action Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
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150000007530 organic bases Chemical class 0.000 description 5
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238000012360 testing method Methods 0.000 description 5
101800000734 Angiotensin-1 Proteins 0.000 description 4
102400000344 Angiotensin-1 Human genes 0.000 description 4
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
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229920002472 Starch Polymers 0.000 description 4
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 4
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125000000107 disulfanyl group Chemical group [*]SS[H] 0.000 description 4
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239000008107 starch Substances 0.000 description 4
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
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KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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238000007254 oxidation reaction Methods 0.000 description 3
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
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229940126540 compound 41 Drugs 0.000 description 1
229940127271 compound 49 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
229960003067 cystine Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
208000033679 diabetic kidney disease Diseases 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
150000005332 diethylamines Chemical class 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
125000002228 disulfide group Chemical group 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960003883 furosemide Drugs 0.000 description 1
FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002402 hexoses Chemical class 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000005555 hypertensive agent Substances 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
229950008838 indenolol Drugs 0.000 description 1
MPGBPFMOOXKQRX-UHFFFAOYSA-N indenolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CC2 MPGBPFMOOXKQRX-UHFFFAOYSA-N 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VOWZDEHCXOBDME-UHFFFAOYSA-N methyl chlorosulfinylformate Chemical compound COC(=O)S(Cl)=O VOWZDEHCXOBDME-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
101150007570 nra-1 gene Proteins 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
229960004570 oxprenolol Drugs 0.000 description 1
235000020636 oyster Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000008188 pellet Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
235000021110 pickles Nutrition 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229940020414 potassium triiodide Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
OEKUVLQNKPXSOY-UHFFFAOYSA-N quercetin 3-O-beta-D-glucopyranosyl(1->3)-alpha-L-rhamnopyranosyl(1->6)-beta-d-galactopyranoside Natural products OC1C(O)C(C(O)C)OC1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OEKUVLQNKPXSOY-UHFFFAOYSA-N 0.000 description 1
QPHXPNUXTNHJOF-UHFFFAOYSA-N quercetin-7-O-beta-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 QPHXPNUXTNHJOF-UHFFFAOYSA-N 0.000 description 1
OXGUCUVFOIWWQJ-HQBVPOQASA-N quercitrin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-HQBVPOQASA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
238000011160 research Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
GJNRIGCZVXQSHN-UHFFFAOYSA-M sodium;oxido-oxo-propoxy-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CCCOS([O-])(=O)=S GJNRIGCZVXQSHN-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
HDFRDWFLWVCOGP-UHFFFAOYSA-M sulfanylformate Chemical compound [O-]C(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-M 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 1
229960004605 timolol Drugs 0.000 description 1
229960004402 tiopronin Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SE7910554A 1978-12-30 1979-12-20 Disulfidforeningar, forfaranden for framstellning derav samt farmaceutisk komposition innehallande nemnda disulfidforeningar som aktiv komponent SE446864B (sv)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP53163964A JPS6048511B2 (ja)	1978-12-30	1978-12-30	ジスルフイド化合物
JP939279A JPS55102560A (en)	1979-01-29	1979-01-29	Disulfide compound
JP3133479A JPS55124757A (en)	1979-03-17	1979-03-17	Sulfur-containing compound
JP8104379A JPS565415A (en)	1979-06-26	1979-06-26	Ester-type hypotensor
JP8482779A JPS568317A (en)	1979-07-03	1979-07-03	Preventive and remedy for complicating disease of diabetes mellitus

Publications (2)

Publication Number	Publication Date
SE7910554L SE7910554L (sv)	1980-07-01
SE446864B true SE446864B (sv)	1986-10-13

Family

ID=27519061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7910554A SE446864B (sv)	1978-12-30	1979-12-20	Disulfidforeningar, forfaranden for framstellning derav samt farmaceutisk komposition innehallande nemnda disulfidforeningar som aktiv komponent

Country Status (10)

