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FI80440B - Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara afidkolanderivat. - Google Patents

Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara afidkolanderivat. Download PDF

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Publication number
FI80440B
FI80440B FI832622A FI832622A FI80440B FI 80440 B FI80440 B FI 80440B FI 832622 A FI832622 A FI 832622A FI 832622 A FI832622 A FI 832622A FI 80440 B FI80440 B FI 80440B
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FI832622A
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FI80440C (sv
FI832622A (fi
FI832622A0 (fi
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Arnold Harry Ratcliffe
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Ici Plc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/86—Ring systems containing bridged rings containing four rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (3)

1. Analogiförfarande för framställning av terapeu-tiskt användbara afidikolanderivat med formeln (II) 5 io CH3'*JT J* (II) R* ‘*3 CH, R 15 väri R2 betecknar en hydroxigrupp; R3 betecknar en hydroximetylgrupp eller en grupp med formeln -CH2 0-C0-0R6, väri R6 betecknar en fenylalkylgrupp med högst 9 kolatomer; 20 eller R2 och R3 är förenade för bildande av en grupp med formeln -0-C0-0CH2-; R4 betecknar en hydroxigrupp; R5 betecknar en formylgrupp, en grupp med formeln -CHR7OH, väri R7 betecknar en alkylgrupp med högst 3 kolatomer, 25 eller R5 betecknar en grupp med formeln -CH2 0-C0-0R8 , väri R8 betecknar en fenylgrupp eller en fenylalkylgrupp med högst 9 kolatomer, eller R8 betecknar en piperidinylgrupp eller en N-substituerad piperidinylgrupp med formeln (lii) 30 -CO-COR6 (III) il väri R6 betecknar samma som ovan, eller R5 betecknar en grupp med formeln (IV) 33 80440 /R9
5 -CH20-C0-(CH2 )n -N<^ (IV) ^-R10 väri m är ett helt tai 1-4, R9 betecknar väte, och R10 betecknar väte eller R9 och R10 betecknar tillsanunans med 10 den närliggande kväveatomen en morfolinogrupp, eller R5 betecknar en grupp med formeln -CH2 0-S02-R13 , väri R13 betecknar en karboxifenylgrupp eller en naftylgrupp, vilken eventuellt kan vara substituerad med en dialkylaminogrupp med högst 6 kolatomer; eller R4 och R5 är förenade för 15 bildande av gruppen -0-CH2- eller -0-C0-0CH2-; eller dä lämpligt, farmaceutiskt godtagbara salter därav, kännetecknat därav, att man a) ifall R5 betecknar en formylgrupp, oxiderar en motsvarande förening, väri R5 betecknar en hydroximetyl- 20 grupp; b) ifall R5 betecknar en grupp med formeln -CHR7OH, väri R7 betecknar en alkylgrupp med högst 3 kolatomer, omsätter en motsvarande förening, väri R5 betecknar en formylgrup, med ett litiumderivat med formeln R7Li, väri
25 R7 har ovan angivna betydelse, och omsätter den litiumhal-tiga mellanprodukten med vatten; c) ifall R5 betecknar en grupp med formeln -CH20-S02-R13, väri R13 betecknar samma som i formeln (II), omsätter en motsvarande förening, väri R5 betecknar 30 en hydroximetylgrupp, med en förening med formeln R13-S02-Z, väri R13 betecknar samma som ovan och Z betecknar en halogenatom; d) ifall R4 och R5 är förenade för bildande av gruppen -0-CH2-, omsätter en motsvarande förening, väri R5 35 betecknar en alkansulfonyloximetylgrupp med högst 4 koi- 34 80 440 atomer, eller en bensensulfonyloximetyl- eller toluensul-fonyloximetylgrupp, med en alkalisk substans; e) ifall ätminstone nägondera av R3 och R5 beteck-nar en grupp med formeln -CH2 O-CO-OR6, väri R6 betecknar 5 en fenylalkylgrupp med högst 9 koi atomer, omsätter en mot-svarande förening, väri ätminstone nägondera av R3 och R5 betecknar en hydroximetylgrupp, med en förening med formeln R60-C0-Z, väri R6 har den omedelbart ovan angivna betydelsen och Z betecknar en halogenatom; 10 f) ifall R5 betecknar en fenoxikarbonyloximetyl- grupp eller R4 och R5 är förenade för bildande av en grupp med formeln -0-C0-0CH2-, omsätter en motsvarande förening, väri R4 betecknar en hydroxigrupp och R5 betecknar en hydroximetylgrupp, med en förening med formeln C6H50-C0-Z, 15 väri Z har ovan angivna betydelse; g) ifall R5 betecknar en grupp med formeln (VIII) -ch2o-co-o—C (VIII) 20 I 6 CO-OR väri R6 betecknar en fenylalkylgrupp med högst 9 kolato-25 mer, omsätter en motsvarande förening, väri R5 betecknar en hydroximetylgrupp, med en förening med formeln (IX) Z-CO-oH" 30 (IX> CO-OR6 väri R6 har den omedelbart ovan angivna betydelsen och Z 35 betecknar en halogenatom; il 35 80440 h) if all R5 betecknar en piperidinyloxikarbonyl oxime tylgrupp, hydrogenolyserar en motsvarande förening, väri R5 betecknar en grupp med formeln (VIII), väri R6 har ovan angivna betydelse; 5 i) ifall R5 betecknar en grupp med formeln (IV) R9 -CH2 O-CO- ( ch2 )b -N ( IV) ^""R10 10 omsätter en motsvarande förening, väri R5 betecknar en hydroximetylgrupp, med en syra med formeln R9R10N(CH2 )b-C02H eller med en syrahalogenid eller -anhyd-rid därav, i vilken formeln m, R9 och R10 betecknar samma 15 som i formeln (IV); j) ifall R2 och R3 , och R4 och R5 är förenade för bildande av gruppen med formeln -0-C0-0CH2-, omsätter afi-dikolin med fosgen; eller k) ifall R5 betecknar en grupp med formeln
20 -CH2 O-CO-(CH2 )b -NH2 , hydrogenolyserar en motsvarande före ning, väri R5 betecknar en grupp med formeln -CH20-C0-(CH2 )a-NH-C02R15, väri m betecknar samma som i formeln (IV) och R15 betecknar en a-fenylalkylgrupp med högst 9 kolatomer; 25 och eventuellt överför den erhällna föreningen till ett farmaceutiskt godtagbart salt därav.
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer ett farmaceutiskt godtagbart salt av en förening med formeln (II), 30 väri R2 och R4 b£da betecknar en hydroxigrupp, R3 betecknar en hydroximetylgrupp och R5 betecknar en glycyloxime-tyl-, piperidin-4-yloxikarbonyloximetyl-, γ -(N-morfoli-no)-n-butyryloximetyl-, m-karboxibensensulfonyloximetyl-eller 5-dimetylaminonaftalensulfonyloximetylgrupp. 35
3. Förfarande enligt patentkravet 1, känne- 36 80 4 40 t e c k n a t därav, att man framställer ett farmaceu-tiskt godtagbart sait av en förenlng med formeln (II), väri R2 och R4 bäda betecknar en hydroxigrupp, R3 beteck-nar en hydroximetylgrupp och R5 betecknar en glycyloximetyl. Il
FI832622A 1982-11-10 1983-07-19 Analogiförfarande för framställning av terapeutiskt användbara afidiko landerivat FI80440C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8232084 1982-11-10
GB8232084 1982-11-10

Publications (4)

Publication Number Publication Date
FI832622A0 FI832622A0 (fi) 1983-07-19
FI832622A FI832622A (fi) 1984-05-11
FI80440B true FI80440B (fi) 1990-02-28
FI80440C FI80440C (sv) 1990-06-11

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FI832622A FI80440C (sv) 1982-11-10 1983-07-19 Analogiförfarande för framställning av terapeutiskt användbara afidiko landerivat

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US (2) US4803201A (sv)
EP (1) EP0112603B2 (sv)
JP (1) JPS5988438A (sv)
AT (1) ATE25661T1 (sv)
AU (1) AU572787B2 (sv)
CA (1) CA1243025A (sv)
DE (1) DE3369965D1 (sv)
DK (1) DK332283A (sv)
ES (2) ES8604105A1 (sv)
FI (1) FI80440C (sv)
GR (1) GR78865B (sv)
HU (1) HU196159B (sv)
IE (1) IE55772B1 (sv)
IL (1) IL69319A (sv)
NO (1) NO157136C (sv)
NZ (1) NZ204933A (sv)
PT (1) PT77086B (sv)
ZA (1) ZA835252B (sv)

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Publication number Priority date Publication date Assignee Title
US5387520A (en) * 1992-08-27 1995-02-07 Worcester Foundation For Experimental Biology Treatment of tumor cells in vitro with neurotrophic factors and cell proliferation inhibitors
US7396534B2 (en) * 2004-05-11 2008-07-08 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Cosmetic compositions containing Nigrospora sphaerica extracts
CN108947790B (zh) * 2017-12-01 2021-07-06 厦门恩成制药有限公司 二萜类化合物及其在制备抗肿瘤药物中的应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1331520A (en) * 1971-01-27 1973-09-26 Ici Ltd Aphidicolin and derivatives thereof
US3761512A (en) * 1972-02-28 1973-09-25 Ici Ltd Anti-viral compounds
FR2500440A1 (fr) * 1981-02-23 1982-08-27 Roussel Uclaf Nouveaux medicaments derives de la 3-hydroxy dodecahydro benz (e) inden-7-one disubstituee en position 6, produits derives de la 3-hydroxy dodecahydro benz (e) inden-7-one disubstituee en position 6, et leur procede de preparation ainsi que des produits intermediaires
JPS62155232A (ja) * 1985-12-27 1987-07-10 Rikagaku Kenkyusho アフイデイコリン誘導体及びその合成法並びに制癌剤

Also Published As

Publication number Publication date
NZ204933A (en) 1986-12-05
NO157136C (no) 1988-01-27
FI80440C (sv) 1990-06-11
FI832622A (fi) 1984-05-11
EP0112603B1 (en) 1987-03-04
US5039710A (en) 1991-08-13
JPH0480890B2 (sv) 1992-12-21
EP0112603B2 (en) 1992-03-18
FI832622A0 (fi) 1983-07-19
NO157136B (no) 1987-10-19
NO832574L (no) 1984-05-11
ZA835252B (en) 1984-06-27
IE831676L (en) 1984-05-10
CA1243025A (en) 1988-10-11
ES8506756A1 (es) 1985-08-01
US4803201A (en) 1989-02-07
PT77086B (en) 1986-01-24
AU572787B2 (en) 1988-05-19
ES531941A0 (es) 1985-08-01
PT77086A (en) 1983-08-01
IL69319A (en) 1987-01-30
AU1720183A (en) 1984-05-17
DK332283A (da) 1984-05-11
EP0112603A1 (en) 1984-07-04
ATE25661T1 (de) 1987-03-15
IE55772B1 (en) 1991-01-16
JPS5988438A (ja) 1984-05-22
ES525299A0 (es) 1986-01-16
DK332283D0 (da) 1983-07-19
DE3369965D1 (en) 1987-04-09
ES8604105A1 (es) 1986-01-16
HU196159B (en) 1988-10-28
GR78865B (sv) 1984-10-02

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