UA80821C2 - 7-aryl-3,9-diazabicyclo (3.3.1)non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases - Google Patents

7-aryl-3,9-diazabicyclo (3.3.1)non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases Download PDF

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Publication number: UA80821C2
Authority: UA; Ukraine
Prior art keywords: phenyl; diazabicyclo; propyl; trifluorophenoxy; acid
Prior art date: 2002-04-29

Application number

UA20041109469A

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English (en)

Ukrainian (uk)

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.)

2002-04-29

Filing date

2003-08-04

Publication date

2007-11-12

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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=29286070&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA80821(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2003-08-04 Application filed filed Critical

2007-11-12 Publication of UA80821C2 publication Critical patent/UA80821C2/uk

Links

206010020772 Hypertension Diseases 0.000 title claims description 9
208000024172 Cardiovascular disease Diseases 0.000 title claims description 4
230000002526 effect on cardiovascular system Effects 0.000 title claims description 3
208000017169 kidney disease Diseases 0.000 title claims description 3
239000002461 renin inhibitor Substances 0.000 title description 11
229940086526 renin-inhibitors Drugs 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims abstract description 417
238000000034 method Methods 0.000 claims abstract description 408
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
241000700159 Rattus Species 0.000 claims description 672
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 605
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 592
239000000203 mixture Substances 0.000 claims description 377
238000011160 research Methods 0.000 claims description 231
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 155
-1 racemates Chemical class 0.000 claims description 149
239000002253 acid Substances 0.000 claims description 146
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 145
239000002904 solvent Substances 0.000 claims description 126
GCJYLAWVUWEHLW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC=C1CNC1CC1 GCJYLAWVUWEHLW-UHFFFAOYSA-N 0.000 claims description 112
SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 claims description 110
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 105
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 82
229910052799 carbon Inorganic materials 0.000 claims description 78
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
125000000217 alkyl group Chemical group 0.000 claims description 55
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 33
BTBDLUOYLCXSMK-UHFFFAOYSA-N n-[(3,5-dimethoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC(OC)=CC(CNC2CC2)=C1 BTBDLUOYLCXSMK-UHFFFAOYSA-N 0.000 claims description 32
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 32
HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 31
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 30
150000007513 acids Chemical class 0.000 claims description 29
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 21
IBVNNEPIXJSRAS-UHFFFAOYSA-N 3-(2-chlorophenyl)propan-1-amine Chemical compound NCCCC1=CC=CC=C1Cl IBVNNEPIXJSRAS-UHFFFAOYSA-N 0.000 claims description 20
UZYPFBRRGVZJNV-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]cyclopropanamine Chemical compound FC1=CC=CC=C1CNC1CC1 UZYPFBRRGVZJNV-UHFFFAOYSA-N 0.000 claims description 20
WYQUCNZBUBLJHN-UHFFFAOYSA-N n-[(2-methylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC=C1CNC1CC1 WYQUCNZBUBLJHN-UHFFFAOYSA-N 0.000 claims description 20
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 description 19
KJYVKUQRRKDPAX-UHFFFAOYSA-N n-[(2,3-dichlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC(CNC2CC2)=C1Cl KJYVKUQRRKDPAX-UHFFFAOYSA-N 0.000 claims description 16
USBAUXJPPHVCTF-UHFFFAOYSA-N n-benzylcyclopropanamine Chemical compound C=1C=CC=CC=1CNC1CC1 USBAUXJPPHVCTF-UHFFFAOYSA-N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
CRIMYHBFDHWKQY-UHFFFAOYSA-N n-[(2,3-dimethylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC(CNC2CC2)=C1C CRIMYHBFDHWKQY-UHFFFAOYSA-N 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
ILHIZUJWNGLALK-UHFFFAOYSA-N n-(2-phenylethyl)cyclopropanamine Chemical compound C1CC1NCCC1=CC=CC=C1 ILHIZUJWNGLALK-UHFFFAOYSA-N 0.000 claims description 12
SBKDFWWYKALTKE-UHFFFAOYSA-N n-[(2-bromophenyl)methyl]cyclopropanamine Chemical compound BrC1=CC=CC=C1CNC1CC1 SBKDFWWYKALTKE-UHFFFAOYSA-N 0.000 claims description 12
CEQDKNLDFWAMEL-UHFFFAOYSA-N n-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound FC(F)(F)C1=CC=CC(CNC2CC2)=C1Cl CEQDKNLDFWAMEL-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
150000001721 carbon Chemical group 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
206010019280 Heart failures Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
LJBFNXZKZYKGFY-UHFFFAOYSA-N n-[(3-methylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC(CNC2CC2)=C1 LJBFNXZKZYKGFY-UHFFFAOYSA-N 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
208000001647 Renal Insufficiency Diseases 0.000 claims description 9
239000000969 carrier Substances 0.000 claims description 9
201000006370 kidney failure Diseases 0.000 claims description 9
CUPDQCKBQJVOMC-UHFFFAOYSA-N n-[(2-fluoro-5-methoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC=C(F)C(CNC2CC2)=C1 CUPDQCKBQJVOMC-UHFFFAOYSA-N 0.000 claims description 9
NUPAMNLYORQZRV-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC=CC(CNC2CC2)=C1 NUPAMNLYORQZRV-UHFFFAOYSA-N 0.000 claims description 9
241000238557 Decapoda Species 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
230000000877 morphologic effect Effects 0.000 claims description 8
ORZRHMRDNOCKDU-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]cyclopropanamine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1CC1 ORZRHMRDNOCKDU-UHFFFAOYSA-N 0.000 claims description 8
VALINFAZSMPKJJ-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC(CNC2CC2)=C1 VALINFAZSMPKJJ-UHFFFAOYSA-N 0.000 claims description 8
XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 8
239000005541 ACE inhibitor Substances 0.000 claims description 7
125000004450 alkenylene group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
206010063897 Renal ischaemia Diseases 0.000 claims description 6
ANCFTHKEGKDXKD-UHFFFAOYSA-N n-[[3-(trifluoromethoxy)phenyl]methyl]cyclopropanamine Chemical compound FC(F)(F)OC1=CC=CC(CNC2CC2)=C1 ANCFTHKEGKDXKD-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
WRRVCXHKEDNRNB-UHFFFAOYSA-N n-[(3,5-difluorophenyl)methyl]cyclopropanamine Chemical compound FC1=CC(F)=CC(CNC2CC2)=C1 WRRVCXHKEDNRNB-UHFFFAOYSA-N 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
208000037803 restenosis Diseases 0.000 claims description 5
230000002792 vascular Effects 0.000 claims description 5
229910052727 yttrium Inorganic materials 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 claims description 4
208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
208000010412 Glaucoma Diseases 0.000 claims description 4
206010018364 Glomerulonephritis Diseases 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
230000006806 disease prevention Effects 0.000 claims description 4
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical group CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
201000001881 impotence Diseases 0.000 claims description 4
208000031225 myocardial ischemia Diseases 0.000 claims description 4
210000000056 organ Anatomy 0.000 claims description 4
235000019260 propionic acid Nutrition 0.000 claims description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
238000002054 transplantation Methods 0.000 claims description 4
125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
101800000734 Angiotensin-1 Proteins 0.000 claims description 3
102400000344 Angiotensin-1 Human genes 0.000 claims description 3
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 claims description 3
210000004165 myocardium Anatomy 0.000 claims description 3
WOHOHPONCSKXSQ-UHFFFAOYSA-N n-ethyl-2-phenylethanamine Chemical compound CCNCCC1=CC=CC=C1 WOHOHPONCSKXSQ-UHFFFAOYSA-N 0.000 claims description 3
238000001356 surgical procedure Methods 0.000 claims description 3
229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
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239000002934 diuretic Substances 0.000 claims description 2
229940030606 diuretics Drugs 0.000 claims description 2
MLHBZVFOTDJTPK-UHFFFAOYSA-N n-methyl-3-phenylpropan-1-amine Chemical compound CNCCCC1=CC=CC=C1 MLHBZVFOTDJTPK-UHFFFAOYSA-N 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
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206010012601 diabetes mellitus Diseases 0.000 claims 3
229960003444 immunosuppressant agent Drugs 0.000 claims 3
230000001861 immunosuppressant effect Effects 0.000 claims 3
239000003018 immunosuppressive agent Substances 0.000 claims 3
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208000035475 disorder Diseases 0.000 claims 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical group CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 claims 2
DTJKAALGEAHUIV-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-methylethanamine Chemical compound CNCCC1=CC=CC=C1Cl DTJKAALGEAHUIV-UHFFFAOYSA-N 0.000 claims 1
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
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239000000219 Sympatholytic Substances 0.000 claims 1
239000012190 activator Substances 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
239000002160 alpha blocker Substances 0.000 claims 1
239000002876 beta blocker Substances 0.000 claims 1
238000007675 cardiac surgery Methods 0.000 claims 1
239000002308 endothelin receptor antagonist Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
229960003975 potassium Drugs 0.000 claims 1
239000002464 receptor antagonist Substances 0.000 claims 1
229940044551 receptor antagonist Drugs 0.000 claims 1
230000000948 sympatholitic effect Effects 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
238000007631 vascular surgery Methods 0.000 claims 1
229940124549 vasodilator Drugs 0.000 claims 1
239000003071 vasodilator agent Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 216
108090000783 Renin Proteins 0.000 abstract description 5
102100028255 Renin Human genes 0.000 abstract description 4
239000003112 inhibitor Substances 0.000 abstract description 4
239000004480 active ingredient Substances 0.000 abstract description 2
YJTZZSKGEPHUTF-UHFFFAOYSA-N 3,9-diazabicyclo[3.3.1]non-4-ene Chemical class C1NC=C2CCCC1N2 YJTZZSKGEPHUTF-UHFFFAOYSA-N 0.000 abstract 1
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 238
238000000746 purification Methods 0.000 description 225
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 161
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 150
230000002829 reductive effect Effects 0.000 description 126
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 106
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MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 description 83
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229940126062 Compound A Drugs 0.000 description 45
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229910052760 oxygen Inorganic materials 0.000 description 17
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230000003197 catalytic effect Effects 0.000 description 13
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235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07D471/08—Bridged 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
- C07D487/08—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Ophthalmology & Optometry (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Gynecology & Obstetrics (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

