DD299301A5 - Biphenylmethanderivate sowie dessen pharmakologische verwendung - Google Patents

Biphenylmethanderivate sowie dessen pharmakologische verwendung Download PDF

Info

Publication number: DD299301A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; pyridine; imidazo; tetrazol; nmr
Prior art date: 1989-09-29

Application number

DD90344302A

Other languages

German (de)

English (en)

Inventor

Kazutoshi Miyake

Masayuki Masukura

Naoki Yoneda

Osamu Hiroshima

Nobuyuki Mori

Hiroki Ishihara

Takashi Musha

Toshiyuki Matsuoka

Sachiyuki Hamano

Norio Minami

Original Assignee

��@�K@�Kk��

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.)

1989-09-29

Filing date

1990-09-28

Publication date

1992-04-09

1990-09-28 Application filed by ��@�K@�Kk�� filed Critical ��@�K@�Kk��

1992-04-09 Publication of DD299301A5 publication Critical patent/DD299301A5/de

Links

ZWZGXLKXKAPXMZ-UHFFFAOYSA-N 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dipropyldiphenylmethane Chemical class COC1=CC(CCC)=CC(CC=2C(=C(OC)C=C(CCC)C=2)O)=C1O ZWZGXLKXKAPXMZ-UHFFFAOYSA-N 0.000 title claims abstract description 22
230000000144 pharmacologic effect Effects 0.000 title claims description 7
-1 1H-tetrazol-5-yl Chemical group 0.000 claims abstract description 104
150000001875 compounds Chemical class 0.000 claims abstract description 89
125000000217 alkyl group Chemical group 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 40
238000002360 preparation method Methods 0.000 claims abstract description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
206010020772 Hypertension Diseases 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
206010019280 Heart failures Diseases 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
230000002265 prevention Effects 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 99
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
239000002904 solvent Substances 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 22
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 12
239000012312 sodium hydride Substances 0.000 claims description 12
229910000104 sodium hydride Inorganic materials 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
239000012046 mixed solvent Substances 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 5
229910000103 lithium hydride Inorganic materials 0.000 claims description 5
125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
150000002460 imidazoles Chemical class 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
CUUHDAVVGGQJQH-UHFFFAOYSA-N 2-[4-[(2-ethoxy-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CCOC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O CUUHDAVVGGQJQH-UHFFFAOYSA-N 0.000 claims description 2
SBFMLSFMTZOOLF-UHFFFAOYSA-N 5,7-dimethyl-2-propoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCOC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 SBFMLSFMTZOOLF-UHFFFAOYSA-N 0.000 claims description 2
239000008196 pharmacological composition Substances 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims 4
MFQQQYHMVLSONB-UHFFFAOYSA-N 2-[4-[(2-cyclopropyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound C=1C=C(C=2C(=CC=CC=2)C(O)=O)C=CC=1CN1C2=NC(C)=CC(C)=C2N=C1C1CC1 MFQQQYHMVLSONB-UHFFFAOYSA-N 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
150000002431 hydrogen Chemical group 0.000 abstract 4
102100036301 C-C chemokine receptor type 7 Human genes 0.000 abstract 1
101000716065 Homo sapiens C-C chemokine receptor type 7 Proteins 0.000 abstract 1
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
239000000203 mixture Substances 0.000 description 57
238000002844 melting Methods 0.000 description 50
230000008018 melting Effects 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 29
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
239000000126 substance Substances 0.000 description 20
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
238000012360 testing method Methods 0.000 description 11
239000000460 chlorine Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
239000007858 starting material Substances 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 7
102000005862 Angiotensin II Human genes 0.000 description 7
101800000733 Angiotensin-2 Proteins 0.000 description 7
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 7
229950006323 angiotensin ii Drugs 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
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 5
241000700159 Rattus Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000036772 blood pressure Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
229940123413 Angiotensin II antagonist Drugs 0.000 description 4
206010062575 Muscle contracture Diseases 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
239000002333 angiotensin II receptor antagonist Substances 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
208000006111 contracture Diseases 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
230000001631 hypertensive effect Effects 0.000 description 4
238000005191 phase separation Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 3
APGDUAJEMRMIJU-UHFFFAOYSA-N 4-chloropyridine-2,3-diamine Chemical compound NC1=NC=CC(Cl)=C1N APGDUAJEMRMIJU-UHFFFAOYSA-N 0.000 description 3
ROGACPLRFHTHNR-UHFFFAOYSA-N 7-chloro-2-propyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CN=C2NC(CCC)=NC2=C1Cl ROGACPLRFHTHNR-UHFFFAOYSA-N 0.000 description 3
XIMLLORHEQZHGS-UHFFFAOYSA-N 7-methyl-1,3-dihydroimidazo[4,5-b]pyridine-2-thione Chemical compound CC1=CC=NC2=C1N=C(S)N2 XIMLLORHEQZHGS-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
RMXGTMRDXKUUDJ-UHFFFAOYSA-N methyl 2-[4-(bromomethyl)phenyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=C(CBr)C=C1 RMXGTMRDXKUUDJ-UHFFFAOYSA-N 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000004044 response Effects 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
ZOABJVUIICYNPX-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C)(C)CO1 ZOABJVUIICYNPX-UHFFFAOYSA-N 0.000 description 2
ZLBZJTWLYCGFSO-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]-4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(C=2C=CC(CBr)=CC=2)=C1 ZLBZJTWLYCGFSO-UHFFFAOYSA-N 0.000 description 2
LFFIEVAMVPCZNA-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]benzonitrile Chemical compound C1=CC(CBr)=CC=C1C1=CC=CC=C1C#N LFFIEVAMVPCZNA-UHFFFAOYSA-N 0.000 description 2
JPXYIJHKHAKKFZ-UHFFFAOYSA-N 2-[4-[(2-butylbenzimidazol-1-yl)methyl]phenyl]-4-chlorobenzonitrile Chemical compound CCCCC1=NC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC(Cl)=CC=C1C#N JPXYIJHKHAKKFZ-UHFFFAOYSA-N 0.000 description 2
BTCSTTFEDNVJAW-UHFFFAOYSA-N 2-cyclopropyl-7-methyl-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(C)=CC=NC=2NC=1C1CC1 BTCSTTFEDNVJAW-UHFFFAOYSA-N 0.000 description 2
QWUJQZPRHRBFOE-UHFFFAOYSA-N 2-ethylsulfonyl-7-methyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCS(=O)(=O)C1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 QWUJQZPRHRBFOE-UHFFFAOYSA-N 0.000 description 2
AHYFQMPJAPLWIH-UHFFFAOYSA-N 4-chloro-2-(4-methylphenyl)benzonitrile Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=CC=C1C#N AHYFQMPJAPLWIH-UHFFFAOYSA-N 0.000 description 2
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
RWGGFJXJRPCCGD-UHFFFAOYSA-N 4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(N)=C1N RWGGFJXJRPCCGD-UHFFFAOYSA-N 0.000 description 2
CGGOAYCJQTWSOI-UHFFFAOYSA-N 4-propylpyridin-2-amine Chemical compound CCCC1=CC=NC(N)=C1 CGGOAYCJQTWSOI-UHFFFAOYSA-N 0.000 description 2
QLUQKHWXZSHTAD-UHFFFAOYSA-N 4-propylpyridine-2,3-diamine Chemical compound CCCC1=CC=NC(N)=C1N QLUQKHWXZSHTAD-UHFFFAOYSA-N 0.000 description 2
OZLCYNBIDVJEEN-UHFFFAOYSA-N 7-methyl-2-methylsulfanyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CN=C2NC(SC)=NC2=C1C OZLCYNBIDVJEEN-UHFFFAOYSA-N 0.000 description 2
ADNBACOBZBXVSJ-UHFFFAOYSA-N 7-methyl-2-propoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCOC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 ADNBACOBZBXVSJ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
239000005541 ACE inhibitor Substances 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
102000015427 Angiotensins Human genes 0.000 description 2
108010064733 Angiotensins Proteins 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
239000002876 beta blocker Substances 0.000 description 2
229940097320 beta blocking agent Drugs 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000000576 coating method Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
229920001249 ethyl cellulose Polymers 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
210000000609 ganglia Anatomy 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
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 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
229960002275 pentobarbital sodium Drugs 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
238000012453 sprague-dawley rat model Methods 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
125000003831 tetrazolyl group Chemical group 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
YCFJXOFFQLPCHD-UHFFFAOYSA-N (S)-Spinacine Chemical class C1NC(C(=O)O)CC2=C1NC=N2 YCFJXOFFQLPCHD-UHFFFAOYSA-N 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
ZSTUEICKYWFYIC-UHFFFAOYSA-N 2-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(O)=O ZSTUEICKYWFYIC-UHFFFAOYSA-N 0.000 description 1
HITWHALOZBMLHY-UHFFFAOYSA-N 2-Butyl-1H-benzimidazole Chemical compound C1=CC=C2NC(CCCC)=NC2=C1 HITWHALOZBMLHY-UHFFFAOYSA-N 0.000 description 1
SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-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)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
MVLPZTKABOBMET-UHFFFAOYSA-N 2-[4-[(2-butyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O MVLPZTKABOBMET-UHFFFAOYSA-N 0.000 description 1
TVNBFJNQCWCHHE-UHFFFAOYSA-N 2-[4-[(2-butylbenzimidazol-1-yl)methyl]phenyl]benzoic acid Chemical compound CCCCC1=NC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O TVNBFJNQCWCHHE-UHFFFAOYSA-N 0.000 description 1
FCAYSPSSISKEHH-UHFFFAOYSA-N 2-[4-[(2-butylimidazo[4,5-c]pyridin-1-yl)methyl]phenyl]benzonitrile Chemical compound CCCCC1=NC2=CN=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C#N FCAYSPSSISKEHH-UHFFFAOYSA-N 0.000 description 1
NWJAMBOMQUEYLH-UHFFFAOYSA-N 2-[4-[(2-cyclobutyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound C1CCC1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O NWJAMBOMQUEYLH-UHFFFAOYSA-N 0.000 description 1
VWWMGPCUZVOLLK-UHFFFAOYSA-N 2-[4-[(2-cyclopropyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound C1CC1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O VWWMGPCUZVOLLK-UHFFFAOYSA-N 0.000 description 1
YPMHIQSAWQKUIK-UHFFFAOYSA-N 2-[4-[(2-ethyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzonitrile Chemical compound CCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C#N YPMHIQSAWQKUIK-UHFFFAOYSA-N 0.000 description 1
KJYZSCFPYRKZFA-UHFFFAOYSA-N 2-[4-[(2-ethylimidazo[4,5-b]pyridin-1-yl)methyl]phenyl]benzonitrile Chemical compound CCC1=NC2=NC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C#N KJYZSCFPYRKZFA-UHFFFAOYSA-N 0.000 description 1
WAWHIAROQWDEGD-UHFFFAOYSA-N 2-[4-[(2-ethylimidazo[4,5-b]pyridin-4-yl)methyl]phenyl]benzonitrile Chemical compound C12=NC(CC)=NC2=CC=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C#N WAWHIAROQWDEGD-UHFFFAOYSA-N 0.000 description 1
OPQSNPPFWPEOSF-UHFFFAOYSA-N 2-[4-[(2-ethylsulfanyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CCSC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O OPQSNPPFWPEOSF-UHFFFAOYSA-N 0.000 description 1
ZCRUQLBXHMYLTP-UHFFFAOYSA-N 2-[4-[(2-methoxy-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound COC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O ZCRUQLBXHMYLTP-UHFFFAOYSA-N 0.000 description 1
