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CO4950608A1 - NEW DERIVATIVES OF PIPERAZINE AND PROCESSES FOR ITS PREPARATION - Google Patents

NEW DERIVATIVES OF PIPERAZINE AND PROCESSES FOR ITS PREPARATION

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Publication number
CO4950608A1
CO4950608A1 CO98021149A CO98021149A CO4950608A1 CO 4950608 A1 CO4950608 A1 CO 4950608A1 CO 98021149 A CO98021149 A CO 98021149A CO 98021149 A CO98021149 A CO 98021149A CO 4950608 A1 CO4950608 A1 CO 4950608A1
Authority
CO
Colombia
Prior art keywords
alkyl
nitrogen
oxygen
alkoxy
sulfur
Prior art date
Application number
CO98021149A
Other languages
Spanish (es)
Inventor
Kantilal Rami Harshad
Paul Adrian Wyman
Original Assignee
Smithkline Beecham Plc
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.)
Filing date
Publication date
Priority claimed from GBGB9707829.9A external-priority patent/GB9707829D0/en
Priority claimed from GBGB9801882.3A external-priority patent/GB9801882D0/en
Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc
Publication of CO4950608A1 publication Critical patent/CO4950608A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/08Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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 chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/12Heterocyclic 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 chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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 linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • 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)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto de la fórmula (I) o una de sus salesen la que Ra es un grupo de la fórmula (i)en la que P1 es fenilo, arilo bicíclico, un anillo heterocíclico de 5 a 7 miembros que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre, o un anillo heterocíclico bicíclico que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre;R1 es hidrógeno, halógeno, alquilo C1-6 , cicloalquilo C3-6 , CO-alquilo C1-6 , alcoxi C1-6 , hidroxi, hidroxi-alquilo C1-6 , hidroxi-alcoxi C1-6 , alcoxi C1-6 -alcoxi C1-6 , alcanoilo C1-6 , nitro,trifluorometilo, ciano, SR9 , SOR9 , SO2 R9 , SO2 NR10 R11 , CO2 R10 , CONR10 R11 , CO2 NR10 R11 , CONR10 (CH2 )a CO2 R11 , (CH2 )a NR10 R11 ,(CH2 )a CONR10 R11 , (CH2 )a NR10 CONR11 , (CH2 )2 CO2 -alquilo C1-6 , CO2 (CH2 )a OR10 , NR10 R11 , NR10 CO2 R11 , NR10 CONR10 R11 , CR10 =NOR11 , NR10 COOR11 , CNR10 =NOR11 , donde R10 y R11 son independientemente hidrógeno o alquilo C1-6 y C es 1 a 4,R2 es hidrógeno, halógeno, alquilo C1-6 , cicloalquilo C3-6 , cicloalquenilo C3-6 , alcoxi C1-6 , alcanoilo C1-6 , arilo, aciloxi, hidroxi, nitro, trifluorometilo, ciano, CO2 R10 , CONR10 R11 , NR10 R11 , donde R10 y R11 son como se han definido para R1 ;a es 1, 2 ó 3; - 2 -o Ra es un grupo de la fórmula (ii)en la que P2 y P3 son independientemente fenilo, arilo bicíclico, un anillo heterocíclico de 5 a 7 miembros que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno yazufre, o un grupo heterocíclico bicíclico que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno o azufre;A es un enlace u oxígeno, S(O)m donde m es 0 a 2, carbonilo, CH2 , -CH2 CH2 -, o NR4 donde R4 es hidrógeno o alquilo C1-6 ; R1 es como se ha definido antes para la fórmula (I) o R1 es un anillo heterocíclico de 5 a 7 miembros que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno o azufre, opcionalmentesustituido con alquilo C1-6 , halógeno o alcanoilo C1-6 . R2 y R3 son