UA20041109469A 2002-04-29 2003-08-04 7-aryl-3,9-diazabicyclo (3.3.1)non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases UA80821C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP0204705		2002-04-29
PCT/EP2003/003721 WO2003093267A1 (fr)	2002-04-29	2003-04-08	Derives de 7-aryl-3,9-diazabicyclo(3.3.1)non-6-ene et leur utilisation en tant qu'inhibiteurs de renine dans le traitement de l'hypertension, de maladies cardiovasculaires ou renales

Publications (1)

Publication Number	Publication Date
UA80821C2 true UA80821C2 (en)	2007-11-12

Family

ID=29286070

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20041109469A UA80821C2 (en)	2002-04-29	2003-08-04	7-aryl-3,9-diazabicyclo (3.3.1)non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases

Country Status (26)

Country	Link
US (2)	US7427613B2 (fr)
EP (1)	EP1501830B1 (fr)
JP (1)	JP4041123B2 (fr)
KR (1)	KR100783863B1 (fr)
CN (1)	CN1649870A (fr)
AT (1)	ATE527261T1 (fr)
AU (1)	AU2003233963B2 (fr)
BR (1)	BR0309498A (fr)
CA (1)	CA2483241C (fr)
CL (1)	CL2003002042A1 (fr)
CO (1)	CO5631443A2 (fr)
EC (1)	ECSP045378A (fr)
ES (1)	ES2372931T3 (fr)
HR (1)	HRP20041132A2 (fr)
IL (1)	IL164767A0 (fr)
IS (1)	IS7545A (fr)
MA (1)	MA27305A1 (fr)
MX (1)	MXPA04010608A (fr)
NO (1)	NO20045042L (fr)
NZ (1)	NZ536750A (fr)
PL (1)	PL372141A1 (fr)
RU (1)	RU2343153C2 (fr)
TW (1)	TW200514786A (fr)
UA (1)	UA80821C2 (fr)
WO (1)	WO2003093267A1 (fr)
ZA (1)	ZA200408283B (fr)

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CA2521951A1 (fr) *	2003-04-28	2004-11-11	Actelion Pharmaceuticals Ltd	Derives de diazabicyclononene et de tetrahydropyridine utilises comme inhibiteurs de la renine
WO2004096803A1 (fr) *	2003-04-30	2004-11-11	Actelion Pharmaceuticals Ltd	Derives d'azabicyclononene
MXPA05011497A (es) *	2003-04-30	2005-12-15	Actelion Pharmaceuticals Ltd	Derivados de tropano y su uso como inhibidores de la enzima de conversion de angiotensina (ace).
US20060258648A1 (en) *	2003-04-30	2006-11-16	Olivier Bezencon	9-Azabicyclo'3.3.1 inon-6-ee derivatives with a heteroatom at the 3-position as renin inhibitors
AU2004233577A1 (en) *	2003-05-02	2004-11-11	Actelion Pharmaceuticals Ltd.	Diazabicyclononene derivatives
WO2004105762A1 (fr) *	2003-05-30	2004-12-09	Actelion Pharmaceuticals Ltd	Utilisation medicale de derives de diazabicyclononene utilises comme inhibiteurs des proteases aspartiques parasites
US20080234305A1 (en) *	2003-10-09	2008-09-25	Olivier Bezencon	Novel Tetrahydropyridine Derivatives
AU2004283821A1 (en) *	2003-10-13	2005-05-06	Actelion Pharmaceuticals Ltd.	Diazabicyclononene derivatives and their use as renin inhibitors
CN1930170A (zh) *	2003-10-23	2007-03-14	埃科特莱茵药品有限公司	二氮杂二环壬烯及四氢吡啶衍生物用作肾素抑制剂
AU2004295092A1 (en) *	2003-12-05	2005-06-16	Actelion Pharmaceuticals Ltd.	Azabicyclooctene and other tetrahydropyridine derivatives with a new side-chain
WO2005054243A1 (fr) *	2003-12-05	2005-06-16	Actelion Pharmaceuticals Ltd	Derives de diazabicyclononene et leur utilisation en tant qu'inhibiteurs de la renine
WO2006021403A1 (fr) *	2004-08-25	2006-03-02	Actelion Pharmaceuticals Ltd	Dérivés du bicyclononène
WO2006021399A2 (fr) *	2004-08-25	2006-03-02	Actelion Pharmaceuticals Ltd	Derives de bicyclononene
WO2006021401A2 (fr) *	2004-08-25	2006-03-02	Actelion Pharmaceuticals Ltd	Derives de bicyclononene
AU2005276624B2 (en) *	2004-08-25	2011-09-29	Actelion Pharmaceuticals Ltd.	Bicyclononene derivatives as renin inhibitors
TW200634014A (en) *	2004-12-08	2006-10-01	Actelion Pharmaceuticals Ltd	Novel diazabicyclononene derivative
WO2006063610A1 (fr) *	2004-12-17	2006-06-22	Actelion Pharmaceuticals Ltd	Dérivés de diazabicyclononène substitués par des groupements hétéroaryle
GB0428526D0 (en)	2004-12-30	2005-02-09	Novartis Ag	Organic compounds
EP1846407B1 (fr) *	2005-01-28	2011-06-29	Actelion Pharmaceuticals Ltd.	Acide 7-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxylique cyclopropyl-(2,3-dimethylbenzyl)amide utilisé comme inhibiteur de la renine pour le traitement de l'hypertension
CA2608212A1 (fr) *	2005-05-27	2006-12-07	Actelion Pharmaceuticals Ltd	Nouveaux derives d'amide d'acide piperidine carboxylique
GB0514203D0 (en)	2005-07-11	2005-08-17	Novartis Ag	Organic compounds
EP2420491B1 (fr)	2005-12-30	2013-07-03	Novartis AG	Dérivés de pipéridine 3,5-substitués en tant qu'inhibiteurs de rénine
JP2009526767A (ja)	2006-02-02	2009-07-23	アクテリオンファーマシューティカルズリミテッド	新規二級アミン
JP2009529033A (ja) *	2006-03-08	2009-08-13	アクテリオンファーマシューティカルズリミテッド	新規アミン
WO2008141462A1 (fr)	2007-05-24	2008-11-27	Merck Frosst Canada Ltd.	Nouveaux inhibiteurs de rhénine
BRPI0813900A2 (pt)	2007-06-25	2014-12-30	Novartis Ag	Derivados de n5-(2-etoxietil)-n3-(2-piridinil)-3,5-piperidinodicarboxa mida para uso como inibidores de renina
WO2009023964A1 (fr)	2007-08-20	2009-02-26	Merck Frosst Canada Ltd.	Inhibiteurs de la rénine
BRPI0912388A2 (pt)	2008-05-05	2017-09-26	Merck Frosst Canada Ltd	composto, forma cristalina, processo para preparar compostos, composição farmacêutica, e, uso de um composto, e, método para o tratamento ou profilaxia de doenças
CN109721613B (zh) *	2017-10-27	2021-07-30	四川科伦博泰生物医药股份有限公司	含季铵离子的大环酰胺化合物及其药物组合物和用途

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US3509161A (en) *	1967-07-10	1970-04-28	Boehringer & Soehne Gmbh	3-phenyl-granatene-(2)-derivatives
GB9020927D0 (en)	1990-09-26	1990-11-07	Beecham Group Plc	Pharmaceuticals
US5268361A (en) *	1991-06-07	1993-12-07	Sri International	Hydroxyazido derivatives and related compounds as renin inhibitors
US5374719A (en) *	1993-06-04	1994-12-20	Eli Lilly And Company	Process for converting loracarbef dihydrate to loracarbef monohydrate
IL123293A (en) *	1995-09-07	2003-06-24	Hoffmann La Roche	Piperidine derivatives, their preparation and pharmaceutical compositions containing them
WO1998039328A1 (fr)	1997-03-03	1998-09-11	F.Hoffmann-La Roche Ag	2,4,-diaminopyrimidines substitues
US20060223795A1 (en) *	2003-05-02	2006-10-05	Oliver Bezencon	Novel diazabicyclononene derivatives
WO2005054243A1 (fr) *	2003-12-05	2005-06-16	Actelion Pharmaceuticals Ltd	Derives de diazabicyclononene et leur utilisation en tant qu'inhibiteurs de la renine

2003
- 2003-04-08 MX MXPA04010608A patent/MXPA04010608A/es not_active Application Discontinuation
- 2003-04-08 WO PCT/EP2003/003721 patent/WO2003093267A1/fr not_active Ceased
- 2003-04-08 JP JP2004501406A patent/JP4041123B2/ja not_active Expired - Fee Related
- 2003-04-08 KR KR1020047016845A patent/KR100783863B1/ko not_active Expired - Fee Related
- 2003-04-08 AU AU2003233963A patent/AU2003233963B2/en not_active Ceased
- 2003-04-08 CA CA2483241A patent/CA2483241C/fr not_active Expired - Fee Related
- 2003-04-08 CN CNA038097664A patent/CN1649870A/zh active Pending
- 2003-04-08 AT AT03727287T patent/ATE527261T1/de not_active IP Right Cessation
- 2003-04-08 IL IL16476703A patent/IL164767A0/xx unknown
- 2003-04-08 RU RU2004134320/04A patent/RU2343153C2/ru not_active IP Right Cessation
- 2003-04-08 HR HR20041132A patent/HRP20041132A2/xx not_active Application Discontinuation
- 2003-04-08 NZ NZ536750A patent/NZ536750A/xx unknown
- 2003-04-08 ES ES03727287T patent/ES2372931T3/es not_active Expired - Lifetime
- 2003-04-08 EP EP03727287A patent/EP1501830B1/fr not_active Expired - Lifetime
- 2003-04-08 BR BR0309498-7A patent/BR0309498A/pt not_active IP Right Cessation
- 2003-04-08 PL PL03372141A patent/PL372141A1/xx not_active Application Discontinuation
- 2003-04-08 US US10/513,103 patent/US7427613B2/en not_active Expired - Fee Related
- 2003-08-04 UA UA20041109469A patent/UA80821C2/uk unknown
- 2003-10-10 CL CL200302042A patent/CL2003002042A1/es unknown
- 2003-10-23 TW TW092129421A patent/TW200514786A/zh unknown
2004
- 2004-10-13 ZA ZA200408283A patent/ZA200408283B/xx unknown
- 2004-10-22 MA MA27914A patent/MA27305A1/fr unknown
- 2004-10-22 CO CO04106347A patent/CO5631443A2/es not_active Application Discontinuation
- 2004-10-22 EC EC2004005378A patent/ECSP045378A/es unknown
- 2004-11-19 NO NO20045042A patent/NO20045042L/no not_active Application Discontinuation
- 2004-11-22 IS IS7545A patent/IS7545A/is unknown
2008
- 2008-07-07 US US12/168,666 patent/US20080312242A1/en not_active Abandoned

Also Published As

Publication number	Publication date
KR20040101546A (ko)	2004-12-02
NZ536750A (en)	2007-02-23
MXPA04010608A (es)	2004-12-13
US20050176700A1 (en)	2005-08-11
CL2003002042A1 (es)	2005-02-04
ECSP045378A (es)	2004-11-26
CA2483241C (fr)	2011-05-31
HRP20041132A2 (en)	2006-07-31
AU2003233963A1 (en)	2003-11-17
IL164767A0 (en)	2005-12-18
US20080312242A1 (en)	2008-12-18
CN1649870A (zh)	2005-08-03
BR0309498A (pt)	2005-02-15
EP1501830A1 (fr)	2005-02-02
TW200514786A (en)	2005-05-01
US7427613B2 (en)	2008-09-23
NO20045042L (no)	2004-11-19
ES2372931T3 (es)	2012-01-27
EP1501830B1 (fr)	2011-10-05
ZA200408283B (en)	2006-05-31
JP4041123B2 (ja)	2008-01-30
CA2483241A1 (fr)	2003-11-13
KR100783863B1 (ko)	2007-12-10
RU2004134320A (ru)	2005-08-27
JP2005527602A (ja)	2005-09-15
PL372141A1 (en)	2005-07-11
AU2003233963B2 (en)	2008-09-11
IS7545A (is)	2004-11-22
ATE527261T1 (de)	2011-10-15
CO5631443A2 (es)	2006-04-28
WO2003093267A1 (fr)	2003-11-13
MA27305A1 (fr)	2005-05-02
RU2343153C2 (ru)	2009-01-10

Publication	Publication Date	Title
UA80821C2 (en)	2007-11-12	7-aryl-3,9-diazabicyclo (3.3.1)non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases
EP1223170B1 (fr)	2005-12-28	Composes de pyrimidine-5-carboxamide, procede de preparation et d'utilisation desdits composes
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JP2021500330A (ja)	2021-01-07	Ｐａｄ阻害剤としてのイミダゾ−ピリジン化合物
EP2379548B1 (fr)	2016-03-09	Triazolopyridines en tant qu'inhibiteurs de phosphodiestérase pour le traitement de maladies du derme
CN102216301B (zh)	2014-12-10	含氮杂环抗菌化合物与其它抗菌化合物的新型组合及该组合作为药剂的用途
US20090215778A1 (en)	2009-08-27	Alpha-substituted Arylmethyl Piperazine Pyrazolo [1,5-alpha]Pyrimidine Amide Derivatives
EA020816B1 (ru)	2015-01-30	Ингибиторы вирусов flaviviridae
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