CH447160A - Procédé de préparation de composés organiques de l'aluminium thérapeutiquement actifs - Google Patents

Procédé de préparation de composés organiques de l'aluminium thérapeutiquement actifs

Info

Publication number: CH447160A
Authority: CH; Switzerland
Prior art keywords: acid; substance; group; hydrolysis; aluminum
Prior art date: 1959-09-07

Application number

CH1007360A

Other languages

English (en)

French (fr)

Inventor

Kay Davison Brian

Original Assignee

Hardman & Holden Ltd

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.)

1959-09-07

Filing date

1960-09-06

Publication date

1967-11-30

1960-09-06 Application filed by Hardman & Holden Ltd filed Critical Hardman & Holden Ltd

1967-11-30 Publication of CH447160A publication Critical patent/CH447160A/fr

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 title description 5
229910052782 aluminium Inorganic materials 0.000 claims description 15
230000007062 hydrolysis Effects 0.000 claims description 14
238000006460 hydrolysis reaction Methods 0.000 claims description 14
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
-1 aluminum alkoxide Chemical class 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
239000013543 active substance Substances 0.000 claims description 7
239000005711 Benzoic acid Substances 0.000 claims description 6
235000010233 benzoic acid Nutrition 0.000 claims description 6
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 5
150000004703 alkoxides Chemical group 0.000 claims description 5
229960004909 aminosalicylic acid Drugs 0.000 claims description 5
229960004365 benzoic acid Drugs 0.000 claims description 5
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
125000002843 carboxylic acid group Chemical group 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
239000005642 Oleic acid Substances 0.000 claims description 3
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
235000021355 Stearic acid Nutrition 0.000 claims description 3
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
239000008117 stearic acid Substances 0.000 claims description 3
XMVQWNRDPAAMJB-UHFFFAOYSA-N (+)-13-Cyclopent-2-enyl-tridecansaeure Natural products OC(=O)CCCCCCCCCCCCC1CCC=C1 XMVQWNRDPAAMJB-UHFFFAOYSA-N 0.000 claims description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
XMVQWNRDPAAMJB-QGZVFWFLSA-N (S)-chaulmoogric acid Chemical compound OC(=O)CCCCCCCCCCCC[C@H]1CCC=C1 XMVQWNRDPAAMJB-QGZVFWFLSA-N 0.000 claims description 2
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 2
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
229930182555 Penicillin Natural products 0.000 claims description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
239000000174 gluconic acid Substances 0.000 claims description 2
235000012208 gluconic acid Nutrition 0.000 claims description 2
229950006191 gluconic acid Drugs 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
229960000448 lactic acid Drugs 0.000 claims description 2
229960002510 mandelic acid Drugs 0.000 claims description 2
229960003512 nicotinic acid Drugs 0.000 claims description 2
235000001968 nicotinic acid Nutrition 0.000 claims description 2
239000011664 nicotinic acid Substances 0.000 claims description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
229940049954 penicillin Drugs 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
229940127557 pharmaceutical product Drugs 0.000 claims description 2
229960004889 salicylic acid Drugs 0.000 claims description 2
235000021313 oleic acid Nutrition 0.000 claims 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
235000010323 ascorbic acid Nutrition 0.000 description 3
239000011668 ascorbic acid Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
229960005070 ascorbic acid Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
201000006747 infectious mononucleosis Diseases 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229940049964 oleate Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BIHGMNAEAOIWJW-ZMUFBLIFSA-K (2R)-3-[bis[[(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2H-furan-3-yl]oxy]alumanyloxy]-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-2H-furan-5-one Chemical compound [Al+3].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BIHGMNAEAOIWJW-ZMUFBLIFSA-K 0.000 description 1
ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
229930003268 Vitamin C Natural products 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
WPAIKTKBIXBRHU-UHFFFAOYSA-K aluminum 5-amino-2-carboxyphenolate octadecanoate Chemical compound NC=1C=C(C(C(=O)[O-])=CC1)O.C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Al+3] WPAIKTKBIXBRHU-UHFFFAOYSA-K 0.000 description 1
229940083916 aluminum distearate Drugs 0.000 description 1
SMBUEDZEFSOKBW-UHFFFAOYSA-K aluminum;5-amino-2-carboxyphenolate Chemical class [Al+3].NC1=CC=C(C([O-])=O)C(O)=C1.NC1=CC=C(C([O-])=O)C(O)=C1.NC1=CC=C(C([O-])=O)C(O)=C1 SMBUEDZEFSOKBW-UHFFFAOYSA-K 0.000 description 1
RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 1
CSJKPFQJIDMSGF-UHFFFAOYSA-K aluminum;tribenzoate Chemical compound [Al+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 CSJKPFQJIDMSGF-UHFFFAOYSA-K 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
229940050390 benzoate Drugs 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
235000020075 ouzo Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages

Landscapes

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

CH1007360A 1959-09-07 1960-09-06 Procédé de préparation de composés organiques de l'aluminium thérapeutiquement actifs CH447160A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB30431/59A GB911632A (en)	1959-09-07	1959-09-07	Improvements relating to organic aluminium compounds

Publications (1)

Publication Number	Publication Date
CH447160A true CH447160A (fr)	1967-11-30

Family

ID=10307574

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1007360A CH447160A (fr)	1959-09-07	1960-09-06	Procédé de préparation de composés organiques de l'aluminium thérapeutiquement actifs

Country Status (6)

Country	Link
CH (1)	CH447160A (da)
DE (1)	DE1179204B (da)
DK (1)	DK113718B (da)
FR (1)	FR1466207A (da)
GB (1)	GB911632A (da)
SE (1)	SE309045B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108707129A (zh)	2012-07-27	2018-10-26	太阳化学公司	作为油墨中的光引发剂和光敏剂的香豆素酮

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE569946C (de) *	1931-03-25	1933-02-09	I G Farbenindustrie Akt Ges	Verfahren zur Herstellung der Aluminiumsalze von Carbonsaeuren

1959
- 1959-09-07 GB GB30431/59A patent/GB911632A/en not_active Expired
1960
- 1960-09-06 SE SE8503/60A patent/SE309045B/xx unknown
- 1960-09-06 CH CH1007360A patent/CH447160A/fr unknown
- 1960-09-07 DK DK354360AA patent/DK113718B/da unknown
- 1960-09-07 DE DEH40363A patent/DE1179204B/de active Pending
- 1960-09-07 FR FR838034A patent/FR1466207A/fr not_active Expired

Also Published As

Publication number	Publication date
GB911632A (en)	1962-11-28
FR1466207A (fr)	1967-01-20
DE1179204B (de)	1964-10-08
SE309045B (da)	1969-03-10
DK113718B (da)	1969-04-21

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CH458317A (fr)	1968-06-30	Procédé de préparation de composés organiques de l'aluminium
CH447160A (fr)	1967-11-30	Procédé de préparation de composés organiques de l'aluminium thérapeutiquement actifs
EP0443918B1 (fr)	1996-06-26	Nouveaux dérivés de la 20,21-dinoréburnaménine, leur procédé de préparation et les nouveaux intermédiaires ainsi obtenus, leur application comme médicaments et les compositions les renfermant
CH447159A (fr)	1967-11-30	Procédé de préparation de composés organiques de l'aluminium
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CH653332A5 (fr)	1985-12-31	Derives du tetrahydropyridin-4-yl indole et leurs sels, leur preparation et les medicaments les renfermant.
EP0012072B1 (fr)	1984-05-16	Bêta-lactones dérivées de l'acide 2-hydroxy cyclopentane carboxylique, procédé pour leur préparation et compositions pharmaceutiques les renfermant
EP0065907B1 (fr)	1984-12-05	((Tétra- et hexahydro pyridyl-4)-2 éthyl)-3 indoles et leur utilisation comme médicaments
CA1060020A (fr)	1979-08-07	Procede de preparation de nouveaux derives de la dibenzo/b,c/ thiepine et leurs sels
FR2529891A1 (fr)	1984-01-13	Derives du pyridyl-3 alcoxy-5 pyrazole, procede de preparation et application en therapeutique
JPH0514708B2 (da)	1993-02-25
EP0082040B1 (fr)	1986-01-15	Dérivés de diaza-3,7a cyclohepta(j,k)fluorènes, leur préparation et leur application en thérapeutique
EP0300850B1 (fr)	1992-08-26	Dérivés de 1-arylsulfonyl 1,5-dihydro 2H-pyrrol-2-one, leurs procédé et intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant
CA1116089A (fr)	1982-01-12	Compositions pharmaceutiques comprenant des medicaments a base de derives de la quinoleine
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