independientemente, hidrógeno, halógeno, alquilo C1-6 , cicloalquilo C3-6 , cicloalquenilo C3-6 , alcoxi C1-6 , alcanoilo C1-6 , arilo, aciloxi, hidroxi, nitro, trifluorometilo, ciano, CO2 R10 , CONR10 R11 , NR10 R11 , donde R10 y R11 son como se han definido para R1 ;y a y b son independientemente, 1, 2 ó 3;Y es -NH-, -NR5 - donde R5 es alquilo C1-6 , o Y es -CH2 - o -O-;V es oxígeno o azufre;D es nitrógeno, carbono o un grupo CH; W es (CR16 R17 )t donde t es 2, 3 ó 4 y R16 y R17 son independientemente hidrógeno o alquilo C1-6 , o W es (CR16 R17 )u AND#8209;J donde u es 0, 1, 2 ó 3 y J es oxígeno, azufre, CR16 =CR17 , CR16 =N, =CR16 O, =CR16 S o =CR16 -N17 ;X es nitrógeno o carbono;Rb es hidrógeno, halógeno, hidroxi, alquilo C1-6 , trifluorometilo, alcoxi C1-6 , alquenilo C2-6 , cicloalquilo C3-7 , opcionalmente sustituido con alquilo C1-4 , o arilo;Ra es hidrógeno o alquilo C1-6 ; y--- es un enlace sencillo cuando X es nitrógeno o un enlace sencillo o doble cuando X es carbono.A compound of formula (I) or a salt thereof in which Ra is a group of formula (i) in which P1 is phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 selected heteroatoms between oxygen, nitrogen and sulfur, or a bicyclic heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur; R1 is hydrogen, halogen, C1-6 alkyl, C3-6 cycloalkyl, CO-C1-6 alkyl, alkoxy C1-6, hydroxy, hydroxy-C1-6 alkyl, hydroxy-C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkanoyl, nitro, trifluoromethyl, cyano, SR9, SOR9, SO2 R9, SO2 NR10 R11, CO2 R10, CONR10 R11, CO2 NR10 R11, CONR10 (CH2) to CO2 R11, (CH2) to NR10 R11, (CH2) to CONR10 R11, (CH2) to NR10 CONR11, (CH2) 2 CO2-C1-alkyl 6, CO2 (CH2) to OR10, NR10 R11, NR10 CO2 R11, NR10 CONR10 R11, CR10 = NOR11, NR10 COOR11, CNR10 = NOR11, where R10 and R11 are independently hydrogen or C1-6 alkyl and C is 1 to 4, R2 is hydrogen, has logen, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 alkoxy, C1-6 alkanoyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2 R10, CONR10 R11, NR10 R11, where R10 and R11 are as defined for R1: a is 1, 2 or 3; - 2 -o Ra is a group of formula (ii) in which P2 and P3 are independently phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, or a bicyclic heterocyclic group containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur; A is a bond or oxygen, S (O) m where m is 0 to 2, carbonyl, CH2, -CH2 CH2 -, or NR4 where R4 is hydrogen or C1-6 alkyl; R1 is as defined above for formula (I) or R1 is a 5-7 membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur, optionally substituted with C1-6 alkyl, halogen or C1- alkanoyl 6. R2 and R3 are independently hydrogen, halogen, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 alkoxy, C1-6 alkanoyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2 R10, CONR10 R11, NR10 R11, where R10 and R11 are as defined for R1; y and b are independently, 1, 2 or 3; Y is -NH-, -NR5 - where R5 is C1-6 alkyl, or Y is -CH2 - or -O-; V is oxygen or sulfur; D is nitrogen, carbon or a CH group; W is (CR16 R17) t where t is 2, 3 or 4 and R16 and R17 are independently hydrogen or C1-6 alkyl, or W is (CR16 R17) or AND # 8209; J where u is 0, 1, 2 or 3 and J is oxygen, sulfur, CR16 = CR17, CR16 = N, = CR16 O, = CR16 S or = CR16 -N17; X is nitrogen or carbon; Rb is hydrogen, halogen, hydroxy, C1-6 alkyl, trifluoromethyl, C1-6 alkoxy, C2-6 alkenyl, C3-7 cycloalkyl, optionally substituted with C1-4alkyl, or aryl: Ra is hydrogen or C1-6alkyl; and --- is a single bond when X is nitrogen or a single or double bond when X is carbon.

