CA2705294C - Methods of treating arthritis by the administration of substituted benzenesulfonamides - Google Patents
Methods of treating arthritis by the administration of substituted benzenesulfonamides Download PDFInfo
- Publication number
- CA2705294C CA2705294C CA2705294A CA2705294A CA2705294C CA 2705294 C CA2705294 C CA 2705294C CA 2705294 A CA2705294 A CA 2705294A CA 2705294 A CA2705294 A CA 2705294A CA 2705294 C CA2705294 C CA 2705294C
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- Prior art keywords
- methyl
- amino
- phenylsulfanyl
- propyl
- piperazin
- 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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- 206010003246 arthritis Diseases 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title abstract description 14
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 532
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 245
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 240
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 95
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 51
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- AGHLUVOCTHWMJV-UHFFFAOYSA-J sodium;gold(3+);2-sulfanylbutanedioate Chemical compound [Na+].[Au+3].[O-]C(=O)CC(S)C([O-])=O.[O-]C(=O)CC(S)C([O-])=O AGHLUVOCTHWMJV-UHFFFAOYSA-J 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
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- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
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- 229960000195 terbutaline Drugs 0.000 description 1
- 229960000331 teriflunomide Drugs 0.000 description 1
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- UFTNOAOFQCYUAQ-JGCGQSQUSA-N tert-butyl n-[3-[4-[4-[[4-[[(2r)-4-(dimethylamino)-1-phenylsulfanylbutan-2-yl]amino]-3-nitrophenyl]sulfonylcarbamoyl]phenyl]piperazine-1-carbonyl]phenyl]carbamate Chemical compound C([C@@H](CCN(C)C)NC=1C(=CC(=CC=1)S(=O)(=O)NC(=O)C=1C=CC(=CC=1)N1CCN(CC1)C(=O)C=1C=C(NC(=O)OC(C)(C)C)C=CC=1)[N+]([O-])=O)SC1=CC=CC=C1 UFTNOAOFQCYUAQ-JGCGQSQUSA-N 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
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- 230000008733 trauma Effects 0.000 description 1
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- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical class [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
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)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Transplantation (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98847907P | 2007-11-16 | 2007-11-16 | |
| US60/988,479 | 2007-11-16 | ||
| PCT/US2008/083478 WO2009064938A1 (en) | 2007-11-16 | 2008-11-14 | Method of treating arthritis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2705294A1 CA2705294A1 (en) | 2009-05-22 |
| CA2705294C true CA2705294C (en) | 2016-05-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2705294A Expired - Fee Related CA2705294C (en) | 2007-11-16 | 2008-11-14 | Methods of treating arthritis by the administration of substituted benzenesulfonamides |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20090176785A1 (https=) |
| EP (1) | EP2231159A1 (https=) |
| JP (2) | JP5450434B2 (https=) |
| KR (1) | KR101585848B1 (https=) |
| CN (1) | CN101969951B (https=) |
| AU (1) | AU2008322595B2 (https=) |
| CA (1) | CA2705294C (https=) |
| DO (1) | DOP2013000169A (https=) |
| IL (2) | IL205501A (https=) |
| MX (1) | MX2010005395A (https=) |
| NZ (2) | NZ601350A (https=) |
| RU (2) | RU2472509C2 (https=) |
| WO (1) | WO2009064938A1 (https=) |
| ZA (1) | ZA201003434B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100160322A1 (en) | 2008-12-04 | 2010-06-24 | Abbott Laboratories | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| WO2011119345A2 (en) * | 2010-03-25 | 2011-09-29 | Abbott Laboratories | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| TWI520960B (zh) | 2010-05-26 | 2016-02-11 | 艾伯維有限公司 | 用於治療癌症及免疫及自體免疫疾病之細胞凋亡誘導劑 |
| UA113500C2 (xx) | 2010-10-29 | 2017-02-10 | Одержані екструзією розплаву тверді дисперсії, що містять індукуючий апоптоз засіб | |
| CA3152557A1 (en) | 2010-10-29 | 2012-05-03 | Abbvie Inc. | Solid dispersions containing an apoptosis-inducing agent |
| PT2643322T (pt) | 2010-11-23 | 2017-11-13 | Abbvie Inc | Sais e formas cristalinas de um agente indutor de apoptose |
| TWI620736B (zh) | 2010-11-23 | 2018-04-11 | 艾伯維巴哈馬有限公司 | 使用選擇性ｂｃｌ-２抑制劑之治療方法 |
| US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| AU2018322059C1 (en) | 2017-08-23 | 2024-09-12 | Guangzhou Lupeng Pharmaceutical Company Ltd. | BCL-2 inhibitors |
| US12220419B2 (en) | 2018-08-22 | 2025-02-11 | Newave Pharmaceutical Inc. | BCL-2 inhibitors |
| WO2020140005A2 (en) | 2018-12-29 | 2020-07-02 | Newave Pharmaceutical Inc. | Bcl-2 inhibitors |
| WO2021066873A1 (en) | 2019-10-03 | 2021-04-08 | Newave Pharmaceutical Inc. | Condensed heterocycles as bcl-2 inhibitors |
| MX2022005375A (es) | 2019-11-05 | 2022-10-07 | Abbvie Inc | Regímenes de dosificación para usar en el tratamiento de la mielofibrosis y trastornos relacionados con neoplasias mieloproliferativas (nmp) con navitoclax. |
| WO2021133817A1 (en) | 2019-12-27 | 2021-07-01 | Guangzhou Lupeng Pharmaceutical Company Ltd. | 1h-pyrrolo[2,3-b]pyridine derivatives as bcl-2 inhibitors for the treatment of neoplastic and autoimmune diseases |
| KR20220158725A (ko) | 2020-02-24 | 2022-12-01 | 광조우 루펭 파마슈티칼 컴퍼니 엘티디. | Bcl2 억제제를 함유하는 핫 멜트 압출 고체 분산체 |
| WO2022140224A1 (en) | 2020-12-22 | 2022-06-30 | Newave Pharmaceutical Inc. | 1h-pyrrolo[2,3-b]pyridine derivatives as bcl-2 inhibitors for the treatment of neoplastic and autoimmune diseases |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9200275D0 (en) * | 1992-01-08 | 1992-02-26 | Roussel Lab Ltd | Chemical compounds |
| EP0863873B1 (en) * | 1995-10-10 | 1999-11-10 | Pfizer Inc. | Indole carbamates as leukotriene antagonists |
| EP1265864A1 (en) * | 2000-03-21 | 2002-12-18 | The Procter & Gamble Company | Heterocyclic side chain containing, n-substituted metalloprotease inhibitors |
| DE60137273D1 (de) * | 2000-10-20 | 2009-02-12 | Eisai R&D Man Co Ltd | Verfahren zur Herstellung von 4-Phenoxy chinolin Derivaten |
| GB0217431D0 (en) * | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| CN1856490A (zh) * | 2003-07-28 | 2006-11-01 | 詹森药业有限公司 | 苯并咪唑、苯并噻唑和苯并噁唑衍生物及其作为lta4h调节剂的应用 |
| CN1867551B (zh) * | 2003-09-03 | 2013-09-11 | 拉夸里亚创药株式会社 | 作为前列腺素e2拮抗剂的苯基或吡啶基酰胺化合物 |
| WO2005049593A2 (en) * | 2003-11-13 | 2005-06-02 | Abbott Laboratories | N-acylsulfonamide apoptosis promoters |
