UA79323C2 - Selected cgrp antagonists, method for production and use thereof as medicament - Google Patents
Selected cgrp antagonists, method for production and use thereof as medicament Download PDFInfo
- Publication number
- UA79323C2 UA79323C2 UAA200504872A UA2005004872A UA79323C2 UA 79323 C2 UA79323 C2 UA 79323C2 UA A200504872 A UAA200504872 A UA A200504872A UA 2005004872 A UA2005004872 A UA 2005004872A UA 79323 C2 UA79323 C2 UA 79323C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- oxo
- piperidin
- amino
- chloro
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 229940127597 CGRP antagonist Drugs 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 239000000203 mixture Substances 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 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 abstract description 16
- 150000004677 hydrates Chemical class 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- -1 phenylsulfonylimino group Chemical group 0.000 claims description 412
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 256
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 208
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 163
- NOSOEJSZWOKISI-UHFFFAOYSA-N butane-1,4-dione Chemical compound O=[C]CC[C]=O NOSOEJSZWOKISI-UHFFFAOYSA-N 0.000 claims description 151
- 238000006243 chemical reaction Methods 0.000 claims description 113
- 229910052757 nitrogen Inorganic materials 0.000 claims description 94
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 74
- 239000000460 chlorine Substances 0.000 claims description 62
- 125000003277 amino group Chemical group 0.000 claims description 60
- 229910052801 chlorine Inorganic materials 0.000 claims description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 54
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 53
- 150000001408 amides Chemical class 0.000 claims description 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 125000001153 fluoro group Chemical group F* 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 239000011737 fluorine Substances 0.000 claims description 45
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 44
- 150000001721 carbon Chemical group 0.000 claims description 41
- 125000004076 pyridyl group Chemical group 0.000 claims description 40
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000003282 alkyl amino group Chemical group 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 31
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 31
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 30
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 25
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 229910052740 iodine Inorganic materials 0.000 claims description 25
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 25
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001246 bromo group Chemical group Br* 0.000 claims description 16
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- 230000003993 interaction Effects 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 11
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 10
- 239000005557 antagonist Substances 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000012634 fragment Substances 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 229940126601 medicinal product Drugs 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 7
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 7
- ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 claims description 6
- 206010019233 Headaches Diseases 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 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 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 5
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
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- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
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- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
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- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 4
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
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- 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
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 4
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- WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10250080A DE10250080A1 (de) | 2002-10-25 | 2002-10-25 | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
PCT/EP2003/011762 WO2004037810A1 (de) | 2002-10-25 | 2003-10-23 | Ausgewählte cgrp-antagonisten, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
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UA79323C2 true UA79323C2 (en) | 2007-06-11 |
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UAA200504872A UA79323C2 (en) | 2002-10-25 | 2003-10-23 | Selected cgrp antagonists, method for production and use thereof as medicament |
Country Status (27)
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---|---|
EP (1) | EP1558600B1 (ko) |
JP (1) | JP4401296B2 (ko) |
KR (1) | KR20050074970A (ko) |
CN (1) | CN1708493A (ko) |
AR (1) | AR041718A1 (ko) |
AT (1) | ATE394392T1 (ko) |
AU (1) | AU2003276156A1 (ko) |
BR (1) | BR0315665A (ko) |
CA (1) | CA2503455A1 (ko) |
CO (1) | CO5570704A2 (ko) |
DE (2) | DE10250080A1 (ko) |
DK (1) | DK1558600T3 (ko) |
EA (1) | EA009219B1 (ko) |
EC (1) | ECSP055747A (ko) |
ES (1) | ES2306918T3 (ko) |
HR (1) | HRP20050364A2 (ko) |
IL (1) | IL168056A0 (ko) |
MX (1) | MXPA05004375A (ko) |
NO (1) | NO20052496L (ko) |
PE (1) | PE20040592A1 (ko) |
PL (1) | PL376450A1 (ko) |
RS (1) | RS20050311A (ko) |
TW (1) | TW200413317A (ko) |
UA (1) | UA79323C2 (ko) |
UY (1) | UY28034A1 (ko) |
WO (1) | WO2004037810A1 (ko) |
ZA (1) | ZA200502248B (ko) |
Families Citing this family (41)
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DE19963868A1 (de) * | 1999-12-30 | 2001-07-12 | Boehringer Ingelheim Pharma | Neue substituierte Piperidine, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
US7345068B2 (en) | 2002-02-07 | 2008-03-18 | Hitoshi Endou | Aromatic amino acid derivatives and medicinal compositions |
US7220862B2 (en) | 2002-06-05 | 2007-05-22 | Bristol-Myers Squibb Company | Calcitonin gene related peptide receptor antagonists |
US7842808B2 (en) | 2002-06-05 | 2010-11-30 | Bristol-Myers Squibb Company | Anti-migraine spirocycles |
US7595312B2 (en) | 2002-10-25 | 2009-09-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Selected CGRP antagonists, processes for preparing them and their use as pharmaceutical compositions |
CA2531407A1 (en) * | 2003-07-07 | 2005-01-20 | Boehringer Ingelheim International Gmbh | Use of cgrp antagonists in treatment and prevention of hot flushes in prostate cancer patients |
US7569578B2 (en) | 2003-12-05 | 2009-08-04 | Bristol-Meyers Squibb Company | Heterocyclic anti-migraine agents |
TW200533398A (en) * | 2004-03-29 | 2005-10-16 | Bristol Myers Squibb Co | Novel therapeutic agents for the treatment of migraine |
DE102004015723A1 (de) * | 2004-03-29 | 2005-10-20 | Boehringer Ingelheim Pharma | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
DE102004018796A1 (de) * | 2004-04-15 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
DE102004018795A1 (de) | 2004-04-15 | 2005-10-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
US7696195B2 (en) | 2004-04-22 | 2010-04-13 | Boehringer Ingelheim International Gmbh | Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions |
ATE537153T1 (de) * | 2004-09-09 | 2011-12-15 | Merck Sharp & Dohme | Arylspirolactamverbindungen als antagonisten des cgrp-rezeptors |
US7384930B2 (en) | 2004-11-03 | 2008-06-10 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
US7384931B2 (en) | 2004-11-03 | 2008-06-10 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
US7449586B2 (en) | 2004-12-03 | 2008-11-11 | Bristol-Myers Squibb Company | Processes for the preparation of CGRP-receptor antagonists and intermediates thereof |
DE102004063755A1 (de) * | 2004-12-29 | 2006-07-20 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von CGRP-Antagonisten zur Behandlung und Vorbeugung von Hitzewallungen bei Patienten mit Prostatakrebs |
DE102004063752A1 (de) * | 2004-12-29 | 2006-07-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung ausgewählter CGRP-Antagonisten zur Bekämpfung menopausaler Hitzewallungen |
DE102004063753A1 (de) * | 2004-12-29 | 2006-07-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung ausgewählter CGRP-Antagonisten in Kombination mit anderen Arzneistoffen gegen Migräne für die Behandlung von Migräne |
US7491717B2 (en) | 2005-03-23 | 2009-02-17 | Boehringer Ingelheim International Gmbh | Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions |
CN101146799A (zh) * | 2005-03-23 | 2008-03-19 | 贝林格尔·英格海姆国际有限公司 | Cgrp拮抗剂、其制备方法以及其作为药物的用途 |
EP1770091A1 (de) | 2005-09-29 | 2007-04-04 | Boehringer Ingelheim Pharma GmbH & Co. KG | CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
US7439237B2 (en) | 2005-04-15 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions |
DE102005038831A1 (de) * | 2005-08-17 | 2007-02-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
US7834007B2 (en) | 2005-08-25 | 2010-11-16 | Bristol-Myers Squibb Company | CGRP antagonists |
EP1770087A1 (de) * | 2005-09-29 | 2007-04-04 | Boehringer Ingelheim Pharma GmbH & Co. KG | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
EP1770086A1 (de) * | 2005-09-29 | 2007-04-04 | Boehringer Ingelheim Pharma GmbH & Co. KG | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
DE102005050892A1 (de) | 2005-10-21 | 2007-04-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
DE102006017827A1 (de) * | 2006-04-13 | 2007-10-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue kristalline Verbindungen |
