ZA200104507B - Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors. - Google Patents
Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors. Download PDFInfo
- Publication number
- ZA200104507B ZA200104507B ZA200104507A ZA200104507A ZA200104507B ZA 200104507 B ZA200104507 B ZA 200104507B ZA 200104507 A ZA200104507 A ZA 200104507A ZA 200104507 A ZA200104507 A ZA 200104507A ZA 200104507 B ZA200104507 B ZA 200104507B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- carbon atoms
- phenyl
- ynyloxy
- amino
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 12
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title description 9
- 239000002447 tumor necrosis factor alpha converting enzyme inhibitor Substances 0.000 title description 8
- 125000004421 aryl sulphonamide group Chemical group 0.000 title description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 125000001624 naphthyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 10
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- -1 4-cyclobutylamino-but-2-ynyloxy Chemical group 0.000 claims description 7
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- KZNXKMJGYSECTN-UHFFFAOYSA-N 1,2-benzodiazocine Chemical compound N1=NC=CC=CC2=CC=CC=C21 KZNXKMJGYSECTN-UHFFFAOYSA-N 0.000 claims description 4
- FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 claims description 4
- ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical compound O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 claims description 4
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 4
- SFVYUAJWNYVQDB-UHFFFAOYSA-N 2h-1,2-benzoxazocine Chemical compound O1NC=CC=CC2=CC=CC=C21 SFVYUAJWNYVQDB-UHFFFAOYSA-N 0.000 claims description 4
- DTDHRBKRBKFHNH-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2h-1,2-benzothiazocine Chemical group S1NCCCCC2=CC=CC=C21 DTDHRBKRBKFHNH-UHFFFAOYSA-N 0.000 claims description 4
- DMGLUDJTJZXMMG-UHFFFAOYSA-N 3-benzazocine Chemical compound C1=CN=CC=CC2=CC=CC=C21 DMGLUDJTJZXMMG-UHFFFAOYSA-N 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
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- 125000004429 atom Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229940049706 benzodiazepine Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
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- UFJYSWCFYDZPKS-UHFFFAOYSA-N 5-bromo-2-[(4-hept-2-ynoxyphenyl)sulfonyl-methylamino]-n-hydroxy-3-methylbenzamide Chemical compound C1=CC(OCC#CCCCC)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO UFJYSWCFYDZPKS-UHFFFAOYSA-N 0.000 claims description 2
- MDOGBVLWCBWUMC-UHFFFAOYSA-N 5-bromo-2-[(4-hex-2-ynoxyphenyl)sulfonyl-methylamino]-n-hydroxy-3-methylbenzamide Chemical compound C1=CC(OCC#CCCC)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO MDOGBVLWCBWUMC-UHFFFAOYSA-N 0.000 claims description 2
- WZCXPYXIESDPBM-UHFFFAOYSA-N 5-bromo-2-[[4-[4-(diethylamino)but-2-ynoxy]phenyl]sulfonyl-methylamino]-n-hydroxy-3-methylbenzamide Chemical compound C1=CC(OCC#CCN(CC)CC)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO WZCXPYXIESDPBM-UHFFFAOYSA-N 0.000 claims description 2
- VDAJBRAPRPSJQS-UHFFFAOYSA-N 5-bromo-2-[[4-[4-[2-(dimethylamino)ethylamino]but-2-ynoxy]phenyl]sulfonyl-methylamino]-n-hydroxy-3-methylbenzamide Chemical compound C1=CC(OCC#CCNCCN(C)C)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO VDAJBRAPRPSJQS-UHFFFAOYSA-N 0.000 claims description 2
- XDKNQAWYSUZUDU-UHFFFAOYSA-N 5-bromo-2-[[4-[4-[3-(dimethylamino)propylamino]but-2-ynoxy]phenyl]sulfonyl-methylamino]-n-hydroxy-3-methylbenzamide Chemical compound C1=CC(OCC#CCNCCCN(C)C)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO XDKNQAWYSUZUDU-UHFFFAOYSA-N 0.000 claims description 2
- ZEZNNQDUSMNIDE-UHFFFAOYSA-N 5-bromo-n-hydroxy-2-[[4-(4-hydroxybut-2-ynoxy)phenyl]sulfonyl-methylamino]-3-methylbenzamide Chemical compound C=1C=C(OCC#CCO)C=CC=1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO ZEZNNQDUSMNIDE-UHFFFAOYSA-N 0.000 claims description 2
- FODLAGUBVKDEIZ-UHFFFAOYSA-N 5-bromo-n-hydroxy-2-[[4-(4-methoxybut-2-ynoxy)phenyl]sulfonyl-methylamino]-3-methylbenzamide Chemical compound C1=CC(OCC#CCOC)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO FODLAGUBVKDEIZ-UHFFFAOYSA-N 0.000 claims description 2
- DQWZVQLIJHPAAR-UHFFFAOYSA-N 5-bromo-n-hydroxy-2-[[4-[3-(4-methoxyphenyl)prop-2-ynoxy]phenyl]sulfonyl-methylamino]-3-methylbenzamide Chemical compound C1=CC(OC)=CC=C1C#CCOC1=CC=C(S(=O)(=O)N(C)C=2C(=CC(Br)=CC=2C)C(=O)NO)C=C1 DQWZVQLIJHPAAR-UHFFFAOYSA-N 0.000 claims description 2
- BRHXKZALFBLRIF-UHFFFAOYSA-N 5-bromo-n-hydroxy-3-methyl-2-[methyl-(4-pent-2-ynoxyphenyl)sulfonylamino]benzamide Chemical compound C1=CC(OCC#CCC)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO BRHXKZALFBLRIF-UHFFFAOYSA-N 0.000 claims description 2
- JMJKKHVSMQBPSU-UHFFFAOYSA-N 5-bromo-n-hydroxy-3-methyl-2-[methyl-(4-prop-2-ynoxyphenyl)sulfonylamino]benzamide Chemical compound C=1C=C(OCC#C)C=CC=1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO JMJKKHVSMQBPSU-UHFFFAOYSA-N 0.000 claims description 2
- LNMKFTOPZCDAED-UHFFFAOYSA-N 5-bromo-n-hydroxy-3-methyl-2-[methyl-[4-[4-(methylamino)but-2-ynoxy]phenyl]sulfonylamino]benzamide Chemical compound C1=CC(OCC#CCNC)=CC=C1S(=O)(=O)N(C)C1=C(C)C=C(Br)C=C1C(=O)NO LNMKFTOPZCDAED-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- 150000007514 bases Chemical class 0.000 claims description 2
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- 239000000460 chlorine Chemical group 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims 6
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- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- DVZLRKJYASIXFU-UHFFFAOYSA-N 2-[(4-but-2-ynoxyphenyl)sulfonyl-methylamino]-n-hydroxy-3-[(4-methylpiperazin-1-yl)methyl]-5-phenylbenzamide;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCC#CC)=CC=C1S(=O)(=O)N(C)C(C(=CC(=C1)C=2C=CC=CC=2)C(=O)NO)=C1CN1CCN(C)CC1 DVZLRKJYASIXFU-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/36—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- Diabetes (AREA)
- Cardiology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
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- Rheumatology (AREA)
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- Neurosurgery (AREA)
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- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Virology (AREA)
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- Tropical Medicine & Parasitology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23907099A | 1999-01-27 | 1999-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104507B true ZA200104507B (en) | 2002-08-31 |
Family
ID=22900458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104507A ZA200104507B (en) | 1999-01-27 | 2001-05-31 | Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1144369B1 (ja) |
| JP (1) | JP2003524617A (ja) |
| KR (1) | KR20010101733A (ja) |
| CN (1) | CN1376144A (ja) |
| AT (1) | ATE271540T1 (ja) |
| AU (1) | AU769180B2 (ja) |
| BR (1) | BR0007750A (ja) |
| CA (1) | CA2356855A1 (ja) |
| CZ (1) | CZ20012710A3 (ja) |
| DE (1) | DE60012302T2 (ja) |
| DK (1) | DK1144369T3 (ja) |
| EA (1) | EA200100810A1 (ja) |
| ES (1) | ES2225108T3 (ja) |
| HU (1) | HUP0200729A3 (ja) |
| IL (1) | IL144322A0 (ja) |
| NO (1) | NO20013676D0 (ja) |
| PL (1) | PL357647A1 (ja) |
| PT (1) | PT1144369E (ja) |
| WO (1) | WO2000044710A2 (ja) |
| ZA (1) | ZA200104507B (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR022422A1 (es) * | 1999-01-27 | 2002-09-04 | American Cyanamid Co | Inhibidores de tace acetilenicos de acido hidroxamico de heteroarilfulfonamida y amida del acido fosfinico |
