PH26551A - (Aryl or heteroaromatic methyl)-2,2'-bi-hi-imidazoles and their use as anti-hypertensive agents - Google Patents
(Aryl or heteroaromatic methyl)-2,2'-bi-hi-imidazoles and their use as anti-hypertensive agents Download PDFInfo
- Publication number
- PH26551A PH26551A PH37306A PH37306A PH26551A PH 26551 A PH26551 A PH 26551A PH 37306 A PH37306 A PH 37306A PH 37306 A PH37306 A PH 37306A PH 26551 A PH26551 A PH 26551A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- imidazole
- substituted
- phenyl
- chloro
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title abstract description 6
- 239000002220 antihypertensive agent Substances 0.000 title description 3
- 229940030600 antihypertensive agent Drugs 0.000 title description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 15
- 206010020772 Hypertension Diseases 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- -1 amino, sulfhydryl Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- 238000010992 reflux Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical class C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NCYCYZXNIZJOKI-HWCYFHEPSA-N 13-cis-retinal Chemical compound O=C/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-HWCYFHEPSA-N 0.000 description 1
- WHYMJLPNUWFNGY-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1-[(5-methoxythiophen-3-yl)methyl]imidazole Chemical compound S1C(OC)=CC(CN2C(=NC=C2)C=2NC=CN=2)=C1 WHYMJLPNUWFNGY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920004449 Halon® Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000252067 Megalops atlanticus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical group BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- HWZOVUKQEDRKAH-UHFFFAOYSA-N carbononitridic bromide N,N-dimethylpyridin-2-amine Chemical compound BrC#N.CN(C)C1=CC=CC=N1 HWZOVUKQEDRKAH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 108700006189 dopamine beta hydroxylase deficiency Proteins 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PH39549A PH26028A (en) | 1987-07-28 | 1989-11-17 | A process for preparing (aryl or heteroaromatic methyl)-2,2'-bi-1H-imidazoles |
| PH39550A PH26027A (en) | 1987-07-28 | 1989-11-17 | A process for preparing (aryl or heteroaromatic methyl)-2,2'-bi-1H-imidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/078,352 US4839375A (en) | 1987-07-28 | 1987-07-28 | (Aryl or heteroaromatic methyl)-2,2'-bi-1H-imidazoles and their use as anti-hypertensive agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26551A true PH26551A (en) | 1992-08-19 |
Family
ID=22143494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH37306A PH26551A (en) | 1987-07-28 | 1988-07-28 | (Aryl or heteroaromatic methyl)-2,2'-bi-hi-imidazoles and their use as anti-hypertensive agents |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4839375A (hu) |
| EP (1) | EP0301456B1 (hu) |
| JP (1) | JP2750578B2 (hu) |
| KR (1) | KR970011301B1 (hu) |
| CN (1) | CN1016173B (hu) |
| AT (1) | ATE101151T1 (hu) |
| AU (1) | AU605609B2 (hu) |
| CA (1) | CA1338786C (hu) |
| DE (1) | DE3887585T2 (hu) |
| DK (1) | DK420588A (hu) |
| ES (1) | ES2063008T3 (hu) |
| FI (1) | FI883499A (hu) |
| HU (1) | HU202861B (hu) |
| IL (1) | IL87217A (hu) |
| NO (1) | NO169841C (hu) |
| NZ (1) | NZ225561A (hu) |
| PH (1) | PH26551A (hu) |
| PT (1) | PT88121B (hu) |
| ZA (1) | ZA885360B (hu) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69931837T2 (de) * | 1998-03-20 | 2006-11-09 | China Petrochemical Corp. | Hydroentschwefelung von Kohlenwasserstoffölen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1283661C (en) * | 1984-06-20 | 1991-04-30 | Franz Jansen | Imidazolides, process for their preparation and application as intermediates for the synthesis of cytotoxic conjugates |
| CA1286301C (en) * | 1985-11-25 | 1991-07-16 | Donald P. Matthews | 2,2'-bi-1h-imidazoles |
| IL82401A0 (en) * | 1986-05-06 | 1987-11-30 | Merrell Dow Pharma | Dopamine beta hydroxy-lase inhibiting imidazole derivatives and pharmaceutical compositions containing them |
-
1987
- 1987-07-28 US US07/078,352 patent/US4839375A/en not_active Expired - Lifetime
-
1988
- 1988-07-22 AU AU19765/88A patent/AU605609B2/en not_active Ceased
- 1988-07-22 ZA ZA885360A patent/ZA885360B/xx unknown
- 1988-07-22 CA CA000572886A patent/CA1338786C/en not_active Expired - Fee Related
- 1988-07-22 JP JP63181996A patent/JP2750578B2/ja not_active Expired - Fee Related
- 1988-07-25 AT AT88111954T patent/ATE101151T1/de not_active IP Right Cessation
- 1988-07-25 ES ES88111954T patent/ES2063008T3/es not_active Expired - Lifetime
- 1988-07-25 DE DE3887585T patent/DE3887585T2/de not_active Expired - Fee Related
- 1988-07-25 FI FI883499A patent/FI883499A/fi not_active Application Discontinuation
- 1988-07-25 EP EP88111954A patent/EP0301456B1/en not_active Expired - Lifetime
- 1988-07-26 NZ NZ225561A patent/NZ225561A/en unknown
- 1988-07-26 IL IL87217A patent/IL87217A/xx unknown
- 1988-07-27 KR KR1019880009455A patent/KR970011301B1/ko not_active IP Right Cessation
- 1988-07-27 DK DK420588A patent/DK420588A/da not_active Application Discontinuation
- 1988-07-27 CN CN88108463A patent/CN1016173B/zh not_active Expired
- 1988-07-27 HU HU884001A patent/HU202861B/hu not_active IP Right Cessation
- 1988-07-27 PT PT88121A patent/PT88121B/pt not_active IP Right Cessation
- 1988-07-27 NO NO883322A patent/NO169841C/no unknown
- 1988-07-28 PH PH37306A patent/PH26551A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU202861B (en) | 1991-04-29 |
| KR970011301B1 (ko) | 1997-07-09 |
| DK420588A (da) | 1989-01-29 |
| FI883499A (fi) | 1989-01-29 |
| NZ225561A (en) | 1990-12-21 |
| US4839375A (en) | 1989-06-13 |
| ZA885360B (en) | 1989-03-29 |
| HUT53900A (en) | 1990-12-28 |
| DE3887585D1 (de) | 1994-03-17 |
| EP0301456A2 (en) | 1989-02-01 |
| DK420588D0 (da) | 1988-07-27 |
| NO883322D0 (no) | 1988-07-27 |
| ATE101151T1 (de) | 1994-02-15 |
| IL87217A0 (en) | 1988-12-30 |
| FI883499A0 (fi) | 1988-07-25 |
| PT88121B (pt) | 1995-03-01 |
| NO169841C (no) | 1992-08-12 |
| AU1976588A (en) | 1989-02-02 |
| KR890002112A (ko) | 1989-04-08 |
| NO169841B (no) | 1992-05-04 |
| ES2063008T3 (es) | 1995-01-01 |
| JPS6440465A (en) | 1989-02-10 |
| EP0301456B1 (en) | 1994-02-02 |
| CN1016173B (zh) | 1992-04-08 |
| IL87217A (en) | 1992-07-15 |
| JP2750578B2 (ja) | 1998-05-13 |
| DE3887585T2 (de) | 1994-05-26 |
| CN1034718A (zh) | 1989-08-16 |
| NO883322L (no) | 1989-01-30 |
| PT88121A (pt) | 1989-07-31 |
| AU605609B2 (en) | 1991-01-17 |
| EP0301456A3 (en) | 1990-12-05 |
| CA1338786C (en) | 1996-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1194144B1 (en) | Antibacterial compounds | |
| FI66000B (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva 2-amino-4-pyrimidonderivat | |
| CZ327195A3 (en) | Substituted 1h-imidazoles | |
| HU198300B (en) | Process for producing 2-/n-substituted guanidino/-4-heteroaryl-triazol derivatives | |
| AU597239B2 (en) | Derivatives of imidazole, their preparation and utilisation, and pharmaceutical compositions containing these derivatives | |
| HU196597B (en) | Process for producing benzimidazole derivatives, imidazo/4,5-b/pyridine derivatives and pharmaceutics comprising such compounds | |
| EP0496692A1 (en) | 2-Methoxyphenylpiperazine derivatives | |
| US5807878A (en) | Tetrasubstituted imidazoles | |
| KR20130141570A (ko) | 2-실릴옥시-피롤을 사용한 3-((피롤-2-일)메틸렌)-2-피롤론의 제조 방법 | |
| IE52822B1 (en) | Imidazole derivatives, processes for their manufacture and pharmaceutical preparations containing them | |
| JPS6343390B2 (hu) | ||
| US4882343A (en) | Biarylalkylimidazole derivatives as anti-depressants | |
| PH26551A (en) | (Aryl or heteroaromatic methyl)-2,2'-bi-hi-imidazoles and their use as anti-hypertensive agents | |
| JPH02178263A (ja) | アザアズレン誘導体、その製造法およびそれを有効成分とする抗アレルギー剤および抗炎症剤 | |
| CA2423259A1 (fr) | Nouveaux composes derives de la quinazoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| DE69805974T2 (de) | 5-aroylnaphthalin derivate | |
| JP2001139549A5 (hu) | ||
| US5017591A (en) | Thiazolyl methyl)-2-2'-Bi-1H-imidazoles and use as hypertensive agents | |
| US4929744A (en) | Process for preparing heteroaromatic methyl)-2,2'-bi-1H-imidazoles | |
| JPH01308275A (ja) | チオホルムアミド誘導体 | |
| US5932741A (en) | Imidazole-5-carboxylic acid compounds | |
| US5811444A (en) | Compositions for reducing abnormal stimulation of endothelin receptors and novel compounds | |
| EP0260814B1 (en) | Dopamine-beta-hydroxylase inhibitors | |
| HU196591B (en) | Process for producing 4-(phenylpropyl)indole derivatives and pharmaceutics comprising these compounds as active ingredient | |
| PH26027A (en) | A process for preparing (aryl or heteroaromatic methyl)-2,2'-bi-1H-imidazoles |