CA2443721A1 - Sulfonamide derivatives - Google Patents
Sulfonamide derivatives Download PDFInfo
- Publication number
- CA2443721A1 CA2443721A1 CA002443721A CA2443721A CA2443721A1 CA 2443721 A1 CA2443721 A1 CA 2443721A1 CA 002443721 A CA002443721 A CA 002443721A CA 2443721 A CA2443721 A CA 2443721A CA 2443721 A1 CA2443721 A1 CA 2443721A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- c4alkyl
- triazol
- hydrogen
- 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
- 229940124530 sulfonamide Drugs 0.000 title abstract description 4
- 150000003456 sulfonamides Chemical class 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 8
- 230000004913 activation Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 102000017916 BDKRB1 Human genes 0.000 claims abstract description 4
- 108010044231 Bradykinin B1 Receptor Proteins 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 21
- -1 1,2-dichlorophenyl Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 6
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 229940088679 drug related substance Drugs 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 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 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 5
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 3
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 27
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 101800004538 Bradykinin Proteins 0.000 description 7
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 7
- 102100035792 Kininogen-1 Human genes 0.000 description 7
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
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- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- 108010003195 Kallidin Proteins 0.000 description 5
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- OECYEHWJPRPCOH-UHFFFAOYSA-N 4-bromo-2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Br)=CC=C1S(Cl)(=O)=O OECYEHWJPRPCOH-UHFFFAOYSA-N 0.000 description 2
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29082701P | 2001-05-14 | 2001-05-14 | |
| US60/290,827 | 2001-05-14 | ||
| PCT/EP2002/005240 WO2002092556A1 (en) | 2001-05-14 | 2002-05-13 | Sulfonamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2443721A1 true CA2443721A1 (en) | 2002-11-21 |
Family
ID=23117717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002443721A Abandoned CA2443721A1 (en) | 2001-05-14 | 2002-05-13 | Sulfonamide derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7109203B2 (enExample) |
| EP (1) | EP1389183B1 (enExample) |
| JP (1) | JP4150597B2 (enExample) |
| CN (1) | CN1268610C (enExample) |
| AR (1) | AR035891A1 (enExample) |
| AT (1) | ATE459598T1 (enExample) |
| BR (1) | BR0209386A (enExample) |
| CA (1) | CA2443721A1 (enExample) |
| DE (1) | DE60235536D1 (enExample) |
| ES (1) | ES2340664T3 (enExample) |
| PE (1) | PE20021158A1 (enExample) |
| PT (1) | PT1389183E (enExample) |
| WO (1) | WO2002092556A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214807B1 (en) * | 1999-06-22 | 2001-04-10 | Cv Therapeutics, Inc. | C-pyrazole 2A A receptor agonists |
| USRE47351E1 (en) | 1999-06-22 | 2019-04-16 | Gilead Sciences, Inc. | 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists |
| US6403567B1 (en) * | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| CA2671940A1 (en) | 2000-02-23 | 2001-08-30 | Cv Therapeutics, Inc. | Identification of partial agonists of the a2a adenosine receptor |
| WO2004011010A1 (en) * | 2002-07-29 | 2004-02-05 | Cv Therapeutics, Inc. | Myocardial perfusion imaging using a2a receptor agonists |
| US8470801B2 (en) | 2002-07-29 | 2013-06-25 | Gilead Sciences, Inc. | Myocardial perfusion imaging methods and compositions |
| US20050020915A1 (en) * | 2002-07-29 | 2005-01-27 | Cv Therapeutics, Inc. | Myocardial perfusion imaging methods and compositions |