Country	Link
US (1)	US4347371A (it)
AU (1)	AU536307B2 (it)
CA (1)	CA1128517A (it)
CH (1)	CH647769A5 (it)
DE (1)	DE2952594A1 (it)
FR (1)	FR2445324A1 (it)
GB (1)	GB2042517B (it)
IT (1)	IT1127323B (it)
NL (1)	NL7909334A (it)
SE (1)	SE446864B (it)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU528115B2 (en) *	1978-04-08	1983-04-14	Santen Pharmaceutical Co. Ltd.	Antihypertensive 4-thiazolidine/carboxylic acids
US4499102A (en) *	1979-12-13	1985-02-12	Santen Pharmaceutical Co., Ltd.	Thiazolidine and pyrrolidine compounds and pharmaceutical compositions containing them
JPS5683483A (en) *	1979-12-13	1981-07-08	Santen Pharmaceut Co Ltd	Thiazolidine compound
DE3152643A1 (de) *	1980-12-29	1982-12-16	Santen Pharmaceutical Co Ltd	Heterocyclic 5-membered ring compounds
JPS57142962A (en) *	1981-02-28	1982-09-03	Santen Pharmaceut Co Ltd	Cyclodextrin clathrate compound of sulfur-containing compound
US5665770A (en) *	1993-11-05	1997-09-09	Gakko Hojin Kinki Daigaku	Method for treatment of cataract with radical scavenger
AU2002305744B2 (en) *	2001-05-30	2008-09-11	Yeda Research And Development Co. Ltd.	Allylmercaptocaptopril compounds and uses thereof
CA2610922A1 (en) *	2005-06-13	2006-12-21	Yeda Research And Development Co. Ltd.	Use of allylmercaptocaptopril for treating or preventing obesity and obesity related diseases
WO2007086054A2 (en) *	2006-01-25	2007-08-02	Yeda Research And Development Co. Ltd.	A process for preparing allylmercaptocaptopril (cpssa) and related asymmetrical disulfides
CN104945350A (zh) *	2014-03-25	2015-09-30	中国科学院生态环境研究中心	简捷合成高光学纯度噻唑氨基酸的新方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU509899B2 (en) *	1976-02-13	1980-05-29	E.R. Squibb & Sons, Inc.	Proline derivatives and related compounds
AU518147B2 (en) *	1976-12-03	1981-09-17	E.R. Squibb & Sons, Inc.	Derivatives of thiazolidine, thiazine and morpholine carboxylic acids
US4192878A (en) *	1976-12-03	1980-03-11	E. R. Squibb & Sons, Inc.	Derivatives of thiazolidinecarboxylic acids and related acids
JPS5834474B2 (ja) *	1977-06-29	1983-07-27	ウェルファイド株式会社	チアゾリジン誘導体の製造法
CA1102812A (en) *	1978-05-22	1981-06-09	Miguel A. Ondetti	Derivatives of thiazolidinecarboxylic acids and related acids
CA1144930A (en) *	1978-08-11	1983-04-19	Miguel A. Ondetti	Mercaptoacyl derivatives of substituted prolines

1979
- 1979-12-18 US US06/104,970 patent/US4347371A/en not_active Expired - Lifetime
- 1979-12-19 AU AU54024/79A patent/AU536307B2/en not_active Ceased
- 1979-12-20 SE SE7910554A patent/SE446864B/sv not_active IP Right Cessation
- 1979-12-20 CA CA342,420A patent/CA1128517A/en not_active Expired
- 1979-12-28 GB GB7944544A patent/GB2042517B/en not_active Expired
- 1979-12-28 IT IT28440/79A patent/IT1127323B/it active
- 1979-12-28 DE DE19792952594 patent/DE2952594A1/de not_active Withdrawn
- 1979-12-28 CH CH11528/79A patent/CH647769A5/de not_active IP Right Cessation
- 1979-12-28 NL NL7909334A patent/NL7909334A/nl not_active Application Discontinuation
- 1979-12-28 FR FR7932060A patent/FR2445324A1/fr active Granted

Also Published As

Publication number	Publication date
FR2445324A1 (fr)	1980-07-25
AU536307B2 (en)	1984-05-03
AU5402479A (en)	1980-07-03
US4347371A (en)	1982-08-31
DE2952594A1 (de)	1980-07-17
NL7909334A (nl)	1980-07-02
SE7910554L (sv)	1980-07-01
CH647769A5 (de)	1985-02-15
GB2042517B (en)	1983-05-25
IT1127323B (it)	1986-05-21
IT7928440A0 (it)	1979-12-28
CA1128517A (en)	1982-07-27
GB2042517A (en)	1980-09-24
FR2445324B1 (it)	1984-03-09

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