| AR027943A1 (es) * | 2000-02-25 | 2003-04-16 | Wyeth Corp | Acidos orto-sulfonamido aril hidroxamicos como inhibidores de metaloproteinasa de matriz y preparacion de los mismos |
| US6465508B1 (en) | 2000-02-25 | 2002-10-15 | Wyeth | Preparation and use of ortho-sulfonamido aryl hydroxamic acids as matrix metalloproteinase inhibitors |
| CA2357110A1 (en) * | 2001-04-11 | 2002-10-11 | American Cyanamid Company | Method for the treatment of polycystic kidney disease |
| US7488754B2 (en) | 2002-04-05 | 2009-02-10 | Wyeth | Method for the treatment of polycystic kidney disease |
| US7199155B2 (en) | 2002-12-23 | 2007-04-03 | Wyeth Holdings Corporation | Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors |
| FR2899895B1 (fr) * | 2006-04-12 | 2010-09-17 | Servier Lab | Nouveaux sels de strontium d'acides sulfoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20210393632A1 (en) | 2018-10-04 | 2021-12-23 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Egfr inhibitors for treating keratodermas |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0925303B1 (en) * | 1996-08-28 | 2002-10-23 | The Procter & Gamble Company | Phosphinic acid amides as matrix metalloprotease inhibitors |
| ATE210637T1 (de) * | 1996-10-16 | 2001-12-15 | American Cyanamid Co | Herstellung und anwendung von ortho-sulfonamido- aryl-hydroxamsäuren als matrix-metalloproteinase- und tace-inhibitoren |
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2000
- 2000-01-27 WO PCT/US2000/002076 patent/WO2000044710A2/en active IP Right Grant
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- 2000-01-27 CA CA002356855A patent/CA2356855A1/en not_active Abandoned
- 2000-01-27 CN CN00810895A patent/CN1376144A/zh active Pending
- 2000-01-27 EA EA200100810A patent/EA200100810A1/ru unknown
- 2000-01-27 DK DK00913270T patent/DK1144369T3/da active
- 2000-01-27 CZ CZ20012710A patent/CZ20012710A3/cs unknown
- 2000-01-27 BR BR0007750-0A patent/BR0007750A/pt not_active IP Right Cessation
- 2000-01-27 KR KR1020017009433A patent/KR20010101733A/ko not_active Application Discontinuation
- 2000-01-27 JP JP2000595967A patent/JP2003524617A/ja active Pending
- 2000-01-27 HU HU0200729A patent/HUP0200729A3/hu unknown
- 2000-01-27 AU AU34744/00A patent/AU769180B2/en not_active Ceased
- 2000-01-27 DE DE60012302T patent/DE60012302T2/de not_active Expired - Fee Related
- 2000-01-27 ES ES00913270T patent/ES2225108T3/es not_active Expired - Lifetime
- 2000-01-27 PL PL00357647A patent/PL357647A1/xx not_active Application Discontinuation
- 2000-01-27 EP EP00913270A patent/EP1144369B1/en not_active Expired - Lifetime
-
2001
- 2001-05-31 ZA ZA200104507A patent/ZA200104507B/en unknown
- 2001-07-26 NO NO20013676A patent/NO20013676D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK1144369T3 (da) | 2004-11-01 |
| AU3474400A (en) | 2000-08-18 |
| HUP0200729A3 (en) | 2005-04-28 |
| NO20013676D0 (no) | 2001-07-26 |
| DE60012302D1 (en) | 2004-08-26 |
| ES2225108T3 (es) | 2005-03-16 |
| CZ20012710A3 (cs) | 2002-04-17 |
| EA200100810A1 (ru) | 2002-02-28 |
| KR20010101733A (ko) | 2001-11-14 |
| WO2000044710A3 (en) | 2000-12-21 |
| CN1376144A (zh) | 2002-10-23 |
| PL357647A1 (en) | 2004-07-26 |
| BR0007750A (pt) | 2001-10-30 |
| HUP0200729A2 (hu) | 2002-07-29 |
| ATE271540T1 (de) | 2004-08-15 |
| AU769180B2 (en) | 2004-01-15 |
| EP1144369A2 (en) | 2001-10-17 |
| DE60012302T2 (de) | 2005-08-04 |
| IL144322A0 (en) | 2002-05-23 |
| JP2003524617A (ja) | 2003-08-19 |
| CA2356855A1 (en) | 2000-08-03 |
| WO2000044710A2 (en) | 2000-08-03 |
| PT1144369E (pt) | 2004-11-30 |
| EP1144369B1 (en) | 2004-07-21 |
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