NO310975B1 - Nye N-(arylsulfonyl)aminosyrederivater med bradykininreseptoraffinitet, fremgangsmate for fremstilling deravsamt farmasoytisk preparat - Google Patents
Nye N-(arylsulfonyl)aminosyrederivater med bradykininreseptoraffinitet, fremgangsmate for fremstilling deravsamt farmasoytisk preparat Download PDFInfo
- Publication number
- NO310975B1 NO310975B1 NO19983190A NO983190A NO310975B1 NO 310975 B1 NO310975 B1 NO 310975B1 NO 19983190 A NO19983190 A NO 19983190A NO 983190 A NO983190 A NO 983190A NO 310975 B1 NO310975 B1 NO 310975B1
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- Norway
- Prior art keywords
- compound
- formula
- hydrogen
- mixture
- unsubstituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 51
- 238000002360 preparation method Methods 0.000 title description 9
- 108050001736 Bradykinin receptor Proteins 0.000 title description 6
- 102000010183 Bradykinin receptor Human genes 0.000 title description 5
- 150000003862 amino acid derivatives Chemical class 0.000 title description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 306
- 239000000203 mixture Substances 0.000 claims description 200
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 77
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- -1 (C 1 -C 4 )alkyl R 10 Chemical compound 0.000 claims description 32
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000004985 diamines Chemical class 0.000 claims description 11
- 125000005493 quinolyl group Chemical group 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 235000005985 organic acids Nutrition 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 6
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 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 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 102220101549 rs199890548 Human genes 0.000 claims 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 200
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 117
- 239000000543 intermediate Substances 0.000 description 108
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 107
- 239000000243 solution Substances 0.000 description 96
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
- 238000003756 stirring Methods 0.000 description 82
- 239000000047 product Substances 0.000 description 76
- 235000019439 ethyl acetate Nutrition 0.000 description 70
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 53
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 53
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 43
- 239000011734 sodium Substances 0.000 description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
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- 239000002253 acid Substances 0.000 description 14
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 102400000967 Bradykinin Human genes 0.000 description 10
- 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 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 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 10
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- 238000004587 chromatography analysis Methods 0.000 description 8
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 8
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- RMBLTLXJGNILPG-UHFFFAOYSA-N 3-(4-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=C(C#N)C=C1 RMBLTLXJGNILPG-UHFFFAOYSA-N 0.000 description 6
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- BSALFGZSJNYKCB-UHFFFAOYSA-N tert-butyl n-[3-(4-cyanophenyl)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]carbamate Chemical compound C1CCCN1C(=O)C(NC(=O)OC(C)(C)C)CC1=CC=C(C#N)C=C1 BSALFGZSJNYKCB-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- BSHQPCLDMYSZII-UHFFFAOYSA-N pyrrolidine trihydrochloride Chemical compound Cl.Cl.Cl.N1CCCC1 BSHQPCLDMYSZII-UHFFFAOYSA-N 0.000 description 1
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- JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 1
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- IKFUOWLTOBNMNS-UHFFFAOYSA-M sodium;5,6,7,8-tetrahydronaphthalene-2-sulfonate Chemical compound [Na+].C1CCCC2=CC(S(=O)(=O)[O-])=CC=C21 IKFUOWLTOBNMNS-UHFFFAOYSA-M 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- BEJMQXQXIQDKCZ-UHFFFAOYSA-N tert-butyl n-(1-cyano-3-phenylpropan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(CC#N)CC1=CC=CC=C1 BEJMQXQXIQDKCZ-UHFFFAOYSA-N 0.000 description 1
- LDKDMDVMMCXTMO-UHFFFAOYSA-N tert-butyl n-(1-hydroxy-3-phenylpropan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(CO)CC1=CC=CC=C1 LDKDMDVMMCXTMO-UHFFFAOYSA-N 0.000 description 1
- PEZOYANXMXLSKX-UHFFFAOYSA-N tert-butyl n-[3-(4-cyanophenyl)-1-(2,5-dimethyl-2,5-dihydropyrrol-1-yl)-1-oxopropan-2-yl]carbamate Chemical compound CC1C=CC(C)N1C(=O)C(NC(=O)OC(C)(C)C)CC1=CC=C(C#N)C=C1 PEZOYANXMXLSKX-UHFFFAOYSA-N 0.000 description 1
- ODNQSNHNAHGZNQ-UHFFFAOYSA-N tert-butyl n-[3-[[3-(4-cyanophenyl)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]-3-oxo-1-(4-phenylphenyl)propyl]carbamate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(NC(=O)OC(C)(C)C)CC(=O)NC(C(=O)N1CCCC1)CC1=CC=C(C#N)C=C1 ODNQSNHNAHGZNQ-UHFFFAOYSA-N 0.000 description 1
- OZKDQCQPYTUZDW-UHFFFAOYSA-N tert-butyl n-[3-[[3-(4-cyanophenyl)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]-3-oxo-1-phenylpropyl]carbamate Chemical compound C=1C=CC=CC=1C(NC(=O)OC(C)(C)C)CC(=O)NC(C(=O)N1CCCC1)CC1=CC=C(C#N)C=C1 OZKDQCQPYTUZDW-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- 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
-
- 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
-
- 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/26—Radicals substituted by carbon atoms having three bonds to hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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)
- Chemical Kinetics & Catalysis (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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9600269A FR2743562B1 (fr) | 1996-01-11 | 1996-01-11 | Derives de n-(arylsulfonyl) aminoacides, leur preparation, les compositions pharmaceutiques en contenant |
| PCT/FR1997/000026 WO1997025315A1 (fr) | 1996-01-11 | 1997-01-07 | Nouveaux derives de n-(arylsulfonyl)aminoacides ayant une affinite pour les recepteurs de la bradykinine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO983190L NO983190L (no) | 1998-07-10 |
| NO310975B1 true NO310975B1 (no) | 2001-09-24 |
Family
ID=9488041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983190A NO310975B1 (no) | 1996-01-11 | 1998-07-10 | Nye N-(arylsulfonyl)aminosyrederivater med bradykininreseptoraffinitet, fremgangsmate for fremstilling deravsamt farmasoytisk preparat |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US6015812A (es) |
| EP (1) | EP0877737B1 (es) |
| JP (1) | JP4086316B2 (es) |
| AT (1) | ATE203745T1 (es) |
| AU (1) | AU1383297A (es) |
| BR (1) | BR9707120B1 (es) |
| DE (1) | DE69705930T2 (es) |
| ES (1) | ES2162231T3 (es) |
| FR (1) | FR2743562B1 (es) |
| MX (1) | MX9805289A (es) |
| NO (1) | NO310975B1 (es) |
| WO (1) | WO1997025315A1 (es) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5837815A (en) * | 1994-12-15 | 1998-11-17 | Sugen, Inc. | PYK2 related polypeptide products |
| BR9713465A (pt) | 1996-08-28 | 2000-03-28 | Procter & Gamble | Inibidores metalotprotease de amina cìclica sibstituìda |
| GB9621814D0 (en) * | 1996-10-19 | 1996-12-11 | British Biotech Pharm | Metalloproteinase inhibitors |
| FR2765222B1 (fr) * | 1997-06-27 | 1999-12-31 | Fournier Ind & Sante | Nouveaux composes de n-benzenesulfonyl-l-proline, procede de preparation et utilisation en therapeutique |
| WO1999006340A2 (en) | 1997-07-31 | 1999-02-11 | The Procter & Gamble Company | Sulfonylamino substituted hydroxamic acid derivatives as metalloprotease inhibitors |
| US6861442B1 (en) * | 1998-12-30 | 2005-03-01 | Sugen, Inc. | PYK2 and inflammation |
| HUP0202199A2 (en) | 1999-03-03 | 2002-10-28 | Procter & Gamble | Alkenyl- and alkynyl-containing metalloprotease inhibitors |
| PL350452A1 (en) | 1999-03-03 | 2002-12-16 | Procter & Gamble | Dihetero-substituted metalloprotease inhibitors |
| GB9913079D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| FR2819254B1 (fr) * | 2001-01-08 | 2003-04-18 | Fournier Lab Sa | Nouveaux composes de la n-(phenylsulfonyl) glycine, leur procede de preparation et leur utilisation pour obtenir des compostions pharmaceutiques |
| FR2822827B1 (fr) * | 2001-03-28 | 2003-05-16 | Sanofi Synthelabo | Nouveaux derives de n-(arylsulfonyl) beta-aminoacides comportant un groupe aminomethyle substitue, leur procede de preparation et les compositions pharmaceutiques en contenant |
| CN1268610C (zh) * | 2001-05-14 | 2006-08-09 | 诺瓦提斯公司 | 磺酰胺衍生物 |
| US6919343B2 (en) * | 2002-02-08 | 2005-07-19 | Merck & Co., Inc. | N-biphenyl(substituted methyl) aminocycloalkane-carboxamide derivatives |
| EP1476419B1 (en) * | 2002-02-08 | 2006-02-01 | Merck & Co., Inc. | N-biphenylmethyl aminocycloalkanecarboxamide derivatives |
| US7309721B2 (en) | 2002-03-01 | 2007-12-18 | Merck + Co., Inc. | Aminoalkylphosphonates and related compounds as Edg receptor agonists |
| FR2840897B1 (fr) * | 2002-06-14 | 2004-09-10 | Fournier Lab Sa | Nouveaux derives d'arylsulfonamides et leur utilisation en therapeutique |
| WO2004043940A1 (en) * | 2002-11-07 | 2004-05-27 | Merck & Co., Inc. | Phenylalanine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| FR2852958B1 (fr) * | 2003-03-25 | 2005-06-24 | Fournier Lab Sa | Nouveaux derives de benzenesulfonamides et leur utilisation en therapeutique |
| AU2004226197B2 (en) * | 2003-03-25 | 2009-12-03 | Laboratoires Fournier S.A. | Benzenesulphonamide derivatives, method for production and use thereof for treatment of pain |
| US7211566B2 (en) | 2003-04-01 | 2007-05-01 | Universite De Sherbrooke | Selective bradykinin (BK) B1 peptidic receptor antagonists and uses thereof |
| JP2006522835A (ja) * | 2003-04-10 | 2006-10-05 | アムジェン インコーポレイテッド | 環状アミン誘導体およびブラジキニンによって媒介される炎症関連障害の処置におけるそれらの使用 |
| EP1631542A1 (en) | 2003-04-10 | 2006-03-08 | Amgen, Inc. | Bicyclic compounds having bradykinin receptors affinity and pharmaceutical compositions thereof |
| CA2583267A1 (en) * | 2004-10-12 | 2006-04-27 | Amgen Inc. | Novel b1 bradykinin receptor antagonists |
| WO2006044355A1 (en) | 2004-10-13 | 2006-04-27 | Amgen Inc. | Triazoles and their use as bradykinin b1 receptor antagonists |
| JP2011512329A (ja) * | 2008-02-06 | 2011-04-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有効な鎮痛剤としてのアリールスルホンアミド |
| PE20091782A1 (es) * | 2008-04-08 | 2009-11-15 | Gruenenthal Chemie | Derivados de sulfonamida sustituida |
| EP2396301A2 (en) | 2009-02-13 | 2011-12-21 | Jerini AG | Small molecule bradykinin b1 receptor antagonists |
| WO2011000863A1 (en) * | 2009-07-01 | 2011-01-06 | Dsm Ip Assets B.V. | Sulfonamide derivatives for use in the treatment of skin conditions |
| 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 |
| PT2813502T (pt) * | 2013-06-14 | 2017-04-06 | Dompé Farm S P A | Antagonistas do recetor da bradicinina e composições farmacêuticas que os contêm |
| EP3740466B1 (en) | 2018-01-17 | 2024-03-06 | Migal Galilee Research Institute Ltd. | New methionine metabolic pathway inhibitors |
| WO2019142192A1 (en) | 2018-01-17 | 2019-07-25 | Gavish-Galilee Bio Applications Ltd. | New methionine metabolic pathway inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2701480B1 (fr) * | 1993-02-15 | 1995-05-24 | Sanofi Elf | Composés à groupe sulfamoyle et amidino, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
-
1996
- 1996-01-11 FR FR9600269A patent/FR2743562B1/fr not_active Expired - Fee Related
-
1997
- 1997-01-07 JP JP52491697A patent/JP4086316B2/ja not_active Expired - Fee Related
- 1997-01-07 BR BRPI9707120-0A patent/BR9707120B1/pt not_active IP Right Cessation
- 1997-01-07 AU AU13832/97A patent/AU1383297A/en not_active Abandoned
- 1997-01-07 WO PCT/FR1997/000026 patent/WO1997025315A1/fr active IP Right Grant
- 1997-01-07 US US09/101,214 patent/US6015812A/en not_active Expired - Lifetime
- 1997-01-07 DE DE69705930T patent/DE69705930T2/de not_active Expired - Lifetime
- 1997-01-07 AT AT97900243T patent/ATE203745T1/de not_active IP Right Cessation
- 1997-01-07 EP EP97900243A patent/EP0877737B1/fr not_active Expired - Lifetime
- 1997-01-07 ES ES97900243T patent/ES2162231T3/es not_active Expired - Lifetime
-
1998
- 1998-06-29 MX MX9805289A patent/MX9805289A/es not_active IP Right Cessation
- 1998-07-10 NO NO19983190A patent/NO310975B1/no not_active IP Right Cessation
-
1999
- 1999-11-04 US US09/434,333 patent/US6100278A/en not_active Expired - Lifetime
-
2000
- 2000-06-13 US US09/593,067 patent/US6313120B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69705930D1 (de) | 2001-09-06 |
| DE69705930T2 (de) | 2002-04-11 |
| FR2743562A1 (fr) | 1997-07-18 |
| NO983190L (no) | 1998-07-10 |
| BR9707120A (pt) | 1999-07-20 |
| ATE203745T1 (de) | 2001-08-15 |
| EP0877737B1 (fr) | 2001-08-01 |
| US6100278A (en) | 2000-08-08 |
| US6015812A (en) | 2000-01-18 |
| BR9707120B1 (pt) | 2010-10-05 |
| MX9805289A (es) | 1998-10-31 |
| US6313120B1 (en) | 2001-11-06 |
| FR2743562B1 (fr) | 1998-04-03 |
| AU1383297A (en) | 1997-08-01 |
| EP0877737A1 (fr) | 1998-11-18 |
| JP2000504315A (ja) | 2000-04-11 |
| WO1997025315A1 (fr) | 1997-07-17 |
| ES2162231T3 (es) | 2001-12-16 |
| JP4086316B2 (ja) | 2008-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |