LV10712B - 2-ciano-3-hydroxypropene amides - Google Patents

2-ciano-3-hydroxypropene amides Download PDF

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Publication number
LV10712B
LV10712B LVP-94-02A LV940002A LV10712B LV 10712 B LV10712 B LV 10712B LV 940002 A LV940002 A LV 940002A LV 10712 B LV10712 B LV 10712B
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group
formula
compound
cyclopropyl
cyano
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LVP-94-02A
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LV10712A (lv
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Kuo Elizabeth Anne
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Roussel Uclaf
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Publication of LV10712A publication Critical patent/LV10712A/lv
Publication of LV10712B publication Critical patent/LV10712B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (16)

  1. LV 10712 Izgudrojuma formula 1. Savienojumi ar formulu (I)
    Rj_ CN kurā: A, B un E katrs apzīmē =CH- grupu vai slāpekļa atomu, ar nosacījumu, ka vismaz viens no A, B un E apzīmē slāpekļa atomu; R apzīmē cikloalkilgrupu, kas satur 3-6 oglekļa atomus; alkenilgrupu, kas satur 2-6 oglekļa atomus, vai arī alkinilgrupu, kas satur 2-6 oglekļa atomus; R1 apzīmē ūdeņraža atomu vai alkilgrupu, kas satur 1-3 oglekļa atomus; R2 un R3 ir vienādi vai dažādi un katrs apzīmē ūdeņraža atomu vai halogēna atomu, nitrogrupu, ciāngrupu, lineāru vai sazarotu alkoksigrupu, kas satur 1-6 oglekļa atomus, lineāru vai sazarotu alkilgrupu, kas satur 1-6 oglekļa atomus, cikloalkilgrupu, kas satur 3-6 oglekļa atomus, lineāru vai sazarotu alkiltiogrupu, kas satur 1-6 oglekļa atomus, -CO-R4 grupu (kurā R4 apzīmē ūdeņraža atomu, lineāru vai sazarotu 1 alkilgrupu, kas satur 1-6 oglek(a atomus vai cikloalkilgrupu, kas satur 3-6 oglek|a atomus), vai arī aizvietotāju, kas ņemts no grupārn:-(CH2)mCX3, -0-(CH2)m-CX3, -S-(CH2)m-CX3, --0-(CH2)m-CX3 un -(CX2)mCX3 (kur m apzīmē 0,1, 2 vai 3 un X apzīmē halogēna atomu); vai arī R2 un R3 abi kopā apzīmē grupu -0-CH2-0-, un to sālis ar bāzēm.
  2. 2. Savienojumi pēc 1. punkta, kur: R ir cikiopropilgrupa vai grupa ar formulu:
    vai un A, B, E. R1, R2 un R3 nozīmes atbilst 1. punktā minētajām.
  3. 3. Savienojumi pēc 1. vai 2. punkta, kur: R1 apzīmē ūdeņraža atomu vai metilgrupu, un A, B, E. R, R2 un R3 nozīmes atbilst 1. punktā minētajām.
  4. 4. īi pēc jebkura no iepriekšējiem punktiem, kur: R1 apzīmē ūdeņraža atomu vai metilgrupu, un R2 un R3 ir vienādi vai dažādi un katrs apzīmē ūdeņraža atomu, hlora atomu vai broma atomu, nitrogrupu, ciāngrupu, metilgrupu, ciklopropilgrupu, metoksigrupu, metiltiogrupu, -CO-FC grupu (kurā Rr apzīmē ūdeņraža atomu, metilgrupu vai ciklopropilgrupu), vai arī aizvietotāju, kas ņemts no grupām: :-(CH2)mCF3, -0-(CH2)m-CF3, -S-(CH2)m-CF3, -0-(CH2)m-CF3 un •(pF2)mCF3 (kur m apzīmē 0,1, 2 vai 3); vai arī R2 un R3 abi kopā apzīmē grupu -0-CH2-0-; A, B un E nozīmes atbilst 1. punktā minētajām.
  5. 5. Savienojumi pēc jebkura no iepriekšējiem punktiem, kur: R apzīmē ciklopropilgrupu; R1 apzīmē ūdeņraža atomu vai metilgrupu; R2 un R3 ir vienādi vai dažādi un katrs apzīmē ūdeņraža atomu, hlora atomu vai broma atomu, nitrogrupu, metilgrupu vai trifluormetilgrupu; A, B un E nozīmes atbilst 1. punktā minētajām.
  6. 6. Savienojumi pēc jebkura no iepriekšējiem punktiem, kas ņemti no grupas, kurā ietverti: 2-ciān-3-ciklopropil-3-oksi-N-(2-hlorpirid-5-il)-2-propēnamīds; 2-ciān-3-ciklopropil-3-oksi-N-(4-metil-5-nitropirid-5-il)-2-propēnamīds; 2 LV 10712 2-ciān-3-ciKlopropil-3-oksi-N-(5-trifluormetilpirid-5-il)-2-propēnamīds; 2-ciān-3-ciklopropil-3-oksi'N-(5-hlorpirid-2-il)-2-propēnamīds; 2-ciān-3-ciklopropil-3-oksi-N-(5-brompirid-5-il)-2-propēnamTds; 2-ciān-3-ciklopropil-3-oksi-N-(5-nitropirid-5-il)-2-propēnamīds; 2-ciān-3-ciklopropil-3-oksi-N-(pirid-4-il)-2-propēnamīds; 2-ciān-3-ciklopropil-3-oksi-N-(3,5-dihlorpirid-2-il)-2-propēnamids un to sālis ar bāzēm.
  7. 7. Paņēmiens savienojuma ar formulu (I) pēc jebkura no punktiem 1 .-6. iegūšanai, kas ietver vai nu: a) savienojuma ar formulu (II)
    (kurā A, B, E, R1, R2 un R3 nozīmes atbilst 1. punktā minētajām) apstrādi ar nātrija hidridu Qa nepieciešams, katalizatora klātienē) un tālāku reakciju ar savienojumu, kura formula ir (III) R-CO-Hal (Īli) (kur Hal apzīmē halogēna atomu un R nozīmes atbilst 1. punktā minētajām); vai arī b) savienojuma ar formulu (II), kā augstāk minēts, reakciju ar savienojumu, kura formula ir (lllA) RA-CO-Hal (lllA) (kur Hal zpzīmē halogēna atomu un RA apzīmē iepriekš minēto grupu A, kurai pievienota aizsarggrupa), veidojot savienojumu ar formulu (lA)
    (kur Ra, A, B, E, R1, R2 un R3 nozīmes atbilst iepriekš minētajām), kuram tālāk nošķej aizsarggrupas, iegūstot savienojumu ar formulu (I), kurā R ir jau iepriekš minētās nozīmes. 3
  8. 8. Paņēmiens saskaņā ar 7. punktu, kas atšķiras ar to, ka reakciju starp savienojumu ar formulu (II) un nātrija hidrīdu veic bezūdens tetrahidrofurāna vai dihioretāna šķīdumā neobligātā imidazola kā katalizatora klātienē un tālāko apstrādi ar savienojumu, kura formula ir (III) vai (lllA) arī veic bezūdens tetrahidrofurāna vai dihioretāna šķīdumā pie istabas vai pazeminātas temperatūras.
  9. 9. Paņēmiens saskaņā ar 7. vai 8. punktu, kas atšķiras ar to, ka tajā gadījumā, kad RA ir grupa R, kurai pievienota aizsarggrupa, minētā aizsarggrupa ir arilselenogrupa, piemēram, fenilselenogrupa.
  10. 10. Paņēmiens savienojuma (I) pēc jebkura no punktiem 1.-6. iegūšanai, kad R ir cikloalkilgrupa ar 3-6 oglekļa atomiem, kas atšķiras ar to, ka savienojumu ar formulu (IV)
    (IV) (kur A, B, E, R1, R2 un R3 nozīmes atbilst 1.punktā minētajām, bet R nozīme ir iepriekš jau minētā), apstrādā ar stipru bāzi.
  11. 11. Paņēmiens saskaņā ar jebkuru iepriekšējo punktu no 7. līdz 10., kas atšķiras ar to, ka savienojumu ar formulu (II) pagatavo, apstrādājot savienojumu, kura formula ir (V)
    (V) (kur A. B, E, R1, R2 un R3 nozīmes atbilst 1. punktā minētajām) ar ciānetiķskābi, vēlams dicikloheksilkarbodiimīda vai fosfora pentahlorīda klātienē bezūdens tetrahidrofurāna vai dihlormetāna šķīdumā.
  12. 12. Paņēmiens saskaņā ar 10. punktu, kas atšķiras ar to, ka savienojumu ar formulu (IV) pagatavo apstrādājot savienojumu, kura formula ir (V), kāda tā dota 11. punktā, ar skābes hlorīdu, kura formula ir (VI) 4 LV 10712 Ο
    (VI) (kur R nozīmes atbilst 10. punktā minētajām).
  13. 13. Paņēmiens saskaņā ar jebkuru punktu no 7. līdz 12, kas atšķiras ar to, ka pēc tā iegūtais savienojumu ar formulu (I) tiek tālāk pārvērsts sālī ar bāzi, lietojot parastos paņēmienus, piemēram, apstrādājot savienojumu, kura formula ir (I), ar aptuveni ekvivalentu daudzumu neorganiskas vai organiskas bāzes.
  14. 14. Savienojuma pēc jebkura punkta no 1. līdz 6. vai 13., vai tā farmakoloģiski pieņemamas sāls pielietojums ārstniecībā par medikamentu reimatoīdā artrīta, imūnogēnu vai neimūnogēnu hronisko iekaisuma slimību un vēža ārstēšanai.
  15. 15. Farmaceitiskā kompozīcija r kas kā aktīvo vielu satur vismaz vienu savienojumu ar formulu (I) pēc jebkura punkta no 1. līdz 6. vai 13., vai tā farmakoloģiski pieņemamu sāli, kopā ar vienu vai vairākiem farmakoloģiski pieņemamiem atšķaidītājiem, nesējiem un/vai palīgvielām.
  16. 16. Savienojuma pēc jebkura punkta no 1. līdz 6. vai 13., vai tā farmakoloģiski pieņemamas sāls pielietojums tādu medikamentu ražošanai, kas paredzēti reimatoīdā artrīta, imūnogēnu vai neimūnogēnu hronisko iekaisuma slimību un vēža ārstēšanai. 5
LVP-94-02A 1993-01-05 1994-01-04 2-ciano-3-hydroxypropene amides LV10712B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB939300083A GB9300083D0 (en) 1993-01-05 1993-01-05 Chemical compounds

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LV10712A LV10712A (lv) 1995-06-20
LV10712B true LV10712B (en) 1995-12-20

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US (1) US5346912A (lv)
EP (1) EP0606175B1 (lv)
JP (1) JP3334988B2 (lv)
KR (1) KR100295717B1 (lv)
CN (1) CN1042935C (lv)
AT (1) ATE128968T1 (lv)
AU (1) AU663017B2 (lv)
BR (1) BR9400017A (lv)
CA (1) CA2112866C (lv)
CZ (1) CZ283948B6 (lv)
DE (1) DE69400024T2 (lv)
DK (1) DK0606175T3 (lv)
EE (1) EE03001B1 (lv)
ES (1) ES2078130T3 (lv)
FI (1) FI106553B (lv)
GB (1) GB9300083D0 (lv)
GR (1) GR3017723T3 (lv)
HR (1) HRP940006B1 (lv)
HU (1) HU216835B (lv)
IL (1) IL107788A (lv)
LT (1) LT3766B (lv)
LV (1) LV10712B (lv)
MX (1) MX9400274A (lv)
NO (1) NO300839B1 (lv)
NZ (1) NZ250520A (lv)
PL (1) PL175135B1 (lv)
RU (1) RU2126387C1 (lv)
SI (1) SI9300686A (lv)
SK (1) SK280508B6 (lv)
TW (1) TW259785B (lv)
UA (1) UA40573C2 (lv)
YU (1) YU49047B (lv)
ZA (1) ZA939118B (lv)

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EP1100495A4 (en) * 1998-07-28 2002-09-25 Smithkline Beecham Corp PROPENAMIDES AS CCR5 MODULATORS
EP1768662A2 (en) 2004-06-24 2007-04-04 Novartis Vaccines and Diagnostics, Inc. Small molecule immunopotentiators and assays for their detection
WO2009027393A2 (en) 2007-08-27 2009-03-05 Basf Se Pyrazole compounds for controlling invertebrate pests
AU2009295936B2 (en) 2008-09-24 2014-07-17 Basf Se Pyrazole compounds for controlling invertebrate pests
US8710056B2 (en) 2009-07-06 2014-04-29 Basf Se Pyridazine compounds for controlling invertebrate pests
EP2451804B1 (en) 2009-07-06 2014-04-30 Basf Se Pyridazine compounds for controlling invertebrate pests
WO2011009804A2 (en) 2009-07-24 2011-01-27 Basf Se Pyridine derivatives compounds for controlling invertebrate pests
KR20160079123A (ko) 2013-11-22 2016-07-05 젠자임 코포레이션 신경변성 질병을 치료하기 위한 신규한 방법
CN105693574B (zh) * 2014-11-25 2017-12-19 中国科学院大连化学物理研究所 2‑烷硫基烯酰胺衍生物及其合成方法

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NL186239B (nl) 1975-06-05 Hoechst Ag Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze.
DE2555789A1 (de) * 1975-12-11 1977-07-07 Hoechst Ag Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
US4435407A (en) * 1982-01-07 1984-03-06 Ciba-Geigy Corporation Certain substituted β-oxo-α-carbamoylpyrrolepropionitriles
DE3534440A1 (de) 1985-09-27 1987-04-02 Hoechst Ag Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes
US4888357A (en) 1988-01-26 1989-12-19 Bristol-Myers Company Antiarthritic β-cycloalkyl-β-oxopropionitriles
IL92508A0 (en) * 1988-12-08 1990-08-31 Ciba Geigy Ag Novel alpha-cyano-beta-oxopropionamides
DK0527736T3 (da) * 1990-05-18 1997-10-20 Hoechst Ag Isoxazol-4-carboxylsyreamider og hydroxyalkyliden-cyanoacetamider, lægemidler indeholdende disse forbindelser og anvendelsen af disse lægemidler.
IL99811A (en) * 1990-10-30 1996-03-31 Roussel Uclaf 3-Cycloalkyl-propanamides, tautomeric forms of these, their salts, method of preparation, use as drugs and preparations containing them
IL102790A (en) * 1991-09-17 1996-01-31 Roussel Uclaf History of 3-cycloalkyl-prop-2-anamide

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EP0606175A1 (fr) 1994-07-13
KR100295717B1 (ko) 2001-11-05
DK0606175T3 (da) 1996-02-19
FI106553B (fi) 2001-02-28
SI9300686A (en) 1994-09-30
FI940031A (fi) 1994-07-06
RU2126387C1 (ru) 1999-02-20
AU5213093A (en) 1994-07-14
GB9300083D0 (en) 1993-03-03
US5346912A (en) 1994-09-13
KR940018363A (ko) 1994-08-16
PL301774A1 (en) 1994-07-11
CN1097005A (zh) 1995-01-04
LV10712A (lv) 1995-06-20
SK149593A3 (en) 1994-12-07
MX9400274A (es) 1994-08-31
TW259785B (en) 1995-10-11
NO300839B1 (no) 1997-08-04
EP0606175B1 (fr) 1995-10-11
ATE128968T1 (de) 1995-10-15
JPH06211793A (ja) 1994-08-02
LTIP1634A (en) 1995-02-27
NO940020D0 (no) 1994-01-04
IL107788A (en) 1998-08-16
YU49047B (sh) 2003-07-07
AU663017B2 (en) 1995-09-21
LT3766B (en) 1996-03-25
RU94000064A (ru) 1996-07-10
FI940031A0 (fi) 1994-01-04
CA2112866A1 (fr) 1994-07-06
DE69400024D1 (de) 1995-11-16
GR3017723T3 (en) 1996-01-31
NZ250520A (en) 1996-08-27
ES2078130T3 (es) 1995-12-01
HUT71471A (en) 1995-11-28
NO940020L (lv) 1994-07-06
EE03001B1 (et) 1997-06-16
YU82593A (sh) 1996-07-24
ZA939118B (en) 1995-01-18
BR9400017A (pt) 1994-08-02
IL107788A0 (en) 1994-02-27
UA40573C2 (uk) 2001-08-15
HRP940006B1 (en) 1999-12-31
CZ283948B6 (cs) 1998-07-15
JP3334988B2 (ja) 2002-10-15
CA2112866C (fr) 2007-03-13
HU216835B (hu) 1999-09-28
HRP940006A2 (en) 1996-10-31
PL175135B1 (pl) 1998-11-30
DE69400024T2 (de) 1996-04-04
CN1042935C (zh) 1999-04-14
SK280508B6 (sk) 2000-03-13
CZ292193A3 (en) 1994-07-13
HU9400033D0 (en) 1994-05-30

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