ZA200105130B - Bis-sulfonamides. - Google Patents
Bis-sulfonamides. Download PDFInfo
- Publication number
- ZA200105130B ZA200105130B ZA200105130A ZA200105130A ZA200105130B ZA 200105130 B ZA200105130 B ZA 200105130B ZA 200105130 A ZA200105130 A ZA 200105130A ZA 200105130 A ZA200105130 A ZA 200105130A ZA 200105130 B ZA200105130 B ZA 200105130B
- Authority
- ZA
- South Africa
- Prior art keywords
- lower alkyl
- formula
- compounds
- sulfonamide
- pyrimidinyl
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 108050009340 Endothelin Proteins 0.000 claims description 25
- 102000002045 Endothelin Human genes 0.000 claims description 25
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 15
- -1 tri-substituted phenyl Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 208000035475 disorder Diseases 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 19
- 239000000203 mixture Substances 0.000 claims 16
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims 7
- 230000000903 blocking effect Effects 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 206010002383 Angina Pectoris Diseases 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 206010047163 Vasospasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 230000002062 proliferating effect Effects 0.000 claims 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000012876 carrier material Substances 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- GAZVSNAEUUUDEK-JDSLSITLSA-N [(1r,3r,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-hydroxybenzoate Chemical compound O([C@H]1[C@@]2(C)CC[C@H](C1)C2(C)C)C(=O)C1=CC=CC=C1O GAZVSNAEUUUDEK-JDSLSITLSA-N 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- GWBCKOWLDKFIHO-UHFFFAOYSA-N n-[2-cyclopropyl-6-[2-(ethylsulfonylamino)ethoxy]-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound C=1C=CC=C(OC)C=1OC=1C(OCCNS(=O)(=O)CC)=NC(C2CC2)=NC=1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 GWBCKOWLDKFIHO-UHFFFAOYSA-N 0.000 claims 1
- BCRJIIJVFJJYRD-UHFFFAOYSA-N n-[3-[6-[(4-tert-butylphenyl)sulfonylamino]-2-cyclopropyl-5-(2-methoxyphenoxy)pyrimidin-4-yl]oxypropyl]thiophene-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C2CC2)OCCCNS(=O)(=O)C=2SC=CC=2)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 BCRJIIJVFJJYRD-UHFFFAOYSA-N 0.000 claims 1
- HDWHUKBOFNHSSO-UHFFFAOYSA-N n-[3-[6-[(4-tert-butylphenyl)sulfonylamino]-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]oxypropyl]thiophene-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCCNS(=O)(=O)C=2SC=CC=2)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HDWHUKBOFNHSSO-UHFFFAOYSA-N 0.000 claims 1
- ZLBPWBIGJXVCIO-UHFFFAOYSA-N n-[6-chloro-2-cyclopropyl-5-(2-methoxyphenoxy)pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC1=C(Cl)N=C(C2CC2)N=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 ZLBPWBIGJXVCIO-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108700021343 poly-beta-(N-acetyl-D-glucosaminyl)-poly-D-lysine Proteins 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- 101800004490 Endothelin-1 Proteins 0.000 description 10
- 102400000686 Endothelin-1 Human genes 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 230000027455 binding Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
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- 230000002401 inhibitory effect Effects 0.000 description 4
- 229940118365 Endothelin receptor antagonist Drugs 0.000 description 3
- 206010019280 Heart failures Diseases 0.000 description 3
- 208000001647 Renal Insufficiency Diseases 0.000 description 3
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 3
- 239000002308 endothelin receptor antagonist Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 201000006370 kidney failure Diseases 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- 102000010180 Endothelin receptor Human genes 0.000 description 2
- 108050001739 Endothelin receptor Proteins 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
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- 210000004027 cell Anatomy 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 208000002815 pulmonary hypertension Diseases 0.000 description 2
- LXPHPKVWHQLBBA-UHFFFAOYSA-N sarafotoxin s6c Chemical compound C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(C(C)CC)NC(=O)C(C(C)C)NC(=O)C(CC(O)=O)NC(=O)C(CCC(N)=O)NC(=O)C(NC(=O)C1NC(=O)C(CC=2C=CC=CC=2)NC(=O)C(CC(N)=O)NC(=O)C(CC(C)C)NC(=O)C2CSSCC(C(NC(CC(N)=O)C(=O)NC(CC(O)=O)C(=O)NC(CCSC)C(=O)NC(C(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(=O)NC(CCC(O)=O)C(=O)N2)C(C)O)=O)NC(=O)C(C(C)O)NC(=O)C(N)CSSC1)CC1=CN=CN1 LXPHPKVWHQLBBA-UHFFFAOYSA-N 0.000 description 2
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
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- 206010016654 Fibrosis Diseases 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- 239000007836 KH2PO4 Substances 0.000 description 1
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- 101710205037 Sarafotoxin Proteins 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
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- 229960001123 epoprostenol Drugs 0.000 description 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 208000007232 portal hypertension Diseases 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
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Classifications
-
- 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
- C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Glass Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP9906485 | 1999-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200105130B true ZA200105130B (en) | 2002-09-23 |
Family
ID=8167417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105130A ZA200105130B (en) | 1999-09-03 | 2001-06-21 | Bis-sulfonamides. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6596719B1 (zh) |
| EP (1) | EP1137642B1 (zh) |
| CN (1) | CN100424079C (zh) |
| AT (1) | ATE380180T1 (zh) |
| AU (1) | AU775194B2 (zh) |
| CA (1) | CA2361402C (zh) |
| DE (1) | DE60037308T2 (zh) |
| ES (1) | ES2295048T3 (zh) |
| HU (1) | HUP0201402A3 (zh) |
| IL (1) | IL143935A (zh) |
| NO (1) | NO20013586L (zh) |
| NZ (1) | NZ512526A (zh) |
| WO (1) | WO2001017976A1 (zh) |
| ZA (1) | ZA200105130B (zh) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6720322B2 (en) * | 1999-12-22 | 2004-04-13 | Actelion Pharamceuticals Ltd. | Butyne diol derivatives |
| AU2001241512A1 (en) * | 2000-03-13 | 2001-09-24 | Eli Lilly And Company | Sulfonamide derivatives |
| US6387915B2 (en) | 2000-05-31 | 2002-05-14 | Pfizer Inc. | Isoxazole-sulfonamide endothelin antagonists |
| BRPI0116237B8 (pt) | 2000-12-18 | 2021-05-25 | Actelion Pharmaceuticals Ltd | "composto de sulfamida, composição farmacêutica contendo o mesmo e seu uso como medicamento antagonista de receptor de endotelina". |
| ES2262567T3 (es) | 2001-03-20 | 2006-12-01 | Schwarz Pharma Ag | Nuevo uso de una clase peptidica de compuesto para tratamiento del dolor inflamatorio no neuropatico. |
| DK1243263T3 (da) | 2001-03-21 | 2003-03-17 | Sanol Arznei Schwarz Gmbh | Hidtil ukendt anvendelse af en klasse af peptidforbindelser til behandling af allodyni eller andre forskellige typer af kronisk- eller fantomsmerte |
| ES2297040T3 (es) | 2002-01-02 | 2008-05-01 | Actelion Pharmaceuticals Ltd. | Nuevas alcanosulfonamidas como antagonistas endoteliales. |
| AU2004294714B2 (en) | 2003-12-02 | 2009-12-10 | Ucb Pharma Gmbh | Novel use of peptide compounds for treating central neuropathic pain |
| EP1725540B1 (en) | 2004-03-05 | 2012-09-12 | F.Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 antagonists |
