ZA200510040B - Cyclic tertiary amine compound - Google Patents

Cyclic tertiary amine compound Download PDF

Info

Publication number: ZA200510040B
Authority: ZA; South Africa
Prior art keywords: group; fluorophenyl; pharmacologically acceptable; acceptable salt; pyridin
Prior art date: 2003-06-11

Application number

ZA200510040A

Other languages

English (en)

Inventor

Tomio Kimura

Akira Nako

Takaichi Shimozato

Nobuyuki Ohkawa

Takayoshi Nagasaki

Original Assignee

Sankyo Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-06-11

Filing date

2005-12-09

Publication date

2006-09-27

2005-12-09 Application filed by Sankyo Co filed Critical Sankyo Co

2006-09-27 Publication of ZA200510040B publication Critical patent/ZA200510040B/en

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

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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
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- 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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- 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

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Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
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Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
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ZA200510040A 2003-06-11 2005-12-09 Cyclic tertiary amine compound ZA200510040B (en)

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

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ID=33549242

Family Applications (1)

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ZA200510040A ZA200510040B (en)	2003-06-11	2005-12-09	Cyclic tertiary amine compound

Country Status (14)

Country	Link
US (1)	US20070049620A1 (pt)
EP (1)	EP1632488A1 (pt)
KR (1)	KR20060017865A (pt)
CN (1)	CN1863793A (pt)
AU (1)	AU2004247560B2 (pt)
BR (1)	BRPI0411221A (pt)
CA (1)	CA2528929A1 (pt)
IL (1)	IL172338A0 (pt)
MX (1)	MXPA05013584A (pt)
NO (1)	NO20060142L (pt)
RU (1)	RU2006100301A (pt)
TW (1)	TW200508215A (pt)
WO (1)	WO2004111037A1 (pt)
ZA (1)	ZA200510040B (pt)

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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
ES2563232T3 (es)	2011-07-29	2016-03-11	Taisho Pharmaceutical Co., Ltd.	Compuesto de amidina o sal del mismo
SG11201507459YA (en)	2013-03-15	2015-10-29	Epigen Biosciences Inc	Heterocyclic compounds useful in the treatment of disease
AU2019339777B2 (en)	2018-09-12	2022-09-01	Novartis Ag	Antiviral pyridopyrazinedione compounds
US11066404B2 (en)	2018-10-11	2021-07-20	Incyte Corporation	Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors
EP3886854A4 (en)	2018-11-30	2022-07-06	Nuvation Bio Inc.	Pyrrole and pyrazole compounds and methods of use thereof
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
TW202100520A (zh)	2019-03-05	2021-01-01	美商英塞特公司	作為cdk2 抑制劑之吡唑基嘧啶基胺化合物
WO2020205560A1 (en)	2019-03-29	2020-10-08	Incyte Corporation	Sulfonylamide compounds as cdk2 inhibitors
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
CN116348458A (zh)	2019-08-14	2023-06-27	因赛特公司	作为cdk2抑制剂的咪唑基嘧啶基胺化合物
US11667613B2 (en)	2019-09-26	2023-06-06	Novartis Ag	Antiviral pyrazolopyridinone compounds
CN119930611A (zh)	2019-10-11	2025-05-06	因赛特公司	作为cdk2抑制剂的双环胺
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

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US7122666B2 (en) *	1999-07-21	2006-10-17	Sankyo Company, Limited	Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
AU1596101A (en) *	1999-11-12	2001-06-06	Merck & Co., Inc.	Aliphatic amine substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents
AU1590501A (en) *	1999-11-12	2001-06-06	Merck & Co., Inc.	Aliphatic hydroxy 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
DE60223339T2 (de) *	2001-01-22	2008-08-28	Sankyo Co., Ltd.	Durch bicyclische aminogruppen substituierte verbindungen
US20050159444A1 (en) *	2002-07-19	2005-07-21	Sankyo Company, Limited	Bicyclic unsaturated tertiary amine compounds

2004
- 2004-06-10 WO PCT/JP2004/008492 patent/WO2004111037A1/ja not_active Ceased
- 2004-06-10 AU AU2004247560A patent/AU2004247560B2/en not_active Ceased
- 2004-06-10 CN CNA2004800222942A patent/CN1863793A/zh active Pending
- 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 KR KR1020057023731A patent/KR20060017865A/ko not_active Withdrawn
- 2004-06-10 MX MXPA05013584A patent/MXPA05013584A/es unknown
- 2004-06-10 EP EP04746020A patent/EP1632488A1/en not_active Withdrawn
- 2004-06-10 CA CA002528929A patent/CA2528929A1/en not_active Abandoned
- 2004-06-10 BR BRPI0411221-0A patent/BRPI0411221A/pt not_active IP Right Cessation
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
RU2006100301A (ru)	2006-07-10
AU2004247560A1 (en)	2004-12-23
WO2004111037A1 (ja)	2004-12-23
AU2004247560B2 (en)	2007-11-29
MXPA05013584A (es)	2006-03-09
KR20060017865A (ko)	2006-02-27
NO20060142L (no)	2006-03-09
IL172338A0 (en)	2009-02-11
CA2528929A1 (en)	2004-12-23
EP1632488A1 (en)	2006-03-08
US20070049620A1 (en)	2007-03-01
BRPI0411221A (pt)	2006-07-18
CN1863793A (zh)	2006-11-15
TW200508215A (en)	2005-03-01

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