DK2415763T3 - Farmaceutisk sammensætning til behandling eller forebyggelse af glaukom - Google Patents

Farmaceutisk sammensætning til behandling eller forebyggelse af glaukom Download PDF

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DK2415763T3
DK2415763T3 DK10758728.9T DK10758728T DK2415763T3 DK 2415763 T3 DK2415763 T3 DK 2415763T3 DK 10758728 T DK10758728 T DK 10758728T DK 2415763 T3 DK2415763 T3 DK 2415763T3
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phenyl
pyridin
thiophen
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Masahiko Hagihara
Kenji Yoneda
Eiji Okanari
Manabu Shigetomi
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Ube Industries
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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
    • C07D213/60—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
    • C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Claims (18)

1. Medicinsk oftalmisk opløsning til anvendelse i behandlingen eller profylakse af glaukom der omfatter pyridylaminoeddikesyreforbindelse som vist med formlen (1):
(1) formel 1 hvor R1, R2 og R3 hver uafhængigt betegner et hydrogenatom eller en C1-C6 alkylgruppe, Y betegner en bicyklisk heteroaromatisk ringgruppe eller gruppe -Q1-Q2 der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, Ci-Ce alkylgruppe, halogeno Ci-Ce alkylgruppe, Ci-Ce alkoxylgruppe, halogeno Ci-Ce alkoxylgruppe og Ci-Ce alkylthiogruppe, hvor Q1 betegner en arylengruppe eller en 5- til 6-leddet heteroarylengruppe, Q2 betegner en aromatisk gruppe eller 5- til 6-leddet ring heterocyklisk gruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, hydroxylgruppe, C1-C6 alkylgruppe, halogeno C1-C6 alkylgruppe, Ci-Ce alkoxylgruppe og halogen C1-C6 alkoxylgruppe, Z betegner en aromatisk gruppe eller en 5- til 6-leddet heteroaromatisk ringgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, C1-C6 alkylgruppe, halogeno Ci-Ce alkylgruppe, Ci-Ce alkoxylgruppe og halogeno C1-C6 alkoxylgruppe, eller et farmaceutisk acceptabelt salt deraf som en effektiv bestanddel, og hvor opløsningen dryppes i øjet.
2. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1, hvor R2 og R3 hver uafhængigt betegner et hydrogenatom eller en C1-C4 alkylgruppe.
3. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1 eller 2, hvor Y betegner en bicyklisk heteroaromatisk ringgruppe eller en gruppe -Q^Q2 der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, C1-C4 alkylgruppe, halogeno C1-C4 alkylgruppe, C1-C4 alkoxylgruppe, halogeno C1-C4 alkoxylgruppe og C1-C4 alkylthiogruppe, hvor Q1 betegner en arylengruppe eller en 5- til 6-leddet heteroarylengruppe, Q2 betegner en aromatisk gruppe eller en 5- til 6-leddet ring heterocyklisk gruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, hydroxylgruppe, C1-C4 alkylgruppe, halogeno C1-C4 alkylgruppe, C1-C4 alkoxylgruppe og halogeno C1-C4 alkoxylgruppe.
4. Medicinsk oftalmisk opløsning til anvendelse ifølge et hvilket som helst af kravene 1 til 3, hvor Z betegner en aromatisk gruppe eller en fuldstændig umættet 5- til 6-leddet heteroaromatisk ringgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, C1-C4 alkylgruppe, halogeno C1-C4 alkylgruppe, C1-C4 alkoxylgruppe og halogeno C1-C4 alkoxylgruppe.
5. Medicinsk oftalmisk opløsning til anvendelse ifølge et hvilket som helst af kravene 1 til 4, hvorY betegner en benzofurylgruppe, benzothienylgruppe, benzoxazolylgruppe eller benzothiazolylgruppe, eller en gruppe -Q^Q2 der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, C1-C4 alkylgruppe, halogeno C1-C4 alkylgruppe, C1-C4 alkoxylgruppe, halogeno C1-C4 alkoxylgruppe og C1-C4 alkylthiogruppe, hvor Q1 betegner en phenylengruppe, thienylengruppe, pyridazinylengruppe eller pyrimidinylengruppe, Q2 betegner en phenylgruppe, thienylgruppe, pyrazolylgruppe, oxazolylgruppe, thiazolylgruppe, 1,2,4-triazolylgruppe, pyridylgruppe, pyridazinylgruppe, pyrimidinylgruppe, 4,5-dihydrothiazolylgruppe, pyrrolidinylgruppe eller piperidinylgruppe der kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, hydroxylgruppe, C1-C4 alkylgruppe, halogeno C1-C4 alkylgruppe, C1-C4 alkoxylgruppe og halogeno C1-C4 alkoxylgruppe.
6. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 5, hvorY betegner en benzofurylgruppe, benzothienylgruppe, benzoxazolylgruppe eller benzothiazolylgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et fluoratom, chloratom, bromatom, methylgruppe, ethylgruppe, propylgruppe, isopropylgruppe, tert-butylgruppe, trifluormethylgruppe, difluormethylgruppe, trichlormethylgruppe, dichlormethylgruppe, 2,2,2-trifluorethylgruppe, 2,2,2-trichlorethylgruppe, methoxygruppe, ethoxygruppe, propoxygruppe, isopropoxygruppe, tert- butoxygruppe, trifluormethoxygruppe, difluormethoxygruppe, trichlormethoxygruppe, dichlormethoxygruppe, methylthiogruppe, ethylthiogruppe, propylthiogruppe, isopropylthiogruppe og tert-butylthiogruppe.
7. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 5, hvor Y er en gruppe -Q1-Q2 hvor Q1 betegner en phenylengruppe, thienylengruppe, pyridazinylengruppe eller pyrimidinylengruppe, Q2 betegner en phenylgruppe, thienylgruppe, pyrazolylgruppe, oxazolylgruppe, thiazolylgruppe, 1,2,4-triazolylgruppe, pyridylgruppe, pyridazinylgruppe, pyrimidinylgruppe, 4,5-dihydrothiazolylgruppe, pyrrolidinylgruppe eller piperidinylgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et fluoratom, chloratom, bromatom, hydroxylgruppe, methylgruppe, ethylgruppe, propylgruppe, isopropylgruppe, tert-butylgruppe, trifluormethylgruppe, difluormethylgruppe, trichlormethylgruppe, dichlormethylgruppe, 2,2,2-trifluorethylgruppe, 2,2,2-trichlorethylgruppe, methoxygruppe, ethoxygruppe, propoxygruppe, isopropoxygruppe, tert-butoxygruppe, trifluormethoxygruppe, difluormethoxygruppe, trichlormethoxygruppe og dichlormethoxygruppe.
8. Medicinsk oftalmisk opløsning til anvendelse ifølge et hvilket som helst af kravene 1 til 7, hvor Z betegner en phenylgruppe, thienylgruppe, imidazolylgruppe, thiazolylgruppe, pyridylgruppe eller pyrimidinylgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, C1-C4 alkylgruppe, halogeno C1-C4 alkylgruppe, C1-C4 alkoxylgruppe og halogeno C1-C4 alkoxylgruppe.
9. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 8, hvor Z betegner en phenylgruppe, thienylgruppe, imidazolylgruppe, thiazolylgruppe, pyridylgruppe eller pyrimidinylgruppe, der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et fluoratom, chloratom, bromatom, methylgruppe, ethylgruppe, propylgruppe, isopropylgruppe, tert-butylgruppe, trifluormethylgruppe, difluormethylgruppe, trichlormethylgruppe, dichlormethylgruppe, 2,2,2-trifluorethylgruppe, 2,2,2-trichlorethylgruppe, methoxygruppe, ethoxygruppe, propoxygruppe, isopropoxygruppe, tert-butoxygruppe, trifluormethoxygruppe, difluormethoxygruppe, trichlormethoxygruppe og dichlormethoxygruppe.
10. Medicinsk oftalmisk opløsning til anvendelse ifølge et hvilket som helst af kravene 1 til 9, hvor R2 og R3 hver uafhængigt betegner et hydrogenatom eller en methylgruppe.
11. Medicinsk oftalmisk opløsning ifølge et hvilket som helst af kravene 1 til 5 og 8 til 10, hvor Y betegner en benzofurylgruppe eller benzothienylgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom og en C1-C4 alkoxylgruppe.
