JPS6144869A - イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤 - Google Patents

イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤

Info

Publication number: JPS6144869A
Authority: JP; Japan
Prior art keywords: imidazole; reduced pressure; residue; methoxy; under reduced
Prior art date: 1984-08-10
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

Application number

JP59167608A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0530832B2 (da

Inventor

Yasuhiro Kumonaka

恭裕雲中

Kazuhiro Omori

和弘大森

Masafumi Yaguchi

理史矢口

Toshio Wakabayashi

若林　利生

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Terumo Corp

Original Assignee

Terumo Corp

Priority date (The priority date 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 date listed.)

1984-08-10

Filing date

1984-08-10

Publication date

1986-03-04

1984-08-10 Application filed by Terumo Corp filed Critical Terumo Corp

1984-08-10 Priority to JP59167608A priority Critical patent/JPS6144869A/ja

1986-03-04 Publication of JPS6144869A publication Critical patent/JPS6144869A/ja

1993-05-11 Publication of JPH0530832B2 publication Critical patent/JPH0530832B2/ja

Status Granted legal-status Critical Current

Links

150000002460 imidazoles Chemical class 0.000 title abstract description 51
208000010110 spontaneous platelet aggregation Diseases 0.000 title abstract description 19
210000001772 blood platelet Anatomy 0.000 title abstract 2
239000003112 inhibitor Substances 0.000 title abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 32
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 14
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 93
150000001875 compounds Chemical class 0.000 abstract description 21
206010027476 Metastases Diseases 0.000 abstract description 7
230000009401 metastasis Effects 0.000 abstract description 7
206010028980 Neoplasm Diseases 0.000 abstract description 6
201000011510 cancer Diseases 0.000 abstract description 6
208000007536 Thrombosis Diseases 0.000 abstract description 4
230000003405 preventing effect Effects 0.000 abstract description 4
239000000463 material Substances 0.000 abstract description 3
150000001412 amines Chemical class 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 119
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
230000002829 reductive effect Effects 0.000 description 55
239000000243 solution Substances 0.000 description 50
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
238000010992 reflux Methods 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 25
239000012300 argon atmosphere Substances 0.000 description 22
238000004440 column chromatography Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000010438 heat treatment Methods 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
239000012044 organic layer Substances 0.000 description 18
238000001816 cooling Methods 0.000 description 17
238000004611 spectroscopical analysis Methods 0.000 description 16
239000007810 chemical reaction solvent Substances 0.000 description 15
239000012452 mother liquor Substances 0.000 description 15
238000010898 silica gel chromatography Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
238000001035 drying Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
238000000605 extraction Methods 0.000 description 10
-1 methoxyethoxymethyl group Chemical group 0.000 description 10
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 9
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
230000002401 inhibitory effect Effects 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
229920005654 Sephadex Polymers 0.000 description 7
239000012507 Sephadex™ Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 6
101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 6
229940127218 antiplatelet drug Drugs 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
230000000694 effects Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000106 platelet aggregation inhibitor Substances 0.000 description 6
239000012298 atmosphere Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
238000005406 washing Methods 0.000 description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000004220 aggregation Methods 0.000 description 4
230000002776 aggregation Effects 0.000 description 4
239000003146 anticoagulant agent Substances 0.000 description 4
102000008186 Collagen Human genes 0.000 description 3
108010035532 Collagen Proteins 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000000702 anti-platelet effect Effects 0.000 description 3
229940114079 arachidonic acid Drugs 0.000 description 3
235000021342 arachidonic acid Nutrition 0.000 description 3
229920001436 collagen Polymers 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
230000003449 preventive effect Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 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
238000000034 method Methods 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
CHZXTOCAICMPQR-UHFFFAOYSA-N 2-(2-bromoethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCBr)C(=O)C2=C1 CHZXTOCAICMPQR-UHFFFAOYSA-N 0.000 description 1
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 1
OQUFOZNPBIIJTN-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;sodium Chemical compound [Na].OC(=O)CC(O)(C(O)=O)CC(O)=O OQUFOZNPBIIJTN-UHFFFAOYSA-N 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
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 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
206010008111 Cerebral haemorrhage Diseases 0.000 description 1
206010008132 Cerebral thrombosis Diseases 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
201000001429 Intracranial Thrombosis Diseases 0.000 description 1
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 1
241000699670 Mus sp. Species 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
WGCOQYDRMPFAMN-ZDUSSCGKSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyrimidin-5-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=NC=1 WGCOQYDRMPFAMN-ZDUSSCGKSA-N 0.000 description 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
238000011047 acute toxicity test Methods 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000001715 carotid artery Anatomy 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
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
OKKJLVBELUTLKV-MZCSYVLQSA-N deuterated methanol Substances [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
230000002101 lytic effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
YZYDOFGGDSDUPX-UHFFFAOYSA-M sodium;carbonic acid;chloride Chemical compound [Na+].[Cl-].OC(O)=O YZYDOFGGDSDUPX-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP59167608A 1984-08-10 1984-08-10 イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤 Granted JPS6144869A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP59167608A JPS6144869A (ja)	1984-08-10	1984-08-10	イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59167608A JPS6144869A (ja)	1984-08-10	1984-08-10	イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤

Publications (2)

Publication Number	Publication Date
JPS6144869A true JPS6144869A (ja)	1986-03-04
JPH0530832B2 JPH0530832B2 (da)	1993-05-11

Family

ID=15852929

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59167608A Granted JPS6144869A (ja)	1984-08-10	1984-08-10	イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤

Country Status (1)

Country	Link
JP (1)	JPS6144869A (da)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4786646A (en) *	1987-07-10	1988-11-22	Hoffmann-La Roche Inc.	Cyclopropylpropenamides
US4788206A (en) *	1987-07-10	1988-11-29	Hoffmann-La Roche Inc.	Pentadieneamides
EP0298466A2 (en) *	1987-07-10	1989-01-11	F. Hoffmann-La Roche Ag	Substituted alkene carboxylic acid amides and derivatives
US4927826A (en) *	1987-07-10	1990-05-22	Hoffman-La Roche Inc.	Cycloproylpropenamides useful as platelet activing factor (PAF) antagonists
JP2004161774A (ja) *	2002-11-14	2004-06-10	Samsung Electronics Co Ltd	耐光性を有する化合物及びこれを含むインク組成物

1984
- 1984-08-10 JP JP59167608A patent/JPS6144869A/ja active Granted

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4786646A (en) *	1987-07-10	1988-11-22	Hoffmann-La Roche Inc.	Cyclopropylpropenamides
US4788206A (en) *	1987-07-10	1988-11-29	Hoffmann-La Roche Inc.	Pentadieneamides
EP0298466A2 (en) *	1987-07-10	1989-01-11	F. Hoffmann-La Roche Ag	Substituted alkene carboxylic acid amides and derivatives
US4927826A (en) *	1987-07-10	1990-05-22	Hoffman-La Roche Inc.	Cycloproylpropenamides useful as platelet activing factor (PAF) antagonists
JP2004161774A (ja) *	2002-11-14	2004-06-10	Samsung Electronics Co Ltd	耐光性を有する化合物及びこれを含むインク組成物

Also Published As

Publication number	Publication date
JPH0530832B2 (da)	1993-05-11

Publication	Publication Date	Title
RU2128648C1 (ru)	1999-04-10	Производные сульфонамида, способы их получения, фармацевтическая композиция и способ лечения
JP2657760B2 (ja)	1997-09-24	４−アミノキナゾリン誘導体およびそれを含有する医薬品
McEvoy et al.	1974	6-(Substituted phenyl)-5-substituted-4, 5-dihydro-3 (2H)-pyridazinones. Antihypertensive agents
JPS5883691A (ja)	1983-05-19	１′，２′−ジアシル−（６ｒ，ｓ）−５，６，７，８−テトラヒドロ−ｌ−ビオプテリンおよびその製法
JPH07500575A (ja)	1995-01-19	ガリウム（３）錯体、その製造方法、及びそれを含有する医薬組成物
AU653024B2 (en)	1994-09-15	Substituted diaminophthalimides and analogues
US3338888A (en)	1967-08-29	Rifamycin type antibiotic compounds
HU176251B (en)	1981-01-28	Process for producing 2,4,6-triiodo-benzoic acid derivatives substituted with 2,4,6-triiodo-benzoyl-amino-alkyl-acetamido group
US3689652A (en)	1972-09-05	Method of lowering blood pressure in mammals
JPS6144869A (ja)	1986-03-04	イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤
Delia et al.	1966	Purine N-Oxides. XVII. The Oxidation of Guanine at Position 71
Bagli et al.	1961	Arylation of Quinones by Diazonium Salts: vii. Synthesis And Structure of Some aryl-chloro-p-benzoquinones
US6114360A (en)	2000-09-05	Pyrrole compounds
JP3465827B2 (ja)	2003-11-10	アザインドール誘導体およびこれを有効成分とする抗潰瘍薬
JPS62270564A (ja)	1987-11-24	ピラジン誘導体およびこれを含有する血小板凝集抑制剤
Ning et al.	1973	Carbon-nitrogen vs nitrogen-nitrogen bond formation in nitrenoid cyclization reactions. Pyrolysis of 3-azido-4-(2-pyridyl) carbostyrils
JPS597188A (ja)	1984-01-14	チオホルムアミド誘導体およびその製造法
US2508418A (en)	1950-05-23	Nu-substituted poly-iodo phthalimides
JPS6144870A (ja)	1986-03-04	不飽和脂肪酸アミド誘導体およびこれを含有する血小板凝集抑制剤
Osner et al.	1963	Pyridazines I. 4‐halo‐5‐hydrazino‐3‐pyridazone and its derivatives
FR2612515A1 (fr)	1988-09-23	Derives substitues de la benzidine, leur procede de fabrication et leur application dans le domaine therapeutique
JPS59199682A (ja)	1984-11-12	２−ｎ−シクロアルキルメチル−３−オキソ−５，６−ジアリ−ルトリアジン誘導体
JPS6025923A (ja)	1985-02-08	５−リポキシゲナ−ゼ阻害剤
Baas et al.	1966	The bromination of 1, 4‐Di‐tert. Butylbenzene: Synthesis of 1, 4‐di‐tert. butyl‐2‐bromobenzene and some tert. butyl‐dibromobenzenes
JPS5821634B2 (ja)	1983-05-02	シンキイミダゾ（１，２−ａ）ｓ− トリアジンルイノセイゾウホウホウ

JPS6144869A - イミダゾ−ル誘導体およびこれを含有する血小板凝集抑制剤 - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15852929

Family Applications (1)

Country Status (1)

Cited By (5)

Cited By (5)

Also Published As

Similar Documents