LV12258B - Diaminociklobutēn-3,4-dioni kā gludo muskuļu relaksanti - Google Patents

Diaminociklobutēn-3,4-dioni kā gludo muskuļu relaksanti Download PDF

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LV12258B
LV12258B LVP-99-23A LV990023A LV12258B LV 12258 B LV12258 B LV 12258B LV 990023 A LV990023 A LV 990023A LV 12258 B LV12258 B LV 12258B
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cyclobut
dione
ene
ylamino
amino
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John Anthony Butera
Schuyler Adam Antane
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American Home Products Corporation
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • A—HUMAN NECESSITIES
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    • A61P11/00—Drugs for disorders of the respiratory system
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/43—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
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Claims (15)

  1. 5 10 FORMULA 1. Savienojums ar formulu: w \ / NI H / NI R2 (I) kur: Ri un R2 ir, neatkarīgi viens no otra, ūdeņradis, Cmo lineāra alkil-, sazarota alkil-, vai C3-10 cikliska vai bicikliska alkilgrupa; A ir izvēlēts no grupas, kas ietver: C1-10 LV 12258 *ΛΛΛ Λ RA Ņ^Ņ "'J R*
    vw 2 kur: R3 ir ūdeņradis, Cm alkil-, Čm perfluoralkil-, Cm aikoksi-, Cm perfluoralkoksi-, amino-, Cm alkilamino-, C2-12 dialkilamino-, Cm alkilsulfonamidogrupa, alkilkarboksamidogrupa, kas satur 2-7 oglekļa atomus, nitro-, ciano-, karboksilgrupa; vai, A ir aizvietota fenilgrupa ar sekojošu formulu:
    kur: R4 un Rs, neatkarīgi viens no otra, ir izvēlēti no: ciano-, nitro-, amino-, Cm alkil-, Cm perfluoralkil-, Cm aikoksi-, Cm perfluoralkoksi-, amino-, Cm alkilamino-, C2-12 dialkilamino-, sulfamil-, Cm alkilsulfonamidogrupa, Ce-12 arilsulfonamidogrupa, alkilkarboksamidogrupa, kas satur 2-7 oglekļa atomus, arilkarboksamidogrupa, kas satur 7 līdz 13 oglekļa atomus, Cm alkilsulfonil-, Cm perfluoralkilsulfonil-, Ce.12 arilsulfonilgrupa, hlors, broms, fluors, jods, 1-imidazolil-, karboksilgrupa vai ūdeņradis, ar nosacījumu, ka R4 un R5 vienlaicīgi nevar būt ūdeņradis; vai to farmaceitiski pieņemama sāls.
  2. 2. Savienojums saskaņā ar 1. punktu, kurā A ir izvēlēts no:
    3 LV 12258 vai, A ir aizvietota fenilgrupa ar sekojošu formulu:
    kur 5 R4 un R5, neatkarīgi viens no otra, ir izvēlēti no: ciano-, nitro-, amino-, hlors, broms, fluors, jods, 1-imidazolil-, karboksilgrupa vai ūdeņradis, ar nosacījumu, ka R4 un R5 vienlaicīgi nevar būt ūdeņradis; vai to farmaceitiski pieņemama sāls.
  3. 3. Savienojums saskaņā ar 1. punktu, kurā A ir izvēlēts no:
    vai, A ir aizvietota fenilgrupa ar sekojošu formulu: 15
    kur: R4 un R5, neatkarīgi viens no otra, ir izvēlēti no: ciano-, nitro-, amino-, hlors, 20 broms, fluors, jods, 1-imidazolil-, karboksilgrupa vai ūdeņradis, ar nosacījumu, ka R4 un R5 vienlaicīgi nevar būt ūdeņradis; 4 vai to farmaceitiski pieņemama sāls. 4. 3-Alkilamino-4-[(aizvietots fenil)amino]-ciklobut-3-ēn-1,2-dions, kurā minētā alkilgrupa satur 1 līdz 6 oglekļa atomus un fenilgrupa ir aizvietota ar 1 vai 2 ciano-, nitro-, amino-, halogēnu vai karboksilgrupu.
  4. 5. Savienojums saskaņā ar 1. punktu, kurš ir: 3-(piridīn-4-ilamino)-4-(1,2,2-trimetil-propilamino)-ciklobut-3-ēn-1 ,2-dions; (ekso)-3-(biciklo[2.2.1]hept-2-ilamino)-4-(piridīn-4-ilamino)-ciklobut-3-ēn-1,2-dions; 3-(piridīn-3-ilamino)-4-(1,2,2-trimetil-propilamino)-ciklobut-3-ēn-1,2-dions; 3-(2-metiletilamino)-4-(piricrrn-3-ilamino)-ciklobut-3-ēn-1,2-dions; 3-dimetilamino-4-(piridTn-3-ilamino)-ciklobut-3-ēn-1,2-dions; 3-amino-4-(piridīn-3-ilamino)-ciklobut-3-ēn-1,2-dions; vai 3-terc-butilamino-4-(piridīn-3-ilamino)-ciklobut-3-ēn-1,2-dions.
  5. 6. Savienojums saskaņā ar 1. punktu, kurš in 3-terc-butilamino-4-(izohinolīn-5-ilamino)-ciklobut-3-ēn-1,2-dions; 3-amino-4-(izohinolīn-5-ilamino)-ciklobut-3-ēn-1,2-dions; 3-(hinolīn-8-ilamino)-4-( 1,2,2-trimetil-propilamino)-ciklobut-3-ēn-1,2-dions; 3-metilamino-4-(hinolīn-8-ilamino)-ciklobut-3-ēn-1,2-dions; 3-amino-4-(hinolīn-8-ilamino)-ciklobut-3-ēn-1,2-dions; 3-(hinolīn-3-i lamino)-4-( 1,2,2-trimetil-propilamino)-ciklobut-3-ēn-1,2-dions; 3-terc-butilamino-4-(hinolīn-3-ilamino)-ciklobut-3-ēn-1,2-dions; 3-(hinolīn-3-ilamino)-4-(1,1 -diimetil-propilamino)-ciklobut-3-ēn-1,2-dions; 3-(6-metoksi-hinolīn-8-ilamino)-4-(1,2,2-trimetil-propilamino)-ciklobut-3-ēn-1,2-dions; 3-(6-metoksi-hinolīn-8-ilamino)-4-metilamino-ciklobut-3-ēn-1,2-dions; 5 LV 12258 3-terc-butilamino-4-(hinolīn-6-ilamino)-ciklobut-3-ēn-1,2-dions; vai 3- (izohinolīn-5-ilamino)-4-metilamino-ciklobut-3-ēn-1,2-dions.
  6. 7. Savienojums saskaņā ar 1. punktu, kurš ir: 3-terc-butilamino-4-(1 H-indazol-6-ilamino)-ciklobut-3-ēn-1,2-dions; (ekso)-4-[2-(biciklo[2.2.1]hept-2-ilamino)-3,4-diokso-ciklobut-1-enilaminoj-benzonitrils; vai 4- [3,4-diokso-2-(1,2,2-trimetil-propilamino)-ciklobut-1 -enilaminoj-benzosulofonamīds. 10
  7. 8. Savienojums saskaņā ar 1. punktu, kurš ir 4-(3,4-diokso-2-(1,2,2-trimetilpropilamino)-ciklobut-1-enilamino]-benzonitrils.
  8. 9. Savienojums saskaņā ar 1. punktu, kurš ir (+)-(R)- 4-[3,4-diokso-2-(1,2,2-15 trimetilpropilamino)-ciklobut-1-enilamino]-3-etil-benzonitrils.
  9. 10. Savienojums saskaņā ar 1. punktu, kurš ir (+)-(R)-4-[3,4-diokso-2-(1,2,2-trim,etilpropilamino)-ciklobut-1-enilamino]-3-metoksi-benzonitrils.
  10. 11. Farmaceitiska kompozīcija, kas ietver savienojumu saskaņā ar jebkuru no punktiem 1 līdz 10 kombinācijā vai saistībā ar farmaceitiski pieņemamu nesēju.
  11. 12. Savienojuma saskaņā ar 1. punktu iegūšanas paņēmiens, kas ietver 25 savienojuma ar formulu lla: \ f > \ N I H X (Ha) 6 , kur Ai ir A, kā definēts 1. punktā vai par to pārvēršama atomu grupa, un X ir atšķeļama grupa, reakciju ar savienojumu ar formulu IV: 5 R a1 HN (IV) R a2 kur Rai un Rg2 ir, attiecīgi, Ri un R2, kā definēts 1. punktā vai par to pārvēršama atomu grupa un, kad piemērots, Ai pārvēršanu par A vai Rai pārvēršanu par Ri, vai Ra2 pārvēršanu par R2 un, pēc vēlēšanās, savienojuma 10 ar formulu I pārvēršanu par tā farmaceitiski pieņemamu sāli vai savienojuma ar formulu I sāls pārvēršanu par savienojumu ar formulu I.
  12. 13. Savienojuma saskaņā ar jebkuru no punktiem 1 līdz 10 izmantošana par farmaceitisku līdzekli.
  13. 14. Savienojuma saskaņā ar jebkuru no punktiem 1 līdz 10 pielietošana, lai sagatavotu medikamentus gludo muskuļu kontrakciju traucējumu ārstēšanai.
  14. 15. Savienojums ar formulu lla A CLV-/ (lla) N 20 H 7 LV 12258 kur X ir atšķeļamā grupa un A1 ir izvēlēts no grupas, kas sastāv no:
    5 kur: R3 ir ūdeņradis, Ci-β alkil-, Ci-β perfluoralkil-, Ci-e alkoksi-, Ci^ perfluoralkoksi-, amino-, Ci-β alkilamino-, C2-12 dialkilamino-, Ci-e alkilsulfonamidogrupa, alkilkarboksamidogrupa, kas satur 2-7 oglekļa atomus, nitro-, ciano-, karboksilgrupa; 10 vai, Aļ ir aizvietota fenilgrupa ar sekojošu formulu: U-R< f>5 kur: R4 un R5l neatkarīgi viens no otra, ir izvēlēti no: ciano-, nitro-, amino-, C1.6 15 alkil-, C1-6 perfluoralkil-, Ci^ alkoksi-, Cļ-e perfluoralkoksi-, amino-, alkilamino-, C2-12 dialkilamino-, sulfamil-, Ci^ alkilsulfonamido-, C6-12 ariisulfonamidogrupa, alkilkarboksamidogrupa, kas satur 2-7 oglekļa atomus, 8 arilkarboksamidogrupa, kas satur 7 līdz 13 oglekļa atomus, Ci-e alkilsulfonil-Cļ-6 perfluoralkilsulfonil-, Ce-12 arilsulfonilgrupa, hlors, broms, fluors, jods, 1-imidazolil-, karboksilgrupa vai ūdeņradis, ar nosacījumu, ka R4 un Rs vienlaicīgi nevar būt ūdeņradis.
  15. 16. Savienojums saskaņā ar 15. punktu, kur X ir metoksi-, etoksi-, izopropoksigrupa vai halogēns.
LVP-99-23A 1993-11-17 1999-02-15 Diaminociklobutēn-3,4-dioni kā gludo muskuļu relaksanti LV12258B (lv)

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US08/153,706 US5354763A (en) 1993-11-17 1993-11-17 Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones

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HU215603B (hu) 1999-01-28
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US5401753A (en) 1995-03-28
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US5354763A (en) 1994-10-11
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