ZA200510040B - Cyclic tertiary amine compound - Google Patents
Cyclic tertiary amine compound Download PDFInfo
- Publication number
- ZA200510040B ZA200510040B ZA200510040A ZA200510040A ZA200510040B ZA 200510040 B ZA200510040 B ZA 200510040B ZA 200510040 A ZA200510040 A ZA 200510040A ZA 200510040 A ZA200510040 A ZA 200510040A ZA 200510040 B ZA200510040 B ZA 200510040B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- fluorophenyl
- pharmacologically acceptable
- acceptable salt
- pyridin
- Prior art date
Links
- -1 Cyclic tertiary amine compound Chemical class 0.000 title claims description 201
- 125000001424 substituent group Chemical group 0.000 claims description 175
- 150000001875 compounds Chemical class 0.000 claims description 112
- 150000003839 salts Chemical class 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 22
- 102000004127 Cytokines Human genes 0.000 claims description 19
- 108090000695 Cytokines Proteins 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
- 230000002757 inflammatory effect Effects 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 241001465754 Metazoa Species 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 11
- 230000000069 prophylactic effect Effects 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 9
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 229940030966 pyrrole Drugs 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010037660 Pyrexia Diseases 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 208000006454 hepatitis Diseases 0.000 claims description 5
- 231100000283 hepatitis Toxicity 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- KKXLACLYOOHKCN-UHFFFAOYSA-N 4-[2-(3-chloro-4-fluorophenyl)-4-[1-[2-(4-methylsulfinylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(S(=O)C)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=C(Cl)C(F)=CC=2)C=2C=CN=CC=2)CC1 KKXLACLYOOHKCN-UHFFFAOYSA-N 0.000 claims description 2
- ZOJUBGWWGUUXLA-UHFFFAOYSA-N 4-[2-[4-[3-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrazol-5-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CCN1CC=C(C=2C(=C(NN=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 ZOJUBGWWGUUXLA-UHFFFAOYSA-N 0.000 claims description 2
- FVPVBEGIVGYCKF-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 FVPVBEGIVGYCKF-UHFFFAOYSA-N 0.000 claims description 2
- YIEIAZHYVVQHSM-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 YIEIAZHYVVQHSM-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- ALVLVFDDXBGZHL-UHFFFAOYSA-N n-ethyl-4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]benzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 ALVLVFDDXBGZHL-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- DFUNDQUVVSPSJZ-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-4-[1-[2-[4-(2-methoxyethylsulfonyl)phenyl]ethyl]-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(S(=O)(=O)CCOC)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 DFUNDQUVVSPSJZ-UHFFFAOYSA-N 0.000 claims 1
- CJEXEYYETZPECD-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 CJEXEYYETZPECD-UHFFFAOYSA-N 0.000 claims 1
- BHGDFJSOHWGNBK-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 BHGDFJSOHWGNBK-UHFFFAOYSA-N 0.000 claims 1
- MEJUFDKUAMYEIS-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 MEJUFDKUAMYEIS-UHFFFAOYSA-N 0.000 claims 1
- AZIVZJVODAYEBI-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)C)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 AZIVZJVODAYEBI-UHFFFAOYSA-N 0.000 claims 1
- YWCASDVQVPIRNN-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n-propylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 YWCASDVQVPIRNN-UHFFFAOYSA-N 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000003907 antipyretic analgesic agent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000004793 spatially offset Raman spectroscopy Methods 0.000 claims 1
- 238000013519 translation Methods 0.000 description 23
