CH409940A - Procédé de préparation d'un nouveau dérivé de l'adamantane - Google Patents

Procédé de préparation d'un nouveau dérivé de l'adamantane

Info

Publication number: CH409940A
Authority: CH; Switzerland
Prior art keywords: adamantane; oxy; adamantyl; dérivé; nouveau
Prior art date: 1961-03-24

Application number

CH338862A

Other languages

English (en)

French (fr)

Inventor

Marie Preau Nicole

Original Assignee

Rhone Poulenc Sa

Priority date (The priority date 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 date listed.)

1961-03-24

Filing date

1962-03-23

Publication date

1966-03-31

1961-03-24 Priority claimed from FR856752A external-priority patent/FR1385358A/fr

1962-02-22 Priority claimed from FR888858A external-priority patent/FR1322972A/fr

1962-03-23 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1966-03-31 Publication of CH409940A publication Critical patent/CH409940A/de

Links

ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 8
235000019260 propionic acid Nutrition 0.000 claims description 6
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
125000005075 adamantyloxy group Chemical group C12(CC3CC(CC(C1)C3)C2)O* 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
238000006386 neutralization reaction Methods 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
229910052601 baryte Inorganic materials 0.000 description 1
239000010428 baryte Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000001989 choleretic effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
- C07C59/13—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups containing rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH338862A 1961-03-24 1962-03-23 Procédé de préparation d'un nouveau dérivé de l'adamantane CH409940A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR856752A FR1385358A (fr)	1961-03-24	1961-03-24	Nouveau dérivé de l'adamantane et son procédé de préparation
FR888858A FR1322972A (fr)	1962-02-22	1962-02-22	Nouveau dérivé de l'adamantane et son procédé de préparation

Publications (1)

Publication Number	Publication Date
CH409940A true CH409940A (de)	1966-03-31

Family

ID=26189831

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH338862A CH409940A (de)	1961-03-24	1962-03-23	Procédé de préparation d'un nouveau dérivé de l'adamantane

Country Status (2)

Country	Link
CH (1)	CH409940A (de)
GB (1)	GB991297A (de)

1962
- 1962-03-23 GB GB1122862A patent/GB991297A/en not_active Expired
- 1962-03-23 CH CH338862A patent/CH409940A/de unknown

Also Published As

Publication number	Publication date
GB991297A (en)	1965-05-05

Publication	Publication Date	Title
CH462136A (fr)	1968-09-15	Procédé de préparation de dérivés de l'acide a-phényl-propionique
CH409940A (de)	1966-03-31	Procédé de préparation d'un nouveau dérivé de l'adamantane
CH380134A (fr)	1964-07-31	Procédé de préparation de nouveaux dérivés de la phénothiazine
CH338197A (fr)	1959-05-15	Procédé d'obtention de peptides
CH573386A5 (en)	1976-03-15	Para-Isobutyl-phenyl-butyric acid prepn. - from corresp. acetonitrile cpd., having antiinflammatory, analgesic and antipyretic activity
CH237879A (fr)	1945-05-31	Procédé de préparation de l' -diméthyl-ss-cyclohexyléthylamine.
CH205678A (fr)	1939-06-30	Procédé de préparation de la 2-(para-amino-benzène-sulfamido)-pyridine.
CH288988A (fr)	1953-02-15	Procédé de préparation d'un acylamidodiol aromatique, nitré dans le noyau.
CH214344A (fr)	1941-04-15	Procédé de préparation de la 2-(para-amino-benzène-sulfamido)-6-méthyl-pyridine.
CH370093A (fr)	1963-06-30	Procédé pour la préparation de dérivés de l'acide diamino-caproïque
CH382152A (fr)	1964-09-30	Procédé pour la préparation de m-sulfobenzoates de stéroïdes
CH288985A (fr)	1953-02-15	Procédé de préparation d'un acylamidodiol aromatique, nitré dans le noyau.
CH298327A (fr)	1954-04-30	Procédé de préparation d'une forme thérapeutiquement active de la thréo-2-dichlorométhyl-4-hydroxyméthyl-5-p-nitrophényl-oxazoline-2.
CH247556A (fr)	1947-03-15	Procédé de préparation du paramino-benzoyl-phtalamate d'éthyle.
CH207309A (fr)	1939-10-15	Procédé de préparation de la 2-(para-amino-benzène-sulfamido)-pyridine.
CH400185A (fr)	1965-10-15	Procédé pour la préparation de lactones a-carboxylées
BE598705A (de)
BE623369A (de)	1963-04-08
CH368164A (fr)	1963-03-31	Procédé pour la préparation de dérivés de l'étiocholane
BE337700A (de)
CH276043A (fr)	1951-06-15	Procédé de préparation de la cycloheptadécanone.
BE444578A (fr)	1942-03-31	Procédé pour l'obtention de succédanés pour des épices poivrées
BE528126A (de)
CH96144A (fr)	1922-09-16	Procédé pour la production de l'éther n-a-butylique de l'acide p-aminobenzoïque.
BE571857A (de)