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1. WO1999003844 - PYRAZINE DERIVATIVES, PREPARATION AND MEDICINES CONTAINING THEM

Publication Number WO/1999/003844
Publication Date 28.01.1999
International Application No. PCT/FR1998/001542
International Filing Date 15.07.1998
Chapter 2 Demand Filed 27.01.1999
IPC
C07D 213/38 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic 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
02having three double bonds between ring members or between ring members and non-ring members
04having 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
24with substituted hydrocarbon radicals attached to ring carbon atoms
36Radicals substituted by singly-bound nitrogen atoms
38having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
C07D 213/81 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic 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
02having three double bonds between ring members or between ring members and non-ring members
04having 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
60with 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
78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
81Amides; Imides
C07D 213/82 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic 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
02having three double bonds between ring members or between ring members and non-ring members
04having 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
60with 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
78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
81Amides; Imides
82in position 3
C07D 241/12 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
241Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
02not condensed with other rings
10having three double bonds between ring members or between ring members and non-ring members
12with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
C07D 241/24 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
241Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
02not condensed with other rings
10having three double bonds between ring members or between ring members and non-ring members
14with 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
24Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
CPC
A61K 31/4965
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
495having six-membered rings with two ; or more; nitrogen atoms as the only ring heteroatoms, e.g. piperazine ; or tetrazines
4965Non-condensed pyrazines
A61P 3/10
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
3Drugs for disorders of the metabolism
08for glucose homeostasis
10for hyperglycaemia, e.g. antidiabetics
C07D 213/38
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic 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
02having three double bonds between ring members or between ring members and non-ring members
04having 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
24with substituted hydrocarbon radicals attached to ring carbon atoms
36Radicals substituted by singly-bound nitrogen atoms
38having only hydrogen, hydrocarbon radicals attached to the substituent nitrogen atom
C07D 213/81
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic 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
02having three double bonds between ring members or between ring members and non-ring members
04having 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
60with heteroatoms or with carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
78Carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals
81Amides; Imides
C07D 213/82
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic 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
02having three double bonds between ring members or between ring members and non-ring members
04having 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
60with heteroatoms or with carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
78Carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals
81Amides; Imides
82in position 3
C07D 241/12
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
241Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
02not condensed with other rings
10having three double bonds between ring members or between ring members and non-ring members
12with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Applicants
  • RHONE-POULENC RORER S.A. [FR]/[FR] (AL, AM, AT, AU, AZ, BA, BB, BE, BF, BG, BJ, BR, BY, CA, CF, CG, CH, CI, CM, CN, CU, CY, CZ, DE, DK, EE, ES, FI, FR, GA, GB, GE, GH, GM, GN, GR, GW, HR, HU, ID, IE, IL, IS, IT, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MC, MD, MG, MK, ML, MN, MR, MW, MX, NE, NL, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, SN, SZ, TD, TG, TJ, TM, TR, TT, UA, UG, UZ, VN, YU, ZW)
  • BASHIARDES, Georges [CY]/[FR] (UsOnly)
  • CARRY, Jean-Christophe [FR]/[FR] (UsOnly)
  • EVERS, Michel [BE]/[FR] (UsOnly)
  • FILOCHE, Bruno [FR]/[FR] (UsOnly)
  • MIGNANI, Serge [FR]/[FR] (UsOnly)
Inventors
  • BASHIARDES, Georges
  • CARRY, Jean-Christophe
  • EVERS, Michel
  • FILOCHE, Bruno
  • MIGNANI, Serge
Agents
  • MORVAN, Michèle
Priority Data
97/0905817.07.1997FR
Publication Language French (fr)
Filing Language French (FR)
Designated States
Title
(EN) PYRAZINE DERIVATIVES, PREPARATION AND MEDICINES CONTAINING THEM
(FR) DERIVES DE PYRAZINE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
Abstract
(EN) The invention concerns pyrazine derivatives of formula (I) in which: either R represents a nitrogen atom, R1 represents a -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5R6, -CH2-N(CH2OH)2, -CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 radical and one of its substituents; R3 or R4 represents a hydrogen atom and the other is identical to R1, and R2 represents an hydrogen atom, or R represents a CH radical, R1 and R4 are identical and represent each a -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5R6, -CH2-N(CH2OH)2, -CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 radical; and R2 and R3 represent a hydrogen atom, or R1 and R3 are identical and represent each a -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5R6, -CH2-N(CH2OH)2, CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 radical and R2 and R4 represent a hydrogen atom, or R2 and R3 are identical and represent each a -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2NR5R6, -CH2-N(CH2OH)2, -CH2-N(CH2(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 radical and R1 and R4 represent a hydrogen atom, their stereoisomers, their salts, the novel derivatives of formula (I) and their preparation.
(FR) Médicaments contenant des dérivés de pyrazine de formule (I) dans laquelle soit R représente un atome d'azote, R1 représente un radical -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5-R6, -CH2-N(CH2OH)2, -CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 et l'un des substituants R3 ou R4 représente un atome d'hydrogène et l'autre est identique à R1 et R2 représente un atome d'hydrogène, soit R représente un reste CH, R1 et R4 sont identiques et représentent chacun un radical -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5R6, -CH2-N(CH2OH)2, -CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 et R2 et R4 représentent un atome d'hydrogène, ou bien R1 et R3 sont identiques et représentent chacun un radical -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5R6, -CH2-N(CH2OH)2, -CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 et R4 représentent un atome d'hydrogène, ou bien R2 et R2 et R3 sont identiques et représentent chacun un radical -CO-NR5R6, -CO-N(CH(CH2OH)2)2, -CO-N(CH2OH)2, -CO-N(CH2-CH(CH2OH)2)2, -CO-N(CH2-(CHOH)n-CH2OH)2, -CH2-O-R6, -NR5-CO-R6, -CH2-NR5R6, -CH2-N(CH2OH)2, -CH2-N(CH2-(CHOH)y-CH2OH)2, -CH2-N(CH(CH2OH)2)2, -CH2-N(CH2-CH(CH2OH)2)2 et R1 et R4 représentent un atome d'hydrogène, leurs stéréoisomères, leurs sels, les nouveaux dérivés de formule (I) et leur préparation.
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