IL136303A

IL136303A - History -5 (-2 Imidazolinylamino) - Banimidazole, preparation and use as an α-adororeceptor agonists

History -5 (-2 Imidazolinylamino) - Banimidazole, preparation and use as an α-adororeceptor agonists

Info

Publication number: IL136303A
Authority: IL; Israel
Prior art keywords: methyl; hydrogen; dosage range; cyano; compound
Prior art date: 1997-11-24

Application number

IL13630398A

Other languages

English (en)

Hebrew (he)

Other versions

IL136303A0 (en

Original Assignee

Procter & Gamble

Priority date

1997-11-24

Filing date

1998-11-20

Publication date

2004-02-08

1998-11-20 Application filed by Procter & Gamble filed Critical Procter & Gamble

2001-05-20 Publication of IL136303A0 publication Critical patent/IL136303A0/xx

2004-02-08 Publication of IL136303A publication Critical patent/IL136303A/en

Links

239000000556 agonist Substances 0.000 title description 17
238000002360 preparation method Methods 0.000 title description 5
102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 title description 3
108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 title description 3
JYQSIEABODGLIB-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)-3h-benzimidazol-5-amine Chemical class C1=NCCN1NC1=CC=C(N=CN2)C2=C1 JYQSIEABODGLIB-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 143
239000001257 hydrogen Substances 0.000 claims abstract description 40
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 40
150000003839 salts Chemical class 0.000 claims abstract description 32
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
150000002431 hydrogen Chemical class 0.000 claims abstract description 24
-1 amino, methoxy, hydroxy Chemical group 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 8
150000001408 amides Chemical class 0.000 claims abstract description 6
150000002148 esters Chemical class 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000011737 fluorine Substances 0.000 claims abstract description 4
150000003949 imides Chemical class 0.000 claims abstract description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
125000001475 halogen functional group Chemical group 0.000 claims abstract 10
239000003937 drug carrier Substances 0.000 claims description 11
239000005557 antagonist Substances 0.000 claims description 7
239000003963 antioxidant agent Substances 0.000 claims description 6
DIVZRPNDDCBSDJ-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)-4-ethyl-7-methyl-3h-benzimidazol-5-amine Chemical compound C1=C(C)C=2N=CNC=2C(CC)=C1NN1CCN=C1 DIVZRPNDDCBSDJ-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000003381 stabilizer Substances 0.000 claims description 5
OJYPWPGSEHJUOX-UHFFFAOYSA-N 4-cyclopropyl-n-(4,5-dihydroimidazol-1-yl)-7-methyl-3h-benzimidazol-5-amine Chemical compound C1CC1C=1C=2NC=NC=2C(C)=CC=1NN1CCN=C1 OJYPWPGSEHJUOX-UHFFFAOYSA-N 0.000 claims description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 3
239000003172 expectorant agent Substances 0.000 claims description 3
230000002496 gastric effect Effects 0.000 claims description 3
210000003630 histaminocyte Anatomy 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
VSXUCCMXRHBFMW-UHFFFAOYSA-N 6-(4,5-dihydroimidazol-1-ylamino)-7-methyl-3h-benzimidazol-4-ol Chemical compound C1=C(O)C=2NC=NC=2C(C)=C1NN1CCN=C1 VSXUCCMXRHBFMW-UHFFFAOYSA-N 0.000 claims description 2
NLZOTYQRHYTOFD-UHFFFAOYSA-N 6-(4,5-dihydroimidazol-1-ylamino)-7-methyl-3h-benzimidazole-4-carbonitrile Chemical compound C1=C(C#N)C=2NC=NC=2C(C)=C1NN1CCN=C1 NLZOTYQRHYTOFD-UHFFFAOYSA-N 0.000 claims description 2
230000000954 anitussive effect Effects 0.000 claims description 2
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230000001387 anti-histamine Effects 0.000 claims 1
230000000840 anti-viral effect Effects 0.000 claims 1
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PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 138
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
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125000005843 halogen group Chemical group 0.000 description 14
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 description 12
108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 12
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239000002253 acid Substances 0.000 description 11
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
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CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 7
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125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
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