GPPOOYHLJNQSEU-UHFFFAOYSA-N 2-[4-[(5,7-dimethyl-2-propoxyimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CCCOC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O GPPOOYHLJNQSEU-UHFFFAOYSA-N 0.000 description 1
XWMKQOHPRXGELP-UHFFFAOYSA-N 2-[4-[(7-chloro-2-propylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CCCC1=NC2=C(Cl)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O XWMKQOHPRXGELP-UHFFFAOYSA-N 0.000 description 1
LTCKFDSBVGOGKB-UHFFFAOYSA-N 2-[4-[(7-methyl-2-methylsulfanylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CSC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O LTCKFDSBVGOGKB-UHFFFAOYSA-N 0.000 description 1
LPEUCKPUPISWMA-UHFFFAOYSA-N 2-[4-[(7-methyl-2-prop-1-enylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CC=CC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O LPEUCKPUPISWMA-UHFFFAOYSA-N 0.000 description 1
SLALIOOTEWEYCC-UHFFFAOYSA-N 2-[4-[(7-methyl-2-propan-2-ylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CC(C)C1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O SLALIOOTEWEYCC-UHFFFAOYSA-N 0.000 description 1
KZNHQXXPROIGDV-UHFFFAOYSA-N 2-[4-[(7-methyl-2-propylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O KZNHQXXPROIGDV-UHFFFAOYSA-N 0.000 description 1
GSEGNXPJKIHSPZ-UHFFFAOYSA-N 2-[4-[[7-(methoxymethyl)-7-methyl-2h-imidazo[4,5-b]pyridin-3-yl]methyl]phenyl]benzoic acid Chemical compound C1N=C2C(COC)(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O GSEGNXPJKIHSPZ-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
KFIGMIZXWBBYDN-UHFFFAOYSA-N 2-butoxy-7-methyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCCOC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 KFIGMIZXWBBYDN-UHFFFAOYSA-N 0.000 description 1
VAWPYIMZXLZBOG-UHFFFAOYSA-N 2-butyl-1-[[4-[4-chloro-2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole Chemical compound CCCCC1=NC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=C(Cl)C=C1C1=NN=NN1 VAWPYIMZXLZBOG-UHFFFAOYSA-N 0.000 description 1
YILJWHUIUCRKEU-UHFFFAOYSA-N 2-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=CC=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 YILJWHUIUCRKEU-UHFFFAOYSA-N 0.000 description 1
KVWWLDGBSOCRJL-UHFFFAOYSA-N 2-butyl-3h-imidazo[4,5-c]pyridine Chemical compound N1=CC=C2NC(CCCC)=NC2=C1 KVWWLDGBSOCRJL-UHFFFAOYSA-N 0.000 description 1
WWRPMKVRPHIVTL-UHFFFAOYSA-N 2-ethoxy-1h-imidazo[4,5-b]pyridine Chemical compound C1=CN=C2NC(OCC)=NC2=C1 WWRPMKVRPHIVTL-UHFFFAOYSA-N 0.000 description 1
GERUDNMWFKFUPR-UHFFFAOYSA-N 2-ethyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CN=C2NC(CC)=NC2=C1 GERUDNMWFKFUPR-UHFFFAOYSA-N 0.000 description 1
FDJIEFOFGKLNEK-UHFFFAOYSA-N 2-ethyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCC1=NC2=CC=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 FDJIEFOFGKLNEK-UHFFFAOYSA-N 0.000 description 1
JWTDOQFMPHKFDW-UHFFFAOYSA-N 2-ethyl-7-methyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 JWTDOQFMPHKFDW-UHFFFAOYSA-N 0.000 description 1
OCPONDWJUPBVAZ-UHFFFAOYSA-N 2-ethyl-7-propyl-1h-imidazo[4,5-b]pyridine Chemical compound CCCC1=CC=NC2=C1NC(CC)=N2 OCPONDWJUPBVAZ-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
YJNOVRLKCGGGQI-UHFFFAOYSA-N 2-ethylsulfanyl-7-methyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCSC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 YJNOVRLKCGGGQI-UHFFFAOYSA-N 0.000 description 1
YJHLFBLJKIVUGI-UHFFFAOYSA-N 2-methoxy-5,7-dimethyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound COC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 YJHLFBLJKIVUGI-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
SJVXKCIZKOOBOK-UHFFFAOYSA-N 2-pentyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCCCC1=NC2=CC=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 SJVXKCIZKOOBOK-UHFFFAOYSA-N 0.000 description 1
FZIAKTKGPHNJCW-UHFFFAOYSA-N 2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=CC=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 FZIAKTKGPHNJCW-UHFFFAOYSA-N 0.000 description 1
QINUKWGKRXXSFL-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=CC=CN=C2N1CC(C=C1)=CC=C1C1=CC=C(Cl)C=C1C=1N=NNN=1 QINUKWGKRXXSFL-UHFFFAOYSA-N 0.000 description 1
JFDSNFSZTQCLJF-UHFFFAOYSA-N 3-[[4-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=CC=CN=C2N1CC(C=C1)=CC=C1C1=CC(Cl)=CC=C1C1=NN=NN1 JFDSNFSZTQCLJF-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
QEUSIWJLEVXXSP-UHFFFAOYSA-N 3-methoxy-2-(4-methylphenyl)benzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1C1=CC=C(C)C=C1 QEUSIWJLEVXXSP-UHFFFAOYSA-N 0.000 description 1
PSFBXBCSEQSBFP-UHFFFAOYSA-N 3-methoxy-2-(4-methylphenyl)benzonitrile Chemical compound COC1=CC=CC(C#N)=C1C1=CC=C(C)C=C1 PSFBXBCSEQSBFP-UHFFFAOYSA-N 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
QCPJSMXCDJNLDW-UHFFFAOYSA-N 3-nitro-4-propylpyridin-2-amine Chemical compound CCCC1=CC=NC(N)=C1[N+]([O-])=O QCPJSMXCDJNLDW-UHFFFAOYSA-N 0.000 description 1
HDJYVHKPMUNKFE-UHFFFAOYSA-N 4-chloro-2-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=CC=C1C(N)=O HDJYVHKPMUNKFE-UHFFFAOYSA-N 0.000 description 1
UVRIBLSFPZQTTJ-UHFFFAOYSA-N 4-chloro-2-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=CC=C1C(O)=O UVRIBLSFPZQTTJ-UHFFFAOYSA-N 0.000 description 1
UFEYMXHWIHFRBX-UHFFFAOYSA-N 4-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(Cl)=CC=C1C(O)=O UFEYMXHWIHFRBX-UHFFFAOYSA-N 0.000 description 1
OKEFBVALFLRAFV-UHFFFAOYSA-N 4-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC(Cl)=CC=C1C(Cl)=O OKEFBVALFLRAFV-UHFFFAOYSA-N 0.000 description 1
DIRINUVNYFAWQF-UHFFFAOYSA-N 4-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC=CC(Cl)=C1[N+]([O-])=O DIRINUVNYFAWQF-UHFFFAOYSA-N 0.000 description 1
YFIVCCRQVYGRDH-UHFFFAOYSA-N 4-methoxy-2-(4-methylphenyl)benzonitrile Chemical compound COC1=CC=C(C#N)C(C=2C=CC(C)=CC=2)=C1 YFIVCCRQVYGRDH-UHFFFAOYSA-N 0.000 description 1
JAWZAONCXMJLFT-UHFFFAOYSA-N 4-propylpyridine Chemical compound CCCC1=CC=NC=C1 JAWZAONCXMJLFT-UHFFFAOYSA-N 0.000 description 1
VRBPVOFTDKMURN-UHFFFAOYSA-N 5,7-dimethyl-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 VRBPVOFTDKMURN-UHFFFAOYSA-N 0.000 description 1
DUOORCZINRRBOP-UHFFFAOYSA-N 5-chloro-2-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(Cl)C=C1C(O)=O DUOORCZINRRBOP-UHFFFAOYSA-N 0.000 description 1
BPJIRTABJWUOFC-UHFFFAOYSA-N 5-chloro-2-(4-methylphenyl)benzonitrile Chemical compound C1=CC(C)=CC=C1C1=CC=C(Cl)C=C1C#N BPJIRTABJWUOFC-UHFFFAOYSA-N 0.000 description 1
TWWOEXVZOBUJTL-UHFFFAOYSA-N 5-methoxy-2-(4-methylphenyl)benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1C1=CC=C(C)C=C1 TWWOEXVZOBUJTL-UHFFFAOYSA-N 0.000 description 1
YZRMFTZGQCVRIR-UHFFFAOYSA-N 5-methoxy-2-(4-methylphenyl)benzonitrile Chemical compound N#CC1=CC(OC)=CC=C1C1=CC=C(C)C=C1 YZRMFTZGQCVRIR-UHFFFAOYSA-N 0.000 description 1
HFIWOFWWIAHZOP-UHFFFAOYSA-N 5-nitro-4-propylpyridin-2-amine Chemical compound CCCC1=CC(N)=NC=C1[N+]([O-])=O HFIWOFWWIAHZOP-UHFFFAOYSA-N 0.000 description 1
XFBSXNBXKWBPJI-UHFFFAOYSA-N 6-methyl-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=CC(C)=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 XFBSXNBXKWBPJI-UHFFFAOYSA-N 0.000 description 1
BAEHKMMWUUIOJN-UHFFFAOYSA-N 7-methyl-1h-imidazo[4,5-b]pyridine Chemical compound CC1=CC=NC2=C1NC=N2 BAEHKMMWUUIOJN-UHFFFAOYSA-N 0.000 description 1
CYUMNDVYHILLEX-UHFFFAOYSA-N 7-methyl-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 CYUMNDVYHILLEX-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
244000080208 Canella winterana Species 0.000 description 1
235000008499 Canella winterana Nutrition 0.000 description 1
208000018152 Cerebral disease Diseases 0.000 description 1
241001432959 Chernes Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
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 1
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 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 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
235000014435 Mentha Nutrition 0.000 description 1
241001072983 Mentha Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
QFRPEFMNOWVDJY-UHFFFAOYSA-N N.C1CCCC1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 Chemical compound N.C1CCCC1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 QFRPEFMNOWVDJY-UHFFFAOYSA-N 0.000 description 1
PBGBTRPQDTVPPX-UHFFFAOYSA-N N.C=1C=CC=CC=1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 Chemical compound N.C=1C=CC=CC=1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 PBGBTRPQDTVPPX-UHFFFAOYSA-N 0.000 description 1
VMNFQDHDVBXBDZ-UHFFFAOYSA-N N.CCCCC1=NC2=CC=C3C=CN=CC3=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 Chemical compound N.CCCCC1=NC2=CC=C3C=CN=CC3=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 VMNFQDHDVBXBDZ-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
201000003099 Renovascular Hypertension Diseases 0.000 description 1
229910004298 SiO 2 Inorganic materials 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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
BIARPNYRLKEWNS-UHFFFAOYSA-N [7-methyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridin-2-yl]methanol Chemical compound OCC1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 BIARPNYRLKEWNS-UHFFFAOYSA-N 0.000 description 1
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 1
239000013543 active substance Substances 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
PTIJNLYCNAKLOJ-UHFFFAOYSA-N azane 2-ethylsulfanyl-7-methyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound N.CCSC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 PTIJNLYCNAKLOJ-UHFFFAOYSA-N 0.000 description 1
KEQWWYWEYZZYHG-UHFFFAOYSA-N azane;1h-benzimidazole Chemical compound N.C1=CC=C2NC=NC2=C1 KEQWWYWEYZZYHG-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
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
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229940116229 borneol Drugs 0.000 description 1
CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
239000001354 calcium citrate Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
230000003684 cardiac depression Effects 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229960001777 castor oil Drugs 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229960002242 chlorocresol Drugs 0.000 description 1
229940017545 cinnamon bark Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
229940013361 cresol Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 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
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
201000005857 malignant hypertension Diseases 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
IHNIAWHITVGYJJ-UHFFFAOYSA-N methyl 2-(4-methylphenyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=C(C)C=C1 IHNIAWHITVGYJJ-UHFFFAOYSA-N 0.000 description 1
VPGKEWDYZDYDAL-UHFFFAOYSA-N methyl 2-[4-[(7-chloro-2-propylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoate Chemical compound CCCC1=NC2=C(Cl)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(=O)OC VPGKEWDYZDYDAL-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000011587 new zealand white rabbit Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
230000007170 pathology Effects 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
239000001814 pectin Substances 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
HSMKTIKKPMTUQH-WBPXWQEISA-L pentolinium tartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O.OC(=O)[C@H](O)[C@@H](O)C([O-])=O.C1CCC[N+]1(C)CCCCC[N+]1(C)CCCC1 HSMKTIKKPMTUQH-WBPXWQEISA-L 0.000 description 1
229950008637 pentolonium Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000012256 powdered iron Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
239000003451 thiazide diuretic agent Substances 0.000 description 1
239000012929 tonicity agent Substances 0.000 description 1
235000013337 tricalcium citrate Nutrition 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
- 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
- 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
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

