DE3113150C2 - Kristallines N,N'-Bis-(3-picolyl)-4-methoxy-isophthalamid-monohydrat, Verfahren zu seiner Herstellung und dieses enthaltende, pharmazeutische Mittel - Google Patents
Kristallines N,N'-Bis-(3-picolyl)-4-methoxy-isophthalamid-monohydrat, Verfahren zu seiner Herstellung und dieses enthaltende, pharmazeutische MittelInfo
- Publication number
- DE3113150C2 DE3113150C2 DE3113150A DE3113150A DE3113150C2 DE 3113150 C2 DE3113150 C2 DE 3113150C2 DE 3113150 A DE3113150 A DE 3113150A DE 3113150 A DE3113150 A DE 3113150A DE 3113150 C2 DE3113150 C2 DE 3113150C2
- Authority
- DE
- Germany
- Prior art keywords
- monohydrate
- water
- crystalline
- anhydrous
- methoxy
- 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 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- ICYQAMNVLLHURR-UHFFFAOYSA-N 4-methoxy-1-n,3-n-bis(pyridin-3-ylmethyl)benzene-1,3-dicarboxamide;hydrate Chemical compound O.COC1=CC=C(C(=O)NCC=2C=NC=CC=2)C=C1C(=O)NCC1=CC=CN=C1 ICYQAMNVLLHURR-UHFFFAOYSA-N 0.000 title 1
- 230000000694 effects Effects 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 230000009424 thromboembolic effect Effects 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000013078 crystal Substances 0.000 claims description 17
- 210000004369 blood Anatomy 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 14
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 238000012982 x-ray structure analysis Methods 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 1
- 108090000190 Thrombin Proteins 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims 1
- 229960004072 thrombin Drugs 0.000 claims 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 description 24
- 229960001006 picotamide Drugs 0.000 description 23
- 150000004682 monohydrates Chemical class 0.000 description 15
- 230000002744 anti-aggregatory effect Effects 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 230000003480 fibrinolytic effect Effects 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 210000002381 plasma Anatomy 0.000 description 6
- 241000282412 Homo Species 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000700198 Cavia Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000003814 drug Substances 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 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 1
- QGXLVXZRPRRCRP-IDIVVRGQSA-L Adenosine 5'-phosphate disodium Chemical compound [Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O QGXLVXZRPRRCRP-IDIVVRGQSA-L 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000007675 cardiac surgery Methods 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000001 effect on platelet aggregation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001550 time effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 208000019553 vascular disease Diseases 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE3113150A1 DE3113150A1 (de) | 1982-01-28 |
| DE3113150C2 true DE3113150C2 (de) | 1985-05-15 |
Family
ID=11266904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3113150A Expired DE3113150C2 (de) | 1980-04-23 | 1981-04-01 | Kristallines N,N'-Bis-(3-picolyl)-4-methoxy-isophthalamid-monohydrat, Verfahren zu seiner Herstellung und dieses enthaltende, pharmazeutische Mittel |
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
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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Legal Events
| Date | Code | Title | Description |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: INTERNATIONAL LICENSING AND SERVICES B.V., AMSTERD |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: GRUENECKER, A., DIPL.-ING. KINKELDEY, H., DIPL.-ING. DR.-ING. STOCKMAIR, W., DIPL.-ING. DR.-ING. AE.E. CAL TECH SCHUMANN, K., DIPL.-PHYS. DR.RER.NAT. JAKOB, P., DIPL.-ING. BEZOLD, G., DIPL.-CHEM. DR.RER.NAT. MEISTER, W., DIPL.-ING. HILGERS, H., DIPL.-ING. MEYER-PLATH, H., DIPL.-ING. DR.-ING. KINKELDEY, U., DIPL.-BIOL. DR.RER.NAT. BOTT-BODENHAUSEN, M., DIPL.-PHYS. DR.RER.NAT. EHNOLD, A., DIPL.-ING. SCHUSTER, T., DIPL.-PHYS., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SANDOZ-PATENT-GMBH, 7850 LOERRACH, DE |
|
| 8339 | Ceased/non-payment of the annual fee |