CH497367A - Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung - Google Patents

Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung

Info

Publication number: CH497367A
Authority: CH; Switzerland
Prior art keywords: methyl; acid; benzene; mixture; chloride
Prior art date: 1964-04-06

Application number

CH433965A

Other languages

German (de)

English (en)

Inventor

Nelson Brown Carter

Marvin Van Heyningen Earle

Original Assignee

Lilly Co Eli

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.)

1964-04-06

Filing date

1965-03-30

Publication date

1970-10-15

1964-04-06 Priority claimed from US357771A external-priority patent/US3342860A/en

1965-03-30 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1970-10-15 Publication of CH497367A publication Critical patent/CH497367A/de

Links

235000013985 cinnamic acid Nutrition 0.000 title abstract description 6
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 title abstract description 6
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title abstract 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 title abstract 2
229930016911 cinnamic acid Natural products 0.000 title abstract 2
230000000842 anti-protozoal effect Effects 0.000 title 1
229940036589 antiprotozoals Drugs 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 15
-1 pyrrolidino, morpholino Chemical group 0.000 claims abstract description 12
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims abstract description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
XWGXFOVSOYMSGT-UHFFFAOYSA-N n-propan-2-ylcyclopropanamine Chemical class CC(C)NC1CC1 XWGXFOVSOYMSGT-UHFFFAOYSA-N 0.000 claims abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 146
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
238000000034 method Methods 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 37
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 34
238000003756 stirring Methods 0.000 claims description 19
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 18
238000004458 analytical method Methods 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 18
239000003208 petroleum Substances 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
239000007858 starting material Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 14
238000002844 melting Methods 0.000 claims description 14
230000008018 melting Effects 0.000 claims description 14
239000000047 product Substances 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 13
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 12
239000002480 mineral oil Substances 0.000 claims description 12
239000012044 organic layer Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 9
239000010410 layer Substances 0.000 claims description 9
235000010446 mineral oil Nutrition 0.000 claims description 9
238000001953 recrystallisation Methods 0.000 claims description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
VUGQIIQFXCXZJU-UHFFFAOYSA-N 3,4,5-trimethoxyacetophenone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1OC VUGQIIQFXCXZJU-UHFFFAOYSA-N 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
239000003610 charcoal Substances 0.000 claims description 5
APEJMQOBVMLION-UHFFFAOYSA-N cinnamic acid amide Natural products NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims description 5
150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 5
238000001704 evaporation Methods 0.000 claims description 5
230000008020 evaporation Effects 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims description 5
FNFSOYGIQWSIEX-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(OC)=C(OC)C(OC)=C1 FNFSOYGIQWSIEX-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
239000000706 filtrate Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 claims description 3
238000010792 warming Methods 0.000 claims description 3
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
PYTANBUURZFYHD-UHFFFAOYSA-N 2-methylcyclopropan-1-amine Chemical compound CC1CC1N PYTANBUURZFYHD-UHFFFAOYSA-N 0.000 claims description 2
SSSXOHQWSQFJNX-UHFFFAOYSA-N 3-(3,4,5-trimethoxyphenyl)but-2-enoic acid Chemical compound COC1=CC(C(C)=CC(O)=O)=CC(OC)=C1OC SSSXOHQWSQFJNX-UHFFFAOYSA-N 0.000 claims description 2
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 2
YTFVRYKNXDADBI-UHFFFAOYSA-N O-Methylsinapic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 claims description 2
238000010828 elution Methods 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
239000003701 inert diluent Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
VEBLEROFGPOMPB-UHFFFAOYSA-N n-methylcyclopropanamine Chemical compound CNC1CC1 VEBLEROFGPOMPB-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
239000000377 silicon dioxide Substances 0.000 claims description 2
239000006188 syrup Substances 0.000 claims description 2
235000020357 syrup Nutrition 0.000 claims description 2
238000004809 thin layer chromatography Methods 0.000 claims description 2
239000000243 solution Substances 0.000 claims 13
230000001419 dependent effect Effects 0.000 claims 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
239000007864 aqueous solution Substances 0.000 claims 2
230000007062 hydrolysis Effects 0.000 claims 2
238000006460 hydrolysis reaction Methods 0.000 claims 2
229910052500 inorganic mineral Inorganic materials 0.000 claims 2
239000011707 mineral Substances 0.000 claims 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
238000005481 NMR spectroscopy Methods 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 3
241000248418 Tetrahymena pyriformis Species 0.000 abstract description 2
230000036772 blood pressure Effects 0.000 abstract description 2
208000007379 Muscle Hypotonia Diseases 0.000 abstract 1
125000006431 methyl cyclopropyl group Chemical group 0.000 abstract 1
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
241000700159 Rattus Species 0.000 description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
229940074391 gallic acid Drugs 0.000 description 2
235000004515 gallic acid Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
230000002936 tranquilizing effect Effects 0.000 description 2
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
ZYDQSPYFLQSONW-UHFFFAOYSA-N 2,3-dimethoxy-3-(2-methoxyphenyl)prop-2-enoic acid Chemical compound COC(C(O)=O)=C(OC)C1=CC=CC=C1OC ZYDQSPYFLQSONW-UHFFFAOYSA-N 0.000 description 1
GTQLBNNLAYDNKC-UHFFFAOYSA-N 2-methyl-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=C(C)C(O)=O)=CC(OC)=C1OC GTQLBNNLAYDNKC-UHFFFAOYSA-N 0.000 description 1
RURHILYUWQEGOS-UHFFFAOYSA-N 3-(4-methylphenyl)prop-2-enoic acid Chemical class CC1=CC=C(C=CC(O)=O)C=C1 RURHILYUWQEGOS-UHFFFAOYSA-N 0.000 description 1
CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
LOUMGDLTGMVMTK-UHFFFAOYSA-N O(C)C(CC(=O)C1=CC=CC=C1)(OC)OC Chemical compound O(C)C(CC(=O)C1=CC=CC=C1)(OC)OC LOUMGDLTGMVMTK-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UJYLYGDHTIVYRI-UHFFFAOYSA-N cadmium(2+);ethane Chemical compound [Cd+2].[CH2-]C.[CH2-]C UJYLYGDHTIVYRI-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
230000003010 neurosedative effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH433965A 1964-04-06 1965-03-30 Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung CH497367A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US357771A US3342860A (en)	1961-09-09	1964-04-06	N-substituted cinnamamides

Publications (1)

Publication Number	Publication Date
CH497367A true CH497367A (de)	1970-10-15

Family

ID=23406962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH433965A CH497367A (de)	1964-04-06	1965-03-30	Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung

Country Status (6)

Country	Link
BE (1)	BE662156A (fr)
CH (1)	CH497367A (fr)
DE (1)	DE1518753A1 (fr)
ES (1)	ES311043A1 (fr)
FR (1)	FR4305M (fr)
GB (1)	GB1104995A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3940439A (en) *	1973-11-14	1976-02-24	G. D. Searle & Co.	Acid chloride synthesis
US4440784A (en) *	1981-02-05	1984-04-03	Kanegafuchi Chemical Industry Company, Ltd.	Anti-inflammatory, analgesic, and antipyretic pharmaceutical composition
CS244440B2 (en) *	1983-02-28	1986-07-17	Celamerck Gmbh & Co Kg	Method of acrylic acids' new amides production
FR2559763B1 (fr) *	1984-02-22	1986-07-11	Centre Nat Rech Scient	Composes possedant, notamment, des proprietes inhibitrices vis-a-vis de la lignification dans les vegetaux et procede pour la reduction de leur taux de lignine
DE3525623A1 (de) *	1985-07-18	1987-01-22	Celamerck Gmbh & Co Kg	Fungizid wirksame acrylsaeureamide
GB8729109D0 (en) *	1987-12-14	1988-01-27	Greig Smith P W	Improvements in/relating to avian control
US5196451A (en) *	1987-12-14	1993-03-23	National Research Development Corporation	Avian control
GB8829166D0 (en) *	1988-12-14	1989-01-25	Greig Smith Peter W	Improvements in or relating to rodent control

1965
- 1965-03-26 ES ES0311043A patent/ES311043A1/es not_active Expired
- 1965-03-30 CH CH433965A patent/CH497367A/de not_active IP Right Cessation
- 1965-03-30 GB GB1349565A patent/GB1104995A/en not_active Expired
- 1965-04-05 DE DE19651518753 patent/DE1518753A1/de active Pending
- 1965-04-06 FR FR12105A patent/FR4305M/fr not_active Expired
- 1965-04-06 BE BE662156D patent/BE662156A/xx unknown

Also Published As

Publication number	Publication date
ES311043A1 (es)	1965-08-16
DE1518753A1 (de)	1969-06-12
FR4305M (fr)	1966-07-25
GB1104995A (en)	1968-03-06
BE662156A (fr)	1965-10-06

Legal Events

Date	Code	Title	Description
1971-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE2611690C2 (fr)	1992-01-16
CH354435A (de)	1961-05-31	Verfahren zur Herstellung ungesättigter Carbonsäuren
CH633515A5 (de)	1982-12-15	Substituierte phenylessigsaeurederivate und verfahren zu ihrer herstellung.
CH640224A5 (de)	1983-12-30	2-pyrrolidonderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von 4-aminohex-5-ensaeure.
CH497367A (de)	1970-10-15	Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung
EP0125506A1 (fr)	1984-11-21	(Dichloro-2,6-trifluorométhyl-4-phénoxy)-5-nitro-2-benzaldéhyde-diacétacylal
DE2735036C2 (de)	1983-10-13	Verfahren zur Herstellung optisch aktiver, N-substituierter Pyrrolidine
DE1670222C3 (de)	1979-04-05	a-(Benzyloxycarbonyl)-thienyunethylpenicilline und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
DE2623226C2 (de)	1986-03-20	N-Benzyl-2,2-dimethoxy-acetamide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE3128676C2 (de)	1983-12-01	P-Isobutylphenylpropionsäureamide, ihre Herstellung und diese enthaltende Arzneimittel
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CH610330A5 (en)	1979-04-12	Process for the preparation of novel ergopeptins
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