| EA013591B1 (ru) | 2004-04-16 | 2010-06-30 | Шварц Фарма Аг | Применение пептидных соединений для профилактики, облегчения и лечения головной боли и болезненных состояний, связанных с или вызванных распространяющейся кортикальной депрессией (csd) |
| EP1604655A1 (en) | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating pain in trigeminal neuralgia |
| EP1781276B1 (en) | 2004-08-27 | 2010-06-23 | UCB Pharma GmbH | Use of peptide compounds for treating bone cancer pain, chemotherapy- and nucleoside-induced pain |
| ES2601178T3 (es) | 2005-09-01 | 2017-02-14 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como moduladores de P2X3 y P3X2/3 |
| CN101296907B (zh) | 2005-09-01 | 2013-03-27 | 弗·哈夫曼-拉罗切有限公司 | 作为p2x3和p2x2/3调节剂的二氨基嘧啶类 |
| CA2620129C (en) | 2005-09-01 | 2014-12-23 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| AR061476A1 (es) | 2006-06-15 | 2008-08-27 | Sanol Arznei Schwarz Gmbh | Composicion farmaceutica con efecto anticonvulsivo sinergico |
| AR062501A1 (es) | 2006-08-29 | 2008-11-12 | Actelion Pharmaceuticals Ltd | Composiciones terapeuticas |
| MX2010001837A (es) | 2007-08-17 | 2010-03-10 | Actelion Pharmaceuticals Ltd | Derivados de 4-pirimidinasulfamida. |
| CN101279948B (zh) * | 2008-03-14 | 2010-08-11 | 苏州博鸿化工技术有限公司 | 4,6-二氯-5-(2-甲氧基苯氧基)-2,2'-二嘧啶的合成方法 |
| CN111407767B (zh) * | 2020-03-28 | 2021-05-25 | 中山大学 | 一种磺胺间甲氧嘧啶衍生物在制备抗肿瘤药物中的应用 |
| CN112778215B (zh) * | 2021-01-29 | 2023-06-20 | 中国医科大学 | 2-甲氧基苯氧基嘧啶类抗肿瘤化合物及其制备方法和应用 |
| CN112898208B (zh) * | 2021-01-29 | 2023-06-20 | 中国医科大学 | 苯基嘧啶胺类抗肿瘤化合物及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7310889A (zh) * | 1972-08-12 | 1974-02-14 | ||
| CA2162630C (en) | 1994-11-25 | 2007-05-01 | Volker Breu | Sulfonamides |
| TW313568B (zh) | 1994-12-20 | 1997-08-21 | Hoffmann La Roche | |
| US5739333A (en) * | 1995-05-16 | 1998-04-14 | Tanabe Seiyaku Co., Ltd. | Sulfonamide derivative and process for preparing the same |
| US5939446A (en) * | 1996-04-09 | 1999-08-17 | Bristol-Myers Squibb Co. | Heteroaryl substituted phenyl isoxazole sulfonamide endothelin antagonists |
-
2000
- 2000-08-16 ES ES00956456T patent/ES2295048T3/es not_active Expired - Lifetime
- 2000-08-16 WO PCT/EP2000/007999 patent/WO2001017976A1/en active IP Right Grant
- 2000-08-16 US US10/031,555 patent/US6596719B1/en not_active Expired - Fee Related
- 2000-08-16 CN CN00802515.0A patent/CN100424079C/zh not_active Expired - Fee Related
- 2000-08-16 EP EP00956456A patent/EP1137642B1/en not_active Expired - Lifetime
- 2000-08-16 CA CA002361402A patent/CA2361402C/en not_active Expired - Fee Related
- 2000-08-16 HU HU0201402A patent/HUP0201402A3/hu unknown
- 2000-08-16 DE DE60037308T patent/DE60037308T2/de not_active Expired - Lifetime
- 2000-08-16 IL IL14393500A patent/IL143935A/xx not_active IP Right Cessation
- 2000-08-16 AT AT00956456T patent/ATE380180T1/de not_active IP Right Cessation
- 2000-08-16 AU AU68391/00A patent/AU775194B2/en not_active Ceased
- 2000-08-16 NZ NZ512526A patent/NZ512526A/xx active Application Filing
-
2001
- 2001-06-21 ZA ZA200105130A patent/ZA200105130B/en unknown
- 2001-07-20 NO NO20013586A patent/NO20013586L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60037308D1 (de) | 2008-01-17 |
| AU775194B2 (en) | 2004-07-22 |
| IL143935A (en) | 2005-08-31 |
| EP1137642B1 (en) | 2007-12-05 |
| DE60037308T2 (de) | 2008-10-30 |
| IL143935A0 (en) | 2002-04-21 |
| AU6839100A (en) | 2001-04-10 |
| ATE380180T1 (de) | 2007-12-15 |
| CA2361402C (en) | 2009-05-12 |
| CA2361402A1 (en) | 2001-03-15 |
| EP1137642A1 (en) | 2001-10-04 |
| CN1335839A (zh) | 2002-02-13 |
| HUP0201402A3 (en) | 2003-12-29 |
| CN100424079C (zh) | 2008-10-08 |
| US6596719B1 (en) | 2003-07-22 |
| HUP0201402A2 (en) | 2002-08-28 |
| NO20013586D0 (no) | 2001-07-20 |
| NZ512526A (en) | 2004-01-30 |
| ES2295048T3 (es) | 2008-04-16 |
| NO20013586L (no) | 2001-07-20 |
| WO2001017976A1 (en) | 2001-03-15 |
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