| ES2257929B1 (es) * | 2004-07-16 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de pirazolina, procedimiento para su obtencion y utilizacion de los mismos como agentes terapeuticos. |
| EP1888550B1 (en) * | 2005-05-12 | 2014-06-25 | AbbVie Bahamas Ltd. | Apoptosis promoters |
| US20060276464A1 (en) * | 2005-05-13 | 2006-12-07 | Wyeth | Diarylsulfone sulfonamides and use thereof |
| WO2008064116A2 (en) * | 2006-11-16 | 2008-05-29 | Abbott Laboratories | Method of preventing or treating organ, hematopoietic stem cell or bone marrow transplant rejection |
-
2008
- 2008-11-14 EP EP08850262A patent/EP2231159A1/en not_active Withdrawn
- 2008-11-14 MX MX2010005395A patent/MX2010005395A/es active IP Right Grant
- 2008-11-14 RU RU2010123796/15A patent/RU2472509C2/ru not_active IP Right Cessation
- 2008-11-14 CA CA2705294A patent/CA2705294C/en not_active Expired - Fee Related
- 2008-11-14 AU AU2008322595A patent/AU2008322595B2/en not_active Ceased
- 2008-11-14 WO PCT/US2008/083478 patent/WO2009064938A1/en not_active Ceased
- 2008-11-14 US US12/270,987 patent/US20090176785A1/en not_active Abandoned
- 2008-11-14 KR KR1020107013163A patent/KR101585848B1/ko not_active Expired - Fee Related
- 2008-11-14 NZ NZ601350A patent/NZ601350A/xx not_active IP Right Cessation
- 2008-11-14 NZ NZ585085A patent/NZ585085A/xx not_active IP Right Cessation
- 2008-11-14 CN CN2008801242231A patent/CN101969951B/zh not_active Expired - Fee Related
- 2008-11-14 RU RU2012143212/15A patent/RU2526201C2/ru not_active IP Right Cessation
- 2008-11-14 JP JP2010534194A patent/JP5450434B2/ja not_active Expired - Fee Related
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2010
- 2010-05-02 IL IL205501A patent/IL205501A/en not_active IP Right Cessation
- 2010-05-14 ZA ZA2010/03434A patent/ZA201003434B/en unknown
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2013
- 2013-07-23 DO DO2013000169A patent/DOP2013000169A/es unknown
- 2013-07-24 IL IL227641A patent/IL227641A0/en unknown
- 2013-11-11 JP JP2013232754A patent/JP5667684B2/ja not_active Expired - Fee Related
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2015
- 2015-12-17 US US14/972,429 patent/US20160101109A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101969951B (zh) | 2012-10-31 |
| KR101585848B1 (ko) | 2016-01-15 |
| AU2008322595A1 (en) | 2009-05-22 |
| MX2010005395A (es) | 2010-06-02 |
| IL205501A0 (en) | 2010-12-30 |
| JP2014065716A (ja) | 2014-04-17 |
| RU2010123796A (ru) | 2011-12-27 |
| CN101969951A (zh) | 2011-02-09 |
| WO2009064938A1 (en) | 2009-05-22 |
| RU2526201C2 (ru) | 2014-08-20 |
| AU2008322595B2 (en) | 2014-01-30 |
| JP5667684B2 (ja) | 2015-02-12 |
| NZ585085A (en) | 2012-08-31 |
| EP2231159A1 (en) | 2010-09-29 |
| RU2012143212A (ru) | 2014-04-20 |
| JP5450434B2 (ja) | 2014-03-26 |
| KR20100099172A (ko) | 2010-09-10 |
| RU2472509C2 (ru) | 2013-01-20 |
| IL205501A (en) | 2013-08-29 |
| DOP2013000169A (es) | 2013-12-15 |
| US20160101109A1 (en) | 2016-04-14 |
| WO2009064938A9 (en) | 2009-08-06 |
| US20090176785A1 (en) | 2009-07-09 |
| CA2705294A1 (en) | 2009-05-22 |
| JP2011503199A (ja) | 2011-01-27 |
| IL227641A0 (en) | 2013-09-30 |
| NZ601350A (en) | 2013-08-30 |
| ZA201003434B (en) | 2011-10-26 |
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