ES2513291T3 - Derivados alquinilo útiles como inhibidores de la DPP-1 - Google Patents
Derivados alquinilo útiles como inhibidores de la DPP-1 Download PDFInfo
- Publication number
- ES2513291T3 ES2513291T3 ES10774098.7T ES10774098T ES2513291T3 ES 2513291 T3 ES2513291 T3 ES 2513291T3 ES 10774098 T ES10774098 T ES 10774098T ES 2513291 T3 ES2513291 T3 ES 2513291T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- 4alkyl
- ethyl
- oxy
- piperidin
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 239000003112 inhibitor Substances 0.000 title description 6
- 125000000304 alkynyl group Chemical group 0.000 title description 4
- -1 piperidinyl-oxy- Chemical class 0.000 abstract description 47
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 229960005222 phenazone Drugs 0.000 description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 38
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 8
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 5
- 102000035195 Peptidases Human genes 0.000 description 4
- 108091005804 Peptidases Proteins 0.000 description 4
- 210000003622 mature neutrocyte Anatomy 0.000 description 4
- 108090000712 Cathepsin B Proteins 0.000 description 3
- 102000004225 Cathepsin B Human genes 0.000 description 3
- 239000004365 Protease Substances 0.000 description 3
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 102000003902 Cathepsin C Human genes 0.000 description 2
- 108090000267 Cathepsin C Proteins 0.000 description 2
- 102100024940 Cathepsin K Human genes 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 2
- 102000010911 Enzyme Precursors Human genes 0.000 description 2
- 108010062466 Enzyme Precursors Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000001398 Granzyme Human genes 0.000 description 2
- 108060005986 Granzyme Proteins 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 210000004969 inflammatory cell Anatomy 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- LKDMKWNDBAVNQZ-UHFFFAOYSA-N 4-[[1-[[1-[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC(C)C(=O)NC(C)C(=O)N1CCCC1C(=O)NC(C(=O)NC=1C=CC(=CC=1)[N+]([O-])=O)CC1=CC=CC=C1 LKDMKWNDBAVNQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 208000000884 Airway Obstruction Diseases 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 108090000617 Cathepsin G Proteins 0.000 description 1
- 102000004173 Cathepsin G Human genes 0.000 description 1
- 108090000619 Cathepsin H Proteins 0.000 description 1
- 102000004175 Cathepsin H Human genes 0.000 description 1
- 108090000625 Cathepsin K Proteins 0.000 description 1
- 108090000624 Cathepsin L Proteins 0.000 description 1
- 102000004172 Cathepsin L Human genes 0.000 description 1
- 101710177066 Cathepsin O Proteins 0.000 description 1
- 108090000613 Cathepsin S Proteins 0.000 description 1
- 102100035654 Cathepsin S Human genes 0.000 description 1
- 102000005600 Cathepsins Human genes 0.000 description 1
- 108010084457 Cathepsins Proteins 0.000 description 1
- 102100024539 Chymase Human genes 0.000 description 1
- 108090000227 Chymases Proteins 0.000 description 1
- 102000005927 Cysteine Proteases Human genes 0.000 description 1
- 108010005843 Cysteine Proteases Proteins 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 102100029921 Dipeptidyl peptidase 1 Human genes 0.000 description 1
- 101710087078 Dipeptidyl peptidase 1 Proteins 0.000 description 1
- 108010028275 Leukocyte Elastase Proteins 0.000 description 1
- 102000005741 Metalloproteases Human genes 0.000 description 1
- 108010006035 Metalloproteases Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102100033174 Neutrophil elastase Human genes 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000001400 Tryptase Human genes 0.000 description 1
- 108060005989 Tryptase Proteins 0.000 description 1
- 208000002223 abdominal aortic aneurysm Diseases 0.000 description 1
- 210000001132 alveolar macrophage Anatomy 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 208000007474 aortic aneurysm Diseases 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 101150080418 ddp-1 gene Proteins 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Health & Medical Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25617109P | 2009-10-29 | 2009-10-29 | |
| US256171P | 2009-10-29 | ||
| PCT/US2010/054445 WO2011059731A1 (en) | 2009-10-29 | 2010-10-28 | Alkynyl derivatives useful as dpp-1 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2513291T3 true ES2513291T3 (es) | 2014-10-24 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10774098.7T Active ES2513291T3 (es) | 2009-10-29 | 2010-10-28 | Derivados alquinilo útiles como inhibidores de la DPP-1 |
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| US (1) | US8633322B2 (enExample) |
| EP (1) | EP2493571B1 (enExample) |
| JP (1) | JP5815542B2 (enExample) |
| CN (1) | CN102596321B (enExample) |
| AU (1) | AU2010319927B2 (enExample) |
| ES (1) | ES2513291T3 (enExample) |
| WO (1) | WO2011059731A1 (enExample) |
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| WO2012119941A1 (en) | 2011-03-04 | 2012-09-13 | Prozymex A/S | Peptidyl nitrilcompounds as peptidase inhibitors |
| EP2825533B1 (en) | 2012-03-13 | 2016-10-19 | Basf Se | Fungicidal pyrimidine compounds |
| AR091858A1 (es) | 2012-07-25 | 2015-03-04 | Sova Pharmaceuticals Inc | INHIBIDORES DE CISTATIONIN-g-LIASA (CSE) |
| CA2923101A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| EP4497473A3 (en) | 2020-08-26 | 2025-04-23 | Haisco Pharmaceuticals Pte. Ltd. | Nitrile derivative that acts as inhibitor of dipeptidyl peptidase 1 and use thereof |
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| US548021A (en) * | 1895-10-15 | Wiiitfield potter toomee | ||
| US4847241A (en) * | 1985-08-14 | 1989-07-11 | G. D. Searle & Co. | Fluorenyl substituted tyrosyl dipeptide amides which are useful in treating pain |
| CA2099994C (en) | 1991-03-06 | 2003-05-20 | Robert B. Garland | Phenyl amidines derivatives useful as platelet aggregation inhibitors |
| US5424334A (en) | 1991-12-19 | 1995-06-13 | G. D. Searle & Co. | Peptide mimetic compounds useful as platelet aggregation inhibitors |
| DE4321502A1 (de) | 1993-06-29 | 1995-01-12 | Bayer Ag | Alkinol-substituierte Peptide, Verfahren zu ihrer Herstellung und ihre Verwendung als antiretrovirale Mittel |
| AU6490396A (en) | 1995-07-14 | 1997-02-18 | Smithkline Beecham Corporation | Substituted-pent-4-ynoic acids |
| NZ318926A (en) | 1995-08-30 | 1999-04-29 | Searle & Co | Alpha v beta 3 integrin (vitronectin) inhibitors or anatagonists derived from benzoic acid for treating diseases of cell adhesion |
| JP2002145897A (ja) | 2000-11-10 | 2002-05-22 | Kyorin Pharmaceut Co Ltd | アミノ酸誘導体及びその製造法 |
| CA2480378A1 (en) * | 2002-05-07 | 2003-11-20 | Neurosearch A/S | Novel azacyclic ethynyl derivatives |
| DE60226906D1 (de) * | 2002-07-31 | 2008-07-10 | Ranbaxy Lab Ltd | 3,6-disubstituierte azabicyclo ä3.1.0ühexanderivate, die sich als muscarinrezeptorantagonisten eignen |
| US20040186151A1 (en) * | 2003-02-12 | 2004-09-23 | Mjalli Adnan M.M. | Substituted azole derivatives as therapeutic agents |
| AU2004210711B2 (en) * | 2003-02-12 | 2010-07-08 | Transtech Pharma, Inc. | Substituted azole derivatives as therapeutic agents |
| US20070155803A1 (en) * | 2003-05-30 | 2007-07-05 | Prozymex A/S | Protease inhibitors |
| US7638513B2 (en) * | 2004-06-02 | 2009-12-29 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| DE102005009784B4 (de) * | 2005-03-03 | 2009-06-18 | Technische Universität Darmstadt | Peptid-Mimetika, Verfahren zur deren Herstellung, diese enthaltende pharmazeutische Zusammensetzung und deren Verwendung als Inhibitoren von Proteasomen und zur Induktion von Apoptose |
| KR20080004550A (ko) * | 2005-03-30 | 2008-01-09 | 콘포마 세러퓨틱스 코포레이션 | Hsp90-억제제로서 알키닐 피롤로피리미딘 및 관련유사체 |
| BRPI0708942A2 (pt) | 2006-03-21 | 2011-06-14 | Joyant Pharmaceuticals Inc | composto promotor de apoptose, uso e mÉtodo de produÇço do mesmo e composiÇço farmacÊutica |
| US7678894B2 (en) | 2007-05-18 | 2010-03-16 | Helicos Biosciences Corporation | Nucleotide analogs |
| TW200922556A (en) | 2007-08-20 | 2009-06-01 | Glaxo Group Ltd | Novel cathepsin C inhibitors and their use |
| BRPI0820665A2 (pt) | 2007-12-12 | 2018-05-29 | Astrazeneca Ab | compostos de peptidil nitrilas, processos para fabricação dos mesmos, composição farmacêutica, combinação e uso de ditos compostos |
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Also Published As
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| CN102596321A (zh) | 2012-07-18 |
| US20110105562A1 (en) | 2011-05-05 |
| JP5815542B2 (ja) | 2015-11-17 |
| US8633322B2 (en) | 2014-01-21 |
| WO2011059731A1 (en) | 2011-05-19 |
| CN102596321B (zh) | 2014-11-19 |
| AU2010319927A1 (en) | 2012-05-17 |
| JP2013509423A (ja) | 2013-03-14 |
| AU2010319927B2 (en) | 2015-01-22 |
| EP2493571A1 (en) | 2012-09-05 |
| EP2493571B1 (en) | 2014-07-23 |
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