DD90344302A 1989-09-29 1990-09-28 Biphenylmethanderivate sowie dessen pharmakologische verwendung DD299301A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP25176189		1989-09-29
JP33664089		1989-12-27

Publications (1)

Publication Number	Publication Date
DD299301A5 true DD299301A5 (de)	1992-04-09

Family

ID=26540341

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90344302A DD299301A5 (de)	1989-09-29	1990-09-28	Biphenylmethanderivate sowie dessen pharmakologische verwendung

Country Status (21)

Country	Link
US (1)	US5328911A (ja)
EP (3)	EP0628557B1 (ja)
JP (2)	JP2608341B2 (ja)
KR (1)	KR930000168B1 (ja)
CN (1)	CN1025331C (ja)
AT (3)	ATE134998T1 (ja)
AU (1)	AU641685B2 (ja)
CA (1)	CA2026533A1 (ja)
DD (1)	DD299301A5 (ja)
DE (3)	DE69030631T2 (ja)
DK (1)	DK0420237T3 (ja)
ES (1)	ES2085876T3 (ja)
FI (1)	FI94527C (ja)
GR (1)	GR3019239T3 (ja)
HU (1)	HUT55367A (ja)
IE (1)	IE70593B1 (ja)
MX (1)	MXPA95000470A (ja)
NO (1)	NO176912C (ja)
NZ (1)	NZ235469A (ja)
PT (1)	PT95464B (ja)
RU (1)	RU2024521C1 (ja)

