LV13338B - New substituted azetidinones as anti-inflammatory and antidegenerative agents - Google Patents
New substituted azetidinones as anti-inflammatory and antidegenerative agents Download PDFInfo
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- LV13338B LV13338B LVP-05-69A LV050069A LV13338B LV 13338 B LV13338 B LV 13338B LV 050069 A LV050069 A LV 050069A LV 13338 B LV13338 B LV 13338B
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Claims (13)
1 LV 13338 Izgudrojuma formula 1. Savienojums ar formulu (I):
R1 O vai tā farmaceitiski pieņemama sāls, kurā: R ir Ci-6alkilgrupa; R1 ir Ci.6alkilgrupa vai Ci.6alkoksi-Ci-6alkilgrupa; M ir (1) ūdeņraža atoms, (2) Ci.6alkilgrupa, (3) hidroksi-Ci.6alkilgrupa, (4) halogēn-Ci-ealkilgrupa, (5) C2-6alkenilgrupa, vai (6) Ci.6alkoksi-Ci.6alkilgrupa: Ra un Rb katrs individuāli ir (1) ūdeņraža atoms, (3) halogēna atoms, (4) karboksilgrupa, (5) C-i-ealkoksigrupa, (6) fenilgrupa, (7) Ci-ealkilkarbonilgrupa, (8) di-(Ci.6alkil)aminogrupa, (9) hidroksilgrupa; R2 un R3 katrs neatkarīgi viens no otra ir (1) ūdeņraža atoms, (2) Ci-6alkilgrupa, (3) halogēna atoms, (4) karboksilgrupa, (5) Ci.6alkoksigrupa, (6) fenilgrupa, (7) C-|.6alkilkarbonilgrupa, (8) amino-C2-3alkiloksikarbonilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar C-i-6alkilgrupu, (9) amino-C2-3alkilaminokarbonilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar C-i-aalkilgrupu, 2 (10) hidroksilgrupa, (11) aminokarbonilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar C-i-ealkilgrupu, (12) hidroksimetilgrupa, (13) aminokarboniloksi-C^alkilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar C-i-ealkilgrupu, (14) ciāngrupa, (15) morfolīnkarbonilfenilgrupa, (16) aminogrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci-ealkilgrupu, vai R2 un R3 var kopā veidot metilēndioksigrupu vai furāna ciklu, (17) morfolTnkarbonilgrupa; R4 ir II
q-c-y-n \ kur: Q ir kovalentā saite un Y ir
R12 ir ūdeņraža atoms vai C-i.3alkilgrupa; R7 un Re katrs individuāli ir (a) ūdeņraža atoms, (b) C^alkilgrupa, (c) Ci.6alkoksi-C2-3alkilgrupa, (d) hidroksi-C2.6alkilgrupa, (e) polihidroksi-C2-6alkilgrupa, (f) karboksamido-C-i.6alkilgrupa, (h) Ci.6alkanoilgrupa (i) aizvietota fenilgrupa vai fenil-Ci.6alkilgrupa, kur aizvietotāji ir Χ1 un X2, kā ir minēts zemāk, (j) C2-6alkenilgrupa, (k) C6-ioCikloalkenilgrupa, (l) heteroaril-Ci-ealkilgrupa, kur heteroarilgrupa ir piridinilgrupa, imidazolilgrupa, triazoliigrupa, benzilimidazolilgrupa vai furilgrupa, (m) karboksi-Ci-6alkilgrupa, (n) karbo-Ci-ealkoksi-Cļ^alkilgrupa, (o) fenilsulfonilgrupa, (q) benziloksigrupa, 3 LV 13338 (r) morfolinil-Ci.3alkilsulfonilgrupa, (s) tetrahidropiranilgrupa, (t) amino-Ci.3alkilsulfonilgrupa, kur aminogrupa ir neobligāti mono-vai diaizvietota ar Ci_6alkilgrupu, (u) aminokarbonilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci-ealkilgrupu, (v) aminokarboniloksi-C2-6alkilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci.6alkilgrupu, (w) azabiciklogrupa no 7 ITdz 12 atomiem, (x) di-Ci-3alkilamino-C2-6alkilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci-6alkilgrupu, (y) bicikloalkilgrupa no 7 līdz 12 atomiem, (z) C3-iocikloalkilgrupa, kas neobligāti aizvietota ar Cļ.ealkilgrupu, (aa) pirazolidinilgrupa, (bb) aizvietota piperidinilgrupa