PE20080370A1 (es) * | 2006-06-08 | 2008-06-13 | Boehringer Ingelheim Int | Derivados de quinazolinona como antagonistas de cgrp |
DE102007038250A1 (de) * | 2007-08-13 | 2009-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Herstellverfahren |
WO2009050234A1 (de) | 2007-10-18 | 2009-04-23 | Boehringer Ingelheim International Gmbh | Cgrp-antagonisten |
EP2065381A1 (de) | 2007-10-18 | 2009-06-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | CGRP Antagonisten |
CA2705405A1 (en) | 2007-11-22 | 2009-05-28 | Boehringer Ingelheim International Gmbh | New compounds |
KR101409076B1 (ko) | 2008-08-01 | 2014-06-18 | 미쓰이가가쿠 아그로 가부시키가이샤 | 아미드 유도체, 그 아미드 유도체를 함유하는 유해 생물 방제제 및 유해 생물의 방제 방법 |
PT2396081T (pt) | 2009-02-16 | 2017-07-11 | Nogra Pharma Ltd | Compostos alquilamido e suas utilizações |
CA2864059C (en) | 2012-02-09 | 2020-04-28 | Nogra Pharma Limited | Methods of treating fibrosis |
WO2018021447A1 (ja) | 2016-07-28 | 2018-02-01 | 塩野義製薬株式会社 | ドーパミンd3受容体拮抗作用を有する含窒素縮環化合物 |
AU2018317805B2 (en) * | 2017-08-16 | 2021-04-15 | BioVersys AG | Novel compounds |
KR20200112910A (ko) | 2018-01-26 | 2020-10-05 | 시오노기 앤드 컴파니, 리미티드 | 도파민 d3 수용체 길항 작용을 갖는 축환 화합물 |
CA3128302A1 (en) | 2019-02-08 | 2020-08-13 | Nogra Pharma Limited | Process of making 3-(4'-aminophenyl)-2-methoxypropionic acid, and analogs and intermediates thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6552043B1 (en) * | 1998-09-30 | 2003-04-22 | Merck Sharpe & Dohme Ltd. | Benzimidazolinyl piperidines as CGRP ligands |
DE19937304C2 (de) * | 1999-08-10 | 2003-08-21 | Boehringer Ingelheim Pharma | Verwendung von CGRP-Antagonisten zur Bekämpfung menopausaler Hitzewallungen |
-
2002
- 2002-10-25 DE DE10250080A patent/DE10250080A1/de not_active Withdrawn
-
2003
- 2003-10-22 UY UY28034A patent/UY28034A1/es not_active Application Discontinuation
- 2003-10-23 AT AT03809317T patent/ATE394392T1/de active
- 2003-10-23 KR KR1020057007144A patent/KR20050074970A/ko not_active Application Discontinuation
- 2003-10-23 UA UAA200504872A patent/UA79323C2/uk unknown
- 2003-10-23 EP EP03809317A patent/EP1558600B1/de not_active Expired - Lifetime
- 2003-10-23 RS YUP-2005/0311A patent/RS20050311A/sr unknown
- 2003-10-23 BR BR0315665-6A patent/BR0315665A/pt not_active Expired - Fee Related
- 2003-10-23 CN CNA2003801020040A patent/CN1708493A/zh active Pending
- 2003-10-23 PL PL03376450A patent/PL376450A1/xx not_active Application Discontinuation
- 2003-10-23 ES ES03809317T patent/ES2306918T3/es not_active Expired - Lifetime
- 2003-10-23 DK DK03809317T patent/DK1558600T3/da active
- 2003-10-23 CA CA002503455A patent/CA2503455A1/en not_active Abandoned
- 2003-10-23 PE PE2003001077A patent/PE20040592A1/es not_active Application Discontinuation
- 2003-10-23 MX MXPA05004375A patent/MXPA05004375A/es not_active Application Discontinuation
- 2003-10-23 DE DE50309807T patent/DE50309807D1/de not_active Expired - Lifetime
- 2003-10-23 JP JP2004545963A patent/JP4401296B2/ja not_active Expired - Fee Related
- 2003-10-23 AU AU2003276156A patent/AU2003276156A1/en not_active Abandoned
- 2003-10-23 WO PCT/EP2003/011762 patent/WO2004037810A1/de active IP Right Grant
- 2003-10-23 EA EA200500600A patent/EA009219B1/ru not_active IP Right Cessation
- 2003-10-24 AR ARP030103889A patent/AR041718A1/es unknown
- 2003-10-24 TW TW092129640A patent/TW200413317A/zh unknown
-
2005
- 2005-03-17 ZA ZA200502248A patent/ZA200502248B/en unknown
- 2005-04-14 IL IL168056A patent/IL168056A0/en unknown
- 2005-04-22 HR HR20050364A patent/HRP20050364A2/hr not_active Application Discontinuation
- 2005-04-25 EC EC2005005747A patent/ECSP055747A/es unknown
- 2005-05-24 CO CO05050511A patent/CO5570704A2/es not_active Application Discontinuation
- 2005-05-24 NO NO20052496A patent/NO20052496L/no not_active Application Discontinuation
Also Published As
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UY28034A1 (es) | 2004-05-31 |
ZA200502248B (en) | 2006-08-30 |
NO20052496D0 (no) | 2005-05-24 |
IL168056A0 (en) | 2009-02-11 |
WO2004037810A1 (de) | 2004-05-06 |
PE20040592A1 (es) | 2004-10-27 |
KR20050074970A (ko) | 2005-07-19 |
HRP20050364A2 (en) | 2006-05-31 |
AR041718A1 (es) | 2005-05-26 |
EA200500600A1 (ru) | 2006-02-24 |
NO20052496L (no) | 2005-06-24 |
ES2306918T3 (es) | 2008-11-16 |
EA009219B1 (ru) | 2007-12-28 |
MXPA05004375A (es) | 2005-07-05 |
CO5570704A2 (es) | 2005-10-31 |
BR0315665A (pt) | 2005-08-30 |
ATE394392T1 (de) | 2008-05-15 |
RS20050311A (en) | 2007-08-03 |
AU2003276156A1 (en) | 2004-05-13 |
CN1708493A (zh) | 2005-12-14 |
EP1558600B1 (de) | 2008-05-07 |
PL376450A1 (en) | 2005-12-27 |
DK1558600T3 (da) | 2008-09-01 |
JP2006516244A (ja) | 2006-06-29 |
CA2503455A1 (en) | 2004-05-06 |
DE50309807D1 (de) | 2008-06-19 |
ECSP055747A (es) | 2005-07-06 |
EP1558600A1 (de) | 2005-08-03 |
DE10250080A1 (de) | 2004-05-13 |
JP4401296B2 (ja) | 2010-01-20 |
TW200413317A (en) | 2004-08-01 |
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