FI94634B - Analogiförfarande för framställning antiprotozoiskt verkande 5,6-dihydro-2-(substituerad fenyl)-1,2,4-triazin-3,5(2H,4H)-dionderivat - Google Patents

Analogiförfarande för framställning antiprotozoiskt verkande 5,6-dihydro-2-(substituerad fenyl)-1,2,4-triazin-3,5(2H,4H)-dionderivat Download PDF

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Publication number
FI94634B
FI94634B FI870421A FI870421A FI94634B FI 94634 B FI94634 B FI 94634B FI 870421 A FI870421 A FI 870421A FI 870421 A FI870421 A FI 870421A FI 94634 B FI94634 B FI 94634B
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FI
Finland
Prior art keywords
formula
parts
chlorophenyl
dihydro
dioxo
Prior art date
Application number
FI870421A
Other languages
English (en)
Finnish (fi)
Other versions
FI94634C (sv
FI870421A0 (sv
FI870421A (sv
Inventor
Victor Sipido
Alfons Herman Marg Raeymaekers
Gustaaf Maria Boeckx
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Janssen Pharmaceutica Nv
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.)
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Publication date
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of FI870421A0 publication Critical patent/FI870421A0/sv
Publication of FI870421A publication Critical patent/FI870421A/sv
Priority to FI923914A priority Critical patent/FI923914A0/fi
Application granted granted Critical
Publication of FI94634B publication Critical patent/FI94634B/sv
Publication of FI94634C publication Critical patent/FI94634C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic 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 carbon chain containing aromatic rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Fodder In General (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Claims (3)

1. Analogiförfarande för framställning av antipro-tozoiskt verkande 5,6-dihydro-2-(substituerad fenyl)-5 1,2,4-triazin-3,5(2H,4H)-dionderivat med formeln I R2 O. R1 -. V—N-R4 10 ί Ψ 'n—' R> R5 väri
15 Ar är med halogen substituerad tienyl eller en grupp med formeln a R6 „ <!> väri R6 är väte, halogen eller metoxi; R är väte eller C^-alkyl; R1 är cyan eller en grupp med formeln -C(=0)-Y-R9, •25 väri R9 är väte, fenyl eller C^-alkyl och Y är O, NR10 eller en direkt bindning, och R10 är väte eller R9 och R10 tillsammans med den kväveatomen vid vilken de är bundna bildar en 4-(C1.4-alkyl)piperazinylgrupp; R2 och R3 betecknar bäda självständigt väte, halo-30 gen, Cj^-alkyl eller C^-alkoxi; R4 är väte, bensyl, C^-alkyl eller fenyl-C3.4-alke-nyl; och R5 är väte, C1.4-alkylkarbonyl eller fenylkarbonyl; samt farmaceutiskt godtagbara syraadditionssalter och me-.35 tali- eller aminsubstitutionssalter och stereokemiska iso- 94634 » 44 merer därav, kännetecknat därav, att man re-ducerar en mellanprodukt med formeln II R2 O 5 /=k Vnx-r4 R3 10 väri Ar, R, R1, R2, R3 ooh R4 betecknar samma som ovan, varvid erhälls en förening med formeln I-a R: 0. /=|=\ ^—N-R4
15 I )=° (I~3) R N-/ R3 H väri Ar, R, R1, R2, R3 och R4 betecknar samma som ovan, och därefter eventuellt N-alkylerar föreningen med formeln I-20 a med ett reagens med formeln III R5'a-W (III) väri W är en reaktiv avlägsnande grupp och R5'“ är C^-al-25 kylkarbonyl eller fenylkarbonyl, varvid erhälls en före-ning med formeln I-b R2 0. /=k VN,-R4 30 <!-·» K I, I R3 R5'1 väri Ar, R, R1, R2, R3, R4 och R5‘a betecknar samma som ovan, och eventuellt överför föreningar med formeln I tili var-35 andra genom överföringsreaktioner av funktionella grupper; 45 9 4 6 3 4 och, ifall önskvärt, överför föreningar med formeln I till terapeutiskt verkande, giftfria syraadditionssalter eller till metall- eller aminsubstitutionssalter genom behand-ling med en lämplig syra eller bas, eller omvänt, överför 5 ett syraadditionssalt eller metall- eller aminsubstitu- tionssalt till fri bas form med en bas eller syra; och/el-ler framställer stereokemiska isomerer därav.
2. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer 2,6-diklor-a-10 (4-klorfenyl )-4-(3,4,5,6-tetrahydro-3,5-dioxo-l, 2,4-tri- azin-2(1H)-yl)bensenacetonitril.
3. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer 2-klor-a-(4-klorfenyl)-4-(3,4,5,6-tetrahydro-3,5-dioxo-l,2,4-triazin-15 2(lH)-yl)bensenacetonitril.
FI870421A 1986-01-30 1987-01-30 Analogiförfarande för framställning antiprotozoiskt verkande 5,6-dihydro-2-(substituerad fenyl)-1,2,4-triazin-3,5(2H,4H)-dionderivat FI94634C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI923914A FI923914A0 (fi) 1986-01-30 1992-09-01 Foerfarande foer framstaellning av 2-(substituerad fenyl)-1,2,4-triazin-3,5(2h,4h)-dionderivat.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB868602342A GB8602342D0 (en) 1986-01-30 1986-01-30 5 6-dihydro-2-(substituted phenyl)-1 2 4-triazine-3 5(2h 4h)-diones
GB8602342 1986-01-30

Publications (4)

Publication Number Publication Date
FI870421A0 FI870421A0 (sv) 1987-01-30
FI870421A FI870421A (sv) 1987-07-31
FI94634B true FI94634B (sv) 1995-06-30
FI94634C FI94634C (sv) 1995-10-10

Family

ID=10592258

Family Applications (1)

Application Number Title Priority Date Filing Date
FI870421A FI94634C (sv) 1986-01-30 1987-01-30 Analogiförfarande för framställning antiprotozoiskt verkande 5,6-dihydro-2-(substituerad fenyl)-1,2,4-triazin-3,5(2H,4H)-dionderivat

Country Status (21)

Country Link
US (3) US4767760A (sv)
EP (1) EP0232932B1 (sv)
JP (2) JPH0813806B2 (sv)
CN (1) CN1017049B (sv)
AT (1) ATE59644T1 (sv)
AU (1) AU586731B2 (sv)
CA (2) CA1288772C (sv)
DE (1) DE3766839D1 (sv)
DK (2) DK169032B1 (sv)
ES (1) ES2031876T3 (sv)
FI (1) FI94634C (sv)
GB (1) GB8602342D0 (sv)
GR (1) GR3001392T3 (sv)
IE (1) IE59510B1 (sv)
IL (1) IL81421A (sv)
NO (1) NO172690C (sv)
NZ (1) NZ218973A (sv)
PT (1) PT84218B (sv)
RU (1) RU2017736C1 (sv)
SU (1) SU1595339A3 (sv)
ZA (1) ZA87672B (sv)

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US4097779A (en) * 1976-04-05 1978-06-27 Gte Sylvania Incorporated Fluorescent lamp containing a cathode heater circuit disconnect device
US4156831A (en) * 1978-05-24 1979-05-29 Gte Sylvania Incorporated Fluorescent lamp having heater circuit disconnect device
GB8602342D0 (en) * 1986-01-30 1986-03-05 Janssen Pharmaceutica Nv 5 6-dihydro-2-(substituted phenyl)-1 2 4-triazine-3 5(2h 4h)-diones
DE3826058A1 (de) * 1988-07-30 1990-02-08 Bayer Ag Mittel gegen fischparasiten
US5070091A (en) * 1989-01-09 1991-12-03 Bayer Aktiengesellschaft Substituted 1,2,4-triazinediones useful against protozoa in insects
EP0377903A3 (de) * 1989-01-09 1991-07-17 Bayer Ag Substituierte Hexahydro-1,2,4-triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung
CN1044905A (zh) * 1989-02-16 1990-08-29 赫彻斯特股份公司 鱼和昆虫寄生虫对抗剂
CA2012004A1 (en) * 1989-03-15 1990-09-15 Frank Ellis Chemical compounds
EP0476439A1 (de) * 1990-09-18 1992-03-25 Bayer Ag Substituierte 1,2,4-Triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung
DE4120138A1 (de) * 1991-06-19 1992-12-24 Bayer Ag Substituierte hexahydro-1,2,4-triazindione, verfahren zu ihrer herstellung, zwischenprodukte dafuer und ihre verwendung
US5994355A (en) * 1993-10-15 1999-11-30 Takeda Chemical Industries, Ltd. 1, 2, 4-Triazin-3-one derivatives, production and use thereof
EP0737672B1 (en) * 1995-04-14 2001-10-04 Takeda Schering-Plough Animal Health K.K. Method of producing triazine derivatives
US5747476A (en) * 1996-07-17 1998-05-05 Mortar & Pestle Veterinary Pharmacy, Inc. Treatment of equine protozoal myeloencephalitis
EP0831088B1 (en) * 1996-08-30 2002-11-27 Takeda Schering-Plough Animal Health K.K. 1,2,4-Triazine-3,5-dione derivatives as anticoccidial agents
WO1998043644A1 (en) * 1997-03-31 1998-10-08 David Granstrom Formulations and methods to treat and prevent equine protozoal myeloencephalitis
US5883095A (en) * 1997-08-07 1999-03-16 University Of Kentucky Research Foundation Formulations and methods to treat and prevent equine protozoal myeloencephalitis
US5830893A (en) * 1997-04-23 1998-11-03 Mortar & Pestle Veterinary Pharmacy, Inc. Treatment of equine protozoan myeloencephalitis using triazinediones
CA2294145A1 (en) * 1997-07-10 1999-01-21 Janssen Pharmaceutica N.V. Il-5 inhibiting 6-azauracil derivatives
US6867207B2 (en) 1997-07-10 2005-03-15 Janssen Pharmaceutica N.V. IL-5 inhibiting 6-azauracil derivatives
ID24224A (id) 1997-07-10 2000-07-13 Janssen Pharmaceutica Nv Turunan-turunan 6-azaurasil sebagai inhibitor il-5
US6294536B1 (en) 1997-08-29 2001-09-25 Takeda Schering-Plough Animal Health K.K. Triazine derivatives, their production and use
WO2000006172A1 (en) * 1998-07-27 2000-02-10 Mortar & Pestle Veterinary Pharmacy, Inc. Treatment of equine protozoan myeloencephalitis using triazinediones
EP0987265A1 (en) 1998-09-18 2000-03-22 Janssen Pharmaceutica N.V. Interleukin-5 inhibiting 6-azauracil derivatives
BR9914385A (pt) * 1998-10-08 2001-07-17 New Ace Res Company Composição útil para o tratamento e prevenção de infecções protozoárias no homem e em animais, e, método de tratamento de uma infecção protozoária no homem e em animais
WO2000037451A1 (en) * 1998-12-18 2000-06-29 Janssen Pharmaceutica N.V. Il-5 inhibiting 6-azauracil derivatives
HUP0202692A3 (en) 1999-08-06 2003-01-28 Janssen Pharmaceutica Nv Interleukin-5 inhibiting 6-azauracil derivatives, pharmaceutical compositions containing them and intermediates
PA8591801A1 (es) * 2002-12-31 2004-07-26 Pfizer Prod Inc Inhibidores benzamidicos del receptor p2x7.
GB0622472D0 (en) * 2006-11-10 2006-12-20 Addex Pharmaceuticals Sa Novel heterocyclic derivatives
CN107746390B (zh) * 2017-11-21 2021-03-16 连云港市亚晖医药化工有限公司 抗球虫药地克珠利的制备方法
CN113999139A (zh) * 2021-12-03 2022-02-01 杭州臻峰科技有限公司 制备2，6-二氯-α-（4-氯代苯基） -4-硝基苯乙腈的方法

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Also Published As

Publication number Publication date
FI94634C (sv) 1995-10-10
US4912106A (en) 1990-03-27
IE59510B1 (en) 1994-03-09
JPH0813806B2 (ja) 1996-02-14
US4767760A (en) 1988-08-30
AU586731B2 (en) 1989-07-20
IE870231L (en) 1987-07-30
CA1288772C (en) 1991-09-10
GR3001392T3 (en) 1992-09-11
NO870378D0 (no) 1987-01-29
CN87100531A (zh) 1987-09-02
DK169032B1 (da) 1994-08-01
DK48187A (da) 1987-07-31
NO172690B (no) 1993-05-18
GB8602342D0 (en) 1986-03-05
US4952570A (en) 1990-08-28
FI870421A0 (sv) 1987-01-30
CN1017049B (zh) 1992-06-17
DE3766839D1 (de) 1991-02-07
DK65193A (da) 1993-06-04
DK48187D0 (da) 1987-01-29
JPS62190174A (ja) 1987-08-20
SU1595339A3 (ru) 1990-09-23
PT84218A (en) 1987-02-01
CA1302411C (en) 1992-06-02
ES2031876T3 (es) 1993-01-01
PT84218B (pt) 1989-07-31
ATE59644T1 (de) 1991-01-15
EP0232932B1 (en) 1991-01-02
IL81421A0 (en) 1987-08-31
JPH07285949A (ja) 1995-10-31
IL81421A (en) 1991-11-21
JP2622510B2 (ja) 1997-06-18
NO870378L (no) 1987-07-31
NZ218973A (en) 1988-10-28
FI870421A (sv) 1987-07-31
EP0232932A1 (en) 1987-08-19
RU2017736C1 (ru) 1994-08-15
ZA87672B (en) 1988-09-28
AU6813487A (en) 1987-08-06
DK65193D0 (da) 1993-06-04
NO172690C (no) 1993-08-25

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Owner name: JANSSEN PHARMACEUTICA N.V.