CH460746A - Verfahren zur Herstellung von neuen Menadoniumbisulfitderivaten mit Vitamin-K-Aktivität - Google Patents
Verfahren zur Herstellung von neuen Menadoniumbisulfitderivaten mit Vitamin-K-AktivitätInfo
- Publication number
- CH460746A CH460746A CH1364863A CH1364863A CH460746A CH 460746 A CH460746 A CH 460746A CH 1364863 A CH1364863 A CH 1364863A CH 1364863 A CH1364863 A CH 1364863A CH 460746 A CH460746 A CH 460746A
- Authority
- CH
- Switzerland
- Prior art keywords
- menadonium
- bisulfite
- water
- solution
- derivatives
- Prior art date
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 13
- 229930003448 Vitamin K Natural products 0.000 title claims description 5
- 230000000694 effects Effects 0.000 title claims description 5
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 235000019168 vitamin K Nutrition 0.000 title claims description 5
- 239000011712 vitamin K Substances 0.000 title claims description 5
- 150000003721 vitamin K derivatives Chemical class 0.000 title claims description 5
- 229940046010 vitamin k Drugs 0.000 title claims description 5
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- WHEQVHAIRSPYDK-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidin-2-one Chemical compound CC1=CC(C)=NC(O)=N1 WHEQVHAIRSPYDK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 150000003230 pyrimidines Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 17
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 14
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- QJQRNDGUWQVAEV-AAFSJPGBSA-M sodium bisulfite adduct Chemical compound [Na+].[O-]S(=O)(=O)C([C@H]1N(C(C2=C3)=O)C=C(C1)/C=C/C(=O)N(C)C)NC2=CC1=C3OCO1 QJQRNDGUWQVAEV-AAFSJPGBSA-M 0.000 description 3
- 230000002364 anti-haemorrhagic effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 description 1
- IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 description 1
- YOIOYCBMYHBCSY-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidin-2-one;sulfuric acid Chemical compound OS(O)(=O)=O.CC=1C=C(C)NC(=O)N=1 YOIOYCBMYHBCSY-UHFFFAOYSA-N 0.000 description 1
- UJVJGYQUOOQTAW-UHFFFAOYSA-N Pyrimine Natural products OC(=O)C1CCC(C=2N=CC=CC=2)=N1 UJVJGYQUOOQTAW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
- C07C50/14—Quinones the quinoid structure being part of a condensed ring system containing two rings with unsaturation outside the ring system, e.g. vitamin K1
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL62285292A NL143128B (nl) | 1962-11-09 | 1962-11-09 | Werkwijze voor het bereiden van een zout van een organische base en menadionbisulfiet, alsmede werkwijze ter bereiding van een veterinair preparaat onder toepassing van een aldus bereid zout. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH460746A true CH460746A (de) | 1968-08-15 |
Family
ID=19754215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1364863A CH460746A (de) | 1962-11-09 | 1963-11-07 | Verfahren zur Herstellung von neuen Menadoniumbisulfitderivaten mit Vitamin-K-Aktivität |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3328169A (en:Method) |
| AT (1) | AT251206B (en:Method) |
| CH (1) | CH460746A (en:Method) |
| DE (1) | DE1470128A1 (en:Method) |
| DK (1) | DK136607B (en:Method) |
| ES (1) | ES292681A1 (en:Method) |
| FR (1) | FR1558903A (en:Method) |
| GB (1) | GB1002503A (en:Method) |
| NL (1) | NL143128B (en:Method) |
| SE (1) | SE316757B (en:Method) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940491A (en) * | 1975-04-25 | 1976-02-24 | Abbott Laboratories | Bacterial source of vitamin K for animal feeds |
| IT1097391B (it) * | 1978-07-21 | 1985-08-31 | Stoppani Luigi Spa | Addotti di composti vitaminici del tipo k e vitamine stabilizzanti,loro preparazione e addotti stabilizzati cosi' ottenuti |
| DE3443270A1 (de) * | 1984-11-28 | 1986-05-28 | Basf Ag, 6700 Ludwigshafen | Menadioncholinbisulfit-addukt und verfahren zu dessen herstellung |
| US4808602A (en) * | 1986-02-27 | 1989-02-28 | Heterochemical Corporation | Derivatives based upon pyrido-menadione adducts and use thereof as feed premixes |
| US6596064B2 (en) | 1999-10-15 | 2003-07-22 | Luigi Stoppani S.P.A. | Biocidal-antifouling agents with low ecotoxicity index |
| ITMI20040679A1 (it) * | 2004-04-05 | 2004-07-05 | Vanetta Spa | Composto con attivita' vitaminica k particolarmente come additivo per mangimi e sua preparazione |
| EP2243765A1 (en) | 2009-04-21 | 2010-10-27 | Lonza Ltd. | Recovery of vitamin K3 mother liquor |
| EP2281465A1 (en) | 2009-08-05 | 2011-02-09 | Lonza Ltd. | Vitamin K3 derivative / NSA formulation |
| ITMI20100497A1 (it) | 2010-03-25 | 2011-09-26 | Prodotti Arca S R L | Utilizzo di menadione e derivati per il trattamento di biomasse. |
| CN108558775A (zh) * | 2018-06-07 | 2018-09-21 | 山东华升化工科技有限公司 | 一种二甲基嘧啶醇亚硫酸甲萘醌的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2367302A (en) * | 1940-03-25 | 1945-01-16 | Abbott Lab | Bisulphite derivatives of 2-methyl-1, 4-naphthoquinone and the like |
| US2385365A (en) * | 1943-02-17 | 1945-09-25 | Wisconsin Alumni Res Found | Salicylic acid compounds for safer therapeutic use |
| US2827377A (en) * | 1953-09-02 | 1958-03-18 | Abbott Lab | Animal feed composition |
| US3079260A (en) * | 1959-10-12 | 1963-02-26 | Galler William | Vitamin k animal feed premix |
| US3079261A (en) * | 1960-04-11 | 1963-02-26 | Heterochemical Corp | Vitamin k premix |
| US3196018A (en) * | 1960-08-08 | 1965-07-20 | Galler William | Coated menadione bisulfite adduct |
-
1962
- 1962-11-09 NL NL62285292A patent/NL143128B/xx not_active IP Right Cessation
-
1963
- 1963-01-31 DE DE19631470128 patent/DE1470128A1/de active Pending
- 1963-10-03 DK DK464563AA patent/DK136607B/da unknown
- 1963-10-09 GB GB39763/63A patent/GB1002503A/en not_active Expired
- 1963-10-19 ES ES0292681A patent/ES292681A1/es not_active Expired
- 1963-10-24 US US318516A patent/US3328169A/en not_active Expired - Lifetime
- 1963-10-28 AT AT858363A patent/AT251206B/de active
- 1963-11-07 CH CH1364863A patent/CH460746A/de unknown
- 1963-11-08 FR FR1558903D patent/FR1558903A/fr not_active Expired
- 1963-11-08 SE SE12357/63A patent/SE316757B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1470128A1 (de) | 1969-05-29 |
| FR1558903A (en:Method) | 1969-03-07 |
| GB1002503A (en) | 1965-08-25 |
| DK136607B (da) | 1977-10-31 |
| US3328169A (en) | 1967-06-27 |
| NL143128B (nl) | 1974-09-16 |
| SE316757B (en:Method) | 1969-11-03 |
| DK136607C (en:Method) | 1978-04-03 |
| ES292681A1 (es) | 1964-04-01 |
| AT251206B (de) | 1966-12-27 |
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