ZA200201085B - Benzofurane derivatives. - Google Patents

Benzofurane derivatives. Download PDF

Info

Publication number: ZA200201085B
Authority: ZA; South Africa
Prior art keywords: formula; compound; ylcarbonyl; piperazinyl; protective group
Prior art date: 1999-07-10

Application number

ZA200201085A

Other languages

English (en)

Inventor

Andreas Bathe

Henning Boettcher

Bernd Helfert

Original Assignee

Merck Patent Gmbh

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.)

1999-07-10

Filing date

2002-02-07

Publication date

2003-07-30

2002-02-07 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2003-07-30 Publication of ZA200201085B publication Critical patent/ZA200201085B/en

Links

IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical class C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 77
-1 N,N-di (tert- butyloxycarbonyl) aminocarbonyl Chemical group 0.000 claims description 39
125000006239 protecting group Chemical group 0.000 claims description 31
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 7
238000003786 synthesis reaction Methods 0.000 claims description 7
150000001907 coumarones Chemical class 0.000 claims description 6
239000000543 intermediate Substances 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
SGEGOXDYSFKCPT-UHFFFAOYSA-N vilazodone Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)N)=CNC2=C1 SGEGOXDYSFKCPT-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
LLRGOAFFRRUFBM-UHFFFAOYSA-N 5-piperazin-1-yl-1-benzofuran-2-carboxamide Chemical compound C=1C=C2OC(C(=O)N)=CC2=CC=1N1CCNCC1 LLRGOAFFRRUFBM-UHFFFAOYSA-N 0.000 claims 2
229910021529 ammonia Inorganic materials 0.000 claims 2
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 2
DLTSJQJIAIARAP-UHFFFAOYSA-N (5-bromo-1-benzofuran-2-yl)-(2,5-dimethyl-1h-pyrrol-3-yl)methanone Chemical compound N1C(C)=CC(C(=O)C=2OC3=CC=C(Br)C=C3C=2)=C1C DLTSJQJIAIARAP-UHFFFAOYSA-N 0.000 claims 1
WXYNQUJKZDOQAQ-UHFFFAOYSA-N 2h-oxazine-3-carbaldehyde Chemical compound O=CC1=CC=CON1 WXYNQUJKZDOQAQ-UHFFFAOYSA-N 0.000 claims 1
FRQIRDOLVIYPNU-UHFFFAOYSA-N 5-bromo-2-(2-methylprop-1-enyl)-1-benzofuran Chemical compound BrC1=CC=C2OC(C=C(C)C)=CC2=C1 FRQIRDOLVIYPNU-UHFFFAOYSA-N 0.000 claims 1
YPNCNPPGAQYNSR-UHFFFAOYSA-N [5-(4-benzylpiperazin-1-yl)-1-benzofuran-2-yl]-(3,4-dihydro-1h-phthalazin-2-yl)methanone Chemical compound C1C2=CC=CC=C2CNN1C(=O)C(OC1=CC=2)=CC1=CC=2N(CC1)CCN1CC1=CC=CC=C1 YPNCNPPGAQYNSR-UHFFFAOYSA-N 0.000 claims 1
238000006555 catalytic reaction Methods 0.000 claims 1
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
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150000001408 amides Chemical class 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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 2
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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125000001931 aliphatic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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150000002170 ethers Chemical class 0.000 description 2
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238000011065 in-situ storage Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229960002415 trichloroethylene Drugs 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200201085A 1999-07-10 2002-02-07 Benzofurane derivatives. ZA200201085B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19932314A DE19932314A1 (de)	1999-07-10	1999-07-10	Benzofuranderivate

Publications (1)

Publication Number	Publication Date
ZA200201085B true ZA200201085B (en)	2003-07-30

Family

ID=7914351

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200201085A ZA200201085B (en)	1999-07-10	2002-02-07	Benzofurane derivatives.

Country Status (29)

Country	Link
US (1)	US6531503B1 (zh)
EP (1)	EP1194426B1 (zh)
JP (1)	JP4908706B2 (zh)
KR (1)	KR100709378B1 (zh)
CN (1)	CN1178934C (zh)
AR (1)	AR024671A1 (zh)
AT (1)	ATE273973T1 (zh)
AU (1)	AU767413B2 (zh)
BR (1)	BRPI0012329B8 (zh)
CA (1)	CA2378603C (zh)
CZ (1)	CZ301441B6 (zh)
DE (2)	DE19932314A1 (zh)
DK (1)	DK1194426T3 (zh)
ES (1)	ES2226884T3 (zh)
HK (1)	HK1047275B (zh)
HU (1)	HU229135B1 (zh)
IL (2)	IL147494A0 (zh)
MX (1)	MXPA02000316A (zh)
MY (1)	MY122667A (zh)
NO (1)	NO328209B1 (zh)
PL (1)	PL196477B1 (zh)
PT (1)	PT1194426E (zh)
RU (1)	RU2278862C2 (zh)
SI (1)	SI1194426T1 (zh)
SK (1)	SK287360B6 (zh)
TR (1)	TR200200017T2 (zh)
UA (1)	UA73310C2 (zh)
WO (1)	WO2001004112A2 (zh)
ZA (1)	ZA200201085B (zh)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102006060597A1 (de) *	2006-12-21	2008-06-26	Merck Patent Gmbh	Verfahren zur Herstellung von Benzofuran-2-carboxamiden
EP2110374A1 (en) *	2008-04-18	2009-10-21	Merck Sante	Benzofurane, benzothiophene, benzothiazol derivatives as FXR modulators
NZ594847A (en) *	2009-03-10	2013-10-25	Takeda Pharmaceutical	Benzofuran derivatives
CA2798610A1 (en)	2010-05-06	2011-11-10	Bristol-Myers Squibb Company	Bicyclic heteroaryl compounds as gpr119 modulators
US8729084B2 (en)	2010-05-06	2014-05-20	Bristol-Myers Squibb Company	Benzofuranyl analogues as GPR119 modulators
CN102964323B (zh) *	2012-11-13	2015-03-25	苏州永健生物医药有限公司	一种5-（哌嗪-1-基）苯并呋喃-2-甲酰胺的合成方法
EA028545B1 (ru) *	2013-06-10	2017-11-30	Астеллас Фарма Инк.	Бициклическое азотсодержащее ароматическое гетероциклическое амидное соединение

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2724915A (en) *		1955-11-29		Snow remover
DE2757532A1 (de)	1977-12-23	1979-07-05	Hoechst Ag	N,n'-disubstituiertes cyclisches diamin und verfahren zu dessen herstellung
CA2164009A1 (en)	1993-06-14	1994-12-22	Robert L. Dow	Secondary amines as antidiabetic and antiobesity agents
DE4333254A1 (de) *	1993-09-30	1995-04-06	Merck Patent Gmbh	Piperidine und Piperazine
DE19514567A1 (de) *	1995-04-20	1996-10-24	Merck Patent Gmbh	Benzofurane

1999
- 1999-07-10 DE DE19932314A patent/DE19932314A1/de not_active Withdrawn
2000
- 2000-06-29 TR TR2002/00017T patent/TR200200017T2/xx unknown
- 2000-06-29 HU HU0201903A patent/HU229135B1/hu not_active IP Right Cessation
- 2000-06-29 MX MXPA02000316A patent/MXPA02000316A/es active IP Right Grant
- 2000-06-29 CN CNB008093083A patent/CN1178934C/zh not_active Expired - Fee Related
- 2000-06-29 SI SI200030518T patent/SI1194426T1/xx unknown
- 2000-06-29 RU RU2002102234/04A patent/RU2278862C2/ru not_active IP Right Cessation
- 2000-06-29 PL PL353157A patent/PL196477B1/pl not_active IP Right Cessation
- 2000-06-29 AT AT00949229T patent/ATE273973T1/de active
- 2000-06-29 ES ES00949229T patent/ES2226884T3/es not_active Expired - Lifetime
- 2000-06-29 BR BRPI0012329A patent/BRPI0012329B8/pt not_active IP Right Cessation
- 2000-06-29 AU AU62665/00A patent/AU767413B2/en not_active Ceased
- 2000-06-29 US US10/030,471 patent/US6531503B1/en not_active Expired - Lifetime
- 2000-06-29 KR KR1020017015565A patent/KR100709378B1/ko not_active IP Right Cessation
- 2000-06-29 DK DK00949229T patent/DK1194426T3/da active
- 2000-06-29 CZ CZ20020011A patent/CZ301441B6/cs not_active IP Right Cessation
- 2000-06-29 JP JP2001509722A patent/JP4908706B2/ja not_active Expired - Fee Related
- 2000-06-29 PT PT00949229T patent/PT1194426E/pt unknown
- 2000-06-29 EP EP00949229A patent/EP1194426B1/de not_active Expired - Lifetime
- 2000-06-29 WO PCT/EP2000/006089 patent/WO2001004112A2/de active IP Right Grant
- 2000-06-29 SK SK6-2002A patent/SK287360B6/sk not_active IP Right Cessation
- 2000-06-29 IL IL14749400A patent/IL147494A0/xx active IP Right Grant
- 2000-06-29 CA CA2378603A patent/CA2378603C/en not_active Expired - Fee Related
- 2000-06-29 DE DE50007501T patent/DE50007501D1/de not_active Expired - Lifetime
- 2000-06-29 UA UA2002021055A patent/UA73310C2/uk unknown
- 2000-07-06 MY MYPI20003075A patent/MY122667A/en unknown
- 2000-07-07 AR ARP000103465A patent/AR024671A1/es active IP Right Grant
2002
- 2002-01-06 IL IL147494A patent/IL147494A/en not_active IP Right Cessation
- 2002-01-09 NO NO20020095A patent/NO328209B1/no not_active IP Right Cessation
- 2002-02-07 ZA ZA200201085A patent/ZA200201085B/en unknown
- 2002-11-29 HK HK02108676.2A patent/HK1047275B/zh unknown

