SU563119A3 - Способ получени первичных аминоациланилидов или их солей, или оптических антиподов - Google Patents

Способ получени первичных аминоациланилидов или их солей, или оптических антиподов

Info

Publication number: SU563119A3
Authority: SU; USSR - Soviet Union
Prior art keywords: methyl; hydrogen; solution; mixture; ether
Prior art date: 1973-01-08

Application number

SU1982938A

Other languages

English (en)

Russian (ru)

Inventor

Николь Бойс Роберт

Рэндаль Дюс Бенджамин

Ричард Смит Эмиль

Уильян Байрнс Юджин

Original Assignee

Астра Фармасьютикал Продактс Инк (Фирма)

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.)

1973-01-08

Filing date

1974-01-04

Publication date

1977-06-25

1974-01-04 Application filed by Астра Фармасьютикал Продактс Инк (Фирма) filed Critical Астра Фармасьютикал Продактс Инк (Фирма)

1977-06-25 Application granted granted Critical

1977-06-25 Publication of SU563119A3 publication Critical patent/SU563119A3/ru

Links

238000000034 method Methods 0.000 title claims 6
150000003839 salts Chemical class 0.000 title claims 6
230000003287 optical effect Effects 0.000 title claims 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 34
239000001257 hydrogen Substances 0.000 claims 27
229910052739 hydrogen Inorganic materials 0.000 claims 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 25
239000000203 mixture Substances 0.000 claims 22
239000000243 solution Substances 0.000 claims 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 17
150000002431 hydrogen Chemical group 0.000 claims 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 11
238000002360 preparation method Methods 0.000 claims 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
-1 amino-2-ethyl Chemical group 0.000 claims 7
229910021529 ammonia Inorganic materials 0.000 claims 7
150000001875 compounds Chemical class 0.000 claims 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
239000000460 chlorine Substances 0.000 claims 6
229910052801 chlorine Inorganic materials 0.000 claims 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
238000001953 recrystallisation Methods 0.000 claims 6
239000002904 solvent Substances 0.000 claims 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
239000000284 extract Substances 0.000 claims 5
239000002244 precipitate Substances 0.000 claims 5
239000000047 product Substances 0.000 claims 5
238000010992 reflux Methods 0.000 claims 5
229920006395 saturated elastomer Polymers 0.000 claims 5
238000003756 stirring Methods 0.000 claims 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
239000000706 filtrate Substances 0.000 claims 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 4
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
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 claims 3
239000007864 aqueous solution Substances 0.000 claims 3
239000002585 base Substances 0.000 claims 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
229910052794 bromium Inorganic materials 0.000 claims 3
238000006243 chemical reaction Methods 0.000 claims 3
239000007789 gas Substances 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
239000011541 reaction mixture Substances 0.000 claims 3
239000011734 sodium Substances 0.000 claims 3
229910052708 sodium Inorganic materials 0.000 claims 3
ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
229960000583 acetic acid Drugs 0.000 claims 2
239000003929 acidic solution Substances 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
239000012362 glacial acetic acid Substances 0.000 claims 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
239000011630 iodine Substances 0.000 claims 2
229910052740 iodine Inorganic materials 0.000 claims 2
IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 claims 2
239000003208 petroleum Substances 0.000 claims 2
239000012071 phase Substances 0.000 claims 2
229940072033 potash Drugs 0.000 claims 2
235000015320 potassium carbonate Nutrition 0.000 claims 2
YQBUUEDECWZPTJ-UHFFFAOYSA-N (2,6-dimethyl-4-propoxyphenyl)-phenyldiazene Chemical compound CC1=CC(OCCC)=CC(C)=C1N=NC1=CC=CC=C1 YQBUUEDECWZPTJ-UHFFFAOYSA-N 0.000 claims 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims 1
ZVBAPPZCAFKUKN-UHFFFAOYSA-N 2,6-dimethyl-4-propoxyaniline Chemical compound CCCOC1=CC(C)=C(N)C(C)=C1 ZVBAPPZCAFKUKN-UHFFFAOYSA-N 0.000 claims 1
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims 1
JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims 1
WDRCPKDLZOQCFU-UHFFFAOYSA-N 2-methyl-n-phenylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC=C1 WDRCPKDLZOQCFU-UHFFFAOYSA-N 0.000 claims 1
FRXLFVNGTPQFEJ-UHFFFAOYSA-N 3-bromopropanoyl bromide Chemical compound BrCCC(Br)=O FRXLFVNGTPQFEJ-UHFFFAOYSA-N 0.000 claims 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
206010016717 Fistula Diseases 0.000 claims 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
241000218657 Picea Species 0.000 claims 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 1
XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 claims 1
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
235000001014 amino acid Nutrition 0.000 claims 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 claims 1
230000000703 anti-shock Effects 0.000 claims 1
239000008346 aqueous phase Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
238000009835 boiling Methods 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
229940106681 chloroacetic acid Drugs 0.000 claims 1
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
239000012043 crude product Substances 0.000 claims 1
239000013078 crystal Substances 0.000 claims 1
229960001270 d- tartaric acid Drugs 0.000 claims 1
238000000354 decomposition reaction Methods 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
238000004821 distillation Methods 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
235000013601 eggs Nutrition 0.000 claims 1
239000012259 ether extract Substances 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
238000000605 extraction Methods 0.000 claims 1
238000001125 extrusion Methods 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
230000003890 fistula Effects 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
238000004817 gas chromatography Methods 0.000 claims 1
239000008103 glucose Substances 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 1
239000000463 material Substances 0.000 claims 1
239000000155 melt Substances 0.000 claims 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
OMQIAXSKJOFQAN-UHFFFAOYSA-N n,n-dimethyl-4-propoxyaniline Chemical compound CCCOC1=CC=C(N(C)C)C=C1 OMQIAXSKJOFQAN-UHFFFAOYSA-N 0.000 claims 1
TXBNRQUPSDOCGX-UHFFFAOYSA-N n-(2,6-dimethylphenyl)propanamide Chemical compound CCC(=O)NC1=C(C)C=CC=C1C TXBNRQUPSDOCGX-UHFFFAOYSA-N 0.000 claims 1
229910000027 potassium carbonate Inorganic materials 0.000 claims 1
235000011181 potassium carbonates Nutrition 0.000 claims 1
239000001294 propane Chemical group 0.000 claims 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
239000002994 raw material Substances 0.000 claims 1
239000001632 sodium acetate Substances 0.000 claims 1
235000017281 sodium acetate Nutrition 0.000 claims 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1982938A 1973-01-08 1974-01-04 Способ получени первичных аминоациланилидов или их солей, или оптических антиподов SU563119A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US32180073A	1973-01-08	1973-01-08
US32159073A	1973-01-08	1973-01-08

Publications (1)

Publication Number	Publication Date
SU563119A3 true SU563119A3 (ru)	1977-06-25

Family

ID=26983031

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1982938A SU563119A3 (ru)	1973-01-08	1974-01-04	Способ получени первичных аминоациланилидов или их солей, или оптических антиподов
SU752116825A SU656504A3 (ru)	1973-01-08	1975-03-24	Способ получени первичных аминоациланилидов или их солей

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU752116825A SU656504A3 (ru)	1973-01-08	1975-03-24	Способ получени первичных аминоациланилидов или их солей

Country Status (13)

Country	Link
JP (1)	JPS5833221B2 (fr)
AR (2)	AR205617A1 (fr)
CA (1)	CA1024528A (fr)
CH (2)	CH596148A5 (fr)
DD (1)	DD113749A5 (fr)
DE (1)	DE2400540A1 (fr)
ES (1)	ES422085A1 (fr)
FR (1)	FR2213065B1 (fr)
GB (1)	GB1461602A (fr)
HU (1)	HU166667B (fr)
IE (1)	IE39541B1 (fr)
NL (1)	NL7400167A (fr)
SU (2)	SU563119A3 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4098895A (en) *	1975-09-30	1978-07-04	Ciba-Geigy Corporation	Triazolylacetanilide compounds and microbicidal compositions
GB2267709A (en) *	1992-06-11	1993-12-15	Merck & Co Inc	Novel process for the preparation of alpha-aminoacylanilides

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB705460A (en) *	1951-02-26	1954-03-10	Astra Apotekarnes Kem Fab	Process for the preparation of aminoacetyl-anilides having alkyl substituents at theamino nitrogen and products thereof
DE939207C (de) *	1952-02-25	1956-02-16	Cilag Ag	Verfahren zur Herstellung von als Lokalanaesthetica verwendbaren basisch substituierten Fettsaeure-(2-chlor-6-methyl-aniliden) und ihren Salzen
DE1046059B (de) *	1952-06-12	1958-12-11	Astra Ab	Verfahren zur Herstellung von als lokalanaesthetische Mittel verwendbaren N-Alkyl-alaninaniliden
US2912460A (en) *	1952-08-18	1959-11-10	Hoechst Ag	Basically substituted carboxylic acid amides and a process of preparing them
FR1167026A (fr) *	1953-08-21	1958-11-19	Hoechst Ag	Amides d'acides à substituant basique et procédé de préparation de ces amides d'acides
DE1001277B (de) *	1953-11-10	1957-01-24	Leo Pharm Prod Ltd	Verfahren zur Herstellung von lokalanaesthetisch wirksamen Dialkylaminoacylaniliden
CH318077A (de) *	1954-01-29	1956-12-15	Cilag Ag	Verfahren zur Herstellung von B-Amino-buttersäureaniliden
DE1055541B (de) *	1954-11-01	1959-04-23	Geistlich Soehne Ag	Verfahren zur Herstellung von beta-Dialkylaminoacylaniliden
DE1028099B (de) *	1955-06-11	1958-04-17	Goesta Lennart Flemmert Dr Tec	Verfahren zur Herstellung von amorphem, feinverteiltem Siliciumdioxyd
DE1170856B (de) *	1960-10-11	1964-05-21	Degussa	Verfahren zur Herstellung von festhaftenden und loetfaehigen Metallschichten, insbesondere Silberschichten, auf keramischem Material, insbesondere Aluminiumoxydkoerpern
GB1028099A (en)	1965-03-30	1966-05-04	Tanabe Seiyaku Co	Substituted propionanilides
CH449042A (de) *	1965-04-02	1967-12-31	Tanabe Seiyaku Co	Verfahren zur Herstellung substituierter Propionanilide
SE337810B (fr)	1966-05-13	1971-08-23	Tanabe Seiyaku Co

1974
- 1974-01-01 AR AR251845A patent/AR205617A1/es active
- 1974-01-04 SU SU1982938A patent/SU563119A3/ru active
- 1974-01-07 FR FR7400485A patent/FR2213065B1/fr not_active Expired
- 1974-01-07 NL NL7400167A patent/NL7400167A/xx not_active Application Discontinuation
- 1974-01-07 HU HUAA763A patent/HU166667B/hu unknown
- 1974-01-07 DE DE2400540A patent/DE2400540A1/de not_active Ceased
- 1974-01-07 ES ES422085A patent/ES422085A1/es not_active Expired
- 1974-01-07 GB GB57074A patent/GB1461602A/en not_active Expired
- 1974-01-07 CH CH14174A patent/CH596148A5/xx not_active IP Right Cessation
- 1974-01-07 DD DD175865A patent/DD113749A5/xx unknown
- 1974-01-07 CA CA189,559A patent/CA1024528A/fr not_active Expired
- 1974-01-07 JP JP49005015A patent/JPS5833221B2/ja not_active Expired
- 1974-01-07 IE IE28/74A patent/IE39541B1/xx unknown
- 1974-01-07 CH CH1010277A patent/CH603556A5/xx not_active IP Right Cessation
1975
- 1975-03-24 SU SU752116825A patent/SU656504A3/ru active
- 1975-09-26 AR AR260567A patent/AR211695A1/es active

Also Published As

Publication number	Publication date
NL7400167A (fr)	1974-07-10
FR2213065A1 (fr)	1974-08-02
HU166667B (fr)	1975-05-28
DD113749A5 (fr)	1975-06-20
AU6424774A (en)	1975-07-10
CA1024528A (fr)	1978-01-17
AR211695A1 (es)	1978-02-28
FR2213065B1 (fr)	1978-01-06
JPS49116034A (fr)	1974-11-06
JPS5833221B2 (ja)	1983-07-18
CH596148A5 (fr)	1978-02-28
IE39541B1 (en)	1978-11-08
IE39541L (en)	1974-07-08
ES422085A1 (es)	1977-01-01
CH603556A5 (fr)	1978-08-31
GB1461602A (en)	1977-01-13
DE2400540A1 (de)	1974-08-15
AR205617A1 (es)	1976-05-21
SU656504A3 (ru)	1979-04-05

Publication	Publication Date	Title
Clarke et al.	1933	The action of formaldehyde on amines and amino acids1
US4058558A (en)	1977-11-15	Aromatic keto acids and derivatives having analgetic, antiinflammatory, and hypocholesterolemizing action
US4008323A (en)	1977-02-15	Method of reducing cholesterol using certain aromatic keto acids
SU865125A3 (ru)	1981-09-15	Способ получени производных имидазола или их солей
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