PT99262A - Processo para a preparacao de derivados de amidas de aminoacidos perptidicos e de composicoes farmaceuticas que os contem - Google Patents

Processo para a preparacao de derivados de amidas de aminoacidos perptidicos e de composicoes farmaceuticas que os contem Download PDF

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PT99262A
PT99262A PT99262A PT9926291A PT99262A PT 99262 A PT99262 A PT 99262A PT 99262 A PT99262 A PT 99262A PT 9926291 A PT9926291 A PT 9926291A PT 99262 A PT99262 A PT 99262A
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alkyl
formula
compound
hydrogen atom
treatment
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PT99262A
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Peter Raddatz
Dieter Dorsch
Claus-Jochen Schmitges
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Merck Patent Gmbh
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    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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    • C07D213/00—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
    • 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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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • A61P31/12—Antivirals
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    • A61P31/18—Antivirals for RNA viruses for HIV
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
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    • 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
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
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    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
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    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
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    • C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
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    • C07K5/0207—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)4-C(=0), e.g. 'isosters', replacing two amino acids
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    • C07—ORGANIC CHEMISTRY
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    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Claims (2)

  1. Ampolas de injecggo ííuma solução de 100 g de dicloridrato de B~betaAla-ABH?-I le-~A. 'PA em 4 li troe de água bidestilada ajusta-se o valor do pIT de maneira a ser igual a 6,5 com ácido clorídrico 2 normal» filtra-se para esterilização e embala-se em ampolas para in-jecçBes. Liofiliza-se em condiçttes eatáreis e fecham-se as ampolas sob condiçttes de esterilização* Cada ampola de injeeçâo contém ICC mg da substância activa*
    Supositórios Funde-se uma mistura de 50 g do composto PCC~betaAla-ABHP-Ile„ -A.TA com 10 g de lecitina de semente de soja e 140 g de manteiga de cacau» despeja-se em formas e deixa-se arrefecer* Cada supositório contém 250 mg da substância activa* RSIYINJOICAyCKS 1*· - Processo para a preparação de derivados de aaidas de arainoácidoe peptidicos de fórmula geral I» X-ÍSH-crf-COj^^-ÍCH-L-CO-HíWCHR^^-Ca^lí-Cim^CO- η Ώ. n C B, - (HB-CBr-CO ) -ΐ-ΪΓ P (I) na q.ual X significa Ií, a5-.C«Caii;i9~V,2a~C~C4'~# *χ3*°αΗ2α*00'*# A-sOg-t r^^^h^-íx-, R12~xi-c{#N;?)-S!r« -can2arcc-, Acc-c^cc-, a^s-o^-cc-, a^-c-ícUgCHgOjj.-.c^ggj-CG- ou A3^~ca:J2m~cc~ aiPí w significa 0 ou NHi II3·* li2» Λ?, RS o A9 significam respeetivamente» i» A» Ar» Ar-alqull, iet» Ait-alquil, cxcloalqullo com 3 a 7 átomos de carbono insubstituído ou raonossubstituído ou poli3substituí do por A» Αϋ e/ou 3a-.» cieicalquil-alqull coa 4 a 11 átomos de carbono» oicieloalquilo uu triciclos rquilo cada um com re spe ctivamente S a 18 átomos de Jt significa (H» OIT)» (H* HHg) ou *Ci Λ AC AI R, 1# E e H significam cada um raspectivamente ;· ou Ai 6 A 3igaifica Ar-E-í-quil ou cieiualquilalquil com 4 - H átomos de C, "|í> 11 ir“uR significa também um grupo pirroliâino» piperidino» morfolino ou piperazino nio substituído ou substituído por A, Cih KiJ2, HiJA» NAg» KIAc» I^-CC-C^gg-G- -R9, iÍj-€0-0-.CxIÍ2x-E9, hiàroxi-aiquii» COOU, COCA, CCHHg» amino-alquil» ITAli-alquii, AgE-alquil, Ayf ^ alquil A a®, X:-CO-iB2» il'-CC-HIIA, guanldinilo ou guanii nil-^lquilo, A2 significa 5, A, Ar-alquil ou CNi a significa 2 ou 3i m 6 x significam cada um respectivamente
    ο, : a* ρ e r Ar litt U 2, 3t 4, 5» 6, 7, 6, 9 ou ÍC* significam C, 1, 2 ou 3, significa fenilo nSo substituído ou monossubsti-tuído ou p oli ssub 8 ti tuí d o per A, CA# I'ai, C?y C:.:, •íOg * bidroxi-alquil, *í=.r2, -ί.Ά# JAg* *JHAc* λ.
  2. 2>">A 9 bAf $?C—a* uGg-A* iaCgjiídgt SOgd.-.A* 0CC;j* COCA# CGdiJg#· 011» aciíio-ulquil* .A:i-alquil, A2:Walquii, Ayí^al-quil An^e/ou guanidjmi ..-.d ;uil ou aaítilo nãc substituído, significa um radical heterocíelico pentagonal ou bexagonal saturado ou ηδο saturado com 1 a 4 átomos de :<,* O β/ou 3 que pode ser condensado com um anel de beazeno β/ou moaossubstituíáo ou polissubsti- tuído por A* ! uA , rial t í *?-r| -x*3» 0:-, ΗΟ^, carboniloxigé- nio, jgd» λ :A * ithp* m ^c, : SV-CCCA, HHCOGAr* HHC00- Ci2Ar, ;í:j-sc2-a, sa* si J"*A $ SG2-A, SCgííríg, SO^JA, coo;!, COCA, 0 w2, on, Ar, Ar-alquil, Ar-alcenilo, gX Ac An® -alquil A hidroxi-alquil, amino-alquil, JAN-alquil, A2N-al-quil e/ou A^N^-alquil An® e/ou os seus heteroátomos H β/ou S podem também ser oxidados, significa ?f Cl# 3r ou I, significa A-OC-, Ar-CC-, Ar-alquil-CO- ou A-N r-GG-, significa um aaiSo, que também pode estar ausente se» βία vez dele, no composto de fórmula I, estiver contido um grupo carboxi sob a forniu dum aaifto car-boxilato, significa um grupo alquiieno ccm 1 a 8 átomos de C € significa alquilo com 1 a 8 átomos de C,
    ea que* em vcs ds u.:: ou aaie grupos podem existir um ou maia grupos -.JA-X-* assim como dos seus sais* caraetertzado pelo facto de* a partir dum derivado fmicional dom derivado de amiaoácido le ffo*..ula X* se liliertar este por tratamento cora um agente solvolisante ou hidrogenolisaa-te ou se faaer reagir um ácido carlsoxílico de fórmula geral II J {XI} na qual ou (a) está ausente* ou significa (¾} (oj .(s.-f-c^ír-co) -* .(^C:^*t-CC)ir^.{CP2}a«C0-,(â) .a -»CG)x{cd2 j·· -c m2~aã3~'jR4 r5-ch?A-cc- »{e} - (w-:::?A-cc )a-&;~(CH2)a-CG-iiH~-c.m2-ca3-cH4a5-C;íR6«o c-éxí-cííH7. -cc), ou ua sea derivado reactivo* com uib composto de fformula III na qual G2 («) significa -(&í^áA*00)a~3H~{C:i2) ~CC~SH~ -c: ? a2~c Aca4K5-c:f ;?A.gg- (iti- (III) *CL. d.*-uC) p** # 0») > -.cc-]jH-Cíia2-ca3-ca4 Ao^-cMaH- mAec) p (c) -K:?-e3a2-ea*~ca4 #-chr6-cc~{íe> (d) <·) *CíírT-»co)p··» -(^ί-ΟίίΛοΟ)^» ou está ausente e eventualmente, num composto de fórmula I se libertar um grupo amino e/ou hidroxi funcionalmente codificado por tratamento co« agentes solvolisantes ou hi drogenoliaantes e/ou se adiar ura grupo acino livre por tratamento com um agente de acilaçfto e/ou para a preparaçSo dum composto de fórmula I em que * (H* Gd) ou (:í, áHg) se reduzir ou se aminar re-áutoramente nua derivado dum aaioastoácido de fórmula I em que λ* * C e/ou se saponificar um éster le fórmula I em que A € diferente de í β/ou se este ri ficar nua ácido de fórmula I em que r * H e/ou se transformar nua composto de fórmula I nu ‘ seu sal por tratamento coai um ácido* 2*1. - Processo de acordo com a reivindicação 1* caracterizado pelo facto de» cono produto final* se obter um àos seguintes ccmpostos de fórmula I a) BOC-ifce—/3 Ala-ABIíP-Ile-A~íA * b) BOC-Pbe-J) Ala-ABd'*-I1«-A ΊΑ í c) 3G v—í be~/3Ala-ACHL:-I le—Α.'.Ί A J d) BD0-y3 Ala-ASl^-ne-iUMi e) C: J^CO-^ Ala-AB'Jj?-I le-AifA* •57, 3β· - ,?roce3ao para a preparaçlo .1« composiçBee farmacêuticas para o tratamento da hipertensEo dependente da renina ou do hiperaldosteroniamo β/ou de doenças provocadas por retrovfrusj earacterizado pelo facto de se misturar uaa quantidade eficaz de «m composto de fdrmula I ou um seu sal de acordo com a rei-vindicaçSo 1, com uma substância veicular e/ou diluente far-maceuticomente aceitável· 4*« - Processo para o tratamento terapêutico ou profiláctico de pacientes humanos que sofrem de hipertensSo sanguínea provocada por renina» hiperaldosteronismo ou doenças provocadas por retro vírus* caracterizado pelo facto de se administrar aos referidos pacientes uaa composição farmacêutica áe acordo com a reivindicação 4 numa dose diária que corresponde* de preferência* a uma quantidade diária de composto de fdraula I compreendida entre cerca de 0,2 e 20 mg/quilograaa de peso corporal* Lisboa, 17 de Outubro de 1991 0 Agente Oficial da Propriedade Industrial
    /L* Américo da Silva Carvalho Agente Oficiei de Propriedade ledfetrial Rua Marquês de Fronteira,N* 127·t.° 1000 LISBOA Tele.3877373*3877453
PT99262A 1990-10-18 1991-10-17 Processo para a preparacao de derivados de amidas de aminoacidos perptidicos e de composicoes farmaceuticas que os contem PT99262A (pt)

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DE4033062A DE4033062A1 (de) 1990-10-18 1990-10-18 Aminosaeurederivate

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KR (1) KR920008066A (pt)
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CA (1) CA2053573A1 (pt)
CS (1) CS316491A3 (pt)
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JPH04316548A (ja) 1992-11-06
KR920008066A (ko) 1992-05-27
EP0481311A3 (en) 1992-11-19
DE4033062A1 (de) 1992-04-23
AU8587791A (en) 1992-04-30
IE913650A1 (en) 1992-04-22
EP0481311A2 (de) 1992-04-22
HU913277D0 (en) 1992-01-28
ZA918294B (en) 1992-07-29
CA2053573A1 (en) 1992-04-19

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