NO332782B1 - Sulfonsyrer og derivater derav, samt fremstilling og anvendelse derav og farmasoytiske preparater omfattende nevnte sulfonsyrer - Google Patents
Sulfonsyrer og derivater derav, samt fremstilling og anvendelse derav og farmasoytiske preparater omfattende nevnte sulfonsyrer Download PDFInfo
- Publication number
- NO332782B1 NO332782B1 NO20054672A NO20054672A NO332782B1 NO 332782 B1 NO332782 B1 NO 332782B1 NO 20054672 A NO20054672 A NO 20054672A NO 20054672 A NO20054672 A NO 20054672A NO 332782 B1 NO332782 B1 NO 332782B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- sulfonamide
- ethene
- ethane
- isobutylphenyl
- Prior art date
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- 150000003460 sulfonic acids Chemical class 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
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- 108090001007 Interleukin-8 Proteins 0.000 claims abstract description 33
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- 201000001441 melanoma Diseases 0.000 claims abstract description 8
- 230000010410 reperfusion Effects 0.000 claims abstract description 8
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 7
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 7
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 7
- 230000004761 fibrosis Effects 0.000 claims abstract description 7
- 208000028867 ischemia Diseases 0.000 claims abstract description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 6
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 150000003456 sulfonamides Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 38
- -1 phenylsulfonyloxy Chemical group 0.000 claims description 18
- 230000035605 chemotaxis Effects 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
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- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- 229910003827 NRaRb Inorganic materials 0.000 claims description 6
- 241000721454 Pemphigus Species 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical group C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
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- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims description 2
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
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- AXVJHGYYZMJVTG-VAWYXSNFSA-N (e)-2-(3-benzoylphenyl)prop-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)\C=C(/C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 AXVJHGYYZMJVTG-VAWYXSNFSA-N 0.000 claims description 2
- UUZWUEBXQIRVIJ-CSKARUKUSA-N (e)-2-(3-propan-2-ylphenyl)prop-1-ene-1-sulfonamide Chemical compound CC(C)C1=CC=CC(C(\C)=C\S(N)(=O)=O)=C1 UUZWUEBXQIRVIJ-CSKARUKUSA-N 0.000 claims description 2
- QQWFZCCLAXTVHT-BQYQJAHWSA-N (e)-2-[4-(2-methylpropyl)phenyl]ethenesulfonic acid Chemical compound CC(C)CC1=CC=C(\C=C\S(O)(=O)=O)C=C1 QQWFZCCLAXTVHT-BQYQJAHWSA-N 0.000 claims description 2
- BUMBAHZDEXELLT-PKNBQFBNSA-N (e)-2-[4-(2-methylpropyl)phenyl]prop-1-ene-1-sulfonamide Chemical compound CC(C)CC1=CC=C(C(\C)=C\S(N)(=O)=O)C=C1 BUMBAHZDEXELLT-PKNBQFBNSA-N 0.000 claims description 2
- HUJOGKRKERYRRY-UHFFFAOYSA-N 2-(3-benzoylphenyl)ethanesulfonic acid Chemical compound OS(=O)(=O)CCC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 HUJOGKRKERYRRY-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
- YMOGDLNYXPGMBS-VOTSOKGWSA-N (e)-2-[4-(methanesulfonamido)phenyl]ethenesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(\C=C\S(N)(=O)=O)C=C1 YMOGDLNYXPGMBS-VOTSOKGWSA-N 0.000 claims 1
- BFFIVHMCADCVMV-VOTSOKGWSA-N (e)-2-[4-(methanesulfonamido)phenyl]ethenesulfonic acid Chemical compound CS(=O)(=O)NC1=CC=C(\C=C\S(O)(=O)=O)C=C1 BFFIVHMCADCVMV-VOTSOKGWSA-N 0.000 claims 1
- LMXBZKBMNSXXQO-AATRIKPKSA-N (e)-2-[4-(trifluoromethylsulfonyloxy)phenyl]ethenesulfonic acid Chemical compound OS(=O)(=O)\C=C\C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1 LMXBZKBMNSXXQO-AATRIKPKSA-N 0.000 claims 1
- FQRKUFZDUHPGER-AATRIKPKSA-N [4-[(e)-2-sulfamoylethenyl]phenyl] trifluoromethanesulfonate Chemical compound NS(=O)(=O)\C=C\C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1 FQRKUFZDUHPGER-AATRIKPKSA-N 0.000 claims 1
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 abstract description 31
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- 238000002474 experimental method Methods 0.000 description 8
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/24—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/27—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/31—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/35—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP03005783A EP1457485A1 (en) | 2003-03-14 | 2003-03-14 | Sulfonic acids, their derivatives and pharmaceutical compositions containing them |
PCT/EP2004/050293 WO2004080951A2 (en) | 2003-03-14 | 2004-03-11 | Sulfonic acids, their derivatives and pharmaceutical compositions containing them |
Publications (3)
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NO20054672D0 NO20054672D0 (no) | 2005-10-11 |
NO20054672L NO20054672L (no) | 2005-12-13 |
NO332782B1 true NO332782B1 (no) | 2013-01-14 |
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NO20054672A NO332782B1 (no) | 2003-03-14 | 2005-10-11 | Sulfonsyrer og derivater derav, samt fremstilling og anvendelse derav og farmasoytiske preparater omfattende nevnte sulfonsyrer |
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Country | Link |
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US (1) | US7737139B2 (pt) |
EP (2) | EP1457485A1 (pt) |
JP (1) | JP4578466B2 (pt) |
CN (1) | CN100372831C (pt) |
AT (1) | ATE547397T1 (pt) |
AU (1) | AU2004220360B2 (pt) |
CA (1) | CA2514988C (pt) |
DK (1) | DK1606248T3 (pt) |
ES (1) | ES2386811T3 (pt) |
HK (1) | HK1089431A1 (pt) |
NO (1) | NO332782B1 (pt) |
PT (1) | PT1606248E (pt) |
RU (1) | RU2345063C2 (pt) |
WO (1) | WO2004080951A2 (pt) |
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US7504401B2 (en) | 2003-08-29 | 2009-03-17 | Locus Pharmaceuticals, Inc. | Anti-cancer agents and uses thereof |
US20070149618A1 (en) | 2004-02-17 | 2007-06-28 | Action Medicines, S.L. | Methods of use for 2,5-dihydroxybenzene sulfonic acid compounds for the treatment of cancer, rosacea and psoriasis |
US20080125485A1 (en) | 2004-02-17 | 2008-05-29 | Action Medicines | Use of 2,5-Dihydroxybenzene Derivatives for Treating Actinic Keratosis |
ES2238924B1 (es) | 2004-02-17 | 2006-12-01 | Investread Europa, S.L. | Uso del acido 2,5-dihidroxibencenosulfonico, en la fabricacion de medicamentos de aplicacion en el tratamiento de enfermedades angiodependientes. |
BRPI0511834A (pt) | 2004-07-14 | 2008-01-08 | Ptc Therapeutics Inc | métodos por tratar hepatite c |
US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
MX2007000762A (es) | 2004-07-22 | 2007-04-02 | Ptc Therapeutics Inc | Tienopiridinas para tratamientode hepatitis c. |
TWI331523B (en) * | 2005-12-08 | 2010-10-11 | Nat Health Research Institutes | Vinylsulfonate compounds |
ES2433095T3 (es) * | 2006-05-18 | 2013-12-09 | Dompe' S.P.A. | (2R)-2[(4-Sulfonil)aminofenil]propanamidas y composiciones farmacéuticas que las contienen |
US8101660B2 (en) * | 2006-08-16 | 2012-01-24 | AmDerma Pharmaceuticals, LLC | Use of 2,5-dihydroxybenzene compounds and derivatives for the treatment of skin cancer |
PT2054051E (pt) | 2006-08-16 | 2013-04-03 | Amderma Pharmaceuticals Llc | Utilização de derivados 2,5-di-hidroxibenzeno para tratar ceratose actínica |
WO2009020579A1 (en) * | 2007-08-07 | 2009-02-12 | Schering Corporation | Gamma secretase modulators |
CN103159674A (zh) * | 2013-04-03 | 2013-06-19 | 苏州安诺生物医药技术有限公司 | 2-苯烷酰胺类化合物及其制备方法、药物组合物和用途 |
RU2699034C1 (ru) * | 2016-02-16 | 2019-09-03 | ЗОИТИС СЕРВИСЕЗ ЭлЭлСи | Способ получения соединений 7H-пирроло[2,3-d]пиримидина |
CN111747838B (zh) * | 2020-07-29 | 2023-04-07 | 深圳大学 | 一种电催化合成氘代布洛芬的方法 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL33051A (en) | 1968-10-11 | 1974-05-16 | Ciba Geigy Ag | Alpha-cycloalkenyl-phenyl-fatty acid derivatives and process for their manufacture |
JPS4918875A (pt) | 1972-06-17 | 1974-02-19 | ||
FR2233988A1 (pt) * | 1973-06-11 | 1975-01-17 | Bristol Myers Co | |
JPS5277030A (en) * | 1975-12-23 | 1977-06-29 | Toyo Pharma Kk | Production of novel benzyl sulphonic acid derivatives |
IT1193955B (it) | 1980-07-22 | 1988-08-31 | Real Di Alberto Reiner S A S | Derivati ammidici dell'acido p-isobutilfenilpropionico, procedimento per la loro preparazione e relative composizioni farmaceutici |
US5216026A (en) * | 1990-07-17 | 1993-06-01 | Eli Lilly And Company | Antitumor compositions and methods of treatment |
MX9702734A (es) * | 1994-10-13 | 1997-06-28 | Pfizer | Benzopirano y compuestos benzocondensados, su preparacion y su uso como antagonistas de leucotrieno b4 (ltb4). |
EP0809492A4 (en) * | 1995-02-17 | 2007-01-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
US6262113B1 (en) * | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
US6410584B1 (en) * | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
IT1298214B1 (it) * | 1998-01-28 | 1999-12-20 | Dompe Spa | Sali dell'acido (r) 2-(3-benzoilfenil) propionico e loro composizioni farmaceutiche. |
IT1303249B1 (it) * | 1998-10-23 | 2000-11-06 | Dompe Spa | Alcune n-(2-aril-propionil)-solfonammidi e preparazionifarmaceutiche che le contengono. |
US6348032B1 (en) * | 1998-11-23 | 2002-02-19 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with benzimidazole derivatives |
PE20001566A1 (es) * | 1999-03-26 | 2001-02-05 | Ucb Sa | Piperazinas 1,4-sustituidas, piperidinas 1,4-sustituidas y 4-alquilidenilpiperidinas 1-sustituidas |
WO2001040262A1 (en) * | 1999-12-03 | 2001-06-07 | Bristol-Myers Squibb Pharma Company | Alpha-ketoamide inhibitors of hepatitis c virus ns3 protease |
IT1317826B1 (it) * | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
IT1318466B1 (it) | 2000-04-14 | 2003-08-25 | Dompe Spa | Ammidi di acidi r-2-(amminoaril)-propionici, utili nella prevenzionedell'attivazione leucocitaria. |
ITMI20010395A1 (it) * | 2001-02-27 | 2002-08-27 | Dompe Spa | Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate |
ITMI20012025A1 (it) * | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
ITMI20012434A1 (it) * | 2001-11-20 | 2003-05-20 | Dompe Spa | Acidi 2-aril-propionici e composizioni farmaceutiche che li contengono |
-
2003
- 2003-03-14 EP EP03005783A patent/EP1457485A1/en not_active Withdrawn
-
2004
- 2004-03-11 ES ES04719463T patent/ES2386811T3/es not_active Expired - Lifetime
- 2004-03-11 CN CNB2004800068672A patent/CN100372831C/zh not_active Expired - Fee Related
- 2004-03-11 AT AT04719463T patent/ATE547397T1/de active
- 2004-03-11 AU AU2004220360A patent/AU2004220360B2/en not_active Ceased
- 2004-03-11 PT PT04719463T patent/PT1606248E/pt unknown
- 2004-03-11 DK DK04719463.4T patent/DK1606248T3/da active
- 2004-03-11 EP EP04719463A patent/EP1606248B1/en not_active Expired - Lifetime
- 2004-03-11 WO PCT/EP2004/050293 patent/WO2004080951A2/en active Application Filing
- 2004-03-11 CA CA2514988A patent/CA2514988C/en not_active Expired - Fee Related
- 2004-03-11 US US10/544,396 patent/US7737139B2/en not_active Expired - Fee Related
- 2004-03-11 RU RU2005131846/04A patent/RU2345063C2/ru not_active IP Right Cessation
- 2004-03-11 JP JP2006505463A patent/JP4578466B2/ja not_active Expired - Fee Related
-
2005
- 2005-10-11 NO NO20054672A patent/NO332782B1/no not_active IP Right Cessation
-
2006
- 2006-10-13 HK HK06111286A patent/HK1089431A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP4578466B2 (ja) | 2010-11-10 |
US7737139B2 (en) | 2010-06-15 |
DK1606248T3 (da) | 2012-06-18 |
CN1761645A (zh) | 2006-04-19 |
NO20054672L (no) | 2005-12-13 |
EP1457485A1 (en) | 2004-09-15 |
RU2345063C2 (ru) | 2009-01-27 |
CA2514988C (en) | 2013-07-16 |
WO2004080951A3 (en) | 2004-11-04 |
PT1606248E (pt) | 2012-06-01 |
AU2004220360B2 (en) | 2010-10-28 |
EP1606248B1 (en) | 2012-02-29 |
AU2004220360A1 (en) | 2004-09-23 |
CA2514988A1 (en) | 2004-09-23 |
ES2386811T3 (es) | 2012-08-31 |
RU2005131846A (ru) | 2006-03-27 |
EP1606248A2 (en) | 2005-12-21 |
ATE547397T1 (de) | 2012-03-15 |
NO20054672D0 (no) | 2005-10-11 |
CN100372831C (zh) | 2008-03-05 |
JP2006520367A (ja) | 2006-09-07 |
US20060258730A1 (en) | 2006-11-16 |
HK1089431A1 (en) | 2006-12-01 |
WO2004080951A2 (en) | 2004-09-23 |
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Legal Events
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CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: DOMPE FARMACEUTICI S.P.A., IT |
|
MM1K | Lapsed by not paying the annual fees |