CH515207A - Verfahren zur Herstellung von neuen Bis-(p-Chlorphenoxy)-essigsäureestern - Google Patents

Verfahren zur Herstellung von neuen Bis-(p-Chlorphenoxy)-essigsäureestern

Info

Publication number: CH515207A
Authority: CH; Switzerland
Prior art keywords: chlorophenoxy; formula; bis; compounds; acetic acid
Prior art date: 1966-06-27

Application number

CH836567A

Other languages

German (de)

English (en)

Inventor

G Griot Rudolf

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.)

1966-06-27

Filing date

1967-06-13

Publication date

1971-11-15

1967-06-13 Application filed by Sandoz Ag filed Critical Sandoz Ag

1971-11-15 Publication of CH515207A publication Critical patent/CH515207A/de

Links

150000002148 esters Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 9
ZKNSZZXBPSICFK-UHFFFAOYSA-N 2,2-bis(4-chlorophenoxy)acetic acid Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)O)OC1=CC=C(Cl)C=C1 ZKNSZZXBPSICFK-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
150000001340 alkali metals Chemical group 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 8
239000000203 mixture Substances 0.000 abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
229910000027 potassium carbonate Inorganic materials 0.000 abstract description 4
229910000029 sodium carbonate Inorganic materials 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
239000002830 appetite depressant Substances 0.000 abstract description 2
238000005886 esterification reaction Methods 0.000 abstract description 2
DZNRSYLSASWKDV-UHFFFAOYSA-N propan-2-yl 2,2-bis(4-chlorophenoxy)acetate Chemical compound C(C)(C)OC(C(OC1=CC=C(C=C1)Cl)OC1=CC=C(C=C1)Cl)=O DZNRSYLSASWKDV-UHFFFAOYSA-N 0.000 abstract description 2
230000032050 esterification Effects 0.000 abstract 1
230000000055 hyoplipidemic effect Effects 0.000 abstract 1
230000000871 hypocholesterolemic effect Effects 0.000 abstract 1
235000015320 potassium carbonate Nutrition 0.000 abstract 1
235000017550 sodium carbonate Nutrition 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
-1 potassium carbonate Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
DXXHHEGZUCEQCJ-UHFFFAOYSA-N (4-chlorophenyl) ethaneperoxoate Chemical compound CC(=O)OOC1=CC=C(Cl)C=C1 DXXHHEGZUCEQCJ-UHFFFAOYSA-N 0.000 description 2
GZKWLSPCSGVBPT-UHFFFAOYSA-N 2,2-bis(4-chlorophenoxy)acetyl chloride Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)Cl)OC1=CC=C(Cl)C=C1 GZKWLSPCSGVBPT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000007529 inorganic bases 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
AKJMRXYFFBGXNQ-UHFFFAOYSA-N CC(C)(C)OC(C(OC(C=C1)=CC=C1Cl)OC(C=C1)=CC=C1Cl)=O Chemical compound CC(C)(C)OC(C(OC(C=C1)=CC=C1Cl)OC(C=C1)=CC=C1Cl)=O AKJMRXYFFBGXNQ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 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 description 1
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 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
229920001214 Polysorbate 60 Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 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
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Emergency Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH836567A 1966-06-27 1967-06-13 Verfahren zur Herstellung von neuen Bis-(p-Chlorphenoxy)-essigsäureestern CH515207A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US56087466A	1966-06-27	1966-06-27

Publications (1)

Publication Number	Publication Date
CH515207A true CH515207A (de)	1971-11-15

Family

ID=24239719

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH836567A CH515207A (de)	1966-06-27	1967-06-13	Verfahren zur Herstellung von neuen Bis-(p-Chlorphenoxy)-essigsäureestern

Country Status (5)

Country	Link
CH (1)	CH515207A (fr)
DE (1)	DE1593996A1 (fr)
ES (1)	ES342330A1 (fr)
FR (1)	FR7169M (fr)
GB (1)	GB1190434A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3952096A (en) *	1973-06-15	1976-04-20	Bristol-Myers Company	Mixture of calcium carbonate and calcium-α-p-chlorophenoxyisobutyrate as an antihyperlipemic agent

1967
- 1967-06-13 CH CH836567A patent/CH515207A/de not_active IP Right Cessation
- 1967-06-22 DE DE19671593996 patent/DE1593996A1/de active Pending
- 1967-06-23 GB GB2784867A patent/GB1190434A/en not_active Expired
- 1967-06-26 ES ES342330A patent/ES342330A1/es not_active Expired
- 1967-09-22 FR FR121869A patent/FR7169M/fr not_active Expired

Also Published As

Publication number	Publication date
ES342330A1 (es)	1968-10-16
GB1190434A (en)	1970-05-06
FR7169M (fr)	1969-08-11
DE1593996A1 (de)	1971-04-01

Legal Events

Date	Code	Title	Description
1976-01-15	PL	Patent ceased

Publication	Publication Date	Title
DE1695139A1 (de)	1970-12-17	Verfahren zur Herstellung von Imidazolderivaten
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CH643829A5 (de)	1984-06-29	Verfahren zur herstellung von 2,5-bis(2,2,2-trifluoraethoxy)-n-(2-piperidylmethyl)benzamid.
DE1174770B (de)	1964-07-30	Verfahren zur Herstellung von Polyincarbonsaeuren und deren Estern
DE2505106A1 (de)	1975-08-21	Neue hydroaromatische verbindungen
DE2708182C3 (de)	1979-08-30	Verfahren zur Herstellung von Acylcyaniden
CH515207A (de)	1971-11-15	Verfahren zur Herstellung von neuen Bis-(p-Chlorphenoxy)-essigsäureestern
AT296269B (de)	1972-02-10	Verfahren zur Herstellung von neuen Bis-(p-chlorphenoxy)-essigsäureestern
CH610330A5 (en)	1979-04-12	Process for the preparation of novel ergopeptins
DE1793385B2 (de)	1978-09-21	Verfahren zur Fluorierung von ungesättigten organischen Verbindungen mit einem Hypofluorit
DE2501861C2 (de)	1984-02-09	3,4,6-Tri-O-acyl-2-desoxy-2-nicotinoylamino-1-O-nicotinoyl-&beta;-D-glucopyranosen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate
DE2412323C3 (de)	1978-11-09	1,2-Diphenyl-äthanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
AT347423B (de)	1978-12-27	Verfahren zur herstellung von neuen 7- aminobenzocycloheptenen und von deren salzen
AT344148B (de)	1978-07-10	Verfahren zur herstellung von 2,6-dihydroxycineol
DE2040555C3 (de)	1980-07-03	Verfahren zur Herstellung von Chlorhydrinen
AT273387B (de)	1969-08-11	Verfahren zur Herstellung von neuen Cholesterinderivaten sowie von deren Säureadditionssalzen
AT378190B (de)	1985-06-25	Verfahren zur herstellung von neuen oximen
AT337167B (de)	1977-06-10	Verfahren zur herstellung neuer carbonsaure- (3-(4-biphenylyl)-1-butyl)-ester
US3267148A (en)	1966-08-16	Chemical processes
CH529755A (de)	1972-10-31	Verfahren zur Herstellung des neuen 4-Benzoyl-4-hydroxy-3-phenylpiperidins
DE1054088B (de)	1959-04-02	Verfahren zur Herstellung von Dehydrierungsprodukten des Piperidins und Pyrrolidins
CH526546A (de)	1972-08-15	Verfahren zur Herstellung neuer 3-Phenylpiperidinderivate
DE2809183A1 (de)	1978-09-28	3-(1-carboxy-alkoxy)-pyrazol-derivate und verfahren zu ihrer herstellung
DE2439089A1 (de)	1975-03-13	5-substituierte cyclopent-2-en-1-one und verfahren zur herstellung von 2-substituierten cyclopent-2-en-1-onen
CH481038A (de)	1969-11-15	Verfahren zur Herstellung neuer Malonsäure-Derivate