DE1620529C - Process for the preparation of 2 (3 hydroxy 5 hydroxymethyl 2 methyl 4 pyridyl) tetrahydro 1,3 thiazine 4 carboxylic acid - Google Patents
Process for the preparation of 2 (3 hydroxy 5 hydroxymethyl 2 methyl 4 pyridyl) tetrahydro 1,3 thiazine 4 carboxylic acidInfo
- Publication number
- DE1620529C DE1620529C DE1620529C DE 1620529 C DE1620529 C DE 1620529C DE 1620529 C DE1620529 C DE 1620529C
- Authority
- DE
- Germany
- Prior art keywords
- pyridyl
- methyl
- hydroxy
- tetrahydro
- hydroxymethyl
- 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
- ZLIAWSCQKUNLSI-UHFFFAOYSA-N 2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]-1,3-thiazinane-4-carboxylic acid Chemical compound CC1=NC=C(CO)C(C2SCCC(N2)C(O)=O)=C1O ZLIAWSCQKUNLSI-UHFFFAOYSA-N 0.000 title 1
- 239000000243 solution Substances 0.000 claims description 9
- KWIUHFFTVRNATP-UHFFFAOYSA-N Trimethylglycine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 6
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 229960003581 Pyridoxal Drugs 0.000 claims description 3
- 229960003237 betaine Drugs 0.000 claims description 3
- 235000008164 pyridoxal Nutrition 0.000 claims description 3
- 239000011674 pyridoxal Substances 0.000 claims description 3
- -1 5 - hydroxymethyl - 2 - methyl - 4 - pyridyl Chemical group 0.000 claims description 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 2
- KIWQWJKWBHZMDT-VKHMYHEASA-N L-homocysteine thiolactone Chemical compound N[C@H]1CCSC1=O KIWQWJKWBHZMDT-VKHMYHEASA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
- FCHXJFJNDJXENQ-UHFFFAOYSA-N 3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-1-ium-4-carbaldehyde;chloride Chemical compound Cl.CC1=NC=C(CO)C(C=O)=C1O FCHXJFJNDJXENQ-UHFFFAOYSA-N 0.000 description 3
- 229960001734 Sulfobromophthalein Drugs 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OHTXTCNTQJFRIG-UHFFFAOYSA-N bromosulfophthalein Chemical compound C1=C(S(O)(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S(O)(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 OHTXTCNTQJFRIG-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 210000000941 Bile Anatomy 0.000 description 2
- FFFHZYDWPBMWHY-UHFFFAOYSA-N DL-homocysteine Chemical compound OC(=O)C(N)CCS FFFHZYDWPBMWHY-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229960001327 Pyridoxal Phosphate Drugs 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229930003270 Vitamin B Natural products 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 2
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 2
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 2
- 235000008160 pyridoxine Nutrition 0.000 description 2
- 239000011677 pyridoxine Substances 0.000 description 2
- 229960002862 pyridoxine Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000019156 vitamin B Nutrition 0.000 description 2
- 239000011720 vitamin B Substances 0.000 description 2
- IMXQQJJGZSVVOP-UHFFFAOYSA-N 3-hydroxy-5-(hydroxymethyl)-2-methyl-1-oxidopyridin-1-ium-4-carbaldehyde Chemical compound CC1=C(O)C(C=O)=C(CO)C=[N+]1[O-] IMXQQJJGZSVVOP-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 230000036826 Excretion Effects 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 210000004185 Liver Anatomy 0.000 description 1
- 229960004172 Pyridoxine Hydrochloride Drugs 0.000 description 1
- 229940087562 Sodium Acetate Trihydrate Drugs 0.000 description 1
- 229940088594 Vitamin Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- DETXZQGDWUJKMO-UHFFFAOYSA-N hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- AYRVGWHSXIMRAB-UHFFFAOYSA-M sodium acetate trihydrate Chemical compound O.O.O.[Na+].CC([O-])=O AYRVGWHSXIMRAB-UHFFFAOYSA-M 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229930003231 vitamins Natural products 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Description
Fs wurde gefunden, daß 2-(3-Hydroxy-5-hydroxyinetliyl - 2 - methyl - 4 - pyridyl) - tetrahydro - 1 ,J - thiazin-4-carbonsäure im Tierversuch eine überlegene Lebcrschutzwirkung aufweist.It has been found that 2- (3-hydroxy-5-hydroxyinetliyl - 2 - methyl - 4 - pyridyl) - tetrahydro - 1, J - thiazine-4-carboxylic acid Has a superior liver protection effect in animal experiments.
Die in Tabelle I zum Vergleich aufgeführten Vitamin Be-Derivate wurden oral 200 bis 250 g schweren männlichen Wister-King-Raüen verabfolgt; die Dosen waren einer Menge von 5 mg Pyridoxal-hydrochlorid pro kg und Tag iiqiiimolar. Applikationsdauer: 5Tage. The vitamin B e derivatives listed in Table I for comparison were administered orally to male Wister-King dogs weighing 200 to 250 g; the doses were an amount of 5 mg pyridoxal hydrochloride per kg and day iiqiiimolar. Application time: 5 days.
Jeder Ratte wurden dann 0,5 mg/kg Tetrachlorkohlenstoff als l()°/oige Lösung in Olivenöl subkutan' injiziert. Nach einer Mungerzeit von 30 Stunden wurden 25 mg/kg Bromsulphalein den Ratten intravenös injiziert. Die Ausscheidung von Bromsulphalein in die Galle wurde beobachtet.Each rat was then injected with 0.5 mg / kg of carbon tetrachloride as l () ° / o solution in olive oil subcutaneously '. After a munging period of 30 hours, 25 mg / kg of bromosulphalin was injected intravenously into the rats. The excretion of bromosulphalein in the bile was observed.
Der Prozentsatz des in die Galle ausgeschiedenen. Bromsulphaleins im Verhältnis zum injizierten Bromsulphalein ist jeweils in Tabelle I wiedergegeben.The percentage of it excreted in the bile. Bromosulphalein in relation to the injected bromosulphalein is shown in Table I in each case.
Vitamin B„-[)erivatVitamin B "- [) derivative
Anzahl der
Rallennumber of
Rallen
.10 Minuten.10 mins
Zeit nach der Uronisulphalein-Injcklion
45 Minuten | !Stunde I1/, Stunden I 2 StundenTime after uronisulphalein injection
45 minutes | ! Hour I 1 /, hours I 2 hours
Mit Tetrachlorkohlenstoff behandeltTreated with carbon tetrachloride
Pyridoxal-ni.-honioeystein-Pyridoxal-ni.-honioeystein-
Kondensat der lirfiiidung Condensate of the fluid
Pyridoxalhydrochlorid Pyridoxal hydrochloride
Homocystcin Homocystcin
ohne Derivat without derivative
Unbehandelt Untreated
5
4
5
55
4th
5
5
24,0
23,0
23,5
23,024.0
23.0
23.5
23.0
25,025.0
46,0
41,0
40,0
37,046.0
41.0
40.0
37.0
45,545.5
55,0
60,5
50,555.0
60.5
50.5
66,066.0
76,3
70,5
72,3
62,076.3
70.5
72.3
62.0
80,680.6
90,5
80,0
80,0
78,090.5
80.0
80.0
78.0
02,502.5
Die akute Toxi/ität der erlinriungsgcmäBen Verbindung bei Mäusen ist nach Tabelle Il erheblich geringer als die von Pyridoxalphosphat und Pyridoxin-hydrodilorid.According to Table II, the acute toxicity of the elucidating compound in mice is considerably lower than those of pyridoxal phosphate and pyridoxine hydrodiloride.
470)270)
470)
subkutanI. n ", (mg / kg)
subcutaneous
240 (210 bis
400 (340 bis> 1500
240 (210 to
400 (340 to
550 (380 bis 700)
1900 (1710 bis 2130)3005 (2550 to 35410)
550 (380 to 700)
1900 (1710 to 2130)
>3000
>3000about 10,000
> 3000
> 3000
Pyridoxal-phosphat l'yiiiloxal-Di.-hoinocysteine condensate
Pyridoxal phosphate
Die 2 - (3 - Hydroxy - 5 - hydroxymethyl - 2 - me-Ihyl -4- pyridyl)- tetrahydro-1,3 -Ihia/in-4-carbonsäure wird dadurch hergestellt, daI3 in an sich bekannter Weise Pyridoxal oder eines seiner Salze oder das Betain der ('.1 - Hydroxy - 5 - hydroxymethyl - 2 - methyl - 4 - pyridyl)-hydroxymethansulfosäure in wäßriger Lösung mit Homocystein, das gegebenenfalls aus einem Salz des Homocystein-thiolactons in alkalischer Lösung hergestellt worden ist, umgesetzt wird.The 2 - (3 - hydroxy - 5 - hydroxymethyl - 2 - methyl -4-pyridyl) - tetrahydro-1,3-ihia / yn-4-carboxylic acid is produced by adding pyridoxal or one of its salts or betaine in a manner known per se of ('.1 - Hydroxy - 5 - hydroxymethyl - 2 - methyl - 4 - pyridyl) hydroxymethanesulfonic acid in aqueous solution with homocysteine, which optionally consists of a salt of homocysteine thiolactone has been prepared in alkaline solution, is reacted.
Der Reaktion entspricht folgende Gleichung:The reaction corresponds to the following equation:
OHOH
CHOCHO
CH,
HS-CH1CHjCH-COOH NCH,
HS-CH 1 CHjCH-COOH N
NH, .NH,.
OHOH
(U)(U)
Aulkr dem Detain der (3-Hydroxy-i-liydroxy-nie-1 hy 1 - 2 - methyl - 4 - pyridyl) - hydroxymethaiiitilfonsäure oder den Sulzen de> Pyridoxal· kann auch ein Oxydalionsgemisch von Pyridoxin oder das Reaktionsgemisch von Pyridoxaloxiiu mit salpetriger Siiure al·; Aingangsmalerial verwendet werden. Min liiQl da; Re.iklion->gemiich längen; Zeit bei Zimmer temperatur sklicn, Wi)Ia-I vor/m,;iAcise ein pll-Wei t von etwa I bi; 5 L'in|',i:h.ilii:ii wird. Wild als Ausgangsnialnial ein SaI/. de1; llomocysleiii-thiolaitoiiü verwendet, ι. Ii. das Hydrodiloiid. ;t> wird die· in alkalischer Lösung, /.. FJ in wallrii1,·ι Natronlauge oder Kalilauge vorzugsweise bi i ftw;i 30 bis 4l)°C unter einer indifferenten HN-<In addition to the detail of (3-hydroxy-i-liydroxy-nie-1 hy 1 - 2 - methyl - 4 - pyridyl) - hydroxymethaiitilfonic acid or the sulzenes of> pyridoxal, an oxidation mixture of pyridoxine or the reaction mixture of pyridoxaloxide with nitrous acid can also be used al ·; Entrance materials are used. Min liiQl there; Re.iklion->lengthen; Time at room temperature sklicn, Wi) Ia-I before / m,; iAcise a pll-width of about I bi; 5 L'in | ', i: h.ilii: ii will. Wild a SaI / as the starting event. de 1 ; llomocysleiii-thiolaitoiiü used, ι. Ii. the hydrodiloid. ; t> the · in alkaline solution, / .. FJ in wallrii 1 , · ι sodium hydroxide solution or potassium hydroxide solution preferably up to 30 to 41 ° C under an indifferent HN- <
CH2OH COOHCH 2 OH COOH
(HI)(HI)
5555
fiufiu
Das Endproilukt (HI) kann auf übliche Weise aus dem Reaklionsgeinisch gewonnen werden. Beispielsweise'kann es durch Abkühlen des Reaktionsgemische« hei schwach sauren Bedingungen leicht zum Auskristallisieren gebracht werden.The end product (HI) can be made in the usual way can be won the Reaklionsgeinisch. For example, 'can it is easy to crystallize out by cooling the reaction mixture under mildly acidic conditions to be brought.
2,03 g P/iiilonal-hydrodilorid, 1,35 g »i.-IIonio· cystein und '2,72 ι; rlatriuinacetat-lrihydrat wurden in 8 ml Wasser unter firwilriiiiMi gelöst. Mach dem nitrieren des Cl.riiiisclic» .wurde da» luhalten-i l;illrat 1 Stunde bei 'Zimmertemperatur iiuliengd.iüi:n, wobei2.03 g of P / iiilonal hydrodiloride, 1.35 g of i-ionio · cysteine and 2.72 ι; rlatriuinacetat-lrihydrat were dissolved in 8 ml of water under firwilriiiiMi. Do the nitriding of the Cl.riiiisclic ».was da» luhalten-i l ; illrat 1 hour at room temperature iiuliengd.iüi: n, where
f.,M.,-.. ΝΓ,-ιΛι-Ιη η 11 ·; V τ t s I 111 i s 1 e Γ t C T>.f., M., - .. ΝΓ, -ιΛι-Ιη η 11 ·; V τ t s I 111 i s 1 e Γ t C T>.
Die abgeschiedenen Kristalle wurden durch Filtration abgetrennt. Die Mutterlauge wurde eingeengt, wodurch weitere Kristalle erhalten wurden. Sie wurden mit den zuerst gewonnenen vereinigt, nacheinander mit' kaltem Wasser und Aceton gewaschen und getrocknet. Fp. 152 bis 153°C (Zersetzung), Ausbeute: 2,3 g, entsprechend 76%.The deposited crystals were separated by filtration. The mother liquor was concentrated, whereby more crystals were obtained. They were united with those won first, one after the other with ' washed in cold water and acetone and dried. Mp. 152 to 153 ° C. (decomposition), yield: 2.3 g, correspondingly 76%.
Infrarot-Absorptionsmaxima (in Nujol):Infrared absorption maxima (in Nujol):
3250, 2000 bis 2700, 1732, 1635, 1610, 1590, 1520, 1460 und 1410 cm-1.3250, 2000 to 2700, 1732, 1635, 1610, 1590, 1520, 1460 and 1410 cm- 1 .
Ultraviolett-Absorptionsmaxima (in Wasser bei pH 7,5):Ultraviolet absorption maxima (in water at pH 7.5):
324, 253 und 222 πιμ.324, 253 and 222 πιμ.
Magnetischer Kernresonanzwert (in Dimethylsulfoxid): Nuclear magnetic resonance value (in dimethyl sulfoxide):
2,05 r (Pyridin <x — H),2.05 r (pyridine <x - H),
4,46r(Thiazin2 —H).4.46r (Thiazine2-H).
2,5 g Betain der P-Hydroxy-S-hydroxymethyW-methyl-4-pyridyl)-hydroxymethansulfonsäure, 1,35 dl-Homocystein und 2,72 g Natriumacetattrihydrat wurden in 6 ml Wasser gelöst. Das Gemisch wurde 1 Stunde in der Eiskiste stehengelassen, wobei farblose Nadeln auskristallisierten.2.5 g betaine of P-hydroxy-S-hydroxymethyW-methyl-4-pyridyl) -hydroxymethanesulfonic acid, 1.35 dl homocysteine and 2.72 g sodium acetate trihydrate were dissolved in 6 ml water. The mixture was 1 hour Left to stand in the ice box, colorless needles crystallized out.
Die Kristalle wurden abfiltriert und nacheinander mit kaltem Wasser und Aceton gewaschen. Fp. 152 bis 1530C (Zersetzung), Ausbeute: 2,15g, entsprechend 71%.The crystals were filtered off and washed successively with cold water and acetone. Mp 152-153 0 C (decomposition). Yield: 2.15 g, corresponding to 71%.
Die Absorptionsmaxima im Infrarot und Ultraviolett und die Werte für die magnetische Kernresonanz des Produktes waren mit denen der Verbindung des Beispiels 1 identisch.The absorption maxima in the infrared and ultraviolet and the values for the nuclear magnetic resonance of the product were identical to those of the compound of Example 1.
63 g 95%iges Natriumhydroxyd wurden in 380 ml Wasser gelöst und 77 g DL-Homocystein-thioIactonhydrochlorid unter Stickstoff bei 30 bis 400C zu der Lösung zugesetzt. Man ließ 30 Minuten bei Zimmertemperatur stehen und setzte 60 g Essigsäure und 102 g ίο Pyridoxal-hydrochlorid zu der Lösung zu. Das Ge-■ misch wurde 30 Minuten gerührt und die erhaltene klare, orangefarbene Lösung 4 Stunden unter Kühlung stehengelassen, wobei , 107,7 g feine Nadeln auskristallisierten. 63 g of 95% sodium hydroxide were dissolved in 380 ml of water and 77 g of DL-homocysteine thioIactonhydrochlorid under nitrogen at 30 to 40 0 C is added to the solution. The mixture was left to stand for 30 minutes at room temperature and 60 g of acetic acid and 102 g of pyridoxal hydrochloride were added to the solution. The mixture was stirred for 30 minutes and the clear, orange-colored solution obtained was allowed to stand for 4 hours with cooling, 107.7 g of fine needles crystallizing out.
Ausbeute: 75%Yield: 75%
Die Kristalle wurden aus Wasser umkristallisiert,The crystals were recrystallized from water,
mit Aceton gewaschen und bei vermindertem Druck über Phosphorpentoxid bei 500C getrocknet. Fp. 135washed with acetone and dried over phosphorus pentoxide at 50 ° C. under reduced pressure. M.p. 135
ao bis 138°C (Zersetzung), Ausbeute: 63,5 g entsprechend 44%.ao to 138 ° C (decomposition), yield: 63.5 g accordingly 44%.
Claims (1)
Family
ID=
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