NL8502384A - Benzimidazoolderivaten, farmaceutische preparaten met een werking tegen zweren die ze bevatten en werkwijzen voor het bereiden van deze derivaten. - Google Patents

Benzimidazoolderivaten, farmaceutische preparaten met een werking tegen zweren die ze bevatten en werkwijzen voor het bereiden van deze derivaten. Download PDF

Info

Publication number: NL8502384A
Authority: NL; Netherlands
Prior art keywords: benzimidazole; compound; formula; solution; derivatives
Prior art date: 1984-08-31

Application number

NL8502384A

Other languages

English (en)

Dutch (nl)

Original Assignee

Nippon Chemiphar Co

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.)

1984-08-31

Filing date

1985-08-30

Publication date

1986-03-17

1984-08-31 Priority claimed from JP59182400A external-priority patent/JPS6160660A/ja

1985-03-26 Priority claimed from JP60061194A external-priority patent/JPH068283B2/ja

1985-03-26 Priority claimed from JP60061195A external-priority patent/JPH0764826B2/ja

1985-08-30 Application filed by Nippon Chemiphar Co filed Critical Nippon Chemiphar Co

1986-03-17 Publication of NL8502384A publication Critical patent/NL8502384A/nl

Links

150000001556 benzimidazoles Chemical class 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 12
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 11
239000000825 pharmaceutical preparation Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 55
238000002360 preparation method Methods 0.000 claims description 14
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 10
-1 2-aminobenzyl compound Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
230000000767 anti-ulcer Effects 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
239000013078 crystal Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
230000002829 reductive effect Effects 0.000 description 21
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
230000003628 erosive effect Effects 0.000 description 9
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102000057290 Adenosine Triphosphatases Human genes 0.000 description 8
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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 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
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125000003118 aryl group Chemical group 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000010410 layer Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
BLKLDWQFHUIMPR-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 BLKLDWQFHUIMPR-UHFFFAOYSA-N 0.000 description 4
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239000002253 acid Substances 0.000 description 4
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238000004519 manufacturing process Methods 0.000 description 4
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DVMJQEIKYMPLRN-UHFFFAOYSA-N 2-[(2-piperidin-1-ylphenyl)methylsulfanyl]-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CC=C1N1CCCCC1 DVMJQEIKYMPLRN-UHFFFAOYSA-N 0.000 description 3
ICJZQAGBAOZSTB-UHFFFAOYSA-N 2-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC1=CC=CC=C1N(C)C ICJZQAGBAOZSTB-UHFFFAOYSA-N 0.000 description 3
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UZNORZYEAOXIAO-UHFFFAOYSA-N N,N-dimethyl-2-[(4-methyl-1H-benzimidazol-2-yl)sulfanylmethyl]aniline Chemical compound CN(C1=C(CSC=2NC3=C(N2)C=CC=C3C)C=CC=C1)C UZNORZYEAOXIAO-UHFFFAOYSA-N 0.000 description 3
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208000007107 Stomach Ulcer Diseases 0.000 description 3
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231100000397 ulcer Toxicity 0.000 description 3
VSLKTMFOYIAAKO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n-methylaniline Chemical compound CNC1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 VSLKTMFOYIAAKO-UHFFFAOYSA-N 0.000 description 2
PSXUBLNOGFVJRX-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 PSXUBLNOGFVJRX-UHFFFAOYSA-N 0.000 description 2
INGIXPMMNAFVHF-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)aniline Chemical compound NC1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 INGIXPMMNAFVHF-UHFFFAOYSA-N 0.000 description 2
FNCFJTCLEAAISA-UHFFFAOYSA-N 2-[(2-piperidin-1-ylphenyl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=C1N1CCCCC1 FNCFJTCLEAAISA-UHFFFAOYSA-N 0.000 description 2
IJINDUSMSVDESS-UHFFFAOYSA-N 2-benzylsulfanyl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CC=C1 IJINDUSMSVDESS-UHFFFAOYSA-N 0.000 description 2
FVABKKHWAAELQW-UHFFFAOYSA-N 2-benzylsulfinyl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=C1 FVABKKHWAAELQW-UHFFFAOYSA-N 0.000 description 2
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238000004587 chromatography analysis Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000001120 cytoprotective effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229940080428 lactose 200 mg Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
DVCQNMAKXHNXAH-UHFFFAOYSA-N n,n-dimethyl-2-[(4-methyl-1h-benzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=C(C)C=CC=C2N1 DVCQNMAKXHNXAH-UHFFFAOYSA-N 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NL8502384A 1984-08-31 1985-08-30 Benzimidazoolderivaten, farmaceutische preparaten met een werking tegen zweren die ze bevatten en werkwijzen voor het bereiden van deze derivaten. NL8502384A (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP18240084		1984-08-31
JP59182400A JPS6160660A (ja)	1984-08-31	1984-08-31	ベンズイミダゾ−ル誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
JP60061194A JPH068283B2 (ja)	1985-03-26	1985-03-26	ベンズイミダゾ−ル誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
JP6119585		1985-03-26
JP6119485		1985-03-26
JP60061195A JPH0764826B2 (ja)	1985-03-26	1985-03-26	ベンズイミダゾール誘導体

Publications (1)

Publication Number	Publication Date
NL8502384A true NL8502384A (nl)	1986-03-17

Family

ID=27297422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8502384A NL8502384A (nl)	1984-08-31	1985-08-30	Benzimidazoolderivaten, farmaceutische preparaten met een werking tegen zweren die ze bevatten en werkwijzen voor het bereiden van deze derivaten.

Country Status (14)

Country	Link
KR (1)	KR920004936B1 (fr)
AR (1)	AR242195A1 (fr)
AU (3)	AU4640985A (fr)
BE (1)	BE903128A (fr)
BR (1)	BR8504252A (fr)
CH (1)	CH665417A5 (fr)
DE (1)	DE3531487C2 (fr)
ES (1)	ES8703142A1 (fr)
FR (1)	FR2569691B1 (fr)
GB (1)	GB2163747B (fr)
IT (1)	IT1189601B (fr)
MX (1)	MX159807A (fr)
NL (1)	NL8502384A (fr)
SE (1)	SE500669C2 (fr)

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EP0174717A1 (fr)	1984-07-06	1986-03-19	FISONS plc	Benzimidazoles, et leur préparation, formulation et application comme inhibiteur de sécrétion d'acide gastrique

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DE60323474D1 (de)	2002-04-09	2008-10-23	Flamel Tech Sa	Orale pharmazeutische formulierung in form einer wässrigen suspension von mikrokapseln zur modifizierten freisetzung von amoxicillin
SE0203065D0 (sv)	2002-10-16	2002-10-16	Diabact Ab	Gastric acid secretion inhibiting composition
EP2112920B1 (fr)	2003-06-26	2018-07-25	Intellipharmaceutics Corp.	Capsules contenant un inhibiteur de la pompe a protons comprenant des unites secondaires differemment structurees permettant une liberation retardee de l'ingredient actif
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US10624858B2 (en)	2004-08-23	2020-04-21	Intellipharmaceutics Corp	Controlled release composition using transition coating, and method of preparing same
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EA201100313A1 (ru)	2008-09-09	2011-10-31	Астразенека Аб	Способ доставки фармацевтической композиции пациенту, нуждающемуся в этом
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1985
- 1985-08-19 AU AU46409/85A patent/AU4640985A/en not_active Abandoned
- 1985-08-27 ES ES546445A patent/ES8703142A1/es not_active Expired
- 1985-08-27 BE BE0/215506A patent/BE903128A/fr not_active IP Right Cessation
- 1985-08-29 CH CH3709/85A patent/CH665417A5/fr not_active IP Right Cessation
- 1985-08-29 GB GB08521493A patent/GB2163747B/en not_active Expired
- 1985-08-30 NL NL8502384A patent/NL8502384A/nl not_active Application Discontinuation
- 1985-08-30 IT IT67743/85A patent/IT1189601B/it active
- 1985-08-30 MX MX206462A patent/MX159807A/es unknown
- 1985-08-30 BR BR8504252A patent/BR8504252A/pt unknown
- 1985-08-30 KR KR1019850006307A patent/KR920004936B1/ko not_active Expired
- 1985-08-30 FR FR858512961A patent/FR2569691B1/fr not_active Expired
- 1985-08-30 AR AR85301474A patent/AR242195A1/es active
- 1985-08-30 SE SE8504048A patent/SE500669C2/sv unknown
- 1985-08-30 DE DE3531487A patent/DE3531487C2/de not_active Expired - Fee Related
1989
- 1989-09-11 AU AU41271/89A patent/AU4127189A/en not_active Abandoned
1992
- 1992-11-27 AU AU29750/92A patent/AU647978B2/en not_active Ceased

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0174717A1 (fr)	1984-07-06	1986-03-19	FISONS plc	Benzimidazoles, et leur préparation, formulation et application comme inhibiteur de sécrétion d'acide gastrique

Also Published As

Publication number	Publication date
AU2975092A (en)	1993-01-28
BE903128A (fr)	1985-12-16
GB2163747A (en)	1986-03-05
FR2569691A1 (fr)	1986-03-07
GB8521493D0 (en)	1985-10-02
BR8504252A (pt)	1986-06-17
AU4640985A (en)	1986-03-06
GB2163747B (en)	1989-02-08
AU4127189A (en)	1989-12-21
DE3531487C2 (de)	1995-08-17
SE8504048L (sv)	1986-03-01
KR860001793A (ko)	1986-03-22
ES546445A0 (es)	1986-11-16
AR242195A1 (es)	1993-03-31
KR920004936B1 (ko)	1992-06-22
IT8567743A0 (it)	1985-08-30
FR2569691B1 (fr)	1989-08-04
AU647978B2 (en)	1994-03-31
SE8504048D0 (sv)	1985-08-30
SE500669C2 (sv)	1994-08-08
MX159807A (es)	1989-08-31
ES8703142A1 (es)	1986-11-16
CH665417A5 (fr)	1988-05-13
IT1189601B (it)	1988-02-04
DE3531487A1 (de)	1986-03-13

Legal Events

Date	Code	Title
1992-09-01	BA	A request for search or an international-type search has been filed
1992-09-01	BB	A search report has been drawn up
1992-11-02	BC	A request for examination has been filed
2001-05-01	BV	The patent application has lapsed

Publication	Publication Date	Title
AU647978B2 (en)	1994-03-31	Benzimidazole derivatives
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US5977118A (en)	1999-11-02	6-substituted pyrazolo[3,4-d]pyrimidin-4-ones and compositions and methods of use thereof
FI79104C (fi)	1989-11-10	Foerfarande foer framstaellning av ett nytt terapeutiskt anvaendbart dihydropyridinderivat.
SK93297A3 (en)	1998-02-04	Indole derivatives, method for their producing, pharmaceutical comosition containing the same, and their use
FR2529547A1 (fr)	1984-01-06	Derives n-imidazolyliques de composes bicycliques, leur procede de preparation et leur utilisation dans le reglage de l'hemostase vasculaire
NO316666B1 (no)	2004-03-29	Kinolonkarboksylsyrederivater eller deres salter
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Sondhi et al.	2008	Synthesis of some thiophene, imidazole and pyridine derivatives exhibiting good anti-inflammatory and analgesic activities
FR2727680A1 (fr)	1996-06-07	Nouveaux derives de 5-pyrrolyl-6-halogeno-2- pyridylmethylsufinylbenzimidazole
EP0758649A1 (fr)	1997-02-19	Dérivés de chromone, procédé pour leur préparation et composition pharmaceutique
JP2009506127A (ja)	2009-02-12	糖尿病の処置に有用なアニリノピラゾール誘導体
EP0846689A1 (fr)	1998-06-10	Composés de benzimidazole
HU194174B (en)	1988-01-28	Process for preparing pyridylvinyl carboxylic acid derivatives and pharmaceuticals comprising the same as active substance
US20050272781A1 (en)	2005-12-08	Methods for the synthesis of pyridoxamine
CZ281810B6 (cs)	1997-02-12	Nové hetaryloxy-beta-karboliny, způsob jejich výroby a použití ve farmaceutických prostředcích
MX2015006536A (es)	2015-07-23	Derivados de piridona como inhibidores de secrecion acida y proceso para la preparacion de los mismos.
ZA200204313B (en)	2003-08-29	Substituted pyrroles.
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FI91871B (fi)	1994-05-13	Menetelmä lääkeaineina käyttökelpoisten 1H-imidatso/1,2-b/-pyratsolin johdannaisten valmistamiseksi
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NL8502384A - Benzimidazoolderivaten, farmaceutische preparaten met een werking tegen zweren die ze bevatten en werkwijzen voor het bereiden van deze derivaten. - Google Patents

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