CA1129419A - Monohydrated isophthalic acid picolylamide, process of preparation and pharmaceutical use thereof - Google Patents
Monohydrated isophthalic acid picolylamide, process of preparation and pharmaceutical use thereofInfo
- Publication number
- CA1129419A CA1129419A CA375,430A CA375430A CA1129419A CA 1129419 A CA1129419 A CA 1129419A CA 375430 A CA375430 A CA 375430A CA 1129419 A CA1129419 A CA 1129419A
- Authority
- CA
- Canada
- Prior art keywords
- picotamide
- monohydrated
- water
- anhydrous
- activity
- 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 description 17
- 230000008569 process Effects 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 3
- CSOZOOLWVJMGQW-UHFFFAOYSA-N 3-(pyridin-2-ylmethylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)NCC=2N=CC=CC=2)=C1 CSOZOOLWVJMGQW-UHFFFAOYSA-N 0.000 title 1
- KYWCWBXGRWWINE-UHFFFAOYSA-N 4-methoxy-N1,N3-bis(3-pyridinylmethyl)benzene-1,3-dicarboxamide Chemical compound COC1=CC=C(C(=O)NCC=2C=NC=CC=2)C=C1C(=O)NCC1=CC=CN=C1 KYWCWBXGRWWINE-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000000126 substance Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- JIICYHFLIOGGHE-UHFFFAOYSA-N 4-methoxybenzene-1,3-dicarboxylic acid Chemical class COC1=CC=C(C(O)=O)C=C1C(O)=O JIICYHFLIOGGHE-UHFFFAOYSA-N 0.000 claims description 2
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 28
- 230000009424 thromboembolic effect Effects 0.000 abstract description 4
- 229960001006 picotamide Drugs 0.000 description 52
- 210000001772 blood platelet Anatomy 0.000 description 18
- 230000002744 anti-aggregatory effect Effects 0.000 description 14
- 239000003146 anticoagulant agent Substances 0.000 description 14
- 230000036765 blood level Effects 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 10
- 230000003480 fibrinolytic effect Effects 0.000 description 9
- 150000004682 monohydrates Chemical class 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 230000036571 hydration Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 210000002381 plasma Anatomy 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000009089 cytolysis Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960005419 nitrogen Drugs 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000001550 time effect Effects 0.000 description 3
- FKPCRVTXBLUQBV-UHFFFAOYSA-N 4-methoxybenzene-1,3-dicarbonyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1C(Cl)=O FKPCRVTXBLUQBV-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003527 fibrinolytic agent Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- 241000700198 Cavia Species 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- ORKSTPSQHZNDSC-IDIVVRGQSA-L disodium;[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphate Chemical compound [Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O ORKSTPSQHZNDSC-IDIVVRGQSA-L 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229940012982 picot Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT48494A80 | 1980-04-23 | ||
| IT48494/80A IT1143942B (it) | 1980-04-23 | 1980-04-23 | Picolilammide idrata di acido isoftalico ad azione antiaggregante piastrinica antitrombinica ed anticoagulante e procedimento per la sua preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129419A true CA1129419A (en) | 1982-08-10 |
Family
ID=11266904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA375,430A Expired CA1129419A (en) | 1980-04-23 | 1981-04-14 | Monohydrated isophthalic acid picolylamide, process of preparation and pharmaceutical use thereof |
Country Status (23)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1214915B (it) * | 1985-10-10 | 1990-01-31 | Manetti & Roberts Italo Brit | Derivato dell'acido 4-metossiisoftalico con attivita'farmacologica in disordini tromboembolici e procedimento per la sua preparazione |
| US5227492A (en) * | 1988-01-20 | 1993-07-13 | Yamanouchi Pharmaceutical Co., Ltd. | Diurea derivatives useful as medicaments and processes for the preparation thereof |
| TW200900393A (en) * | 2007-05-21 | 2009-01-01 | Dybly Ag | Salts of picotamide |
| CN111154114A (zh) * | 2019-12-31 | 2020-05-15 | 肇庆学院 | 一种基于5-乙氧基间苯二甲酸的锌(ⅱ)金属有机配位化合物及其制备方法 |
| CN111154113A (zh) * | 2019-12-31 | 2020-05-15 | 肇庆学院 | 一种基于双核钴(ⅱ)的金属有机配合物及其制备方法 |
| CN112159347B (zh) * | 2020-10-27 | 2022-06-07 | 常州工程职业技术学院 | 吡考他胺的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL149810B (nl) * | 1969-04-21 | 1976-06-15 | Lilly Co Eli | Werkwijze ter bereiding van een farmaceutisch preparaat door kristallijn cefalexine in een voor therapeutische toediening geschikte vorm te brengen, gevormde farmaceutische preparaten, alsmede werkwijze ter bereiding van voor bovengenoemde toepassing geschikt cefalexine. |
| IT1016005B (it) * | 1970-07-01 | 1977-05-30 | Manetti & Roberts Italo Brit | Picolilamidi dell acido 4 idrossi isoftalico e suoi derivati e relativo procedimento di prepara zione |
| US3973026A (en) * | 1975-02-05 | 1976-08-03 | Societa Italo-Britannica L. Manetti-H. Roberts & C. | Inhibitor of blood plate aggregation |
-
1980
- 1980-04-23 IT IT48494/80A patent/IT1143942B/it active Protection Beyond IP Right Term
-
1981
- 1981-03-27 SE SE8101963A patent/SE438674B/sv not_active IP Right Cessation
- 1981-03-27 IL IL62509A patent/IL62509A/xx not_active IP Right Cessation
- 1981-03-30 NZ NZ196677A patent/NZ196677A/xx unknown
- 1981-04-01 DE DE3113150A patent/DE3113150C2/de not_active Expired
- 1981-04-07 CH CH2531/81A patent/CH649533A5/it not_active IP Right Cessation
- 1981-04-08 AU AU69310/81A patent/AU537921B2/en not_active Ceased
- 1981-04-09 ZA ZA00812362A patent/ZA812362B/xx unknown
- 1981-04-09 IE IE808/81A patent/IE51218B1/en not_active IP Right Cessation
- 1981-04-10 AT AT0166481A patent/AT375645B/de not_active IP Right Cessation
- 1981-04-14 CA CA375,430A patent/CA1129419A/en not_active Expired
- 1981-04-20 ES ES501470A patent/ES8203086A1/es not_active Expired
- 1981-04-21 DK DK177281A patent/DK155735C/da not_active IP Right Cessation
- 1981-04-21 PT PT72899A patent/PT72899B/pt not_active IP Right Cessation
- 1981-04-22 FI FI811257A patent/FI74951C/fi not_active IP Right Cessation
- 1981-04-22 JP JP56061120A patent/JPS6043063B2/ja not_active Expired
- 1981-04-22 NO NO811360A patent/NO154193C/no unknown
- 1981-04-22 GB GB8112454A patent/GB2080288B/en not_active Expired
- 1981-04-22 DD DD81229409A patent/DD158397A5/de not_active IP Right Cessation
- 1981-04-23 NL NLAANVRAGE8102016,A patent/NL186860C/xx not_active IP Right Cessation
- 1981-04-23 BE BE2/59122A patent/BE888528A/nl not_active IP Right Cessation
- 1981-04-23 OA OA57386A patent/OA06795A/xx unknown
- 1981-04-23 FR FR8108501A patent/FR2481283B1/fr not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |