LV10451B - Benzocycloheptenes, benzoxepines and benzothiepines and methods for preparation thereof - Google Patents
Benzocycloheptenes, benzoxepines and benzothiepines and methods for preparation thereof Download PDFInfo
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- LV10451B LV10451B LVP-94-154A LV940154A LV10451B LV 10451 B LV10451 B LV 10451B LV 940154 A LV940154 A LV 940154A LV 10451 B LV10451 B LV 10451B
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- pyridyl
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Claims (14)
- LV 10451 BENZOCIKLOHEPTĒNI, BENZOKSEPĪNI UN BENZOTIEPĪNI, TO IEGŪŠANAS METODES PATENTA FORMULA 1. Savienojumi ar vispārēju formulu:kurā: X simbolizē 0 vai CHR, kur R ir ūdeņraža atoms vai R, savienots ar Rit veido saiti, Rl, R2, R3 un R4, kas ir vienādi vai atšķirīgi, simbolizē ūdeņraža atomu vai Ci-C7-alkilgrupu; ir iespējams, ka Ri papildus veido saiti ar R; R5 simbolizē ūdeņraža atomu, hidroksilgrupu vai R5, savienots ar R7, veido saiti vai yO grupu; R6 simbolizē grupu ar formulu: ✓*10 "C^R RU kurā R10 un Rn, savienoti ar oglekļa atomu, kuram tie piesaistīti, veido neobligāti aromātisku mono- vai biciklisku slāpekli saturošu heterociklisku grupu ar 3 līdz 11 locekļiem, kas ietver 1 vai 2 slāpekļa atomus, neobligāti aizvietotu pie oglekļa atomiem ar 1 līdz 7 grupām, kas izvēlētas no hidroksil-, nitro-, ciano-, Ci-C7*alkil- vai Ci-C7-alkoksigrupām; ir iespējams, ka vismaz viens no heterocikla slāpekļa atomiem ir N-oksidēts; R7 simbolizē ūdeņraža atomu vai hidroksil-, Ci-C7-alkoksi- vai C1-C7--aciloksigrupu vai R5 un R7 kopā veido saiti vai >0 grupu; R8 un R9, kas ir vienādi vai atšķirīgi, simbolizē ūdeņraža vai halogēna atomu, hidroksil-, nitro-, ciano-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Cļ-C7-alkil-, Ci-C7-alkoksi-, Ci-C7-alkiltio-, C1-C7- 2 -aciltio-, Ci-C7-alkilsulfonil- vai Ci-C7-alkilsulfinilgrupu, grupu ar formulām: 0 0 O -C-OR12, -C-NR12R13 vai -C-R12 kurās R12 un R13, kas ir vienādi vai atšķirīgi, simbolizē ūdeņraža atomu vai Ci-C7-alkilgrupu, vai Re un R9 simbolizē Ce-Cio-aril-, (C6-Cio)arilsulfonil- vai (C6-Ci(y)arilsulfinilgrupu, neobligāti aizvietotu ar vienu līdz sešiem aizvietotājiem, kas izvēlēti no halogēna, hidroksil-, nitro-, ciano-, karboksil-, karbamoil-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Ci-C7-alkil-, C1-C7--alkoksi-, Ci-C7-alkiltio-, Ci-C7-aciltio-, Ci-C7-alkilsulfonil- vai Ci-C7-alkilsulfinilgrupām, vai Rg un Rg, kas ir vienādi vai atšķirīgi, simbolizē heterociklu ar 3 līdz 11 locekļiem gredzenā, ietverot 1 līdz 4 heteroatomus, kas ir vienādi vai atšķirīgi un izvēlēti no O, S un N, neobligāti aizvietotu ar vienu līdz sešiem aizvietotājiem, kas izvēlēti no halogēna, hidroksil-, nitro-, ciano-, karboksil-, karbamoil-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Ci-C7*alkil-, Ci-C7-alkoksi-, Ci-C7-alkiltio-, Ci-C7-aciltio-, Ci-C7-alkilsulfonil- vai C1-C7--alkilsulfinilgrupām, vai Rg un Rg kopā veido grupu (CH2)n> kur n ir skaitlis 1 līdz 6, vai Rg un Rg kopā veido heterociklu ar 3 līdz 11 locekļiem, ietverot 1 līdz 4 heteroatomus, kas ir vienādi vai atšķirīgi un izvēlēti no 0, S un N, neobligāti aizvietotu ar vienu līdz sešiem aizvietotājiem, kas izvēlēti no halogēna, hidroksil-, nitro-, ciano-, karboksil-, karbamoil-, trifluormetil-, trifluormetoksi-, pentafluoretil-, C1-C7-alkil-, Ci-C7-alkoksi-, Ci-C7-alkiltio-, Ci-C7-aciltio-, Ci-C7-alkil-sulfonil- vai C1-C7- alkilsulfinilgrupām, un to N-oksīdi, un to farmakoloģiski saderīgi sāļi.
- 2. Savienojumi ar vispārējo formulu I, saskaņā ar 1. punktu, atšķirīgi ar to, ka X simbolizē skābekļa atomu.
- 3. Savienojumi ar vispārējo formulu I, saskaņā ar 1. punktu, atšķirīgi ar to, ka Ri un R2 simbolizē ūdeņraža atomu. 3 LV 10451
- 4. Savienojumi ar vispārējo formulu I, saskaņā ar 1. punktu, atšķirīgi ar to, ka R5 simbolizē ūdeņraža atomu.
- 5. Savienojumi ar vispārējo formulu I, saskaņā ar 1. punktu, atšķirīgi ar to, ka Re ir izvēlēts no 2-piridilgrupas, 2-piridil-N-oksīda, 3-piridilgrupas, 3-piridil-N-oksīda, 4-piridilgrupas, 3-hidroksi-4--piridilgrupas, 2-pirimidilgrupas, 2-pirimidil*N-oksida, 6-pirimidil-grupas, 6-pirimidil-N-oksida, 2-hinolilgrupas, 2-hinolil-N-oksīda, 1-izohinolilgrupas un 1-izohinolil-N-oksīda, neobligāti aizvietotiem pie oglekļa atomiem ar 1 līdz 3 aizvietotājiem, kas izvēlēti no hidroksil-, nitro-, ciano-, Ci-C7-alkil- un Ci-C7-alkoksigrupām.
- 6. Savienojumi ar vispārējo formulu I, saskaņā ar 1. punktu, atšķirīgi ar to, ka R7 simbolizē ūdeņraža atomu vai hidroksil-, metoksi- vai acetoksigrupu.
- 7. Savienojumi, saskaņā ar 1. punktu, ar vispārēju formulu:II kurā X simbolizē 0 vai CHR, un R, R5, Re, R7, Re un Rg ir, kā noteikts 1. punktā.
- 8. Savienojumi, saskaņā ar 1. punktu, ar vispārēju formulu:kurā X simbolizē O vai CHR, un R, Ū6, R8 un Rg ir, kā noteikts 1. punktā. III 4
- 9. Savienojumi, saskaņā ar 1. punktu, atšķirīgi ar to, ka tie izvēlēti no savienojumiem: 3.3- dimetil-5-(2-piridil-N-oksīd)-7-trifluormetoksi-2,3-dihidro-l-benzo-ksepīns; 3.3- dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 7-fluor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 7- brom-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 8- brom-3,3,7-trimetil-5-(2-piridil*N-oksīd)-2,3-dihidro-l-benzoksepīns; 7-etil-3,3-dimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepins; 3.3- dimetil-5-(2-piridil-N-oksīd)-7-(l-metilpropil)-2,3-dihidro-l-benzo-k ksepins; 7dzopropil-3,3-dimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepins; 7- metoksi-3,3'dimetil-5-(2-piridil-N-oksTd)-2,3-dihidro-l-benzoksepīns; 3.3- dimetil-5-(2-piridil-N-oksīd)-7-metilsulfinil-2,3-dihidro-l-benzo-ksepīns; 3.3- dimetil-5-(2-piridil-N-oksīd)-7-metilsulfonil-2,3-dihidro-l-benzo-ksepīns; 3.3- dimetil-5-(2-piridil-N-oksid)-7-pentafluoretil-2,3-dihidro-l-benzo-ksepins; 3.3- dimetil-5-(2-piridil-N-oksīd)-7-trifluormetil-2,3-dihidro-l-benzo-ksepins; 8- brom-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 7- brom-3,3-dimetil-5-(3-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 3.3- dimetil-7-nitro-5-(4-nitro-2-piridil-N-oksīd)-2,3-dihidro-l-benzo-ksepīns; 3.3- dimetil-7-fenil-5-(2-piridil*N-oksīd)-2,3-dihidro-l-benzoksepīns; 8- ciano-3,3-dimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepins; 6.8- dihlor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 7.9- dihlor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 8.9- dihlor-3,3-dimetil-5-(2-piridil-N-oksīd)*2,3-dihidro-l-benzoksepīns; 7,8-dimetoksi-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzokse-pīns; 9- etil-7-fluor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīns; 7-hlor-8-fluor*3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzokse-pīns; 3.3- dimetil-5-(2-piridil-N-oksīd)-2,3,7,8,9,10-heksahidro-l-naftr2,3--bjoksepīns; 5 LV 10451 7.8- dihlor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepin-5--ols; 7- hlor-8-etil-3,3-dimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepins; un 8- brom-3,3-dimetil-l-(2-piridil-N-oksīd)-3H-benzo[f]-ciklohepta-l,4--diēns.
- 10. Savienojumi, saskaņā ar 1. punktu, atšķirīgi ar to, ka tie izvēlēti no savienojumiem: 7-hlor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepins; 3.3- dimetil-5-(2-piridil*N-oksīd)*7-trifluormetil-2,3-dihidro-l-benzo-ksepīns; 7- ciano-3,3-dimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepīns; 8- ciano-3,3-dimetil-l-(2-piridil-N-oksid)-4,5-dihidro-3H-benzo[f]ciklo-heptēns; 7.8- dihlor-3,3-dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepins; 7.8- diiluor-3,3-dimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepins; 7- ciano-3,3,8-trimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepins; 8- ciano-3,3,7-trimetil-5-(2-piridil-N-oksid)-2,3-dihidro-l-benzoksepīns; 3.3- dimetil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzoksepīn-7-karboksi-amīds; un 3.3- dimetil-7-fenilsulfonil-5-(2-piridil-N-oksīd)-2,3-dihidro-l-benzo-ksepīns.
- 11. Metode savienojumu ar vispārēju formulu I:kurā: 6 X simbolizē O vai CHR, kur R ir ūdeņraža atoms vai R, savienots ar Ri( veido saiti, Ri, R2, R3 un R4, kas ir vienādi vai atšķirīgi, simbolizē ūdeņraža atomu vai C1-C7 - alkilgrupu; ir iespējams, ka Ri papildus veido saiti ar R; R5 simbolizē ūdeņraža atomu, hidroksilgrupu vai R5, savienots ar R7, veido saiti vai X) grupu;Re simbolizē grupu ar formulu: kurā R10 un Rn, savienoti ar oglekļa atomu, kuram tie piesaistīti, veido neobligāti aromātisku mono- vai biciklisku slāpekli saturošu heterociklisku grupu ar 3 līdz 11 locekļiem, ietverot 1 vai 2 slāpekļa atomus, neobligāti aizvietotu pie oglekļa atomiem ar 1 līdz 7 grupām, kas izvēlētas no hidroksil-, nitro-, ciano·, Ci-C7-alkil- vai Cļ-C7-alkoksigrupām; ir iespējams, ka vismaz viens heterocikla slāpekļa atoms ir N-oksidēts; R7 simbolizē ūdeņraža atomu vai hidroksil-, Ci-C7-alkoksi- vai C1-C7--aciloksigrupu vai R5 un R7 kopā veido saiti vai >0 grupu; Re un Rg, kas ir vienādi vai atšķirīgi, simbolizē ūdeņraža vai halogēna atomu, hidroksil-, nitro-, ciano-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Ci-C7-alkil-, Ci-C7-alkoksi-, Ci-C7-alkiltio-, C1-C7--aciltio-, Ci-C7-alkilsulfonil- vai Ci-C7-alkilsulfmilgrupu, grupu ar formulām: O 0 0 O -C-OR12, -0-NRi2Rl3 vai -C-R12 kurās R12 un R13, kas ir vienādi vai atšķirīgi, simbolizē ūdeņraža atomu vai Ci-C7-alkilgrupu, vai Rs un Rg simbolizē Ce-Cio-aril-, (C6-Cio)arilsulfonil- vai (C6-Cio)arilsulfinilgrupu, neobligāti aizvietotu ar vienu līdz sešiem aizvietotājiem, kas izvēlēti no halogēna, hidroksil-, nitro-, ciano-, karboksil-, karbamoil-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Ci-C7-alkil-, C1-C7--alkoksi-, Ci-C7-alkiltio-, Ci-C7-aciltio-, Ci-C7-alkilsulfonil- vai C1 -C7-alkilsulfinilgrupām, LV 10451 vai Re un Rg, kas ir vienādi vai atšķirīgi, simbolizē heterociklu ar 3 līdz 11 locekļiem gredzenā, ietverot 1 līdz 4 heteroatomus, kas ir vienādi vai atšķirīgi un izvēlēti no 0, S un N, neobligāti aizvietotu ar vienu līdz sešiem aizvietotājiem, kas izvēlēti no halogēna, hidroksil-, nitro-, ciano-, karboksil-, karbamoil-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Ci-C7-alkil-, Cļ-C7-alkoksi-, Ci-C7-alkiltio-, Ci-C7-aciltio-, Ci-C7-alkilsulfonil- vai Ci-C7-alkil-sulfinilgrupām, vai Re un Rg kopā veido grupu (CH2)n, kur n ir skaitlis 1 līdz 6, vai R8 un Rg kopā veido heterociklu ar 3 līdz 11 locekļiem, ietverot 1 līdz 4 hetferoatomus, kas ir vienādi vai atšķirīgi un izvēlēti no 0, S un N, neobligāti aizvietotu ar vienu līdz sešiem aizvietotājiem, kas izvēlēti no halogēna, hidroksil-, nitro-, ciano-, karboksil-, karbamoil-, trifluormetil-, trifluormetoksi-, pentafluoretil-, Ci-C7-alkil-, Ci-C7-alkoksi-, Ci-C7-alkiltio-, Ci-C7-aciltio-, C1-C7 -alkilsulfonil-vai Ci-C7-alkilsulfinilgrupām, un to farmakoloģiski saderīgu sāļu un N-oksīdu iegūšanai, atšķirīga ar to, ka ietver: jebkuru: a) ketona ar vispārēju formulu IVIV kurāX, Ri, R2, R3 un R4 ir, kā noteikts iepriekš, unRs’, Rs' un Rg’ attiecīgi simbolizē neobligāti aizsargātas R5, Rs un R9 grupas, kā noteikts iepriekš, reakciju ar metālorganisku savienojumu ar vispārēju formulu: Re * Rm Vkurā Rg' simbolizē grupu ar formulu: 8 kurā Rio un Rn, savienoti ar oglekļa atomu, kuram tie ir piesaistīti, veido neobligāti aromātisku mono- vai biciklisku, slāpekli saturošu heterociklisku grupu ar 3 līdz 11 locekļiem, ieskaitot 1 vai 2 slāpekļa atomus, un neobligāti aizvietotu pie oglekļa atomiem ar 1 līdz 7 grupām, kas ir neobligāti aizsargātas, ja nepieciešams, un izvēlētas no hidroksil-, nitro-, ciano-, Ci*C7-alkil- vai Ci-C7-alkoksigrupām un b) aizsarggrupu atšķelšanu, lai iegūtu savienojumu ar vispārēju formulu VI:VI kurā X, Ri, R2, R3, R4, R5, R6, Rs un R$ ir, kā noteikts iepriekš; un neobligāti jebkuru: cl) tādā veidā iegūtā savienojuma ar vispārēju formulu VI reakciju ar reaģentu ar vispārēju formulu VII: VII Rl4-Y kurā R14 simbolizē Ci-C7-alkil- vai Ci-C7-acilgrupu un Y simbolizē atšķeļamo grupu, lai iegūtu savienojumu ar vispārējo formulu I, kurā R7 simbolizē attiecīgi Ci-C7-alkoksi- vai Ci-C7-aciloksigrupu; vai c2) savienojuma ar vispārējo formulu VI, kas iegūts pēc metodes b), dehidratēšanu skābes vai skābes hlorīda klātbūtnē, lai iegūtu savienojumu ar sekojošu vispārējo formulu I:I 9 LV 10451 kurā X, Rļ, R2, R3, R4, R5, R6, Rs un Rg ir, kā noteikts iepriekš; un neobligāti d) savienojuma ar formulu I, kas iegūts stadijā c2), reakciju ar peroksīdu, lai iegūtu savienojumu ar vispārējo formulu I, kurā R5 un R7 kopā veido >0 grupu; un neobligāti e) savienojuma ar vispārējo formulu VI, kas iegūts stadijā b), vai savienojuma ar vispārējo formulu I, kas iegūts stadijā cl), c2) vai d), reakciju ar oksidējošu aģentu, lai veidotu atbilstošu N-oksīda savienojumu; un/vai neobligāti f) savienojuma ar vispārēju formulu VI, kas iegūts stadijā b), vai savienojuma ar vispārējo formulu I, kas iegūts stadijā cl), c2) vai d), reakciju ar farmācijā izmantojamu neorganisku vai organisku skābi, lai veidotu atbilstošu sāli.
- 12. Farmaceitisks sastāvs, kas kā aktīvo sastāvdaļu satur savienojumu, saskaņā ar jebkuru no 1. līdz 10. punktiem.
- 13. Savienojumi ar formuluVIII kurā X, Ri, R2, R3, R4, R5, Re un R9 ir, kā noteikts 1. punktā.
- 14. Savienojumi, kas izvēlēti no sekojošiem savienojumiem: 4-fenoksi-3,3-dimetilbutānskābe; 4-(4-bromfenoksi)-3,3-dimetilbutānskābe; 4-(4-hlorfenoksi)-3,3-dimetilbutānskābe; 4-(4-fluorfenoksi)-3,3-dimetilbutānskābe; 4-(4-metilfenoksi)-3,3-dimetilbutānskābe; 4-(4-etilfenoksi)-3,3-dimetilbutānskābe; 4-(4-izopropilfenoksi)-3,3-dimetilbutānskābe; 4-[4-(l-metilpropil)fenoksi]-3,3-dimetilbutānskābe; 4-(4-metoksifenoksi)-3,3-dimetilbutānskābe; 10 4-(4-trifluormetoksifenoksi)-3,3-dimetilbutānskābe; 4-(4-metiltiofenoksi)-3,3-dimetilbutānskābe; 4-(4-fenilfenoksi)-3,3-dimetilbutānskābe; 4-(3-bromfenoksi)-3,3-dimetilbutānskābe; 4-(3,5-dihlorfenoksi)-3,3-dimetilbutānskābe; 4-(3,4-dihlorfenoksi)-3,3-dimetilbutānskābe; 4-(2,4-dihlorfenoksi)-3,3-dimetilbutānskābe; 4-(2,3-dihlorfenoksi)-3,3-dimetilbutānskābe; 4-(3,4-difluorfenoksi)-3,3-dimetilbutānskābe; 4-(3-hlor-4-fluorfenoksi)-3,3-dimetilbutānskābe; 4-(2-etil-4-fluorfenoksi)-3,3*dimetilbutānskābe; 4-(3,4-dimetoksifenoksi)-3,3-dimetilbutānskābe; 4-(4-brom-3-metilfenoksi)-3,3-dimetilbutānskābe; 4-(3-brom-4-metilfenoksi)-3,3-dimetilbutānskābe; 4-(5,6,7,8-tetrahidronaftiloksi)-3,3-dimetilbutānskābe; 4-[4(2-metilpropil)fenoksi]-3,3-dimetilbutānskābe; 4-(4-hlor-3-etilfenoksi)-3,3-dimetilbutānskābe; 4-(4-hlor-3-metilfenoksi)-3,3-dimetilbutānskābe; 4- (4-brom-3-hlorfenoksi)-3,3-dimetilbutānskābe; 5- (4-bromfenil)-3,3-dimetilpentānskābe; 5-(3,4-dihlorfenil)-3,3-dimetilpentānskābe; 5-(4-bromfenil)-4,4-dimetilpentānskābe;
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FR9214720A FR2698873B1 (fr) | 1992-12-07 | 1992-12-07 | Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant. |
PCT/EP1993/003445 WO1994013658A2 (en) | 1992-12-07 | 1993-12-07 | Benzocycloheptenes, benzoxepines and benzothiepines |
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US6642268B2 (en) | 1994-09-13 | 2003-11-04 | G.D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors |
US5994391A (en) * | 1994-09-13 | 1999-11-30 | G.D. Searle And Company | Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
US6107494A (en) * | 1994-09-13 | 2000-08-22 | G.D. Searle And Company | Substituted 5-aryl-benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
US6262277B1 (en) | 1994-09-13 | 2001-07-17 | G.D. Searle And Company | Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
DK0781278T3 (da) * | 1994-09-13 | 2001-04-17 | Monsanto Co | Nye benzothiepiner, som har aktivitet som inhibitorer af ileal galdsyretransport og taurocholatoptagelse |
US6268392B1 (en) | 1994-09-13 | 2001-07-31 | G. D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors |
US5952326A (en) * | 1997-12-10 | 1999-09-14 | Pfizer Inc. | Tetralin and chroman derivatives useful in the treatment of asthma, arthritis and related diseases |
US6221897B1 (en) | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
WO2000038721A1 (en) * | 1998-12-23 | 2000-07-06 | G.D. Searle Llc | Combinations of cholesteryl ester transfer protein inhibitors and nicotinic acid derivatives for cardiovascular indications |
ES2200587T3 (es) | 1998-12-23 | 2004-03-01 | G.D. Searle Llc | Combinaciones de inhibidors del transporte de acidos biliares del ileon e inhibidores de la proteina de transferencia de colesteril ester para indicaciones cardiovasculares. |
EP1140187B1 (en) * | 1998-12-23 | 2003-09-03 | G.D. Searle LLC. | Combinations of an ibat inhibitor and a mtp inhibitor for cardiovascular indications |
AU2157400A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle & Co. | Combinations of cholesteryl ester transfer protein inhibitors and hmg coa reductase inhibitors for cardiovascular indications |
US6569905B1 (en) | 1998-12-23 | 2003-05-27 | G.D. Searle, Llc | Combinations of cholesteryl ester transfer protein inhibitors and bile acid sequestering agents for cardiovascular indications |
JP2002533414A (ja) | 1998-12-23 | 2002-10-08 | ジー.ディー.サール エルエルシー | 心臓血管に適用するための回腸胆汁酸輸送阻害剤および胆汁酸隔離剤の組み合わせ |
DE69907960T2 (de) * | 1998-12-23 | 2004-02-26 | G.D. Searle Llc, Chicago | Kombinationen von ileumgallensäuretransports inhibitoren und fibronsäure derivaten für kardiovaskuläre indikationen |
EA009466B1 (ru) | 1998-12-23 | 2007-12-28 | Джи.Ди. Сирл Ллс | Ингибитор белка, переносящего эфир холестерила |
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US6852753B2 (en) | 2002-01-17 | 2005-02-08 | Pharmacia Corporation | Alkyl/aryl hydroxy or keto thiepine compounds as inhibitors of apical sodium co-dependent bile acid transport (ASBT) and taurocholate uptake |
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-
1992
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- 1993-12-07 AT AT94902708T patent/ATE177742T1/de not_active IP Right Cessation
- 1993-12-07 RU RU94040853A patent/RU2127268C1/ru active
- 1993-12-07 US US08/284,454 patent/US5602152A/en not_active Expired - Fee Related
- 1993-12-07 DE DE69324001T patent/DE69324001T2/de not_active Expired - Fee Related
- 1993-12-07 RO RO94-01321A patent/RO113040B1/ro unknown
- 1993-12-07 WO PCT/EP1993/003445 patent/WO1994013658A2/en not_active Application Discontinuation
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- 1993-12-07 JP JP6513771A patent/JPH07503977A/ja active Pending
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- 1993-12-07 AU AU56975/94A patent/AU680856B2/en not_active Ceased
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