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SI9210101B - Imidazole,triazole and tetrazole derivates. - Google Patents

Imidazole,triazole and tetrazole derivates. Download PDF

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Publication number
SI9210101B
SI9210101B SI9210101A SI9210101A SI9210101B SI 9210101 B SI9210101 B SI 9210101B SI 9210101 A SI9210101 A SI 9210101A SI 9210101 A SI9210101 A SI 9210101A SI 9210101 B SI9210101 B SI 9210101B
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indol
formula
group
ylmethyl
ethylamine
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SI9210101A
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SI9210101A (en
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Raymond Baker
Victor G Matassa
Leslie J Street
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Merck Sharp & Dohme
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Priority claimed from GB919102222A external-priority patent/GB9102222D0/en
Priority claimed from GB919106917A external-priority patent/GB9106917D0/en
Priority claimed from GB919113415A external-priority patent/GB9113415D0/en
Priority claimed from GB919122451A external-priority patent/GB9122451D0/en
Application filed by Merck Sharp & Dohme filed Critical Merck Sharp & Dohme
Publication of SI9210101A publication Critical patent/SI9210101A/sl
Publication of SI9210101B publication Critical patent/SI9210101B/sl

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    • 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
    • C07D401/06—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 only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Claims (8)

  1. -1- PATENTNI ZAHTEVKI 1. Postopek za pripravo spojine s formulo I, ali njene soli ali predzdravila: A
    (I) v kateri črtkani krog pomeni dve nesosednji dvojni vezi na kateremkoli položaju petčlenskega obroča; dva, tri ali štiri od V, W, X, Y in Z pomenijo dušik, ostali pa ogljik, če so, kadar dva od V, W, X, Y in Z pomenita dušik in ostali ogljik, omenjeni atomi dušika na nesosednjih položajih v petčlenskem obroču; A1 pomeni vodik, metil, etil, benzil, ali amino; A2 pomeni nevezani elektronski par, kadar štirje od V, W, X, Y in Z pomenijo dušik in drugo pomeni ogljik; ali, kadar dva ali trije od V, W, X, Y in Z pomenijo dušik, in preostanek pomeni ogljik, pomeni A2 pomeni vodik, metil, etil, benzil ali amino; E pomeni vez ali nerazvejano ali razvejano alkilensko verigo, ki vsebuje 1 do 4 atome ogljika; F pomeni skupino s formulo R
  2. 2. Postopek po zahtevku 1, označen s tem, da omogoča pripravo spojine, ki jo predstavlja formula IIA, in njene soli, oziroma predzdravila:
    (I IA) v kateri X1 pomeni dušik ali A12-C; n je ničla, 1, 2 ali 3; B1 pomeni kisik, žveplo ali N-R13; A11 in A12 neodvisno pomenita vodik, metil, etil, benzil ali amino; in R12, R13, R14, R16 in R17 neodvisno pomenijo vodik ali Ci-6 alkil.
    -2- U pomeni dušik ali C-R2; B pomeni kisik, žveplo ali N-R3; R1 pomeni -CH2.CHR4.NR6R7 ali skupino s formulo
    v kateri pretrgana črta pomeni poljubno kemično vez; in R2, R3, R4, R5, R6 in R7 neodvisno pomenijo vodik ali Ci_6 alkil, označen s tem, da obsega: (A) presnovo reaktivnega derivata karboksilne kisline s formulo Ra-C02H, s spojino bodisi s formulo III bodisi s formulo IV, ali njeno soljo: .NHRbN II Rc/ ^NH2 (III) N NH2
    NHRb (IV) v kateri je ena od Ra, Rb in Rc skupina s formulo A1, druga je skupina s formulo A2, tretja pa je skupina s formulo -E-F, kot je določeno zgoraj; ali (B) reakcijo spojine s formulo XIV: W vα E-F M Ηα I γ°—Za (XIV) v kateri so A1, E in F kot so določeni zgoraj, Hal pomeni halogen in dve od Va, W\ X\ Ya ter Za, za eno od njih je vezana skupina Hal, pomenita ogljik, ostale pa dušik, z reagentom, ki daje anion -A2, kjer je A2 kot je določeno zgoraj; ali -3- (C) cikloadicijo alkina s formulo Ra-C=C-Rb z azidom s formulo Rc-N3, kjer so Ra, Rb in Rc kot so določeni zgoraj; ali (D) cikloadicijo nitrila s formulo N=C-Rd z azidom s formulo Re-N3, kjer eden od Rd in Re pomeni skupino s formulo A1, drugi je pa skupina s formulo -E-F, kot je določeno zgoraj; ali (E) reakcijo spojine s formulo Re-L z derivatom tetrazola s fomulo XV:
    v kateri ena od Rd in Rc pomeni skupino s formulo A1 in druga je skupina s formulo -E-F, kot je določeno zgoraj, L pa pomeni primerno izstopajočo skupino, v prisotnosti baze; ali (F) cikloadicijo nitrila s formulo N=C-E-F, kjer sta E in F kot je določeno zgoraj, z natrijevim azidom, nakar sledi nakisanje z anorgansko kislino; ali (G) reakcijo spojine s formulo XVI:
    (XVI ) v kateri so V, W X, Y, Z, A1, A2 in E kot je določeno zgoraj, s spojino s formulo VII ali njeno karbonil-zaščiteno obliko: 0
    (vil) -4- kjer je R2 kot je določeno zgoraj in R11 ustreza skupini R1 kot je določeno zgoraj, ali pa pomeni skupino s formulo -CH2.CHR4D', v kateri je R4 kot je določeno, D1 pa pomeni skupino, ki se brez težav zamenja; temu sledi, tam kjer je potrebno, N-alkiliranje s stanardnimi metodami, da se vstavi skupina R3; ali (H) ciklizacijo spojine s formulo XXII;
    v kateri V, W, X, Y, Z, A1, A2, E in R1 kot je določeno v zahtevku 1, D2 pa pomeni skupino, ki se brez težav zamenja; temu sledi, tam kjer je potrebno, N-alkiliranje s standardnimi metodami, da se vstavi skupina R3; ali (J) ciklizacijo spojine s formulo XXV:
    v kateri so V, W, X, Y, Z, A1, A2, E in R2 kot je določeno zgoraj, Ba pomeni kisik ali žveplo in R21 ustreza skupini R1, kot je definirana zgoraj, ali pa razen tega pomeni prekursorsko skupino; temu sledi kjer je potrebno, pretvorba skupine R21 v želeno skupino R1; in (K) naknadno, kjer primerno, pretvorbo spojine s formulo I, ki je prvotno pridobljena, v nadaljnjo spojino s formulo I, z običajnimi metodami. -5-
  3. 3. Postopek po zahtevku 1, označen s tem, da omogoča pripravo spojine, ki jo predstavlja formula IIB, ter njene soli in predzdravila:
    (IIB) v kateri Υ1 pomeni dušik ali A22-C; n je ničla, 1, 2 ali 3; B2 pomeni kisik, žveplo ali N-R23; A21 in A22 neodvisno pomenita vodik, metil, etil ali benzil; in R22, R23, R24, R26 in R27 neodvisno pomenijo vodik ali C|.o alkil. -6-
  4. 4. Postopek po zahtevku 1 , označen s tem, da omogoča pripravo spojine, ki jo predstavlja formula IIC, ter njene soli, oziroma predzdravila:
    (1IC) v katerih Y2 pomeni dušik ali A32-C; Z1 pomeni dušik ali CH; n je ničla, 1, 2 ali 3; B3 pomeni kisik, žveplo ali N-R33. A31 in A32 neodvisno pomenita vodik, metil ali amino; R31 pomeni -CH2.CHR34.NR36R37 ali skupino s formulo
    in R32, R33, R34, R35, R36 in R37 neodvisno pomenijo vodik ali Ci^alkil.
  5. 5. Postopek po zahtevku 1, označen s tem, da omogoča pripravo spojine, ki jo predstavlja formula IID, ter njene soli, oziroma predzdravila:
    (IID) v kateri W! pomeni dušik ali C-A42; n je ničla, 1, 2 ali 3; B4 pomeni kisik, žveplo ali N-R43. A41 in A42 neodvisno pomenita vodik ali metil; R41 pomeni -CH2.CHR44.NR46R47 ali skupino s formulo -7-
    R42, R43, R44, R45, R46 in R47 neodvisno pomenijo vodik ali Ci-6 alkil.
  6. 6. Postopek po zahtevku 1, označen s tem, da omogoča pripravo spojin izbranih izmed: 2-[5-(2-benziltetrazol-5-ilmetil)-l H-indoI-3-il]etilamin; 2- [5-(l-benziltetrazol-5-ilmetil)-l H-indoI-3-Π]etilamin; N,N-dimetil-2-[5-(l-metiItetrazol-5-iImetil)-l H-indol-3-il]etiIamin; N,N-dimetil-2-[5-(2-metiItetrazol-5-ilmetii)-l H-indol-3-il]etiiamin; N,N-dimetil-2-[5-(l,2,4-triazol-l-ilmetil)-l H-indol-3-il]etilamin; N,N-dimetil-2-[5-(tetrazol-2-ilmetil)-l H-indol-3-il jetilamin; N, N-dimetiI-2-[5-(tetrazol-l-ilmetil)-l H-indol-3-il]etilamin; N, N-dimetil-2-[5-(l-metil-l,2,4-triazol-5-ilmetil)-l H-indoI-3-il]etilamin; N,N-dimetil-2-[5-(l-metil-l,2,4-triazol-3-ilmetil)-l H-indol-3-il]etilamin; N, N-dimetil-2-[5-(l,2,3-triazol-l-ilmetil)-l H-indol-3-il]etilamin; 3- (2-aminoetil)-5-(l-metiltetrazol-5-il)-benzo[b]tiofen; 3-(2-aminoetil)-5-(2-metiltetrazol-5-il)-benzo[b]tiofen; 3- [2-(N,N-dimetilamino)etil]-5-(2-metiltetrazol-5-il)benzo[b]tiofen; N,N-dimetil-2-[5-(2-metiIimidazol-l-ilmetil)-lH-indol-3-il]etilamin; N,N-dimetil-2- [5-(imidazol-l -ilmetil)-l H-indol-3-Π] etilamin; N,N-dimetil-2-[5-(2-metiIimidazol-l-il)-lH-indol-3-il]etilamin; N,N-dimetil-2-(5-(2-etiltetrazol-5-ilmetil)-lH-indol-3-il]etilamin; N,N-dimetil-2-[5-(l-etiltetrazol-5-ilmetil)-lH-indol-3-il]etilamin; N,N-dimetil-2-[5-(l,2,4-triazol-l-il)-lH-indol-3-il)etilamin; l-metil-4-(5-(2-metilimidazol-l-iI)-lH-indol-3-il]piperidin; l-metil-4-[5-(l,2,4-triazol-l-ilmetil)-lH-indol-3-il]piperidin; 4- [5-(2-metilimidazol-l-il)-l H-indol-3-il]piperidin; 4-[5-(l,2,4-triazol-l-ilmetil)-lH-indol-3-il]piperidin; 3- [5-(2-metilimidazol-l-il)-lH-indol-3-il]pirolidin; l-metil-3-[5-(2-metilimidazol-l-il)-lH-indol-3-il]pirolidin; 4- [5-(imidazol-l-il)-lH-indol-3-il]piperidin; -8- 4-[5-(l,2,3-triazoI-l-iI)-lH-indoI-3-il]piperidin; l-metil-4- [5-(imidazol-l-il)-l H-indoI-3-Π] piperidin; l-metil-4-[5-(l,2,3-triazol-l-ii)-lH-indol-3-il]piperidin; l-metiI-3-[5-(l,2,3-triazol-l-iI)-lH-indol-3-il]pirolidin; l-metiI-3- [5-(2-metilimidazol-l -ilmetil)-l H-indoI-3-Π] pirolidin; l-metiI-3-[5-(imidazol-l-il)-l H-indol-3-il]piroIidin; l-metil-3-[5-(l,2,4-triazoI-l-ilmetil)-lH-indol-3-il]pirolidin; l-metil-3-[5-(imidazol-l-ilmetil)-lH-indol-3-iI]piroIidin; N,N-dimetil-2-[5-(2-aminoimidazol-l-il)-lH-indol-3-iI]etilamin; N,N-dimetiI-2-[5-(2-aminoimidazoI-l-ilmetiI)-lH-indoI-3-il]etilamin; N-metil-2-[5-(l,2,4-triazol-l-iImetil)-lH-indol-3-il]etiIamin; in njihovih soli ter predzdravil.
  7. 7. Postopek za izdelavo farmacevtskega sestavka, označen s tem, da obsega mešanje spojine, kot je opisano v vsakem od predhodnih zahtevkov, s farmacevtsko sprejemljivim nosilcem ali ekscipientom.
  8. 8. Uporaba spojine po kateremkoli od zahtevkov 1 do 6, za izdelavo zdravila za zdravljenje in/ali preprečitev kliničnih stanj za katere je indiciran selektivni agonist 5-HTj -podobnih receptorjev. Za Merck Sharp & Dohme Ltd. Velika Britanija:
SI9210101A 1991-02-01 1992-01-30 Imidazole,triazole and tetrazole derivates. SI9210101B (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB919102222A GB9102222D0 (en) 1991-02-01 1991-02-01 Therapeutic agents
GB919106917A GB9106917D0 (en) 1991-04-03 1991-04-03 Therapeutic agents
GB919113415A GB9113415D0 (en) 1991-06-21 1991-06-21 Therapeutic agents
GB919122451A GB9122451D0 (en) 1991-10-23 1991-10-23 Therapeutic agents
YU10192A YU48236B (sh) 1991-02-01 1992-01-30 Postupak za dobijanje derivata imidazola, triazola i tetrazola

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SI9210101A SI9210101A (en) 1996-08-31
SI9210101B true SI9210101B (en) 2001-06-30

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SI9210101A SI9210101B (en) 1991-02-01 1992-01-30 Imidazole,triazole and tetrazole derivates.

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Families Citing this family (123)

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Publication number Priority date Publication date Assignee Title
MC2210A1 (fr) * 1990-06-07 1992-11-26 Wellcome Found Composes heterocycliques therapeutiques,leur utilisation et procede pour les preparer
US5578612A (en) * 1990-10-15 1996-11-26 Pfizer Inc. Indole derivatives
US5545644A (en) * 1990-10-15 1996-08-13 Pfizer Inc. Indole derivatives
US5559129A (en) * 1990-10-15 1996-09-24 Pfizer Inc Indole derivatives
US5559246A (en) * 1990-10-15 1996-09-24 Pfizer Inc. Indole derivatives
US5607951A (en) * 1990-10-15 1997-03-04 Pfizer Inc Indole derivatives
JPH06509574A (ja) * 1991-08-03 1994-10-27 スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー ５−ｈｔ↓４レセプターアンタゴニスト
GB9201038D0 (en) * 1992-01-16 1992-03-11 Glaxo Group Ltd Chemical compounds
TW288010B (sl) * 1992-03-05 1996-10-11 Pfizer
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