FI88918B - Foerfarande foer framstaellning av terapeutiskt aktiva benshydryloxietylpiperazinderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva benshydryloxietylpiperazinderivat Download PDF

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FI88918B
FI88918B FI873021A FI873021A FI88918B FI 88918 B FI88918 B FI 88918B FI 873021 A FI873021 A FI 873021A FI 873021 A FI873021 A FI 873021A FI 88918 B FI88918 B FI 88918B
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group
dihydro
formula
compounds
theophylline
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FI873021A
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FI88918C (sv
FI873021A0 (fi
FI873021L (fi
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Andre Buzas
Roland Ollivier
Jean Yves Merour
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Meram Lab
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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    • C07D221/04—Ortho- or peri-condensed ring systems
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
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    • 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
    • C07D295/12—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 singly or doubly bound nitrogen atoms
    • C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
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    • C07D473/00—Heterocyclic compounds containing purine ring systems
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    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
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    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine

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Claims (16)

1. Förfarande för framstälining av terapeutiskt aktiva benshydryloxietylpiperazinderivat som svarar 5 mot den följande allmänna formel II: ;::€X ^ A
10 GH-O-CH -CH -N N —(CH0) -N 11 15 där: R1 , R2 , R3 och R4 , oberöende av varandra, representerar en väteatom, en halogenatom, en lägre alkylgrupp, en lägre alkoxigrupp eller trifluormetylgruppen; n är ett heltal mellan talen 1-6 inkl. dessa;
2. R2 , Rj och R4 = H, n = 2 och NR5R6 = teofyllingrupp (föreningen 40). 30
2. Förfarande enligt patentkravet 1, kännetecknat därav, att R., , Rz, R3 och R4 = H, n = 2 eller 4 och Rs och R6 bildar med kväveatomen en teofyllingrupp (föreningarna 33 och 34). 15
2. R2 ---CH-O-(CH-) _-N N -H IV där R1 , R2, Rj och R^ är säsom definierats 25 ovan, varvid reaktionen sker i ett lämpligt lösningsmedel säsom toluen, xylen eller metyletylketon, och när (b) NR5R6 representerar ftalimidinylgruppen, 30 vid förfarandet en förening med formel V: : ö v·J 3ö 88 918 som erhällits med hjälp av förfarandet enligt punkt (a) , reduceras i närvaro av zink och vid äterflödning, och när 5 (c) NR^ är 3-hydroxiftalimidinyl-gruppen, vid förfarandet en förening med formel V, säsom definierats i punkt (b), bringas att reagera med natriumborhydrid i lämpliga lösningsmedel, som t.ex. metanol, etanol 10 eller isopropanol, och när (d) Rj är väte och R6 är en 3-karboxibensoyl-grupp, en förening med formel V, säsom definierats i punkt (b), bringas att 15 reagera med en vattenlösning av natrium- sulfid vid en temperatur som understiger 5°C, och när (e) Rj representerar en väteatom och R6 en 20 bensoylgrupp, vilken eventuellt är substi- tuerad med en hydroxy- eller nitro-grupp, vid förfarandet en syraklorid med formel VI: / R7 25 / VI C-Cl 11 (I 30 där R7 är väte, en hydroxigrupp eller en nitrogrupp, bringas att reagera med en amin med formel VII: 3 5 // ^ VII c:H0 (CM ,) nN N' (CH ) N H,. L i. \ / 1 n i ""ö R M 39 8 8 9 I 8 där R, , R2, Rj och R4 är säsom definierats tidigare, varvid reaktionen sker i närvaro av pyridin i ett inert lösningsmedel, säsom ett aromatiskt kolväte, t.ex. bensen 5 eller toluen, eller ett klorerat lösnings medel säsom kloroform eller metylenklorid, och att de erhällna derivaten eventuellt omvandlas till deras syraadditionssalter. 10
2. R5 och R6 representerar, den ena en väteatom och den andra en bensoylgrupp som är substituerad med en hydroxi-, karboxi- eller nitrogrupp, eller icke är substituerad; eller Rs och R6 bildar, med den kväveatom tili vilken de är 25 bundna, en substituerad eller icke-substituerad heterocyklisk 5- eller 6-ledad grupp, som är vald ur följande grupper: succinimidyl, 4-fenylsuccinimidyl, ftalimidyl, naftalimidyl, ftalimidiny1, 3-hydroxi-ftalimidinyl, 2-oxobensimidazolinyl, 3-bensyl-2-oxo-30 bensimidazolinyl, 1,2,3,4-tetrahydro-2,4-dioxokinazo- linyl, 3,4-dihydro-4-oxokinazolinyl, 3,4-dihydro-4 - oxo-2-mety Ikinäzoliny 1, 3,7-dihydro-l, 3-dimetyl- 2, 6-dioxo-lH-purinyl, 3,7-dihydro-3,7-dimetyl-2,6-di- oxo-lH-puriny1, kännetecknat därav, att när S 5 (a) NR5R6 representerar en av följande grupper: succinimidyl, 4-fenylsuccinimidyl, ftalimidyl, naftalimidyl, 2-oxobensimidazolinyl, 37 8 8 9 1 8 3 -bensy 1-2 -oxobensimidazolinyl, 3,4-di- hydro-4-oxo-kinazolinyl, 3,4-dihydro- 2-mety1-4-oxokinazolinyl, 3,7-dihydro- 1,3-dimetyl-2,6-dioxo-lH-purinyl, 3,7-di-5 hydro-3,7-dimetyl-2, 6-dioxo-lH-purinyl eller 1,2,3,4-tetrahydro-2,4-dioxokinazo-linyl, vid förfarandet ett derivat med formel III: Λ
10 X-(CHj -N HI 2 n . R6 där n, R5 och R6 är säsom definierats ovan och X är en halogen- eller tosylgrupp, 15 bringas att reagera under äterflödning med ett överskott av benshydryloxiety1-piperazin med formel IV:
3. Förfarande enligt patentkravet 1, kännetecknat därav, att Rt
= 4-F, R2 , R3 och R4 = H, 20 n = 2 eller 4 och NR5R6 = teofyllingrupp (föreningarna 35 och 42). 25 4. Förfarande enligt patentkravet 1, kännetecknat därav, att R1 = 4-CH3 , R2 , Rj och R4 = H, n = 2 eller 4 och 30 NR5R6 = teofyllingrupp (föreningarna 36 och 41).
5. Förfarande enligt patentkravet 1, kännetecknat 35 därav, att R, = 4-Cl, R2 , R3 och R4 = H, n = 2 eller 4 och NR5R6 = teofyllingrupp 40 88 91 8 (föreningarna 37 och 43).
6. Förfarande enligt patentkravet 1, kännetecknat 5 därav, att R, och R3 = 4-CL, R2 och R4 = H, n = 2 eller 4 och NR5R6 = teofyllingrupp 10 (föreningarna 38 och 45).
7. Förfarande enligt patentkravet 1, kännetecknat därav, att
15 R1 = 4-CHjO, R2 , R3 och R4 = H, n = 2 eller 4 och nr5r6 = teofyllingrupp ro (föreningarna 39 och 46).
8. Förfarande enligt patentkravet 1, kännetecknat därav, att R, = 2 -Cl,
9. Förfarande enligt patentkravet 1, kännetecknat därav, att R1 och Rj = 4-F, R2 och R4 = H, 35 n = 2 och NR5R6 = teofyllingrupp (föreningen 44).
FI873021A 1986-07-10 1987-07-08 Förfarande för framställning av terapeutiskt aktiva benshydryloxietylp iperazinderivat FI88918C (sv)

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Application Number Priority Date Filing Date Title
FR8610114 1986-07-10
FR8610114A FR2601366B1 (fr) 1986-07-10 1986-07-10 Derives de la benzhydryloxyethyl-piperazine, procedes d'obtention et de compositions pharmaceutiques les contenant.

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FI873021A0 FI873021A0 (fi) 1987-07-08
FI873021L FI873021L (fi) 1988-01-11
FI88918B true FI88918B (fi) 1993-04-15
FI88918C FI88918C (sv) 1993-07-26

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EP (1) EP0254627B1 (sv)
JP (1) JPS6323873A (sv)
CN (1) CN87104734A (sv)
AT (1) ATE77376T1 (sv)
AU (1) AU604718B2 (sv)
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DE (1) DE3779825T2 (sv)
DK (1) DK355687A (sv)
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FI (1) FI88918C (sv)
FR (1) FR2601366B1 (sv)
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MA (1) MA21030A1 (sv)
NO (1) NO171637C (sv)
OA (1) OA08635A (sv)
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US5276035A (en) * 1990-07-26 1994-01-04 Novo Nordisk A/S 1,4-disubstituted piperazines
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DK178590D0 (da) * 1990-07-26 1990-07-26 Novo Nordisk As 1,4-disubstituerede piperaziner
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EP0539164A1 (en) * 1991-10-23 1993-04-28 Sankyo Company Limited Nitrogen-containing tetracyclic compounds having anti-allergic and anti-asthmatic activities, their preparation and use
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AU6003099A (en) 1998-10-06 2000-04-26 Takeda Chemical Industries Ltd. Fused pyridazine compounds, process for the preparation of the same and uses thereof
CN1329614A (zh) 1998-10-21 2002-01-02 武田药品工业株式会社 稠合的哒嗪衍生物、它们的制备方法和用途
US6946475B1 (en) 1999-04-07 2005-09-20 University Of Virginia Patent Foundation Anticancer calcium channel blockers
ATE269848T1 (de) * 1999-04-07 2004-07-15 Univ Virginia Calciumkanalblocker als antikrebsmittel
RU2202690C2 (ru) * 1999-11-22 2003-04-20 Общество с ограниченной ответственностью "Надымгазпром" Способ разработки газового месторождения
MX360640B (es) 2010-03-01 2018-11-09 Tau Therapeutics Llc Star Diagnosis e imagenologia de cancer.
PL235807B1 (pl) * 2018-04-11 2020-10-19 Politechnika Rzeszowska Im Ignacego Lukasiewicza Sposób nanoszenia okładziny ciernej, zwłaszcza na blachę klocka hamulcowego

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ATE77376T1 (de) 1992-07-15
FI88918C (sv) 1993-07-26
NO171637C (no) 1993-04-14
FR2601366B1 (fr) 1988-11-25
CA1306461C (en) 1992-08-18
ES2042593T3 (es) 1993-12-16
EP0254627B1 (fr) 1992-06-17
JPS6323873A (ja) 1988-02-01
DE3779825D1 (de) 1992-07-23
FI873021A0 (fi) 1987-07-08
NO171637B (no) 1993-01-04
ZA874971B (en) 1988-03-30
NO872821L (no) 1988-01-11
CN87104734A (zh) 1988-04-06
AU604718B2 (en) 1991-01-03
US4908365A (en) 1990-03-13
TNSN87087A1 (fr) 1990-01-01
DK355687D0 (da) 1987-07-09
NO872821D0 (no) 1987-07-07
GR3005341T3 (sv) 1993-05-24
DE3779825T2 (de) 1992-12-24
MA21030A1 (fr) 1988-04-01
FI873021L (fi) 1988-01-11
FR2601366A1 (fr) 1988-01-15
RU2032680C1 (ru) 1995-04-10
OA08635A (fr) 1988-11-30
EP0254627A1 (fr) 1988-01-27
DK355687A (da) 1988-01-11
AU7539687A (en) 1988-01-21

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