CA2896032A1 - Peri-carbinols - Google Patents
Peri-carbinols Download PDFInfo
- Publication number
- CA2896032A1 CA2896032A1 CA2896032A CA2896032A CA2896032A1 CA 2896032 A1 CA2896032 A1 CA 2896032A1 CA 2896032 A CA2896032 A CA 2896032A CA 2896032 A CA2896032 A CA 2896032A CA 2896032 A1 CA2896032 A1 CA 2896032A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- alkyl
- pharmaceutically acceptable
- independently
- acceptable salt
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 238000000034 method Methods 0.000 claims abstract description 38
- 208000002780 macular degeneration Diseases 0.000 claims abstract description 25
- 208000024891 symptom Diseases 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 38
- 208000017442 Retinal disease Diseases 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 238000009825 accumulation Methods 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 16
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 16
- 230000002207 retinal effect Effects 0.000 claims description 16
- 230000011664 signaling Effects 0.000 claims description 16
- 230000011506 response to oxidative stress Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 description 34
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 34
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- 230000015572 biosynthetic process Effects 0.000 description 25
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 150000002466 imines Chemical class 0.000 description 18
- 208000011325 dry age related macular degeneration Diseases 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 101150041968 CDC13 gene Proteins 0.000 description 13
- 229920000858 Cyclodextrin Polymers 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 206010064930 age-related macular degeneration Diseases 0.000 description 13
- -1 alkyl Grignard reagents Chemical class 0.000 description 13
- 210000001519 tissue Anatomy 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 208000008069 Geographic Atrophy Diseases 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 208000000208 Wet Macular Degeneration Diseases 0.000 description 9
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 150000002537 isoquinolines Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 229910004373 HOAc Inorganic materials 0.000 description 7
- 101100326677 Onchocerca volvulus crt-1 gene Proteins 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 208000027073 Stargardt disease Diseases 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- 235000019698 starch Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 108091008695 photoreceptors Proteins 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
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- 108050001704 Opsin Proteins 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- FMASHOOOLPDQTK-UHFFFAOYSA-L disodium;4-(4-sulfonatobutoxy)butane-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCCCOCCCCS([O-])(=O)=O FMASHOOOLPDQTK-UHFFFAOYSA-L 0.000 description 5
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- 229910052740 iodine Inorganic materials 0.000 description 5
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- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
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- 230000000007 visual effect Effects 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- PTYIXDREKLQDLF-UHFFFAOYSA-N 2-(3-amino-6-chloroquinolin-4-yl)propan-2-ol Chemical compound C1=C(Cl)C=C2C(C(C)(O)C)=C(N)C=NC2=C1 PTYIXDREKLQDLF-UHFFFAOYSA-N 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
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- SMHPLBXIVNQFBA-UHFFFAOYSA-N 6-nitroquinoline Chemical class N1=CC=CC2=CC([N+](=O)[O-])=CC=C21 SMHPLBXIVNQFBA-UHFFFAOYSA-N 0.000 description 4
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001578 tight junction Anatomy 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epidemiology (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261740197P | 2012-12-20 | 2012-12-20 | |
| US61/740,197 | 2012-12-20 | ||
| PCT/US2013/076592 WO2014100425A1 (en) | 2012-12-20 | 2013-12-19 | Peri-carbinols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2896032A1 true CA2896032A1 (en) | 2014-06-26 |
Family
ID=50979217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2896032A Abandoned CA2896032A1 (en) | 2012-12-20 | 2013-12-19 | Peri-carbinols |
Country Status (14)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2325171B1 (en) | 2005-05-26 | 2013-10-09 | Aldexa Therapeutics, Inc. | Quinoline derivatives for treating retinal diseases |
| US9814701B2 (en) | 2009-12-11 | 2017-11-14 | Aldeyra Therapeutics, Inc. | Compositions and methods for the treatment of macular degeneration |
| PE20151433A1 (es) | 2012-12-21 | 2015-10-16 | Alios Biopharma Inc | Nucleosidos sustituidos, nucleotidos y analogos de los mismos |
| CN105120866B (zh) | 2013-01-23 | 2020-02-14 | 奥尔德拉医疗公司 | 与毒性醛相关的疾病和治疗 |
| MX2015009444A (es) | 2013-01-25 | 2016-04-15 | Aldeyra Therapeutics Inc | Trampas novedosas en el tratamiento de la degeneracion macular. |
| CN118724806A (zh) | 2015-08-21 | 2024-10-01 | 奥尔德拉医疗公司 | 氘化化合物和其用途 |
| EP3337470A4 (en) * | 2015-08-21 | 2019-02-27 | Aldeyra Therapeutics, Inc. | ALDEHYDE CONJUGATES AND USES THEREOF |
| BR112018069533A2 (pt) | 2016-02-28 | 2019-04-16 | Aldeyra Therapeutics, Inc. | tratamento de condições alérgicas oculares com ciclodextrinas |
| EP3454858A4 (en) | 2016-05-09 | 2020-01-15 | Aldeyra Therapeutics, Inc. | COMBINATION TREATMENT OF FLAMMABLE CONDITIONS AND DISEASES OF THE EYE |
| CA3032521A1 (en) * | 2016-08-22 | 2018-03-01 | Aldeyra Therapeutics, Inc. | Aldehyde trapping compounds and uses thereof |
| AU2018234919A1 (en) | 2017-03-16 | 2019-09-19 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| US11040039B2 (en) | 2017-10-10 | 2021-06-22 | Aldeyra Therapeutics, Inc. | Treatment of inflammatory disorders |
| JP2021533154A (ja) | 2018-08-06 | 2021-12-02 | アルデイラ セラピューティクス， インコーポレイテッド | 多形化合物およびその使用 |
| US11197821B2 (en) | 2018-09-25 | 2021-12-14 | Aldeyra Therapeutics, Inc. | Formulations for treatment of dry eye disease |
| US11786518B2 (en) | 2019-03-26 | 2023-10-17 | Aldeyra Therapeutics, Inc. | Ophthalmic formulations and uses thereof |
| US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| WO2020223685A1 (en) | 2019-05-02 | 2020-11-05 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| JP2023526016A (ja) | 2020-05-13 | 2023-06-20 | アルデイラ セラピューティクス， インコーポレイテッド | 医薬製剤およびその使用 |
| AU2021308209A1 (en) | 2020-07-16 | 2023-02-09 | Dermavant Sciences GmbH | Isoquinoline compounds and their use in treating ahr imbalance |
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| US2086186A (en) | 1933-10-10 | 1937-07-06 | Us Rubber Co | Treatment of rubber |
| SU509046A1 (ru) | 1975-02-21 | 1984-06-23 | Всесоюзный научно-исследовательский химико-фармацевтический институт им.Серго Орджоникидзе | Производные 2-карбэтокси-3-аминоиндола,про вл ющие противовоспалительную активность, и способ их получени |
| US4675332A (en) | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| GB8610981D0 (en) | 1986-05-06 | 1986-06-11 | Ici America Inc | Quinoline amides |
| CA2054339C (en) | 1990-11-02 | 2002-12-24 | Francesco G. Salituro | 3-amidoindolyl derivatives |
| US5668117A (en) | 1991-02-22 | 1997-09-16 | Shapiro; Howard K. | Methods of treating neurological diseases and etiologically related symptomology using carbonyl trapping agents in combination with previously known medicaments |
| US6444221B1 (en) | 1992-06-30 | 2002-09-03 | Howard K. Shapiro | Methods of treating chronic inflammatory diseases using carbonyl trapping agents |
| US20050090553A1 (en) | 1992-06-30 | 2005-04-28 | Shapiro Howard K. | Compositions and method for treatment of chronic inflammatory diseases |
| US5472954A (en) | 1992-07-14 | 1995-12-05 | Cyclops H.F. | Cyclodextrin complexation |
| US5493027A (en) | 1993-01-22 | 1996-02-20 | Board Of Regents, The University Of Texas System | Anticonvulsive agents and uses thereof |
| US5597823A (en) | 1995-01-27 | 1997-01-28 | Abbott Laboratories | Tricyclic substituted hexahydrobenz [e]isoindole alpha-1 adrenergic antagonists |
| CA2261916A1 (en) | 1996-08-01 | 1998-02-12 | Dowelanco Llc | 4-substituted quinoline derivatives having fungicidal activity |
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| EP2324823A3 (en) | 2003-03-14 | 2011-11-16 | University of Washington | Retinoid replacements and opsin agonists and methods for the use thereof |
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| TW200640443A (en) | 2005-02-23 | 2006-12-01 | Alcon Inc | Methods for treating ocular angiogenesis, retinal edema, retinal ischemia, and diabetic retinopathy using selective RTK inhibitors |
| EP2325171B1 (en) | 2005-05-26 | 2013-10-09 | Aldexa Therapeutics, Inc. | Quinoline derivatives for treating retinal diseases |
| EP2012789B1 (en) * | 2006-04-14 | 2013-09-25 | Prana Biotechnology Limited | Method of treatment of age-related macular degeneration (AMD) |
| AU2007280984A1 (en) | 2006-07-25 | 2008-02-07 | Envivo Pharmaceutical Inc. | Quinoline derivatives |
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| JP5815552B2 (ja) | 2009-12-08 | 2015-11-17 | ケース ウェスタン リザーブ ユニバーシティＣａｓｅ Ｗｅｓｔｅｒｎｒｅｓｅｒｖｅ Ｕｎｉｖｅｒｓｉｔｙ | 眼疾患を治療する化合物および方法 |
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| MX2015009444A (es) | 2013-01-25 | 2016-04-15 | Aldeyra Therapeutics Inc | Trampas novedosas en el tratamiento de la degeneracion macular. |
| EP3151818A4 (en) | 2014-06-04 | 2018-05-30 | Case Western Reserve University | Compositions and methods of treating diabetic retinopathy |
| WO2016085939A2 (en) | 2014-11-24 | 2016-06-02 | Case Western Reserve University | Compounds and methods of treating ocular disorders |
-
2013
- 2013-12-19 US US14/653,771 patent/US9604997B2/en active Active
- 2013-12-19 SG SG11201504859YA patent/SG11201504859YA/en unknown
- 2013-12-19 JP JP2015549717A patent/JP2016503797A/ja not_active Withdrawn
- 2013-12-19 EP EP13865015.5A patent/EP2935220A4/en not_active Withdrawn
- 2013-12-19 CA CA2896032A patent/CA2896032A1/en not_active Abandoned
- 2013-12-19 KR KR1020157019397A patent/KR20150118106A/ko not_active Withdrawn
- 2013-12-19 AU AU2013361314A patent/AU2013361314A1/en not_active Abandoned
- 2013-12-19 WO PCT/US2013/076592 patent/WO2014100425A1/en not_active Ceased
- 2013-12-19 CN CN201380067618.3A patent/CN105073714A/zh active Pending
- 2013-12-19 HK HK16105238.3A patent/HK1217325A1/zh unknown
- 2013-12-19 RU RU2015120478A patent/RU2015120478A/ru unknown
- 2013-12-19 MX MX2015007916A patent/MX2015007916A/es unknown
-
2015
- 2015-06-03 IL IL239178A patent/IL239178A0/en unknown
- 2015-06-18 CL CL2015001754A patent/CL2015001754A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2013361314A1 (en) | 2015-07-02 |
| EP2935220A4 (en) | 2016-04-27 |
| SG11201504859YA (en) | 2015-07-30 |
| IL239178A0 (en) | 2015-07-30 |
| CN105073714A (zh) | 2015-11-18 |
| US20150344432A1 (en) | 2015-12-03 |
| CL2015001754A1 (es) | 2015-11-06 |
| US9604997B2 (en) | 2017-03-28 |
| RU2015120478A (ru) | 2017-01-25 |
| KR20150118106A (ko) | 2015-10-21 |
| EP2935220A1 (en) | 2015-10-28 |
| JP2016503797A (ja) | 2016-02-08 |
| HK1217325A1 (zh) | 2017-01-06 |
| WO2014100425A1 (en) | 2014-06-26 |
| MX2015007916A (es) | 2016-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20181219 |