BE634436A - - Google Patents
Info
- Publication number
- BE634436A BE634436A BE634436DA BE634436A BE 634436 A BE634436 A BE 634436A BE 634436D A BE634436D A BE 634436DA BE 634436 A BE634436 A BE 634436A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- general formula
- acid
- acid addition
- radical
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- 102000015636 Oligopeptides Human genes 0.000 claims 1
- 108010038807 Oligopeptides Proteins 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000001012 protector Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- -1 chlor- Chemical class 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<EMI ID=1.1>
(Priorité d'une demande de brevet déposé" en Suisse
<EMI ID=2.1>
La présente invention a trait 1 un procédé pour la
<EMI ID=3.1>
générale
<EMI ID=4.1>
dans laquelle R représente le radical d'un acide
<EMI ID=5.1>
réaction suivant le procédé en question la configuration <EMI ID=6.1>
Le procédé mentionné ci-dessus est caractérisé en ce qu'on fait réagir un composé de la formule générale
<EMI ID=7.1>
<EMI ID=8.1>
et du groupe carboxyle,et dont le troupe basique .et protégé,
on présence d'un solvant organique/Avec de 1' ammoniac, une
<EMI ID=9.1>
compo,. de la formule générale
<EMI ID=10.1>
<EMI ID=11.1>
que ci-dessus, qu'on soumet ensuite, dans un ordre quelconque, le produit obtenu & acylation avec un dérivé capable de réagir d'un solde de
la formule générale
<EMI ID=12.1>
<EMI ID=13.1>
d'addition d'acide.
On peut préparer les anhydrides 9-carboxyliques de la
<EMI ID=14.1>
alcoolique. Afin de préparer les "Ides, on fait agir avantageusement de l'ammoniac ou une amine en excès dans un solvant
<EMI ID=15.1>
forme, sur un composé de la formule générale XI. Cette réaction <EMI ID=16.1>
méthodes usuelles en les entera basiques correspondant*.
Le premier stade du procédé en question, à savoir la
<EMI ID=17.1>
de l'hydrazine ou un composé de la formule générale III, se fait avantageusement en présence d'un solvant organique,
<EMI ID=18.1>
Une autre possibilité d'élaboration consiste en la précipitation avec de l'acide chlorhydrique aqueux. Une partie des monomères
<EMI ID=19.1>
Selon l'usage en chimie des peptides, les groupes réactifs qui ne participent pas au premier stade du procédé sont protégés avant la réaction. En ce qui concerne le groupe carboxyle, cette
<EMI ID=20.1> correspondant ou de l'amide. Dans le* composée de départ
<EMI ID=21.1>
autre possibilité de protéger les amino-acides consiste en la transformation en dérivés de phthalyle, par exemple par
<EMI ID=22.1>
nifiés de matière usuelle, par exemple avec un alcali et température ambiante.
<EMI ID=23.1>
On a constaté qu'il est avantageux de convertir, par
<EMI ID=24.1>
par traitement area de l'acide chlorhydrique alcoolique, ou, oe qui est préférable, avec du chlorure de thionyle et de l'alcool
<EMI ID=25.1>
d'après le* méthodes connues, par traitement Avec des acides inorganique" ou organiques en un mélange de sels d'addition
<EMI ID=26.1>
sont utilisées
1 <EMI ID=27.1>
<EMI ID=28.1>
<EMI ID=29.1>
<EMI ID=30.1>
<EMI ID=31.1>
de thionyle et de 100 ml de méthanol, ce "élance ayant été
<EMI ID=32.1>
<EMI ID=33.1>
dont les groupements carboxyles terminaux sont estérifiés.
<EMI ID=34.1>
de chlorure d'acide palmitique, On continue de remuer pendant 16 heure. 1 un pH de 8-9. On liquéfie l'huile épaisse obtenue, en chauffant brièvement, puis on la vers*
<EMI ID=35.1>
<EMI ID=36.1>
aveo du chlorure d'acide palmitique. on obtient de manière
<EMI ID=37.1>
<EMI ID=38.1>
V-
<EMI ID=39.1>
(obtenu suivant la méthode décrite au 4 lime paragraphe de cet
<EMI ID=40.1>
<EMI ID=41.1>
<EMI ID=42.1>
<EMI ID=43.1>
0
<EMI ID=44.1>
<EMI ID=45.1> <EMI ID=46.1> <EMI ID=47.1>
<EMI ID=48.1> <EMI ID=49.1>
avec succion, puis le résidu est lavé avec de l'éther et <EMI ID=50.1>
190-203[deg.].
<EMI ID=51.1>
125-140[deg.].
<EMI ID=52.1>
on décompose hydrogénolytiquement 20 g de ce composé, et l'Isole sous forme du chlorhydrate. On obtient 11 g du chlor-
<EMI ID=53.1>
<EMI ID=54.1>
1670.
<EMI ID=55.1>
décrite au parapgraphe précédent, on laisse reposer le "4 lange
<EMI ID=56.1> <EMI ID=57.1>
de l'eau).
Les produite obtenue suivant le procédé en question
<EMI ID=58.1>
<EMI ID=59.1>
<EMI ID=60.1>
<EMI ID=61.1>
Ces préparations peuvent se présenter sous forme de comprimés. dragées, suppositoires, capsules ou de solutions, suspensions
<EMI ID=62.1>
utiles. Ces préparations sont obtenues par les procédés usuels, Illustres ci-après.
