SU662009A3 - Способ получени производных пиперидина или их солей - Google Patents
Способ получени производных пиперидина или их солейInfo
- Publication number
- SU662009A3 SU662009A3 SU772534003A SU2534003A SU662009A3 SU 662009 A3 SU662009 A3 SU 662009A3 SU 772534003 A SU772534003 A SU 772534003A SU 2534003 A SU2534003 A SU 2534003A SU 662009 A3 SU662009 A3 SU 662009A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- piperidine
- salts
- piperidine derivatives
- mol
- obtaining
- Prior art date
Links
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
- 238000002474 experimental method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- -1 2-Chlorphenoxymethyl Chemical group 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000000243 solution Substances 0.000 description 3
- XLHLVPVJPDGPBC-UHFFFAOYSA-N 4-(chloromethyl)piperidine;hydrochloride Chemical compound Cl.ClCC1CCNCC1 XLHLVPVJPDGPBC-UHFFFAOYSA-N 0.000 description 2
- SVJZXTDZALYYRB-UHFFFAOYSA-N 4-[(2-nitrophenoxy)methyl]piperidine Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1CCNCC1 SVJZXTDZALYYRB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- BREBKAKBNYXIOP-UHFFFAOYSA-N 4-(phenoxymethyl)piperidine Chemical compound C1CNCCC1COC1=CC=CC=C1 BREBKAKBNYXIOP-UHFFFAOYSA-N 0.000 description 1
- FGIVWTSVLVUKOK-UHFFFAOYSA-N 4-[(2-bromophenoxy)methyl]piperidine Chemical compound BrC1=CC=CC=C1OCC1CCNCC1 FGIVWTSVLVUKOK-UHFFFAOYSA-N 0.000 description 1
- SIWFDPQWVCNYFU-UHFFFAOYSA-N 4-[(2-ethylphenoxy)methyl]piperidine Chemical compound CCC1=CC=CC=C1OCC1CCNCC1 SIWFDPQWVCNYFU-UHFFFAOYSA-N 0.000 description 1
- GTYCVCKSMFWBQA-UHFFFAOYSA-N 4-[(2-fluorophenoxy)methyl]piperidine Chemical compound FC1=CC=CC=C1OCC1CCNCC1 GTYCVCKSMFWBQA-UHFFFAOYSA-N 0.000 description 1
- PVLZQVJPOZTGMJ-UHFFFAOYSA-N 4-[(2-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC=C1OCC1CCNCC1 PVLZQVJPOZTGMJ-UHFFFAOYSA-N 0.000 description 1
- PPHIYDGKKZEIPW-UHFFFAOYSA-N 4-[(2-propylphenoxy)methyl]piperidine Chemical compound CCCC1=CC=CC=C1OCC1CCNCC1 PPHIYDGKKZEIPW-UHFFFAOYSA-N 0.000 description 1
- BJWGYFBJEZCOEG-UHFFFAOYSA-N 4-[(3-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC(OCC2CCNCC2)=C1 BJWGYFBJEZCOEG-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001425800 Pipa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Взаимодействие соединений общей формулы ( it ) с соединени ми общей формулы {щ ) целесообразно проводить в щелочной среде, например в низшем спирте, в присутствии гидроокиси или алкогол та щелочного металла при температуре от до температуры кипени растворител . П р,и .м е р 1. 4-Фенрксиметилпнперидин . К смеси, состо щей из 28 мл 30%ного-раствора метилата натри , и 50 мл метанола, добавл ют 14,1 г (0,15 моль) фенола, затем упаривают в вакууме, смешивают с 50 мл N,N-диметилформамида и 7,8 г (0,05 моль гидрохлорида 4-хлорметилпиперидина и нагревают 18 ч при 70-80 С. После охлаждени разбавл ют эфиром, промывают водой и )азбавленным раствором (гидроокиси натри , высушивают йадсульфатом натри и упаривают- в вакууме . Получйют 3,1 г 4-феноксиметилпипёридина . Выход 32%, т.пл. 41-42 0 Испольэуе.мый в качестве исходного соединени гидрохлорид 4-клОрМетилпиперидина получают следующим образо , к раствору 58 мл тионилхлорида в 250 мл хлороформа прибавл ют по капл м раствор 45 г (0,39 моль) 4-оксиметилпйперидина в 200 мл хлороформа . Смесь перемешивают в течение 1 чпри кип чении с обратным холодильником , упаривают в вакууме и растирают остаток с эфиром. Получают 54,2 г гидрохлорида 4-хло метилпиперидина . Выход 88%, т,пл. f30-132 C. Пример 2. 4-(2-Нитрофеноксиметил )-пиперидин. Смесь, состо щую из 23,0 г (0,2 моль) 4-оксиметилпиперидина, 31,5 г (0,2 моль) 2-хлорнитробензола, 11,8 г (0,21 моль) гидроокиси ксши и 200 мл диоксана, нагревают 3 дн при 70°С, затем упаривают в вакууме, раствор ют остаток в эфире, прогвлвают водой, экстрагируют разбавленной сол ной кислотой, подщелачивают экстракт и экстрагируют водную смесь эфиром. После упаривани растворител получают 10,5 г 4-(2-нитрофеноксиметил )-пиперидина. Выход 22%, т.кип. 130-132 С/0,01 мм рт.ст. Аналогично примеру 1 получают целевые продукты, приёеденные в таблице.v
4-(2-Бромфеноксиметил)-пиперидин . , ::
4-(2-Хлорфеноксиметил)-пиперидии , ,
4-(3-Хлорфеноксиметил)-пипе
ридин
4-(2-Фторфеноксиметил)-пиперидин
.4-(4-Фторфеноксиметил)-пиперидин
4-(2-Метбксифеноксиметил)-пипридин .
4-(3-Метоксифеноксиметил)-пиперидин .
4-(4-Метоксифеноксиметил)-пип ридин
4-(2-Бутоксифеноксиметил)-пипридин
4-(2-Метилфеноксиметил)-пиперидин
4 (4-Метилфеноксиметил) -пиперидин
48-50
35-37
4-(4-Метилфе оксиметил)-пиперидин
4-(2-н-Пропилфеноксиметил)-пиперидин
4-(2-Этилфеноксиметил)-пиперидин
(2-Бутил)-феноксиметил -пиперидин
Claims (1)
1. Вейганд-Хильгетаг Методы эксперимента в орзганической химии . М., Хими , 1968, с. 333-340.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752549999 DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU662009A3 true SU662009A3 (ru) | 1979-05-05 |
Family
ID=5961166
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762415648A SU633473A3 (ru) | 1975-11-07 | 1976-11-02 | Способ получени производных пиперидина или их солей |
| SU772534003A SU662009A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
| SU772534004A SU867298A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762415648A SU633473A3 (ru) | 1975-11-07 | 1976-11-02 | Способ получени производных пиперидина или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772534004A SU867298A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4243807A (ru) |
| JP (1) | JPS6055509B2 (ru) |
| AT (1) | AT352726B (ru) |
| BE (1) | BE847973A (ru) |
| CA (1) | CA1077942A (ru) |
| CH (3) | CH624102A5 (ru) |
| DD (1) | DD126942A5 (ru) |
| DE (1) | DE2549999A1 (ru) |
| DK (1) | DK494876A (ru) |
| FI (1) | FI763148A7 (ru) |
| FR (1) | FR2330678A1 (ru) |
| GB (1) | GB1502050A (ru) |
| HU (1) | HU171237B (ru) |
| IE (1) | IE43866B1 (ru) |
| IT (1) | IT1063618B (ru) |
| LU (1) | LU76141A1 (ru) |
| NL (1) | NL7612286A (ru) |
| SE (1) | SE7612234L (ru) |
| SU (3) | SU633473A3 (ru) |
| ZA (1) | ZA766381B (ru) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| US4556664A (en) * | 1984-03-13 | 1985-12-03 | Gunnar A. K. Aberg | Method and composition for the treatment of cardiac arrhythmias |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| US5231184A (en) * | 1987-11-23 | 1993-07-27 | Janssen Pharmaceutica N.V. | Pridazinamine derivatives |
| US4822778A (en) * | 1988-01-19 | 1989-04-18 | Gunnar Aberg | Membrane stabilizing phenoxy-piperidine compounds and pharmaceutical compositions employing such compounds |
| US5109002A (en) * | 1989-09-08 | 1992-04-28 | Du Pont Merck Pharmaceutical Company | Antipsychotic 1-cycloalkylpiperidines |
| IL99537A (en) * | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical compositions containing them |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| US5264420A (en) * | 1990-09-27 | 1993-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| FR2667317B1 (fr) * | 1990-10-02 | 1992-12-04 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| US5321034A (en) * | 1991-05-07 | 1994-06-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| FI934894L (fi) * | 1991-05-07 | 1993-11-05 | Merck & Co Inc | Fibrinogenreceptorantagonister |
| US5416099A (en) * | 1991-10-29 | 1995-05-16 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5389631A (en) * | 1991-10-29 | 1995-02-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5272158A (en) * | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5358956A (en) * | 1992-10-14 | 1994-10-25 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| AU675680B2 (en) * | 1992-10-14 | 1997-02-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| CA2150550A1 (en) * | 1992-12-01 | 1994-06-09 | Melissa S. Egbertson | Fibrinogen receptor antagonists |
| US5441952A (en) * | 1993-04-05 | 1995-08-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5397791A (en) * | 1993-08-09 | 1995-03-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5821241A (en) * | 1994-02-22 | 1998-10-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5719144A (en) * | 1995-02-22 | 1998-02-17 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5750147A (en) | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| AU7096496A (en) * | 1995-09-28 | 1997-04-17 | Kaken Pharmaceutical Co., Ltd. | Process for the preparation of 4-methylenepiperidines |
| US5789421A (en) * | 1995-10-26 | 1998-08-04 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5780480A (en) * | 1996-02-28 | 1998-07-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5889023A (en) * | 1996-05-10 | 1999-03-30 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5981584A (en) * | 1997-02-06 | 1999-11-09 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| ES2434250T3 (es) | 2008-07-24 | 2013-12-16 | Theravance, Inc. | Compuestos de 3-(fenoxifenilmetil)pirrolidina |
| SI2358676T1 (sl) * | 2008-11-14 | 2013-01-31 | Theravance, Inc. | Kristalinična oblika 4-(2-(2-fluorofenoksimetil)fenil)piperidinske spojine |
| EP2419405A1 (en) * | 2009-04-15 | 2012-02-22 | Theravance, Inc. | 3-(phenoxypyrrolidin-3-yl-methyl)heteroaryl, 3-(phenylpyrrolidin-3-ylmethoxy)heteroaryl, and 3-(heteroarylpyrrolidin-3-ylmethoxy)heteroaryl compounds |
| AU2010273645B2 (en) | 2009-07-13 | 2014-12-04 | Theravance Biopharma R&D Ip, Llc | 3-phenoxymethylpyrrolidine compounds |
| US8273786B2 (en) * | 2009-07-21 | 2012-09-25 | Theravance, Inc. | 3-phenoxymethylpyrrolidine compounds |
| EP2523945A1 (en) | 2010-01-11 | 2012-11-21 | Theravance, Inc. | 1 - (2 - phenoxymethylphenyl) piperazine compounds as serotonin and norepinephrine reuptake inhibitors |
| EP2550252B1 (en) * | 2010-03-22 | 2015-05-06 | Theravance Biopharma R&D IP, LLC | 1-(2-phenoxymethylheteroaryl)piperidine and piperazine compounds |
| WO2012051103A1 (en) | 2010-10-11 | 2012-04-19 | Theravance, Inc. | Serotonin reuptake inhibitors |
| US8501964B2 (en) | 2010-12-03 | 2013-08-06 | Theravance, Inc. | Serotonin reuptake inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268951A (en) * | 1969-06-12 | 1972-03-29 | Pfizer Ltd | Phenoxy-amines |
| DE2245061A1 (de) * | 1972-09-14 | 1974-03-28 | Boehringer Mannheim Gmbh | Derivate des adenins |
| DE2401254A1 (de) * | 1974-01-11 | 1975-11-27 | Boehringer Mannheim Gmbh | Neue derivate von n hoch 6-substituierten adeninen |
| DE2550000A1 (de) * | 1975-11-07 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue purin-derivate und verfahren zu ihrer herstellung |
-
1975
- 1975-11-07 DE DE19752549999 patent/DE2549999A1/de active Granted
-
1976
- 1976-10-25 ZA ZA766381A patent/ZA766381B/xx unknown
- 1976-10-28 CA CA264,608A patent/CA1077942A/en not_active Expired
- 1976-10-29 IE IE2394/76A patent/IE43866B1/en unknown
- 1976-11-01 US US05/737,518 patent/US4243807A/en not_active Expired - Lifetime
- 1976-11-01 HU HU76BO00001639A patent/HU171237B/hu not_active IP Right Cessation
- 1976-11-02 SU SU762415648A patent/SU633473A3/ru active
- 1976-11-02 DK DK494876A patent/DK494876A/da not_active Application Discontinuation
- 1976-11-03 CH CH1385576A patent/CH624102A5/de not_active IP Right Cessation
- 1976-11-03 SE SE7612234A patent/SE7612234L/xx not_active Application Discontinuation
- 1976-11-03 FI FI763148A patent/FI763148A7/fi not_active Application Discontinuation
- 1976-11-04 GB GB45916/76A patent/GB1502050A/en not_active Expired
- 1976-11-04 BE BE172068A patent/BE847973A/xx not_active IP Right Cessation
- 1976-11-04 DD DD195610A patent/DD126942A5/xx unknown
- 1976-11-05 JP JP51133139A patent/JPS6055509B2/ja not_active Expired
- 1976-11-05 IT IT29083/76A patent/IT1063618B/it active
- 1976-11-05 NL NL7612286A patent/NL7612286A/xx not_active Application Discontinuation
- 1976-11-05 FR FR7633389A patent/FR2330678A1/fr active Granted
- 1976-11-05 LU LU76141A patent/LU76141A1/xx unknown
- 1976-11-05 AT AT823776A patent/AT352726B/de not_active IP Right Cessation
-
1977
- 1977-10-21 SU SU772534003A patent/SU662009A3/ru active
- 1977-10-21 SU SU772534004A patent/SU867298A3/ru active
-
1980
- 1980-10-03 CH CH742380A patent/CH625788A5/de not_active IP Right Cessation
- 1980-10-03 CH CH742480A patent/CH627166A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2549999A1 (de) | 1977-05-12 |
| FR2330678B1 (ru) | 1980-11-07 |
| US4243807A (en) | 1981-01-06 |
| IT1063618B (it) | 1985-02-11 |
| LU76141A1 (ru) | 1977-05-18 |
| SU633473A3 (ru) | 1978-11-15 |
| FI763148A7 (ru) | 1977-05-08 |
| BE847973A (fr) | 1977-05-04 |
| IE43866B1 (en) | 1981-06-17 |
| SE7612234L (sv) | 1977-05-07 |
| DD126942A5 (ru) | 1977-08-24 |
| CA1077942A (en) | 1980-05-20 |
| AT352726B (de) | 1979-10-10 |
| HU171237B (hu) | 1977-12-28 |
| SU867298A3 (ru) | 1981-09-23 |
| JPS5259163A (en) | 1977-05-16 |
| ZA766381B (en) | 1977-10-26 |
| GB1502050A (en) | 1978-02-22 |
| CH625788A5 (ru) | 1981-10-15 |
| NL7612286A (nl) | 1977-05-10 |
| CH627166A5 (ru) | 1981-12-31 |
| ATA823776A (de) | 1979-03-15 |
| CH624102A5 (ru) | 1981-07-15 |
| DE2549999C2 (ru) | 1989-01-26 |
| FR2330678A1 (fr) | 1977-06-03 |
| IE43866L (en) | 1977-05-07 |
| DK494876A (da) | 1977-05-08 |
| JPS6055509B2 (ja) | 1985-12-05 |
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