DK2875043T3 - Glucagonanaloger - Google Patents

Glucagonanaloger Download PDF

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DK2875043T3
DK2875043T3 DK13756832.5T DK13756832T DK2875043T3 DK 2875043 T3 DK2875043 T3 DK 2875043T3 DK 13756832 T DK13756832 T DK 13756832T DK 2875043 T3 DK2875043 T3 DK 2875043T3
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aib
glu
ser
seq
compound
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Lise Giehm
Ditte Riber
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Zealand Pharma As
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/605—Glucagons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/26—Glucagons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Diabetes (AREA)
  • Gastroenterology & Hepatology (AREA)
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Claims (15)

1. Forbindelse med formel I:
(I) eller et farmaceutisk acceptabelt salt eller solvat deraf; hvor R1 er hydrogen, C-m alkyl, acetyl, formyl, benzoyl eller trifluoracetyl; R2 er OH eller NH2; og Z er en aminosyresekvens afledt af sekvensen med formel la: His-Ser-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Tyr-Ser-Lys-Tyr-Leu- Asp-Ser-Arg-Arg-Ala-Glri-Asp-Phe-Val-Gln-Trp-Leu-Glu-Asn-Thr (la) og yderligere omfattende mindst fire aminosyresubstitutioner eller -deletioner, der kun er på sekvenspositioner udvalgt blandt 2, 3, 4, 9, 10, 15, 16, 17, 20, 21,24, 28 og 29, som følger: X2 er udvalgt blandt Aib og Ala; X3 er udvalgt blandt His, Pro, Dab(Ac), Dap(Ac) og Gln(Me); X4 er DAIa; X9 er Glu; X10 er udvalgt blandt Val, Leu, N-Me-Tyr og N-Me-DTyr; X15 er Glu; X16 er udvalgt blandt Aib, Lys, Glu, Leu, Val, DVal, Phe, His, Arg, Pro, DPro, N-Me-Ser og N-Me-DSer; X17 er udvalgt blandt Ala og Ser; X20 er udvalgt blandt Glu og Lys; X21 er udvalgt blandt Glu, Lys og Ser; X24 er udvalgt blandt Lys, Ser, Glu og Ala; X28 er udvalgt blandt Ser og Lys og Glu eller er fraværende; X29 er udvalgt blandt Ser og Ala eller er fraværende; forudsat, at Z ikke er udvalgt blandt: HSQGTFTSDYSKYLDSARAEDFVKWLEST; og HSQGTFTSDYSKYLESRRAKEFVEWLEST; hvor forbindelsen har glucagonagonistaktivitet og forbedret opløselighed og/eller stabilitet sammenlignet med nativt humant glucagon.
2. Forbindelse ifølge krav 1 med formel I:
(I) eller et farmaceutisk acceptabelt salt eller solvat deraf; hvor R1 er hydrogen, C1-4 alkyl, acetyl, formyl, benzoyl eller trifluoracetyl; R2 er OH eller NH2; og Z er en aminosyresekvens afledt af sekvensen med formel la: His-Scr-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Tyr-Scr-Lys-Tyr-Leu- Asp-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Val-Gln-Trp-Leu-Glu-Asn-Thr (la) og yderligere omfattende mindst fire aminosyresubstitutioner eller -deletioner, der kun er på sekvenspositioner (angivet som X) udvalgt blandt 2, 3, 9, 10, 15,16,17, 20, 21,24, 28 og 29, som følger: X2 er udvalgt blandt Aib og Ala; X3 er udvalgt blandt His og Pro; X9 er Glu; X10 er udvalgt blandt N-Me-Tyr og N-Me-DTyr; X15 er Glu; X16 er udvalgt blandt Aib, Lys, Glu, Leu, Val, DVal, Phe, His, Arg, Pro, DPro, N-Me-Ser og N-Me-DSer; X17 er udvalgt blandt Ala og Ser; X20 er udvalgt blandt Glu og Lys; X21 er udvalgt blandt Glu, Lys og Ser; X24 er udvalgt blandt Lys, Ser, Glu og Ala; X28 er udvalgt blandt Ser og Lys eller er fraværende; X29 er udvalgt blandt Ser og Ala eller er fraværende; forudsat, at Z ikke er udvalgt blandt: HSQGTFTSDYSKYLDSARAEDFVKWLEST; og HSQGTFTSDYSKYLESRRAKEFVEWLEST; hvor forbindelsen har glucagonagonistaktivitet og forbedret opløselighed og/eller stabilitet sammenlignet med nativt humant glucagon.
3. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 1, hvor mindst fire aminosyresubstitutioner eller -deletioner på aminosyrese- kvenspositioner (angivet som X) udvalgt blandt 2, 3, 4, 9, 10, 15, 16, 17, 20, 21,24, 28 og 29 af forbindelsen med formel I er som følger: X2 er udvalgt blandt Aib og Ala; X3 er udvalgt blandt His og Pro; X4 er DAIa; X9 er Glu; X10 er udvalgt blandt N-Me-Tyr og N-Me-DTyr; X15 er Glu; X16 er udvalgt blandt Aib, Lys, Glu, Leu, Val, Phe, His og Arg; X17 er udvalgt blandt Ala og Ser; X20 er udvalgt blandt Glu og Lys; X21 er udvalgt blandt Glu, Lys og Ser; X24 er udvalgt blandt Lys, Ser, Glu og Ala; X28 er udvalgt blandt Ser, Glu og Lyseller er fraværende; X29 er udvalgt blandt Ser og Ala eller er fraværende.
4. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 1, hvor de mindst fire aminosyresubstitutioner eller -deletioner er på aminosy-resekvenspositioner (angivet ved et X) udvalgt blandt 2, 3, 4, 10, 15, 16, 17, 20, 21,24, 28 og 29 af forbindelsen med formel I og er som følger: X2 er Ala; X3 er Dab(Ac), Dap(Ac) og Gln(Me); X4 er DAIa; X10 er udvalgt blandt Leu og Val; X15 er Glu; X16 er udvalgt blandt Aib, Lys, Glu, Leu og Val; X17 er Ala; X20 er udvalgt blandt Glu og Lys; X21 er udvalgt blandt Glu og Ser; X24 er udvalgt blandt Lys, Ser og Glu; X28 er udvalgt blandt Ser, Glu og Lys; X29 er Ala eller er fraværende.
5. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 1, hvor de mindst fire aminosyresubstitutioner eller -deletioner er på aminosy- resekvenspositioner (angivet ved et X) udvalgt blandt 2, 3, 4, 16, 17, 20, 21, 24, 28 og 29 af forbindelsen med formel I og er som følger: X2 er Ala; X3 er Dab(Ac), Dap(Ac), Gln(Me) eller His; X4 er DAIa; X16 er udvalgt blandt Aib, Lys, Glu; X17 er Ala; X20 er udvalgt blandt Glu og Lys; X21 er udvalgt blandt Glu og Ser; X24 er udvalgt blandt Lys, Ser og Glu; X28 er udvalgt blandt Ser, Glu og Lys; X29 er Ala eller er fraværende.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor X17 er Ala.
7. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf ifølge et hvilket som helst af kravene 1 til 5, hvor Z er udvalgt fra gruppen bestående af: HSQGTFTSDYSKYLDSARAESFVKWLEST (SEQ ID NO: 2) HSQGTFTSDYSKYLDSARAEDFVKWLEET (SEQ ID NO: 3) HSQGTFTSDYSKYLDKARAEDFVKWLEST (SEQ ID NO: 4) HSQGTFTSDYSKYLDSARAEDFVAWLEST (SEQ ID NO: 5) HSQGTFTSDYSKYLDEARAKDFVEWLEKT (SEQ ID NO: 6) HSQGTFTSDYSKYLDSARAEDFVEWLEST (SEQ ID NO: 7) HSQGTFTSDYSKYLESARAEDFVKWLEST (SEQ ID NO: 9) HSQGTFTSDYSKYLDSARAEEFVKWLEST (SEQ ID NO: 10) HSQGTFTSDYSKYLDSARAEDFVSWLEST (SEQ ID NO: 11) HSQGTFTSDLSKYLDSARAEDFVKWLEST (SEQ ID NO: 12) HSQGTFTSDYSKYLD-Aib-ARAEDFVKWLEST (SEQ ID NO: 13) HSQGTFTSDYSKYLDSARAEDFVKWLES (SEQ ID NO: 14) HSQGTFTSDYSKYLDEARAEDFVKWLEST (SEQ ID NO: 15) HSQGTFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 16) HSQGTFTSDYSKYLESARAESFVKWLEST (SEQ ID NO: 17) HSQGTFTSDYSKYLDLARAEDFVKWLEST (SEQ ID NO: 18) HSQGTFTSDYSKYLDKRRAEDFVSWLEST (SEQ ID NO: 19) HSQGTFTSDYSKYLDVARAESFVKWLEST (SEQ ID NO: 20) HAQGTFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 21) HSQGTFTSDYSKYLD-Aib-ARAEEFVKWLEST (SEQ ID NO: 22) HSQ-DAIa-TFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 23) HSQGTFTSDVSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 24) HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 25) HSQGTFTSDYSKYLD-Aib-RRAESFVKWLEST (SEQ ID NO: 26) HS-[Gln(Me)]-GTFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 27) HSQGTFTSDYSKYLDEARAKSFVEWLEKT (SEQ ID NO: 28) HSQGTFTSDYSKYLDEARAKSFVEWLEST (SEQ ID NO: 29) HSQGTFTSDYSKYLD-Aib-ARAKSFVEWLEKT (SEQ ID NO: 30) HSQGTFTSDYSKYLD-Aib-ARAESFVKWLESA (SEQ ID NO: 31) HSQGTFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 32) HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAESFVKWLEST (SEQ ID NO: 33) HSQGTFTSDYSKYLD-Aib-ARAEEFVSWLEKT (SEQ ID NO: 34) HSQGTFTSDYSKYLD-Aib-ARAEKFVEWLEST (SEQ ID NO: 35) HSQGTFTSDYSKYLD-Aib-ARAEEFVAWLEST (SEQ ID NO: 36) HSQGTFTSDYSKYLD-Aib-ARAEEFVKWLEET (SEQ ID NO: 37) HSQGTFTSDYSKYLE-Aib-ARAEEFVKWLEST (SEQ ID NO: 38) HSHGTFTSDYSKYLD-Aib-ARAEEFVKWLEST (SEQ ID NO: 39) HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAEEFVKWLEST (SEQ ID NO: 40) °9 HS-[Dap(Ac)]-GTFTSDYSKYLD-Aib-ARAEEFVKWLEST (SEQ ID NO: 41).
8. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, udvalgt fra gruppen bestående af: Hy-HSQGTFTSDYSKYLDSARAESFVKWLEST-OH Hy-HSQGTFTSDYSKYLDSARAEDFVKWLEET-OH Hy-HSQGTFTSDYSKYLDKARAEDFVKWLEST-OH Hy-HSQGTFTSDYSKYLDSARAEDFVAWLEST-OH Hy-HSQGTFTSDYSKYLDEARAKDFVEWLEKT-OH Hy-HSQGTFTSDYSKYLDSARAEDFVEWLEST-OH Hy-HSQGTFTSDYSKYLESARAEDFVKWLEST-OH Hy-HSQGTFTSDYSKYLDSARAEEFVKWLEST-OH Hy-HSQGTFTSDYSKYLDSARAEDFVSWLEST-OH Hy-HSQGTFTSDLSKYLDSARAEDFVKWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAEDFVKWLEST-OH Hy-HSQGTFTSDYSKYLDSARAEDFVKWLES-OH Hy-HSQGTFTSDYSKYLDEARAEDFVKWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAESFVKWLEST-OH Hy-HSQGTFTSDYSKYLESARAESFVKWLEST-OH Hy-HSQGTFTSDYSKYLDLARAEDFVKWLEST-OH Hy-HSQGTFTSDYSKYLDKRRAEDFVSWLEST-OH Hy-HSQGTFTSDYSKYLDVARAESFVKWLEST-OH Hy-HAQGTFTSDYSKYLD-Aib-ARAESFVKWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAEEFVKWLEST-OH Hy-HSQ-DAIa-TFTSDYSKYLD-Aib-ARAESFVKWLEST-OH Hy-HSQGTFTSDVSKYLD-Aib-ARAESFVKWLEST-OH Hy-HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAESFVKWLEST-NH2 Hy-HSQGTFTSDYSKYLD-Aib-RRAESFVKWLEST-OH Hy-HS-[Gln(Me)]-GTFTSDYSKYLD-Aib-ARAESFVKWLEST-OH Hy-HSQGTFTSDYSKYLDEARAKSFVEWLEKT-OH Hy-HSQGTFTSDYSKYLDEARAKSFVEWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAKSFVEWLEKT-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAESFVKWLESA-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAESFVKWLEST-NH2 Hy-HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAESFVKWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAEEFVSWLEKT-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAEKFVEWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAEEFVAWLEST-OH Hy-HSQGTFTSDYSKYLD-Aib-ARAEEFVKWLEET-OH Hy-HSQGTFTSDYSKYLE-Aib-ARAEEFVKWLEST-OH Hy-HSHGTFTSDYSKYLD-Aib-ARAEEFVKWLEST-NH2 Hy-HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAEEFVKWLEST-OH Hy-HS-[Dab(Ac)]-GTFTSDYSKYLD-Aib-ARAEEFVKWLEST-NH2 Hy-HS-[Dap(Ac)]-GTFTSDYSKYLD-Aib-ARAEEFVKWLEST-NH2 eller et farmaceutisk acceptabelt salt eller solvat deraf.
9. Nukleinsyrekonstrukt, der koder for et peptid Z ifølge et hvilket som helst af kravene 1 til 7, hvor peptidet udelukkende består af naturligt forekommende aminosyrer.
10. Ekspressionsvektor omfattende et nukleinsyrekonstrukt ifølge krav 9.
11. Værtscelle omfattende et nukleinsyrekonstrukt ifølge krav 9 eller en ekspressionsvektor ifølge krav 10.
12. Farmaceutisk sammensætning omfattende en forbindelse eller et farmaceutisk acceptabelt salt eller solvat deraf ifølge et hvilket som helst af kravene 1 -8 og en farmaceutisk acceptabel bærer.
13. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf ifølge et hvilket som helst af kravene 1-8 til anvendelse i en fremgangsmåde til medicinsk behandling.
14. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf ifølge et hvilket som helst af kravene 1-8 til anvendelse i en fremgangsmåde til behandling af hypoglykæmi, akut hypoglykæmi, kronisk hypoglykæmi, type 2-diabetes, nedsat glukosetolerance, type 1-diabetes, adipositas, koronar hjertesygdom, aterosklerose, hypertension, dyslipidæmi, hepatisk steatose, β-blokker-forgiftning, insulinom og Von Gierkes sygdom.
15. Forbindelse eller farmaceutisk acceptabelt salt eller solvat deraf til anvendelse ifølge krav 14, hvor hypoglykæmien er udvalgt fra gruppen bestående af: diabetisk hypoglykæmi, akut insulininduceret hypoglykæmi, non-diabetisk hypoglykæmi, reaktiv hypoglykæmi, fastende hypoglykæmi, lægemiddelinduceret hypoglykæmi, alkoholinduceret hypoglykæmi, gastrisk by-pass-induceret hypoglykæmi og hypoglykæmi, der forekommer under graviditet.
DK13756832.5T 2012-07-23 2013-07-23 Glucagonanaloger DK2875043T3 (da)

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US201261674706P 2012-07-23 2012-07-23
US201361785611P 2013-03-14 2013-03-14
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PCT/EP2013/065519 WO2014016300A1 (en) 2012-07-23 2013-07-23 Glucagon analogues

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