| CA2509881A1 (en) * | 2002-12-19 | 2004-07-08 | Elan Pharmaceuticals, Inc. | Substituted n-phenyl sulfonamide bradykinin antagonists |
| EP1802317A2 (en) * | 2004-10-20 | 2007-07-04 | Cv Therapeutics, Inc. | Use of a2a adenosine receptor agonists |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| CA2640089C (en) | 2006-02-03 | 2013-07-23 | Cv Therapeutics, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| CA2655310A1 (en) * | 2006-06-22 | 2008-05-29 | Cv Therapeutics, Inc. | Use of a2a adenosine receptor agonists in the treatment of ischemia |
| US20090081120A1 (en) * | 2006-09-01 | 2009-03-26 | Cv Therapeutics, Inc. | Methods and Compositions for Increasing Patient Tolerability During Myocardial Imaging Methods |
| MX2009002299A (es) * | 2006-09-01 | 2009-03-20 | Cv Therapeutics Inc | Metodos y composiciones para incrementar la tolerancia del paciente durante metodos de formacion de imagenes del miocardio. |
| WO2008042796A2 (en) * | 2006-09-29 | 2008-04-10 | Cv Therapeutics, Inc. | Methods for myocardial imaging in patients having a history of pulmonary disease |
| EP2099360A2 (en) * | 2007-01-03 | 2009-09-16 | CV Therapeutics Inc. | Myocardial perfusion imaging |
| ES2524259T3 (es) * | 2008-03-24 | 2014-12-04 | Novartis Ag | Inhibidores de metaloproteinasa de matriz a base de arilsulfonamida |
| KR20110063556A (ko) * | 2008-09-29 | 2011-06-10 | 길리애드 사이언시즈, 인코포레이티드 | 다검출 전산화 단층 촬영법에 사용하기 위한 ａ-２-알파 수용체 길항제와 속도 조절제의 조합물 |
| EP2316820A1 (en) | 2009-10-28 | 2011-05-04 | Dompe S.p.A. | 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| WO2013164790A1 (en) | 2012-05-03 | 2013-11-07 | Novartis Ag | L-malate salt of 2, 7 - diaza - spiro [4.5 ] dec- 7 - yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
| PT2813502T (pt) | 2013-06-14 | 2017-04-06 | Dompé Farm S P A | Antagonistas do recetor da bradicinina e composições farmacêuticas que os contêm |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE120047C (enExample) * | ||||
| FR2743562B1 (fr) * | 1996-01-11 | 1998-04-03 | Sanofi Sa | Derives de n-(arylsulfonyl) aminoacides, leur preparation, les compositions pharmaceutiques en contenant |
| WO2001024786A1 (en) * | 1999-05-13 | 2001-04-12 | Shionogi & Co., Ltd. | Preventive or therapeutic drugs for diabetes |
| GB9913079D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
-
2002
- 2002-05-13 EP EP02742997A patent/EP1389183B1/en not_active Expired - Lifetime
- 2002-05-13 DE DE60235536T patent/DE60235536D1/de not_active Expired - Fee Related
- 2002-05-13 ES ES02742997T patent/ES2340664T3/es not_active Expired - Lifetime
- 2002-05-13 WO PCT/EP2002/005240 patent/WO2002092556A1/en not_active Ceased
- 2002-05-13 PT PT02742997T patent/PT1389183E/pt unknown
- 2002-05-13 AT AT02742997T patent/ATE459598T1/de not_active IP Right Cessation
- 2002-05-13 CA CA002443721A patent/CA2443721A1/en not_active Abandoned
- 2002-05-13 CN CNB028098900A patent/CN1268610C/zh not_active Expired - Fee Related
- 2002-05-13 BR BR0209386-3A patent/BR0209386A/pt not_active IP Right Cessation
- 2002-05-13 AR ARP020101737A patent/AR035891A1/es unknown
- 2002-05-13 JP JP2002589442A patent/JP4150597B2/ja not_active Expired - Fee Related
- 2002-05-13 US US10/475,420 patent/US7109203B2/en not_active Expired - Fee Related
- 2002-05-14 PE PE2002000401A patent/PE20021158A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE459598T1 (de) | 2010-03-15 |
| JP2004528385A (ja) | 2004-09-16 |
| CN1268610C (zh) | 2006-08-09 |
| US20040127533A1 (en) | 2004-07-01 |
| DE60235536D1 (de) | 2010-04-15 |
| EP1389183B1 (en) | 2010-03-03 |
| WO2002092556A1 (en) | 2002-11-21 |
| PE20021158A1 (es) | 2003-03-03 |
| JP4150597B2 (ja) | 2008-09-17 |
| CN1509269A (zh) | 2004-06-30 |
| US7109203B2 (en) | 2006-09-19 |
| EP1389183A1 (en) | 2004-02-18 |
| BR0209386A (pt) | 2004-07-06 |
| ES2340664T3 (es) | 2010-06-08 |
| PT1389183E (pt) | 2010-04-26 |
| AR035891A1 (es) | 2004-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |