LV12273B - Jauns paņēmiens 7-(aizvietota)-9-[(aizvietota glicil)amido]-6-dimetil-6-deoksitetraciklīnu ražošanai - Google Patents

Jauns paņēmiens 7-(aizvietota)-9-[(aizvietota glicil)amido]-6-dimetil-6-deoksitetraciklīnu ražošanai Download PDF

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LV12273B
LV12273B LVP-99-19A LV990019A LV12273B LV 12273 B LV12273 B LV 12273B LV 990019 A LV990019 A LV 990019A LV 12273 B LV12273 B LV 12273B
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amino
methylpropyl
butyl
substituted
methyl
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Phaik-Eng Sum
Ving J. Lee
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American Cyanamid Company
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
    • C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines

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Claims (8)

  1. LV 12273 FORMULA 1. Iegūšanas paņēmiens 7-(aizvietota)-9-[(aizvietota glicil)amino]-6-demetil-6-deoksitetraciklīniem ar formulu:
    kur: X ir izvēlēts no rindas: aminogrupa, -NR1R2, vai halogēns; halogēns ir izvēlēts no rindas: broms, hlors, fluors vai jods; un kad X = -NR1R2 un R1 = ūdeņradis, R2 = metil-, etil-, n-propil-, 1-metiletil-, n-butil-, 1-metilpropil-, 2-metilpropil- vai 1,1-dimetiletilgrupa; un kad R1= metil- vai etilgrupa, R2 = metil-, etil-, n-propil-, 1-metiletil-, n-butil-, 1-metilpropil-vai 2- metilpropilgrupa; un kad R1= n-propilgrupa, R2 = n-propil-, 1-metiletil-, n-butil-, 1-metilpropil-vai 2-metilpropilgrupa; un kad R1= 1-metiletilgrupa, R2 = n-butil-, 1-metilpropil- vai 2-metilpropilgrupa; un kad R1= n-butilgrupa, R2 = n-butil-, 1-metilpropil- vai 2-metilpropilgrupa; un kad R1= 1-metilpropilgrupa, R2 = 2-metilpropilgrupa; R irlzvēlēts no R4(CH2)nCO-, n=0-4; un kad n=0, R4 ir izvēlēts no rindas: α-aminometil-, a-aminoetil-, α-aminobutil-, a-aminoizobutilgrupa un minētās grupas enantiomēriem; un kad n=1-4, 2 R4 ir izvēlēts no rindas: amino-, metilamino-, etilamino-, n-propilamino-, 1-metiletilamino-, n-butilamino-, 1-metilpropilamino-, 2-metilpropilamino-, 1,1-dimetiletilamino-, n-pentilamino-, 2-metilbutilamino-, 1,1-dimetilpropilamino-, 2,2-dimetilpropilamino-, 3-metilbutilamino-, n-heksilamino-, 1-metilpentilamino-, 1,1-dimetilbutilamino-, 2,2-dimetilbutilamino-, 3-metilpentilamino-, 1,2-dimetilbutilamino-, 1,3-dimetilbutilamino- un 1-metil-2-etilpropilamino-, ciklopropilamino-, ciklobutilamino-, benzilamino- un fenilamino-, dimetilamino-, dietilamino-, metil(butil)amino-, etil(1 -metiletil)amino-, monometilbenzilamino-, aziridinil-, azetidinil-, pirolidinil-, 2-metilpirolidinil-, piperidinil-, morfolinil-, imidazolil-, 1-pirolil-, 1-(1,2,3-triazolil)- un 4-(1,2,4-triazolil)grupa, aminoetiķskābe, α-amino-propionskābe un minētās grupas enantiomēriem, kas ietver: (a) 9-amino-7-(aizvietota)-6-demetil-6-deoksitetraciklīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls sajaukšanu ar polāru, aprotonu šķīdinātāju, inertu šķīdinātāju, bāzi un piedalīšanos reakcijā ar lineāru vai sazarotu haloacil-halogēnsavienojumu ar formulu: O
    kur: Q ir halogēns [izvēlēts no rindas: broms, hlors, fluors vai jods]; un kad n=0, Y ir lineāra vai sazarota a-halo(Cļ-C4)alkilgrupa, kas izvēlēta no rindas: bromometil-, hlorometil-, jodometil-, a-bromoetil-, a-hloroetil-, a-bromobutil- un a-hloro-izobutilgrupa; un kad n = 1-4, 3 3 LV 12273 Y ir halogēns, kas izvēlēts no rindas: broms, hlors, jods un fluors; O-toluolsulfonāts; O-metilsulfonāts vai trifluorometilsulfonāts; 0,5 līdz 5 stundu laikā temperatūru intervālā no istabas temperatūras līdz reaģējošā maisījuma viršanas temperatūrai un 9-[(haloacil)amino]-7-(aizvietota)-6-demetil-6-deoksitetraciklīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls izdalīšanu; un (b) gadījumā, ja n = 1-4, 9-[(haloacil, o-toluolsulfonilacil, o-metilsulfonilacil vai o-trifluorometilsuifonilacil)amino]-7-(aizvietota)-6-demetil-6-deoksitetraciklīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls reakciju polārā, aprotonā šķīdinātājā, hēlija, slāpekļa vai argona inertā atmosfērā ar nukleofilu reaģentu, kura formula ir R4H, kur R4 ir definēts iepriekš vai, gadījumā, ja n = 0, 9-[(haloacil)amino]-7-(aizvietota)-6-demetil-6-deoksitetraciklīna piedalīšanos reakcijā ar amonjaku tādos pat apstākļos; no 0,5 līdz 2 stundu laikā temperatūru intervālā no istabas temperatūras līdz reaģējošā maisījuma viršanas temperatūrai un savienojuma ar formulu I vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls izdalīšanu.
  2. 2. Paņēmiens saskaņā ar 1. punktu, kur: X ir izvēlēts no rindas: aminogrupa, -NR1R2, vai halogēns; halogēns ir izvēlēts no rindas: broms, hlors, fluors un jods; un kad X = -NR1R2, un kad R1 = metil- vai etilgrupa, R2 = metil- vai etilgrupa, R ir izvēlēts no R4(CH2)nCO-, n=0-4, un kad n = 0, R4 ir izvēlēts no rindas: a-aminometil-, α-aminoetil-, a-aminobutilgrupa un minētās grupas enantiomēriem; un kad n=1-4, 4 R4 ir izvēlēts no rindas: amino-, metilamino-, etilamino-, n-propilamino-, 1-metiletilamino-, n-butilamino-, n-pentilamino- un n-heksilamino-, ciklopropilamino- un benzilamino-, dimetilamino-, dietilamino-, metil(butil)amino-, azetidinil-, pirolidinil-, piperidinil-, morfolinil- un imidazolilgrupa; un farmaceitiski pieņemami organiski vai neorganiski sāļi.
  3. 3. Iegūšanas paņēmiens 7-(aizvietota)-9-[(aizvietota glicil)amino]-6-demetil-6-deoksitetraciklīniem ar formulu:
    kur X ir dimetilaminogrupa un R ir izvēlēts no: i un -CO-CH-N-CH, \ CH3 CH, -CO-CH-NH-OL i 3 CH, kas ietver: (a) 9-amino-7-(dimetilamino)-6-demetil-6-deoksitetracikiīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls samaisīšanu ar polāru, aprotonu šķīdinātāju, inertu šķīdinātāju, bāzi un piedalīšanos reakcijā ar 2-bromo-propionil bromīdu 0,5 līdz 5 stundas temperatūru intervālā no istabas temperatūras līdz reaģējošā maisījuma viršanas temperatūrai un 9-[(2-bromo-1-oksopropil)-amino]-7-(aizvietota)-6-demetil-6-deoksitetraciklīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls izdalīšanu; un 5 5 LV 12273 (b) 9-[(2-bromo-1-oksopropil)-amino]-7-(aizvietota)-6-demetil-6-deoksitetraciklīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls reakciju polārā, aprotonā šķīdinātājā, hēlija, slāpekļa vai argona inertā atmosfērā ar dimetilamīnu vai metilamīnu; no 0,5 līdz 2 stundu laikā temperatūru intervālā no istabas temperatūras līdz reakcijas atteces temperatūrai un reakcijas produkta vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls izdalīšanu.
  4. 4. Iegūšanas paņēmiens jauniem lineāriem vai sazarotiem 9- [(haloacil)amino]-7-(aizvietota)-6-demetil-6-deoksitetraciklīniem ar formulu:
    kur: X ir izvēlēts no rindas: aminogrupa, -NR1R2, vai halogēns; halogēns ir izvēlēts no rindas: broms, hlors, fluors un jods; un kad X = -NR1R2 un R1 = ūdeņradis, R2 = metil-, etil-, n-propil-, 1-metiletil-, n-butil-, 1-metilpropil-, 2-metilpropil- vai 1,1-dimetiletilgrupa; un kad R1 = metil- vai etilgrupa, R2 = metil-, etil-, n-propil-, 1-metiletil-, n-butil-, 1-metilpropil- vai 2- metilpropilgrupa; un kad R1= n-propilgrupa, R2 = n-propil-, 1-metiletil-, n-butil-, 1-metilpropil-vai 2-metilpropilgrupa; un kad R1= 1-metiletilgrupa, R2 = n-butil-, 1-metilpropil- vai 2-metilpropilgrupa; 6 un kad R1= n-butilgrupa, R2 = n-butil-, 1-metilpropil- vai 2-metilpropilgrupa; un kad R1= 1-metilpropilgrupa, R2 = 2-metilpropilgrupa; un kad n=0, Y ir lineāra vai sazarota a-halo(Ci-C4)alkilgrupa, kas izvēlēta no rindas: bromometil-, hlorometil-, jodometil-, α-bromoetil-, a-hloroetil-, a-bromobutil- un a-hloro-izobutilgrupa; un kad n = 1-4, Y ir halogēns, kas izvēlēts no rindas: broms, hlors, jods un fluors; O-toluolsulfonāts; O-metilsulfonāts vai trifluorometilsulfonāts; kas ietver (a) 9-amino-7-(aizvietota)-6-demetil-6-deoksitetraciklīna vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls samaisīšanu ar polāru, aprotonu šķīdinātāju, inertu šķīdinātāju, bāzi un piedalīšanos reakcijā ar lineāru vai sazarotu haloacil-halogēnsavienojumu ar formulu: O
    kur Y, n un Q ir definēti iepriekš; 0,5 līdz 5 stundu laikā temperatūru intervālā no istabas temperatūras līdz reaģējošā maisījuma viršanas temperatūrai un savienojuma ar formulu II vai tā farmaceitiski pieņemamas organiskas vai neorganiskas sāls izdalīšanu.
  5. 5. Paņēmiens saskaņā ar 4. punktu, kur X ir izvēlēts no rindas: aminogrupa, -NR1R2, vai halogēns; halogēns ir izvēlēts no rindas: broms, hlors, fluors un jods; un kad X = -NR1R2, 7 7 LV 12273 un kad R1 = metil- vai etilgrupa, R2 = metil- vai etilgrupa, un kad n = 0, Y ir lineāra vai sazarota a-halo(Ci-C4)alkil grupa, kas izvēlēta no rindas: bromometil-, hlorometil-, jodometil-, α-bromoetil-, a-hloroetil-, a-bromobutil- un a-hloro-izobutilgrupa; un kad n = 1-4, Y ir halogēns, kas izvēlēts no rindas: broms, hlors, jods un fluors; O-toluolsulfonāts; O-metilsulfonāts vai trifluorometilsulfonāts; un farmaceitiski pieņemama organiska vai neorganiska sāls.
  6. 6. Paņēmiens saskaņā ar jebkuru no 1 līdz 5 punktiem, kur minētais polārais, aprotonais šķīdinātājs ir izvēlēts no rindas: 1,3-dimetil-3,4,5,6-tetrahidro- 2(1 H)-pirimidons, 1,3-dimetil-2-imidazolidinons, heksametilfosforamīds, dimetilformamīds, dimetilacetamīds, N-metilpirolidons, 1,2-dimetoksietāns, tetrahidrofurāns, ūdens, metanols un to ekvivalents.
  7. 7. Paņēmiens saskaņā ar jebkuru no 1 līdz 5 punktiem, kur minētais inertais šķīdinātājs ir izvēlēts no rindas: acetonitrils, metilēnhlorīds, tetrahidrofurāns, hloroforms, tetrahlorogleklis, 1,2-dihloretāns, tetrahloretāns, dietilēteris, t-butilmetilēteris, izopropilēteris un to ekvivalents.
  8. 8. Paņēmiens saskaņā ar jebkuru no 1 līdz 5 punktiem, kur minētā bāze ir izvēlēta no rindas: nātrija karbonāts, nātrija bikarbonāts, nātrija acetāts, kālija karbonāts, kālija bikarbonāts, trietilamīns, cēzija karbonāts, litija karbonāts un to ekvivalents.
LVP-99-19A 1992-08-13 1999-02-08 Jauns paņēmiens 7-(aizvietota)-9-[(aizvietota glicil)amido]-6-dimetil-6-deoksitetraciklīnu ražošanai LV12273B (lv)

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US07/928,588 US5284963A (en) 1992-08-13 1992-08-13 Method of producing 7-(substituted)-9-[(substituted glycyl)-amidol]-6-demethyl-6-deoxytetra-cyclines

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LV12273B true LV12273B (lv) 1999-11-20

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