CA1080219A - Piperazine derivatives and a process for the preparation thereof - Google Patents
Piperazine derivatives and a process for the preparation thereofInfo
- Publication number
- CA1080219A CA1080219A CA293,096A CA293096A CA1080219A CA 1080219 A CA1080219 A CA 1080219A CA 293096 A CA293096 A CA 293096A CA 1080219 A CA1080219 A CA 1080219A
- Authority
- CA
- Canada
- Prior art keywords
- propane
- piperazin
- xanthene
- carbonyloxy
- process according
- 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
- 238000000034 method Methods 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000004885 piperazines Chemical class 0.000 title claims description 5
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 32
- -1 phenoxy, methoxy-cyclohexyl Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 27
- 239000001294 propane Substances 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 11
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- RWHQTSQQOYHQGH-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate Chemical compound C1CN(CCCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 RWHQTSQQOYHQGH-UHFFFAOYSA-N 0.000 claims description 8
- VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 claims description 7
- 239000012190 activator Substances 0.000 claims description 5
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 4
- YZBJUGHSSZLKRM-UHFFFAOYSA-N ethyl 4-[3-(9h-xanthene-9-carbonyloxy)propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 YZBJUGHSSZLKRM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 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 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- NBJFLRHSKDDJMS-UHFFFAOYSA-N 3-[4-(2-phenoxyethyl)piperazin-1-yl]propyl 9h-xanthene-9-carboxylate Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1CCOC1=CC=CC=C1 NBJFLRHSKDDJMS-UHFFFAOYSA-N 0.000 claims 4
- PBESDFLETINPKX-UHFFFAOYSA-N 3-(4-benzylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1CC1=CC=CC=C1 PBESDFLETINPKX-UHFFFAOYSA-N 0.000 claims 3
- UZJJWUSWTWWZEX-UHFFFAOYSA-N 3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl furan-2-carboxylate Chemical compound COC1=CC=CC(N2CCN(CCCOC(=O)C=3OC=CC=3)CC2)=C1 UZJJWUSWTWWZEX-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- BKRJTLPVSARANE-UHFFFAOYSA-N 3-(4-benzylpiperazin-1-yl)propan-1-ol Chemical compound C1CN(CCCO)CCN1CC1=CC=CC=C1 BKRJTLPVSARANE-UHFFFAOYSA-N 0.000 claims 1
- PRBASKPGFZYSAI-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propan-1-ol Chemical compound CCCCN1CCN(CCCO)CC1 PRBASKPGFZYSAI-UHFFFAOYSA-N 0.000 claims 1
- LLTVLFHJCBDYPG-UHFFFAOYSA-N 3-(4-prop-2-enylpiperazin-1-yl)propan-1-ol Chemical compound OCCCN1CCN(CC=C)CC1 LLTVLFHJCBDYPG-UHFFFAOYSA-N 0.000 claims 1
- JNANLGAZMJOZBL-UHFFFAOYSA-N ethyl 4-(3-hydroxypropyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CCCO)CC1 JNANLGAZMJOZBL-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 5
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JYRSCMLJPXJTLI-UHFFFAOYSA-N 9h-xanthene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)C3=CC=CC=C3OC2=C1 JYRSCMLJPXJTLI-UHFFFAOYSA-N 0.000 description 2
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
- 238000001990 intravenous administration Methods 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
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
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- JREHPVSBEVQWQE-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 JREHPVSBEVQWQE-UHFFFAOYSA-N 0.000 description 1
- LVNLMFITHNZGKA-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propan-1-ol Chemical compound C1CN(CCCO)CCN1C1=CC=CC=C1 LVNLMFITHNZGKA-UHFFFAOYSA-N 0.000 description 1
- UGMNBYGTGBNHDC-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1 UGMNBYGTGBNHDC-UHFFFAOYSA-N 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76RI605A HU174215B (hu) | 1976-12-15 | 1976-12-15 | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080219A true CA1080219A (en) | 1980-06-24 |
Family
ID=11001009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,096A Expired CA1080219A (en) | 1976-12-15 | 1977-12-14 | Piperazine derivatives and a process for the preparation thereof |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4140790A (enExample) |
| JP (2) | JPS6026114B2 (enExample) |
| AT (1) | AT359507B (enExample) |
| BE (1) | BE861849A (enExample) |
| CA (1) | CA1080219A (enExample) |
| CH (1) | CH632750A5 (enExample) |
| DE (1) | DE2755707A1 (enExample) |
| ES (1) | ES465061A1 (enExample) |
| FI (1) | FI65427C (enExample) |
| FR (1) | FR2374322A1 (enExample) |
| GB (1) | GB1580227A (enExample) |
| HU (1) | HU174215B (enExample) |
| IL (1) | IL53552A (enExample) |
| IN (1) | IN146474B (enExample) |
| NL (1) | NL7713827A (enExample) |
| NO (1) | NO147306C (enExample) |
| PT (1) | PT67403B (enExample) |
| SE (1) | SE430159B (enExample) |
| SU (1) | SU694071A3 (enExample) |
| YU (1) | YU293677A (enExample) |
| ZA (1) | ZA777398B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
| US4703120A (en) * | 1986-04-28 | 1987-10-27 | Ortho Pharmaceutical Corporation | Furo(3,4-d)pyrimidine-2,4-dione derivatives and intermediates thereof |
| CN1060168C (zh) * | 1994-05-06 | 2001-01-03 | 中国人民解放军军事医学科学院毒物药物研究所 | 新的呫吨衍生物，其制备方法及含它们的药物组合物 |
| MXPA04007459A (es) | 2002-02-01 | 2005-09-08 | Astrazeneca Ab | Compuestos de quinazolina. |
| JP2006522742A (ja) * | 2003-04-08 | 2006-10-05 | ニューロームド テクノロジーズ、インク． | ピペラジンから距離をおいて配置したベンズヒドリル基から成る一群のカルシウムチャンネル阻害剤 |
| US20080207738A1 (en) * | 2007-02-28 | 2008-08-28 | Cancure Laboratories, Llc | Drug combinations to treat drug resistant tumors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3481930A (en) * | 1966-11-21 | 1969-12-02 | American Home Prod | Xanthene and thioxanthene-9 ureas and propionamides |
| US3502662A (en) * | 1968-03-18 | 1970-03-24 | American Home Prod | N-(9-xanthenyl or thioxanthenyl)-3-amino or iodo-propionamides and 4-(9-xanthenyl or thioxanthenyl)-thiosemicarbazones |
| FR2201084B1 (enExample) * | 1972-09-29 | 1975-10-31 | Bouchara Emile | |
| US3953449A (en) * | 1973-05-09 | 1976-04-27 | Synthelabo | 2-(4-M-CF3 or -SCF3 phenylpiperazino)-ethyl benzoates |
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
-
1976
- 1976-12-15 HU HU76RI605A patent/HU174215B/hu unknown
-
1977
- 1977-11-25 JP JP52140843A patent/JPS6026114B2/ja not_active Expired
- 1977-12-02 CH CH1475877A patent/CH632750A5/de not_active IP Right Cessation
- 1977-12-05 AT AT867677A patent/AT359507B/de not_active IP Right Cessation
- 1977-12-06 IL IL53552A patent/IL53552A/xx unknown
- 1977-12-07 SE SE7713906A patent/SE430159B/xx unknown
- 1977-12-09 FR FR7737196A patent/FR2374322A1/fr active Granted
- 1977-12-12 US US05/859,928 patent/US4140790A/en not_active Expired - Lifetime
- 1977-12-12 IN IN1717/CAL/77A patent/IN146474B/en unknown
- 1977-12-12 ZA ZA00777398A patent/ZA777398B/xx unknown
- 1977-12-12 YU YU02936/77A patent/YU293677A/xx unknown
- 1977-12-12 FI FI773743A patent/FI65427C/fi not_active IP Right Cessation
- 1977-12-13 SU SU772555706A patent/SU694071A3/ru active
- 1977-12-14 GB GB52038/77A patent/GB1580227A/en not_active Expired
- 1977-12-14 NL NL7713827A patent/NL7713827A/xx not_active Application Discontinuation
- 1977-12-14 JP JP14945477A patent/JPS5377073A/ja active Pending
- 1977-12-14 DE DE19772755707 patent/DE2755707A1/de not_active Ceased
- 1977-12-14 BE BE183452A patent/BE861849A/xx not_active IP Right Cessation
- 1977-12-14 NO NO774294A patent/NO147306C/no unknown
- 1977-12-14 PT PT67403A patent/PT67403B/pt unknown
- 1977-12-14 CA CA293,096A patent/CA1080219A/en not_active Expired
- 1977-12-14 ES ES465061A patent/ES465061A1/es not_active Expired
-
1978
- 1978-12-28 US US05/974,082 patent/US4250310A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO774294L (no) | 1978-06-16 |
| FI65427C (fi) | 1984-05-10 |
| ZA777398B (en) | 1978-10-25 |
| ES465061A1 (es) | 1979-01-01 |
| IL53552A0 (en) | 1978-03-10 |
| CH632750A5 (de) | 1982-10-29 |
| NO147306C (no) | 1983-03-16 |
| SE430159B (sv) | 1983-10-24 |
| AT359507B (de) | 1980-11-10 |
| YU293677A (en) | 1982-08-31 |
| PT67403B (en) | 1979-05-21 |
| IN146474B (enExample) | 1979-06-16 |
| GB1580227A (en) | 1980-11-26 |
| FR2374322A1 (fr) | 1978-07-13 |
| FI773743A7 (fi) | 1978-06-16 |
| JPS5377073A (en) | 1978-07-08 |
| ATA867677A (de) | 1980-04-15 |
| US4250310A (en) | 1981-02-10 |
| SE7713906L (sv) | 1978-06-16 |
| NL7713827A (nl) | 1978-06-19 |
| BE861849A (fr) | 1978-03-31 |
| PT67403A (en) | 1978-01-01 |
| IL53552A (en) | 1981-07-31 |
| FI65427B (fi) | 1984-01-31 |
| DE2755707A1 (de) | 1978-06-29 |
| JPS5377080A (en) | 1978-07-08 |
| NO147306B (no) | 1982-12-06 |
| JPS6026114B2 (ja) | 1985-06-21 |
| SU694071A3 (ru) | 1979-10-25 |
| US4140790A (en) | 1979-02-20 |
| FR2374322B1 (enExample) | 1981-11-27 |
| HU174215B (hu) | 1979-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |