DE1545575C2 - N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazin - Google Patents
N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazinInfo
- Publication number
- DE1545575C2 DE1545575C2 DE1965A0051095 DEA0051095A DE1545575C2 DE 1545575 C2 DE1545575 C2 DE 1545575C2 DE 1965A0051095 DE1965A0051095 DE 1965A0051095 DE A0051095 A DEA0051095 A DE A0051095A DE 1545575 C2 DE1545575 C2 DE 1545575C2
- Authority
- DE
- Germany
- Prior art keywords
- homopiperazine
- bis
- chjo
- formula
- general formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229910052757 nitrogen Inorganic materials 0.000 title description 12
- 239000002253 acid Substances 0.000 claims description 12
- SJSOFNCYXJUNBT-UHFFFAOYSA-N Eudesmic acid Natural products COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 7
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- -1 trimethoxybenzoic acid halide Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 241000251730 Chondrichthyes Species 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 229940054334 silver cation Drugs 0.000 claims description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 4
- 239000003218 coronary vasodilator agent Substances 0.000 description 4
- 229960001989 prenylamine Drugs 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 206010022998 Irritability Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- WYKDLBVWXHCAJC-UHFFFAOYSA-N 3-[4-(3-hydroxypropyl)-1,4-diazepan-1-yl]propan-1-ol Chemical compound OCCCN1CCCN(CCCO)CC1 WYKDLBVWXHCAJC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- ZFQWBNSJGLZLCX-UHFFFAOYSA-N 3-[2-(3-hydroxypropylamino)ethylamino]propan-1-ol Chemical compound OCCCNCCNCCCO ZFQWBNSJGLZLCX-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- 241000699670 Mus sp. Species 0.000 description 1
- PXEWNFRBLQCQIT-UHFFFAOYSA-N O.Cl.Cl.N1CCNCCC1 Chemical compound O.Cl.Cl.N1CCNCCC1 PXEWNFRBLQCQIT-UHFFFAOYSA-N 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- KRQAMFQCSAJCRH-UHFFFAOYSA-N hexobendine Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCCN(C)CCN(C)CCCOC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 KRQAMFQCSAJCRH-UHFFFAOYSA-N 0.000 description 1
- 229960002212 hexobendine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/02—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965A0051095 DE1545575C2 (de) | 1965-12-16 | 1965-12-16 | N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazin |
| DK620966AA DK113291B (da) | 1965-12-16 | 1966-12-01 | Fremgangsmåde til fremstilling af coronardilatatorisk virksomme diazacycloalkanforbindelser eller syreadditionssalte deraf. |
| GB54090/66A GB1107470A (en) | 1965-12-16 | 1966-12-02 | Basic esters and a process for their production |
| IL27013A IL27013A (en) | 1965-12-16 | 1966-12-05 | Homologs of n,n'-bis(benzoyloxyalkyl)-piperazine,their preparation and pharmaceutical compositions containing them |
| AT1120566A AT275527B (de) | 1965-12-16 | 1966-12-05 | Verfahren zur Herstellung von neuen basischen Estern und ihren Salzen |
| US599724A US3532685A (en) | 1965-12-16 | 1966-12-07 | N,n' - alkylene-n,n'-bis((alkoxy benzoyloxy)alkyl)alkylene diimines |
| ES0334393A ES334393A1 (es) | 1965-12-16 | 1966-12-10 | Procedimiento para la fabricacion de nuevos esteres basicos. |
| SE17000/66A SE317977B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-16 | 1966-12-12 | |
| BE691016D BE691016A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-16 | 1966-12-12 | |
| CS668008A CS191151B2 (en) | 1965-12-16 | 1966-12-14 | Method of producing novel basic esters |
| CH1789566A CH476742A (de) | 1965-12-16 | 1966-12-15 | Verfahren zur Herstellung von neuen basischen Estern |
| NL666617653A NL153537B (nl) | 1965-12-16 | 1966-12-15 | Werkwijze voor het bereiden van benzoyloxyalkylaminoverbindingen met coronair-verwijdende activiteit. |
| FR87720A FR6053M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-12-16 | 1966-12-16 | |
| MY197127A MY7100027A (en) | 1965-12-16 | 1971-12-31 | Basic esters and a process for their production |
| CS755840A CS191167B2 (en) | 1965-12-16 | 1975-08-27 | Method of producing novel basic esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965A0051095 DE1545575C2 (de) | 1965-12-16 | 1965-12-16 | N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1545575B1 DE1545575B1 (de) | 1970-02-05 |
| DE1545575C2 true DE1545575C2 (de) | 1970-09-10 |
Family
ID=6937763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965A0051095 Expired DE1545575C2 (de) | 1965-12-16 | 1965-12-16 | N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazin |
Country Status (14)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980643A (en) * | 1974-01-04 | 1976-09-14 | Hokuriku Pharmaceutical Co., Ltd. | Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof |
| US4035494A (en) * | 1975-10-20 | 1977-07-12 | Sandoz, Inc. | Bis-p-pivaloyl benzylamines |
| DE3403778A1 (de) * | 1984-02-03 | 1985-08-08 | Degussa Ag, 6000 Frankfurt | Cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amin seine verwendung zur herstellung von 1-(3-hydroxy-propyl)-1,4-diazepan und 1,4-bis(3-(3,4,5-trimethoxybenzoyloxy)-propyl)-diazepan |
| JPS60258118A (ja) * | 1984-06-06 | 1985-12-20 | Kowa Co | 抗動脈硬化剤 |
| DE3438289A1 (de) * | 1984-10-19 | 1986-04-24 | Degussa Ag, 6000 Frankfurt | Verfahren zum reinigen von dilazep-base |
| PL375713A1 (en) | 2002-08-19 | 2005-12-12 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
| US20060063803A1 (en) * | 2004-09-23 | 2006-03-23 | Pfizer Inc | 4-Amino substituted-2-substituted-1,2,3,4-tetrahydroquinoline compounds |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| EP2094643B1 (en) | 2006-12-01 | 2012-02-29 | Bristol-Myers Squibb Company | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| HUE069590T2 (hu) | 2019-01-18 | 2025-03-28 | Astrazeneca Ab | PCSK9-gátló 6'-[[(1s,3s)-3-[[5-(difluormetoxi)-2-pirimidinil]amino]ciklopentil]amino][1(2h ),3'-bipiridin]-2-on és alkalmazására szolgáló eljárások |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE629910A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-03-22 | |||
| DE1182239B (de) * | 1962-04-02 | 1964-11-26 | Lentia Gmbh | Verfahren zur Herstellung von Piperazinderivaten |
-
1965
- 1965-12-16 DE DE1965A0051095 patent/DE1545575C2/de not_active Expired
-
1966
- 1966-12-01 DK DK620966AA patent/DK113291B/da unknown
- 1966-12-02 GB GB54090/66A patent/GB1107470A/en not_active Expired
- 1966-12-05 IL IL27013A patent/IL27013A/xx unknown
- 1966-12-05 AT AT1120566A patent/AT275527B/de active
- 1966-12-07 US US599724A patent/US3532685A/en not_active Expired - Lifetime
- 1966-12-10 ES ES0334393A patent/ES334393A1/es not_active Expired
- 1966-12-12 BE BE691016D patent/BE691016A/xx not_active IP Right Cessation
- 1966-12-12 SE SE17000/66A patent/SE317977B/xx unknown
- 1966-12-14 CS CS668008A patent/CS191151B2/cs unknown
- 1966-12-15 NL NL666617653A patent/NL153537B/xx not_active IP Right Cessation
- 1966-12-15 CH CH1789566A patent/CH476742A/de not_active IP Right Cessation
- 1966-12-16 FR FR87720A patent/FR6053M/fr not_active Expired
-
1971
- 1971-12-31 MY MY197127A patent/MY7100027A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE691016A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-12 |
| DE1545575B1 (de) | 1970-02-05 |
| US3532685A (en) | 1970-10-06 |
| AT275527B (de) | 1969-10-27 |
| DK113291B (da) | 1969-03-10 |
| NL6617653A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-19 |
| FR6053M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-05-20 |
| CS191151B2 (en) | 1979-06-29 |
| NL153537B (nl) | 1977-06-15 |
| CH476742A (de) | 1969-08-15 |
| IL27013A (en) | 1970-07-19 |
| SE317977B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-12-01 |
| ES334393A1 (es) | 1967-11-01 |
| MY7100027A (en) | 1971-12-31 |
| GB1107470A (en) | 1968-03-27 |
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| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |