CA2794607A1 - Dosage regimen of diaryl sulfide derivatives - Google Patents
Dosage regimen of diaryl sulfide derivatives Download PDFInfo
- Publication number
- CA2794607A1 CA2794607A1 CA2794607A CA2794607A CA2794607A1 CA 2794607 A1 CA2794607 A1 CA 2794607A1 CA 2794607 A CA2794607 A CA 2794607A CA 2794607 A CA2794607 A CA 2794607A CA 2794607 A1 CA2794607 A1 CA 2794607A1
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- CA
- Canada
- Prior art keywords
- compound
- 4alkyl
- formula
- dosage
- 4alkoxy
- 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
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- -1 diaryl sulfide derivatives Chemical class 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 238000011282 treatment Methods 0.000 claims abstract description 66
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical group 0.000 claims abstract description 27
- 239000000651 prodrug Substances 0.000 claims abstract description 26
- 229940002612 prodrug Drugs 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000012453 solvate Substances 0.000 claims abstract description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 230000001363 autoimmune Effects 0.000 claims abstract description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract description 3
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- 238000011221 initial treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 208000001875 irritant dermatitis Diseases 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 201000010666 keratoconjunctivitis Diseases 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- KUKSUQKELVOKBH-UHFFFAOYSA-N n-[bis[(2-methylpropan-2-yl)oxy]phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(OC(C)(C)C)OC(C)(C)C KUKSUQKELVOKBH-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960000244 procainamide Drugs 0.000 description 1
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 201000002932 second-degree atrioventricular block Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- 231100000617 superantigen Toxicity 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
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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
- A61K31/13—Amines
- A61K31/145—Amines having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2)
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Transplantation (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10162082 | 2010-05-06 | ||
| EP10162082.1 | 2010-05-06 | ||
| PCT/EP2011/057210 WO2011138398A1 (en) | 2010-05-06 | 2011-05-05 | Dosage regimen of diaryl sulfide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2794607A1 true CA2794607A1 (en) | 2011-11-10 |
Family
ID=42236590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2794607A Abandoned CA2794607A1 (en) | 2010-05-06 | 2011-05-05 | Dosage regimen of diaryl sulfide derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US20130210924A1 (https=) |
| EP (1) | EP2566473B1 (https=) |
| JP (3) | JP2013525469A (https=) |
| KR (1) | KR20130098885A (https=) |
| CN (2) | CN102917698A (https=) |
| AU (1) | AU2011249789B2 (https=) |
| BR (1) | BR112012028248A2 (https=) |
| CA (1) | CA2794607A1 (https=) |
| EA (1) | EA201201515A1 (https=) |
| ES (1) | ES2562416T3 (https=) |
| MX (1) | MX2012012925A (https=) |
| WO (1) | WO2011138398A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI519539B (zh) * | 2010-12-21 | 2016-02-01 | Kyorin Seiyaku Kk | Diphenyl sulfide derivatives and pharmaceuticals as an active ingredient thereof |
| US20160000811A1 (en) | 2013-02-20 | 2016-01-07 | Novartis Ag | Treatment of graft versus host disease in transplant patients |
| EP4248958A3 (en) * | 2021-01-28 | 2024-01-03 | Priothera SAS | Methods of treatment with s1p receptor modulators |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1431275B1 (en) | 2001-09-27 | 2010-04-07 | Kyorin Pharmaceutical Co., Ltd. | Diaryl ether derivative, addition salt thereof, and immunosuppressant |
| MXPA04002679A (es) * | 2001-09-27 | 2004-07-30 | Kyorin Seiyaku Kk | Derivados de sulfuro de diarilo, sales de los mismos y agentes inmunosupresores que utilizan los mismos. |
| KR101003877B1 (ko) * | 2002-09-19 | 2010-12-30 | 교린 세이야꾸 가부시키 가이샤 | 아미노알코올 유도체와 그 부가염 및 면역 억제제 |
| US7456157B2 (en) | 2003-02-18 | 2008-11-25 | Kyorin Pharmaceutical Co., Ltd. | Aminophosphonic acid derivatives, addition salts thereof and S1P receptor modulators |
| CN1874996B (zh) | 2003-08-28 | 2011-05-18 | 诺瓦提斯公司 | 氨基丙醇衍生物 |
| CN101014329B (zh) * | 2004-07-16 | 2010-09-08 | 杏林制药株式会社 | 用于对器官或组织的移植的排异反应或骨髓移植的移植物抗宿主反应预防或治疗的药物组合物 |
| WO2006041015A1 (ja) * | 2004-10-12 | 2006-04-20 | Kyorin Pharmaceutical Co., Ltd. | アミノアルコール誘導体とその付加塩及び免疫抑制剤 |
| KR20140095109A (ko) * | 2004-11-29 | 2014-07-31 | 노파르티스 아게 | Ｓ１ｐ 수용체 효능제의 투여 용법 |
| SI2295049T1 (sl) * | 2005-09-09 | 2015-03-31 | Novartis Ag | Zdravljenje avtoimunskih bolezni |
| HUE033168T2 (en) * | 2008-03-17 | 2017-11-28 | Actelion Pharmaceuticals Ltd | Dosage regimen for selective SIP1 receptor agonist |
| CN102119028A (zh) * | 2008-08-18 | 2011-07-06 | 诺瓦提斯公司 | 用于治疗脱髓鞘性周围神经病的氨基醇衍生物 |
| CN105213372A (zh) * | 2008-12-22 | 2016-01-06 | 诺华股份有限公司 | S1p受体激动剂的给药方案 |
| RS66784B9 (sr) * | 2008-12-22 | 2025-08-29 | Novartis Ag | Režim doziranјa agonista s1p receptora |
-
2011
- 2011-05-05 EP EP11720419.8A patent/EP2566473B1/en active Active
- 2011-05-05 CA CA2794607A patent/CA2794607A1/en not_active Abandoned
- 2011-05-05 BR BR112012028248A patent/BR112012028248A2/pt not_active IP Right Cessation
- 2011-05-05 ES ES11720419.8T patent/ES2562416T3/es active Active
- 2011-05-05 US US13/643,324 patent/US20130210924A1/en not_active Abandoned
- 2011-05-05 CN CN2011800227113A patent/CN102917698A/zh active Pending
- 2011-05-05 KR KR1020127031867A patent/KR20130098885A/ko not_active Withdrawn
- 2011-05-05 EA EA201201515A patent/EA201201515A1/ru unknown
- 2011-05-05 WO PCT/EP2011/057210 patent/WO2011138398A1/en not_active Ceased
- 2011-05-05 CN CN201610590854.9A patent/CN106309416A/zh active Pending
- 2011-05-05 AU AU2011249789A patent/AU2011249789B2/en not_active Expired - Fee Related
- 2011-05-05 MX MX2012012925A patent/MX2012012925A/es not_active Application Discontinuation
- 2011-05-05 JP JP2013508506A patent/JP2013525469A/ja not_active Withdrawn
-
2014
- 2014-07-28 US US14/341,891 patent/US20140336265A1/en not_active Abandoned
-
2016
- 2016-04-14 JP JP2016081108A patent/JP6290963B2/ja not_active Expired - Fee Related
- 2016-10-19 US US15/297,683 patent/US20170119702A1/en not_active Abandoned
-
2017
- 2017-12-07 US US15/834,482 patent/US20180161290A1/en not_active Abandoned
-
2018
- 2018-02-08 JP JP2018020950A patent/JP6615247B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102917698A (zh) | 2013-02-06 |
| JP6290963B2 (ja) | 2018-03-07 |
| KR20130098885A (ko) | 2013-09-05 |
| WO2011138398A1 (en) | 2011-11-10 |
| JP2016183159A (ja) | 2016-10-20 |
| EP2566473A1 (en) | 2013-03-13 |
| US20130210924A1 (en) | 2013-08-15 |
| ES2562416T3 (es) | 2016-03-04 |
| US20140336265A1 (en) | 2014-11-13 |
| EA201201515A1 (ru) | 2013-08-30 |
| JP6615247B2 (ja) | 2019-12-04 |
| JP2013525469A (ja) | 2013-06-20 |
| US20170119702A1 (en) | 2017-05-04 |
| JP2018100280A (ja) | 2018-06-28 |
| MX2012012925A (es) | 2012-12-17 |
| BR112012028248A2 (pt) | 2016-08-02 |
| AU2011249789B2 (en) | 2015-03-19 |
| CN106309416A (zh) | 2017-01-11 |
| US20180161290A1 (en) | 2018-06-14 |
| AU2011249789A1 (en) | 2012-12-13 |
| EP2566473B1 (en) | 2016-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20170505 |