On peut utiliser les produite de l'invention à des
<EMI ID=63.1>
<EMI ID=64.1>
<EMI ID = 1.1>
(Priority of a patent application filed "in Switzerland
<EMI ID = 2.1>
The present invention relates to a method for the
<EMI ID = 3.1>
general
<EMI ID = 4.1>
in which R represents the radical of an acid
<EMI ID = 5.1>
reaction according to the process in question the configuration <EMI ID = 6.1>
The above-mentioned process is characterized in that a compound of the general formula is reacted
<EMI ID = 7.1>
<EMI ID = 8.1>
and the carboxyl group, and whose basic and protected group,
an organic solvent is present / With ammonia, a
<EMI ID = 9.1>
compo ,. of the general formula
<EMI ID = 10.1>
<EMI ID = 11.1>
than above, which is then subjected, in any order, the product obtained to acylation with a derivative capable of reacting with a balance of
the general formula
<EMI ID = 12.1>
<EMI ID = 13.1>
addition of acid.
The 9-carboxylic anhydrides can be prepared from
<EMI ID = 14.1>
alcoholic. In order to prepare the "Ides, ammonia or an excess amine is advantageously reacted in a solvent.
<EMI ID = 15.1>
form, on a compound of the general formula XI. This reaction <EMI ID = 16.1>
usual methods in the corresponding basic entry *.
The first stage of the process in question, namely the
<EMI ID = 17.1>
hydrazine or a compound of general formula III, is advantageously carried out in the presence of an organic solvent,
<EMI ID = 18.1>
Another possibility of preparation consists of precipitation with aqueous hydrochloric acid. Some of the monomers
<EMI ID = 19.1>
According to the use in chemistry of peptides, the reactive groups which do not participate in the first stage of the process are protected before the reaction. With regard to the carboxyl group, this
<EMI ID = 20.1> corresponding or amide. In the * starting compound
<EMI ID = 21.1>
another possibility of protecting amino acids is the transformation into phthalyl derivatives, for example by
<EMI ID = 22.1>
nified with the usual material, for example with an alkali and room temperature.
<EMI ID = 23.1>
It has been found that it is advantageous to convert, for
<EMI ID = 24.1>
by area treatment of alcoholic hydrochloric acid, or, which is preferable, with thionyl chloride and alcohol
<EMI ID = 25.1>
according to known methods, by treatment With inorganic or organic acids to a mixture of addition salts
<EMI ID = 26.1>
are used
1 <EMI ID = 27.1>
<EMI ID = 28.1>
<EMI ID = 29.1>
<EMI ID = 30.1>
<EMI ID = 31.1>
of thionyl and 100 ml of methanol, this "boost having been
<EMI ID = 32.1>
<EMI ID = 33.1>
in which the terminal carboxyl groups are esterified.
<EMI ID = 34.1>
of palmitic acid chloride. Stirring is continued for 16 hours. 1 a pH of 8-9. The thick oil obtained is liquefied, heating briefly, then poured out *
<EMI ID = 35.1>
<EMI ID = 36.1>
with palmitic acid chloride. we get so
<EMI ID = 37.1>
<EMI ID = 38.1>
V-
<EMI ID = 39.1>
(obtained according to the method described in the 4th paragraph of this
<EMI ID = 40.1>
<EMI ID = 41.1>
<EMI ID = 42.1>
<EMI ID = 43.1>
0
<EMI ID = 44.1>
<EMI ID = 45.1> <EMI ID = 46.1> <EMI ID = 47.1>
<EMI ID = 48.1> <EMI ID = 49.1>
with suction, then the residue is washed with ether and <EMI ID = 50.1>
190-203 [deg.].
<EMI ID = 51.1>
125-140 [deg.].
<EMI ID = 52.1>
20 g of this compound are hydrogenolytically decomposed, and Isole in the form of the hydrochloride. 11 g of chlor-
<EMI ID = 53.1>
<EMI ID = 54.1>
1670.
<EMI ID = 55.1>
described in the previous paragraph, the "4th
<EMI ID = 56.1> <EMI ID = 57.1>
some water).
The products obtained according to the process in question
<EMI ID = 58.1>
<EMI ID = 59.1>
<EMI ID = 60.1>
<EMI ID = 61.1>
These preparations can be in the form of tablets. dragees, suppositories, capsules or solutions, suspensions
<EMI ID = 62.1>
useful. These preparations are obtained by the usual methods, illustrated below.
The products of the invention can be used for
<EMI ID = 63.1>
<EMI ID = 64.1>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR940187A FR1367775A (en) | 1963-07-03 | 1963-07-03 | Process for the preparation of mixtures of oligopeptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE634436A true BE634436A (en) |
Family
ID=8807463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE634436D BE634436A (en) | 1963-07-03 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE634436A (en) |
| FR (1) | FR1367775A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4752601A (en) * | 1983-08-12 | 1988-06-21 | Immunetech Pharmaceuticals | Method of blocking immune complex binding to immunoglobulin FC receptors |
| WO1986001211A1 (en) * | 1984-08-10 | 1986-02-27 | MERCK Patent Gesellschaft mit beschränkter Haftung | Immunotherapeutic polypeptide agents |
-
0
- BE BE634436D patent/BE634436A/fr unknown
-
1963
- 1963-07-03 FR FR940187A patent/FR1367775A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1367775A (en) | 1964-07-24 |
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