DE10360745A1 - Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel - Google Patents
Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel Download PDFInfo
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- DE10360745A1 DE10360745A1 DE10360745A DE10360745A DE10360745A1 DE 10360745 A1 DE10360745 A1 DE 10360745A1 DE 10360745 A DE10360745 A DE 10360745A DE 10360745 A DE10360745 A DE 10360745A DE 10360745 A1 DE10360745 A1 DE 10360745A1
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- Prior art keywords
- alkyl
- phenyl
- group
- amino
- chloro
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- -1 amide compounds Chemical class 0.000 title claims abstract description 330
- 239000003814 drug Substances 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 title claims description 139
- 239000005557 antagonist Substances 0.000 title claims description 23
- 230000000694 effects Effects 0.000 title claims description 9
- 238000011282 treatment Methods 0.000 claims abstract description 57
- 208000008589 Obesity Diseases 0.000 claims abstract description 42
- 235000020824 obesity Nutrition 0.000 claims abstract description 38
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims abstract description 12
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 8
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 6
- 208000032841 Bulimia Diseases 0.000 claims abstract description 5
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 5
- 208000030814 Eating disease Diseases 0.000 claims abstract description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 4
- 206010020710 Hyperphagia Diseases 0.000 claims abstract description 4
- 208000022531 anorexia Diseases 0.000 claims abstract description 4
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 4
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 4
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 172
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 61
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 52
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 51
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 125000004122 cyclic group Chemical group 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- 229910052794 bromium Inorganic materials 0.000 claims description 36
- 239000013543 active substance Substances 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 150000003254 radicals Chemical group 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 22
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims description 22
- 229940079593 drug Drugs 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
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- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 238000011321 prophylaxis Methods 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 206010003246 arthritis Diseases 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
- 208000002249 Diabetes Complications Diseases 0.000 claims description 8
- 206010012655 Diabetic complications Diseases 0.000 claims description 8
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 230000001364 causal effect Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 229940044551 receptor antagonist Drugs 0.000 claims description 7
- 239000002464 receptor antagonist Substances 0.000 claims description 7
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 5
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 5
- OCELZDDEJJBFSU-UHFFFAOYSA-N 2-chloro-5-[3-[4-(5-phenylpentylamino)phenyl]propanoylamino]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(NC(=O)CCC=2C=CC(NCCCCCC=3C=CC=CC=3)=CC=2)=C1 OCELZDDEJJBFSU-UHFFFAOYSA-N 0.000 claims description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- 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 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- NPVONNZNIBNQBN-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(4-hydroxy-3,5-dimethylphenyl)propanamide Chemical compound CC1=C(O)C(C)=CC(NC(=O)CCC=2C=CC(N)=CC=2)=C1 NPVONNZNIBNQBN-UHFFFAOYSA-N 0.000 claims description 4
- LSFSTMXFFDNMJQ-UHFFFAOYSA-N 4-[3-[3-(2-anilino-1,3-benzoxazol-6-yl)propanoylamino]phenoxy]butanoic acid Chemical compound OC(=O)CCCOC1=CC=CC(NC(=O)CCC=2C=C3OC(NC=4C=CC=CC=4)=NC3=CC=2)=C1 LSFSTMXFFDNMJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 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 4
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
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- 206010027566 Micturition urgency Diseases 0.000 claims description 4
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- CYNDKGIQZOATHH-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propylsulfanyl]phenyl]-3-phenylprop-2-ynamide Chemical compound CN(C)CCCSC1=CC=CC=C1NC(=O)C#CC1=CC=CC=C1 CYNDKGIQZOATHH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 208000020629 overactive bladder Diseases 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- RQCSDMPDPILTRX-UHFFFAOYSA-N 2-methylsulfanyl-5-[3-[4-(octadecylamino)phenyl]propanoylamino]benzoic acid Chemical compound C1=CC(NCCCCCCCCCCCCCCCCCC)=CC=C1CCC(=O)NC1=CC=C(SC)C(C(O)=O)=C1 RQCSDMPDPILTRX-UHFFFAOYSA-N 0.000 claims description 3
- OOOPKDWRISJSLD-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-n-(4-hydroxy-3,5-dimethylphenyl)propanamide Chemical compound C1=CC(N(C)C)=CC=C1CCC(=O)NC1=CC(C)=C(O)C(C)=C1 OOOPKDWRISJSLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
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- 201000008736 Systemic mastocytosis Diseases 0.000 claims description 3
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- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 3
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- 125000002541 furyl group Chemical group 0.000 claims description 3
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
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- YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 claims description 2
- SMOHMDMTVAYPAI-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1h-azepine Chemical compound C1CC=CCCN1 SMOHMDMTVAYPAI-UHFFFAOYSA-N 0.000 claims description 2
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 2
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- ZWECFULPLKCFLY-UHFFFAOYSA-N N-[4-(1-imidazol-1-yl-2-methylpropyl)phenyl]-3-phenylprop-2-ynamide Chemical compound C1=CN=CN1C(C(C)C)C(C=C1)=CC=C1NC(=O)C#CC1=CC=CC=C1 ZWECFULPLKCFLY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
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- 125000004429 atom Chemical group 0.000 claims description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 2
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- VJNSFUXBIQJGSE-UHFFFAOYSA-N methyl 2-chloro-5-[3-[4-(5-phenylpentylamino)phenyl]propanoylamino]benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC(NC(=O)CCC=2C=CC(NCCCCCC=3C=CC=CC=3)=CC=2)=C1 VJNSFUXBIQJGSE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical compound ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
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- GNWONDUZVUZUOQ-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(4-naphthalen-2-yl-3,6-dihydro-2h-pyridin-1-yl)propoxy]phenyl]-n-methyl-n-phenylprop-2-enamide Chemical compound C=1C=CC=C(OCC(O)CN2CC=C(CC2)C=2C=C3C=CC=CC3=CC=2)C=1C=CC(=O)N(C)C1=CC=CC=C1 GNWONDUZVUZUOQ-UHFFFAOYSA-N 0.000 claims 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
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- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- Chemical & Material Sciences (AREA)
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Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10360745A DE10360745A1 (de) | 2003-12-23 | 2003-12-23 | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| EP04803987A EP1708698A1 (de) | 2003-12-23 | 2004-12-17 | 3-(4-piperidin-1ylmethyl-phenyl)-propionsäure-phenylamid-derivate und verwandte verbindungen als mch (melanine concentrating hormone) antagonsiten zur behandlung von essstörungen |
| JP2006546009A JP2007520466A (ja) | 2003-12-23 | 2004-12-17 | 摂食障害を治療するためのmchアンタゴニスト(メラニン含有ホルモン)の形態で使用される3−(4−ピペリジン−1−イルメチル−フェニル)−プロピオン酸−フェニルアミド誘導体及び関連化合物 |
| PCT/EP2004/014378 WO2005063239A1 (de) | 2003-12-23 | 2004-12-17 | 3-(4-piperidin-1ylmethyl-phenyl) -propionsäure-phrnylamid-derivate und verwandte verbindungen als mch (melanine concentrating hormone) antagonisten zur behandlung von essstörungen |
| CA002550649A CA2550649A1 (en) | 2003-12-23 | 2004-12-17 | 3-(4-piperidine-1ylmethyl-phenyl)-propion acid-phenylamide-derivatives and related compounds used in the form of mch antagonists (melanine concentrating hormone) for treating eating disorders |
| UY28689A UY28689A1 (es) | 2003-12-23 | 2004-12-20 | Nuevos compuestos amida con actividad antagonista de mch y medicamentos que contienen estos compuestos. |
| ARP040104840A AR048019A1 (es) | 2003-12-23 | 2004-12-22 | Derivados de amida con actividad antagonista de mch y composiciones farmaceuticas que los contienen |
| TW093140144A TW200530180A (en) | 2003-12-23 | 2004-12-22 | New amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| US11/021,897 US7592373B2 (en) | 2003-12-23 | 2004-12-23 | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| PE2005000007A PE20050678A1 (es) | 2003-12-23 | 2005-01-03 | Nuevos compuestos amida con actividad antagonista de mch y medicamentos que contiene estos compuestos |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10360745A DE10360745A1 (de) | 2003-12-23 | 2003-12-23 | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10360745A1 true DE10360745A1 (de) | 2005-07-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10360745A Withdrawn DE10360745A1 (de) | 2003-12-23 | 2003-12-23 | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1708698A1 (enExample) |