CO98021149A 1997-04-18 1998-04-17 NEW DERIVATIVES OF PIPERAZINE AND PROCESSES FOR ITS PREPARATION CO4950608A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9707829.9A GB9707829D0 (en) 1997-04-18 1997-04-18 Novel compounds
GBGB9801882.3A GB9801882D0 (en) 1998-01-29 1998-01-29 Novel compounds

Publications (1)

Publication Number Publication Date
CO4950608A1 true CO4950608A1 (en) 2000-09-01

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Country Status (17)

Country Link
EP (1) EP0975593A1 (en)
JP (1) JP2001524116A (en)
KR (1) KR20010006487A (en)
CN (1) CN1260781A (en)
AR (1) AR013076A1 (en)
AU (1) AU732863B2 (en)
BR (1) BR9809092A (en)
CA (1) CA2288662A1 (en)
CO (1) CO4950608A1 (en)
HU (1) HUP0001123A3 (en)
IL (1) IL132409A0 (en)
NO (1) NO995065D0 (en)
NZ (1) NZ500252A (en)
PL (1) PL336317A1 (en)
TR (1) TR199902590T2 (en)
TW (1) TW509687B (en)
WO (1) WO1998050358A1 (en)

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GB9725931D0 (en) * 1997-12-05 1998-02-04 Smithkline Beecham Plc Novel compounds
US6342516B1 (en) 1998-07-31 2002-01-29 Nippon Soda Co., Ltd. Phenylazole compounds, process for producing the same and drugs for hyperlipemia
GB9827882D0 (en) * 1998-12-17 1999-02-10 Smithkline Beecham Plc Novel compounds
UA62015C2 (en) * 1998-12-28 2003-12-15 Pfizer Prod Inc Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants)
GB9912413D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912417D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
WO2001005758A2 (en) * 1999-07-15 2001-01-25 Nps Allelix Corp. Indoles and indazoles for the treatment of migraine
EP1216239B1 (en) 1999-09-25 2004-02-11 SmithKline Beecham plc Piperazine derivatives as 5-ht1b antagonists
GB9926303D0 (en) * 1999-11-05 2000-01-12 Smithkline Beecham Plc Novel compounds
EP1228043B1 (en) * 1999-11-05 2005-01-12 SmithKline Beecham plc Isoquinoline and quinazoline deivatives having a combined 5ht1a, 5ht1b and 5ht1d receptor activity
DE10051981A1 (en) 2000-10-20 2002-05-02 Bayer Ag Substituted phenyluracile
GB0106419D0 (en) * 2001-03-15 2001-05-02 Smithkline Beecham Plc Novel compounds
GB0106586D0 (en) * 2001-03-16 2001-05-09 Smithkline Beecham Plc Novel compounds
YU96103A (en) * 2001-06-07 2006-08-17 F.Hoffmann-La Roche Ag. New indole derivatives with 5-ht6 receptor affinity
DE60325025D1 (en) 2002-02-15 2009-01-15 Glaxo Group Ltd MODULATORS OF THE VANILLOID RECEPTOR
CA2485136C (en) 2002-05-13 2011-12-20 F. Hoffmann-La Roche Ag Benzoxazine derivatives as 5-ht6 modulators and uses thereof
WO2005058847A1 (en) 2003-12-09 2005-06-30 F. Hoffmann-La Roche Ag Benzoxazine derivatives and uses thereof
US20110166132A1 (en) * 2007-12-13 2011-07-07 Amgen Inc. Gamma Secretase Modulators
CA2794153C (en) 2010-03-25 2018-01-02 Glaxosmithkline Llc Substituted indoline derivatives as perk inhibitors
GB201106817D0 (en) 2011-04-21 2011-06-01 Astex Therapeutics Ltd New compound
CN102924330A (en) * 2012-09-03 2013-02-13 华东理工大学 Method for large-scale preparation of 5-amino-1-naphthyl nitrile
US9980973B2 (en) 2012-10-19 2018-05-29 Astex Therapeutics Limited Bicyclic heterocycle compounds and their uses in therapy
GB201218850D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
GB201218862D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
GB201218864D0 (en) 2012-10-19 2012-12-05 Astex Therapeutics Ltd Bicyclic heterocycle compounds and their uses in therapy
CN103467374A (en) * 2013-08-30 2013-12-25 江苏弘和药物研发有限公司 Synthesis method of 8-bromine-4-carboxyl quinoline
CN105829310B (en) 2013-12-20 2019-04-12 阿斯特克斯治疗有限公司 Bicyclic Heterocyclic Compounds and Their Therapeutic Uses
JP6693107B2 (en) * 2015-12-04 2020-05-13 東ソー株式会社 Method for purifying lutidine compound
CN115197099A (en) * 2022-05-30 2022-10-18 安徽昊帆生物有限公司 Preparation method of N-Boc-1,4-phenylenediamine

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GB9119932D0 (en) * 1991-09-18 1991-10-30 Glaxo Group Ltd Chemical compounds
GB9119920D0 (en) * 1991-09-18 1991-10-30 Glaxo Group Ltd Chemical compounds
DE69232003T2 (en) * 1991-09-18 2002-04-25 Glaxo Group Ltd., Greenford Benzanilide derivatives as 5-HT1D antagonists
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WO1995006637A1 (en) * 1993-09-03 1995-03-09 Smithkline Beecham Plc Indole and indoline derivatives as 5ht1d receptor antagonists

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HUP0001123A3 (en) 2002-04-29
CN1260781A (en) 2000-07-19
KR20010006487A (en) 2001-01-26
HUP0001123A2 (en) 2001-04-28
BR9809092A (en) 2002-01-22
NZ500252A (en) 2001-07-27
TR199902590T2 (en) 2000-06-21
WO1998050358A1 (en) 1998-11-12
IL132409A0 (en) 2001-03-19
AU7431098A (en) 1998-11-27
NO995065L (en) 1999-10-15
TW509687B (en) 2002-11-11
EP0975593A1 (en) 2000-02-02
NO995065D0 (en) 1999-10-15
CA2288662A1 (en) 1998-11-12
AU732863B2 (en) 2001-05-03
JP2001524116A (en) 2001-11-27
PL336317A1 (en) 2000-06-19
AR013076A1 (en) 2000-12-13

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