IL96879A - 4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing it - Google Patents

4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing it

Info

Publication number: IL96879A
Authority: IL; Israel
Prior art keywords: water; hemihydrate; formula; pyridin; hydrochloride
Prior art date: 1990-01-12

Application number

IL9687991A

Other languages

English (en)

Other versions

IL96879A0 (en

Original Assignee

Ciba Geigy Ag

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.)

1990-01-12

Filing date

1991-01-04

Publication date

1995-06-29

1991-01-04 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1992-03-29 Publication of IL96879A0 publication Critical patent/IL96879A0/xx

1995-06-29 Publication of IL96879A publication Critical patent/IL96879A/en

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 title description 4
AYOZOVVTFYCBNM-UHFFFAOYSA-N 4-(1,2,3,5-tetrahydroimidazo[1,5-a]pyridin-1-yl)benzonitrile hydrochloride Chemical compound Cl.C1(NCN2C1=CC=CC2)C2=CC=C(C#N)C=C2 AYOZOVVTFYCBNM-UHFFFAOYSA-N 0.000 title 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 32
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 25
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims abstract description 18
239000000825 pharmaceutical preparation Substances 0.000 claims description 12
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims description 10
239000000843 powder Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
102000014654 Aromatase Human genes 0.000 claims description 3
108010078554 Aromatase Proteins 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
238000004279 X-ray Guinier Methods 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000005764 inhibitory process Effects 0.000 claims description 2
230000005855 radiation Effects 0.000 claims description 2
102100035863 E3 SUMO-protein ligase ZNF451 Human genes 0.000 claims 1
101000782473 Homo sapiens E3 SUMO-protein ligase ZNF451 Proteins 0.000 claims 1
238000002425 crystallisation Methods 0.000 abstract description 5
238000003860 storage Methods 0.000 abstract description 5
230000008025 crystallization Effects 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
239000013078 crystal Substances 0.000 description 20
239000004480 active ingredient Substances 0.000 description 15
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 9
230000004048 modification Effects 0.000 description 8
238000012986 modification Methods 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
239000000262 estrogen Substances 0.000 description 6
239000012458 free base Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
230000001419 dependent effect Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
229920002472 Starch Polymers 0.000 description 4
239000002775 capsule Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000007787 solid Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
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 3
239000003125 aqueous solvent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000008119 colloidal silica Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
239000008298 dragée Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000011085 pressure filtration Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000002511 suppository base Substances 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
RBNOZCGLHXZRLF-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1.C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 RBNOZCGLHXZRLF-UHFFFAOYSA-N 0.000 description 1
ZVZKQUVPVSHUPY-UHFFFAOYSA-N 4-[1-chloro-4-(1h-imidazol-5-yl)butyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(Cl)CCCC1=CNC=N1 ZVZKQUVPVSHUPY-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
CCLDINJQFZRBPY-UHFFFAOYSA-N Cl.N1=C(C=CC=C1)C1=CC=CC=C1C#N Chemical compound Cl.N1=C(C=CC=C1)C1=CC=CC=C1C#N CCLDINJQFZRBPY-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 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
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000003795 desorption Methods 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
201000000079 gynecomastia Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical class C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000010453 quartz Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
-1 starches Chemical compound 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
CNQDVAWRPXCHEG-UHFFFAOYSA-K trilithium;trichloride Chemical compound [Li+].[Li+].[Li+].[Cl-].[Cl-].[Cl-] CNQDVAWRPXCHEG-UHFFFAOYSA-K 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)
Lubricants (AREA)
Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
Pyridine Compounds (AREA)
Photoreceptors In Electrophotography (AREA)
Liquid Crystal Substances (AREA)

IL9687991A 1990-01-12 1991-01-04 4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing it IL96879A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH10090		1990-01-12

Publications (2)

Publication Number	Publication Date
IL96879A0 IL96879A0 (en)	1992-03-29
IL96879A true IL96879A (en)	1995-06-29

Family

ID=4179261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9687991A IL96879A (en)	1990-01-12	1991-01-04	4-tetrahydroimidazo [1,5-a] pyridinyl benzonitrile hydrochloride process for its preparation and pharmaceutical compositions containing it

Country Status (32)