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000002098 pyridazinyl group Chemical group 0.000 description 5
- 108010063738 Interleukins Proteins 0.000 description 4
- 102000015696 Interleukins Human genes 0.000 description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000001786 isothiazolyl group Chemical group 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 102000003390 tumor necrosis factor Human genes 0.000 description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- 108090001005 Interleukin-6 Proteins 0.000 description 2
- 108090001007 Interleukin-8 Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 description 2
- 230000002188 osteogenic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 1
- LRGZZEOWQURWFK-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroisoquinoline Chemical compound C1NCCC2CCCC=C21 LRGZZEOWQURWFK-UHFFFAOYSA-N 0.000 description 1
- CEKSPMMCISUSTR-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroquinoline Chemical compound C1CCC2CCCNC2=C1 CEKSPMMCISUSTR-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 description 1
- ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical group C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- JNQPBUFTGVJZAU-UHFFFAOYSA-N 4-[2-(3-chloro-4-fluorophenyl)-4-[1-[2-(4-methylsulfonylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=C(Cl)C(F)=CC=2)C=2C=CN=CC=2)CC1 JNQPBUFTGVJZAU-UHFFFAOYSA-N 0.000 description 1
- WJDBZZUDGFGXKR-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)C=CN1 WJDBZZUDGFGXKR-UHFFFAOYSA-N 0.000 description 1
- AITJDKZMEFFFPP-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-4-[1-[2-(4-methylsulfonylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 AITJDKZMEFFFPP-UHFFFAOYSA-N 0.000 description 1
- HLDHXNANHUVSRV-UHFFFAOYSA-N 4-[2-[4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1h-pyrrol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1CCN1CC=C(C=2C(=C(NC=2)C=2C=CC(F)=CC=2)C=2C=CN=CC=2)CC1 HLDHXNANHUVSRV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100232929 Caenorhabditis elegans pat-4 gene Proteins 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 239000002988 disease modifying antirheumatic drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000002997 osteoclast Anatomy 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003165991 | 2003-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200510040B true ZA200510040B (en) | 2006-09-27 |
Family
ID=33549242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200510040A ZA200510040B (en) | 2003-06-11 | 2005-12-09 | Cyclic tertiary amine compound |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20070049620A1 (fr) |
| EP (1) | EP1632488A1 (fr) |
| KR (1) | KR20060017865A (fr) |
| CN (1) | CN1863793A (fr) |
| AU (1) | AU2004247560B2 (fr) |
| BR (1) | BRPI0411221A (fr) |
| CA (1) | CA2528929A1 (fr) |
| IL (1) | IL172338A0 (fr) |
| MX (1) | MXPA05013584A (fr) |
| NO (1) | NO20060142L (fr) |
| RU (1) | RU2006100301A (fr) |
| TW (1) | TW200508215A (fr) |
| WO (1) | WO2004111037A1 (fr) |
| ZA (1) | ZA200510040B (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050159444A1 (en) * | 2002-07-19 | 2005-07-21 | Sankyo Company, Limited | Bicyclic unsaturated tertiary amine compounds |
| ITMI20110713A1 (it) * | 2011-04-29 | 2012-10-30 | Bracco Imaging Spa | Processo per la preparazione di un derivato solfatato di3,5-diiodo-o-[3-iodofenil]-l-tirosina |
| JP5157916B2 (ja) | 2007-01-26 | 2013-03-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| US20090054392A1 (en) * | 2007-08-20 | 2009-02-26 | Wyeth | Naphthylpyrimidine, naphthylpyrazine and naphthylpyridazine analogs and their use as agonists of the wnt-beta-catenin cellular messaging system |
| US7868001B2 (en) * | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| RU2014107744A (ru) | 2011-07-29 | 2015-09-10 | Тайсо Фармасьютикал Ко., Лтд. | Амидиновое соединение или его соль |
