ZA200502248B - 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
- ZA200502248B ZA200502248B ZA200502248A ZA200502248A ZA200502248B ZA 200502248 B ZA200502248 B ZA 200502248B ZA 200502248 A ZA200502248 A ZA 200502248A ZA 200502248 A ZA200502248 A ZA 200502248A ZA 200502248 B ZA200502248 B ZA 200502248B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperidin
- group
- denotes
- general formula
- amino
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 229940127597 CGRP antagonist Drugs 0.000 title description 3
- 239000003814 drug Substances 0.000 title 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 230000008878 coupling Effects 0.000 claims 4
- 238000010168 coupling process Methods 0.000 claims 4
- 238000005859 coupling reaction Methods 0.000 claims 4
- 150000003335 secondary amines Chemical class 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 2
- 206010047141 Vasodilatation Diseases 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 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 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 2
- 230000024883 vasodilation Effects 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 241000193403 Clostridium Species 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 206010015150 Erythema Diseases 0.000 claims 1
- 206010060800 Hot flush Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 230000017531 blood circulation Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000004087 circulation Effects 0.000 claims 1
- 230000002950 deficient Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 231100000321 erythema Toxicity 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 210000002200 mouth mucosa Anatomy 0.000 claims 1
- 231100000189 neurotoxic Toxicity 0.000 claims 1
- 230000002887 neurotoxic effect Effects 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 230000037380 skin damage Effects 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 231100000765 toxin Toxicity 0.000 claims 1
- -1 phenylsulphonylimino Chemical group 0.000 description 286
- 229910052757 nitrogen Inorganic materials 0.000 description 47
- 125000004433 nitrogen atom Chemical group N* 0.000 description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
- 125000001153 fluoro group Chemical group F* 0.000 description 35
- 125000000217 alkyl group Chemical group 0.000 description 30
- 229910052801 chlorine Inorganic materials 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 29
- 229910052731 fluorine Inorganic materials 0.000 description 26
- 239000011737 fluorine Substances 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
- 150000001721 carbon Chemical group 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 20
- 125000004076 pyridyl group Chemical group 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
- 125000004663 dialkyl amino group Chemical group 0.000 description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 14
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 14
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 14
- 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 description 14
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- 125000003282 alkyl amino group Chemical group 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 239000003574 free electron Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 9
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 125000001589 carboacyl group Chemical group 0.000 description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 3
- WVKZNHRMECGGGL-UHFFFAOYSA-N 1h-quinolin-2-one Chemical group C1=C=C[C]2NC(=O)C=CC2=C1 WVKZNHRMECGGGL-UHFFFAOYSA-N 0.000 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 2
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical group CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 description 1
- DDDRROQCXMLURP-UHFFFAOYSA-N 4-oxo-4-(4-pyridin-4-ylpiperazin-1-yl)butanal Chemical compound N1=CC=C(C=C1)N1CCN(CC1)C(CCC=O)=O DDDRROQCXMLURP-UHFFFAOYSA-N 0.000 description 1
- YHAKRKUWDJPVAX-UHFFFAOYSA-N 4-oxo-4-[4-(1,2,4-triazol-1-yl)piperidin-1-yl]butanal Chemical compound N1(N=CN=C1)C1CCN(CC1)C(CCC=O)=O YHAKRKUWDJPVAX-UHFFFAOYSA-N 0.000 description 1
- NPHIPKPSBCDCHY-UHFFFAOYSA-N 4-oxo-4-[4-(piperidin-1-ylmethyl)piperidin-1-yl]butanal Chemical compound C1CN(C(=O)CCC=O)CCC1CN1CCCCC1 NPHIPKPSBCDCHY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241001091551 Clio Species 0.000 description 1
- 101150018425 Cr1l gene Proteins 0.000 description 1
- 241000531897 Loma Species 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 description 1
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
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- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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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- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
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- C07—ORGANIC CHEMISTRY
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—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
- 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
- C07D513/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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Applications Claiming Priority (1)
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 |
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ZA200502248B true ZA200502248B (en) | 2006-08-30 |
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ZA200502248A ZA200502248B (en) | 2002-10-25 | 2005-03-17 | Selected CGRP antagonists, method for production and use thereof as medicament |
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EP (1) | EP1558600B1 (no) |
JP (1) | JP4401296B2 (no) |
KR (1) | KR20050074970A (no) |
CN (1) | CN1708493A (no) |
AR (1) | AR041718A1 (no) |
AT (1) | ATE394392T1 (no) |
AU (1) | AU2003276156A1 (no) |
BR (1) | BR0315665A (no) |
CA (1) | CA2503455A1 (no) |
CO (1) | CO5570704A2 (no) |
DE (2) | DE10250080A1 (no) |
DK (1) | DK1558600T3 (no) |
EA (1) | EA009219B1 (no) |
EC (1) | ECSP055747A (no) |
ES (1) | ES2306918T3 (no) |
HR (1) | HRP20050364A2 (no) |
IL (1) | IL168056A0 (no) |
MX (1) | MXPA05004375A (no) |
NO (1) | NO20052496L (no) |
PE (1) | PE20040592A1 (no) |
PL (1) | PL376450A1 (no) |
RS (1) | RS20050311A (no) |
TW (1) | TW200413317A (no) |
UA (1) | UA79323C2 (no) |
UY (1) | UY28034A1 (no) |
WO (1) | WO2004037810A1 (no) |
ZA (1) | ZA200502248B (no) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
AR046787A1 (es) | 2003-12-05 | 2005-12-21 | Bristol Myers Squibb Co | Agentes antimigrana heterociclicos |
DE102004015723A1 (de) * | 2004-03-29 | 2005-10-20 | Boehringer Ingelheim Pharma | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
TW200533398A (en) * | 2004-03-29 | 2005-10-16 | Bristol Myers Squibb Co | Novel therapeutic agents for the treatment of migraine |
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 |
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 |
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 |
WO2006031513A2 (en) * | 2004-09-09 | 2006-03-23 | Merck & Co., Inc. | Aryl spirolactam cgrp receptor antagonists |
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 |
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 |
DE102004063752A1 (de) * | 2004-12-29 | 2006-07-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung ausgewählter CGRP-Antagonisten zur Bekämpfung menopausaler Hitzewallungen |
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 |
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 |
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 |
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 |
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 |
WO2007141285A1 (en) * | 2006-06-08 | 2007-12-13 | Boehringer Ingelheim International Gmbh | Treatment of gastrointestinal disorders with cgrp-antagonists |
DE102007038250A1 (de) | 2007-08-13 | 2009-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Herstellverfahren |
NZ585347A (en) | 2007-10-18 | 2011-09-30 | Boehringer Ingelheim Int | Cgrp antagonists |
EP2065381A1 (de) | 2007-10-18 | 2009-06-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | CGRP Antagonisten |
EP2251338A3 (de) | 2007-11-22 | 2011-06-08 | Boehringer Ingelheim International GmbH | Organische Verbindungen |
CA2794350C (en) | 2008-08-01 | 2014-09-09 | Mitsui Chemicals Agro, Inc. | Amide derivative, pest control agent containing the amide derivative, and pest controlling method |
EP2396081B1 (en) | 2009-02-16 | 2017-04-05 | Nogra Pharma Limited | Alkylamido compounds and uses thereof |
MX364220B (es) | 2012-02-09 | 2019-04-16 | Nogra Pharma Ltd | Metodos de tratamientos de 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 |
ES2902600T3 (es) | 2017-08-16 | 2022-03-29 | Glaxosmithkline Ip Dev Ltd | Compuestos novedosos |
CN111801330B (zh) | 2018-01-26 | 2024-04-05 | 盐野义制药株式会社 | 具有多巴胺d3受体拮抗作用的稠环化合物 |
WO2020161362A1 (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 |
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AU6211499A (en) * | 1998-09-30 | 2000-04-17 | Merck & Co., Inc. | Benzimidazolinyl piperidines as cgrp ligands |
DE19937304C2 (de) * | 1999-08-10 | 2003-08-21 | Boehringer Ingelheim Pharma | Verwendung von CGRP-Antagonisten zur Bekämpfung menopausaler Hitzewallungen |
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2002
- 2002-10-25 DE DE10250080A patent/DE10250080A1/de not_active Withdrawn
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2003
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- 2003-10-23 PL PL03376450A patent/PL376450A1/xx not_active Application Discontinuation
- 2003-10-23 BR BR0315665-6A patent/BR0315665A/pt not_active Expired - Fee Related
- 2003-10-23 EA EA200500600A patent/EA009219B1/ru not_active IP Right Cessation
- 2003-10-23 CN CNA2003801020040A patent/CN1708493A/zh active Pending
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- 2003-10-23 EP EP03809317A patent/EP1558600B1/de not_active Expired - Lifetime
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2005
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- 2005-05-24 NO NO20052496A patent/NO20052496L/no not_active Application Discontinuation
- 2005-05-24 CO CO05050511A patent/CO5570704A2/es not_active Application Discontinuation
Also Published As
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JP4401296B2 (ja) | 2010-01-20 |
EA200500600A1 (ru) | 2006-02-24 |
WO2004037810A1 (de) | 2004-05-06 |
DE10250080A1 (de) | 2004-05-13 |
UA79323C2 (en) | 2007-06-11 |
MXPA05004375A (es) | 2005-07-05 |
AR041718A1 (es) | 2005-05-26 |
KR20050074970A (ko) | 2005-07-19 |
EP1558600A1 (de) | 2005-08-03 |
ES2306918T3 (es) | 2008-11-16 |
NO20052496D0 (no) | 2005-05-24 |
ECSP055747A (es) | 2005-07-06 |
JP2006516244A (ja) | 2006-06-29 |
PE20040592A1 (es) | 2004-10-27 |
HRP20050364A2 (en) | 2006-05-31 |
DE50309807D1 (de) | 2008-06-19 |
EP1558600B1 (de) | 2008-05-07 |
ATE394392T1 (de) | 2008-05-15 |
BR0315665A (pt) | 2005-08-30 |
IL168056A0 (en) | 2009-02-11 |
AU2003276156A1 (en) | 2004-05-13 |
EA009219B1 (ru) | 2007-12-28 |
DK1558600T3 (da) | 2008-09-01 |
CN1708493A (zh) | 2005-12-14 |
NO20052496L (no) | 2005-06-24 |
TW200413317A (en) | 2004-08-01 |
UY28034A1 (es) | 2004-05-31 |
CO5570704A2 (es) | 2005-10-31 |
CA2503455A1 (en) | 2004-05-06 |
PL376450A1 (en) | 2005-12-27 |
RS20050311A (en) | 2007-08-03 |
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