Country	Link
US (1)	US5098911A (fr)
EP (1)	EP0437415B1 (fr)
JP (1)	JP2694186B2 (fr)
KR (1)	KR100191360B1 (fr)
CN (1)	CN1037966C (fr)
AT (1)	ATE125809T1 (fr)
AU (1)	AU638085B2 (fr)
BG (2)	BG60033B2 (fr)
CA (1)	CA2033937C (fr)
CZ (1)	CZ279823B6 (fr)
DE (1)	DE59106101D1 (fr)
DK (1)	DK0437415T3 (fr)
DZ (1)	DZ1482A1 (fr)
ES (1)	ES2075399T3 (fr)
FI (1)	FI94528C (fr)
GR (1)	GR3017027T3 (fr)
HU (1)	HU216192B (fr)
ID (1)	ID964B (fr)
IE (1)	IE67512B1 (fr)
IL (1)	IL96879A (fr)
MA (1)	MA22040A1 (fr)
MT (1)	MTP1076B (fr)
NO (1)	NO175747C (fr)
NZ (1)	NZ236735A (fr)
PH (1)	PH27601A (fr)
PL (3)	PL166500B1 (fr)
PT (1)	PT96447B (fr)
RO (1)	RO107408B1 (fr)
RU (2)	RU2021271C1 (fr)
SA (1)	SA93140021B1 (fr)
TN (1)	TNSN91001A1 (fr)
ZA (1)	ZA91229B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW208013B (fr) *	1990-03-01	1993-06-21	Daiichi Co Ltd
EP0457716A1 (fr) *	1990-04-20	1991-11-21	Ciba-Geigy Ag	Dérivés de naphtaline
TW224461B (fr) *	1990-09-18	1994-06-01	Ciba Geigy Ag
CH683151A5 (de) *	1991-04-24	1994-01-31	Ciba Geigy Ag	Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus.
JP2914324B2 (ja) *	1995-10-23	1999-06-28	味の素株式会社	ピペリジン誘導体の結晶並びにその製造中間体及び製造方法
SE9902550D0 (sv) *	1999-07-02	1999-07-02	Astra Ab	New crystalline forms
KR20180118801A (ko)	2010-09-01	2018-10-31	에자이 알앤드디 매니지먼트 가부시키가이샤	체중 관리에 유용한 5-ｈｔ2ｃ 작동제의 변형-방출 투여 형태
EA201390335A1 (ru)	2010-09-01	2013-09-30	Арена Фармасьютикалз, Инк.	Введение лоркасерина индивидуумам с почечной недостаточностью
AU2013209952B2 (en) *	2012-01-17	2016-09-01	Recordati Ag	New forms and salts of a dihydropyrrolo(1,2-c)imidazolyl aldosterone synthase or aromatase inhibitor
SG11201903803UA (en)	2016-10-27	2019-05-30	Damian Pharma Ag	Aldosterone synthase inhibitor
WO2018078049A1 (fr)	2016-10-27	2018-05-03	Damian Pharma Ag	Inhibiteur de l'aldostérone synthase
WO2019211394A1 (fr)	2018-05-03	2019-11-07	Damian Pharma Ag	R-fadrozole destiné à être utilisé dans le traitement de l'aldostéronisme

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4588732A (en) *	1982-12-21	1986-05-13	Ciba-Geigy Corporation	Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane synthetase inhibitors
US4617307A (en) *	1984-06-20	1986-10-14	Ciba-Geigy Corporation	Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors

1990
- 1990-12-14 MT MT1076A patent/MTP1076B/xx unknown
1991
- 1991-01-02 US US07/636,816 patent/US5098911A/en not_active Expired - Lifetime
- 1991-01-02 PH PH41805A patent/PH27601A/en unknown
- 1991-01-03 ES ES91810003T patent/ES2075399T3/es not_active Expired - Lifetime
- 1991-01-03 EP EP91810003A patent/EP0437415B1/fr not_active Expired - Lifetime
- 1991-01-03 DE DE59106101T patent/DE59106101D1/de not_active Expired - Lifetime
- 1991-01-03 DK DK91810003.3T patent/DK0437415T3/da active
- 1991-01-03 AT AT91810003T patent/ATE125809T1/de not_active IP Right Cessation
- 1991-01-04 IL IL9687991A patent/IL96879A/en not_active IP Right Cessation
- 1991-01-07 MA MA22312A patent/MA22040A1/fr unknown
- 1991-01-09 DZ DZ910008A patent/DZ1482A1/fr active
- 1991-01-09 FI FI910126A patent/FI94528C/fi active
- 1991-01-10 PL PL91304087A patent/PL166500B1/pl unknown
- 1991-01-10 PL PL91288653A patent/PL166157B1/pl unknown
- 1991-01-10 PT PT96447A patent/PT96447B/pt not_active IP Right Cessation
- 1991-01-10 AU AU69280/91A patent/AU638085B2/en not_active Expired
- 1991-01-10 CA CA002033937A patent/CA2033937C/fr not_active Expired - Lifetime
- 1991-01-10 PL PL91304084A patent/PL167164B1/pl unknown
- 1991-01-10 NZ NZ236735A patent/NZ236735A/xx unknown
- 1991-01-10 RO RO146713A patent/RO107408B1/ro unknown
- 1991-01-10 KR KR1019910000244A patent/KR100191360B1/ko not_active Expired - Lifetime
- 1991-01-11 HU HU4/91A patent/HU216192B/hu unknown
- 1991-01-11 IE IE10391A patent/IE67512B1/en not_active IP Right Cessation
- 1991-01-11 CN CN91101118A patent/CN1037966C/zh not_active Expired - Lifetime
- 1991-01-11 RU SU914894233A patent/RU2021271C1/ru active
- 1991-01-11 CZ CS9155A patent/CZ279823B6/cs not_active IP Right Cessation
- 1991-01-11 JP JP3065711A patent/JP2694186B2/ja not_active Expired - Lifetime
- 1991-01-11 NO NO910137A patent/NO175747C/no not_active IP Right Cessation
- 1991-01-11 ZA ZA91229A patent/ZA91229B/xx unknown
- 1991-01-11 TN TNTNSN91001A patent/TNSN91001A1/fr unknown
- 1991-01-14 BG BG093623A patent/BG60033B2/xx unknown
1992
- 1992-01-30 ID IDP190792A patent/ID964B/id unknown
- 1992-04-07 RU SU925011257A patent/RU2088584C1/ru active
- 1992-08-18 BG BG096793A patent/BG61489B2/bg unknown
1993
- 1993-06-29 SA SA93140021A patent/SA93140021B1/ar unknown
1995
- 1995-08-03 GR GR950401945T patent/GR3017027T3/el unknown

Also Published As

Publication number	Publication date
CN1055739A (zh)	1991-10-30
ATE125809T1 (de)	1995-08-15
RU2021271C1 (ru)	1994-10-15
JPH04210982A (ja)	1992-08-03
GR3017027T3 (en)	1995-11-30
ES2075399T3 (es)	1995-10-01
IE67512B1 (en)	1996-04-03
HUT56568A (en)	1991-09-30
DK0437415T3 (da)	1995-09-18
FI910126A0 (fi)	1991-01-09
EP0437415A2 (fr)	1991-07-17
MTP1076B (en)	1991-09-30
EP0437415B1 (fr)	1995-08-02
JP2694186B2 (ja)	1997-12-24
CA2033937A1 (fr)	1991-07-13
CZ279823B6 (cs)	1995-07-12
FI910126L (fi)	1991-07-13
NO175747B (no)	1994-08-22
KR100191360B1 (ko)	1999-06-15
FI94528C (fi)	1995-09-25
ZA91229B (en)	1991-08-28
PT96447A (pt)	1991-10-15
HU910084D0 (en)	1991-08-28
AU6928091A (en)	1991-07-18
US5098911A (en)	1992-03-24
NO910137D0 (no)	1991-01-11
PH27601A (en)	1993-08-31
BG60033B2 (en)	1993-07-15
CS9100055A2 (en)	1991-08-13
MA22040A1 (fr)	1991-10-01
RU2088584C1 (ru)	1997-08-27
FI94528B (fi)	1995-06-15
PL166157B1 (pl)	1995-04-28
PL167164B1 (pl)	1995-08-31
CN1037966C (zh)	1998-04-08
HK1000663A1 (en)	1998-04-17
CA2033937C (fr)	2001-03-13
ID964B (id)	1996-09-30
IL96879A0 (en)	1992-03-29
EP0437415A3 (en)	1992-01-22
AU638085B2 (en)	1993-06-17
DE59106101D1 (de)	1995-09-07
KR910014376A (ko)	1991-08-31
PL288653A1 (en)	1991-12-16
PL166500B1 (pl)	1995-05-31
DZ1482A1 (fr)	2004-09-13
NO910137L (no)	1991-07-15
RO107408B1 (ro)	1993-11-30
PT96447B (pt)	1998-09-30
HU216192B (en)	2001-03-28
TNSN91001A1 (en)	1992-10-25
BG61489B2 (bg)	1997-09-30
NO175747C (no)	1994-11-30
IE910103A1 (en)	1991-07-17
NZ236735A (en)	1992-10-28
SA93140021B1 (ar)	2006-07-11

Legal Events

Date	Code	Title
1997-04-15	KB	Patent renewed
2001-06-14	KB	Patent renewed
2009-07-20	KB	Patent renewed
2011-09-27	EXP	Patent expired

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