FI89716B - Foerfarande foer framstaellning av terapeutiskt aktiva prolinderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva prolinderivat Download PDF

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Publication number
FI89716B
FI89716B FI853494A FI853494A FI89716B FI 89716 B FI89716 B FI 89716B FI 853494 A FI853494 A FI 853494A FI 853494 A FI853494 A FI 853494A FI 89716 B FI89716 B FI 89716B
Authority
FI
Finland
Prior art keywords
alk
phenylpropyl
compounds
alanyl
amino
Prior art date
Application number
FI853494A
Other languages
English (en)
Finnish (fi)
Other versions
FI853494A0 (fi
FI853494L (fi
FI89716C (sv
Inventor
John T Suh
Edward S Neiss
John R Regan
Jerry W Skiles
Jeffrey N Barton
Paul Menard
James J Mencel
Original Assignee
Usv Pharma Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/649,797 external-priority patent/US4746676A/en
Priority claimed from US06/752,695 external-priority patent/US4749698A/en
Application filed by Usv Pharma Corp filed Critical Usv Pharma Corp
Publication of FI853494A0 publication Critical patent/FI853494A0/fi
Publication of FI853494L publication Critical patent/FI853494L/fi
Publication of FI89716B publication Critical patent/FI89716B/fi
Application granted granted Critical
Publication of FI89716C publication Critical patent/FI89716C/sv

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Classifications

    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 no 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (2)

1. Förfarande för framställning av en terapeutiskt aktiv förening med formeln (1) 5 0 tl Q-C*HCN^~>v I I i) R2 C*iK 10 Y2-C-0 (1) väri Q är Y1-C(0)-C*H(R1)NH-; Yj och Y2 oberoende av varandra är -OH eller -OCH2CH3; 15 ring G är 1T ··*· xpö -CH>Z
20 Z väri G3 är H eller C1-C6-alkoxi; Z är =N-(alk)-M, =N- (alk)-S02M, -(alk)-N( R3)-(alk)-M, -(alk)-N(R3)-(alk)-C(0)-(alk)-M, -(alk)-N(R3)S02-(alk)-M, : 25 -(alk)-N(R3)-(alk)-N(R3)-(alk)-C(0)M, -0-(alk)-C(0)M eller =CH-(alk)-C(0)-(alk)-M, väri (alk) är en kemisk bindning eller -CH2-, M är .....ro-·' B väri A, B och E oberoende av varandra är H, 35 -0CH2C00H, halogen, -NH2, -S02NH2 eller furfurylamino, för- 26 P Q 7 " Λ . w utsatt, att ätminstone en av grupperna A och B är annat än väte; Rx är H eller fenetyl och R2 och R3 oberoende av varantoa är H eller CH3, förutsatt, att dä G är monocyklisk och Z är 5 -(alk)-N(R,)-0(0)-^^^3, - (alk) -N( R3) -S02- (alk) eller mxh 10 -(alk)-N(R3)-(alk)- (' Ύ> . \=£l sä är fenylgruppen substltuerad med furfurylamino, gruppen -0CH2C02H eller ätminstone tvä sulfamoylgrupper, samt far-15 maceutiskt godtagbara syraaddltlons-, alkallmetall- och jordalkalimetallsalter därav, kännetecknat därav, att a) en förening med formeln (2) 20 0 II Q-C*HC0H (2) K väri R2 och Q betecknar samma som ovan, kopplas tili en 25 förening med formeln (3) HD c*ir | (3)
30 Y2“C=0 väri Y2 och substituenterna av G-ringen, inklusive Z, betecknar samma som ovan, under peptidbildningsförhällanden, eller 27 1 , Γ-> * ' : ; ! ϋ b) substituent Ζ anknyts till en förening med for- meln v2i.o 10 genom substitutions- eller kondensationsreaktioner och c) eventuella möjliga skyddsgrupper avlägsnas, och om sä önskas, bildas ett sait av produkten.
2. Förfarande enligt patentkravet 1, kanne-t e c k n a t därav, att man framställer 15 (4R)-4- [5-( sulfamoyl )-4-klor-2- [ ( 2-furylmetyl )amino] ben- soyloxi]-N-[N-[(IS )-1-(hydroxikarbonyl)-3-fenylpropyl]-L-alanyl]-L-prolin eller N- [N- [ (IS )-l-hydroxikarbonyl-3-fenylpropyl] -L-alanyl] -4-[((6-klor-2H-l, 2,4-bensotiadiazin-l, l-dioxid-7-yl )sulfo-20 nyl)amino]-L-prolin eller N- [N- [ (IS )-l-hydroxikarbonyl-3-fenylpropyl] -L-alanyl] -4-[2- ( 3-sulfamoyl-4-klorbensoyl)hydrazin-l-yl]-L-prolin eller N- [N- (IS) -l-hydroxikarbonyl-3-fenylpropyl]-L-alanyl-4-25 ((N-metyl-N-(6-klor-7-sulfamoyl-3,4-dihydro-2H-l,2/4-ben-sotiadiazin-1,l-dioxid-3-yl)metyl)amino)prolin eller ett farmaceutiskt godtagbart syra-, alkalimetall- eller jord-alkalimetallsalt av dessa.
FI853494A 1984-09-12 1985-09-12 Förfarande för framställning av terapeutiskt aktiva prolinderivat FI89716C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US64979784 1984-09-12
US06/649,797 US4746676A (en) 1984-09-12 1984-09-12 Carboxyalkyl dipeptide compounds
US75269585 1985-07-08
US06/752,695 US4749698A (en) 1985-07-08 1985-07-08 Antihypertensive derivatives

Publications (4)

Publication Number Publication Date
FI853494A0 FI853494A0 (fi) 1985-09-12
FI853494L FI853494L (fi) 1986-03-13
FI89716B true FI89716B (fi) 1993-07-30
FI89716C FI89716C (sv) 1993-11-10

Family

ID=27095707

Family Applications (1)

Application Number Title Priority Date Filing Date
FI853494A FI89716C (sv) 1984-09-12 1985-09-12 Förfarande för framställning av terapeutiskt aktiva prolinderivat

Country Status (13)

Country Link
EP (1) EP0175266B1 (sv)
KR (1) KR860002464A (sv)
AT (1) ATE135711T1 (sv)
AU (1) AU578489B2 (sv)
CA (1) CA1288893C (sv)
DE (1) DE3588094T2 (sv)
DK (1) DK412985A (sv)
ES (1) ES8609364A1 (sv)
FI (1) FI89716C (sv)
IL (1) IL76345A (sv)
IN (1) IN164615B (sv)
NO (1) NO169442C (sv)
NZ (1) NZ213432A (sv)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5629345A (en) * 1993-07-23 1997-05-13 Vide Pharmaceuticals Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
US5965620A (en) * 1993-07-23 1999-10-12 Vide Pharmaceuticals Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
EP0765341A4 (en) * 1994-06-16 1998-09-16 Smithkline Beecham Corp CYCLISATION DIRECTED BY MATRIX
WO2001026644A2 (en) † 1999-10-14 2001-04-19 Curis, Inc. Mediators of hedgehog signaling pathways, compositions and uses related thereto
DE50015940D1 (de) 2000-09-21 2010-07-29 Abb Schweiz Ag Konfiguration eines Leitsystems einer elektrischen Schaltanlage
BRPI0620436B8 (pt) 2005-12-23 2021-05-25 Wyeth Corp compostos miméticos de lisina modificados, composição farmacêutica e uso
DK2468724T3 (en) * 2006-12-21 2016-02-22 Zealand Pharma As Synthesis of pyrrolidine compounds
ES2870106T3 (es) 2017-05-05 2021-10-26 Zealand Pharma As Moduladores de la comunicación intercelular de uniones comunicantes y su uso para el tratamiento de la enfermedad del ojo diabético

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5683483A (en) * 1979-12-13 1981-07-08 Santen Pharmaceut Co Ltd Thiazolidine compound
US4350704A (en) * 1980-10-06 1982-09-21 Warner-Lambert Company Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids
GR75019B (sv) * 1980-09-17 1984-07-12 Univ Miami
US4462943A (en) * 1980-11-24 1984-07-31 E. R. Squibb & Sons, Inc. Carboxyalkyl amino acid derivatives of various substituted prolines
FR2501399B1 (fr) * 1981-03-03 1987-06-19 France Etat Dispositif d'affichage de messages graphiques transmis par des systemes de videotex
EP0080822A1 (en) * 1981-11-27 1983-06-08 Beecham Group Plc Anti-hypertensive prolinol-based peptides
DE3360065D1 (en) * 1982-03-08 1985-03-28 Schering Corp Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them
ZA832762B (en) * 1982-04-30 1983-12-28 Squibb & Sons Inc Substituted 4-phenoxy prolines
AU1643283A (en) * 1982-07-19 1984-01-26 E.R. Squibb & Sons, Inc. Substituted peptides
US4623729A (en) * 1982-07-22 1986-11-18 E. R. Squibb & Sons, Inc. Acylalkylaminocarbonyl substituted amino and imino acid compounds
US4499079A (en) * 1982-11-18 1985-02-12 E. R. Squibb & Sons, Inc. Carboxy and substituted carboxy alkanoyl and cycloalkanoyl peptides
DK156484A (da) * 1983-03-16 1984-09-17 Usv Pharma Corp Aminosyrederivater
EP0127124A3 (en) * 1983-05-23 1987-04-08 Usv Pharmaceutical Corporation Compounds for treating hypertension

Also Published As

Publication number Publication date
NO169442C (no) 1992-06-24
ES546866A0 (es) 1986-07-16
EP0175266B1 (en) 1996-03-20
DK412985D0 (da) 1985-09-11
IN164615B (sv) 1989-04-22
IL76345A0 (en) 1986-01-31
AU578489B2 (en) 1988-10-27
IL76345A (en) 1988-12-30
EP0175266A2 (en) 1986-03-26
FI853494A0 (fi) 1985-09-12
DE3588094T2 (de) 1996-08-22
DK412985A (da) 1986-03-13
NO853551L (no) 1986-03-13
ES8609364A1 (es) 1986-07-16
CA1288893C (en) 1991-09-10
KR860002464A (ko) 1986-04-26
EP0175266A3 (en) 1988-08-03
ATE135711T1 (de) 1996-04-15
FI853494L (fi) 1986-03-13
AU4733185A (en) 1986-03-20
NZ213432A (en) 1988-11-29
NO169442B (no) 1992-03-16
DE3588094D1 (de) 1996-04-25
FI89716C (sv) 1993-11-10

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Legal Events

Date Code Title Description
FG Patent granted

Owner name: RHONE-POULENC RORER PHARMACEUTICALS,INC.

BB Publication of examined application
TC Name/ company changed in patent

Owner name: RHONE-POULENC RORER PHARMACEUTICALS,INC.

MM Patent lapsed
MM Patent lapsed

Owner name: RHONE-POULENC RORER PHARMACEUTICALS,_INC.