FR2494269A1 - Nouveaux produits de condensation entre l'acide acetylsalicylique et la piperazine, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux produits de condensation entre l'acide acetylsalicylique et la piperazine, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2494269A1 FR2494269A1 FR8106242A FR8106242A FR2494269A1 FR 2494269 A1 FR2494269 A1 FR 2494269A1 FR 8106242 A FR8106242 A FR 8106242A FR 8106242 A FR8106242 A FR 8106242A FR 2494269 A1 FR2494269 A1 FR 2494269A1
- Authority
- FR
- France
- Prior art keywords
- piperazine
- acetylsalicylic acid
- acid
- equ1
- condensation products
- 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.)
- Granted
Links
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract description 25
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title abstract description 19
- 229960001138 acetylsalicylic acid Drugs 0.000 title abstract description 17
- 239000007859 condensation product Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title description 6
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title 1
- -1 ACETYLSALICYLOYL GROUP Chemical group 0.000 abstract description 8
- 239000000047 product Substances 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 10
- 210000000988 bone and bone Anatomy 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical class CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000001387 anti-histamine Effects 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 4
- 239000002221 antipyretic Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 101150035983 str1 gene Proteins 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- OAWXYINGQXLWOE-UHFFFAOYSA-N (2-acetyloxybenzoyl) 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1OC(C)=O OAWXYINGQXLWOE-UHFFFAOYSA-N 0.000 description 1
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 1
- ZRMOLCPODIMNPJ-UHFFFAOYSA-N 1-[4-(2-hydroxypropyl)piperazin-1-yl]propan-2-ol Chemical compound CC(O)CN1CCN(CC(C)O)CC1 ZRMOLCPODIMNPJ-UHFFFAOYSA-N 0.000 description 1
- GLNAZZLXONPULP-UHFFFAOYSA-N 1-[4-[2-(2-acetyloxybenzoyl)oxypropyl]piperazin-1-yl]propan-2-yl 2-acetyloxybenzoate Chemical compound C=1C=CC=C(OC(C)=O)C=1C(=O)OC(C)CN(CC1)CCN1CC(C)OC(=O)C1=CC=CC=C1OC(C)=O GLNAZZLXONPULP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 101100311451 Chlamydomonas reinhardtii SULP1 gene Proteins 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 244000016741 Coleus dazo Species 0.000 description 1
- 235000009168 Coleus dazo Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020741 Hyperpyrexia Diseases 0.000 description 1
- 101100460719 Mus musculus Noto gene Proteins 0.000 description 1
- 101100321000 Mus musculus Ypel3 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 101100219213 Schizosaccharomyces pombe (strain 972 / ATCC 24843) ade9 gene Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 101100187345 Xenopus laevis noto gene Proteins 0.000 description 1
- 241000405115 Zela Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229940068372 acetyl salicylate Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000002788 anti-peptide Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000001562 ulcerogenic effect Effects 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26131/80A IT1194819B (it) | 1980-11-20 | 1980-11-20 | Derivati della piperazina,procedimento per la loro preparazione e relative composizioni farmaceutiche |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2494269A1 true FR2494269A1 (fr) | 1982-05-21 |
| FR2494269B1 FR2494269B1 (enExample) | 1984-03-23 |
Family
ID=11218701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8106242A Granted FR2494269A1 (fr) | 1980-11-20 | 1981-03-27 | Nouveaux produits de condensation entre l'acide acetylsalicylique et la piperazine, leur procede de preparation et leur application en therapeutique |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4420482A (enExample) |
| JP (1) | JPS57116058A (enExample) |
| AT (1) | AT374470B (enExample) |
| BE (1) | BE888139A (enExample) |
| DE (1) | DE3113087C2 (enExample) |
| FR (1) | FR2494269A1 (enExample) |
| GB (1) | GB2087869B (enExample) |
| IT (1) | IT1194819B (enExample) |
| ZA (1) | ZA817568B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11388608B2 (en) * | 2019-08-05 | 2022-07-12 | Cisco Technology, Inc. | Soft service migration between spectrum access system (SAS) providers for citizens broadband radio service (CBRS) networks |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8823776D0 (en) * | 1988-10-11 | 1988-11-16 | Scras | New 2-methoxycarbonyl sustituted n n'-di-(trimethoxybenzoyl)piperazines |
| JP3476203B2 (ja) | 1997-02-24 | 2003-12-10 | ザイモジュネティックス インコーポレイテッド | カルシトニン擬似体 |
| US6268367B1 (en) * | 1998-02-23 | 2001-07-31 | Zymogenetics, Inc. | Piperazine derivatives for treating bone deficit conditions |
| WO2023235464A1 (en) * | 2022-06-01 | 2023-12-07 | Duke University | Novel equilibrative nucleoside transporter inhibitors and methods of making and using same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2810718A (en) * | 1953-07-02 | 1957-10-22 | Abbott Lab | Basic salicylamides |
| FR5342M (enExample) * | 1966-03-08 | 1967-09-04 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2753350A (en) * | 1951-11-01 | 1956-07-03 | Hasselstrom Torsten | Pungent-tasting pentavalent piperazine diacid salts |
| CH602687A5 (enExample) * | 1973-03-12 | 1978-07-31 | Kali Chemie Ag | |
| US3980643A (en) * | 1974-01-04 | 1976-09-14 | Hokuriku Pharmaceutical Co., Ltd. | Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof |
| US4346231A (en) * | 1978-12-20 | 1982-08-24 | Ponticello Ignazio S | Polymerizable ethylenically unsaturated amide compounds |
-
1980
- 1980-11-20 IT IT26131/80A patent/IT1194819B/it active
-
1981
- 1981-03-26 BE BE0/204274A patent/BE888139A/fr not_active IP Right Cessation
- 1981-03-27 FR FR8106242A patent/FR2494269A1/fr active Granted
- 1981-04-01 DE DE3113087A patent/DE3113087C2/de not_active Expired
- 1981-04-02 AT AT0153281A patent/AT374470B/de not_active IP Right Cessation
- 1981-04-10 GB GB8111393A patent/GB2087869B/en not_active Expired
- 1981-11-02 ZA ZA817568A patent/ZA817568B/xx unknown
- 1981-11-19 JP JP56186771A patent/JPS57116058A/ja active Pending
- 1981-11-19 US US06/322,855 patent/US4420482A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2810718A (en) * | 1953-07-02 | 1957-10-22 | Abbott Lab | Basic salicylamides |
| FR5342M (enExample) * | 1966-03-08 | 1967-09-04 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11388608B2 (en) * | 2019-08-05 | 2022-07-12 | Cisco Technology, Inc. | Soft service migration between spectrum access system (SAS) providers for citizens broadband radio service (CBRS) networks |
Also Published As
| Publication number | Publication date |
|---|---|
| AT374470B (de) | 1984-04-25 |
| DE3113087C2 (de) | 1984-06-14 |
| GB2087869B (en) | 1984-03-28 |
| US4420482A (en) | 1983-12-13 |
| BE888139A (fr) | 1981-07-16 |
| ZA817568B (en) | 1982-10-27 |
| FR2494269B1 (enExample) | 1984-03-23 |
| JPS57116058A (en) | 1982-07-19 |
| IT1194819B (it) | 1988-09-28 |
| ATA153281A (de) | 1983-09-15 |
| GB2087869A (en) | 1982-06-03 |
| DE3113087A1 (de) | 1982-06-09 |
| IT8026131A0 (it) | 1980-11-20 |
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