vai pirolidinilgrupa, kur aizvietotājs ir ūdeņraža atoms, Ci^alkilgrupa, hidroksi-C-i.3alkilbenzilgrupa, karboksamidogrupa vai aminogrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci-6alkilgrupu, (cc) aizvietota pirolidinilgrupa, kur aizvietotājs ir karboksamidogrupa vai aminogrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci-6alkilgrupu, (dd) pirimidinilgrupa, (ee) N-ciān-N'-fenilamidinogrupa, (ff) fosfon-Ci.6alkilgrupa vai (gg) a-Ci-3alkilbenzilgrupa vai mono- vai diaizvietota benzilgrupa vai mono- vai diaizvietota piridilmetilgrupa, kur aizvietotāji ir Xi un X2, kur: Xi ir (l) ūdeņraža atoms, (2) halogēna atoms, (3) Ci-6alkilgrupa, (4) halogēn-Ci^alkilgrupa, (5) C2-6alkenilgrupa, (6) hidroksi-Ci-ealkilgrupa, (7) Ci-6alkilkarbonilgrupa, (8) Cļ-ealkilkarbonilaminogrupa, (9) CN, (10) CF3, (11) CH30, (12) aminogrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci.6alkilgrupu, (13) karboksilgrupa, vai (14) fenilsulfonilaminokarbonilgrupa; X2 ir ūdeņraža atoms, halogēna atoms vai Ci-6alkilgrupa; n ir 1,2, 3, 4 vai 5; Rg ir izvēlēts no rindas: C-Malkilgrupa un Ci.3alkoksi-Ci.3alkilgrupa; vai fenilgrupa, fenil-Cļ.salkilgrupa, piridilgrupa un piridil-Ci-3alkilgrupa; R10 un Rn, katrs neatkarīgi viens no otra, ir izvēlēts no ūdeņraža atoma, Ci_4alkilgrupas vai C^alkoksi-Ci-salkilgrupas, vai kopā ir 0=; vai 4 Rr un R8 ir savienoti kopā, veidojot mono- vai diaizvietotu ciklu no 4, 5, 6, vai 7 atomiem vai no 7 līdz 12 atomiem, tādu kā (1) piperidinilgrupa vai homopiperidinilgrupa, (2) piperazinilgrupa, (3) morfolinilgrupa, tiomorfolinilgrupa vai 1,1-diokso-4-tiomorfolinilgrupa, (4) pirolidinilgrupa, (5) pirilgrupa, (6) imidazolilgrupa, (7) triazolilgrupa, (8) piesātināta azabiciklogrupa no 7 līdz 12 atomiem, (9) azaspirogrupa ar 3 līdz 9 oglekļa atomiem, kur minētais cikls ir piesātināts, (10) tetrazolilgrupa, (11) pirazolidinilgrupa, (12) dihidrodimetoksiizohinolilgrupa, (13) azetidinilgrupa, vai (14) dizabiciklogrupa no 7-12 atomiem, kur aizvietotāji katrs ir izvēlēts no rindas: ūdeņraža atoms un Ct.3alkilgrupa, benziloksikarbonilgrupa, karboksilgrupa, fenil-Ci.3alkilaminokarbonilgrupa, pirolidinilmetilgrupa, hidroksi-Ci-3alkilgrupa, Ci-6alkoksigrupa, Cļ^alkoksikarbonilgrupa, aminokarbonilgrupa, kur aminogrupa ir neobligāti mono- vai diaizvietota ar Ci-6alkilgrupu, un oksogrupa; vai -N(R7)R8 var būt lizīna palieka; vai Re un Rg ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 6-7 atomiem un saturošu divus heteroatomus, kas ir slāpekļa atoms, pie kura pievienoti R8 un Rg; minētie cikli ietver piperazinilciklu un homopiperazinilciklu; vai R8 un Rg ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5-7 atomiem un saturošu vienu heteroatomu, kas ir slāpekļa atoms pie kura ir pievienots Rg! vai Rg un Ri2 ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5, 6 vai 7 atomiem, minētais cikls satur vienu heteroatomu, kas ir slāpekļa atoms, pie kura pievienots R9; vai R-io un Rļ2 ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5, 6 vai 7 oglekļa atomiem; vai Re un Rii ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5, 6 vai 7 atomiem, minētais cikls satur vienu heteroatomu, kas ir slāpekļa atoms pie kura pievienots R8; un aizvietotāji ir neatkarīgi izvēlēti no ūdeņraža atoma un Ci.3alkilgrupas.
2. Savienojums pēc 1. punkta, kurā: R ir Ci.6alkilgrupa; R1 ir Ci-6alkilgrupa vai Ci.6alkoksi-C-|.6alkilgrupa; M ir (1) ūdeņraža atoms, (2) Ci.6alkilgrupa, (3) hidroksi-Ci-6alkilgrupa, (4) halogēn-Ci-6alkilgrupa, (5) C2-6alkenilgrupa, vai 5 LV 13338 (6) Ci.6alkoksi-Ci.6alkilgrupa; Ra ir (1) ūdeņraža atoms, (2) Ci.6alkilgrupa, (3) halogēna atoms, (4) karboksilgrupa, (5) Ci^alkoksigrupa, (6) fenilgrupa, (7) Ci-6alkilkarbonilgrupa, (8) di-(C-i.6alkil)aminogrupa, Rb ir ūdeņraža atoms vai Ci_6alkilgrupa, R2 un R3 katrs neatkarīgi viens no otra ir (1) ūdeņraža atoms, (2) Cļ-ealkilgrupa, (3) halogēna atoms, (4) karboksilgrupa, (5) Cļ^alkoksigrupa, (6) fenilgrupa, (7) Cļ-ealkilkarbonilgrupa, (8) di-(C-i_6alkil)aminogrupa, R2 un R5 var būt savienoti kopā, veidojot metiiēndioksigrupu vai furāna ciklu; R4 ir \\ -o-c- y-n \ kur: Q ir kovalentā saite un
R12 ir ūdeņraža atoms vai Ci.3alkilgrupa; R7 un Rs katrs individuāli ir (a) ūdeņraža atoms, (b) Ci.6alkilgrupa, (c) Ci-6alkoksi-C2-3alkilgrupa, (d) hidroksi-C2-6alkilgrupa, (e) karboksamido-Ci-6alkilgrupa, (f) Ci.6alkanoilgrupa (g) fenilgrupa vai fenil-Ci-galkilgrupa, (h) C2-6alkenilgrupa, (i) C6-iocikloelkenilgrupa, 6 (j) heteroaril-Ci-6alkilgrupa, kur heteroarilgrupa ir piridinilgrupa, imidazolilgrupa, triazolilgrupa, benzilimidazolilgrupa vai furilgrupa, (k) karboksi-Ci-6alkilgrupa vai karbo-Ci-6alkoksi-C-i.6alkilgrupa, (l) Ci.6alkilsulfonilgrupa, (m) benziloksigrupa, (n) morfolinil-Ci.3alkilsulfonilgrupa, (o) amino-Ci.3alkilsuifonilgrupa, kur aminogrupa ir neobligāti aizvietota ar Ci-6alkilgrupu, (p) aminokarbonilgrupa, kur aminogrupa ir neobligāti aizvietota ar Ci.6alkilgrupu, (q) aminokarboniloksi-Ci-6alkilgrupaf kur aminogrupa ir neobligāti aizvietota ar Ci-6alkilgrupu, (r) di-Ci.3alkilamino-Ci.6alkilgrupa, kur aminogrupa ir neobligāti aizvietota ar Ci-6alkilgrupu, (s) pirazolidinilgrupa, (t) piperidinilgrupa, (u) pirolidinilgrupa, (v) pirimidinilgrupa, (w) C3.iocikloalkilgrupa, (x) a-Cļ-salkilbenzilgrupa vai mono- vai diaizvietota benzilgrupa vai mono- vai diaizvietota piridilmetilgrupa, kur aizvietotāji ir Xi un X2l kur: Xi ir (1) ūdeņraža atoms, (2) halogēna atoms, (3) Cļ^alkilgrupa, (4) halogēn-Ci.6alkilgrupa, (5) C2.6alkenilgrupa, (6) hidroksi-Ci-6alkilgrupa, (7) Ci.6alkilkarbonilgrupa, (8) Ci.6alkilkarbonilaminogrupa, (9) di-(Ci-3alkil)aminogrupa, (10) karboksilgrupa, X2 ir ūdeņraža atoms, halogēna atoms vai Ci.6alkilgrupa; n ir 1,2, 3 vai 4; Rg ir izvēlēts no rindas: ūdeņraža atoms, Ci.4alkilgrupa un Ct-3alkoksi-C-usalkilgrupa; R10 un Rn, katrs neatkarīgi viens no otra, ir izvēlēts no ūdeņraža atoma, C^alkilgrupas vai C-|.3alkoksi-Ci.3alkilgrupas; vai R7 un Re ir savienoti kopā, veidojot mono- vai diaizvietotu ciklu, kas ir izvēlēts no: (1) piperidinilgrupa, (2) piperazinilgrupa, (3) morfolinilgrupa, (4) pirolidinilgrupa, (5) pirilgrupa, (6) imidazolilgrupa, (7) triazolilgrupa, (8) tetrazolilgrupa, (9) pirazolidinilgrupa, (10) azetidinilgrupa, 7 LV 13338 kur aizvietotāji katrs ir izvēlēts no rindas: ūdeņraža atoms un Ci-3alkilgrupa, benziloksikarbonilgrupa, karboksilgrupa, fenil-Ci-3alkilaminokarbonilgrupa, pirolidinilmetilgrupa, hidroksi-Ci.3alkilgrupa, Ci-6alkoksigrupa, C-ualkoksikarbonilgrupa, un oksogrupa; vai R8 un R9 ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 6-7 atomiem un saturošu divus heteroatomus, kas ir slāpekļa atoms, pie kura pievienoti Ra un Rg; minētie cikli ietver piperazinilciklu un homopiperazinilciklu; vai Rg un R10 ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5-7 atomiem un saturošu vienu heteroatomu, kas ir slāpekļa atoms, pie kura ir pievienots Rg; vai R9 un R12 ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5, 6 vai 7 atomiem, minētais cikls satur vienu heteroatomu, kas ir slāpekļa atoms, pie kura pievienots R9; vai R10 un R12 ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5, 6 vai 7 oglekļa atomiem; vai R8 un Rn ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 5, 6 vai 7 atomiem, minētais cikls satur vienu heteroatomu, kas ir slāpekļa atoms pie kura pievienots R8; un aizvietotāji ir neatkarīgi izvēlēti no ūdeņraža atoma un Ci.3alkilgrupas.
3. Savienojums pēc 2. punkta, kurā: R ir Ci-3alkilgrupa; R1 ir Ci-3alkilgrupa; M ir (a) Ci-6alkilgrupa, (b) C2-6alkenilgrupa, R2 ir (a) ūdeņraža atoms, (b) Ci.6alkilgrupa vai Ci-6alkoksigrupa, R3 ir ūdeņraža atoms, vai R2 un R3 ir savienoti kopā, veidojot metilēndioksigrupu vai furāna ciklu; R7 un R8 katrs neatkarīgi viens no otra, ir izvēlēts no rindas: (a) ūdeņraža atoms, (b) Ci.3alkilgrupa, (c) Ci_3alkoksi-C2-3alkilgrupa, (d) C3.7cikloalkilgrupa, (e) hidroksi-C2-3alkilgrupa, (f) karbo-Cļ^alkoksimetilgrupa, (g) aizvietota benzilgrupa, kur aizvietotāji ir Χ-ι un X2, kur: Xi ir ūdeņraža atoms un X2 ir: (1) ūdeņraža atoms, (2) halogēna atoms, (3) Ci.3alkilgrupa, n ir 1,2 vai 3; Rg, R-io un R-n, katrs neatkarīgi viens no otra, ir izvēlēts no rindas: ūdeņraža atoms, Ci.4alkilgrupa un Ci^alkoksi-C^alkilgrupa; R7 un R8 ir savienoti kopā, veidojot aizvietotu ciklu, kas ir izvēlēts no rindas: (1) piperidinilgrupa, (2) piperazinilgrupa, 8 (3) morfolinilgrupa, vai Re un Rg ir savienoti kopā, veidojot mono- vai diaizvietotu piesātinātu monociklu no 6-7 atomiem un saturošu divus heteroatomus, kas ir slāpekļa atomi pie kuriem ir pievienoti Re un Rg.
4. Savienojums pēc 1. punkta ar formulu:
kurā A ir: -NHCH2CH2N(CH3)2 -N(CH3)CH2CH2N(CH3)2 -N(Et)CH2CH2N(CH3)2 -NHCH2CH2N(Et)2 -NHCH2CH2-(4-morfolinilgrupa) -N(CH3)CH2CH2-(4-morfolinilgrupa) -N(CH3)CH2CH2N(CH2CH2OCH3)2 -N(CH3)CH2CH2N(Et)2 -N(Ph)CH2CH2N(CH3)2 -N(CH3)CH2CH2CH2N(CH3)2 -NHCH2CH2N(i-Pr)2 -N(CH3)CH2CH2N(0)(CH3)2 -N(CH3)CH2CH2N(i-Pr)2 -NH-S02CH2CH2-(4-morfolinilgrupa) -NH-S02CH2CH2N(CH3)2 -NHCH2CH2-(4-imidazolilgrupa) -NHCH2CH2-(1 -piperidinilgrupa) -N(CH3)CH2CH2-(1-piperidinilgrupa) -N(CH3)CH2CH2NHCH3 -N(CH3)CH2CH2N(CH3)Ac -NHCH2CH2-(1-pirolidinilgrupa) -N(CH3)CH2CH2-(1-pirolidiniigrupa) -NHCH2CH2-(1 H-1,2,4-triazoM-ilgrupa) -NHCH2CH2-(1-imidazolilgrupa) -NHCH2CH2-(3-azabiciklo[3.2.2]non-3-ilgrupa) -NHCH2CH2-(3-azaspiro[5.5]undec-3-ilgrupa) -NHCH2CH2-(2H-tetrazol-2-ilgrupa) -NHCH2CH2-(2H-tetrazol-1-ilgrupa) -NHCH2C(0)-Pro-NHCH2Ph 9 9 LV 13338 -N(CH3)CH2CH2-(3-azabiciklo[3.2.2]non-3-ilgrupa) -N(CH3)CH2CH2-(4-imidazolilgrupa) -N(CH3)CH2CH2N(CH3)Ac -N(CH3)CH2CH2N(CH3)C(0)NHCH3 -N(CH3)CH2CH2N(CH3)S02CH3 -N(CH3)CH2CH2-(3-azabiciklo[3.2.2]non-3-ilgrupa) -NHCH2CH2-(1,1-diokso-4-tiamorfolinilgrupa) -N(CH3)CH2CH2-(1,1-diokso-4-tiamorfolinilgrupa) 4-dimetilaminoanilinogrupa -NHCH2CH2-(1-benzil-1H-imidazol-2-ilgrupa) -N(CH3)CH2CH2-(2-pridilgrupa) -N(CH3)(1-azabiciklo[2.2.2]okt-3-ilgrupa) -NHCH2CH2-(4-benziloksikarbonil-1-piperazinilgrupa) 1,2-dietilpirazolidin-4-ilaminogrupa 2-(1-S-pirolidinilmetil)-1-pirolidinilgrupa -NHCH2CH2-(4-hidroksi-1-piperidinilgrupa) -NHCH2CH2-(1-homopiperidinilgrupa) -N(CH3)CH2CH2-(1-homopiperidinilgrupa) -NHCH2CH2-(3-hidroksi-1-piperidinilgrupa) -N(CH3)CH2CH2-(3-hidroksi-1-piperidinilgrupa) -N(CH3)CH2CH2N(CH3)CH2Ph -N(CH3)CH2CH2-(4-benziloksi-1-piperidinilgrupa) -N(CH3)CH2CH2-(4-hidroksi-1-piperidinilgrupa) -N(CH3)CH2CH2-(4-okso-1-piperidinilgrupa) -NHCH2CH2-(3-hidroksi-1-pirolidinilgrupa) -N(Et)CH2CH2-(1-piperidinilgrupa) -N(CH2Ph)CH2CH2-(1-piperidinilgrupa) -N(CH2Ph)CH2CH2N(CH3)2 -N(CH3)CH2CH2-(3-hidroksi-1-pirolidinilgrupa) -N(3-pikolil)CH2CH2-(1-piperidinilgrupa) -NHCH(CH3)CH2CH2CH2N(Et)2 -NHCH2CH2-(2-S-hidroksimetil-1-piroiidinilgrupa) -N(CH3)CH2CH2-(4-t-butoksikarbonil-1-piperazinilgrupa) -N[CH2CH2N(CH3)2]2 -N[CH2CH2N(Et)2]2 -N(CH3)CH2CH2N(CH3)(3-pikolilgrupa) 3,5-dimetil-1-piperazinilgnjpa -N(CH3)CH2CH2N(0)(CH3)CH2Ph -N(CH3)CH2CH2N(CH3)(4-pikolilgrupa) 2-S-(N-benzil-N-metilaminometil)-1-pirolidinilgrupa -N(CH3)CH2CH2N(CH3)(2-pikolilgrupa) -N(CH3)CH2CH2(1-piperazinilgrupa) 1 -homopiperazinilgrupa -N(CH3)CH2CH2N(CH3)CH2CH2Ph 2-(1 -R-pirolidinilmetiI)-1 -pirolidinilgrupa 4-benzil-1 -homopiperazinilgrupa -N(CH3)CH2CH2N(CH3)(1-naftalenilmetilgrupa) -N(CH3)CH2CH2N(CH3)(2-naftalenilmetilgrupa) -N(CH3)CH2CH2N(CH3)CH(CH3)Ph -N(CH3)CH2CH2N(CH2Ph)2 1 -etil-3-piperidinilaminogrupa -N(CH3)CH2CH2N(CH3)(2-furfurilgrupa) 10 -N(CH3)CH2CH2CH2C(0)NHS02Ph -N(CH3)CH2CH2N(CH3)CH2CH=CH2 -N(CH3)CH2CH2CH2N(CH3)CH2Ph -N(CH3)(CH2)6N(CH3)CH2Ph -N(CH3)CH2CH20C(0)N(CH3)2 -N(CH3)CH2CH2N(CH3)CH2COO-t-Bu -N(CH3)(1-etil-3-piperidinilgrupa) -N(CH3)CH2CH2N(CH3)(tetrahidro-2H-piran-2-ilmetilgrupa) 2,2,6,6-tetrahidrometilpiperidin-4-ilaminogrupa -N(CH3)CH2CH2N(CH3)(4-ciānbenzilgrupa) -N(CH3)CH2CH2N(CH3)(4-metilbenzilgrupa) 4^(CH3)CH2CH2N(CH3)(3-ciānbenzilgrupa) -N(CH3)CH2CH2N(CH3)(4-trifluormetilbenzilgrupa) -N(CH3)CH2CH2N(CH3)(34rifluormetilbenzilgrupa) 4^(CH3)CH2CH2N(CH3)(ciklopropilmetilgrupa) -N(CH3)CH2CH(Ph)N(CH3)2 -N(CH3)(1-benzil-3-piperidinilgrupa) -N(3-pikolilgrupa)CH2CH2N(CH3)CH2Ph -N(CH3)CH2CH2N(CH3)(4-metoksibenzilgrupa) -N(4-pikolilgrupa)CH2CH2N(CH3)CH2Ph -N(2-pikolilgrupa)CH2CH2N(CH3)CH2Ph -N(CH3)CH2CH2N(CH3)(2,4-dimetilbenzilgrupa) -N(CH3)CH2CH2(2,6-dimetil-4-morfolinilgrupa) -N(CH3)CH2CH2N(CH3)C(=N-CN)NHPh -N(CH3)CH2CH2N(CH3)(3-fIuorbenzilgrupa) -N(CH3)CH2CH2N(CH3)(2-hlorbenzilgrupa) -N(CH3)CH2CH2N(CH3)(3-metoksibenzilgrupa) -N(CH3)CH2CH2N(CH3)(3,5-dimetoksibenzilgrupa) -N(CH3)(1-benzil-4-piperidinilgrupa) -N(CH3)CH2CH2N(CH3)(2-adamantilgrupa) -N(CH3)(4-piperidinilgrupa) 5-metil-2,5-diazabieiklo[2.2.1]hept-2-ilgrupa -N(CH3)CH2CH2CH2N(CH3)CH2CH3 -N(CH3)( 1 -metil-4-piperidinilgrupa) -N(CH3)(1-propil-4-piperidinilgrupa) -N(CH3)(1-etil-4-piperidinilgrupa) -N(CH3)CH2CH(CH3)N(CH3)CH2Ph -N(CH3)CH2CH(CH3)N(CH3)2 -N(CH3)CH2CH2N(CH3)(biciklo[2.2.1]hept-2-i!grupa) -N(CH3)CH2CH2NH(2-adamantilgrupa) -N(CH3)CH2CH2N(CH3)(6,6-dimetilbicik!o[3.1.1 ]hept-2-ilgrupa) -N(CH3)CH2CH2N(CH3)(biciklo[3.2.1]okt-2-ilgrupa) -N(CH3)CH2CH2N(CH3)(1 -cikloheksen-1 -ilgrupa) -N(CH3)CH2CH2NHC(CH3)2CH=CH2 2-S-karboksamTd-1-pirolidinilgrupa 2-hidroksimetil-1 -piroiidinilgrupa 2-dimetilamino-1-pirolidinilgrupa -N(CH3)CH2CH2N(CH3)(cikloheksilmetilgrupa) -N(CH3)CH2CH2N(CH2CH=CH2)C(CH3)2CH=CH2 -N(CH3)CH2CH2N(CH3)(4-etilcikloheksilgrupa) -N(CH3)CH2CH2N(CH3)(2-etilcikloheksilgrupa) -N(CH3)CH2CH2N(CH3)(4-metilcikloheksilgrupa) 11 LV 13338 -N(CH3)CH2CH2N(CH3)(cikloheksilgrupa) -N(CH3)CH2CH2N(CH3)CH2COOH-TFS -N(CH3)CH2CHN(CH3)CH2C(0)N(CH3)2 -N(CH)CH2CH2N(CH3)(cikloheksilmetilgrupa) vai -NHCH2CH2N(Et)CH2CH2OCH3
5. Savienojums pēc 1. punkta ar formulu: Et
Pr kur R ir: -CH3 4-fluorfenilgrupa 3-hlorfenilgrupa fenilgrupa benzilgrupa H i-Pr 1- Bu -CH2COOEt -CH2COOH Et Pr 2- pirimidiniigrupa -CH2CH20C(0)NHCH3 ciklopropilgrupa vai -CH2CH2OH
6. Savienojums pēc 1. punkta ar formulu: Et O
Pr kurā n ir 0 un A ir: -N(CH3)CH2CH2N(CH3)2 12 4-metil-1 -piperazinilgrupa -N(CH3)CH2CH2N(CH3)CH2Ph 4-ciklopropil-1-piperazinilgrupa 1-piperazinilgrupa vai 4-(2-hidroksietil)-1-piperazinilgrupa.
7. Savienojums pēc 1. punkta ar formulu:
kurā n ir 0 un R4' un A ir minēti zemāk: R* A Et -N (CH3)CH2CH2N(CH3)2.
8. Savienojums pēc 1. punkta ar formulu:
13LV 13338 kurā n ir 0 un R3 un A ir minēti zemāk: R3 A H -N (CH3)CH2CH2N(CH3)2.
9. Savienojums pec 1. punkta ar formulu:
O kurā n ir 0 un R2, R3 un A ir minēti zemāk: r3 r2 A H -CON(CH3)2 -N(CH3)CH2CH2N(CH3)2 H -COOH -N(CH3)CH2CH2N(CH3)2 H -CH2OH -N(CH3)CH2CH2N(CH3)2 H och3 -N(CH3)CH2CH2N(CH3)2 OCH3 H -N(CH3)CH2CH2N(CH3)2 H CN -N(CH3)CH2CH2N(CH3)2 H OEt -N(CH3)CH2CH2N(CH3)CH2Ph H 2-(4-morfolinkarbonilfenilgrupa) -N(CH3)CH2CH2N(CH3)CH2Ph H och3 4-metil-1-piperazinilgrupa H Cl -N(CH3)CH2CH2N(CH3)2 H Cl -N(CH3)CH2CH2N(Et)2 H Cl -N(CH3)CH2CH2N(I-Pr)2 H Cl -N(CH3)CH2CH2N(CH3)CH2Ph vai OCH., ch3 -N(CH3)CH2CH2N(CH3)?
10. Savienojums pec 1. punkta ar formulu:
14 kurā R2, R6 un A ir minēti zemāk: r2 Re A CH3 ch3 ch3 H ch3 ch3 ch3 OH -N(CH3)CH2CH2N(CH3)2 -N(CH3)CH2CH2N(Et)2 -N(Et)CH2CH2N(CH3)2 oder -N(CH3)CH2CH2N(CH3)2.
11. {S-(R*,S*)]-2-(4-{[(4-Metil)piperazin-1 -il]karbonii}fenoksi)-3,3-dietil-N-[1-(3,4-metilēndioksifenil)butil]-4-okso-1-azetidinkarboksamīds vai tā farmaceitiski pieņemamā sāls.
12. Farmaceitiska kompozīcija, kas ietver savienojumu pēc jebkura no iepriekšējiem punktiem un farmaceitiski pieņemamu nesēju.
13. Savienojuma pēc jebkura no 1. līdz 11. punktam pielietojums medikamenta ražošanai, kas paredzēts cilvēka leikocītu elastāzes inhibēšanai.
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| US5420010A (en) * | 1993-07-30 | 1995-05-30 | Merck & Co., Inc. | Assay for evaluating inhibition of polymorphonuclear leukocyte elastase by N-substituted azetidinones |
| AU5014496A (en) * | 1995-03-23 | 1996-10-08 | Japan Tobacco Inc. | Diphenylmethyl-azetidinone compounds and elastase inhibitor |
| US5523233A (en) * | 1995-05-03 | 1996-06-04 | Merck & Co., Inc. | Enzymatic hydrolysis of 3,3-diethyl-4-[(4-carboxy)phenoxy]-2-azetidinone esters |
| US5808056A (en) * | 1995-10-31 | 1998-09-15 | Merck & Co., Inc. | Process for preparing substituted azetidinones |
| AU701386B2 (en) * | 1995-10-31 | 1999-01-28 | Merck & Co., Inc. | Process for preparing substituted azetidinones |
| JP2000502079A (ja) * | 1995-12-08 | 2000-02-22 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | アテローム性動脈硬化症の治療のための単環β―ラクタム誘導体 |
| TR199802160T2 (xx) * | 1996-04-26 | 1999-04-21 | Smithkline Beecham Plc | Ateroskleroz tedavisi i�in azetidinon t�revleri. |
| AU4654199A (en) * | 1998-07-23 | 2000-02-14 | Shionogi & Co., Ltd. | Monocyclic beta-lactam compounds and chymase inhibitors containing the same |
| RU2217196C2 (ru) * | 2002-02-28 | 2003-11-27 | Небольсин Владимир Евгеньевич | Способ индукции дифференцировки клеток |
| FR2937972B1 (fr) * | 2008-11-04 | 2013-03-29 | Galderma Res & Dev | Derives d'oxoazetidine, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
| KR101421785B1 (ko) * | 2009-03-09 | 2014-07-22 | 다이호야쿠힌고교 가부시키가이샤 | 프로스타글란딘 ｄ 합성 효소를 저해하는 피페라진 화합물 |
| FR2981933B1 (fr) * | 2011-11-02 | 2013-11-15 | Galderma Res & Dev | Derives d'oxoazetidine, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ228600A (en) * | 1988-04-11 | 1992-02-25 | Merck & Co Inc | 1-(benzylaminocarbonyl)-4-phenoxy-azetidin-2-one derivatives |
| IL99658A0 (en) * | 1990-10-15 | 1992-08-18 | Merck & Co Inc | Substituted azetidinones and pharmaceutical compositions containing them |
| WO1993000332A1 (en) * | 1991-06-25 | 1993-01-07 | Merck & Co., Inc. | Substituted azetidinones as anti-inflammatory and antidegenerative agents |
-
1993
- 1993-10-18 TW TW082108642A patent/TW275621B/zh active
- 1993-10-18 MY MYPI93002128A patent/MY128261A/en unknown
- 1993-10-18 CA CA002108584A patent/CA2108584C/en not_active Expired - Lifetime
- 1993-10-19 IL IL10732193A patent/IL107321A/en not_active IP Right Cessation
- 1993-10-19 HR HR07/991,838A patent/HRP931309A2/xx not_active Application Discontinuation
- 1993-10-22 PT PT93308421T patent/PT595557E/pt unknown
- 1993-10-22 DE DE69333563T patent/DE69333563T2/de not_active Expired - Lifetime
- 1993-10-22 ES ES93308421T patent/ES2224095T3/es not_active Expired - Lifetime
- 1993-10-22 AT AT93308421T patent/ATE270273T1/de active
- 1993-10-22 DK DK93308421T patent/DK0595557T3/da active
- 1993-10-22 EP EP93308421A patent/EP0595557B1/en not_active Expired - Lifetime
- 1993-10-26 RU RU95109936A patent/RU2148056C1/ru active
- 1993-10-26 MX MX9306666A patent/MX9306666A/es not_active IP Right Cessation
- 1993-10-26 PL PL93308545A patent/PL308545A1/xx unknown
- 1993-10-26 NZ NZ257755A patent/NZ257755A/en unknown
- 1993-10-26 CN CN93119648A patent/CN1043884C/zh not_active Expired - Fee Related
- 1993-10-26 CZ CZ951068A patent/CZ106895A3/cs unknown
- 1993-10-26 AU AU50283/93A patent/AU663806B2/en not_active Expired
- 1993-10-26 SK SK537-95A patent/SK53795A3/sk unknown
- 1993-10-26 WO PCT/US1993/010268 patent/WO1994010142A1/en not_active Application Discontinuation
- 1993-10-26 HU HU9501184A patent/HUT72084A/hu unknown
- 1993-10-27 DZ DZ930115A patent/DZ1724A1/fr active
- 1993-10-27 SI SI9300566A patent/SI9300566A/sl unknown
- 1993-10-27 JP JP5292692A patent/JPH082868B2/ja not_active Expired - Lifetime
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1995
- 1995-04-26 FI FI951992A patent/FI951992A0/fi unknown
- 1995-04-26 NO NO951593A patent/NO305697B1/no not_active IP Right Cessation
- 1995-04-27 KR KR1019950701629A patent/KR950704250A/ko not_active Application Discontinuation
- 1995-06-30 HU HU95P/P00639P patent/HU211619A9/hu unknown
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2005
- 2005-06-08 LV LVP-05-69A patent/LV13338B/en unknown
- 2005-08-29 CY CY0500046A patent/CY2529B1/xx unknown
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