NL7906148A - Nieuwe imidazoolderivaten. - Google Patents

Nieuwe imidazoolderivaten. Download PDF

Info

Publication number: NL7906148A
Authority: NL; Netherlands
Prior art keywords: group; formula; carbon atoms; compound; alkyl group
Prior art date: 1978-08-15

Application number

NL7906148A

Other languages

English (en)

Dutch (nl)

Original Assignee

Pfizer

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.)

1978-08-15

Filing date

1979-08-13

Publication date

1980-02-19

1979-08-13 Application filed by Pfizer filed Critical Pfizer

1980-02-19 Publication of NL7906148A publication Critical patent/NL7906148A/nl

Links

150000001875 compounds Chemical class 0.000 claims description 47
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 21
-1 2-quinolyl group Chemical group 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 7
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 6
150000002460 imidazoles Chemical class 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000012312 sodium hydride Substances 0.000 claims description 3
229910000104 sodium hydride Inorganic materials 0.000 claims description 3
WTFVSJLMTDQLMM-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-3-phenylmethoxypyridine Chemical compound C=1C=CC=CC=1COC1=CC=CN=C1CN1C=CN=C1 WTFVSJLMTDQLMM-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
230000004048 modification Effects 0.000 claims 4
238000012986 modification Methods 0.000 claims 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
102000003960 Ligases Human genes 0.000 description 13
108090000364 Ligases Proteins 0.000 description 13
239000003921 oil Substances 0.000 description 13
239000007787 solid Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
230000009471 action Effects 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
206010012601 diabetes mellitus Diseases 0.000 description 8
239000000047 product Substances 0.000 description 8
150000003180 prostaglandins Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
208000019695 Migraine disease Diseases 0.000 description 7
206010027599 migraine Diseases 0.000 description 7
229940094443 oxytocics prostaglandins Drugs 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
241000283973 Oryctolagus cuniculus Species 0.000 description 6
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 6
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
230000002792 vascular Effects 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
208000006011 Stroke Diseases 0.000 description 5
239000000284 extract Substances 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
239000008096 xylene Substances 0.000 description 5
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
206010019233 Headaches Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
208000007536 Thrombosis Diseases 0.000 description 4
229960001138 acetylsalicylic acid Drugs 0.000 description 4
229940114079 arachidonic acid Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
231100000869 headache Toxicity 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
108010064377 prostacyclin synthetase Proteins 0.000 description 4
YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 4
150000003222 pyridines Chemical class 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CJDYNUBRSBSSJU-UHFFFAOYSA-N 2-benzylpyrazol-3-amine Chemical compound NC1=CC=NN1CC1=CC=CC=C1 CJDYNUBRSBSSJU-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
238000004220 aggregation Methods 0.000 description 3
235000021342 arachidonic acid Nutrition 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
210000001589 microsome Anatomy 0.000 description 3
208000010125 myocardial infarction Diseases 0.000 description 3
KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
XMFMTEDYRCFTOH-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-6-methylpyridin-3-ol Chemical compound CC1=CC=C(O)C(CN2C=NC=C2)=N1 XMFMTEDYRCFTOH-UHFFFAOYSA-N 0.000 description 2
YZRAHPJHGZVIMR-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1CN1C=CN=C1 YZRAHPJHGZVIMR-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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230000005856 abnormality Effects 0.000 description 2
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229960000905 indomethacin Drugs 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
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QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
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MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 2
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230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
201000010875 transient cerebral ischemia Diseases 0.000 description 2
MBCWGLWTUUITAZ-UHFFFAOYSA-N (5-methoxypyridin-2-yl)methyl acetate Chemical compound COC1=CC=C(COC(C)=O)N=C1 MBCWGLWTUUITAZ-UHFFFAOYSA-N 0.000 description 1
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
KSBXDCBRSKRVDC-UHFFFAOYSA-N 2-(chloromethyl)-5-methoxypyridine Chemical compound COC1=CC=C(CCl)N=C1 KSBXDCBRSKRVDC-UHFFFAOYSA-N 0.000 description 1
QFLPSIUFCCCRMI-UHFFFAOYSA-N 2-(chloromethyl)-6-methylpyridine;hydron;chloride Chemical compound Cl.CC1=CC=CC(CCl)=N1 QFLPSIUFCCCRMI-UHFFFAOYSA-N 0.000 description 1
WDETYCRYUBGKCE-UHFFFAOYSA-N 2-(chloromethyl)quinolin-1-ium;chloride Chemical compound Cl.C1=CC=CC2=NC(CCl)=CC=C21 WDETYCRYUBGKCE-UHFFFAOYSA-N 0.000 description 1
GUJWQLZYJBHOLQ-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-3-methoxy-6-methylpyridine Chemical compound COC1=CC=C(C)N=C1CN1C=NC=C1 GUJWQLZYJBHOLQ-UHFFFAOYSA-N 0.000 description 1
ZQIDJVLVYDQXOD-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-3-methoxypyridine Chemical compound COC1=CC=CN=C1CN1C=NC=C1 ZQIDJVLVYDQXOD-UHFFFAOYSA-N 0.000 description 1
GAMSBPSEJOWPEQ-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-4-methylpyridin-3-ol Chemical compound CC1=CC=NC(CN2C=NC=C2)=C1O GAMSBPSEJOWPEQ-UHFFFAOYSA-N 0.000 description 1
INUHNTIKBKQOQA-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-5-methoxypyridine Chemical compound N1=CC(OC)=CC=C1CN1C=NC=C1 INUHNTIKBKQOQA-UHFFFAOYSA-N 0.000 description 1
SZTDQMVCLDLWKZ-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)-5-methoxypyridine;dihydrochloride Chemical compound Cl.Cl.N1=CC(OC)=CC=C1CN1C=NC=C1 SZTDQMVCLDLWKZ-UHFFFAOYSA-N 0.000 description 1
OLVXNUWIZMHSKC-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)pyridin-3-ol Chemical compound OC1=CC=CN=C1CN1C=NC=C1 OLVXNUWIZMHSKC-UHFFFAOYSA-N 0.000 description 1
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AWINCEWZDZOXHT-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-4-methylpyridin-3-ol Chemical compound CN(C)CC1=NC=CC(C)=C1O AWINCEWZDZOXHT-UHFFFAOYSA-N 0.000 description 1
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RSOPTYAZDFSMTN-UHFFFAOYSA-N 2-chloropyridin-3-ol Chemical compound OC1=CC=CN=C1Cl RSOPTYAZDFSMTN-UHFFFAOYSA-N 0.000 description 1
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KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
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230000004075 alteration Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
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230000007214 atherothrombosis Effects 0.000 description 1
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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 1
230000001851 biosynthetic effect Effects 0.000 description 1
230000036765 blood level Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000006227 byproduct Substances 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
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
230000035602 clotting Effects 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
230000010339 dilation Effects 0.000 description 1
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
229960002986 dinoprostone Drugs 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
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ANBZWDBEKOZNHY-UHFFFAOYSA-N ethanol;oxalic acid Chemical compound CCO.OC(=O)C(O)=O ANBZWDBEKOZNHY-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000009472 formulation Methods 0.000 description 1
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230000013632 homeostatic process Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
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230000035874 hyperreactivity Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
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239000011147 inorganic material Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000003446 ligand Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
229940118019 malondialdehyde Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
101150095588 pgi2 gene Proteins 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 1
BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000008684 selective degradation Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
210000003462 vein Anatomy 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
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

NL7906148A 1978-08-15 1979-08-13 Nieuwe imidazoolderivaten. NL7906148A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB7833456		1978-08-15
GB7833456		1978-08-15
GB7926146A GB2028317B (en)	1978-08-15	1979-07-26	2-(imidazol-1-ylmethyl)-pyridine and -quinoline thromboxane synthetase inhibitors
GB7926146		1979-07-26

Publications (1)

Publication Number	Publication Date
NL7906148A true NL7906148A (nl)	1980-02-19

Family

ID=26268547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7906148A NL7906148A (nl)	1978-08-15	1979-08-13	Nieuwe imidazoolderivaten.

Country Status (8)

Country	Link
US (1)	US4230714A (fr)
AU (1)	AU4989579A (fr)
BE (1)	BE878230A (fr)
DE (1)	DE2932967A1 (fr)
FR (1)	FR2433525A1 (fr)
GB (1)	GB2028317B (fr)
LU (1)	LU81598A1 (fr)
NL (1)	NL7906148A (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR71915B (fr) *	1979-11-27	1983-08-16	Pfizer
US4350696A (en) *	1980-03-08	1982-09-21	Pfizer Inc.	Imidazole derivatives, process for their preparation and pharmaceutical compositions thereof
ZA825413B (en) *	1981-08-26	1983-06-29	Pfizer	Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
DE3333314A1 (de) *	1983-09-15	1985-03-28	Hoechst Ag, 6230 Frankfurt	Substituierte pyrido(1,2-c)imidazo(1,2-a)benzimidazole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen
IL82401A0 (en) *	1986-05-06	1987-11-30	Merrell Dow Pharma	Dopamine beta hydroxy-lase inhibiting imidazole derivatives and pharmaceutical compositions containing them
US4906644A (en) *	1986-11-20	1990-03-06	Mitsubishi Kasei Corporation	Lipid-peroxide formation inhibiting composition and novel compounds useful therefor
DE3811574A1 (de) *	1988-03-31	1989-10-19	Schering Ag	N-substituierte imidazole, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
DE4131584A1 (de) *	1991-09-23	1993-03-25	Sandoz Ag	Imidazolylmethyl-pyridine, ihre herstellung und anwendung als pharmazeutika
US5635521A (en) *	1991-09-23	1997-06-03	Sandoz Ltd.	Imidazolylmethyl-pyridines
CN1040107C (zh) *	1993-01-02	1998-10-07	山道士有限公司	咪唑基甲基吡啶
GB0009037D0 (en) *	2000-04-13	2000-05-31	Novartis Ag	Organic compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH204740A (de) *	1935-07-23	1939-05-15	Chem Ind Basel	Verfahren zur Darstellung eines in 2-Stellung substituierten Imidazoldihydrids-(4,5).
NL135940C (fr) *	1965-05-10
FR1479120A (fr) *	1965-05-10	1967-04-28	Ward Blenkinsop & Co Ltd	Composés imidazoliques et leur préparation
US4058614A (en) *	1973-12-04	1977-11-15	Merck & Co., Inc.	Substituted imidazole compounds and therapeutic compositions therewith
DE2418502C3 (de) *	1974-04-11	1980-04-24	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Dichlorbenzyl- [2-( a -imidazolylbutyl)-phenyl] -äther und -thioäther, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel

1979
- 1979-07-26 GB GB7926146A patent/GB2028317B/en not_active Expired
- 1979-07-30 US US06/061,807 patent/US4230714A/en not_active Expired - Lifetime
- 1979-08-13 NL NL7906148A patent/NL7906148A/nl not_active Application Discontinuation
- 1979-08-13 LU LU81598A patent/LU81598A1/fr unknown
- 1979-08-13 BE BE0/196723A patent/BE878230A/fr not_active IP Right Cessation
- 1979-08-14 FR FR7920698A patent/FR2433525A1/fr active Granted
- 1979-08-14 DE DE19792932967 patent/DE2932967A1/de not_active Ceased
- 1979-08-14 AU AU49895/79A patent/AU4989579A/en not_active Abandoned

Also Published As

Publication number	Publication date
GB2028317A (en)	1980-03-05
FR2433525B1 (fr)	1981-12-11
DE2932967A1 (de)	1980-03-20
BE878230A (fr)	1980-02-13
US4230714A (en)	1980-10-28
AU4989579A (en)	1980-02-21
GB2028317B (en)	1982-11-10
LU81598A1 (fr)	1981-03-24
FR2433525A1 (fr)	1980-03-14

Legal Events

Date	Code	Title
1980-03-10	A1A	A request for search or an international-type search has been filed
1981-01-26	BB	A search report has been drawn up
1981-04-27	BC	A request for examination has been filed
1985-01-01	A85	Still pending on 85-01-01
1985-04-01	BV	The patent application has lapsed

Publication	Publication Date	Title
SU1217256A3 (ru)	1986-03-07	Способ получени бензофуранбензо( @ )тиофен-или нафталинкарбоновых кислот или их фармацевтически приемлемых солей
US4448781A (en)	1984-05-15	N-Benzyl-imidazoles as selective inhibitors of the thromboxane synthetase enzyme
US4551468A (en)	1985-11-05	Heterocyclic thromboxane synthetase inhibitors and pharmaceutical compositions containing them
FI66860B (fi)	1984-08-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-1-imidazolylalkyl)indolderivat
US4350696A (en)	1982-09-21	Imidazole derivatives, process for their preparation and pharmaceutical compositions thereof
EP0054417B1 (fr)	1984-12-19	Indoles inhibiteurs de la thromboxane synthétase, procédé de préparation et compositions pharmaceutiques les contenant
US4339583A (en)	1982-07-13	(Imidazolylmethyl)pyridine compounds as thromboxane synthetase inhibitors
GB2041363A (en)	1980-09-10	N-Benzyl-imidazoles
NL7906148A (nl)	1980-02-19	Nieuwe imidazoolderivaten.
EP0069513B1 (fr)	1987-03-04	Inhibiteurs d'indiole de synthétase de thromboxane, procédés pour leur préparation et compositions pharmaceutiques les contenant
US4259345A (en)	1981-03-31	2-(Imidazol-1-ylmethyl)pyrroles
GB2118552A (en)	1983-11-02	Thromboxane synthetase inhibitors
GB2102795A (en)	1983-02-09	Indole derivatives
GB2101115A (en)	1983-01-12	Thromboxane synthetase inhibitors
GB2068950A (en)	1981-08-19	Pyridine Derivatives
HU205087B (en)	1992-03-30	Process for producing 2,2'-bi(1h-imidazole) derivatives
EP0359505A1 (fr)	1990-03-21	Inhibiteurs de la dopamine-bêta-hydrolase
US4761480A (en)	1988-08-02	P-toluene-sulfonyl-oxy substituted pyridines