| JP (1) | JP2007520466A (enExample) |
| AR (1) | AR048019A1 (enExample) |
| CA (1) | CA2550649A1 (enExample) |
| DE (1) | DE10360745A1 (enExample) |
| PE (1) | PE20050678A1 (enExample) |
| TW (1) | TW200530180A (enExample) |
| UY (1) | UY28689A1 (enExample) |
| WO (1) | WO2005063239A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| EP1863756A1 (en) * | 2005-03-24 | 2007-12-12 | Janssen Pharmaceutica N.V. | Biaryl derived amide modulators of vanilloid vr1 receptor |
| CN101296906A (zh) * | 2005-10-26 | 2008-10-29 | 贝林格尔·英格海姆国际有限公司 | 具有mch拮抗活性的(杂)芳基化合物及包含这些化合物的药物 |
| US7977346B2 (en) * | 2006-01-17 | 2011-07-12 | Guoqing Paul Chen | Spiro compounds and methods of use |
| NZ575520A (en) | 2006-08-25 | 2012-03-30 | Boehringer Ingelheim Int | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
| TW200831485A (en) | 2006-12-11 | 2008-08-01 | Boehringer Ingelheim Int | New pyridazine derivatives with MCH antagonistic activity and medicaments comprising these compounds |
| JP5722892B2 (ja) | 2010-07-15 | 2015-05-27 | 武田薬品工業株式会社 | 複素環化合物 |
| EP4284365A4 (en) | 2021-01-29 | 2024-12-18 | Cedilla Therapeutics, Inc. | CDK2 INHIBITORS AND METHODS OF USE THEREOF |
| EP4358954A4 (en) | 2021-06-26 | 2025-09-03 | Cedilla Therapeutics Inc | CDK2 INHIBITORS AND METHODS OF USE THEREOF |
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| GB8530507D0 (en) * | 1985-12-11 | 1986-01-22 | Glaxo Group Plc | Chemical compounds |
| JPH0454118A (ja) * | 1990-06-20 | 1992-02-21 | Tanabe Seiyaku Co Ltd | 5―リポキシゲナーゼ阻害剤 |
| PT810220E (pt) * | 1996-05-28 | 2002-04-29 | Pfizer | Derivados de arilacrilamida como agonistas ou antigonistas de 5ht1 |
| DE69824885T2 (de) * | 1997-12-11 | 2005-07-21 | Janssen Pharmaceutica N.V. | Anilide als vitamin-a-säure-mimetika |
| JP2000143635A (ja) * | 1998-06-10 | 2000-05-26 | Takeda Chem Ind Ltd | 血管新生阻害剤 |
| JP2000086603A (ja) * | 1998-07-15 | 2000-03-28 | Yoshitomi Pharmaceut Ind Ltd | 桂皮酸アミド誘導体および3―フェニルプロピオン酸アミド誘導体 |
| WO2000005223A2 (en) * | 1998-07-23 | 2000-02-03 | Astrazeneca Ab | Heterocyclic derivatives and their use as integrin inhibitors |
| EP1153017B1 (en) * | 1999-02-16 | 2006-05-03 | Aventis Pharma Limited | Bicyclic compounds and their use as integrin receptor ligands |
| CN1371357A (zh) * | 1999-07-01 | 2002-09-25 | 大正制药株式会社 | 氨基苯甲酸衍生物 |
| JP2002003370A (ja) * | 1999-09-20 | 2002-01-09 | Takeda Chem Ind Ltd | メラニン凝集ホルモン拮抗剤 |
| DE10115994A1 (de) * | 2001-03-30 | 2002-10-10 | Wella Ag | (p-Amino-hydroxyphenyl)acrylamid-Derivate und diese Verbindungen enthaltende Färbemittel |
| CA2446593A1 (en) * | 2001-05-10 | 2002-11-21 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and pharmaceutical compositions comprising the same as an active ingredient |
| US6897220B2 (en) * | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US20050009815A1 (en) * | 2001-11-27 | 2005-01-13 | Devita Robert J. | 4-Aminoquinoline compounds |
| AU2002352878B2 (en) * | 2001-11-27 | 2007-11-22 | Merck Sharp & Dohme Corp. | 2-Aminoquinoline compounds |
| MXPA04005427A (es) * | 2001-12-10 | 2005-04-19 | Amgen Inc | Ligandos de receptor vainilloide y su uso en tratamientos. |
| JP2006512306A (ja) * | 2002-08-29 | 2006-04-13 | テンプル・ユニバーシティ−オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | アリール及びヘテロアリールプロペンアミド、それらの誘導体並びにそれらの治療用途 |
| WO2004069792A2 (en) * | 2003-02-03 | 2004-08-19 | Janssen Pharmaceutica N.V. | Quinoline-derived amide modulators of vanilloid vr1 receptor |
| WO2004072018A1 (ja) * | 2003-02-12 | 2004-08-26 | Takeda Pharmaceutical Company Limited | アミン誘導体 |
| JP4630555B2 (ja) * | 2003-02-12 | 2011-02-09 | 武田薬品工業株式会社 | アミン誘導体 |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
-
2003
- 2003-12-23 DE DE10360745A patent/DE10360745A1/de not_active Withdrawn
-
2004
- 2004-12-17 JP JP2006546009A patent/JP2007520466A/ja active Pending
- 2004-12-17 EP EP04803987A patent/EP1708698A1/de not_active Withdrawn
- 2004-12-17 CA CA002550649A patent/CA2550649A1/en not_active Abandoned
- 2004-12-17 WO PCT/EP2004/014378 patent/WO2005063239A1/de not_active Ceased
- 2004-12-20 UY UY28689A patent/UY28689A1/es not_active Application Discontinuation
- 2004-12-22 TW TW093140144A patent/TW200530180A/zh unknown
- 2004-12-22 AR ARP040104840A patent/AR048019A1/es unknown
-
2005
- 2005-01-03 PE PE2005000007A patent/PE20050678A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007520466A (ja) | 2007-07-26 |
| UY28689A1 (es) | 2005-08-31 |
| EP1708698A1 (de) | 2006-10-11 |
| CA2550649A1 (en) | 2005-07-14 |
| AR048019A1 (es) | 2006-03-22 |
| WO2005063239A1 (de) | 2005-07-14 |
| PE20050678A1 (es) | 2005-10-27 |
| TW200530180A (en) | 2005-09-16 |
| WO2005063239A9 (de) | 2006-03-09 |
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