FI61881C - Foerfarande foer framstaellning av farmaceutiskt anvaendbara alkansulfonater av 2-metyl-3-hydroxi-4-hydroximetyl-5-merkaptometylpyridin - Google Patents
Foerfarande foer framstaellning av farmaceutiskt anvaendbara alkansulfonater av 2-metyl-3-hydroxi-4-hydroximetyl-5-merkaptometylpyridin Download PDFInfo
- Publication number
- FI61881C FI61881C FI761084A FI761084A FI61881C FI 61881 C FI61881 C FI 61881C FI 761084 A FI761084 A FI 761084A FI 761084 A FI761084 A FI 761084A FI 61881 C FI61881 C FI 61881C
- Authority
- FI
- Finland
- Prior art keywords
- ethane
- methyl
- preparation
- treated
- bis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000003814 drug Substances 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 13
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkaline earth metal salt Chemical class 0.000 claims description 7
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims description 4
- JXYDRIBYAKJTIW-UHFFFAOYSA-N 4-(hydroxymethyl)-2-methyl-5-(sulfanylmethyl)pyridin-3-ol Chemical compound CC1=NC=C(CS)C(CO)=C1O JXYDRIBYAKJTIW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 2
- DTUGMSZQWAGQQP-UHFFFAOYSA-N C(CS(=O)(=O)O)S(=O)(=O)O.SC1(C(C(=C(N=C1)C)O)CO)CO.SC1(C(C(=C(N=C1)C)O)CO)CO Chemical compound C(CS(=O)(=O)O)S(=O)(=O)O.SC1(C(C(=C(N=C1)C)O)CO)CO.SC1(C(C(=C(N=C1)C)O)CO)CO DTUGMSZQWAGQQP-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- PZTHSDYEYQLIDM-UHFFFAOYSA-N 4-methoxy-2-methyl-5-methylsulfanylpyridin-3-ol Chemical compound COC1=C(O)C(C)=NC=C1SC PZTHSDYEYQLIDM-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KIIRCKJOQWLFED-UHFFFAOYSA-N ethane-1,2-disulfonate;4-(hydroxymethyl)-2-methyl-5-(sulfanylmethyl)pyridin-1-ium-3-ol Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O.CC1=[NH+]C=C(CS)C(CO)=C1O.CC1=[NH+]C=C(CS)C(CO)=C1O KIIRCKJOQWLFED-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 2
- YPRMPUCBNRXSEU-UHFFFAOYSA-N 4-(hydroxymethyl)-2-methyl-5-(sulfanylmethyl)pyridin-3-ol;hydrochloride Chemical compound Cl.CC1=NC=C(CS)C(CO)=C1O YPRMPUCBNRXSEU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ILOQMYUFDKXIRS-UHFFFAOYSA-N ethane-1,2-disulfonic acid;sodium Chemical compound [Na].[Na].OS(=O)(=O)CCS(O)(=O)=O ILOQMYUFDKXIRS-UHFFFAOYSA-N 0.000 description 1
- PDPYJBPAAQFXNF-UHFFFAOYSA-N ethane;sulfo hydrogen sulfate Chemical compound CC.OS(=O)(=O)OS(O)(=O)=O PDPYJBPAAQFXNF-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000000405 serological effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
- C07D213/67—2-Methyl-3-hydroxy-4,5-bis(hydroxy-methyl)pyridine, i.e. pyridoxine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57605575A | 1975-05-09 | 1975-05-09 | |
| US57605575 | 1975-05-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI761084A7 FI761084A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-10 |
| FI61881B FI61881B (fi) | 1982-06-30 |
| FI61881C true FI61881C (fi) | 1982-10-11 |
Family
ID=24302783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI761084A FI61881C (fi) | 1975-05-09 | 1976-04-21 | Foerfarande foer framstaellning av farmaceutiskt anvaendbara alkansulfonater av 2-metyl-3-hydroxi-4-hydroximetyl-5-merkaptometylpyridin |
Country Status (29)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695428C3 (de) * | 1967-06-08 | 1978-10-05 | Merck Patent Gmbh, 6100 Darmstadt | Derivate des 5-Mercaptopyridoxins und Verfahren zu deren Herstellung |
| US3852454A (en) * | 1973-06-15 | 1974-12-03 | Merck & Co Inc | Treatment of rheumatoid arthritis |
-
1976
- 1976-04-21 SE SE7604580A patent/SE427033B/xx not_active IP Right Cessation
- 1976-04-21 DK DK179376A patent/DK143335C/da not_active IP Right Cessation
- 1976-04-21 FI FI761084A patent/FI61881C/fi not_active IP Right Cessation
- 1976-04-22 NO NO761367A patent/NO144925C/no unknown
- 1976-04-22 NL NL7604285A patent/NL7604285A/xx not_active Application Discontinuation
- 1976-04-24 RO RO7685792A patent/RO68526A/ro unknown
- 1976-04-26 CH CH521976A patent/CH625222A5/de not_active IP Right Cessation
- 1976-04-26 IL IL49466A patent/IL49466A/xx unknown
- 1976-04-26 NZ NZ180691A patent/NZ180691A/xx unknown
- 1976-04-27 AR AR263046A patent/AR210883A1/es active
- 1976-04-28 AU AU13428/76A patent/AU1342876A/en not_active Expired
- 1976-04-29 GR GR50620A patent/GR59817B/el unknown
- 1976-04-30 PT PT65061A patent/PT65061B/pt unknown
- 1976-05-04 GB GB18196/76A patent/GB1490688A/en not_active Expired
- 1976-05-04 BG BG033100A patent/BG25218A3/xx unknown
- 1976-05-04 CA CA251,741A patent/CA1088542A/en not_active Expired
- 1976-05-05 FR FR7613351A patent/FR2310130A1/fr active Granted
- 1976-05-06 PL PL1976189342A patent/PL100306B1/pl unknown
- 1976-05-06 LU LU74892A patent/LU74892A1/xx unknown
- 1976-05-06 DD DD192709A patent/DD125482A5/xx unknown
- 1976-05-07 BE BE166849A patent/BE841593A/xx unknown
- 1976-05-07 DE DE2620325A patent/DE2620325C3/de not_active Expired
- 1976-05-07 CS CS763063A patent/CS189003B2/cs unknown
- 1976-05-07 AT AT335676A patent/AT348691B/de not_active IP Right Cessation
- 1976-05-07 ZA ZA762750A patent/ZA762750B/xx unknown
- 1976-05-07 IE IE990/76A patent/IE43030B1/en unknown
- 1976-05-07 HU HU76ME00001974A patent/HU172048B/hu unknown
- 1976-05-07 ES ES447717A patent/ES447717A1/es not_active Expired
- 1976-05-08 JP JP51051720A patent/JPS51138684A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: MERCK & CO., INC. |