YU46698B - Postupak za dobijanje derivata 4-aril-5-karbamoil-1,4-dihidropiridina - Google Patents

Postupak za dobijanje derivata 4-aril-5-karbamoil-1,4-dihidropiridina

Info

Publication number
YU46698B
YU46698B YU182088A YU182088A YU46698B YU 46698 B YU46698 B YU 46698B YU 182088 A YU182088 A YU 182088A YU 182088 A YU182088 A YU 182088A YU 46698 B YU46698 B YU 46698B
Authority
YU
Yugoslavia
Prior art keywords
compound
formula
aryl
alkoxy
alkyl
Prior art date
Application number
YU182088A
Other languages
English (en)
Other versions
YU182088A (en
Inventor
K. Cooper
M.J. Fray
K. Richardson
J. Steele
Original Assignee
Pfizer Ltd.
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 GB878722977A external-priority patent/GB8722977D0/en
Priority claimed from GB888804441A external-priority patent/GB8804441D0/en
Application filed by Pfizer Ltd. filed Critical Pfizer Ltd.
Publication of YU182088A publication Critical patent/YU182088A/xx
Publication of YU46698B publication Critical patent/YU46698B/sh

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/10—Heterocyclic 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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 three or more hetero rings
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/14—Heterocyclic 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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

POSTUPAK ZA DOBIJANJE DERIVATA 4-ARIL-5-KARBAMOIL-1,4-DIHIDROPIRIDINA, formule: u kojoj je R fenil ili fenil supstituisan sa jednim ili vise supstituenata nezavisno izabranih od nitro, halo, C1-C4alkil, C1-C4alkoksi, aril (C1-C4) alkoksi, fluoro (C1-C4)alkoksi, C1-C4alkiltio, C1-C4alkilsul-fonil, hidroksi, trifluorometil i cijano, ili fenil kondenzovan u prsten dioksolana; R1 i R2 su svaki za sebe nezavisno H ili C1-C6alkil, ili R1 i R2 sacinjavaju zajedno pirolidinil, piperidino, morfolino, piperazinil, N-(C1-C4alkil)piperazinil ili N-(C2-C4alkanoil)-piperazinil grupu; R2 je H ili C1-C4 alkil a R1 je CN, C3-C7cikloalkil, aril, heteroaril ili C1-C4alkil grupa, koja moze biti supstituisana sa jednim ili vise supstituenata od kojih je svaki nezavisno izabran od C3-C7cikloalkil, C1-C4alkoksikarbonil, aril ili heteroaril; Z je izabran od OH, C1-C6 alkoksi i aril (C1-C6)alkoksi, Y je 1,4 fenilen ili piridin-2,5-diil, a X je 5- ili 6-clana grupa koja sadrzi jedan ili vise azotovih atoma u svom prstenu; koji prsten moze biti kondenzovan u benzenov prsten ili dalje u 5 ili 6-clani aromaticni heterociklicni prsten koji sadrzi jedan ili dva atoma azota, najmanje jedan od pomenutih heterociklicnih prstenova po zelji takodje sadrzi atom kiseonika ili sumpora, i po zelji supstituisan sa jednim ili vise supstituenata nezavisno izabranih od C1-C4alkil, halo, CF3 i CN; i njihovih farmaceutski prihvatljivih soli, gde aril znaci fenil ili fenil supstituisan sa jednim ili dva supstituenta izabranih od halo, tri-fluorometil, C1-C4alkil, hidroksi, C1-C4 alkoksi, (C1-C4alkoksi)karbonil, sulfamoil i CN, heteroaril u definiciji R1 znaci 5- ili 6-clanu aromaticnu heterociklicnu grupu koja sadrzi jedan ili dva heteroatoma koji su nezavisno izabrani od N,O i S i koji mogu po zelji biti kondenzovani u benzenov prsten i koji mogu po zelji biti supstituisani u najmanje jednom od heterociklicnih i kondenzovanih benzenovih prstenova sa jednim ili dva supstituenta izabranih od C1-C4 alkoksi i halo, pri cemu halo znaci fluoro, hloro, bromo ili jodo, naznacen time, sto reaguje jedinjenje formule XN sa p-haloacetofenonom u prisustvu kalijum karbonata u anhidrovanom rastvaracu da bi se dobilo jedinjenje X-Y -COCH3 gde su X i Y prethodno definisani, sto zatim tako dobijeno jedinjenje reaguje sa jedinjenjem formule (Z2)CO u prisustvu natrijum hidrida, gde je Z prethodno definisano, pri cemu se dobija jedinjenje formule (III) gde su Y i X prethodno definisani, R3 je C1-C6 alkil ili aril (C1-C4alkil), sto zatim tako dobijeno jedinjenje reaguje sa RCHO, gde je R prethodno definisano, u prisustvu izopropil alkohola i piperidina na sobnoj temperaturi, pri cemu se dobija jedinjenje formule (IV) u kojoj su R, R3 X i Y prethodno definisani, sto zatim reaguje tako dobijeno jedinjenje formule (IV) sa jedinjenjem formule (II) u kojoj su R1 i R2 prethodno definisani u prisustvu rastvaraca, i sto, ako se zeli dobiti jedinjenje formule (I) u kojoj je Z OH, vrsi se redukcija jedinjenja formule (I) u
YU182088A 1987-09-30 1988-09-29 Postupak za dobijanje derivata 4-aril-5-karbamoil-1,4-dihidropiridina YU46698B (sh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB878722977A GB8722977D0 (en) 1987-09-30 1987-09-30 Therapeutic agents
GB888804441A GB8804441D0 (en) 1988-02-25 1988-02-25 Therapeutic agents

Publications (2)

Publication Number Publication Date
YU182088A YU182088A (en) 1990-06-30
YU46698B true YU46698B (sh) 1994-04-05

Family

ID=26292797

Family Applications (1)

Application Number Title Priority Date Filing Date
YU182088A YU46698B (sh) 1987-09-30 1988-09-29 Postupak za dobijanje derivata 4-aril-5-karbamoil-1,4-dihidropiridina

Country Status (26)

Country Link
US (3) US4935430A (sh)
EP (1) EP0310386B1 (sh)
JP (2) JP2660016B2 (sh)
KR (1) KR900008318B1 (sh)
CN (1) CN1032648C (sh)
AU (2) AU597190B2 (sh)
CA (1) CA1340785C (sh)
CY (1) CY1722A (sh)
DE (1) DE3866077D1 (sh)
DK (1) DK170376B1 (sh)
EG (1) EG18563A (sh)
ES (1) ES2038766T3 (sh)
FI (1) FI93444C (sh)
GR (1) GR3003468T3 (sh)
HK (1) HK66093A (sh)
HU (1) HU201061B (sh)
IE (1) IE61045B1 (sh)
IL (1) IL101332A0 (sh)
MY (1) MY104933A (sh)
NO (1) NO168107C (sh)
NZ (1) NZ226397A (sh)
PH (1) PH26046A (sh)
PL (1) PL157186B1 (sh)
PT (1) PT88614B (sh)
SG (1) SG49393G (sh)
YU (1) YU46698B (sh)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8906324D0 (en) * 1989-03-20 1989-05-04 Pfizer Ltd 1,4-dihydropyridines
US4990518A (en) * 1989-09-13 1991-02-05 G. D. Searle & Co. Pharmacologically active heteroaryl substituted imidazo (4,5-c) pyridines
GB9010404D0 (en) * 1990-05-09 1990-06-27 Pfizer Ltd Therapeutic agents
GB9015524D0 (en) * 1990-07-13 1990-08-29 Pfizer Ltd Therapeutic agents
GB9019409D0 (en) * 1990-09-05 1990-10-17 Pfizer Ltd Therapeutic agents
JP2829451B2 (ja) * 1990-11-30 1998-11-25 大塚製薬株式会社 活性酸素抑制剤
US5288866A (en) * 1991-12-20 1994-02-22 American Cyanamid Company 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds useful for the preparation of 5- (substituted methyl)-2,3-pyridinedicarboxylic acids
DK40192D0 (da) * 1992-03-26 1992-03-26 Neurosearch As Imidazolforbindelser, deres fremstilling og anvendelse
MY128323A (en) 1996-09-30 2007-01-31 Otsuka Pharma Co Ltd Thiazole derivatives for inhibition of cytokine production and of cell adhesion
US6232320B1 (en) 1998-06-04 2001-05-15 Abbott Laboratories Cell adhesion-inhibiting antiinflammatory compounds
HUP0102366A2 (hu) * 1998-06-04 2001-11-28 Abbott Laboratories Sejttapadást gátló, gyulladáscsökkentő hatású vegyületek
WO2000075145A1 (en) * 1999-06-03 2000-12-14 Abbott Laboratories Cell adhesion-inhibiting antiinflammatory compounds
CA2417960C (en) * 2000-08-04 2012-07-10 Dmi Biosciences, Inc. Method of using diketopiperazines and composition containing them
CN104095851A (zh) 2003-05-15 2014-10-15 安皮奥制药股份有限公司 T-细胞介导的疾病的治疗
CN113999167B (zh) * 2021-10-18 2023-09-29 蚌埠中实化学技术有限公司 一种4-氯-2,6-二甲基-3-硝基吡啶的制备方法
CN117568743B (zh) * 2024-01-15 2024-03-19 江苏普坦科金属科技有限公司 一种铁基材料的表面耐腐蚀耐磨处理工艺

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US3971791A (en) * 1972-03-06 1976-07-27 Bayer Aktiengesellschaft 2-Amino-1,4-dihydropyridine derivatives
DE2738153A1 (de) * 1977-08-24 1979-03-08 Bayer Ag 2-pyridyl-1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2752820A1 (de) * 1977-11-26 1979-05-31 Bayer Ag Neue nitrosubstituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
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US4353905A (en) 1981-09-17 1982-10-12 Warner-Lambert Company Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones
US4414213A (en) * 1982-03-22 1983-11-08 Mead Johnson & Company Dihydropyridyl cyclic imidate esters and their pharmaceutical use
DE3363743D1 (en) 1982-07-22 1986-07-03 Pfizer Ltd Dihydropyridine anti-ischaemic and antihypertensive agents
EP0125803A3 (en) * 1983-04-27 1987-01-21 FISONS plc Pharmaceutically active dihydropyridines
JPS60120861A (ja) * 1983-12-02 1985-06-28 Otsuka Pharmaceut Co Ltd ジヒドロピリジン誘導体
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GB8803963D0 (en) * 1988-02-19 1988-03-23 Pfizer Ltd Therapeutic agents

Also Published As

Publication number Publication date
IL101332A0 (en) 1992-11-15
IE61045B1 (en) 1994-09-07
PL157186B1 (pl) 1992-05-29
CN1032648C (zh) 1996-08-28
FI884471A (fi) 1989-03-31
KR900008318B1 (ko) 1990-11-12
GR3003468T3 (en) 1993-02-17
AU2297388A (en) 1989-04-06
PL274977A1 (en) 1989-08-21
JP2898256B2 (ja) 1999-05-31
PT88614B (pt) 1993-07-30
KR890005054A (ko) 1989-05-11
JPH01113367A (ja) 1989-05-02
FI93444C (fi) 1995-04-10
HU201061B (en) 1990-09-28
DK170376B1 (da) 1995-08-14
EP0310386A3 (en) 1989-11-15
AU6126190A (en) 1990-11-29
US4935430A (en) 1990-06-19
NZ226397A (en) 1990-11-27
PT88614A (pt) 1989-07-31
EG18563A (en) 1993-08-30
FI93444B (fi) 1994-12-30
HUT48872A (en) 1989-07-28
HK66093A (en) 1993-07-16
CA1340785C (en) 1999-10-12
YU182088A (en) 1990-06-30
AU597190B2 (en) 1990-05-24
MY104933A (en) 1994-07-30
EP0310386A2 (en) 1989-04-05
SG49393G (en) 1993-07-09
EP0310386B1 (en) 1991-11-06
DK544588A (da) 1989-05-11
FI884471A0 (fi) 1988-09-29
IE882944L (en) 1989-03-30
JPH09315973A (ja) 1997-12-09
CY1722A (en) 1994-05-06
NO884333L (no) 1989-03-31
NO168107B (no) 1991-10-07
AU617256B2 (en) 1991-11-21
US5063237A (en) 1991-11-05
NO168107C (no) 1992-01-15
DE3866077D1 (de) 1991-12-12
DK544588D0 (da) 1988-09-29
JP2660016B2 (ja) 1997-10-08
NO884333D0 (no) 1988-09-29
CN1032439A (zh) 1989-04-19
US5120747A (en) 1992-06-09
ES2038766T3 (es) 1993-08-01
PH26046A (en) 1992-01-29

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