TW200424194A - New substituted nitrogen-containing heterobicycles, the preparation thereof and their use as pharmaceutical compositions - Google Patents

New substituted nitrogen-containing heterobicycles, the preparation thereof and their use as pharmaceutical compositions Download PDF

Info

Publication number: TW200424194A
Authority: TW; Taiwan
Prior art keywords: group; chloro; alkyl; carbonyl; amino
Prior art date: 2002-12-23

Application number

TW092136403A

Other languages

English (en)

Chinese (zh)

Inventor

Henning Priepke

Roland Pfau

Kai Gerlach

Uwe Ries

Wolfgang Wienen

Eckhart Bauer

Herbert Nar

Original Assignee

Boehringer Ingelheim Pharma

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.)

2002-12-23

Filing date

2003-12-22

Publication date

2004-11-16

2003-12-22 Application filed by Boehringer Ingelheim Pharma filed Critical Boehringer Ingelheim Pharma

2004-11-16 Publication of TW200424194A publication Critical patent/TW200424194A/zh

Links

238000002360 preparation method Methods 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 82
239000000203 mixture Substances 0.000 claims abstract description 60
150000003839 salts Chemical class 0.000 claims abstract description 39
108010074860 Factor Xa Proteins 0.000 claims abstract description 8
230000002401 inhibitory effect Effects 0.000 claims abstract description 7
150000007524 organic acids Chemical class 0.000 claims abstract description 7
235000005985 organic acids Nutrition 0.000 claims abstract description 7
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
-1 lactyl Chemical group 0.000 claims description 706
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 343
125000000217 alkyl group Chemical group 0.000 claims description 330
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 240
125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 claims description 201
239000000460 chlorine Substances 0.000 claims description 164
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 157
229910052801 chlorine Inorganic materials 0.000 claims description 148
125000004433 nitrogen atom Chemical group N* 0.000 claims description 128
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 118
229910052757 nitrogen Inorganic materials 0.000 claims description 117
125000001072 heteroaryl group Chemical group 0.000 claims description 109
125000003277 amino group Chemical group 0.000 claims description 107
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 102
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 99
NKLOLMQJDLMZRE-UHFFFAOYSA-N 6-chloro-1h-benzimidazole Chemical compound ClC1=CC=C2N=CNC2=C1 NKLOLMQJDLMZRE-UHFFFAOYSA-N 0.000 claims description 98
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 98
229910052717 sulfur Inorganic materials 0.000 claims description 97
238000006467 substitution reaction Methods 0.000 claims description 96
125000004434 sulfur atom Chemical group 0.000 claims description 96
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 95
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 93
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 91
150000001412 amines Chemical group 0.000 claims description 84
229910052760 oxygen Inorganic materials 0.000 claims description 79
239000001301 oxygen Substances 0.000 claims description 79
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
125000001309 chloro group Chemical group Cl* 0.000 claims description 67
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 61
125000006308 propyl amino group Chemical group 0.000 claims description 58
125000004432 carbon atom Chemical group C* 0.000 claims description 57
125000003545 alkoxy group Chemical group 0.000 claims description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
229910052731 fluorine Inorganic materials 0.000 claims description 53
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 52
125000001841 imino group Chemical group [H]N=* 0.000 claims description 52
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 47
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 46
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 45
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 36
125000003282 alkyl amino group Chemical group 0.000 claims description 33
125000001153 fluoro group Chemical group F* 0.000 claims description 33
125000000304 alkynyl group Chemical group 0.000 claims description 32
125000005842 heteroatom Chemical group 0.000 claims description 32
125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 32
102000017795 Perilipin-1 Human genes 0.000 claims description 29
108010067162 Perilipin-1 Proteins 0.000 claims description 29
239000002253 acid Chemical group 0.000 claims description 29
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 29
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 28
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 27
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 26
239000011737 fluorine Substances 0.000 claims description 26
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 25
JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
125000004429 atom Chemical group 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 22
239000007789 gas Substances 0.000 claims description 22
125000000623 heterocyclic group Chemical group 0.000 claims description 21
150000003254 radicals Chemical class 0.000 claims description 21
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 20
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
125000002950 monocyclic group Chemical group 0.000 claims description 20
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000006239 protecting group Chemical group 0.000 claims description 18
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 16
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 16
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 16
125000002837 carbocyclic group Chemical group 0.000 claims description 14
150000001721 carbon Chemical group 0.000 claims description 14
150000002466 imines Chemical class 0.000 claims description 14
125000002757 morpholinyl group Chemical group 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 13
125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
QHPMUZRQTOYDJQ-UHFFFAOYSA-N 1-chlorobenzimidazole Chemical compound C1=CC=C2N(Cl)C=NC2=C1 QHPMUZRQTOYDJQ-UHFFFAOYSA-N 0.000 claims description 12
125000005605 benzo group Chemical group 0.000 claims description 12
125000000879 imine group Chemical group 0.000 claims description 12
238000001727 in vivo Methods 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 12
229960001404 quinidine Drugs 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
230000036961 partial effect Effects 0.000 claims description 9
125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
229960000948 quinine Drugs 0.000 claims description 8
150000003413 spiro compounds Chemical class 0.000 claims description 8
OPGUZRRLMQSMAQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-phenylbenzimidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3C=CC=CC=3)C2=C1 OPGUZRRLMQSMAQ-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
125000003884 phenylalkyl group Chemical group 0.000 claims description 7
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
239000002023 wood Substances 0.000 claims description 7
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000002993 cycloalkylene group Chemical group 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
KHTZEFSHZJPOTJ-UHFFFAOYSA-N 1h-quinazolin-2-ylidenemethanone Chemical compound C1=CC=C2C=NC(=C=O)NC2=C1 KHTZEFSHZJPOTJ-UHFFFAOYSA-N 0.000 claims description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
238000005859 coupling reaction Methods 0.000 claims description 5
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000005241 heteroarylamino group Chemical group 0.000 claims description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
WZJLGICGNMAUFC-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-fluorene Chemical compound C12=CC=CC=C2CC2=C1CCCC2 WZJLGICGNMAUFC-UHFFFAOYSA-N 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000005336 allyloxy group Chemical group 0.000 claims description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000002843 carboxylic acid group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
150000001924 cycloalkanes Chemical class 0.000 claims description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
150000007857 hydrazones Chemical class 0.000 claims description 4
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
USISRUCGEISZIB-UHFFFAOYSA-N piperidin-3-one Chemical compound O=C1CCCNC1 USISRUCGEISZIB-UHFFFAOYSA-N 0.000 claims description 4
RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 3
POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 3
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
235000001258 Cinchona calisaya Nutrition 0.000 claims description 3
241000282376 Panthera tigris Species 0.000 claims description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
230000008878 coupling Effects 0.000 claims description 3
238000010168 coupling process Methods 0.000 claims description 3
125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000005567 fluorenylene group Chemical group 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims description 3
150000002739 metals Chemical class 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
OQCUGPQOZNYIMV-UHFFFAOYSA-N pyrrolidin-3-ylmethanamine Chemical compound NCC1CCNC1 OQCUGPQOZNYIMV-UHFFFAOYSA-N 0.000 claims description 3
238000006268 reductive amination reaction Methods 0.000 claims description 3
239000002689 soil Substances 0.000 claims description 3
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
229910052723 transition metal Inorganic materials 0.000 claims description 3
150000003624 transition metals Chemical class 0.000 claims description 3
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
UPVQNQSCDWBZFR-UHFFFAOYSA-N 2h-tetrazepine Chemical compound N1C=CC=NN=N1 UPVQNQSCDWBZFR-UHFFFAOYSA-N 0.000 claims description 2
229930194542 Keto Natural products 0.000 claims description 2
241001529936 Murinae Species 0.000 claims description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
150000001409 amidines Chemical class 0.000 claims description 2
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
125000001142 dicarboxylic acid group Chemical group 0.000 claims description 2
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000002496 gastric effect Effects 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
AALUTIYNYXEFNT-UHFFFAOYSA-N trimethylsilane hydroiodide Chemical compound C[SiH](C)C.I AALUTIYNYXEFNT-UHFFFAOYSA-N 0.000 description 1
OKZLYNSHAULDAT-UHFFFAOYSA-N triphenyl(3-triphenylphosphaniumylpropyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OKZLYNSHAULDAT-UHFFFAOYSA-N 0.000 description 1
BIPFTJPEICZJRX-UHFFFAOYSA-N tris(2-methylphenyl)phosphane;hydrochloride Chemical compound Cl.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C BIPFTJPEICZJRX-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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210000001835 viscera Anatomy 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
239000008433 xiaoji Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1

Classifications

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- 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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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/04—Antineoplastic agents specific for metastasis
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/08—Vasodilators for multiple indications
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D495/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Oncology (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

TW092136403A 2002-12-23 2003-12-22 New substituted nitrogen-containing heterobicycles, the preparation thereof and their use as pharmaceutical compositions TW200424194A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10260730A DE10260730A1 (de)	2002-12-23	2002-12-23	Neue substituierte stickstoffhaltige Heterobicyclen, deren Herstellung und deren Verwendung als Arzneimittel

Publications (1)

Publication Number	Publication Date
TW200424194A true TW200424194A (en)	2004-11-16

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ID=32404214

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW092136403A TW200424194A (en)	2002-12-23	2003-12-22	New substituted nitrogen-containing heterobicycles, the preparation thereof and their use as pharmaceutical compositions

Country Status (11)

Country	Link
EP (1)	EP1583757A1 (fr)
JP (1)	JP2006515301A (fr)
AR (1)	AR043685A1 (fr)
AU (1)	AU2003298192A1 (fr)
CA (1)	CA2511349A1 (fr)
CL (1)	CL2003002697A1 (fr)
DE (1)	DE10260730A1 (fr)
PE (1)	PE20040806A1 (fr)
TW (1)	TW200424194A (fr)
UY (1)	UY28143A1 (fr)
WO (1)	WO2004058743A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006047415A2 (fr)	2004-10-26	2006-05-04	Janssen Pharmaceutica, N.V.	Composes inhibiteurs du facteurs xa
EP2220079A2 (fr)	2007-11-15	2010-08-25	Boehringer Ingelheim International GmbH	Amides substitués, leur fabrication et utilisation sous forme de médicaments
CN103265524B (zh) *	2013-05-15	2016-01-20	华东师范大学	β-氨基-2,5-二氧六环内酯衍生物的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9514265D0 (en) *	1995-07-13	1995-09-13	Wellcome Found	Hetrocyclic compounds
PE121699A1 (es)	1997-02-18	1999-12-08	Boehringer Ingelheim Pharma	Heterociclos biciclicos disustituidos como inhibidores de la trombina
US20030114448A1 (en) *	2001-05-31	2003-06-19	Millennium Pharmaceuticals, Inc.	Inhibitors of factor Xa
PE20040804A1 (es) *	2002-12-19	2004-12-31	Boehringer Ingelheim Pharma	DERIVADOS DE CARBOXAMIDAS COMO INHIBIDORES DEL FACTOR Xa

2002
- 2002-12-23 DE DE10260730A patent/DE10260730A1/de not_active Withdrawn
2003
- 2003-12-12 PE PE2003001281A patent/PE20040806A1/es not_active Application Discontinuation
- 2003-12-17 EP EP03795904A patent/EP1583757A1/fr not_active Withdrawn
- 2003-12-17 JP JP2004562769A patent/JP2006515301A/ja not_active Ceased
- 2003-12-17 CA CA002511349A patent/CA2511349A1/fr not_active Abandoned
- 2003-12-17 AU AU2003298192A patent/AU2003298192A1/en not_active Abandoned
- 2003-12-17 WO PCT/EP2003/014378 patent/WO2004058743A1/fr not_active Ceased
- 2003-12-19 CL CL200302697A patent/CL2003002697A1/es unknown
- 2003-12-22 UY UY28143A patent/UY28143A1/es not_active Application Discontinuation
- 2003-12-22 TW TW092136403A patent/TW200424194A/zh unknown
- 2003-12-23 AR ARP030104807A patent/AR043685A1/es unknown

Also Published As

Publication number	Publication date
JP2006515301A (ja)	2006-05-25
DE10260730A1 (de)	2004-07-01
PE20040806A1 (es)	2004-12-23
AU2003298192A1 (en)	2004-07-22
UY28143A1 (es)	2004-07-30
WO2004058743A1 (fr)	2004-07-15
CA2511349A1 (fr)	2004-07-15
AR043685A1 (es)	2005-08-10
CL2003002697A1 (es)	2005-01-14
EP1583757A1 (fr)	2005-10-12

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