ZA200104620B - Benzoxazole derivatives and medicaments comprising said derivatives as active ingredient. - Google Patents

Benzoxazole derivatives and medicaments comprising said derivatives as active ingredient. Download PDF

Info

Publication number: ZA200104620B
Authority: ZA; South Africa
Prior art keywords: group; homopiperazinyl; chloro; lower alkyl; alkyl group
Prior art date: 1998-11-20

Application number

ZA200104620A

Other languages

English (en)

Inventor

Sojiro Shiokawa

Yasuo Sato

Masaaki Izumi

Satoshi Yoshida

Hiroshi Murakami

Tomoko Ito

Tetsutaro Niisato

Original Assignee

Meiji Seika Kaisha

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.)

1998-11-20

Filing date

2001-06-06

Publication date

2002-02-04

2001-06-06 Application filed by Meiji Seika Kaisha filed Critical Meiji Seika Kaisha

2002-02-04 Publication of ZA200104620B publication Critical patent/ZA200104620B/en

Links

239000003814 drug Substances 0.000 title claims description 25
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims description 13
239000004480 active ingredient Substances 0.000 title claims description 10
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 74
150000001875 compounds Chemical class 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000003277 amino group Chemical group 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
230000003042 antagnostic effect Effects 0.000 claims description 13
208000002551 irritable bowel syndrome Diseases 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
230000001225 therapeutic effect Effects 0.000 claims description 12
206010012735 Diarrhoea Diseases 0.000 claims description 11
210000001035 gastrointestinal tract Anatomy 0.000 claims description 11
239000012453 solvate Substances 0.000 claims description 11
230000003449 preventive effect Effects 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
-1 acetamino group Chemical group 0.000 claims description 7
229940076279 serotonin Drugs 0.000 claims description 7
239000002111 antiemetic agent Substances 0.000 claims description 6
229940125683 antiemetic agent Drugs 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
DTRMFUAUYNIOEZ-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-6-methyl-1,3-benzoxazole Chemical compound N=1C=2C=C(Cl)C(C)=CC=2OC=1N1CCCNCC1 DTRMFUAUYNIOEZ-UHFFFAOYSA-N 0.000 claims description 4
UNRCLDQBGKUOMP-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-7-ethyl-1,3-benzoxazole Chemical compound O1C=2C(CC)=CC(Cl)=CC=2N=C1N1CCCNCC1 UNRCLDQBGKUOMP-UHFFFAOYSA-N 0.000 claims description 4
YZVOXCBEYYKZNK-UHFFFAOYSA-N [5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]methanol Chemical compound O1C=2C(CO)=CC(Cl)=CC=2N=C1N1CCCNCC1 YZVOXCBEYYKZNK-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
230000036961 partial effect Effects 0.000 claims description 4
LOYJLGODJCVFLT-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-amine Chemical compound O1C=2C(N)=CC(Cl)=CC=2N=C1N1CCCNCC1 LOYJLGODJCVFLT-UHFFFAOYSA-N 0.000 claims description 3
BBENGKGAKVSDCZ-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-6,7-dimethyl-1,3-benzoxazole Chemical compound O1C2=C(C)C(C)=C(Cl)C=C2N=C1N1CCCNCC1 BBENGKGAKVSDCZ-UHFFFAOYSA-N 0.000 claims description 3
ZCXNEHHRRBCEPK-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-n-ethyl-1,3-benzoxazol-7-amine Chemical compound O1C=2C(NCC)=CC(Cl)=CC=2N=C1N1CCCNCC1 ZCXNEHHRRBCEPK-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
PBIFALKTLDJESI-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]-2-methylpropanamide Chemical compound O1C=2C(NC(=O)C(C)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 PBIFALKTLDJESI-UHFFFAOYSA-N 0.000 claims description 3
XJVYTYQRSXAPDS-UHFFFAOYSA-N 5,7-dichloro-2-(1,4-diazepan-1-yl)-6-methyl-1,3-benzoxazole Chemical compound O1C2=C(Cl)C(C)=C(Cl)C=C2N=C1N1CCCNCC1 XJVYTYQRSXAPDS-UHFFFAOYSA-N 0.000 claims description 2
239000012190 activator Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
VLXAVBHLFBHNEA-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]acetamide Chemical compound O1C=2C(NC(=O)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 VLXAVBHLFBHNEA-UHFFFAOYSA-N 0.000 claims description 2
XBEWYQHJENXEIF-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]methanesulfonamide Chemical compound O1C=2C(NS(=O)(=O)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 XBEWYQHJENXEIF-UHFFFAOYSA-N 0.000 claims description 2
SPXDKQKOIXXWNW-UHFFFAOYSA-N n-benzyl-5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-amine Chemical compound C=12OC(N3CCNCCC3)=NC2=CC(Cl)=CC=1NCC1=CC=CC=C1 SPXDKQKOIXXWNW-UHFFFAOYSA-N 0.000 claims description 2
IWWLKUZVMOTTFP-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]carbamate Chemical compound O1C=2C(NC(=O)OC(C)(C)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 IWWLKUZVMOTTFP-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
MOPZJYDOQRNABV-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]benzamide Chemical compound C=12OC(N3CCNCCC3)=NC2=CC(Cl)=CC=1NC(=O)C1=CC=CC=C1 MOPZJYDOQRNABV-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 description 12
230000003213 activating effect Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
208000035475 disorder Diseases 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000004677 hydrates Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
206010010774 Constipation Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000013872 defecation Effects 0.000 description 3
201000010099 disease Diseases 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
229940044551 receptor antagonist Drugs 0.000 description 3
239000002464 receptor antagonist Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
AHPVBWOWLNLLQH-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-7-methoxy-1,3-benzoxazole Chemical compound O1C=2C(OC)=CC(Cl)=CC=2N=C1N1CCCNCC1 AHPVBWOWLNLLQH-UHFFFAOYSA-N 0.000 description 2
QPKABSXJDCZNKQ-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-7-methyl-1,3-benzoxazole Chemical compound O1C=2C(C)=CC(Cl)=CC=2N=C1N1CCCNCC1 QPKABSXJDCZNKQ-UHFFFAOYSA-N 0.000 description 2
208000004998 Abdominal Pain Diseases 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
206010015137 Eructation Diseases 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
206010067715 Gastrointestinal sounds abnormal Diseases 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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241000124008 Mammalia Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 2
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239000003086 colorant Substances 0.000 description 2
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210000004185 liver Anatomy 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229960005343 ondansetron Drugs 0.000 description 2
210000004798 organs belonging to the digestive system Anatomy 0.000 description 2
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238000001959 radiotherapy Methods 0.000 description 2
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QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
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LLNAKLUSLHVEMV-UHFFFAOYSA-N 5-chloro-7-methoxy-3h-1,3-benzoxazole-2-thione Chemical compound COC1=CC(Cl)=CC2=C1OC(S)=N2 LLNAKLUSLHVEMV-UHFFFAOYSA-N 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

ZA200104620A 1998-11-20 2001-06-06 Benzoxazole derivatives and medicaments comprising said derivatives as active ingredient. ZA200104620B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP33127498		1998-11-20

Publications (1)

Publication Number	Publication Date
ZA200104620B true ZA200104620B (en)	2002-02-04

Family

ID=18241866

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200104620A ZA200104620B (en)	1998-11-20	2001-06-06	Benzoxazole derivatives and medicaments comprising said derivatives as active ingredient.

Country Status (23)

Country	Link
US (1)	US7045516B1 (ru)
EP (1)	EP1134220B1 (ru)
JP (1)	JP4557112B2 (ru)
KR (1)	KR100675033B1 (ru)
CN (1)	CN1333771A (ru)
AT (1)	ATE273974T1 (ru)
AU (1)	AU753797B2 (ru)
BR (1)	BR9916793A (ru)
CA (1)	CA2351446A1 (ru)
CZ (1)	CZ20011700A3 (ru)
DE (1)	DE69919575T2 (ru)
ES (1)	ES2222763T3 (ru)
HU (1)	HUP0104238A3 (ru)
ID (1)	ID30143A (ru)
IL (1)	IL143178A0 (ru)
NO (1)	NO20012443L (ru)
PL (1)	PL348426A1 (ru)
RU (1)	RU2204558C2 (ru)
SK (1)	SK6772001A3 (ru)
TR (1)	TR200101945T2 (ru)
TW (1)	TW520370B (ru)
WO (1)	WO2000031073A1 (ru)
ZA (1)	ZA200104620B (ru)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6660858B2 (en) *	2001-03-28	2003-12-09	Lion Bioscience Ag	2-aminobenzoxazole derivatives and combinatorial libraries thereof
GB0203061D0 (en) *	2002-02-08	2002-03-27	Novartis Ag	Organic compounds
JP4399862B2 (ja) *	2002-08-09	2010-01-20	味の素株式会社	腸疾患および内臓痛の治療薬
EP1906951A4 (en) *	2005-07-01	2009-05-27	Dynogen Pharmaceuticals Inc	COMPOSITIONS AND METHODS FOR TREATING HYPOMOTILITY OF THE DIGESTIVE SYSTEM AND RELATED DISORDERS
JP2009531376A (ja)	2006-03-28	2009-09-03	ハイポイントファーマシューティカルズ，リミティドライアビリティカンパニー	ヒスタミンｈ３受容体活性を有するベンゾチアゾール
US8178666B2 (en) *	2008-10-23	2012-05-15	Albany Molecular Research, Inc.	2-aminobenzoxazole process
KR101579688B1 (ko)	2014-07-08	2015-12-24	재단법인 전남생물산업진흥원	좁쌀풀 추출물을 유효성분으로 함유하는 과민성 대장증후군에 의한 내장 통증 억제예방 또는 치료용 약학 조성물
CA3182245A1 (en) *	2020-06-12	2021-12-16	Jae Hee Cheon	Pharmaceutical composition comprising benzimidazole derivative compound

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JP3193560B2 (ja) *	1993-04-16	2001-07-30	明治製菓株式会社	新規ベンゾオキサゾール誘導体
JP3520177B2 (ja) *	1996-05-09	2004-04-19	明治製菓株式会社	セロトニン５−ｈｔ３受容体部分活性薬

1999
- 1999-11-18 TW TW088120112A patent/TW520370B/zh active
- 1999-11-19 RU RU2001116715/04A patent/RU2204558C2/ru not_active IP Right Cessation
- 1999-11-19 ID IDW00200101321A patent/ID30143A/id unknown
- 1999-11-19 AT AT99972633T patent/ATE273974T1/de not_active IP Right Cessation
- 1999-11-19 BR BR9916793-0A patent/BR9916793A/pt not_active IP Right Cessation
- 1999-11-19 EP EP99972633A patent/EP1134220B1/en not_active Expired - Lifetime
- 1999-11-19 US US09/856,372 patent/US7045516B1/en not_active Expired - Fee Related
- 1999-11-19 SK SK677-2001A patent/SK6772001A3/sk unknown
- 1999-11-19 WO PCT/JP1999/006491 patent/WO2000031073A1/ja active IP Right Grant
- 1999-11-19 AU AU11850/00A patent/AU753797B2/en not_active Ceased
- 1999-11-19 HU HU0104238A patent/HUP0104238A3/hu unknown
- 1999-11-19 JP JP2000583901A patent/JP4557112B2/ja not_active Expired - Fee Related
- 1999-11-19 KR KR1020017006249A patent/KR100675033B1/ko not_active IP Right Cessation
- 1999-11-19 DE DE69919575T patent/DE69919575T2/de not_active Expired - Lifetime
- 1999-11-19 PL PL99348426A patent/PL348426A1/xx unknown
- 1999-11-19 TR TR2001/01945T patent/TR200101945T2/xx unknown
- 1999-11-19 ES ES99972633T patent/ES2222763T3/es not_active Expired - Lifetime
- 1999-11-19 CZ CZ20011700A patent/CZ20011700A3/cs unknown
- 1999-11-19 IL IL14317899A patent/IL143178A0/xx unknown
- 1999-11-19 CN CN99815777A patent/CN1333771A/zh active Pending
- 1999-11-19 CA CA002351446A patent/CA2351446A1/en not_active Abandoned
2001
- 2001-05-18 NO NO20012443A patent/NO20012443L/no not_active Application Discontinuation
- 2001-06-06 ZA ZA200104620A patent/ZA200104620B/en unknown

Also Published As

Publication number	Publication date
RU2204558C2 (ru)	2003-05-20
TW520370B (en)	2003-02-11
TR200101945T2 (tr)	2001-11-21
PL348426A1 (en)	2002-05-20
DE69919575T2 (de)	2005-09-29
NO20012443L (no)	2001-07-12
KR100675033B1 (ko)	2007-01-29
CZ20011700A3 (cs)	2001-10-17
HUP0104238A3 (en)	2003-05-28
JP4557112B2 (ja)	2010-10-06
HUP0104238A2 (en)	2002-08-28
EP1134220A1 (en)	2001-09-19
ID30143A (id)	2001-11-08
CN1333771A (zh)	2002-01-30
NO20012443D0 (no)	2001-05-18
SK6772001A3 (en)	2001-12-03
BR9916793A (pt)	2001-11-13
US7045516B1 (en)	2006-05-16
KR20010086448A (ko)	2001-09-12
ES2222763T3 (es)	2005-02-01
CA2351446A1 (en)	2000-06-02
WO2000031073A1 (fr)	2000-06-02
IL143178A0 (en)	2002-04-21
EP1134220A4 (en)	2001-12-19
EP1134220B1 (en)	2004-08-18
AU753797B2 (en)	2002-10-31
DE69919575D1 (de)	2004-09-23
AU1185000A (en)	2000-06-13
ATE273974T1 (de)	2004-09-15

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