PL182857B1 - Nowe pochodne tetraliny, sposób wytwarzania nowych pochodnych tetraliny oraz kompozycja farmaceutyczna - Google Patents

Nowe pochodne tetraliny, sposób wytwarzania nowych pochodnych tetraliny oraz kompozycja farmaceutyczna

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PL182857B1
PL182857B1 PL96323037A PL32303796A PL182857B1 PL 182857 B1 PL182857 B1 PL 182857B1 PL 96323037 A PL96323037 A PL 96323037A PL 32303796 A PL32303796 A PL 32303796A PL 182857 B1 PL182857 B1 PL 182857B1
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ome
alkyl
hydrogen
alkoxy
hydroxy
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Robert Swoboda
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Novartis Ag
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    • 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
    • C07D295/06—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 halogen atoms or nitro radicals
    • C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • A—HUMAN NECESSITIES
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    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
    • C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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    • 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
    • C07C237/48—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 six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
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    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • 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
    • C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/033—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Abstract

I. Nowe pochodne tetraliny o wzorze 1 , w którym R 1 i R 2 niezaleznie, oznaczaja wodór (C1-4)alkil, (C1-4)alkoksyl, chlorowiec, trifiuorometyl, R3 oznacza wodór, hydroksyl, (C1-4)alkoksyl, cyjano, karbamoil, zas R4 i R5 niezaleznie, oznaczaja wodór, (C1 4)alkil, hydro- ksy(C2-4)alkil lub tworza razem z atomem azotu do którego sa przylaczone grupe piperydynowa, w postaci wolnej zasady lub soli addycyjnej z kwasem. 5 Sposó b w ytw arzania now ych pochodnych tetraliny o w zorze 1, w którym R 1 i R 2 n iezaleznie, o zn aczaja w o d ó r (C1-4)alkil, ( C 1 -4)alkoksyl, chloro- w iec, tnfiu o ro m ety l, R1 o zn acza w odór, hydroksyl, (C1-4)alkoksyl, cyjano, karb am o il, zas R4 i R5 niezaleznie, oznaczaja w odór, (C1-4)alkil, h y d ro k sy (C 2-4)alk il lu b tw o rz a razem z atom em azotu do którego saprzylaczone grupe piperydynow a, w postaci w olnej zasady lu b soli addycyjnej z kw asem , z n a m ien n y ty ra , ze zw iazek o w zo rze 2, w którym R 3, R 4 i R 5 m a ja w yzej p o d an e zn aczen ie, a Hal o zn acza c h lo ro w iec, poddaje sie reakcji ze zw iazkiem o w zo rze 3, w k tó - rym R 1 i R2 m a j a w y zej podane znaczenie, i w y d ziela sie p ro d u k t w postaci w olnej zasady lu b w postaci soli addycyjnej z kw asem 6 K o m p o zy cja farm aceutyczna, zaw ierajaca su b stan cje a k ty w n a w po laczen iu z n osnikiem lub rozcienczalnikiem farm aceu ty czn y m , zn am ien n a ty m , ze ja k o su b stan cje ak ty w n a zaw iera zw iazek o w zo rze 1, w którym R 1 i R2 niezaleznie, oznaczaja w o d ó r (C 1 -4)alkil, ( C 1 -4)alkoksyl, chloro- wiec, trifiuorom etyl, R 3 ozn acza w odór, h y droksyl, (C1-4)alkoksyl, cy jan o , karb am o il, zas R4 i R5 n iezaleznie, oznaczaja w o d ó r, ( C 1-4)alk il, h y d ro k s yl(C 2- 4)alkil lu b tw o rz a raz e m z atom em azotu do którego sa przylaczone g rupe p iperydy- now a, w postaci w olnej zasady lub soli addycyjnej z farm aceu ty czn ie d o p u sz- czalnym kw asem Wzór 1 Wzór 2 Wzór 3 PL PL PL

Description

I . Nowe pochodne tetraliny o wzorze 1, w którym x R| i R2 niezależnie, oznaczają wodór (C,-4)alkil, (Cr4)alkoksyl, 57) chlorowiec.tnfluorometyl,
R3 oznacza wodór, hydroksyl, (Cpjalkoksyl, cyjano, karbamoil, zaś
Rą i R5 niezależnie, oznaczają wodór, (C^Jalkil, hydroksy(C2-4)alkil lub tworzą razem z atomem azotu do którego są przyłączone grupę piperydynową, w postaci wolnej zasady lub soli addycyjnej z kwasem.
Sposob wytwarzam a nowych pochodnych tetral my o ozorze 1, w którym
Ri i R2 niezależnie, oznaczają wodór (Cr4)alkil, (Cr4)alkoksyl, chlorowiec, tnfluorometyl,
Ri oznacza wodór, hydroksyl, (Cr4)alkoksyl, cyjano, karbamoil, zaś
Ra i R5 niezależnie, oznaczają wodor, (Cr4)aJkil. hydroksy(C2-4)alkil lub tworzą razem z atomem azotu do którego są przyłączone grupę piperydynową, w postaci wolnej zasady lub soli addycyjnej z kwasem, znamienny tym, ze związek o wzorze 2, w którym R3, R41 R5 mają wyżej podane znaczenie, a Hal oznacza chlorowiec, poddaje się reakcji ze związkiem o wzorze 3, w którym R| 1 R2 mają wyżej podane znaczenie, i wydziela się produkt w postaci wolnej zasady lub w postaci soli addycyjnej z kwasem
Kompozycja farmaceutyczna, zawierająca substancję aktywną w połączeniu z nośnikiem lub rozcieńczalnikiem farmaceutycznym, znamienna tym. ze jako substancję aktywną zawiera związek o wzorze 1, w którym
R1 i R2 niezależnie, oznaczają wodór (Cr4)alkil, (Cr4)alkoksyl, chlorowiec, tnfluorometyl,
Ri oznacza wodór, hydroksyl, (Ci-4)alkoksyl, cyjano, karbamoil, zaś
R4 i R5 niezależnie, oznaczają wodór, (C,-4)alkil, hydroksy(C2-4)alkil lub tworzą razem z atomem azotu do którego są przyłączone grupę piperydynową, w postaci wolnej zasady lub soli addycyjnej z farmaceutycznie dopuszczalnym kwasem
Hal
Wzór 1 Wzór 2
Wzór 3
Nowe pochodne tetraliny, sposób wytwarzania nowych pochodnych tetraliny oraz kompozycja farmaceutyczna

Claims (6)

1. Nowe pochodne tetraliny o wzorze 1, w którym
R, i R2 niezależnie, oznaczają wodór (Cr4)alkil, (C]-4)alkoksyl, chlorowiec, trifluorometyl,
R3 oznacza wodór, hydroksyl, (C]-4)alkoksyl, cyjano, karbamoil, zaś
R4 i R5 niezależnie, oznaczają wodór, (C|-4)alkil, hydroksy(C2-4)alkil lub tworząrazem z atomem azotu do którego sąprzyłączone grupę piperydynową, w postaci wolnej zasady lub soli addycyjnej z kwasem.
2. Związek według zastrz. 1, znamienny tym, że
R| i R2 niezależnie, oznaczają wodór, (C]-4)alkil, (C]-4)alkoksyl, chlorowiec, trifluorometyl,
R3 oznacza wodór, hydroksyl, (C,-4)alkoksyl, cyjano, karbamoil, zaś
R4 i R5 niezależnie, oznaczają wodór, (C]-4)alkil, lub tworząrazem z atomem azotu do którego sąprzyłączone grupę piperydynową, w postaci wolnej zasady lub soli addycyjnej z kwasem.
3. Związek według zastrz. 1,znamienny tym, że jest wybrany spośród związków o wzorze 1, w postaci optycznie czynnej lub racemicznej, w którym:
Ri = 4-Cl, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
Ri =H, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
Ri = 2-Cl, R2 = H, R3 = OMe, R4 = Me, R5 = Me,
Ri = 2-Me, R2 = H, R3 = OMe, R4 = Me, R5 = Me,
Ri =2-0Me, R2 = H, R3 = OMe, R4 = Me, R5 = Me,
Ri = H, r2 = h, R3 = OH, R4 = Me, R5 = Me,
Ri = H, R2 = H, r3 = h, R4 = Me, R5 = Me,
Ri = 4-Me, r2 = h, R3 = OMe, R4 = Me, Rs = Me,
Ri = 4-CF3, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
Ri =2-Cl, R2 = 4-CI, R3 = OMe, R4 = Me, R5 = Me,
R, = 2-F, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
R, =3-CI, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
R, =2-Cl, r2 = h, R3 = OMe, R4 = Me, R5 = H,
Ri = H, r2 = h, R3 = OMe, R4 + R5 = piperydyno,
R, = 2-CI, R2 = H, R3 = OMe, R4 + R5 = piperydyno,
Ri = H, R2 = H, R3 = OMe, R4 = n-Pr, R5 = n-Pr,
Ri = 4-CF3, r2 = h, R3 = OH, R4 = Me, R5 = Me,
Ri = 2-Et, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
R, = 2-C1, r2 = h, R3 = CN, R4 = Me, R5 = Me,
Ri =2-CI, R2 = 4-F, R3 = OMe, R4 = Me, R5 = Me,
Ri = 2-F, R2 = 4-F, R3 = OMe, R4 = Me, R5 = Me,
R, = 2-OMe, r, = 4-OMe, R3 = OMe, R4 = Me, R5 = Me,
Ri = 2-F, R2 = 3-F, R3 = OMe, R4 = Me, R5 = Me,
182 857 cd. tabeli
R) = 2-OMe, R2 = 3-OMe, R3 = OMe, R4 = Me, R5 = Me,
Ri = 2-Me, R2 = 5-Me, R3 = OMe, R4 = Me, R5 = Me,
Rj = 2-C1, R2 = 3-C1, R3 = OMe, R4 = Me, R5 = Me,
Ri =2-F, R2 = 5-F, R3 = OMe, R4 = Me, R5 = Me,
Rj = 2-Me, R2 = 4-Me, R3 = OMe, R4 = Me, R5 = Me,
Ri = 2-CI, r2 = h, r3 = CONH,, R4 = Me, R5 = Me,
R, = 4-CF3, r2 = h, R3 = OMe, R4 = Me, r5 = h,
R, = 4-OMe, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
Ri =4-F, r2 = h, R3 = OMe, R4 = Me, R5 = Me,
Ri = 4-CF3, r2 = h, R3 = OMe, R4 = Et-OH, R5 = Me, i
R, =4-CF3, r2 = h, R3 = H, R4 = Me, R5 = Me, przy czym Me oznacza metyl, Et oznacza etyl, a Pr oznacza propyl, w postaci wolnej zasady lub soli addycyjnej z kwasem.
4. Związek według zastrz. 1, znamienny tym, że jest nim (R)-1,2,3,4-tetrahydro-8-metoksy-N,N-dimetylo-5-[4-(trifluorometylo)fenylo]-2-naftyloamina, w postaci wolnej zasady lub soli addycyjnej z kwasem.
5. Sposób wytwarzania nowych pochodnych tetraliny o wzorze 1, w którym
R] i R2 niezależnie, oznaczająwodór (C ] -4)alkil, (C ]-4)alkoksyl, chlorowiec, trifluorometyl, R3 oznacza wodór, hydroksyl, (C]-4)alkoksyl, cyjano, karbamoil, zaś
R4 i R5 niezależnie, oznaczająwodór, (Cr4)alkil, hydroksy(C2-4)alkil lub tworzą razem z atomem azotu do którego są przyłączone grupę piperydynową w postaci wolnej zasady lub soli addycyjnej z kwasem, znamienny tym, że związek o wzorze 2, w którym R3, R4 i R5 mają wyżej podane znaczenie, a Hal oznacza chlorowiec, poddaje się reakcji ze związkiem o wzorze 3, w którym R| i R2 mają wyżej podane znaczenie, i wydziela się produkt w postaci wolnej zasady lub w postaci soli addycyjnej z kwasem.
6. Kompozycja farmaceutyczna, zawierająca substancję aktywną w połączeniu z nośnikiem lub rozcieńczalnikiem farmaceutycznym, znamienna tym, że jako substancję aktywną zawiera związek o wzorze 1, w którym
Ri i R2 niezależnie, oznaczająwodór (C(-4)alkil, (C|-4)alkoksyl, chlorowiec, trifluorometyl,
R3 oznacza wodór, hydroksyl, (C]-4)alkoksyl, cyjano, karbamoil, zaś
R4 i R5 niezależnie, oznaczająwodór, (C|-4)alkil, hydroksy(C2-4)alkil lub tworząrazem z atomem azotu do którego są przyłączone grupę piperydynową w postaci wolnej zasady lub soli addycyjnej z farmaceutycznie dopuszczalnym kwasem.
PL96323037A 1995-05-05 1996-05-03 Nowe pochodne tetraliny, sposób wytwarzania nowych pochodnych tetraliny oraz kompozycja farmaceutyczna PL182857B1 (pl)

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GBGB9509156.7A GB9509156D0 (en) 1995-05-05 1995-05-05 Organic compounds
PCT/EP1996/001841 WO1996034849A1 (en) 1995-05-05 1996-05-03 Tetralines bearing a phenyl substituant on the aromatic ring and their use in the treatment of epilepsy, stroke and brain or spinal trauma

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PL323037A1 PL323037A1 (en) 1998-03-02
PL182857B1 true PL182857B1 (pl) 2002-03-29

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US (1) US6169116B1 (pl)
EP (1) EP0823892B1 (pl)
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EP1458386B1 (en) * 2001-12-27 2007-04-18 Ortho-McNeil Pharmaceutical, Inc. Aroyl pyrrole heteroeryl and methanols useful for treating a central nervous system disorder
AU2003241453A1 (en) 2002-05-17 2003-12-02 Janssen Pharmaceutica N.V. Aminotetralin-derived urea modulators of vanilloid vr1 receptor
WO2005037286A1 (en) 2003-03-25 2005-04-28 Vasopharm Biotech Gmbh Use of pteridine derivatives for the treatment of increased intracranial pressure and secondary ischemia
EP1956006A1 (en) 2007-02-06 2008-08-13 Laboratorios del Dr. Esteve S.A. Heterocyclyl-substituted-tetrahydro-naphthalen derivatives as 5-HT7 receptor ligands
EP1975161A1 (en) * 2007-03-28 2008-10-01 Laboratorios del Dr. Esteve S.A. Heterocyclyl-substituted- tetrahydro-napthalen-amine derivatives, their preparation and use as medicaments
WO2008154044A1 (en) * 2007-06-15 2008-12-18 University Of Florida Research Foundation Therapeutic compounds and methods of use
EP2011786A1 (en) * 2007-07-05 2009-01-07 Laboratorios del Dr. Esteve S.A. Indane-amine derivatives, their preparation and use as medicaments
CN106573872B (zh) * 2014-05-19 2021-07-20 东北大学 5-羟色胺受体靶向化合物和方法
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ZA963540B (en) 1997-11-03
NO975087D0 (no) 1997-11-04
PT823892E (pt) 2000-11-30
HUP9801068A3 (en) 2000-02-28
JP3194965B2 (ja) 2001-08-06
EP0823892A1 (en) 1998-02-18
AU5812996A (en) 1996-11-21
FI973530A (fi) 1997-11-04
TW359667B (en) 1999-06-01
RU2169727C2 (ru) 2001-06-27
NZ308471A (en) 1999-01-28
DE69608891D1 (de) 2000-07-20
SK282022B6 (sk) 2001-10-08
DE69608891T2 (de) 2000-11-16
PL323037A1 (en) 1998-03-02
IL118141A0 (en) 1996-09-12
KR100435009B1 (ko) 2004-08-16
TR199701298T1 (xx) 1998-02-21
WO1996034849A1 (en) 1996-11-07
FI973530A0 (fi) 1997-08-27
CN1183763A (zh) 1998-06-03
AR004484A1 (es) 1998-12-16
HK1014929A1 (en) 1999-10-08
CA2217855A1 (en) 1996-11-07
NO308948B1 (no) 2000-11-20
SK148597A3 (en) 1998-10-07
US6169116B1 (en) 2001-01-02
CN1122019C (zh) 2003-09-24
CZ348697A3 (cs) 1998-02-18
MX9708510A (es) 1998-03-31
PE54797A1 (es) 1998-01-21
BR9608169A (pt) 1999-02-09
KR19990008301A (ko) 1999-01-25
CZ292022B6 (cs) 2003-07-16
ES2148772T3 (es) 2000-10-16
EP0823892B1 (en) 2000-06-14
GB9509156D0 (en) 1995-06-28
DK0823892T3 (da) 2000-10-02
ATE193884T1 (de) 2000-06-15
GR3033715T3 (en) 2000-10-31
HUP9801068A2 (hu) 1999-05-28
JPH10513479A (ja) 1998-12-22
CA2217855C (en) 2008-12-09
IL118141A (en) 2002-11-10
AU706392B2 (en) 1999-06-17
CO4440486A1 (es) 1997-05-07
NO975087L (no) 1997-11-04

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