BE541651A - - Google Patents
Info
- Publication number
- BE541651A BE541651A BE541651DA BE541651A BE 541651 A BE541651 A BE 541651A BE 541651D A BE541651D A BE 541651DA BE 541651 A BE541651 A BE 541651A
- Authority
- BE
- Belgium
- Prior art keywords
- methyl
- hydroxy
- mol
- morpholine
- treated
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- HJSVBKBPQQVWFG-UHFFFAOYSA-N 6-(aminomethyl)-2,3-dihydro-1H-inden-5-ol Chemical class C1=C(O)C(CN)=CC2=C1CCC2 HJSVBKBPQQVWFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000155 melt Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 229940113083 morpholine Drugs 0.000 description 4
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 2
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 2
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DKMMGYGTAXUOAS-UHFFFAOYSA-N 6-(piperidin-1-ylmethyl)-2,3-dihydro-1H-inden-5-ol Chemical compound OC1=CC=2CCCC=2C=C1CN1CCCCC1 DKMMGYGTAXUOAS-UHFFFAOYSA-N 0.000 description 1
- QATLHXRCKJCWMN-UHFFFAOYSA-N 6-[(3-methylmorpholin-4-yl)methyl]-2,3-dihydro-1H-inden-5-ol Chemical compound CC1COCCN1CC(C(=C1)O)=CC2=C1CCC2 QATLHXRCKJCWMN-UHFFFAOYSA-N 0.000 description 1
- -1 6-morpholino-methyl-5-hydroxy-indan Chemical compound 0.000 description 1
- WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 description 1
- WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 description 1
- OQLCHIHOYHMVLX-UHFFFAOYSA-N O1CCN(CC1)CC1=C(C=C2CCCC2=C1)O Chemical compound O1CCN(CC1)CC1=C(C=C2CCCC2=C1)O OQLCHIHOYHMVLX-UHFFFAOYSA-N 0.000 description 1
- XNOPRXBHLZRZKH-DSZYJQQASA-N Oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
- 229940030215 Pitocin Drugs 0.000 description 1
- 208000010238 Uterine Inertia Diseases 0.000 description 1
- 206010046763 Uterine atony Diseases 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000002196 ecbolic Effects 0.000 description 1
- 229960001405 ergometrine Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001020 rhythmical Effects 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
<Desc/Clms Page number 1>
La présente invention concerne la.préparation de nou- veaux dérivés de 6-aminométhyl-5-hydroxy-indane représentés par la formule générale
EMI1.1
dans laquelle R représente de l'hydrogène ou un groupe méthyle et Z un atome d'oxygène ou un groupement méthylène, ainsi que leurs sels, en particulier celle de 6-pipéridino-
EMI1.2
méthyl-5-hydroxy-irdane, de 6-(21-méthyl-pipéridinom6thyl)- 5-hydroxy-indane, de 6-morpholinométhyl-5-hydroxy-indane et de 6-(3'-méthyl-morpholinométhyl)-5-hydroxy-indane, et de leurs sal-i
<Desc/Clms Page number 2>
Ces corps ont des propriétés ocytociques semblables à celles de l'ergométrine et ils provoquent chez la femme une contraction rythmique de la matrice sans en augmenter la tonicité;
ils sont donc utiles pour induire le travail-et pour combattre l'atonie utérine. A cet égard, ils présentent donc moins d'inconvénients que la pitocine.
Pour préparer les nouveaux composés mentionnés et leurs sels, on fait réagir la pipéridine, la 2-méthyl-pipéridine, la 3-méthyl-pipéridine, la morpholine, la 2-méthyl-morpholine, la 3-méthyl-morpholine ou un sel de l'un. de ces composés avec du 5-hydroxy-indane en présence de formaldéhyde et on traite le produit obtenu le cas échéant avec un acide.
La réaction peut être effectuée dans un solvant, tel que l'éthanol ou l'isopropanol. Suivant un mode de procédure préféré, on met tout d'abord la base organique en réaction avec le formaldéhyde et on ajoute ensuite le 5-hydroxy-indane.
Exemple 1
On traite 1,7 g. de pipéridine (0,02 mol) dans 2-3 ce. d'éthanol avec 1,5 ce. (0,02 mol) d'une solution aqueuse à 40% de formaldéhyde, en refroidissant et en agitant. On prépare également une solution de 2,68 g. (0,02 mol) de 5-hydroxy-indane dans 10 cc. d'éthanol. Le tout est mélangé et laissé au repos pendant env. 24 heures à 20 C. Le mélange est alors chauffé au reflux pendant 2 heures, après quoi le solvant est éliminé par distillation dans le vide. Le résidu huileux est dissous dans de l'étheret extrait trois fois avec de l'acide sulfurique 2 N; l'extrait est alors lavé une fois avec une nouvelle portion d'
<Desc/Clms Page number 3>
éther et rendu alcalin par addition d'un léger exoès de bi- carbonate de sodium solide.
La base obtenue est extraite deux fois avec de l'éther, l'extrait éthéré est lavé deux fois avec de l'eau, séché sur du sulfate de sodium anhydre et évaporé. Le produit est distillé; il se présente alors sous la forme d'une huile incolore (n 20 = 1,549) qui se solidifie lentement au re- pos. Point d'ébullition: 125-126 C/0,22 mm. Le rendement en
6-pipéridinométhyl-5-hydroxy-indane est de 2,58 g, ce qui cor- respond à 55,8% de la théorie.
Une-portion de la base' susdite est dissoute dans de 1' éther séché au préalable au moyen de sodium, puis traitée lente- ment avec la quantité équivalente de chlorure d'hydrogène an- hydre dans de l'éther sec, tout en étant remuée et refroidie.
L'hydrochlorure est alors précipité et purifié par recristalli- sation dans un mélange d'alcool absolu et d'éther sec. Il forme des cristaux blancs fondant 11 206-208 C.
Une autre portion de la base est traitée, en solution alcoolique, avec la quantité équimoléculaire d'acide maléique, le maléate acide étant précipité par addition d'éther sec. Après recristallisation dans un mélange d'alcool absolu et d'éther sec, il forme des cristaux blancs solides fondant à 118 C.
Exemple 2
On traite 9,9 g. (0,1 mol) de DL-a-pipécoline dans 10 ce. d'éthanol avec 7,5 cc. (0,1 mol) d'une solution aqueuse à 40% de formaldéhyde, tout en refroidissant et secouant. Le tout est alors-ajouté à une solution de 13,4 g. (0,1 mol) de 5-hydroxy-indane dans 25-30 cc. d'éthanol. Après un repos de
<Desc/Clms Page number 4>
3 jours à 20 C, le produit est traité suivant l'exemple 1. On obtient 16,2 g. (rendement 66%) de DL-6-(2'-méthyl-pipéridino- méthyl)-5-hydroxy-indane sous la forme d'une huile (point d' ébullition 156-158 C/0,15 mm; n20 = 1,548) qui se solidifie au repos et fond alors à 35-37 C.
L'hydrochlorure obtenu suivant le procédé décrit à l'exemple 1 fond à 173-175 C, et le maléate à 13700.
Exemple 3
On traite 1,74 g. (0,02 mol) de morpholine dans 3 oc. d'éthanol avec 1,5 ce. (0,02 mol) d'une solution aqueuse à 40% de formaldéhyde, tout en refroidissant et secouant. On ajoute alors 2,68 g. (0,02 mol) de 5-hydroxy-indane dans 5,4 ce. d' éthanol. Le mélange est laissé au repos pendant 16 heures à 2000, puis est chauffé au reflux pendant 1 heure et traité comme dans l'exemple 1. On obtient 3,14 g. de 6-morpholino- méthy1-5-hydroxy-indane (rendement 67%); le produit se présente sous la forme d'un liquide visqueux incolore (point d'ébulli- tion 134 C/0,19 mm; n20D = 1,556) qui se solidifie au repos et fond à 41-44 C. Le maléate obtenu suivant le procédé décrit à l'exemple 1 fond à 133 C.
Exemple 4
Le procédé de l'exemple 3 est répété, sauf qu'au lieu de morpholine on emploie 2,02 g. (0,02 mol) de DL-3-méthyl- morpholine. On obtient ainsi 3,30 g. de DL-6-(3'-méthyl-morpho-
EMI4.1
linométhyla-5-hydroxy-indanQ ,(rendement 66,'l%). Après distilla- tion, le produit se présente bous la forme d'un liquide visqueux. incolore (Point d'ébullition 141 C/0,15 mm) qui se solidifie
<Desc/Clms Page number 5>
bientôt et fond à 58-60 C. Lthydrochlorure fond à 193-195 C. et le maléate à 157 C.
Revendicationa:
1. Procédé pour la préparation de nouveaux dérivés de 6-aminométhy1-5-hydroxy-indane de la formule générale
EMI5.1
dans laquelle R représente un atome d'hydrogène ou le groupement méthyle, et Z un atome d'hydrogène ou le groupement méthylène, et de leurs sels, caractérisé par le fait que l'on fait réagir la pipéridine, la 2-méthyl-pipéridine, la 3-méthyl-pipéridine, la morpholine, la 2-méthyl-morpholine, la 3-méthyl-morpholine ou un sel de l'un de.ces composés avec du 5-hydroxy-indane en pré- sence de formaldéhyde et que l'on traite le produit obtenu, le cas échéant, avec un acide.
<Desc / Clms Page number 1>
The present invention relates to the preparation of novel 6-aminomethyl-5-hydroxy-indan derivatives represented by the general formula
EMI1.1
in which R represents hydrogen or a methyl group and Z an oxygen atom or a methylene group, as well as their salts, in particular that of 6-piperidino-
EMI1.2
methyl-5-hydroxy-irdane, 6- (21-methyl-piperidinom6thyl) - 5-hydroxy-indane, 6-morpholinomethyl-5-hydroxy-indane and 6- (3'-methyl-morpholinomethyl) -5- hydroxy-indan, and their sal-i
<Desc / Clms Page number 2>
These bodies have oxytocic properties similar to those of ergometrine and they cause a rhythmic contraction of the matrix in women without increasing its tonicity;
they are therefore useful for inducing labor and for combating uterine atony. In this respect, they therefore have fewer drawbacks than pitocin.
To prepare the new compounds mentioned and their salts, one reacts piperidine, 2-methyl-piperidine, 3-methyl-piperidine, morpholine, 2-methyl-morpholine, 3-methyl-morpholine or a salt of Mon. of these compounds with 5-hydroxy-indane in the presence of formaldehyde and the product obtained is treated, where appropriate, with an acid.
The reaction can be carried out in a solvent, such as ethanol or isopropanol. According to a preferred procedure, the organic base is first reacted with formaldehyde and then 5-hydroxy-indane is added.
Example 1
1.7 g are treated. of piperidine (0.02 mol) in 2-3 cc. of ethanol with 1.5 cc. (0.02 mol) of a 40% aqueous formaldehyde solution, with cooling and stirring. A 2.68 g solution is also prepared. (0.02 mol) of 5-hydroxy-indan in 10 cc. ethanol. Everything is mixed and left to stand for approx. 24 hours at 20 ° C. The mixture is then heated under reflux for 2 hours, after which the solvent is removed by distillation in a vacuum. The oily residue is dissolved in ether and extracted three times with 2N sulfuric acid; the extract is then washed once with a new portion of
<Desc / Clms Page number 3>
ether and made alkaline by adding a slight excess of solid sodium bicarbonate.
The base obtained is extracted twice with ether, the ethereal extract is washed twice with water, dried over anhydrous sodium sulfate and evaporated. The product is distilled; it is then in the form of a colorless oil (n 20 = 1.549) which solidifies slowly on standing. Boiling point: 125-126 C / 0.22 mm. The yield in
6-piperidinomethyl-5-hydroxy-indan is 2.58 g, which corresponds to 55.8% of theory.
A portion of the aforesaid base is dissolved in ether previously dried with sodium, then slowly treated with the equivalent amount of anhydrous hydrogen chloride in dry ether, while being stirred and cooled.
The hydrochloride is then precipitated and purified by recrystallization from a mixture of absolute alcohol and dry ether. It forms white crystals melting 11 206-208 C.
Another portion of the base is treated, in alcoholic solution, with the equimolecular quantity of maleic acid, the acid maleate being precipitated by addition of dry ether. After recrystallization from a mixture of absolute alcohol and dry ether, it forms solid white crystals melting at 118 C.
Example 2
9.9 g are treated. (0.1 mol) DL-α-pipecoline in 10 cc. of ethanol with 7.5 cc. (0.1 mol) of a 40% aqueous formaldehyde solution, while cooling and shaking. The whole is then added to a solution of 13.4 g. (0.1 mol) of 5-hydroxy-indan in 25-30 cc. ethanol. After a rest of
<Desc / Clms Page number 4>
3 days at 20 ° C., the product is treated according to Example 1. 16.2 g are obtained. (yield 66%) of DL-6- (2'-methyl-piperidinomethyl) -5-hydroxy-indane as an oil (bp 156-158 C / 0.15 mm; n20 = 1.548) which solidifies on standing and then melts at 35-37 C.
The hydrochloride obtained by the process described in Example 1 melts at 173-175 ° C., and the maleate at 13700.
Example 3
1.74 g are treated. (0.02 mol) of morpholine in 3 oc. of ethanol with 1.5 cc. (0.02 mol) of a 40% aqueous formaldehyde solution, while cooling and shaking. 2.68 g are then added. (0.02 mol) of 5-hydroxy-indan in 5.4 cc. ethanol. The mixture is left to stand for 16 hours at 2000, then is heated under reflux for 1 hour and treated as in Example 1. 3.14 g is obtained. 6-morpholino-methyl-5-hydroxy-indan (yield 67%); the product is in the form of a colorless viscous liquid (boiling point 134 C / 0.19 mm; n20D = 1.556) which solidifies on standing and melts at 41-44 C. The maleate obtained according to process described in Example 1 melts at 133 C.
Example 4
The process of Example 3 is repeated except that instead of morpholine 2.02 g are used. (0.02 mol) DL-3-methyl-morpholine. This gives 3.30 g. of DL-6- (3'-methyl-morpho-
EMI4.1
linomethyla-5-hydroxy-indanQ, (yield 66.1%). After distillation, the product appears as a viscous liquid. colorless (boiling point 141 C / 0.15 mm) which solidifies
<Desc / Clms Page number 5>
soon and melts at 58-60 C. The hydrochloride melts at 193-195 C. and the maleate at 157 C.
Claima:
1. Process for the preparation of novel 6-aminomethy1-5-hydroxy-indan derivatives of the general formula
EMI5.1
in which R represents a hydrogen atom or the methyl group, and Z a hydrogen atom or the methylene group, and their salts, characterized in that the piperidine, 2-methyl-piperidine is reacted , 3-methyl-piperidine, morpholine, 2-methyl-morpholine, 3-methyl-morpholine or a salt of any of these compounds with 5-hydroxy-indane in the presence of formaldehyde and the product obtained is treated, where appropriate, with an acid.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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BE541651A true BE541651A (en) |
Family
ID=170563
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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Country Status (1)
Country | Link |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2413358A1 (en) * | 1977-12-29 | 1979-07-27 | Ono Pharmaceutical Co | NEW 2-AMINOMETHYLPHENOL DERIVATIVES, USEFUL IN PARTICULAR AS ANTI-INFLAMMATORY AGENTS, AND THEIR PREPARATION PROCESS |
-
0
- BE BE541651D patent/BE541651A/fr unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2413358A1 (en) * | 1977-12-29 | 1979-07-27 | Ono Pharmaceutical Co | NEW 2-AMINOMETHYLPHENOL DERIVATIVES, USEFUL IN PARTICULAR AS ANTI-INFLAMMATORY AGENTS, AND THEIR PREPARATION PROCESS |
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