| AU2014232383B2 (en) | 2013-03-15 | 2019-01-17 | Epigen Biosciences, Inc. | Heterocyclic compounds useful in the treatment of disease |
| KR102672512B1 (ko) | 2018-09-12 | 2024-06-10 | 노파르티스 아게 | 항바이러스 피리도피라진디온 화합물 |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| CA3121202A1 (fr) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Composes pyrrole et pyrazole et leurs procedes d'utilisation |
| US11384083B2 (en) | 2019-02-15 | 2022-07-12 | Incyte Corporation | Substituted spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′h)-ones as CDK2 inhibitors |
| US11472791B2 (en) | 2019-03-05 | 2022-10-18 | Incyte Corporation | Pyrazolyl pyrimidinylamine compounds as CDK2 inhibitors |
| WO2020205560A1 (fr) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Composés sulfonylamides utilisés comme inhibiteurs de la cdk2 |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| US11440914B2 (en) | 2019-05-01 | 2022-09-13 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| JP2023509260A (ja) | 2019-08-14 | 2023-03-08 | インサイト・コーポレイション | Ｃｄｋ２阻害剤としてのイミダゾリルピリミジニルアミン化合物 |
| AU2020353055B2 (en) | 2019-09-26 | 2024-03-07 | Gilead Sciences, Inc. | Antiviral pyrazolopyridinone compounds |
| AR120184A1 (es) | 2019-10-11 | 2022-02-02 | Incyte Corp | Aminas bicíclicas como inhibidoras de la cdk2 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7122666B2 (en) * | 1999-07-21 | 2006-10-17 | Sankyo Company, Limited | Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses |
| WO2001034632A2 (fr) * | 1999-11-12 | 2001-05-17 | Merck & Co., Inc. | Derives de piperidyle diaryle pyrrole a substitution hydroxy aliphatique en tant qu'agents antiprotozoaires |
| AU1596101A (en) * | 1999-11-12 | 2001-06-06 | Merck & Co., Inc. | Aliphatic amine substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents |
| DE60026350T2 (de) * | 1999-11-12 | 2006-11-09 | Merck & Co., Inc. | Diaryl piperidyl-pyrrol-derivate als antiprotozoenmittel |
| EP1361225B1 (fr) * | 2001-01-22 | 2007-11-07 | Sankyo Company, Limited | Composes substitues avec des groupes amines bicycliques |
| US20050159444A1 (en) * | 2002-07-19 | 2005-07-21 | Sankyo Company, Limited | Bicyclic unsaturated tertiary amine compounds |
-
2004
- 2004-06-10 MX MXPA05013584A patent/MXPA05013584A/es unknown
- 2004-06-10 KR KR1020057023731A patent/KR20060017865A/ko not_active Application Discontinuation
- 2004-06-10 BR BRPI0411221-0A patent/BRPI0411221A/pt not_active IP Right Cessation
- 2004-06-10 CA CA002528929A patent/CA2528929A1/fr not_active Abandoned
- 2004-06-10 TW TW093116667A patent/TW200508215A/zh unknown
- 2004-06-10 RU RU2006100301/04A patent/RU2006100301A/ru not_active Application Discontinuation
- 2004-06-10 AU AU2004247560A patent/AU2004247560B2/en not_active Ceased
- 2004-06-10 CN CNA2004800222942A patent/CN1863793A/zh active Pending
- 2004-06-10 WO PCT/JP2004/008492 patent/WO2004111037A1/fr not_active Application Discontinuation
- 2004-06-10 EP EP04746020A patent/EP1632488A1/fr not_active Withdrawn
-
2005
- 2005-12-01 IL IL172338A patent/IL172338A0/en unknown
- 2005-12-09 ZA ZA200510040A patent/ZA200510040B/en unknown
- 2005-12-12 US US11/301,296 patent/US20070049620A1/en not_active Abandoned
-
2006
- 2006-01-10 NO NO20060142A patent/NO20060142L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1632488A1 (fr) | 2006-03-08 |
| AU2004247560B2 (en) | 2007-11-29 |
| RU2006100301A (ru) | 2006-07-10 |
| TW200508215A (en) | 2005-03-01 |
| CA2528929A1 (fr) | 2004-12-23 |
| KR20060017865A (ko) | 2006-02-27 |
| MXPA05013584A (es) | 2006-03-09 |
| BRPI0411221A (pt) | 2006-07-18 |
| US20070049620A1 (en) | 2007-03-01 |
| IL172338A0 (en) | 2009-02-11 |
| WO2004111037A1 (fr) | 2004-12-23 |
| AU2004247560A1 (en) | 2004-12-23 |
| NO20060142L (no) | 2006-03-09 |
| CN1863793A (zh) | 2006-11-15 |
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