Families Citing this family (75)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0273071A (ja) *	1988-09-09	1990-03-13	Sumitomo Chem Co Ltd	ベンズイミダゾール誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤
GB8911854D0 (en) *	1989-05-23	1989-07-12	Ici Plc	Heterocyclic compounds
IE64514B1 (en) *	1989-05-23	1995-08-09	Zeneca Ltd	Azaindenes
IL94390A (en) *	1989-05-30	1996-03-31	Merck & Co Inc	The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them
US5332744A (en) *	1989-05-30	1994-07-26	Merck & Co., Inc.	Substituted imidazo-fused 6-membered heterocycles as angiotensin II antagonists
US5223499A (en) *	1989-05-30	1993-06-29	Merck & Co., Inc.	6-amino substituted imidazo[4,5-bipyridines as angiotensin II antagonists
IL95975A (en) *	1989-10-24	1997-06-10	Takeda Chemical Industries Ltd	N-benzyl- 2-alkylbenzimidazole derivatives, their production and pharmaceutical compositions containing them
US5250554A (en) *	1989-10-24	1993-10-05	Takeda Chemical Industries, Ltd.	Benzimidazole derivatives useful as angiotensin II inhibitors
IL97219A (en) *	1990-02-19	1995-12-08	Ciba Geigy Ag	Biphenyl substituted aliphatic amino compounds process for their preparation and pharmaceutical compositions containing them
DE4006693A1 (de) *	1990-03-01	1991-09-05	Schering Ag	Neue benzimidazolderivate, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
US5196444A (en) *	1990-04-27	1993-03-23	Takeda Chemical Industries, Ltd.	1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate and compositions and methods of pharmaceutical use thereof
US6004989A (en)	1990-04-27	1999-12-21	Takeda Chemical Industries, Ltd.	Benzimidazole derivatives, their production and use
US5703110A (en) *	1990-04-27	1997-12-30	Takeda Chemical Industries, Ltd.	Benzimidazole derivatives, their production and use
US5194379A (en) *	1990-05-11	1993-03-16	Merck & Co., Inc.	Microbial transformation process for the preparation of hydroxylanol imidazo (4,5-b) pyridines useful as angiotensin II receptor antagonists
FR2670489B1 (fr) *	1990-12-18	1994-10-14	Roussel Uclaf	Nouveaux derives de benzimidazole, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant.
ES2121773T3 (es) *	1990-06-08	1998-12-16	Hoechst Marion Roussel Inc	Derivados de bencimidazol, su procedimiento de preparacion, productos intermedios, su aplicacion como medicamentos y composiciones farmaceuticas que los contienen.
FR2674523A1 (fr) *	1991-03-28	1992-10-02	Roussel Uclaf	Nouveaux derives de benzimidazole, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant.
DE4023215A1 (de) *	1990-07-21	1992-01-23	Hoechst Ag	Substituierte azole, verfahren zu deren herstellung, sie enthaltende mittel und deren verwendung
DE4023369A1 (de) *	1990-07-23	1992-01-30	Thomae Gmbh Dr K	Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
RU1836357C (ru) *	1990-07-23	1993-08-23	Др.Карл Томэ ГмбХ	Производные бензимидазола, их изомеры, смеси изомеров, гидраты или их физиологически переносимые соли, обладающие антагонистическими в отношении ангиотензина свойствами
EP0470543A1 (de) *	1990-08-10	1992-02-12	Dr. Karl Thomae GmbH	Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung
US5210206A (en) *	1990-09-10	1993-05-11	Abbott Laboratories	1,3-oxazolyl substituted biphenyl
AU636066B2 (en) *	1990-10-30	1993-04-08	Takeda Chemical Industries Ltd.	Thienoimidazole derivatives, their production and use
SI9210098B (sl) *	1991-02-06	2000-06-30	Dr. Karl Thomae	Benzimidazoli, zdravila, ki te spojine vsebujejo, in postopek za njihovo pripravo
TW274551B (ja) *	1991-04-16	1996-04-21	Takeda Pharm Industry Co Ltd
KR920021542A (ko) *	1991-05-16	1992-12-18	배리 안토니 뉴샘	벤조푸란 유도체
IL102183A (en) *	1991-06-27	1999-11-30	Takeda Chemical Industries Ltd	Biphenyl substituted heterocyclic compounds their production and pharmaceutical compositions comprising them
EP0531874A1 (en) *	1991-09-10	1993-03-17	Tanabe Seiyaku Co., Ltd.	Imidazopyridine derivatives and process for preparation thereof
TW300219B (ja) *	1991-09-14	1997-03-11	Hoechst Ag
TW284688B (ja) *	1991-11-20	1996-09-01	Takeda Pharm Industry Co Ltd
GB9201715D0 (en) *	1992-01-28	1992-03-11	Ici Plc	Chemical process
DE4219534A1 (de) *	1992-02-19	1993-12-16	Thomae Gmbh Dr K	Substituierte Biphenylylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
US5208234A (en) *	1992-03-10	1993-05-04	E. R. Squibb & Sons, Inc.	Substituted imidazole phosphonic and phosphinic acid derivatives
CA2109932A1 (en) *	1992-03-25	1993-09-30	Yoshihisa Inoue	Isoindazole compound
DE4305602A1 (de) *	1992-06-17	1993-12-23	Merck Patent Gmbh	Imidazopyridine
US5583229A (en) *	1992-12-07	1996-12-10	Eisai Co., Ltd.	Process for the preparation of imidazopyridine derivatives
SK2895A3 (en) *	1992-07-10	1995-07-11	Boots Co Plc	Substituted 3-cyclobutene-1,2-diones, method of their preparation and pharmaceutical agents which containing thereof
JPH07509464A (ja) *	1992-07-17	1995-10-19	メルク　エンド　カンパニー　インコーポレーテッド	置換ビフェニルメチルイミダゾピリジン
RU2109736C1 (ru) *	1992-12-17	1998-04-27	Санкио Компани Лимитед	Производные бифенила и способ их получения
DE4320432A1 (de) *	1993-06-21	1994-12-22	Bayer Ag	Substituierte Mono- und Bipyridylmethylderivate
US5338740A (en) *	1993-07-13	1994-08-16	Pfizer Inc.	Angiotensin II receptor antagonists
KR0151816B1 (ko) *	1994-02-08	1998-10-15	강박광	신규의 치환된 피리딜 이미다졸 유도체 및 그의 제조방법
US5753672A (en) *	1994-04-19	1998-05-19	Tanabe Seiyaku Co., Ltd.	Imidazopyridine derivatives and process for preparing the same
US5994361A (en) *	1994-06-22	1999-11-30	Biochem Pharma	Substituted purinyl derivatives with immunomodulating activity
FR2725987B1 (fr) *	1994-10-19	1997-01-10	Sanofi Sa	Procede pour la preparation d'un derive de tetrazole sous deux formes cristallines et nouvelle forme cristalline de ce derive
IL123147A (en) *	1995-08-02	2004-02-19	Univ Newcastle Ventures Ltd	Benzamide imidazole - 4 carboxamide and their use
AU7213296A (en) *	1995-10-06	1997-04-30	Ciba-Geigy Ag	At1-receptor antagonists for preventing and treating postischemic renal failure and for protecting ischemic kidneys
UA62972C2 (en) *	1997-07-03	2004-01-15		Application of imidazopyrimidins and imidazopyridins for the treatment of neural disorders
TW526202B (en) *	1998-11-27	2003-04-01	Shionogi & Amp Co	Broad spectrum cephem having benzo[4,5-b]pyridium methyl group of antibiotic activity
US6465502B1 (en)	1998-12-23	2002-10-15	Novartis Ag	Additional therapeutic use
ATE524176T1 (de)	1998-12-23	2011-09-15	Novartis Pharma Gmbh	Valsartan tablette
CN101011390A (zh)	1999-01-26	2007-08-08	诺瓦提斯公司	血管紧张素ⅱ受体拮抗剂在治疗急性心肌梗塞中的应用
US6211217B1 (en)	1999-03-16	2001-04-03	Novartis Ag	Method for reducing pericardial fibrosis and adhesion formation
GB9919778D0 (en) *	1999-08-21	1999-10-27	Zeneca Ltd	Chemical compounds
SE9903028D0 (sv)	1999-08-27	1999-08-27	Astra Ab	New use
DE10335027A1 (de)	2003-07-31	2005-02-17	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verwendung von Angiotensin II Rezeptor Antagonisten
AU2003242984A1 (en) *	2003-04-07	2004-11-01	Hetero Drugs Limited	A novel crystalline form of irbesartan
UA85937C2 (uk)	2004-12-21	2009-03-10	Пфайзер Продактс Інк.	Макроліди
EP1908469A1 (en)	2006-10-06	2008-04-09	Boehringer Ingelheim Vetmedica Gmbh	Angiotensin II receptor antagonist for the treatment of systemic diseases in cats
KR101126383B1 (ko)	2007-02-07	2012-04-12	교와 핫꼬 기린 가부시키가이샤	3환계 화합물
US8969514B2 (en)	2007-06-04	2015-03-03	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
EP2527360B1 (en)	2007-06-04	2015-10-28	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
KR101009383B1 (ko)	2008-04-30	2011-01-19	켐젠주식회사	고순도의2-부틸-3-[[2'-(1에이취-테트라졸-5-일)[1,1'-비페닐]-4-일]메틸]-1,3-디아자스피로[4.4]논-1-엔-4-온 화합물의제조방법
EP2810951B1 (en)	2008-06-04	2017-03-15	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
EP3241839B1 (en)	2008-07-16	2019-09-04	Bausch Health Ireland Limited	Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
KR20130076046A (ko) *	2011-12-28	2013-07-08	한미약품 주식회사	타이로신 카이네이즈 억제 활성을 갖는 신규 이미다조피리딘 유도체
CA2905435A1 (en)	2013-03-15	2014-09-25	Synergy Pharmaceuticals Inc.	Compositions useful for the treatment of gastrointestinal disorders
CA2905438A1 (en)	2013-03-15	2014-09-25	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase and their uses
SI3004138T1 (sl)	2013-06-05	2024-07-31	Bausch Health Ireland Limited	Ultra čisti agonisti gvanilat ciklaze C, postopek za njihovo pripravo in uporabo
DK3648761T3 (da)	2017-07-07	2024-06-24	Boehringer Ingelheim Vetmedica Gmbh	Telmisartan til forebyggelsen eller behandlingen af hypertension i katte
MX2022000426A (es)	2019-07-09	2022-04-25	Boehringer Ingelheim Vetmedica Gmbh	Telmisartan para el tratamiento de la hipertension en perros.
CN118765309A (zh) *	2022-03-08	2024-10-11	科巨希化学股份有限公司	含有高安全性酰胺化合物的组合物
CN121175053A (zh)	2023-05-24	2025-12-19	勃林格殷格翰动物保健有限公司	包含一或多种sglt-2抑制剂及替米沙坦的非人类哺乳动物中肾脏疾病和/或高血压的组合治疗和/或预防
TW202541793A (zh)	2023-12-15	2025-11-01	德商百靈佳殷格翰維美迪加股份有限公司	用於預防貓之全身性疾病之血管緊張素ii受體拮抗劑