12. Medicinsk oftalmisk opløsning til anvendelse ifølge et hvilket som helst af kravene 1 til 5 og 8 til 10, hvor Y betegner en gruppe -Q^Q2 hvor Q1 betegner en phenylengruppe eller pyridazinylengruppe, Q2 betegner en phenylgruppe, pyrazolylgruppe, thiazolylgruppe, 1,2,4-triazolylgruppe, pyridylgruppe, pyridazinylgruppe, pyrimidinylgruppe eller 4,5-dihydrothiazolylgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom, C1-C4 alkylgruppe og halogeno C1-C4 alkylgruppe.
13. Medicinsk oftalmisk opløsning til anvendelse ifølge et hvilket som helst af kravene 1 til 5 og 8 til 10, hvor Z betegner en phenylgruppe eller pyridylgruppe der hver kan være substitueret med en gruppe(r) valgt fra gruppen bestående af et halogenatom og en C1-C4 alkoxylgruppe.
14. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1, hvor R1 betegner en hydrogenatom, methylgruppe, ethylgruppe, propylgruppe, isopropylgruppe, butylgruppe, isobutylgruppe, sec-butylgruppe, tert-butylgruppe, pentylgruppe eller hexylgruppe, R2 og R3 hver uafhængigt betegner et hydrogenatom eller methylgruppe, Y betegner en benzofuran-2-ylgruppe, 6-fluorbenzofuran-2-ylgruppe, 6-chlorbenzofuran-2-ylgruppe, 6-methoxybenzofuran-2-ylgruppe, benzo[b]thiophen-2-ylgruppe, 6-fluorbenzo[b]thiophen-2-ylgruppe, 5,6-difluorbenzo[b]thiophen-2-ylgruppe, 6-chlor-benzo[b]thiophen-2-ylgruppe, 6-chlor-5-fluorbenzo[b]thiophen-2-ylgruppe, 6-methyl-benzo[b]thiophen-2- ylgruppe, 5-fluor-6-methylbenzo[b]thiophen-2-ylgruppe, 6-ethyl-benzo[b]thiophen-2-ylgruppe, 6-ethyl-5-fluorbenzo[b]thiophen-2-ylgruppe, 6-trifluor-methylbenzo[b]thiophen-2-ylgruppe, 5-fluor-6-trifluormethylbenzo[b]thiophen-2-ylgruppe, 6-methoxybenzo[b]thiophen-2-ylgruppe, 5-fluor-6-methoxybenzo[b]thiophen-2-ylgruppe, 6-difluormethoxybenzo[b]thiophen-2-ylgruppe, 6-difluormethoxy-5-fluorbenzo[b]thiophen-2-ylgruppe, 6-methylthiobenzo[b]thiophen-2-ylgruppe, 5-fluor-6-methylthiobenzo[b]thiophen-2-ylgruppe, biphenyl-4-ylgruppe, 2'-fluorbiphenyl-4-ylgruppe, 3'-fluorbiphenyl-4-ylgruppe, 4'-fluorbiphenyl-4-ylgruppe, 2',4'-difluorbiphenyl-4-ylgruppe, 3',4'-difluorbiphenyl-4-ylgruppe, 2'-chlorbiphenyl-4-ylgruppe, 3'-chlorbiphenyl-4-ylgruppe, 4'-chlorbiphenyl-4-ylgruppe, 4'-chlor-2'-fluorbiphenyl-4-ylgruppe, 4'-chlor-3'-fluorbiphenyl-4-ylgruppe, 4'-hydroxybiphenyl-4-ylgruppe, 3'-methylbiphenyl-4-ylgruppe, 3'-ethylbiphenyl-4-ylgruppe, 3'-trifluormethylbiphenyl-4-ylgruppe, 3'-methoxybiphenyl-4-ylgruppe, 3'-difluormethoxybiphenyl-4-ylgruppe, 4-(thiophen-2-yl)phenylgruppe, 4-(thiophen-3-yl)phenylgruppe, 4-(pyrazol-l-yl)phenylgruppe, 4-(oxazol-2-yl)phenylgruppe, 4-(oxazol-4-yl)phenylgruppe, 4-(thiazol-2-yl)phenylgruppe, 4-(4-fluorthiazol-2-yl)phenylgruppe, 4-(4-chlorthiazol-2-yl)phenylgruppe, 4-(5-chlorthiazol-2-yl)phenylgruppe, 4-(5-methylthiazol-2-yl)phenylgruppe, 4-(4,5-dimethylthiazol-2-yl)phenylgruppe, 4-(4-trifluormethylthiazol-2-yl)phenylgruppe, 4-(thiazol-4-yl)phenylgruppe, 4-(2-fluorthiazol-4-yl)phenylgruppe, 4-(2-chlorthiazol-4-yl)phenylgruppe, 4-(thiazol-5-yl)phenylgruppe, 4-(l,2,4-triazol-l-yl)phenylgruppe, 4-(pyridin-2-yl)phenylgruppe, 4-(pyridazin-3-yl)phenylgruppe, 4-(pyridazin-4-yl)phenylgruppe, 4-(pyrimidin-2-yl)phenylgruppe, 4-(5-hydroxypyrimidin-2-yl)phenylgruppe, 4-(pyrimidin-4-yl)phenylgruppe, 4-(pyrimidin-5-yl)phenylgruppe, 4-(4,5-dihydrothiazol-2-yl)phenylgruppe, 6-phenylpyridazin-3-ylgruppe, 6-(thiazol-2-yl)pyridazin-3-ylgruppe eller 6-(thiazol-4-yl)pyridazin-3-ylgruppe, og Z betegner en phenylgruppe, 2-fluorphenylgruppe, 3-fluorphenylgruppe, 4-fluorphenylgruppe, 3,4-difluorphenylgruppe, 3,5-difluorphenylgruppe, 3,4,5-trifluorphenylgruppe, 2-chlorphenylgruppe, 3-chlorphenylgruppe, 4-chlorphenylgruppe, 2,6-dichlorphenylgruppe, 4-chlor-3-fluorphenylgruppe, 4-chlor-3,5-difluorphenylgruppe, 4-bromophenylgruppe, 4-methylphenylgruppe, 3-fluor-4-methylphenylgruppe, 4-ethylphenylgruppe, 4-ethyl-3-fluorphenylgruppe, 4-propylphenylgruppe, 4-isopropylphenylgruppe, 4-tert- 6 butylphenylgruppe, 4-trifluormethylphenylgruppe, 3-fluor-4-trifluormethylphenylgruppe, 4-difluormethylphenylgruppe, 4-trichlormethylphenylgruppe, 4-dichlormethylphenylgruppe, 4-(2,2,2-trifluorethyl)phenylgruppe, 4-(2,2,2-trichlorethyl)phenylgruppe, 4-methoxyphenylgruppe, 3-fluor-4-methoxyphenylgruppe, 4-ethoxyphenylgruppe, 4-propoxyphenylgruppe, 4-isopropoxyphenylgruppe, 4-tert-butoxyphenylgruppe, 4-trifluormethoxyphenylgruppe, 4-difluormethoxyphenylgruppe, 4-difluormethoxy-3-fluorphenylgruppe, 4-trichlormethoxyphenylgruppe, 4- dichlormethoxyphenylgruppe, thiophen-2-ylgruppe, thiophen-3-ylgruppe, 5-chlor thiophen-2-ylgruppe, l-methyl-lH-imidazol-4-ylgruppe, thiazol-2-ylgruppe, pyridin-2-ylgruppe, 5-fluorpyridin-2-ylgruppe, 5-chlorpyridin-2-ylgruppe, 5- methylpyridin-2-ylgruppe, 5-ethylpyridin-2-ylgruppe, 5-trifluormethylpyridin-2-ylgruppe, 5-methoxypyridin-2-ylgruppe, 5-difluormethoxypyridin-2-ylgruppe, pyridin-3-ylgruppe, 6-fluorpyridin-3-ylgruppe, 6-chlorpyridin-3-ylgruppe, 6- methylpyridin-3-ylgruppe, 6-ethylpyridin-3-ylgruppe, 6-trifluormethylpyridin-3-ylgruppe, 6-methoxypyridin-3-ylgnippe, 6-difluormethoxypyridin-3-ylgruppe, pyridin-4-ylgruppe eller pyrimidin-2-ylgruppe.
15. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1, hvor R1 betegner en hydrogenatom, methylgruppe, ethylgruppe, propylgruppe, isopropylgruppe, tert-butylgruppe eller hexylgruppe, R2 og R3 hver uafhængigt betegner et hydrogenatom eller methylgruppe, Y betegner en benzofuran-2-ylgruppe, 6-fluorbenzofuran-2-ylgruppe, 6-chlorbenzofuran-2-ylgruppe, 6-methoxybenzofuran-2-ylgruppe, benzo[b]thiophen-2-ylgruppe, 6-fluorbenzo[b]thiophen-2-ylgruppe, 6-chlorbenzo[b]thiophen-2-ylgruppe, 6-methoxy-benzo[b]thiophen-2-ylgruppe, biphenyl-4-ylgruppe, 2'-fluorbiphenyl-4-ylgruppe, 3'-fluorbiphenyl-4-ylgruppe, 4'-fluorbiphenyl-4-ylgruppe, 2'-chlorbiphenyl-4-ylgruppe, 3'-chlorbiphenyl-4-ylgruppe, 4'-chlorbiphenyl-4-ylgruppe, 3'-methylbiphenyl-4-ylgruppe, 3'-trifluormethylbiphenyl-4-ylgruppe, 4-(thiophen-2-yl)phenylgruppe, 4-(thiophen-3-yl)phenylgruppe; 4-(pyrazol-l-yl)phenylgruppe, 4-(oxazol-2-yl)phenylgruppe, 4-(oxazol-4-yl)phenylgruppe, 4-(thiazol-2-yl)phenylgruppe, 4-(4-fluorthiazol-2-yl)phenylgruppe, 4-(4-chlorthiazol-2-yl)phenylgruppe, 4-(5-chlorthiazol-2-yl)phenylgruppe, 4-(5-methylthiazol-2-yl)phenylgruppe, 4-(4,5-dimethylthiazol-2- 7 yl)phenylgruppe, 4-(4-trifluormethylthiazol-2-yl)phenylgruppe, 4-(thiazol-4-yl)phenylgruppe, 4-(2-fluorthiazol-4-yl)phenylgruppe, 4-(2-chlorthiazol-4-yl)phenylgruppe, 4-(thiazol-5-yl)phenylgruppe, 4-(l,2,4-triazol-l-yl)phenylgruppe, 4-(pyridin-2-yl)phenylgruppe, 4-(pyridazin-3-yl)phenylgruppe, 4-(pyridazin-4-yl)phenylgruppe, 4-(pyrimidin-2-yl)phenylgruppe, 4-(pyrimidin-4-yl)phenylgruppe, 4-(pyrimidin-5-yl)phenylgruppe, 4-(4,5-dihydrothiazol-2-yl)phenylgruppe eller 6-phenylpyridazin-3-ylgruppe, og Z betegner en phenylgruppe, 2-fluorphenylgruppe, 3-fluorphenylgruppe, 4-fluorphenylgruppe, 3,4-difluorphenylgruppe, 3,5-difluorphenylgruppe, 2- chlorphenylgruppe, 3-chlorphenylgruppe, 4-chlorphenylgruppe, 2,6-dichlorphenylgruppe, 4-chlor-3-fluorphenylgruppe, 4-methylphenylgruppe, 3- fluor-4-methylphenylgruppe, 4-ethylphenylgruppe, 4-ethyl-3-fluorphenylgruppe, 4-trifluormethylphenylgruppe, 3-fluor-4-trifluormethylphenylgruppe, 4- methoxyphenylgruppe, 3-fluor-4-methoxyphenylgruppe, 4- difluormethoxyphenylgruppe, 4-difluormethoxy-3-fluorphenylgruppe, thiophen- 2-ylgruppe, thiophen-3-ylgruppe, pyridin-2-ylgruppe, 5-fluorpyridin-2-ylgruppe, 5- chlorpyridin-2-ylgruppe, 5-methoxypyridin-2-ylgruppe, pyridin-3-ylgruppe, 6-fluorpyridin-3-ylgruppe, 6-chlorpyridin-3-ylgruppe, 6-methoxypyridin-3-ylgruppe eller pyridin-4-ylgruppe.
16. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1, hvor R1 betegner en hydrogenatom, methylgruppe, ethylgruppe, isopropylgruppe eller hexylgruppe, R2 og R3 hver betegner et hydrogenatom, Y betegner en benzofuran-2-ylgruppe, 6-fluorbenzofuran-2-ylgruppe, 6- chlorbenzofuran-2-ylgruppe, 6-methoxybenzofuran-2-ylgruppe, benzo[b]thiophen-2-ylgruppe, 6-fluorbenzo[b]thiophen-2-ylgruppe, 6-chlorbenzo[b]thiophen-2-ylgruppe, 6-methoxy-benzo[b]thiophen-2-ylgruppe, biphenyl-4-ylgruppe, 2'-fluorbiphenyl-4-ylgruppe, 3'-fluorbiphenyl-4-ylgruppe, 4'-fluorbiphenyl-4-ylgruppe, 2'-chlorbiphenyl-4-ylgruppe, 3'-chlorbiphenyl-4-ylgruppe, 4'-chlorbiphenyl-4-ylgruppe, 3'-methylbiphenyl-4-ylgruppe, 3'-trifluormethylbiphenyl-4-ylgruppe, 4-(thiophen-2-yl)phenylgruppe, 4-(thiophen-3-yl)phenylgruppe, 4-(pyrazol-l-yl)phenylgruppe, 4-(oxazol-2-yl)phenylgruppe, 4-(oxazol-4-yl)phenylgruppe, 4-(thiazol-2-yl)phenylgruppe, 4-(4-fluorthiazol-2- yl)phenylgruppe, 4-(4-chlorthiazol-2-yl)phenylgruppe, 4-(5-chlorthiazol-2-yl)phenylgruppe, 4-(5-methylthiazol-2-yl)phenylgruppe, 4-(4,5-dimethylthiazol-2-yl)phenylgruppe, 4-(4-trifluormethylthiazol-2-yl)phenylgruppe, 4-(thiazol-4-yl)phenylgruppe, 4-(2-fluorthiazol-4-yl)phenylgruppe, 4-(2-chlorthiazol-4-yl)phenylgruppe, 4-(thiazol-5-yl)phenylgruppe, 4-(l,2,4-triazol-l-yl)phenylgruppe, 4-(pyridin-2-yl)phenylgruppe, 4-(pyridazin-3-yl)phenylgruppe, 4-(pyridazin-4-yl)phenylgruppe, 4-(pyrimidin-2-yl)phenylgruppe, 4-(pyrimidin-4-yl)phenylgruppe, 4-(pyrimidin-5-yl)phenylgruppe, 4-(4,5-dihydiothiazol-2-yl)phenylgruppe eller 6-phenylpyridazin-3-ylgruppe, og Z betegner en phenylgruppe, 2-fluorphenylgruppe, 3-fluorphenylgruppe, 4-fluorphenylgruppe, 2-chlorphenylgruppe, 3-chlorphenylgruppe, 4-chlorphenylgruppe, 2,6-dichlorphenylgruppe, 4-methoxyphenylgruppe, pyridin-2-ylgruppe eller pyridin-3-ylgruppe.
17. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1, hvor R1 betegner en hydrogenatom, methylgruppe, ethylgruppe, isopropylgruppe eller hexylgruppe, R2 og R3 hver betegner et hydrogenatom, Y betegner en benzofuran-2-ylgruppe, benzo[b]thiophen-2-ylgruppe, 6-chlorbenzo[b]thiophen-2-ylgruppe, 6-methoxybenzo[b]thiophen-2-ylgruppe, biphenyl-4-ylgruppe, 4'-fluorbiphenyl-4-ylgruppe, 4'-chlorbiphenyl-4-ylgruppe, 4-(pyrazol-l-yl)phenylgruppe, 4-(thiazol-2-yl)phenylgruppe, 4-(5-chlorthiazol-2-yl)phenylgruppe, 4-(5-methylthiazol-2-yl)phenylgruppe, 4-(4,5-dimethylthiazol-2-yl)phenylgruppe, 4-(4-trifluormethylthiazol-2-yl)phenylgruppe, 4-(thiazol-4-yl)phenylgruppe, 4-(l,2,4-triazol-l-yl)phenylgruppe, 4-(pyridin-2-yl)phenylgruppe, 4-(pyridazin-4-yl)phenylgruppe, 4-(pyrimidin-2-yl)phenylgruppe, 4-(4,5-dihydrothiazol-2-yl)phenylgruppe eller 6-phenylpyridazin- 3- ylgruppe, og Z betegner en phenylgruppe, 2-fluorphenylgruppe, 3-fluorphenylgruppe, 4- fluorphenylgruppe, 2-chlorphenylgruppe, 3-chlorphenylgruppe, 4-chlorphenylgruppe, 2,6-dichlorphenylgruppe, 4-methoxyphenylgruppe, pyridin-2-ylgruppe eller pyridin-3-ylgruppe.
18. Medicinsk oftalmisk opløsning til anvendelse ifølge krav 1, hvor pyridylaminoeddikesyreforbindelsen er {6-[(benzofuran-2-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2- ylamino}eddikesyre, {6-[(benzo[b]thiophen-2-ylmethyl)(pyridin-3- ylsulfonyl)aminomethyl]pyridin-2-yl-amino>eddikesyre, {6-[(6-chlorbenzo[b]thiophen-2-ylmethyl)(pyridin-3- ylsulfonyl)aminomethyl]pyndin-2-ylamino}eddikesyre, {6-[(6-methoxybenzo[b]thiophen-2-ylmethyl)(pyridin-3- ylsulfonyl)aminomethyl]pyridin-2-ylamino}eddikesyre, {6-[(biphenyl-4-ylmethyl)(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2- ylamino>eddikesyre, {6-[(biphenyl-4-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2- ylamino}eddikesyre, {6-[(4'-fluorbiphenyl-4-ylmethyl)(pyridin-3- ylsulfonyl)aminomethyl]pyridin-2-yl-amino>eddikesyre, {6-[(4'-chlorbiphenyl-4-ylmethyl)(pyridin-3- ylsulfonyl)aminomethyl]pyridin-2-yl-amino}eddikesyre, (6-{(4-fluorbenzenesulfonyl)[4-(pyrazol-l-yl)benzyl]aminomethyl}pyridin- 2-ylamino)eddikesyre, (6-{[4-(pyrazol-l-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyndin-2- ylamino)eddikesyre, (6-{[4-(pyrazol-l-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2- ylamino)eddikesyre, isopropyl (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl>pyridin-2-ylamino)acetat, ethyl (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl-amino)acetat, (6-{(4-fluorbenzenesulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin- 2-ylamino)eddikesyre, (6-{(pyndin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl>pyridin-2- ylamino)eddikesyre, (6-{(pyridin-3-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin-2- ylamino)eddikesyre, (6-{(pyridin-2-ylsulfonyl)[4-(4-trifluormethylthiazol-2- yl)benzyl]aminomethyl>pyridin-2-ylamino)eddikesyre, (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-4-yl)benzyl]aminomethyl>pyridin-2- ylamino)eddikesyre, (6-{[4-(pyridin-2-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl>pyridin-2- ylamino)eddikesyre, (6-{[4-(pyndazin-4-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl>pyridin-2- ylamino)eddikesyre, (6-{(pyridin-2-ylsulfonyl)[4-(pyrimidin-2-yl)benzyl]aminomethyl>pyridin-2- ylamino)eddikesyre, (6-{[4-(4,5-dihydrothiazol-2-yl)benzyl](4- fluorbenzenesulfonyl)aminomethyl>pyridin-2-ylamino)eddikesyre, {6-[(6-phenylpyridazin-3-ylmethyl)(pyridin-3- ylsulfonyl)aminomethyl]pyridin-2-yl-amino>eddikesyre, hexyl (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl>pyridin-2-yl-amino)acetat, (6-{[4-(5-chlorthiazol-2-yl)benzyl](pyridin-2- ylsulfonyl)aminomethyl}pyridin-2-yl-amino)eddikesyre, (6-{[4-(5-methylthiazol-2-yl)benzyl](pyridin-2- ylsulfonyl)aminomethyl>pyridin-2-yl-amino)eddikesyre, (6-{ [4-(4,5-dimethylthiazol-2-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-ylamino)eddikesyre, (6-{(pyridin-3-ylsulfonyl)[4-(l,2,4-triazol-l- yl)benzyl]aminomethyl}pyridin-2-ylamino)eddikesyre, ethyl (6-{[4-(pyrazol-l-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetat eller isopropyl (6-{[4-(pyrazol-l-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetat.
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