Also Published As

Publication number	Publication date
BR0012329B1 (pt)	2013-03-19
HK1047275A1 (en)	2003-02-14
HUP0201903A2 (en)	2002-10-28
EP1194426B1 (de)	2004-08-18
WO2001004112A3 (de)	2001-08-02
HK1047275B (zh)	2005-09-02
KR100709378B1 (ko)	2007-04-20
IL147494A0 (en)	2002-08-14
PT1194426E (pt)	2005-01-31
TR200200017T2 (tr)	2002-05-21
CN1356996A (zh)	2002-07-03
BR0012329A (pt)	2002-03-19
CA2378603A1 (en)	2001-01-18
RU2278862C2 (ru)	2006-06-27
CZ200211A3 (cs)	2002-04-17
MY122667A (en)	2006-04-29
PL353157A1 (en)	2003-10-20
IL147494A (en)	2008-03-20
ES2226884T3 (es)	2005-04-01
AR024671A1 (es)	2002-10-23
NO20020095D0 (no)	2002-01-09
SK287360B6 (sk)	2010-08-09
AU6266500A (en)	2001-01-30
WO2001004112A2 (de)	2001-01-18
DE50007501D1 (de)	2004-09-23
JP4908706B2 (ja)	2012-04-04
HU229135B1 (en)	2013-08-28
SI1194426T1 (en)	2005-02-28
ATE273973T1 (de)	2004-09-15
HUP0201903A3 (en)	2005-02-28
US6531503B1 (en)	2003-03-11
AU767413B2 (en)	2003-11-06
SK62002A3 (en)	2002-05-09
UA73310C2 (en)	2005-07-15
JP2003504364A (ja)	2003-02-04
PL196477B1 (pl)	2008-01-31
CZ301441B6 (cs)	2010-03-03
BRPI0012329B8 (pt)	2021-05-25
NO328209B1 (no)	2010-01-11
MXPA02000316A (es)	2002-07-30
DE19932314A1 (de)	2001-01-11
EP1194426A2 (de)	2002-04-10
CN1178934C (zh)	2004-12-08
DK1194426T3 (da)	2004-12-20
CA2378603C (en)	2010-05-11
NO20020095L (no)	2002-01-09
KR20020016815A (ko)	2002-03-06

Publication	Publication Date	Title
US5977112A (en)	1999-11-02	Process of making substituted benzofurans
Dal Piaz et al.	1996	4, 5-Functionalized 6-phenyl-3 (2H)-pyridazinones: synthesis and evaluation of antinociceptive activity
NZ516111A (en)	2003-05-30	Phenoxypropylamine compounds useful to treat depression
TWI679204B (zh)	2019-12-11	苯并惡唑并惡嗪酮類化合物的製備方法及其中間體和晶型
WO2005058858A1 (en)	2005-06-30	Novel benzofuran derivatives, which can be used in prophylaxis or treatment of 5-ht6 receptor-related disorder
AU2007316736A1 (en)	2008-05-15	Indole and benzofuran 2-carboxamide derivatives
ZA200201085B (en)	2003-07-30	Benzofurane derivatives.
US6646136B1 (en)	2003-11-11	Chroman derivatives
AU783355B2 (en)	2005-10-20	Method for producing 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination
US6812353B2 (en)	2004-11-02	Chromanone derivatives
CA2011834A1 (en)	1990-09-11	Indole derivatives
JP2017517576A (ja)	2017-06-29	キナゾリン誘導体作製方法
JP2014518230A (ja)	2014-07-28	置換されたフェニル化合物