FI116219B - Aromatiska aminoetrar som smärtstillande medel - Google Patents

Aromatiska aminoetrar som smärtstillande medel Download PDF

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Publication number
FI116219B
FI116219B FI970261A FI970261A FI116219B FI 116219 B FI116219 B FI 116219B FI 970261 A FI970261 A FI 970261A FI 970261 A FI970261 A FI 970261A FI 116219 B FI116219 B FI 116219B
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Finland
Prior art keywords
benzyloxy
ethylamino
bromobenzyl
alkyl
pyridine
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FI970261A
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English (en)
Finnish (fi)
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FI970261A0 (sv
FI970261A (sv
Inventor
Howard Tucker
John Oldfield
Peter Warner
Gloria Anne Breault
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Astrazeneca Ab
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Priority claimed from GB9414924A external-priority patent/GB9414924D0/en
Priority claimed from GBGB9501288.6A external-priority patent/GB9501288D0/en
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of FI970261A0 publication Critical patent/FI970261A0/sv
Publication of FI970261A publication Critical patent/FI970261A/sv
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07C237/30—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 non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C237/32—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 non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
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    • C07C255/59—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 the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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Claims (15)

1. Förening med formeln (I) r r , ^CH—N—B—R XOCH—D R4 5 m vari A är fenyl, naftyl, pyrazinyl, tienyl, tiadiazolyl med minst tvä närliggande ringkolatomer, förutsatt att -CH (R3) N (R2) B-R1- och -OCH (R4)-D-bindningsgrupper är beläg-10 na i 1,2-ställning relativt varandra i ringkolatomerna och en ringatom, som är i orto-ställning relativt -OCHR4-bindningsgruppen (och sälunda i 3-ställning relativt -CHR3NR2-bindningsgruppen), inte är substituerad, varvid A antingen är icke-substituerad eller sub-15 stituerad med halogen, trifluormetyl, nitro, amino, cyan, Ci-6-alkoxi, S (0)pCi-6-alkyl, väri p är 0, 1 eller 2, Ci_6- alkyl, fenylsulfonylmetyl eller bensensulfonamido; , B är fenyl, pyridyl, tiazolyl, oxazolyl, tienyl, .·. : tiadiazolyl, imidazolyl, pyrazinyl, pyridazinyl eller py- * · 4 20 ridon, varvid B antingen är icke-substituerad eller sub- • · stituerad med amino, halogen, nitro, hydroxi, Ci-6-alkoxi • · *it>” eller Ci-6-alkyl; • · « ’·’ * D är pyridyl, tienyl, furyl, tiazolyl eller fenyl, varvid D antingen är icke-substituerad eller substituerad :,· j 25 med halogen, cyan, Ci_6-alkyl, Ci-6-alkoxi, trif luormetyl • · · ' i eller trifluormetoxi; och :*! R1 är belägen i ringen B i 1,3- eller 1,4-för- • · * |...f hällande relativt -CH (R3) N (R2)-bindningsgruppen i 6-ledade ‘I’ ringar och i 1,3-förhällande relativt -CH (R3) N (R2)-bind- ·.·.· 30 ningsgruppen i 5-ledade ringar och är karboxi, karboxi- 132 116219 Ci-3-alkyl, 3-oxo-l,2-dihydro-3H-pyrazolyl, tetrazolyl el-ler tetrazolyl-Ci-3-alkyl eller R1 är -CONRaRal, väri Ra är väte eller Ci-6~alkyl och Ral är Ci-io-alkyl, som eventuellt är substituerad med hyd-5 roxi, Ci-4-alkoxi, karboxi, cyan, Ci_4-alkoxikarbonyl eller tetrazolyl, C2-io~alkenyl, 5- eller 6-ledad heteroaryl-Ci-6-alkyl eller 5- eller 6-ledad heterocyklyl; eller Ra och Ral bildar tillsammans med amidkväve, till vilket de är bundna (NRaRal) , en aminosyrarest 10 -NH-CH (Rc)-COORd, väri Rc är Ci_6-alkyl, som eventuellt är substituerade med hydroxi, och Rd är väte eller Ci-6-alkyl, eller R1 är -C0NHS02Rb, väri Rb är Ci_i0-alkyl, som eventuellt är substituerad med hydroxi eller Ci-6-alkoxi, fenyl, 15 som eventuellt är substituerad med halogen, fenyl-Ci-6-alkyl, 5- eller 6-ledad heteroaryl, som eventuellt är substituerad med Ci-4-alkanoylamino, Ci_4-alkyl, halogen eller pyridyl, eller 5- eller 6-ledad mättad heterocyklyl, eller R1 är -CONRaN (Rc) Rd, väri Ra och Rc vardera är väte och 20 Rd är 5- eller 6-ledad heteroaryl, R2 är väte, Ci-6-alkyl, som eventuellt är substitu-;·*· erad med trifluormetyl, C2-6~alkenyl, C2_6-alkynyl, Ci_4-al- . .·. kanoyl C3_6-cykloalkyl-Ci_3-alkyl, fenyl-Ci_3-alkyl eller 5- ,·. : eller 6-ledad heteroaryl-Ci-3-alkyl; * · «
25 R3 är väte eller Ci_4-alkyl; R4 är väte; » · och -NR2: s N-oxider sävida kemiskt möjliga; • · · *·’ ' och dess farmaceutiskt godtagbara salt eller ester eller amid som skall hydrolyseras in vivo. • · :.: : 30 2. Förening enligt patentkrav 1, väri A är eventu- * * t :,t>’ elit substituerad fenyl, naftyl, tiadiazolyl eller tienyl.
3. Förening enligt patentkrav 1, väri B är eventu-elit substituerad pyridyl, fenyl, tiazolyl, tienyl, pyrida-zinyl, tiadiazolyl, imidazolyl, pyrazinyl, pyrimidyl eller ·,·,* 35 oxazolyl. 133 116219
4. Förening enligt patentkrav 1, väri R3 är väte eller metyl och R4 är väte.
5. Förening enligt patentkrav 1, väri D är tienyl, furyl eller fenyl. 5 6. Förening enligt patentkrav 1, väri R2 är väte, etyl, allyl eller 2-propynyl.
7. Förening enligt patentkrav 1, väri R1 är kar-boxi, tetrazolyl eller enligt formel -CONRaRal eller -C0NHS02Rb, väri Ra har definierats i patentkrav 1, Ral är 10 eventuellt substituerad Ci_6-alkyl, C2_6-alkenyl, pyridyl-Ci-4-alkyl, furyl-Ci_4-alkyl eller tetrazolyl-Ci_4-alkyl, och Rb är Ci-4-alkyl (eventuellt substituerad med hydroxi, Ci_4-alkanoylamino, halogen eller Ci_4-alkoxi) eller eventuellt substituerad fenyl-Ci-3-alkyl, fenyl, tienyl, tiadiazolyl, 15 isoxazolyl, pyrazolyl eller 1,1-dioxidotetrahydrotienyl.
8. Förening enligt patentkrav 1, med formeln (IV) R2 Λ I R?^XH2—N—B—R1 I^RS)" "= (IV) 4 * 12 *5 väri R och R har definierats i patentkrav 1, R är halo-*: gen, cyan, Ci-6-alkyl eller Ci_6-alkoxi, n är 0 eller 1, R6 20 är halogen, nitro, trifluormetyl, cyan, amino, Ci_6-alkoxi, ) S (0)pCi-6-alkyl eller bensensulfonamido, och B är fenyl, ti- enyl, pyridazinyl, pyridyl eller tiazolyl.
9. Förening enligt patentkrav 1, som är 6—[N— (2 — : .*. bensyloxi-5-brombensyl) -N-etylamino] pyridazin-3-karboxyl- ,···, 25 syra eller dess farmaceutiskt godtagbara sait eller ester som skall hydrolyseras in vivo. • * • · : ·· 10. Förening enligt patentkrav 1, som är: • · · 2- [N- (2-bensyloxi-5-brombensyl) -N-metylamino] pyri-,V. din-5-karboxylsyra; .·. ; 30 2-[N- (2-bensyloxi-5-brombensyl) -N-etylamino] pyri- din-5-karboxylsyra/ 134 116219 N-(3-pyridylmetyl)-2-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]pyridin-5-karboxiamid; 2-[N- (2-bensyloxi-5-brombensyl)-N-prop-2-yn-l-yl)-amino]pyridin-5-karboxylsyra; 5 2-[N-(2-bensyloxi-5-brombensyl)-N-allylamino]pyri- din-5-karboxylsyra; 2-[N-(2-bensyloxi-5-klorbensyl)-N-etylamino]pyri-din-5-karboxylsyra; 2-[N-(2-bensyloxi-5-metyltiobensyl)-N-etylamino]py-10 ridin-5-karboxylsyra; 2-[N-(2-(4-metylfenylmetoxi)-5-brombensyl)-N-etylamino] pyridin-5-karboxylsyra; 2-[N-(2-(3-klorfenylmetoxi)-5-brombensyl)-N-etylamino] pyridin-5-karboxylsyra; 15 2-[N-(2-(4-klorfenylmetoxi)-5-brombensyl)-N-etyl- amino]pyridin-5-karboxylsyra; 2-[N-(2-tienylmetoxi-5-brombensyl)-N-etylamino]py- ridin-5-karboxylsyra; 6-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]-2-20 etoxipyridin-5-karboxylsyra; 2-[N-(2-(4-brombensyloxi)-5-brombensyl)-N-etylami-no] pyridin-5-karboxylsyra; 6-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]pyri-dazin-3-karboxylsyra; * * · 25 4-[N-(2-bensyloxi-5-nitrobensyl)-N-etylamino]ben- • · • · ,;* soesyra; • N-bensensulfonyl-5-[N-(2-bensyloxi-5-brombensyl)-N- '·’ ’ etylamino] tiofen-2-karboxiamid; N-propyl-2-[N-(2-bensyloxi-5-brombensyl)-N-etylami-:.· f 30 no] tiadiazol-5-karboxiamid; : 5-[4-(N-(2-bensyloxi-5-brombensyl)-N-etylamino)fe- ;·’ nyl] tetrazol; • · · N-bensensulfonyl-2- [N- (2-bensyloxi-5-brombensyl] -N- * · • » etylamino] tiadiazol-5-karboxiamid;
35 N-(3-pyridylmetyl)-2-[N-(2-bensyloxi-5-brombensyl]- N-etylamino]tiadiazol-5-karboxiamid; 135 116219 N-propyl-6-[N-(2-bensyloxi-5-brombensyl)-N-etylami-no]pyridazin-3-karboxiamid; 4-[N-(2-bensyloxi-4-brombensyl)-N-etylamino]bensoe- syra; 5 4-[N-(2-bensyloxi-5-brombensyl]-N-etylamino]bensoe- syra; N-(bensensulfonyl)-2-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]pyridin-5-karboxiamid; N-(propansulfonyl)-2-[N-(2-bensyloxi-5-brombensyl)-
10 N-etylamino] pyridin-5-karboxiarrtid; N-(2-hydroxietansulfonyl)-2-[N-(2-bensyloxi-5-brom-bensyl)-N-etylamino]pyridin-5-karboxiamid; N-(bensensulfonyl)-6-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]pyridazin-3-karboxiamid;
15 N-(bensylsulfonyl)-2-[N-(2-bensyloxi-5-metansulfo- nylbensyl)-N-etylamino]pyridin-5-karboxiamid; N-(5-metylkarbamoyl-l,3,4-tiadiazol-2-sulfonyl)-2-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]pyridin-5-kar-boxiamid;
20 N-(3,5-dimetyl-isoxazol-4-sulfonyl)-6-[N-(2-bensyl- oxi-5-brombensyl)-N-etylamino]pyridazin-3-karboxiamid; ,.: N- (bensensulfonyl) -4- [N- (2-bensyloxi-5-metansulfo- nylbensyl)-N-etylamino]bensenkarboxiamid; Γ'. N-(3-hydroxi-l-karboxiprop-2-yl)-2-[N-(2-bensyloxi- * · · 25 5-brombensyl)-N-etylamino] pyridin-5-karboxiamid; _;··* N- (l-karboxipent-2-yl) -2- [N- (2-bensyloxi-5-bromben- ; ** syl)-N-etylamino]pyridin-5-karboxiamid; V * N-bensyl-2-[N-(2-bensyloxi-5-brombensyl)-N-etylami- no]pyridin-5-karboxiamid; • · ·,· · 30 N-(tetrazol-5-ylmetyl)-2-[N-(2-bensyloxi-5-bromben- : : syl)-N-etylamino]pyridin-5-karboxiamid; 2-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]oxazol-4-karboxylsyra; » · ;* 4- [N- (2-bensyloxi-4-metylbensyl) -N-etylamino]ben- 35 soesyra; • I 136 116219 N-(2-hydroxietyl)-2-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]tiazol-4-karboxiamid; N-(2(S)-hydroxiprop-l-yl)-2-[N-(2-bensyloxi-5-brom-bensyl)-N-etylamino]tiazol-5-karboxiamid;
5 N-(2-hydroxietyl)-2-[N-(2-bensyloxi-5-brombensyl)- N-etylamino]tiazol-5-karboxiamid; 5-[3-(N-(2-bensyloxi-5-brombensyl)-N-etylamino)fe-nyl]tetrazol; 2-[N-(2-bensyloxibensyl)-N-etylamino]pyridin-5-kar- 10 boxylsyra; N-(bensensulfonyl)-4-[N-(3-bensyloxi-2-tienylme-tyl)-N-etylamino]bensenkarboxiamid; N-propyl-4-[N-(3-bensyloxi-2-tienylmetyl)-N-etylamino] bensenkarboxiamid; 15 4-[N-(2-bensyloxi-5-brombensyl)-N-etylamino]-3- etoxibensoesyra; 4-[N-(2-bensyloxi-2-tienylmetyl)-N-etylamino]ben- soesyra; 4- (N-(2-bensyloxi-5-brombensyl)-N-metylamino]ben- 20 soesyra; N-(3-pyridylmetyl)-4-[N-(2-bensyloxibensyl)-N-etyl-amino] bensenkarboxiamid; * · 5- [6-(N-(2-bensyloxi-5-brombensyl)-N-etylamino)-3-pyridazin] tetrazol; 25 5-(N-(2-bensyloxi-5-brombensyl)-N-etylamino] pyra- » · >;*** zin-2-karboxylsyra; eller • " N-(3,5-dimetyl-isoxazol-4-ylsulfonyl)-2-[N-(2-ben- • » · V ' syloxi-5-brombensyl)-N-etylamino]pyridin-5-karboxiamid; eller deras farmaceutiskt godtagbara salter eller estrar ·,· ] 30 eller amider som hydrolyseras in vivo.
11. Farmaceutisk komposition, kännetecknad av att den omfattar en förening enligt nägot av patentkraven » I · *,,, 1-10 och en farmaceutisk godtagbar bärare. > * · I I ·
1. I
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