KR880001865B1 - 4-(1-이미다졸일메틸)신남산 하이드로클로라이드 모노하이드레이트의 제조방법 - Google Patents
4-(1-이미다졸일메틸)신남산 하이드로클로라이드 모노하이드레이트의 제조방법 Download PDFInfo
- Publication number
- KR880001865B1 KR880001865B1 KR8200564A KR820000564A KR880001865B1 KR 880001865 B1 KR880001865 B1 KR 880001865B1 KR 8200564 A KR8200564 A KR 8200564A KR 820000564 A KR820000564 A KR 820000564A KR 880001865 B1 KR880001865 B1 KR 880001865B1
- Authority
- KR
- South Korea
- Prior art keywords
- cinnamic acid
- imidazolylmethyl
- acid hydrochloride
- hydrochloride monohydrate
- preparing
- 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
- OECPYFQNYXUDJF-UHFFFAOYSA-N 3-[4-(1h-imidazol-2-ylmethyl)phenyl]prop-2-enoic acid;hydrochloride Chemical compound Cl.C1=CC(C=CC(=O)O)=CC=C1CC1=NC=CN1 OECPYFQNYXUDJF-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 33
- BVGINDBNCSPHPC-UHFFFAOYSA-N 3-[4-(1h-imidazol-2-ylmethyl)phenyl]prop-2-enoic acid;hydrate;hydrochloride Chemical compound O.Cl.C1=CC(C=CC(=O)O)=CC=C1CC1=NC=CN1 BVGINDBNCSPHPC-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001953 recrystallisation Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 239000000454 talc Substances 0.000 description 7
- 235000012222 talc Nutrition 0.000 description 7
- 229910052623 talc Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- -1 inflammation Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- ZIRVAUOPXCOSFU-UHFFFAOYSA-N ethyl 3-[4-(bromomethyl)phenyl]prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(CBr)C=C1 ZIRVAUOPXCOSFU-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZBBXVXQWKNEZKK-UHFFFAOYSA-N 3-[4-(1h-imidazol-2-ylmethyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1CC1=NC=CN1 ZBBXVXQWKNEZKK-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001466453 Laminaria Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- BYKCCSOUMNMLSV-UHFFFAOYSA-N ethyl 3-[4-(1h-imidazol-2-ylmethyl)phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OCC)=CC=C1CC1=NC=CN1 BYKCCSOUMNMLSV-UHFFFAOYSA-N 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007941 film coated tablet Substances 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
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process 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
- 239000000644 isotonic solution Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP81-18488 | 1981-02-10 | ||
| JP56018488A JPS57131769A (en) | 1981-02-10 | 1981-02-10 | 4-(1-imidazolylmethyl)cinnamic acid hydrochloride monohydrate, its preparation and drug containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009043A KR830009043A (ko) | 1983-12-17 |
| KR880001865B1 true KR880001865B1 (ko) | 1988-09-23 |
Family
ID=11973016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8200564A Expired KR880001865B1 (ko) | 1981-02-10 | 1982-02-10 | 4-(1-이미다졸일메틸)신남산 하이드로클로라이드 모노하이드레이트의 제조방법 |
Country Status (14)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855466A (ja) * | 1981-09-28 | 1983-04-01 | Kissei Pharmaceut Co Ltd | 新規な１，３−二置換イミダゾ−ル誘導体及びその製造方法 |
| TW208013B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd | |
| US5215973A (en) * | 1991-03-07 | 1993-06-01 | Magis Farmaceutici S.P.A. | Optically active and racemic hydrated diacetylesters of α-glycero-phosphoryl-choline |
| CN114436964A (zh) * | 2020-10-16 | 2022-05-06 | 赤峰经方医药技术开发有限责任公司 | 一种奥扎格雷的连续制备方法 |
| US20240336638A1 (en) * | 2021-07-01 | 2024-10-10 | Guoqin ZHUGE | Imidazole compound, and intermediate and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55313A (en) * | 1978-06-13 | 1980-01-05 | Kissei Pharmaceut Co Ltd | Imidazole derivative |
-
1981
- 1981-02-10 JP JP56018488A patent/JPS57131769A/ja active Granted
-
1982
- 1982-02-02 ZA ZA82639A patent/ZA82639B/xx unknown
- 1982-02-03 AU AU80154/82A patent/AU546907B2/en not_active Ceased
- 1982-02-05 FI FI820379A patent/FI77028C/fi not_active IP Right Cessation
- 1982-02-05 GR GR67226A patent/GR75408B/el unknown
- 1982-02-08 CA CA000395781A patent/CA1173839A/en not_active Expired
- 1982-02-09 IE IE289/82A patent/IE52519B1/en not_active IP Right Cessation
- 1982-02-09 DE DE8282300619T patent/DE3261987D1/de not_active Expired
- 1982-02-09 ES ES509459A patent/ES8302664A1/es not_active Expired
- 1982-02-09 EP EP82300619A patent/EP0058079B1/en not_active Expired
- 1982-02-09 YU YU274/82A patent/YU42757B/xx unknown
- 1982-02-09 DK DK054982A patent/DK155736C/da not_active IP Right Cessation
- 1982-02-10 KR KR8200564A patent/KR880001865B1/ko not_active Expired
- 1982-02-10 US US06/347,616 patent/US4607046A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES509459A0 (es) | 1983-01-16 |
| ES8302664A1 (es) | 1983-01-16 |
| AU546907B2 (en) | 1985-09-26 |
| EP0058079A2 (en) | 1982-08-18 |
| FI77028C (fi) | 1989-01-10 |
| IE820289L (en) | 1982-08-10 |
| CA1173839A (en) | 1984-09-04 |
| YU42757B (en) | 1988-12-31 |
| DK54982A (da) | 1982-08-11 |
| FI820379L (fi) | 1982-08-11 |
| IE52519B1 (en) | 1987-11-25 |
| FI77028B (fi) | 1988-09-30 |
| US4607046A (en) | 1986-08-19 |
| GR75408B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-13 |
| ZA82639B (en) | 1983-01-26 |
| DK155736B (da) | 1989-05-08 |
| YU27482A (en) | 1985-03-20 |
| EP0058079A3 (en) | 1982-09-08 |
| AU8015482A (en) | 1982-08-19 |
| DE3261987D1 (en) | 1985-03-07 |
| JPS57131769A (en) | 1982-08-14 |
| EP0058079B1 (en) | 1985-01-23 |
| DK155736C (da) | 1989-09-25 |
| KR830009043A (ko) | 1983-12-17 |
| JPH0234941B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU732489B2 (en) | Oral compositions of levosimendan | |
| US5541209A (en) | Method of treating or preventing cardiac arrhythmia employing an N-substituted heterocyclic derivative | |
| EP0579681B1 (en) | Crystalline tiagabine hydrochloride monohydrate, its preparation and use | |
| EP0346883A2 (en) | Expectorant comprising hydroxy-alkylcysteine derivative | |
| KR880001865B1 (ko) | 4-(1-이미다졸일메틸)신남산 하이드로클로라이드 모노하이드레이트의 제조방법 | |
| FI71319B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbart vicaminsackarinat | |
| JPH02300184A (ja) | インドール誘導体 | |
| CZ321095A3 (en) | Heterocyclic compounds | |
| US4668674A (en) | (+)-6-chloro-5,10-dihydro-5-[(1-methyl-4-piperidinyl)-acetyl]-11H-dibenzo[b,][1,4]diazepin-11-one, the isolation thereof and its use as a pharmaceutical material | |
| US4927821A (en) | Enol ethers of 6-chloro-4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide, and their use | |
| MXPA03005884A (es) | Hemimaleato de amlodipina. | |
| KR950014866B1 (ko) | 에르골리닐 헤테로사이클 | |
| KR102170422B1 (ko) | 토파시티닙의 신규 염, 이의 제조방법 및 이를 포함하는 약학 조성물 | |
| EP0003286B1 (de) | Ergopeptidalkaloid-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| EP0736526A1 (en) | Pyrazolidine derivative, radical scavenger, brain-infarction depressant, and brain-edema depressant | |
| EP0119541A1 (en) | Substituted 4,10-dihydro-10-oxothieno-benzoxepins, a process for their preparation and their use as medicaments | |
| JPH032183A (ja) | ビスベンジルイソキノリン誘導体 | |
| JP2860385B2 (ja) | ビスべンジルイソキノリン誘導体 | |
| FI78696C (fi) | Foerfarande foer framstaellning av smaertstillande 11-/ -(karboximetyl)tio/halogendibenso/b,f/oxepin. | |
| JPH02292213A (ja) | 制癌剤 | |
| JPH0368578A (ja) | ビスベンジルイソキノリン誘導体 | |
| KR900008563B1 (ko) | 에르고트 유도체의 제조방법 | |
| JPH02134382A (ja) | ビスベンジルイソキノリン誘導体 | |
| CA2257931C (en) | Modified form of the r(-)-n-(4,4-di(3-methylthien-2-yl)but-3-enyl)-nipecotic acid hydrochloride | |
| KR820001284B1 (ko) | 이미다조[1, 2-a]이미다졸의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19820210 |
|
| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19870209 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19820210 Comment text: Patent Application |
|
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19880820 |
|
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19881130 |
|
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19881209 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 19881209 End annual number: 3 Start annual number: 1 |
|
| PR1001 | Payment of annual fee |
Payment date: 19911022 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 19920813 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 19930810 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 19940811 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 19950818 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 19960828 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 19970829 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 19971230 Start annual number: 11 End annual number: 14 |
|
| PC1801 | Expiration of term |