BE578516A - Dérivés de diphényl-méthane et leur procédé de préparation - Google Patents

Dérivés de diphényl-méthane et leur procédé de préparation

Info

Publication number: BE578516A
Authority: BE; Belgium
Prior art keywords: groups; compounds; derivatives; carbon atoms; aliphatic
Prior art date: 1958-05-07

Application number

BE578516A

Other languages

English (en)

French (fr)

Original Assignee

Hoechst Ag

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.)

1958-05-07

Filing date

1959-05-05

Publication date

1959-11-09

1959-05-05 Application filed by Hoechst Ag filed Critical Hoechst Ag

1959-11-09 Publication of BE578516A publication Critical patent/BE578516A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 12
-1 aliphatic dicarboxylic acids Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
230000010933 acylation Effects 0.000 claims description 5
238000005917 acylation reaction Methods 0.000 claims description 5
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 4
229940054021 anxiolytics diphenylmethane derivative Drugs 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims 3
125000001931 aliphatic group Chemical group 0.000 claims 2
150000002763 monocarboxylic acids Chemical class 0.000 claims 2
125000003277 amino group Chemical group 0.000 claims 1
150000001991 dicarboxylic acids Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
238000004821 distillation Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
210000004351 coronary vessel Anatomy 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
230000010339 dilation Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
230000002035 prolonged effect Effects 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229940014800 succinic anhydride Drugs 0.000 description 2
238000004448 titration Methods 0.000 description 2
229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
239000007868 Raney catalyst Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
BCUPGIHTCQJCSI-UHFFFAOYSA-N chloromethanol Chemical compound OCCl BCUPGIHTCQJCSI-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical class O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000000622 irritating effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides

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)

BE578516A 1958-05-07 1959-05-05 Dérivés de diphényl-méthane et leur procédé de préparation BE578516A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF25703A DE1122510B (de)	1958-05-07	1958-05-07	Verfahren zur Herstellung von herz- und kreislaufwirksamen wasserloeslichen Alkalisalzen von N-acylierten Diphenylmethanderivaten

Publications (1)

Publication Number	Publication Date
BE578516A true BE578516A (fr)	1959-11-09

Family

ID=7091733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE578516A BE578516A (fr)	1958-05-07	1959-05-05	Dérivés de diphényl-méthane et leur procédé de préparation

Country Status (5)

Country	Link
BE (1)	BE578516A (de)
CH (1)	CH422754A (de)
DE (1)	DE1122510B (de)
FR (1)	FR1341457A (de)
GB (1)	GB920841A (de)

1958
- 1958-05-07 DE DEF25703A patent/DE1122510B/de active Pending
1959
- 1959-05-05 CH CH7291959A patent/CH422754A/de unknown
- 1959-05-05 BE BE578516A patent/BE578516A/fr unknown
- 1959-05-07 GB GB15786/59A patent/GB920841A/en not_active Expired
- 1959-05-09 FR FR794222A patent/FR1341457A/fr not_active Expired

Also Published As

Publication number	Publication date
FR1341457A (fr)	1963-11-02
CH422754A (de)	1966-10-31
DE1122510B (de)	1962-01-25
GB920841A (en)	1963-03-13

Publication	Publication Date	Title
BE851310A (fr)	1977-08-10	Nouveaux derives de la tetrahydro-equinocandine b
EP0003445A1 (de)	1979-08-08	1-Aza-bicyclo(2,2,2)octane, Verfahren zu ihrer Herstellung und Zwischenprodukte, und deren Arzneimittel
EP0074903A2 (de)	1983-03-23	2-Amino-1,2,3,4-tetrahydronaphthalen-Derivate, ihre Herstellung und ihre therapeutische Verwendung
BE897000A (fr)	1983-12-09	Nouveaux derives de la 1,4-dihydropyridine,leur preparation et leur utilisation comme medicaments
CH622795A5 (de)	1981-04-30
EP0130882B1 (de)	1987-01-07	Bicyclo(3.2.1)octancarbonsäure-Derivate, Verfahren zu ihren Herstellung und ihre therapeutische Verwendung
CA1088099A (fr)	1980-10-21	Procede de preparation de nouveaux alcoxy anilides et composes ainsi obtenus
CA1045140A (en)	1978-12-26	Ester of n-(8 trifluoromethyl 4- quinolyl)-anthranilate
WO1992021665A1 (fr)	1992-12-10	Nouveaux derives de l'oxazole et leur preparation
FR2491471A1 (fr)	1982-04-09	Benzoxazolinones substituees, leur preparation et leur application en therapeutique
BE633453A (de)
EP0151052A2 (de)	1985-08-07	Aminoäthylimidazole, pharmazeutische Zusammensetzungen die sie enthalten und Verfahren zu ihrer Herstellung
BE503775A (de)
BE574132A (de)
BE598605A (en)	1961-06-28	Alkenylamines and pharmaceutical preparations containing them
BE581750A (de)
CH429719A (fr)	1967-02-15	Procédé de préparation de nouveaux diamino stéroïdes
CH592093A5 (en)	1977-10-14	7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents
BE562179A (de)
BE572685A (de)
MC733A1 (fr)	1969-08-04	2-alcoxy-4,5-azimidobenzamides et leur procédé de préparation
BE546149A (de)
CH628629A5 (en)	1982-03-15	Derivatives of piperidylindole and their salts
CH487104A (fr)	1970-03-15	Procédé de préparation de nouveaux dérivés de l'acide benzoyl-3 phénylacétique
CH592665A5 (en)	1977-10-31	7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents