CA2981631C - A specific trifluoroethyl quinoline analogue for use in the treatment of sjogren's syndrome - Google Patents
A specific trifluoroethyl quinoline analogue for use in the treatment of sjogren's syndrome Download PDFInfo
- Publication number
- CA2981631C CA2981631C CA2981631A CA2981631A CA2981631C CA 2981631 C CA2981631 C CA 2981631C CA 2981631 A CA2981631 A CA 2981631A CA 2981631 A CA2981631 A CA 2981631A CA 2981631 C CA2981631 C CA 2981631C
- Authority
- CA
- Canada
- Prior art keywords
- syndrome
- sjogren
- treatment
- trifluoroethyl
- compound
- 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.)
- Active
Links
- 208000021386 Sjogren Syndrome Diseases 0.000 title claims abstract description 27
- JOAPFEPXYNWUKS-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)quinoline Chemical class C1=CC=CC2=NC(CC(F)(F)F)=CC=C21 JOAPFEPXYNWUKS-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 208000034943 Primary Sjögren syndrome Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 abstract description 6
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 abstract 1
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- 101000738771 Homo sapiens Receptor-type tyrosine-protein phosphatase C Proteins 0.000 description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 2
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- 102100037422 Receptor-type tyrosine-protein phosphatase C Human genes 0.000 description 2
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- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 2
- 229960004171 hydroxychloroquine Drugs 0.000 description 2
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- 239000002674 ointment Substances 0.000 description 2
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- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- 239000003826 tablet Substances 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- 229930091051 Arenine Natural products 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
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- 102100024222 B-lymphocyte antigen CD19 Human genes 0.000 description 1
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- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 102100032768 Complement receptor type 2 Human genes 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
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- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- 239000002260 anti-inflammatory agent Substances 0.000 description 1
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- WUTYZMFRCNBCHQ-PSASIEDQSA-N cevimeline Chemical compound C1S[C@H](C)O[C@]21C(CC1)CCN1C2 WUTYZMFRCNBCHQ-PSASIEDQSA-N 0.000 description 1
- 229960001314 cevimeline Drugs 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
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- 108010007093 dispase Proteins 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
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- 230000002526 effect on cardiovascular system Effects 0.000 description 1
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- 230000006862 enzymatic digestion Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003499 exocrine gland Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
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- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
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- 239000006210 lotion Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000005210 lymphoid organ Anatomy 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 239000008188 pellet Substances 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940126532 prescription medicine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
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- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 208000005494 xerophthalmia Diseases 0.000 description 1
Classifications
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0031—Rectum, anus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Physiology (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1506786.1 | 2015-04-21 | ||
| GBGB1506786.1A GB201506786D0 (en) | 2015-04-21 | 2015-04-21 | Therapeutic use |
| PCT/EP2016/058810 WO2016170014A1 (en) | 2015-04-21 | 2016-04-20 | A specific trifluoroethyl quinoline analogue for use in the treatment of sjögren's syndrome |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2981631A1 CA2981631A1 (en) | 2016-10-27 |
| CA2981631C true CA2981631C (en) | 2023-02-21 |
Family
ID=53298950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2981631A Active CA2981631C (en) | 2015-04-21 | 2016-04-20 | A specific trifluoroethyl quinoline analogue for use in the treatment of sjogren's syndrome |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US10493074B2 (enExample) |
| EP (1) | EP3285772B1 (enExample) |
| JP (1) | JP6721606B2 (enExample) |
| KR (1) | KR102627370B1 (enExample) |
| CN (1) | CN107530344B (enExample) |
| AR (1) | AR105552A1 (enExample) |
| AU (1) | AU2016251236B2 (enExample) |
| BR (1) | BR112017020591B8 (enExample) |
| CA (1) | CA2981631C (enExample) |
| CL (1) | CL2017002669A1 (enExample) |
| CO (1) | CO2017010573A2 (enExample) |
| CY (1) | CY1122572T1 (enExample) |
| DK (1) | DK3285772T3 (enExample) |
| EA (1) | EA032432B1 (enExample) |
| ES (1) | ES2763335T3 (enExample) |
| GB (1) | GB201506786D0 (enExample) |
| HR (1) | HRP20192273T1 (enExample) |
| HU (1) | HUE047162T2 (enExample) |
| IL (1) | IL254766B (enExample) |
| LT (1) | LT3285772T (enExample) |
| MX (1) | MX2017013148A (enExample) |
| MY (1) | MY192972A (enExample) |
| PL (1) | PL3285772T3 (enExample) |
| PT (1) | PT3285772T (enExample) |
| SG (1) | SG11201707789YA (enExample) |
| SI (1) | SI3285772T1 (enExample) |
| WO (1) | WO2016170014A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4467565A3 (en) | 2016-12-21 | 2025-03-12 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| GB201708856D0 (en) | 2017-06-02 | 2017-07-19 | Ucb Biopharma Sprl | Seletalisib crystalline forms |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS55546B1 (sr) * | 2004-05-13 | 2017-05-31 | Icos Corp | Hinazolinoni kao inhibitori humane fosfatidilonozitol 3-delta kinaze |
| PL2137186T3 (pl) * | 2007-03-23 | 2016-09-30 | Związki heterocykliczne i ich zastosowania | |
| AP2012006294A0 (en) * | 2009-11-05 | 2012-06-30 | Rhizen Pharmaceuticals Sa | Novel kinase modulators. |
| UA112517C2 (uk) * | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| AR082799A1 (es) | 2010-09-08 | 2013-01-09 | Ucb Pharma Sa | Derivados de quinolina y quinoxalina como inhibidores de quinasa |
| NZ714710A (en) * | 2013-06-14 | 2016-11-25 | Gilead Sciences Inc | Phosphatidylinositol 3-kinase inhibitors |
-
2015
- 2015-04-21 GB GBGB1506786.1A patent/GB201506786D0/en not_active Ceased
-
2016
- 2016-04-20 EA EA201792318A patent/EA032432B1/ru not_active IP Right Cessation
- 2016-04-20 PT PT167193564T patent/PT3285772T/pt unknown
- 2016-04-20 SG SG11201707789YA patent/SG11201707789YA/en unknown
- 2016-04-20 ES ES16719356T patent/ES2763335T3/es active Active
- 2016-04-20 MX MX2017013148A patent/MX2017013148A/es active IP Right Grant
- 2016-04-20 CA CA2981631A patent/CA2981631C/en active Active
- 2016-04-20 WO PCT/EP2016/058810 patent/WO2016170014A1/en not_active Ceased
- 2016-04-20 JP JP2017554426A patent/JP6721606B2/ja active Active
- 2016-04-20 KR KR1020177031275A patent/KR102627370B1/ko active Active
- 2016-04-20 AR ARP160101079A patent/AR105552A1/es not_active Application Discontinuation
- 2016-04-20 DK DK16719356.4T patent/DK3285772T3/da active
- 2016-04-20 EP EP16719356.4A patent/EP3285772B1/en active Active
- 2016-04-20 LT LTEP16719356.4T patent/LT3285772T/lt unknown
- 2016-04-20 CN CN201680022982.1A patent/CN107530344B/zh active Active
- 2016-04-20 HU HUE16719356A patent/HUE047162T2/hu unknown
- 2016-04-20 MY MYPI2017703917A patent/MY192972A/en unknown
- 2016-04-20 BR BR112017020591A patent/BR112017020591B8/pt active IP Right Grant
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