DE19837627A1 - Neue Aminosäureester von Arylsulfonamiden und Analoga - Google Patents
Neue Aminosäureester von Arylsulfonamiden und AnalogaInfo
- Publication number
- DE19837627A1 DE19837627A1 DE19837627A DE19837627A DE19837627A1 DE 19837627 A1 DE19837627 A1 DE 19837627A1 DE 19837627 A DE19837627 A DE 19837627A DE 19837627 A DE19837627 A DE 19837627A DE 19837627 A1 DE19837627 A1 DE 19837627A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- phenyl
- hydrogen
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 aminoacid esters Chemical class 0.000 title claims abstract description 117
- 208000002193 Pain Diseases 0.000 title claims description 6
- 230000036407 pain Effects 0.000 title claims description 6
- 208000035143 Bacterial infection Diseases 0.000 title claims description 4
- 208000036142 Viral infection Diseases 0.000 title claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 title claims description 4
- 230000004770 neurodegeneration Effects 0.000 title claims description 4
- 206010010904 Convulsion Diseases 0.000 title claims description 3
- 230000001580 bacterial effect Effects 0.000 title claims description 3
- 230000036461 convulsion Effects 0.000 title claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 title claims description 3
- 230000009385 viral infection Effects 0.000 title claims description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 title abstract description 4
- 235000001014 amino acid Nutrition 0.000 title abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 125000006239 protecting group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 19
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 125000000539 amino acid group Chemical group 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 238000007796 conventional method Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 210000003625 skull Anatomy 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 229920001774 Perfluoroether Polymers 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 4
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 208000018198 spasticity Diseases 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 208000016285 Movement disease Diseases 0.000 claims description 3
- 206010047700 Vomiting Diseases 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 206010061428 decreased appetite Diseases 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010028813 Nausea Diseases 0.000 claims description 2
- 206010039897 Sedation Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000001212 derivatisation Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 210000000777 hematopoietic system Anatomy 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 230000008693 nausea Effects 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 230000036280 sedation Effects 0.000 claims description 2
- 210000000697 sensory organ Anatomy 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 229940121376 cannabinoid receptor agonist Drugs 0.000 abstract description 2
- 239000003537 cannabinoid receptor agonist Substances 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000005549 heteroarylene group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000012360 testing method Methods 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000126 substance Substances 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
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- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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- GBCOTHPVQOTZKQ-UHFFFAOYSA-N pent-1-yn-3-one Chemical compound CCC(=O)C#C GBCOTHPVQOTZKQ-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Otolaryngology (AREA)
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Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19837627A DE19837627A1 (de) | 1998-08-19 | 1998-08-19 | Neue Aminosäureester von Arylsulfonamiden und Analoga |
| AU54204/99A AU5420499A (en) | 1998-08-19 | 1999-08-06 | Novel aryl sulphonamide amino acid esters and analogues |
| ES99940158T ES2233064T3 (es) | 1998-08-19 | 1999-08-06 | Esteres de aminoacido de arilsulfonamidas y analogos. |
| US09/763,196 US6545050B1 (en) | 1998-08-19 | 1999-08-06 | Aryl sulphonamide amino acid esters and analogues |
| JP2000566242A JP2002523396A (ja) | 1998-08-19 | 1999-08-06 | 新規なアリールスルホンアミドアミノ酸エステル類および同族体 |
| PCT/EP1999/005683 WO2000010968A2 (de) | 1998-08-19 | 1999-08-06 | Neue aminosäureester von arylsulfonamiden und analoga |
| DE59911005T DE59911005D1 (de) | 1998-08-19 | 1999-08-06 | Aminosäureester von arylsulfonamiden und analoga |
| EP99940158A EP1105371B1 (de) | 1998-08-19 | 1999-08-06 | Aminosäureester von arylsulfonamiden und analoga |
| CA002341028A CA2341028A1 (en) | 1998-08-19 | 1999-08-06 | Novel aryl sulphonamide amino acid esters and analogues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19837627A DE19837627A1 (de) | 1998-08-19 | 1998-08-19 | Neue Aminosäureester von Arylsulfonamiden und Analoga |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19837627A1 true DE19837627A1 (de) | 2000-02-24 |
Family
ID=7878029
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19837627A Withdrawn DE19837627A1 (de) | 1998-08-19 | 1998-08-19 | Neue Aminosäureester von Arylsulfonamiden und Analoga |
| DE59911005T Expired - Fee Related DE59911005D1 (de) | 1998-08-19 | 1999-08-06 | Aminosäureester von arylsulfonamiden und analoga |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59911005T Expired - Fee Related DE59911005D1 (de) | 1998-08-19 | 1999-08-06 | Aminosäureester von arylsulfonamiden und analoga |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6545050B1 (https=) |
| EP (1) | EP1105371B1 (https=) |
| JP (1) | JP2002523396A (https=) |
| AU (1) | AU5420499A (https=) |
| CA (1) | CA2341028A1 (https=) |
| DE (2) | DE19837627A1 (https=) |
| ES (1) | ES2233064T3 (https=) |
| WO (1) | WO2000010968A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7351729B2 (en) | 2002-03-08 | 2008-04-01 | Signal Pharmaceuticals, Llc | JNK inhibitors for use in combination therapy for treating or managing proliferative disorders and cancers |
| EP2130820A1 (en) | 2002-02-19 | 2009-12-09 | Shionogi & Co., Ltd. | Antipruritics |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2318731C (en) * | 1998-01-29 | 2012-05-29 | Tularik Inc. | Ppar-gamma modulators |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| DE10015866A1 (de) * | 2000-03-30 | 2001-10-11 | Bayer Ag | Aryl- und Heteroarylsulfonate |
| WO2001082916A2 (en) * | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| DE10047486A1 (de) * | 2000-09-26 | 2002-04-11 | Bayer Ag | Phenoxyphenyl Alkansulfonate |
| KR100642570B1 (ko) * | 2001-03-08 | 2006-11-10 | 시오노기세이야쿠가부시키가이샤 | 1,3-티아진 유도체를 함유하는 의약 조성물 |
| WO2003007887A2 (en) | 2001-07-20 | 2003-01-30 | Merck & Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| WO2003061699A1 (en) * | 2001-12-27 | 2003-07-31 | Japan Tobacco, Inc. | Remedies for allergic diseases |
| NZ534757A (en) | 2002-03-12 | 2006-07-28 | Merck & Co Inc | Substituted amides |
| EP1490043A4 (en) | 2002-03-26 | 2007-05-30 | Merck & Co Inc | SPIROCYCLIC AMIDS AS CANNABINOID RECEPTOR MODULATORS |
| WO2003082191A2 (en) | 2002-03-28 | 2003-10-09 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| EP1499306A4 (en) | 2002-04-12 | 2007-03-28 | Merck & Co Inc | BICYCLIC AMIDE |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| CA2538291A1 (en) * | 2003-09-18 | 2005-03-31 | Merck & Co., Inc. | Substituted sulfonamides |
| AU2004274309B2 (en) | 2003-09-22 | 2010-04-08 | Msd K.K. | Novel piperidine derivative |
| US7223761B2 (en) * | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| TW200522944A (en) | 2003-12-23 | 2005-07-16 | Lilly Co Eli | CB1 modulator compounds |
| US20050250820A1 (en) * | 2004-03-08 | 2005-11-10 | Amgen Inc. | Therapeutic modulation of PPARgamma activity |
| AU2005230864A1 (en) | 2004-03-29 | 2005-10-20 | Merck Sharp & Dohme Corp. | Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
| CN1993320A (zh) | 2004-08-06 | 2007-07-04 | 默克公司 | 作为11－β－羟基类固醇脱氢酶－1的抑制剂的磺酰化合物 |
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| FR1600425A (https=) | 1968-08-21 | 1970-07-27 | ||
| US4243819A (en) * | 1978-02-16 | 1981-01-06 | Zoecon Corporation | Substituted amino acids |
| CA2078126A1 (en) * | 1990-03-27 | 1991-09-28 | Jerry Leroy Adams | 5-lipoxygenase inhibitors |
| US5149357A (en) | 1990-06-19 | 1992-09-22 | Fmc Corporation | Herbicidal substituted benzoylsulfonamides |
| FR2735774B1 (fr) * | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| TR199902012T2 (xx) | 1997-02-21 | 2000-01-21 | Bayer Aktiengesellschaft | Arils�lfonamidler ve analoglar� |
-
1998
- 1998-08-19 DE DE19837627A patent/DE19837627A1/de not_active Withdrawn
-
1999
- 1999-08-06 US US09/763,196 patent/US6545050B1/en not_active Expired - Fee Related
- 1999-08-06 CA CA002341028A patent/CA2341028A1/en not_active Abandoned
- 1999-08-06 AU AU54204/99A patent/AU5420499A/en not_active Abandoned
- 1999-08-06 ES ES99940158T patent/ES2233064T3/es not_active Expired - Lifetime
- 1999-08-06 DE DE59911005T patent/DE59911005D1/de not_active Expired - Fee Related
- 1999-08-06 EP EP99940158A patent/EP1105371B1/de not_active Expired - Lifetime
- 1999-08-06 WO PCT/EP1999/005683 patent/WO2000010968A2/de not_active Ceased
- 1999-08-06 JP JP2000566242A patent/JP2002523396A/ja not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2130820A1 (en) | 2002-02-19 | 2009-12-09 | Shionogi & Co., Ltd. | Antipruritics |
| US7351729B2 (en) | 2002-03-08 | 2008-04-01 | Signal Pharmaceuticals, Llc | JNK inhibitors for use in combination therapy for treating or managing proliferative disorders and cancers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59911005D1 (de) | 2004-12-09 |
| WO2000010968A2 (de) | 2000-03-02 |
| CA2341028A1 (en) | 2000-03-02 |
| EP1105371B1 (de) | 2004-11-03 |
| AU5420499A (en) | 2000-03-14 |
| EP1105371A2 (de) | 2001-06-13 |
| WO2000010968A3 (de) | 2000-11-09 |
| US6545050B1 (en) | 2003-04-08 |
| JP2002523396A (ja) | 2002-07-30 |
| ES2233064T3 (es) | 2005-06-01 |
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