IL44224A - Bis-(4-alkanoylbenzyl) acetic acid derivatives their production and pharmaceutical compositions containing them - Google Patents

Bis-(4-alkanoylbenzyl) acetic acid derivatives their production and pharmaceutical compositions containing them

Info

Publication number: IL44224A
Authority: IL; Israel
Prior art keywords: formula; compound; bis; signifies; hydrogen
Prior art date: 1973-02-20

Application number

IL44224A

Other languages

English (en)

Other versions

IL44224A0 (en

Original Assignee

Sandoz 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.)

1973-02-20

Filing date

1974-02-18

Publication date

1977-11-30

1974-02-18 Application filed by Sandoz Ag filed Critical Sandoz Ag

1974-05-16 Publication of IL44224A0 publication Critical patent/IL44224A0/xx

1977-11-30 Publication of IL44224A publication Critical patent/IL44224A/en

Links

238000004519 manufacturing process Methods 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000001242 acetic acid derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 49
238000000034 method Methods 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052784 alkaline earth metal Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
230000000911 decarboxylating effect Effects 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
MLWGRIDONXNPHA-UHFFFAOYSA-N COC(C(C(=O)OC)(CC1=CC=C(C=C1)C(C(C)(C)C)=O)CC1=CC=C(C=C1)C(C(C)(C)C)=O)=O Chemical compound COC(C(C(=O)OC)(CC1=CC=C(C=C1)C(C(C)(C)C)=O)CC1=CC=C(C=C1)C(C(C)(C)C)=O)=O MLWGRIDONXNPHA-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
235000012000 cholesterol Nutrition 0.000 description 3
IVRFWIFJCNFJAS-UHFFFAOYSA-N diethyl 2,2-bis[[4-(2,2-dimethylpropanoyl)phenyl]methyl]propanedioate Chemical compound C=1C=C(C(=O)C(C)(C)C)C=CC=1CC(C(=O)OCC)(C(=O)OCC)CC1=CC=C(C(=O)C(C)(C)C)C=C1 IVRFWIFJCNFJAS-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZYWGAHRBGCEFAO-UHFFFAOYSA-N 2,2-dimethyl-1-(4-methylphenyl)propan-1-one Chemical compound CC1=CC=C(C(=O)C(C)(C)C)C=C1 ZYWGAHRBGCEFAO-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000000055 hyoplipidemic effect Effects 0.000 description 2
239000003999 initiator Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-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
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
RBLAOGBEJPHFHW-UHFFFAOYSA-N 2-benzyl-3-phenylpropanoic acid Chemical class C=1C=CC=CC=1CC(C(=O)O)CC1=CC=CC=C1 RBLAOGBEJPHFHW-UHFFFAOYSA-N 0.000 description 1
MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
DVDVYYQGYMRFCC-UHFFFAOYSA-N 3-[4-(2,2-dimethylpropanoyl)phenyl]-2-[[4-(2,2-dimethylpropanoyl)phenyl]methyl]propanoic acid Chemical compound C1=CC(C(=O)C(C)(C)C)=CC=C1CC(C(O)=O)CC1=CC=C(C(=O)C(C)(C)C)C=C1 DVDVYYQGYMRFCC-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000005750 Copper hydroxide Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
-1 alkali metal alkoxides Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910001956 copper hydroxide Inorganic materials 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
159000000003 magnesium salts Chemical group 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005303 weighing Methods 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
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- 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
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
- 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
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL44224A 1973-02-20 1974-02-18 Bis-(4-alkanoylbenzyl) acetic acid derivatives their production and pharmaceutical compositions containing them IL44224A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US33389273A	1973-02-20	1973-02-20
US40322573A	1973-10-03	1973-10-03

Publications (2)

Publication Number	Publication Date
IL44224A0 IL44224A0 (en)	1974-05-16
IL44224A true IL44224A (en)	1977-11-30

Family

ID=26988943

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL44224A IL44224A (en)	1973-02-20	1974-02-18	Bis-(4-alkanoylbenzyl) acetic acid derivatives their production and pharmaceutical compositions containing them

Country Status (16)

Country	Link
JP (1)	JPS5029534A (xx)
AT (1)	AT346308B (xx)
CA (1)	CA1043807A (xx)
CH (1)	CH591418A5 (xx)
CS (1)	CS170510B2 (xx)
DD (1)	DD110033A5 (xx)
DE (1)	DE2406881A1 (xx)
ES (1)	ES423376A1 (xx)
FR (1)	FR2218106B1 (xx)
GB (2)	GB1453643A (xx)
HU (1)	HU168102B (xx)
IE (1)	IE39419B1 (xx)
IL (1)	IL44224A (xx)
NL (1)	NL7402093A (xx)
PH (1)	PH10682A (xx)
SE (1)	SE399554B (xx)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3607728A1 (de) *	1986-01-25	1987-07-30	Telefonbau & Normalzeit Gmbh	Endgeraet einer fernmeldevermittlungsanlage
US7485951B2 (en)	2001-10-26	2009-02-03	Entorian Technologies, Lp	Modularized die stacking system and method
US6940729B2 (en)	2001-10-26	2005-09-06	Staktek Group L.P.	Integrated circuit stacking system and method
US6914324B2 (en)	2001-10-26	2005-07-05	Staktek Group L.P.	Memory expansion and chip scale stacking system and method
US7371609B2 (en)	2001-10-26	2008-05-13	Staktek Group L.P.	Stacked module systems and methods
US7081373B2 (en)	2001-12-14	2006-07-25	Staktek Group, L.P.	CSP chip stack with flex circuit
US7309914B2 (en)	2005-01-20	2007-12-18	Staktek Group L.P.	Inverted CSP stacking system and method

1974
- 1974-02-08 CH CH176774A patent/CH591418A5/xx not_active IP Right Cessation
- 1974-02-11 SE SE7401786A patent/SE399554B/xx unknown
- 1974-02-13 DE DE19742406881 patent/DE2406881A1/de not_active Withdrawn
- 1974-02-15 NL NL7402093A patent/NL7402093A/xx not_active Application Discontinuation
- 1974-02-15 GB GB695374A patent/GB1453643A/en not_active Expired
- 1974-02-15 GB GB2533876A patent/GB1453644A/en not_active Expired
- 1974-02-18 AT AT125874A patent/AT346308B/de not_active IP Right Cessation
- 1974-02-18 ES ES423376A patent/ES423376A1/es not_active Expired
- 1974-02-18 DD DD176622A patent/DD110033A5/xx unknown
- 1974-02-18 CA CA192,776A patent/CA1043807A/en not_active Expired
- 1974-02-18 CS CS1168A patent/CS170510B2/cs unknown
- 1974-02-18 JP JP49018655A patent/JPS5029534A/ja active Pending
- 1974-02-18 HU HUSA2595A patent/HU168102B/hu unknown
- 1974-02-18 IL IL44224A patent/IL44224A/en unknown
- 1974-02-19 IE IE333/74A patent/IE39419B1/xx unknown
- 1974-02-20 PH PH15530A patent/PH10682A/en unknown
- 1974-02-20 FR FR7405671A patent/FR2218106B1/fr not_active Expired

Also Published As

Publication number	Publication date
HU168102B (xx)	1976-02-28
FR2218106A1 (xx)	1974-09-13
JPS5029534A (xx)	1975-03-25
DE2406881A1 (de)	1974-08-29
CA1043807A (en)	1978-12-05
ES423376A1 (es)	1976-09-16
PH10682A (en)	1977-08-10
CH591418A5 (xx)	1977-09-15
IE39419L (en)	1974-08-20
IE39419B1 (en)	1978-10-11
AT346308B (de)	1978-11-10
DD110033A5 (xx)	1974-12-05
FR2218106B1 (xx)	1978-01-13
CS170510B2 (xx)	1976-08-27
GB1453643A (en)	1976-10-27
AU6577274A (en)	1975-08-21
IL44224A0 (en)	1974-05-16
SE399554B (sv)	1978-02-20
NL7402093A (xx)	1974-08-22
ATA125874A (de)	1978-03-15
GB1453644A (en)	1976-10-27

Publication	Publication Date	Title
US3978132A (en)	1976-08-31	Acyl benzyl ethers
US4198425A (en)	1980-04-15	Mevalonolactone derivatives
Larsson et al.	1972	Preparation and alkylation of substituted β-hydroxydithiocinnamic acids
CA1127177A (en)	1982-07-06	Phenylacetic acid derivatives
US4032644A (en)	1977-06-28	Isoxazolyl benzoic acids
US4057573A (en)	1977-11-08	New hydroaromatic compounds
IL44224A (en)	1977-11-30	Bis-(4-alkanoylbenzyl) acetic acid derivatives their production and pharmaceutical compositions containing them
US4235780A (en)	1980-11-25	Derivatives of 2H-pyran-2-one
US3870751A (en)	1975-03-11	Substituted phenyl acetic acids
US3907878A (en)	1975-09-23	Acyl substituted phenyl propionic acids
US3884961A (en)	1975-05-20	Bis-(substituted benzyl) malonic acid esters
US3927079A (en)	1975-12-16	Bis-substituted or unsubstituted-p-benzoylbenzyl acetic acids
US3962320A (en)	1976-06-08	Bis-substituted benzyl acetic acids
US4015010A (en)	1977-03-29	Alkanoyl substituted benzoic acids and esters
US3880932A (en)	1975-04-29	4-(2-Naphthyl)-4-alkyl-3-buten-2-ones
US4129658A (en)	1978-12-12	4-Styryl-hexahydro-4-indolinols
US3996286A (en)	1976-12-07	α-Bromo-pivaloyl toluenes
US3558626A (en)	1971-01-26	2-(4 - (diphenyl-2-pyrimidinyl)phenoxy) lower aliphatic monocarbocyclic acids and esters
CS196445B2 (en)	1980-03-31	Method of producing novel derivatives of indolyl-acetic acid and salts of the same
US3681365A (en)	1972-08-01	Derivatives of acetic acid
US4213905A (en)	1980-07-22	Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid salts
US4421928A (en)	1983-12-20	4-Methyl-3-formyl-pentanoic acid esters
US4247715A (en)	1981-01-27	2-Alkynyl-5-indanyloxyacetic acids
US4342694A (en)	1982-08-03	Processes for producing pyrethroid insecticide intermediates
US4011344A (en)	1977-03-08	Iminodimethylene di-tert-alkylophenones and phenols