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1334092C (en) *	1986-07-11	1995-01-24	David John Carini	Angiotensin ii receptor blocking imidazoles
US4874867A (en) *	1987-05-22	1989-10-17	E. I. Du Pont De Nemours And Company	Tetrazole intermediates to antihypertensive compounds
US4820843A (en) *	1987-05-22	1989-04-11	E. I. Du Pont De Nemours And Company	Tetrazole intermediates to antihypertensive compounds
US4870186A (en) *	1987-05-22	1989-09-26	E. I. Du Pont De Nemours And Company	Tetrazole intermediates to antihypertensive compounds
US4880804A (en) *	1988-01-07	1989-11-14	E. I. Du Pont De Nemours And Company	Angiotensin II receptor blocking benzimidazoles
US4916129A (en) *	1989-01-19	1990-04-10	E. I. Du Pont De Nemours And Company	Combination β-blocking/angiotensin II blocking antihypertensives
DE3928177A1 (de) *	1989-04-08	1991-02-28	Thomae Gmbh Dr K	Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP0400835A1 (en) *	1989-05-15	1990-12-05	Merck & Co. Inc.	Substituted benzimidazoles as angiotensin II antagonists
GB8911854D0 (en) *	1989-05-23	1989-07-12	Ici Plc	Heterocyclic compounds
IE64514B1 (en) *	1989-05-23	1995-08-09	Zeneca Ltd	Azaindenes
IL94390A (en) *	1989-05-30	1996-03-31	Merck & Co Inc	The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them
EP0415886A3 (en) *	1989-08-30	1991-10-23	Ciba-Geigy Ag	Aza compounds
IL95975A (en) *	1989-10-24	1997-06-10	Takeda Chemical Industries Ltd	N-benzyl- 2-alkylbenzimidazole derivatives, their production and pharmaceutical compositions containing them
IL96019A0 (en) *	1989-10-31	1991-07-18	Fujisawa Pharmaceutical Co	Imidazole derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same
EP0434038A1 (en) *	1989-12-22	1991-06-26	Takeda Chemical Industries, Ltd.	Fused imidazole derivatives, their production and use
US5196444A (en) *	1990-04-27	1993-03-23	Takeda Chemical Industries, Ltd.	1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate and compositions and methods of pharmaceutical use thereof
CA2041763A1 (en) *	1990-05-11	1991-11-12	Sheih-Shung T. Chen	Microbial transformation process for antihypertensive products
ES2121773T3 (es) *	1990-06-08	1998-12-16	Hoechst Marion Roussel Inc	Derivados de bencimidazol, su procedimiento de preparacion, productos intermedios, su aplicacion como medicamentos y composiciones farmaceuticas que los contienen.
AU653524B2 (en) *	1990-06-08	1994-10-06	Roussel-Uclaf	New imidazole derivatives, their preparation process, the new intermediates obtained, their use as medicaments and the pharmaceutical compositions containing them
CA2044806A1 (en) *	1990-07-18	1992-01-19	Roland Jaunin	Purine derivatives
RU1836357C (ru) *	1990-07-23	1993-08-23	Др.Карл Томэ ГмбХ	Производные бензимидазола, их изомеры, смеси изомеров, гидраты или их физиологически переносимые соли, обладающие антагонистическими в отношении ангиотензина свойствами
EP0470543A1 (de) *	1990-08-10	1992-02-12	Dr. Karl Thomae GmbH	Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung

1990
- 1990-09-06 IE IE324290A patent/IE70593B1/en not_active IP Right Cessation
- 1990-09-07 FI FI904424A patent/FI94527C/fi not_active IP Right Cessation
- 1990-09-13 US US07/583,025 patent/US5328911A/en not_active Expired - Fee Related
- 1990-09-21 AU AU63075/90A patent/AU641685B2/en not_active Ceased
- 1990-09-26 NZ NZ235469A patent/NZ235469A/xx unknown
- 1990-09-27 ES ES90118565T patent/ES2085876T3/es not_active Expired - Lifetime
- 1990-09-27 DE DE69030631T patent/DE69030631T2/de not_active Expired - Fee Related
- 1990-09-27 NO NO904202A patent/NO176912C/no unknown
- 1990-09-27 EP EP94109556A patent/EP0628557B1/en not_active Expired - Lifetime
- 1990-09-27 EP EP94101415A patent/EP0598702B1/en not_active Expired - Lifetime
- 1990-09-27 EP EP90118565A patent/EP0420237B1/en not_active Expired - Lifetime
- 1990-09-27 DK DK90118565.2T patent/DK0420237T3/da active
- 1990-09-27 AT AT90118565T patent/ATE134998T1/de active
- 1990-09-27 AT AT94101415T patent/ATE167186T1/de active
- 1990-09-27 HU HU906243A patent/HUT55367A/hu unknown
- 1990-09-27 AT AT94109556T patent/ATE152451T1/de not_active IP Right Cessation
- 1990-09-27 DE DE69032414T patent/DE69032414T2/de not_active Expired - Fee Related
- 1990-09-27 DE DE69025687T patent/DE69025687T2/de not_active Expired - Fee Related
- 1990-09-28 RU SU904831238A patent/RU2024521C1/ru active
- 1990-09-28 JP JP2257400A patent/JP2608341B2/ja not_active Expired - Lifetime
- 1990-09-28 CA CA002026533A patent/CA2026533A1/en not_active Abandoned
- 1990-09-28 PT PT95464A patent/PT95464B/pt not_active IP Right Cessation
- 1990-09-28 DD DD90344302A patent/DD299301A5/de not_active IP Right Cessation
- 1990-09-29 KR KR1019900015702A patent/KR930000168B1/ko not_active Expired - Fee Related
- 1990-09-29 CN CN90108025A patent/CN1025331C/zh not_active Expired - Fee Related
1994
- 1994-12-02 JP JP6299389A patent/JP2925962B2/ja not_active Expired - Lifetime
1995
- 1995-01-12 MX MXPA95000470A patent/MXPA95000470A/es unknown
1996
- 1996-03-07 GR GR960400236T patent/GR3019239T3/el unknown

Also Published As

Publication number	Publication date
HU906243D0 (en)	1991-03-28
DE69032414D1 (de)	1998-07-16
DE69025687T2 (de)	1996-08-08
IE70593B1 (en)	1996-12-11
FI94527B (fi)	1995-06-15
DE69030631T2 (de)	1997-09-25
ES2085876T3 (es)	1996-06-16
EP0628557A1 (en)	1994-12-14
EP0598702B1 (en)	1998-06-10
KR930000168B1 (ko)	1993-01-11
EP0628557B1 (en)	1997-05-02
EP0598702A1 (en)	1994-05-25
JP2608341B2 (ja)	1997-05-07
ATE134998T1 (de)	1996-03-15
JP2925962B2 (ja)	1999-07-28
DE69030631D1 (de)	1997-06-05
EP0420237B1 (en)	1996-03-06
DK0420237T3 (da)	1996-07-01
PT95464B (pt)	1997-07-31
NZ235469A (en)	1993-03-26
NO904202L (no)	1991-04-02
NO176912C (no)	1995-06-21
HUT55367A (en)	1991-05-28
EP0420237A1 (en)	1991-04-03
JPH03236377A (ja)	1991-10-22
NO176912B (no)	1995-03-13
CA2026533A1 (en)	1991-03-30
AU641685B2 (en)	1993-09-30
NO904202D0 (no)	1990-09-27
US5328911A (en)	1994-07-12
AU6307590A (en)	1991-04-11
CN1025331C (zh)	1994-07-06
FI904424A0 (fi)	1990-09-07
RU2024521C1 (ru)	1994-12-15
JPH07224059A (ja)	1995-08-22
ATE167186T1 (de)	1998-06-15
CN1050539A (zh)	1991-04-10
KR910006287A (ko)	1991-04-29
PT95464A (pt)	1991-05-22
DE69025687D1 (de)	1996-04-11
MXPA95000470A (es)	2004-08-17
FI94527C (fi)	1995-09-25
DE69032414T2 (de)	1998-11-19
IE903242A1 (en)	1991-04-10
GR3019239T3 (en)	1996-06-30
ATE152451T1 (de)	1997-05-15

Legal Events

Date	Code	Title	Description
2002-10-10	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD299301A5 (de)	1992-04-09	Biphenylmethanderivate sowie dessen pharmakologische verwendung
EP0468470B1 (de)	1997-04-16	Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EP0450566B1 (de)	1995-07-05	Substituierte Azole, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung
DE59209330C5 (de)	2013-10-31	Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE4031287A1 (de)	1992-04-09	Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP1127880A2 (de)	2001-08-29	Heterocyclisch substituierte Phenylessigsäurederivate und deren Verwendung als A-II-Antagonisten und als Inhibitoren der Proliferation von glatten Muskelzellen
CH516574A (de)	1971-12-15	Verfahren zur Herstellung von 1H-Imidazo(3,5-b)pyrazin-2-onen
EP0682021A1 (de)	1995-11-15	Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE4036645A1 (de)	1992-05-21	Substituierte azole, verfahren zu deren herstellung, deren enthaltende mittel und deren verwendung
DE4142366A1 (de)	1993-06-24	Phenylalkylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
US5298518A (en)	1994-03-29	Biphenylmethane derivative and pharmacological use
EP0552765B1 (de)	1996-08-14	Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE2637477A1 (de)	1978-02-23	Dihydro-oxo-nicotinsaeuren und verfahren zu ihrer herstellung
EP0543263A2 (de)	1993-05-26	Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EP0560330A2 (de)	1993-09-15	Substituierte Benzimidazolylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE1695115A1 (de)	1972-03-30	Verfahren zur Herstellung von neuen Furazanderivaten
EP0037471B1 (de)	1984-05-30	1-Aroyl-2-phenylamino-2-imidazoline, ihre Herstellung und diese enthaltende Arzneimittel
DE2651580A1 (de)	1978-06-22	Neue imidazolverbindungen, verfahren zu deren herstellung und diese enthaltende arzneimittel
EP0083729A1 (de)	1983-07-20	Substituierte 1-Benzoyl-2-phenylimino-imidazolidine, deren Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
AT358033B (de)	1980-08-11	Verfahren zur herstellung neuer imidazol- derivate und ihrer salze
AT375347B (de)	1984-07-25	Verfahren zur herstellung von neuen substituierten 1-benzoyl-2-phenylimino-imidazolidinen und von deren salzen
DE4201554A1 (de)	1993-07-29	Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung