DE2542329C2 - 2,3-Dihydro-1-benzothiepin-4-carbonsäureamide, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, die diese Verbindungen enthalten - Google Patents
2,3-Dihydro-1-benzothiepin-4-carbonsäureamide, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, die diese Verbindungen enthaltenInfo
- Publication number
- DE2542329C2 DE2542329C2 DE2542329A DE2542329A DE2542329C2 DE 2542329 C2 DE2542329 C2 DE 2542329C2 DE 2542329 A DE2542329 A DE 2542329A DE 2542329 A DE2542329 A DE 2542329A DE 2542329 C2 DE2542329 C2 DE 2542329C2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- general formula
- benzothiepin
- chloro
- hydroxy
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 20
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- OCIPBCQLICPGLC-UHFFFAOYSA-N 2,3-dihydro-1-benzothiepine-4-carboxamide Chemical class S1CCC(C(=O)N)=CC2=CC=CC=C21 OCIPBCQLICPGLC-UHFFFAOYSA-N 0.000 title claims 2
- 239000000460 chlorine Substances 0.000 claims description 35
- -1 methylthiophenyl Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 11
- 150000002085 enols Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000002081 enamines Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
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- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004799 bromophenyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- RIPYGTPGAMWYIX-UHFFFAOYSA-N methoxymethyl thiohypofluorite Chemical compound COCSF RIPYGTPGAMWYIX-UHFFFAOYSA-N 0.000 claims description 2
- IUKHPYXSMWHAJG-UHFFFAOYSA-N 2,3-dihydro-1-benzothiepine Chemical class S1CCC=CC2=CC=CC=C21 IUKHPYXSMWHAJG-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- 239000000203 mixture Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 17
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 239000000047 product Substances 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
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- 150000001408 amides Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
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- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 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
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000011200 topical administration Methods 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50952474A | 1974-09-26 | 1974-09-26 | |
| US58514775A | 1975-06-09 | 1975-06-09 | |
| US74320876A | 1976-11-18 | 1976-11-18 | |
| US05/854,176 US4185109A (en) | 1974-09-26 | 1977-11-23 | 1-Benzothiepin-4-carboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2542329A1 DE2542329A1 (de) | 1976-04-15 |
| DE2542329C2 true DE2542329C2 (de) | 1984-05-24 |
Family
ID=27504481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2542329A Expired DE2542329C2 (de) | 1974-09-26 | 1975-09-23 | 2,3-Dihydro-1-benzothiepin-4-carbonsäureamide, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, die diese Verbindungen enthalten |
Country Status (10)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4242266A (en) * | 1974-09-26 | 1980-12-30 | Ciba-Geigy Corporation | 1-Benzothiepin-4-carboxylic acid derivatives |
| US4277484A (en) * | 1978-09-20 | 1981-07-07 | Ciba-Geigy Corporation | 1-Benzothiepin-4-carboxamides |
| US4582850A (en) * | 1985-02-28 | 1986-04-15 | Ciba-Geigy Corporation | Topical and systemic treatment of psoriasis using 7-chloro-N-(3,4-dichlorophenyl)-2,3-dihydro-5-hydroxy-1-benzothiepin-4-carboxamide 1,1-dioxide and pharmaceutically acceptable salts thereof |
| US4803197A (en) * | 1987-01-12 | 1989-02-07 | Ciba-Geigy Corporation | 2,1-benzothiazepine-2,2-dioxide-5-carboxylic acid derivatives |
| US6268392B1 (en) | 1994-09-13 | 2001-07-31 | G. D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors |
| US6262277B1 (en) | 1994-09-13 | 2001-07-17 | G.D. Searle And Company | Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US6642268B2 (en) | 1994-09-13 | 2003-11-04 | G.D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors |
| US6221897B1 (en) * | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
| IL143946A0 (en) * | 1998-12-23 | 2002-04-21 | Searle Llc | Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein for cardiovascular indications |
| US6462091B1 (en) | 1998-12-23 | 2002-10-08 | G.D. Searle & Co. | Combinations of cholesteryl ester transfer protein inhibitors and HMG coA reductase inhibitors for cardiovascular indications |
| EP1140184B1 (en) * | 1998-12-23 | 2003-06-04 | G.D. Searle LLC. | Combinations of cholesteryl ester transfer protein inhibitors and nicotinic acid derivatives for cardiovascular indications |
| CN1338945A (zh) * | 1998-12-23 | 2002-03-06 | G·D·瑟尔有限公司 | 适用于心血管疾病的回肠胆汁酸转运抑制剂和胆汁酸螯合剂组合 |
| AU2157500A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle Llc | Combinations of cholesteryl ester transfer protein inhibitors and bile acid sequestering agents for cardiovascular indications |
| CA2356607A1 (en) | 1998-12-23 | 2000-07-06 | G.D. Searle Llc | Combinations of ileal bile acid transport inhibitors and fibric acid derivatives for cardiovascular indications |
| AU779264B2 (en) * | 1998-12-23 | 2005-01-13 | G.D. Searle Llc | Combinations for cardiovascular indications |
| JP2002533410A (ja) * | 1998-12-23 | 2002-10-08 | ジー．ディー．サール エルエルシー | 心臓血管に適用するためのコレステリルエステル転送タンパク質阻害剤およびフィブリン酸誘導体の組み合わせ |
| US20020061888A1 (en) * | 2000-03-10 | 2002-05-23 | Keller Bradley T. | Combination therapy for the prophylaxis and treatment of hyperlipidemic conditions and disorders |
| WO2001068637A2 (en) | 2000-03-10 | 2001-09-20 | Pharmacia Corporation | Method for the preparation of tetrahydrobenzothiepines |
| US20040077625A1 (en) * | 2001-07-25 | 2004-04-22 | Tremont Samuel J. | Novel 1,4-benzothiazepine and 1,5-benzothiazepine compounds as inhibitors of apical sodium codependent bile acid transport abd taurocholate uptake |
| BR0213501A (pt) * | 2001-11-02 | 2004-08-24 | Searle Llc | Compostos de benzotiepina mono- e di-fluorada como inibidores de transporte de ácido biliar co-dependente de sódio apical (asbt) e captação de taurocolato |
| US6852753B2 (en) | 2002-01-17 | 2005-02-08 | Pharmacia Corporation | Alkyl/aryl hydroxy or keto thiepine compounds as inhibitors of apical sodium co-dependent bile acid transport (ASBT) and taurocholate uptake |
| WO2013063512A1 (en) | 2011-10-28 | 2013-05-02 | Lumena Pharmaceuticals, Inc | Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases |
| BR112014010228B1 (pt) | 2011-10-28 | 2020-09-29 | Lumena Pharmaceuticals Llc | Uso de inibidores de reciclagem de ácido biliar para o tratamento de hipercolemia e doença hepática colestática |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287368A (en) * | 1965-06-08 | 1966-11-22 | Mcneilab Inc | Dihydrobenzothiepin-5(2h)-one oximes |
| US3287370A (en) * | 1965-06-08 | 1966-11-22 | Mcneilab Inc | Tetrahydrobenzothiepins |
| US3389144A (en) * | 1965-06-08 | 1968-06-18 | Mcneilab Inc | 5-pyridyl-2, 3, 4, 5-tetrahydrobenzothiepin-5-ols |
| US3444176A (en) * | 1967-04-28 | 1969-05-13 | Mcneilab Inc | Certain 4-diloweralkylamino-lower alkyl - 5 - pyridyl (or phenyl)-2,3-dihydro - 1 - benzothiepins and derivatives thereof |
| US3505355A (en) * | 1968-08-12 | 1970-04-07 | Mcneilab Inc | Certain dihydrobenzo-thiepin-5(2h)-ones |
| DE2264938A1 (de) * | 1971-07-15 | 1975-06-12 | Warner Lambert Co | 3-arylaminocarbonyl-4-hydroxy-benzo eckige klammer auf b eckige klammer zu thiacyclohex(3)en-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US3828055A (en) * | 1972-04-28 | 1974-08-06 | Warner Lambert Co | Heterocyclic amides of 4-hydroxy-2h-1-benzothiopyran-3-carboxylic acid 1,1-dioxide |
| US3826791A (en) * | 1972-04-28 | 1974-07-30 | Warner Lambert Co | Heterocyclic amides of 4-hydroxy-2h-1-benzothiopyran-3-carboxylic acid 1,1-dioxide and process for their production |
| US3769292A (en) * | 1972-04-28 | 1973-10-30 | Warner Lambert Co | N-(pyridyl)2h 1-benzothiopyran-3-carboxamide-4-hydroxy 1,1-dioxides |
| US3962261A (en) * | 1974-02-04 | 1976-06-08 | Warner-Lambert Company | 2,3,4,5-tetra hydro-5-oxo-1-benzothiepi n-4-carboxamide 1,1-dioxides |
-
1975
- 1975-09-12 SE SE7510196A patent/SE420725B/xx not_active IP Right Cessation
- 1975-09-23 DE DE2542329A patent/DE2542329C2/de not_active Expired
- 1975-09-24 AU AU85148/75A patent/AU496764B2/en not_active Expired
- 1975-09-24 CH CH1240875A patent/CH617433A5/de not_active IP Right Cessation
- 1975-09-24 FR FR7529231A patent/FR2285872A1/fr active Granted
- 1975-09-24 CA CA236,220A patent/CA1066279A/en not_active Expired
- 1975-09-25 NL NL7511316A patent/NL7511316A/xx not_active Application Discontinuation
- 1975-09-25 BE BE160345A patent/BE833787A/xx not_active IP Right Cessation
- 1975-09-25 AT AT734175A patent/AT346338B/de not_active IP Right Cessation
-
1977
- 1977-11-23 US US05/854,176 patent/US4185109A/en not_active Expired - Lifetime
-
1979
- 1979-10-11 CH CH919079A patent/CH623580A5/de not_active IP Right Cessation
- 1979-10-11 CH CH919179A patent/CH623581A5/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CH623580A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-15 |
| SE420725B (sv) | 1981-10-26 |
| FR2285872A1 (fr) | 1976-04-23 |
| BE833787A (fr) | 1976-03-25 |
| CH623581A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-15 |
| AU496764B2 (en) | 1978-10-26 |
| DE2542329A1 (de) | 1976-04-15 |
| US4185109A (en) | 1980-01-22 |
| ATA734175A (de) | 1978-03-15 |
| CA1066279A (en) | 1979-11-13 |
| CH617433A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-30 |
| FR2285872B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-10 |
| SE7510196L (sv) | 1976-03-29 |
| AU8514875A (en) | 1977-03-31 |
| NL7511316A (nl) | 1976-03-30 |
| AT346338B (de) | 1978-11-10 |
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| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |