CA2795394A1 - Treatment of autoimmune diseases - Google Patents
Treatment of autoimmune diseases Download PDFInfo
- Publication number
- CA2795394A1 CA2795394A1 CA2795394A CA2795394A CA2795394A1 CA 2795394 A1 CA2795394 A1 CA 2795394A1 CA 2795394 A CA2795394 A CA 2795394A CA 2795394 A CA2795394 A CA 2795394A CA 2795394 A1 CA2795394 A1 CA 2795394A1
- Authority
- CA
- Canada
- Prior art keywords
- 4alkyl
- 4alkoxy
- compound
- halogen
- formula
- 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
- 238000011282 treatment Methods 0.000 title claims abstract description 34
- 208000023275 Autoimmune disease Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 36
- 150000002367 halogens Chemical group 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 229940002612 prodrug Drugs 0.000 claims abstract description 32
- 239000000651 prodrug Substances 0.000 claims abstract description 32
- 239000012453 solvate Substances 0.000 claims abstract description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 22
- 230000001363 autoimmune Effects 0.000 claims abstract description 20
- -1 trifluoromethoxy, phenoxy, cyclohexylmethyloxy, pyridylmethoxy, cinnamyloxy, naphthylmethoxy, phenoxymethyl Chemical group 0.000 claims abstract description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
- 238000011321 prophylaxis Methods 0.000 claims abstract description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 8
- 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 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 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 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 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 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000006372 monohalo methyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 4
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims description 39
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- XXHKHLYABSAFDW-UHFFFAOYSA-N 5-amino-5-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]pentane-1,3-diol Chemical compound C1=C(Cl)C(C(CC(O)CCO)N)=CC=C1SC1=CC=CC(OCC=2C=CC=CC=2)=C1 XXHKHLYABSAFDW-UHFFFAOYSA-N 0.000 claims description 7
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- JZHXIFZZZFFZBQ-XMMPIXPASA-N [(2r)-2-amino-4-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]-2-(hydroxymethyl)butyl] dihydrogen phosphate Chemical compound C1=C(Cl)C(CC[C@](CO)(N)COP(O)(O)=O)=CC=C1SC1=CC=CC(OCC=2C=CC=CC=2)=C1 JZHXIFZZZFFZBQ-XMMPIXPASA-N 0.000 claims description 3
- JZHXIFZZZFFZBQ-DEOSSOPVSA-N [(2s)-2-amino-4-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]-2-(hydroxymethyl)butyl] dihydrogen phosphate Chemical compound C1=C(Cl)C(CC[C@@](CO)(N)COP(O)(O)=O)=CC=C1SC1=CC=CC(OCC=2C=CC=CC=2)=C1 JZHXIFZZZFFZBQ-DEOSSOPVSA-N 0.000 claims description 3
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 19
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- A61K31/66—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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/30—Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10162079 | 2010-05-06 | ||
| EP10162079.7 | 2010-05-06 | ||
| PCT/EP2011/057203 WO2011138393A1 (en) | 2010-05-06 | 2011-05-05 | Treatment of autoimmune diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2795394A1 true CA2795394A1 (en) | 2011-11-10 |
Family
ID=42199281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2795394A Abandoned CA2795394A1 (en) | 2010-05-06 | 2011-05-05 | Treatment of autoimmune diseases |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20130172297A1 (https=) |
| EP (1) | EP2566470A1 (https=) |
| JP (1) | JP2013530937A (https=) |
| KR (1) | KR20130066630A (https=) |
| CN (1) | CN102869353A (https=) |
| AU (1) | AU2011249784B2 (https=) |
| BR (1) | BR112012028190A2 (https=) |
| CA (1) | CA2795394A1 (https=) |
| CL (1) | CL2012003091A1 (https=) |
| CR (1) | CR20120566A (https=) |
| CU (1) | CU20120154A7 (https=) |
| EA (1) | EA201201514A1 (https=) |
| EC (1) | ECSP12012312A (https=) |
| IL (1) | IL222690A0 (https=) |
| MA (1) | MA34285B1 (https=) |
| MX (1) | MX2012012926A (https=) |
| NZ (1) | NZ603999A (https=) |
| PE (1) | PE20130612A1 (https=) |
| PH (1) | PH12012502418A1 (https=) |
| SG (1) | SG185746A1 (https=) |
| TN (1) | TN2012000509A1 (https=) |
| TW (1) | TW201201814A (https=) |
| WO (1) | WO2011138393A1 (https=) |
| ZA (1) | ZA201207710B (https=) |
Families Citing this family (2)
| 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 |
| US9289494B2 (en) | 2013-11-20 | 2016-03-22 | RestorTears, LLC | Method of treating ocular disorders with compounds found in Harderian gland secretions |
Family Cites Families (10)
| 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 |
| JP4716996B2 (ja) * | 2003-05-26 | 2011-07-06 | 武田薬品工業株式会社 | スルホピロール |
| CN1874996B (zh) | 2003-08-28 | 2011-05-18 | 诺瓦提斯公司 | 氨基丙醇衍生物 |
| EP1723138B1 (en) * | 2004-02-11 | 2010-07-14 | Basilea Pharmaceutica AG | Substituted benzimidazoles and their use for inducing apoptosis |
| 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 |
| GB0504544D0 (en) * | 2005-03-04 | 2005-04-13 | Novartis Ag | Organic compounds |
| SI2295049T1 (sl) * | 2005-09-09 | 2015-03-31 | Novartis Ag | Zdravljenje avtoimunskih bolezni |
-
2011
- 2011-05-05 MX MX2012012926A patent/MX2012012926A/es not_active Application Discontinuation
- 2011-05-05 PH PH1/2012/502418A patent/PH12012502418A1/en unknown
- 2011-05-05 US US13/643,320 patent/US20130172297A1/en not_active Abandoned
- 2011-05-05 WO PCT/EP2011/057203 patent/WO2011138393A1/en not_active Ceased
- 2011-05-05 BR BR112012028190A patent/BR112012028190A2/pt not_active IP Right Cessation
- 2011-05-05 NZ NZ603999A patent/NZ603999A/en not_active IP Right Cessation
- 2011-05-05 PE PE2012002122A patent/PE20130612A1/es not_active Application Discontinuation
- 2011-05-05 SG SG2012086526A patent/SG185746A1/en unknown
- 2011-05-05 TW TW100115816A patent/TW201201814A/zh unknown
- 2011-05-05 JP JP2013508502A patent/JP2013530937A/ja active Pending
- 2011-05-05 AU AU2011249784A patent/AU2011249784B2/en not_active Ceased
- 2011-05-05 EP EP11723889A patent/EP2566470A1/en not_active Withdrawn
- 2011-05-05 EA EA201201514A patent/EA201201514A1/ru unknown
- 2011-05-05 KR KR1020127031868A patent/KR20130066630A/ko not_active Withdrawn
- 2011-05-05 CN CN2011800224469A patent/CN102869353A/zh active Pending
- 2011-05-05 CA CA2795394A patent/CA2795394A1/en not_active Abandoned
- 2011-05-05 MA MA35416A patent/MA34285B1/fr unknown
-
2012
- 2012-10-15 ZA ZA2012/07710A patent/ZA201207710B/en unknown
- 2012-10-23 TN TNP2012000509A patent/TN2012000509A1/en unknown
- 2012-10-25 IL IL222690A patent/IL222690A0/en unknown
- 2012-11-05 CU CU2012000154A patent/CU20120154A7/es unknown
- 2012-11-06 CR CR20120566A patent/CR20120566A/es unknown
- 2012-11-06 CL CL2012003091A patent/CL2012003091A1/es unknown
- 2012-11-27 EC ECSP12012312 patent/ECSP12012312A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CU20120154A7 (es) | 2013-03-27 |
| CR20120566A (es) | 2013-01-09 |
| PH12012502418A1 (en) | 2018-03-21 |
| SG185746A1 (en) | 2013-01-30 |
| BR112012028190A2 (pt) | 2016-08-02 |
| IL222690A0 (en) | 2012-12-31 |
| MX2012012926A (es) | 2012-12-17 |
| KR20130066630A (ko) | 2013-06-20 |
| ECSP12012312A (es) | 2012-12-28 |
| NZ603999A (en) | 2014-06-27 |
| PE20130612A1 (es) | 2013-06-06 |
| TN2012000509A1 (en) | 2014-04-01 |
| US20130172297A1 (en) | 2013-07-04 |
| EA201201514A1 (ru) | 2013-05-30 |
| CN102869353A (zh) | 2013-01-09 |
| MA34285B1 (fr) | 2013-06-01 |
| AU2011249784B2 (en) | 2014-03-06 |
| WO2011138393A1 (en) | 2011-11-10 |
| AU2011249784A1 (en) | 2012-12-20 |
| JP2013530937A (ja) | 2013-08-01 |
| ZA201207710B (en) | 2013-06-26 |
| CL2012003091A1 (es) | 2013-03-22 |
| TW201201814A (en) | 2012-01-16 |
| EP2566470A1 (en) | 2013-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20160505 |