FR266M - - Google Patents
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- Publication number
- FR266M FR266M FR836478A FR836478A FR266M FR 266 M FR266 M FR 266M FR 836478 A FR836478 A FR 836478A FR 836478 A FR836478 A FR 836478A FR 266 M FR266 M FR 266M
- Authority
- FR
- France
- Prior art keywords
- cis
- urea
- trans
- compounds
- decalyi
- 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
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- 239000004202 carbamide Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229940126904 hypoglycaemic agent Drugs 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- -1 polycyclic compounds Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
- A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
RÉPUBLIQUE FRANÇAISEFRENCH REPUBLIC
MINISTERE DE L'INDUSTRIEMINISTRY OF INDUSTRY
BREVET SPÉCIAL DE MÉDICAMENTSPECIAL MEDICINAL PATENT
SERVICE de la PROPRIÉTÉ INDUSTRIELLEINDUSTRIAL PROPERTY SERVICE
P.y. n° 836.478P.y. No. 836.478
Classification internationaleInternational classification
N° 266 M A 61 k — C 07 cN ° 266 M A 61 k - C 07 c
Composés polycycliques.Polycyclic compounds.
Société dite : F. HOFFMANN-LA ROCHE & CIE Société Anonyme résidant en Suisse.Company known as: F. HOFFMANN-LA ROCHE & CIE Société Anonyme residing in Switzerland.
Demandé le 23 août 1960, à ll!l 18m, à Paris.Requested on August 23, 1960, at ll! L 18m, in Paris.
Délivré par arrêté du 6 mars 1961.Issued by decree of March 6, 1961.
(Bulletin officiel de la Propriété industrielle [5.S.M.], n° 7 de 1961.) (2 demandes de brevets déposées aux États-Unis d'Amérique les 13 mai 1959, sous le n° 812.833, et 15 septembre 1959, sous le n° 840.104, aux noms de MM. John Alfred Aeschlimann et Arthur Stempel.)(Official Bulletin of Industrial Property [5.SM], No. 7 of 1961.) (2 patent applications filed in the United States of America on May 13, 1959, under No. 812,833, and September 15, 1959, under n ° 840.104, in the names of Messrs. John Alfred Aeschlimann and Arthur Stempel.)
(Brevet résultant de la division de la demande de brevet d'invention, P.V. n° 826.930, déposée le 12 mai 1960.)(Patent resulting from division of invention patent application, P.V. No. 826,930, filed May 12, 1960.)
La présente invention a trait à des composés polycycliques de la formule générale :The present invention relates to polycyclic compounds of the general formula:
x-<fx- <f
(I)(I)
haHa
*/Ç\*/VS\
sog-nh-co-nh-ch I a h Osog-nh-co-nh-ch I a h O
Ha 7 CHaHa 7 CHa
HaC s C" i CitaHaC s C "i Cita
\£/H\A/\ £ / H \ A /
HaHa
Ha dans laquelle X représente un atome d'hydrogène, de chlore ou de brome, ou un groupement méthyle, et les atomes d'hydrogène situés à la jonction des deux noyaux, c'est-à-dire en positions 9 et 10 du radical 2-décahydronaphtyie, sont en position « cis » l'un par rapport à l'autre, et de leurs sels.Ha in which X represents a hydrogen, chlorine or bromine atom, or a methyl group, and the hydrogen atoms located at the junction of the two rings, that is to say in positions 9 and 10 of the radical 2-decahydronaphthyia, are in the "cis" position with respect to each other, and their salts.
Pour plus de brévité, le groupement de 2-décahy-dronaphtyle est désigné ci-après par 2-décalyl. Pour une meilleure compréhension de la nomenclature utilisée, les atomes de carbone du radical naphtyle ont été numérotés dans la formule I ci-dessus et un atome de carbone asymétrique marqué d'un astérisque.For the sake of brevity, the 2-decahy-dronaphthyl group is hereinafter referred to as 2-decalyl. For a better understanding of the nomenclature used, the carbon atoms of the naphthyl radical have been numbered in formula I above and an asymmetric carbon atom marked with an asterisk.
L'invention concerne en particulier les préparations nouvelles contenant le médicament nouveau représenté par la formule générale ci-dessus.In particular, the invention relates to novel preparations containing the novel drug represented by the above general formula.
Ce médicament nouveau peut être préparé suivant le procédé décrit plus en détail dans la demande de brevet déposée en France par la demanderesse, le 12 mai 1960, pour « Procédé pour la préparation de composés polycycliques ». Ce procédé est notamment caractérisé par le fait que l'on fait réagir une cis-2-décalylamine avec un composé de la formule généraleThis new drug can be prepared according to the process described in more detail in the patent application filed in France by the applicant on May 12, 1960, for “Process for the preparation of polycyclic compounds”. This process is in particular characterized by the fact that a cis-2-decalylamine is reacted with a compound of the general formula
(II)(II)
X-X-
y. v so2-r dans laquelle X a la même signification que ci-dessus et H représente le groupement uréido (—NH—CO— NH2) ou le radical d'isocyanate, et, le cas échéant, que l'on transforme le produit obtenu en un sel.y. v so2-r in which X has the same meaning as above and H represents the ureido group (—NH — CO — NH2) or the isocyanate radical, and, where appropriate, the product obtained is converted in a salt.
La désignation « cis » dans l'expression « cis-2-décalyi » se rapporte à la configuration relative des atomes d'hydrogène attachés aux atomes de carbone en positions 9 et 10 du radical décalyie.The designation "cis" in the expression "cis-2-decalyi" refers to the relative configuration of the hydrogen atoms attached to the carbon atoms at positions 9 and 10 of the decalyi radical.
Les composés de la formule générale I et leurs équivalents pharmaceutiques, c'est-à-dire les sels de ces composés obtenus avec des bases organiques et inorganiques usuellement utilisées dans des buts thérapeutiques, par exemple l'hydroxyde de sodium, de potassium ou d'ammonium, la diéthanolamine, la triéthanolamine, etc., peuvent être utilisés comme agents hypoglycémiques. Les composés de la formule générale I se prêtent, par voie buccale, en particulier pour abaisser le niveau du sucre sanguin. Il peuvent en général être utilisés de la même manière que les agents hypoglycémiques connus du type tolbutamide et d'autres sulfonylurées substituées.The compounds of general formula I and their pharmaceutical equivalents, that is to say the salts of these compounds obtained with organic and inorganic bases usually used for therapeutic purposes, for example sodium, potassium or sodium hydroxide. Ammonium, diethanolamine, triethanolamine, etc., can be used as hypoglycemic agents. The compounds of general formula I are suitable, by the oral route, in particular for lowering the level of blood sugar. They can generally be used in the same manner as the known hypoglycemic agents of the tolbutamide type and other substituted sulfonylureas.
Lors d'essais effectués sur des rats, il a été établi que l'activité hypoglycémiques des composés de l'invention ne dépend pas de leur activité optique. Ainsi, des essais avec l'un des composés suivant l'invention, c'est-à-dire la l-p-tosyi-3-(cis-trans-2-décalyi)-urée, ont démontré que la forme racémique la forme dextrogyre et la forme lévogyre avaientIn tests carried out on rats, it was established that the hypoglycaemic activity of the compounds of the invention does not depend on their optical activity. Thus, tests with one of the compounds according to the invention, that is to say lp-tosyi-3- (cis-trans-2-decalyi) -urea, demonstrated that the racemic form the dextrorotatory form and the levorotatory shape had
4150141501
Prix du fascicule : 1 NFPrice of the booklet: 1 NF
[266 M] — 2 —[266 M] - 2 -
grandement la même activité hypoglycémique. Les essais ont cependant démontré que l'activité hypoglycémique dépendait de la forme géométrique de la molécule au point de vue de l'isomérisme cis-trans. On a trouvé que la l-p-tosyi-3-(cis-trans-2-décalyi)-urée et les mélanges isomériques contenant ces composés, c'est-à-dire la l-p-tosyl-3-(cis-[eis -,L trans]-2-décalyî)-urée, avaient une plus grande activité hypoglycémique sur le rat que la l-p-tosyi-3-(cis-cis-2-décalyi)-urée.greatly the same hypoglycemic activity. However, the tests demonstrated that the hypoglycemic activity depended on the geometric shape of the molecule from the point of view of cis-trans isomerism. It has been found that lp-tosyi-3- (cis-trans-2-decalyi) -urea and isomeric mixtures containing these compounds, i.e. lp-tosyl-3- (cis- [eis - , L trans] -2-decalyi) -urea, had greater hypoglycemic activity in rats than lp-tosyi-3- (cis-cis-2-decalyi) -urea.
Les nouvelles préparations médicamenteuses selon l'invention peuvent contenir la substance active en mélange avec un véhicule pharmaceutique qui peut être organique ou inorganique, solide ou liquide, adapté à l'administration per os ou parenté-raie. Comme véhicule pharmaceutique, on peut utiliser des substances qui ne réagissent pas avec les composés nouveaux, par exemple l'eau, la gélatine, le lactose, l'amidon, le stéarate de magnésium, le talc, les huiles végétales et les autres véhicules d'usage dans les préparations médicamenteuses. Ces préparations peuvent se présenter sous forme de comprimés, de dragées ou de solutions, suspensions ou émulsions. Le cas échéant, les préparations peuvent être stérilisées et/ou peuvent contenir des substances auxiliaires, par exemple des agents conservateurs, stabilisants, de mouillage ou d'émulsi-fication. Ils peuvent également contenir des sels régularisant la pression osmotique ou des composés-tampon. Ces préparations sont obtenues par les procédés usuels, illustrés par les exemples suivants.The new medicinal preparations according to the invention can contain the active substance in admixture with a pharmaceutical vehicle which can be organic or inorganic, solid or liquid, suitable for oral or parenteral administration. As the pharmaceutical carrier, substances which do not react with the new compounds can be used, for example water, gelatin, lactose, starch, magnesium stearate, talc, vegetable oils and other carriers of the drug. for use in medicinal preparations. These preparations can be in the form of tablets, dragees or solutions, suspensions or emulsions. Where appropriate, the preparations may be sterilized and / or may contain auxiliary substances, for example preservatives, stabilizers, wetting or emulsification. They can also contain salts regulating the osmotic pressure or buffer compounds. These preparations are obtained by the usual methods, illustrated by the following examples.
Exemple 1. — 500 g de l-p-tosyi-3-(DL-cis-trans-2-décalyi)-urée, 3 g de gélatine, 40 g d'amidon de maïs, 35 g de lactose, 20 g de talc et 2 g de stéarate de magnésium sont intimement mélangés et triturés. La masse ainsi obtenue est pressée de manière usuelle en tablettes de 600 mg contenant 500 mg de substance active.Example 1. - 500 g of lp-tosyi-3- (DL-cis-trans-2-decalyi) -urea, 3 g of gelatin, 40 g of corn starch, 35 g of lactose, 20 g of talc and 2 g of magnesium stearate are thoroughly mixed and triturated. The mass thus obtained is pressed in the usual manner into tablets of 600 mg containing 500 mg of active substance.
RÉSUMÉABSTRACT
L'invention a pour objet :The subject of the invention is:
A titre de médicament nouveau : 1° Les composés polycycliques de la formule générale :As a new drug: 1 ° Polycyclic compounds of the general formula:
X-/X- /
H2 HsH2 Hs
/C\H/C\/ C \ H / C \
J>-S02-NH-C0-NH-CH G CHaJ> -S02-NH-C0-NH-CH G CHa
HaC C CHiHaC C CHi
\c/H\c/\ c / H \ c /
Ha Ha dans laquelle X représente un atome d'hydrogène, de chlore ou de brome, ou un groupement méthyle, et les atomes d'hydrogène situés à la jonction des noyaux, c'est-à-dire en positions 9 et 10 du radical 2-décahydronaphtyle, sont en position « cis » l'un par rapport à l'autre, et leurs sels avec des bases pharmaceutiquement acceptables;Ha Ha in which X represents a hydrogen, chlorine or bromine atom, or a methyl group, and the hydrogen atoms located at the junction of the nuclei, that is to say in positions 9 and 10 of the radical 2-decahydronaphthyl, are in the "cis" position relative to each other, and their salts with pharmaceutically acceptable bases;
2° La l-p-tosyl-3-(cis-trans-2-décalyi)-urée;2 ° 1-p-tosyl-3- (cis-trans-2-decalyi) -urea;
3° La l-p-tosyi-3-(cis-[cis + trans]-2-décalyl)-urée;3 ° 1-p-tosyi-3- (cis- [cis + trans] -2-decalyl) -urea;
4Q La l-p-chlorophénylsulfonyl-3-( cis-trans-2-dé-calyi)-urée;4Q 1-p-Chlorophenylsulfonyl-3- (cis-trans-2-decalyl) -urea;
5° La l-phénylsulfonyi-3-(cis-trans-2-décalyl)-urée;5 ° 1-phenylsulfonyi-3- (cis-trans-2-decalyl) -urea;
6° La l-p-tosyl-3-(cis-trans-2-décalyl)-urée racé-6 ° The l-p-tosyl-3- (cis-trans-2-decalyl) -urea rac-
ique;ic;
7° La l-p-tosyl-3-(cis-trans-2-déealyl)-urée lévo-gyre ou dextrogyre ;7 ° L-p-tosyl-3- (cis-trans-2-dealyl) -urea levogyre or dextrorotatory;
8° Les préparations médicamenteuses contenant les composés définis aux alinéas 1° à 7° ci-dessus.8 ° Medicinal preparations containing the compounds defined in paragraphs 1 ° to 7 ° above.
Société dite : F. HOFFMANN-LA ROCHE & CIE Société AnonymeCompany known as: F. HOFFMANN-LA ROCHE & CIE Public limited company
Par procuration :Vicarious :
étienne CoulombEtienne Coulomb
Pour la vente des fascicules, s'adresser à I'Imprimerie Nationale, 27, rue de la Convention, Paris (15*).To sell the booklets, contact the Imprimerie Nationale, 27, rue de la Convention, Paris (15 *).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81283359A | 1959-05-13 | 1959-05-13 | |
| US840014A US2974166A (en) | 1959-09-15 | 1959-09-15 | Certain 1-arylsulfonyl-3-(cis-2-decalyl)ureas |
| FR826930A FR1292947A (en) | 1960-05-12 | 1960-05-12 | Process for the preparation of polycyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR266M true FR266M (en) | 1961-02-17 |
Family
ID=39143167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR836478A Expired FR266M (en) | 1959-05-13 | 1960-08-23 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE590649A (en) |
| FR (1) | FR266M (en) |
-
1960
- 1960-05-09 BE BE590649A patent/BE590649A/en unknown
- 1960-08-23 FR FR836478A patent/FR266M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE590649A (en) | 1960-11-09 |
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