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LV10439B - N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions containing them - Google Patents

N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions containing them Download PDF

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Publication number
LV10439B
LV10439B LVP-93-147A LV930147A LV10439B LV 10439 B LV10439 B LV 10439B LV 930147 A LV930147 A LV 930147A LV 10439 B LV10439 B LV 10439B
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alkyl
phenyl
compound
formula
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LVP-93-147A
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LV10439A (lv
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Bernhart Claude
Breliere Jean-Claude
Clement Jacques
Nisato Dino
Perreaut Pierre
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Sanofi Elf
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26227935&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LV10439(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from FR9003563A external-priority patent/FR2659967B1/fr
Priority claimed from FR9010144A external-priority patent/FR2665702B1/fr
Application filed by Sanofi Elf filed Critical Sanofi Elf
Publication of LV10439A publication Critical patent/LV10439A/lv
Publication of LV10439B publication Critical patent/LV10439B/en

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    • A—HUMAN NECESSITIES
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
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    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
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Claims (14)

  1. LV 10439 Izgudrojuma formula. I. N-Aizvietoti heterocikliskie savienojumi ar formulu:
    I kurā: - Rj un R2 ir vienādi vai atšķirīgi un katrs, neatkarīgi viens no otra, ir ūdeņradis vai grupa, izvēlēta no alkil- Cj-Cg, alkoksi- C1-C4, amino-, aminometil-, karboksi-, alkoksikarbonil-, kurā alkoksigrupa ir ar C1-C4, ciāno-, tetrazolil-, metiltetrazolil-, metilsulfonilamino-, trifluormetilsulfonilamino-, trifluormetilsulfonilaminometil-, N-ciānoacetamīdo-, N-hidroksiacetamīdo-, N-/(4-karboksi)-I,3-tiazol-2-il/-acetamīdo-, ureīdo-, 2-ciānoguanidīnkarbonil-, 2-ciānoguanidīnmetil-, I-imidazolilkarbonil-, 3-ciāno-2-metilizotioureīdometil- grupām, pie nosacījuma, ka vismaz viens no aizvietotājiem Rj vai R2 ir atšķirīgs no ūdeņraža; - R3 ir ūdeņradis, alkil- Cj-Cg, neaizvietots vai aizvietots ar vienu vai vairākiem halogēna atomiem, alkenil- C2-Cg, cikloalkil-C3-C7, fenilalkil-, kurā alkil-ir ar C1-C3, fenilalkenil-, kurā alkenil- ir ar C2-C3, fenil-, uzrādītās fenilgrupas ir 2 neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēna atomiem, alkil- C1-C4, halogēnalkil- Cj-C^ polihalogēn- C1-C4, hidroksil- vai alkoksi- C1-C4; - R4 un R5 ir katrs, neatkarīgi viens no otra, alkil- Cj-Cg fenil-, fenilalkil-, kurā alkil- ir ar C1-C3, uzrādītās alkil-, fenil- un fenilalkilgrupas ir neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēna atomiem vai vienu grupu, kura izvēlēta no perfluoralkil- C1-C4, hidroksil-, alkoksi- CJ-C4 grupām; - vai R4 un R5 kopā veido grupu ar formulu =CR7Rg, kurā R7 ir ūdeņradis, alkil- CJ-C4 vai fenil-, bet Rg ir alkil- C1-C4 vai fenil-; -vai arī R4 un R5 kopā veido grupu ar formulu (CH2)n. vai grupu ar formulu (CH2)pY(CH2)q, kurā Y ir skābekļa atoms, vai sera atoms, vai oglekļa atoms, aizvietots ar alkil- C1-C4, fenil- vai fenilalkil-, kurā alkil- ir ar C1-C3, vai grupu N-Rg, kurā Rg ir ūdeņradis, alkil- CJ-C4, fenilalkil-, kurā alkil- ir ar C1-C3, alkilkarbonil- C1-C4, halogenalkilkarbonil- C1-C4, polihalogenalkilkarbonil- CJ-C4, benzoil-, α -aminoacil- vai N-aizsarggrupa, vai R4 un R5 kopā ar oglekļa atomu, pie kura tie pievienoti, veido indiān- vai adamantān-; - p + q = m ; - n ir vesels skaitlis ar vērtībām no 2 līdz II; - m ir vesels skaitlis ar vērtībām no 2 līdz 5 ; - X ir skābekļa atoms vai sēra atoms ; - z un t ir nulle vai viens no indeksiem ir nulle, bet otrs - ir I; un tā sāļi.
  2. 2. Savienojums, atbilstoši izg.f.I.punktam, kas a t š ķ i r a s ar to, ka Ri ir orto-stāvoklī un ir kārboksigrupa vai tetrazolilgrupa, bet R2 ir ūdeņradis.
  3. 3. Savienojums, atbilstoši kādam vienam no izg.f.I-2 punktiem, kas atšķiras ar to, ka R4 un R5 veido ar oglekli, pie kura tie pievienoti, ciklopentān- vai cikloheksān- ciklus.
  4. 4. Savienojums, atbilstoši kādam vienam no izg.f.I-3 punktiem, kas a t š ķ i r a s ar to, ka R3 ir alkil- Cj-Cg grupa ar taisnu virkni.
  5. 5. Savienojums, atbilstoši kādam vienam no izg.f.I-4 punktiem, kas a t š ķ i r a s ar to, ka X ir skābeklis.
  6. 6. Savienojums, atbilstoši kādam vienam no izg.f.I-5 punktiem, kas atšķiras ar to, ka z = t = 0.
  7. 7. Savienojums, atbilstoši izg.f.I.punktam, kas a t š ķ i r a s ar to, ka tas ir 2-n-butil^-spirociklopentān-I-ļVT -(5-tetrazolil)-4-difenilil/-metil]-2-imidazolīn-5-ons vai viens no tā sāļiem ar skābēm vai bāzēm.
  8. 8. Paņēmiens savienojuma (I) , atbilstošs kādam vienam no izg.f.I-7 punktiem, iegūšanai, kas atšķirasar to,ka: ai) heterociklisko savienojumu ar formulu: J4 ZT2 0 = K5/_(CxK2>t (CH0) itf H 2 3 LV 10439 kurā z, t, R3, R4 un R5 ir tādas nozīmes, kā uzrādīts savienojumam (I) izg.f.I.punktā, pakļauj iedarbībai ar (4-difenilil)-metil- atvasinājumu, kura formula ir:
    2 kurā Hal ir halogēna atoms, bet R’j un R’2 ir attiecīgi Rj un R2, vai Rj un R2 grupas priekšteces; bl) ja vajadzīgs, iepriekšs iegūto savienojumu ar formulu:
    apstrādā ar Lewesson reaktīvu : 2,4-bis-(4-metoksifenil)-l,3-ditia-2,4-difofetān-2,4-disulfīdu; cl) savienojumu, kas iegūts ai) vai bl) stadijās, ar formulu :
    kurā X ir skābekļa atoms vai sēra atoms, apstrādā lai iegūtu savienojumu (I), ko realizē pārvēršot grupas R’j un/vai R'2 attiecīgi par grupām Rj un/vai R2.
  9. 9. Paņēmiens savienojuma (I) iegūšanai, atbilstoši kādam vienam no izg.f.I-7 punktiem, kas a t š ķ i r a s ar to, ka: a2) aminoskābi ar formulu: 7 *4 4 R
    NHPr 5 <k>* COOLi kurā z, t, R4 un R5 ir tādas nozīmes, kā uzrādīts savienojumam (I) izg.f.I. punktā; un kurā aminogrupa ir aizsargāta ar grupu Pr, pakļauj iedarbībai ar (4-difenilil)-metilamīna atvasinājumu, kura formula ir: I R 2 R- S «2» - CH2 "Λ // kurā R'i un R'2 ir attiecīgi Rj un R2, vai grupa-priekštece grupām Rj un R2 ; b2) pēc aizsarggrupas noņemšanas aminogrupai, iegūto savienojumu ar formulu: Rr IIc - riti- ch.
    pakļauj iedarbībai ar ortoskābes alkil- esteriem ar formulu R3C(OR)3 (10), kur R3 ir nozīmes, kuras uzrādītas savienojumam (I) izg.f.I. punktā, bet R ir alkil- CJ-C4: c2) ja vajadzīgs, iegūto savienojumu ar formulu : R R 5/ (caj rr R. ‘N 4 5 LV 10439 apstrādā ar Lavvesson'a reaktīvu: 2,4-bis-(4-metoksifenil)-I,3-ditia-2,4-difosfetān-2,4-disulfidu; d2) savienojumu, kas iegūts b2) vai c2) stadijās, ar formulu :
    apstrādā pēc tam apstākļos, kas piemēroti savienojuma (I) iegūšanai, pārvēršot grupas R'2 un/vai R'j attiecīgi par grupām R2 un/vai Rj.
  10. 10. Paņēmiens savienojuma (I) iegūšanai, atbilstoši izg.f.6. punktam, kas a t š ķ i r a s ar to, ka: a3) uz imidazola atvasinājumu ar formulu : R R
    N II ti kurā R3, R4, R5 ir nozīmes, kas uzrādītas savienojumam (I) izg.f.I. punkta, iedarbojas ar (4-difenilil)-metil- atvasinājumu ar formulu : R
    /T\
    \ / Hal - CH2 kurā Hal ir halogēna atoms, bet R'j un R'2 ir attiecīgi Rj un R2, vai grupu Rj un R2 grupas-priekšteces, skābekļa klātienē un bāziskā vidē, apstarojot ar UV-starojumu. b3) ja vajadzīgs, iepriekš iegūto savienojumu ar formulu: 4 6 a
    4' apstrādā ar Lawesson’a reaktīvu: 2,4-bis-(4-metoksifenil)-l,3-ditia-2,4-difosfenāt-2,4-disulfīdu; c3) savienoiumu. kas iegūts b3) vai c3) stadijās, ar formulu : r4
    a2c-Q-Ck, 5 a-j i apstrada pec tam apstaicļos, Kas piemerou savienojuma (I) iegūšanai, pārvēršot grupas R'2 un/vai R'j attiecīgi par grupām R2 un/vai Rj. II. Starpsavienojumi ar formulu R, Rr II —R. kurā: - R3 ir ūdeņradis, alkil- Cj-Cg, neaizvietots vai aizvietots ar vienu vai vairākiem halogēna atomiem, alkenil- C2-Cg, cikloalkil- C3-C7, fenil-, fenilalkil-, kurā alkil- ir ar CJ-C3, fenilalkenil-, kurā alkenil- ir ar C2-C3, uzrādītās fenilgrupas ir neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēna atomiem, alkil- CJ-C4, halogēnalkil- C1-C4, polihalogēnalkil- C1-C4, hidroksil- vai alkoksi- C1-C4; - R4 un R5 katrs, neatkarīgi viens no otra, ir alkil- Cj-Cg, fenil-, fenilalkil-, kurā alkil- ir ar C1-C3, uzrādītās alkil-, fenil- un fenilalkilgrupas ir neaizvietotas vai 7 LV 10439 aizvietotas ar vienu vai vairākiem halogēna atomiem vai vienu grupu, kura izvēlēta no perfluoralkil- C1-C4, hidroksil-, alkoksi- C1-C4 grupām ; - vai R4 un R5 kopā veido grupu ar formulu =CR7Rg, kurā R7 ir ūdeņradis, alkil- C1-C4 vai fenil-, bet Rg ir alkil- C1-C4 vai fenil-; - vaiar R4 un R5 kopā veido grupu ar formulu (CH2)n. vai grupu ar formulu (CH2)nY(CH2)q, kurā Y ir skābekļa atoms, vai sēra atoms, vai oglekļa atoms, aizvietots ar alku- C1.C4, fenil- vai fenilalkil-, kurā alkil- ir ar C1-C3, vai grupu N-R5, kurā Rg ir ūdeņradis, alkil- C1-C4, fenilalkil-, kurā alkil- ir ar C1-C3, alkilkarbonil- C1-C4, halogēnalkilkarbonil- C1-C4, polihalogēnalkilkarbonil- C1-C4, benzoil-, α-aminoacil- vai N-aizsarggrupa, vai R4 un R5 kopā ar oglekļa atomu, pie kura tie pievienoti veido indān- vai adamantān-; - P + q = m - n ir vesels skaitlis ar vērtībām no 2 līdz 11; - m ir vesels skaitlis ar vērtībām no 2 līdz 5; - X ir skābekļa atoms vai sēra atoms; - z un t ir nulle vai viens no indeksiem ir nulle, bet otrs ir viens; ar sekojošiem ierobežojumiem: - ja z un t ir nulle, bet X ir skābekļa atoms, tad R4 un R5 ir atšķirīgi no: . alkil-Cļ-Cg, fenil-, fenilalkil-, kurā alkil- ir ar C1-C3, uzrādītās alkil-, fenil-un fenilalkil- grupas ir neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēna atomiem vai ar grupu, kas izvēlēta no perfluoralkil- C1-C4, hidroksil- vai alkoksi-C1-C4 grupām; . vai R4 un R5, savienoti kopā, atšķiras no grupas N-Rg, kurā Rg ir ūdeņradis, alkil- C1-C4, fenilalkil-, kurā alkil- ir ar C1-C3; . n atšķiras no 6; - ja z = 1 un R3 ir fenil-, tad R4 un R5 katrs atšķiras no metil-.
  11. 12. Savienojums, atbilstoši izg.f. 11. punktam, ar formulu:
    H kurā X ir skābekļa atoms vai sēra atoms, bet R3 ir ūdeņradis, alkil- Cļ-Cg, neaizvietots vai aizvietots ar vienu vai vairākiem halogēna atomiem; alkenil- C2-Cg, cikloalkil- C3-C7, fenil-, fenilalkil-, kurā alkil- ir ar C1-C3, fenilalkenil-, kurā alkenil- ir ar C2-C3, uzrādītās fenilgrupas ir neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēnā atomiem, alkil- C1-C4, halogēnalkil- C4-C4, polihalogēnalkil-C1-C4, hidroksil- vai alkoksi- C4-C4 grupām.
  12. 13. Savienojums, atbilstoši izg.f. 11. punktam, ar formulu:
    H 01") 8 kurā R3, R4, R5 un X ir nozīmes, kuras uzrādītas savienojumam (11) izg.f.10. punktā.
  13. 14. Savienojums, atbilstoši izg.f. 11. punktam, ar formulu:
    H - R3 ir ūdeņradis, alkil- Cj-Cg, neaizvietots vai aizvietots ar vienu vai vairākiem halogēna atomiem, alkenil- Cļ-Cft, cikloalkil- C3-C7, fenil-, fenilalkil-, kurā alkil- ir ar C1-C3, fenilalkenil-, kurā alkenil- ir ar C2-C3, uzrādītās fenilgrupas ir neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēna atomiem, alkil- Cļ-C4, halogēnalkil- C1-C4, polihalogēnalkil- C1-C4, hidroksil- vai alkoksi- C1-C4 grupām; - R4 un R5 katrs, neatkarīgi viens no otra, ir alkil- Cļ-Cg, fenil-, fenilalkil-, kurā alkil- ir ar C1-C3, uzrādītās alkil-, fenil- un fenilalkil- grupas ir neaizvietotas vai aizvietotas ar vienu vai vairākiem halogēna atomiem vai ar grupu, kura izvēlēta no perfluoralkil- C1-C4, hidroksil-, alkoksi- C1-C4 grupām; - vai R4 un R5 kopā veido grupu ar formulu =CR7Rg, kurā R7 ir ūdeņradis, alkil-Cļ-C4 vai fenil-, bet Rg ir alkil- C4-C4 vai fenil-; - vai R4 un R5, kopā savienoti, ir grupa ar formulu (CH2)n* va* grupa ar formulu (CH2)pY(CH2>q, kurā Y ir skābekļa atoms, vai sēra atoms, vai oglekļa atoms, aizvietots ar alkil- C1-C4, fenil- vai fenilalkil-, kurā alkil- ir ar C1-C3, vai grupu N-Rg, kurā Rg ir ūdeņradis, alkil- C1-C4, fenilalkil-, kurā alkil- ir ar C1-C3, alkilkarbonil- CJ-C4, halogēnalkilkarbonil- C1-C4, polihalogēnalkilkarbonil- C1-C4, benzoil-, α-aminoacil- vai N-aizsarggrupa, vai R4 un R5, kopā ar oglekļa atomu, pie kura tie pievienot, veido indān- vai adamantān-; - p + q = m; - n ir vesels skaitlis ar vērtībām no 1 līdz 11; - m ir vesels skaitlis ar vērtībām no 2 līdz 5; - X ir skābekļa atoms vai sēra atoms; ar nosacījumu, ka R3 ir atšķirīgs no fenil-, ja R4 un R5 katrs ir metil-.
  14. 15. Paņēmiens savienojuma iegūšanai, atbilstoši kādam vienam no izg.f. 11-14 punktiem, kas a t š ķ i r a s ar to, ka - uz savienojumu ar formulu:
    n kura R4 un R5 ir aizvietotāji, kuri uzradīti savienojumam (11) izg.f.10. punktā, A ir OH grupa, NH2 grupa vai OR' grupa, kurā R' ir ūdeņradis vai alkil- C1-C4, 14 9 14 9LV 10439 - iedarbojas ar savienojumu, kura formula ir: R3 - B kurā R3 ir aizvietotāji, kuri uzrādīti savienojumam (11) izg.f.10. punktā, bet B ir: - grupa C(OR)3; NH - grupa C- OR; - vai grupa COHal; kur R ir alkil- C1-C4, bet Hal ir halogēna atoms, vēlams hlors; - pēc tam, ja vajadzīgs, iegūto savienojumu apstrādā ar Lawesson'a reaktīvu: 2,4-bis-(4-metoksifenil)-1,3-ditia-2,4-difosfetān-2,4-disulfīdu. 16. Ārstnieciskais sastāvs, kurš satur kā aktīvo vielu savienojumu, atbilstoši · kādam vienam no izg.f.1-7 punktiem. 17. Ārstnieciskais sastāvs, kurš satur savienojumu, atbilstoši kādam vienam no izg.f.1-7 punktiem, kopā atbloķējošu savienojumu. 18.. Ārstnieciskais sastāvs, kurš satur savienojumu, atbilstoši kādam vienam no izg.f. 1 -7 punktiem, kopā ar diurētsku līdzekli. 19. Ārstnieciskais sastāvs, kurš satur savienojumu, atbilstoši kādam vienam no izg.f.1-7 punktiem, kopā ar nesteroīdu pretiekaisuma savienojumu. 20. Ārstnieciskais sastāvs, kurš satur savienojumu, atbilstoši kādam vienam no izg.f.1-7 punktiem, kopā ar kalcija antagonistu. 21. Ārstnieciskais sastāvs, kurš satur savienojumu, atbilstoši kādam vienam no izg.f. 1-7 punktiem, kopā ar trankvilizatoru.
LVP-93-147A 1990-03-20 1993-02-25 N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions containing them LV10439B (en)

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FR9003563A FR2659967B1 (fr) 1990-03-20 1990-03-20 Derives d'imidazolinone n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
FR9010144A FR2665702B1 (fr) 1990-08-08 1990-08-08 Derives heterocycliques n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
PCT/FR1991/000224 WO1991014679A1 (fr) 1990-03-20 1991-03-20 Derives heterocycliques n-substitues, leur preparation, les compostions pharmaceutiques en contenant

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FI103407B (fi) 1999-06-30
NO914528D0 (no) 1991-11-19
HU913603D0 (en) 1992-07-28
ATE167475T1 (de) 1998-07-15
DE19975029I2 (de) 2002-05-08
IL97612A (en) 1995-08-31
IE910913A1 (en) 1991-09-25
NO301977B1 (no) 1998-01-05
SK280096B6 (sk) 1999-08-06
EP0454511B1 (fr) 1998-06-17
LU90371I2 (fr) 1999-05-12
UA42669A (uk) 2001-11-15
PL166581B1 (pl) 1995-06-30
IL110820A (en) 1995-11-27
CS74591A3 (en) 1991-11-12
FI103407B1 (fi) 1999-06-30
EP0454511A1 (fr) 1991-10-30
DE69129606D1 (de) 1998-07-23
DK0454511T3 (da) 1999-04-06
KR920702349A (ko) 1992-09-03
CA2057913A1 (en) 1991-09-21
NL980039I1 (nl) 1999-02-01
NL990006I1 (nl) 1999-05-03
HUT67648A (en) 1995-04-28
NO914528L (no) 1992-01-17
JPH04506222A (ja) 1992-10-29
SG49053A1 (en) 1998-05-18
NZ237476A (en) 1994-01-26
AU641005B2 (en) 1993-09-09
TW201738B (lv) 1993-03-11
WO1991014679A1 (fr) 1991-10-03
HK1008918A1 (en) 1999-05-21
PL165945B1 (pl) 1995-03-31
IL110820A0 (en) 1994-11-11
MX9203586A (es) 1992-07-01
CZ287064B6 (cs) 2000-08-16
NL980039I2 (nl) 1999-09-01
SK283197B6 (sk) 2003-03-04
ES2119764T3 (es) 1998-10-16
FI915458A0 (fi) 1991-11-19
KR0175310B1 (ko) 1999-02-18
LU90279I2 (fr) 1998-10-21
CA2057913C (en) 1997-07-08
MY115638A (en) 2003-08-30
NO1999025I1 (no) 1999-12-09
PL293015A1 (lv) 1993-02-08
HU9302497D0 (en) 1993-11-29
CZ287225B6 (cs) 2000-10-11
LV10439A (lv) 1995-02-20
HU223141B1 (hu) 2004-03-29
JP2868313B2 (ja) 1999-03-10
JPH10279566A (ja) 1998-10-20
PL166403B1 (pl) 1995-05-31
PT97078B (pt) 1997-07-31
HUT61284A (en) 1992-12-28
HU221188B1 (en) 2002-08-28
RU2099331C1 (ru) 1997-12-20
NL990006I2 (nl) 1999-10-01
AU7561091A (en) 1991-10-21
IL97612A0 (en) 1992-06-21
DE69129606T2 (de) 1998-12-17
NO1998021I1 (no) 1998-10-05
PT97078A (pt) 1991-11-29

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