SK286687B6 - Sulfónamidy, spôsob ich výroby, medziprodukty, liečivo a farmaceutická kompozícia s ich obsahom - Google Patents

Sulfónamidy, spôsob ich výroby, medziprodukty, liečivo a farmaceutická kompozícia s ich obsahom Download PDF

Info

Publication number: SK286687B6
Authority: SK; Slovakia
Prior art keywords: group; amino; carbonyl; alkyl; sulfonyl
Prior art date: 2000-03-23

Application number

SK1351-2002A

Other languages

English (en)

Slovak (sk)

Other versions

SK13512002A3 (sk

Inventor

Jean-Michel Altenburger

G�Rard Cremer

Gilbert Lassalle

Mostafa Matrougui

Original Assignee

Sanofi - Aventis

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.)

2000-03-23

Filing date

2001-03-22

Publication date

2009-03-05

2001-03-22 Application filed by Sanofi - Aventis filed Critical Sanofi - Aventis

2003-03-04 Publication of SK13512002A3 publication Critical patent/SK13512002A3/sk

2009-03-05 Publication of SK286687B6 publication Critical patent/SK286687B6/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 138
238000000034 method Methods 0.000 title claims description 22
238000004519 manufacturing process Methods 0.000 title claims description 4
239000003814 drug Substances 0.000 title claims description 3
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
150000003456 sulfonamides Chemical class 0.000 title claims 4
-1 1,2,3,6-tetrahydropyridinyl group Chemical group 0.000 claims abstract description 182
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 33
238000002360 preparation method Methods 0.000 claims abstract description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
125000003277 amino group Chemical group 0.000 claims abstract description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000000543 intermediate Substances 0.000 claims abstract 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 103
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 99
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 85
239000000203 mixture Substances 0.000 claims description 79
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 69
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 54
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 51
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 51
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 43
LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 39
125000005843 halogen group Chemical group 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 31
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 19
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 11
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 10
239000004305 biphenyl Substances 0.000 claims description 10
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000005936 piperidyl group Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
229940124530 sulfonamide Drugs 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims description 5
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
238000003786 synthesis reaction Methods 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
150000001413 amino acids Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229940125898 compound 5 Drugs 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
229910052721 tungsten Inorganic materials 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims 1
125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
125000005942 tetrahydropyridyl group Chemical group 0.000 claims 1
239000003146 anticoagulant agent Substances 0.000 abstract description 3
DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical class NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 abstract description 2
230000001225 therapeutic effect Effects 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
125000003386 piperidinyl group Chemical group 0.000 abstract 2
229940127219 anticoagulant drug Drugs 0.000 abstract 1
229960004676 antithrombotic agent Drugs 0.000 abstract 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
239000000243 solution Substances 0.000 description 109
239000011541 reaction mixture Substances 0.000 description 60
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
230000008018 melting Effects 0.000 description 36
238000002844 melting Methods 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
229910052938 sodium sulfate Inorganic materials 0.000 description 31
235000011152 sodium sulphate Nutrition 0.000 description 31
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 16
238000000746 purification Methods 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229910052786 argon Inorganic materials 0.000 description 14
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
229910052763 palladium Inorganic materials 0.000 description 13
238000010898 silica gel chromatography Methods 0.000 description 13
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 12
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
239000012267 brine Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
VHWJSJBTUWUEAL-UHFFFAOYSA-N propanamide;hydrochloride Chemical compound Cl.CCC(N)=O VHWJSJBTUWUEAL-UHFFFAOYSA-N 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
229910021529 ammonia Inorganic materials 0.000 description 9
239000007787 solid Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
108090000190 Thrombin Proteins 0.000 description 5
208000007536 Thrombosis Diseases 0.000 description 5
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
239000002243 precursor Chemical group 0.000 description 5
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
229960004072 thrombin Drugs 0.000 description 5
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 4
230000002785 anti-thrombosis Effects 0.000 description 4
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
UFDULEKOJAEIRI-UHFFFAOYSA-N (2-acetyloxy-3-iodophenyl) acetate Chemical compound CC(=O)OC1=CC=CC(I)=C1OC(C)=O UFDULEKOJAEIRI-UHFFFAOYSA-N 0.000 description 3
YSJXIXMSVYWFFB-UQKRIMTDSA-N (2s)-2-amino-5-(5-aminopyridin-2-yl)-1-[4-(difluoromethylidene)piperidin-1-yl]pentan-1-one;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCC(CC1)=C(F)F)CCC1=CC=C(N)C=N1 YSJXIXMSVYWFFB-UQKRIMTDSA-N 0.000 description 3
UOYFNFYECDTFDW-RSAXXLAASA-N (2s)-2-amino-5-(6-aminopyridin-3-yl)-1-(4-ethylpiperidin-1-yl)pentan-1-one;hydrochloride Chemical compound Cl.C1CC(CC)CCN1C(=O)[C@@H](N)CCCC1=CC=C(N)N=C1 UOYFNFYECDTFDW-RSAXXLAASA-N 0.000 description 3
MYEZXKRWBSSQQD-UHFFFAOYSA-N 3-benzylsulfanyl-5-phenylpyridin-4-amine Chemical compound C1=NC=C(C=2C=CC=CC=2)C(N)=C1SCC1=CC=CC=C1 MYEZXKRWBSSQQD-UHFFFAOYSA-N 0.000 description 3
WVIJOUFQYFUXAY-UHFFFAOYSA-N 4-(difluoromethylidene)piperidine Chemical compound FC(F)=C1CCNCC1 WVIJOUFQYFUXAY-UHFFFAOYSA-N 0.000 description 3
KRRTXVSBTPCDOS-UHFFFAOYSA-N 5-bromopyrazin-2-amine Chemical compound NC1=CN=C(Br)C=N1 KRRTXVSBTPCDOS-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000012317 TBTU Substances 0.000 description 3
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 3
IRUFBBLUWKRMGC-QFIPXVFZSA-N benzyl (2s)-4-(5-nitropyridin-2-yl)-2-(phenylmethoxycarbonylamino)butanoate Chemical compound N1=CC([N+](=O)[O-])=CC=C1CC[C@@H](C(=O)OCC=1C=CC=CC=1)NC(=O)OCC1=CC=CC=C1 IRUFBBLUWKRMGC-QFIPXVFZSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 3
QPMUXIIQQHTMKO-QMMMGPOBSA-N methyl (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-ynoate Chemical compound COC(=O)[C@H](CC#C)NC(=O)OC(C)(C)C QPMUXIIQQHTMKO-QMMMGPOBSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 3
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
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HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000035602 clotting Effects 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000006260 foam Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
KMFITZSAVKVTTB-ZDUSSCGKSA-N methyl (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-pyridin-4-ylpent-4-ynoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CC#CC1=CC=NC=C1 KMFITZSAVKVTTB-ZDUSSCGKSA-N 0.000 description 1
APQOKEHIELYRFL-NSHDSACASA-N methyl (2s)-5-(5-aminopyrazin-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-ynoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CC#CC1=CN=C(N)C=N1 APQOKEHIELYRFL-NSHDSACASA-N 0.000 description 1
HEGKXOOTBUFTQR-NSHDSACASA-N methyl (2s)-5-(5-aminopyrazin-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CCCC1=CN=C(N)C=N1 HEGKXOOTBUFTQR-NSHDSACASA-N 0.000 description 1
OEZMHXSRTBWUBK-ZDUSSCGKSA-N methyl (2s)-5-(5-aminopyridin-2-yl)-2-(2,2-dimethylpropanoyloxyamino)pent-4-ynoate Chemical compound CC(C)(C)C(=O)ON[C@H](C(=O)OC)CC#CC1=CC=C(N)C=N1 OEZMHXSRTBWUBK-ZDUSSCGKSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
UGNAFWDQFZLMAO-QKXMYKPYSA-N n-[2-[[(2s)-1-(4-ethylpiperidin-3-yl)-1-oxo-5-piperidin-3-ylpentan-2-yl]sulfamoyl]-6-thiophen-2-ylphenyl]propanamide;hydrochloride Chemical compound Cl.CCC1CCNCC1C(=O)[C@@H](NS(=O)(=O)C=1C(=C(C=2SC=CC=2)C=CC=1)NC(=O)CC)CCCC1CNCCC1 UGNAFWDQFZLMAO-QKXMYKPYSA-N 0.000 description 1
OKLDJMFDMNRAKK-QFIPXVFZSA-N n-[2-[[(2s)-5-(2-aminopyridin-3-yl)-1-oxo-1-[4-(trifluoromethyl)-3,6-dihydro-2h-pyridin-1-yl]pentan-2-yl]sulfamoyl]-6-thiophen-2-ylphenyl]propanamide Chemical compound C([C@H](NS(=O)(=O)C1=CC=CC(=C1NC(=O)CC)C=1SC=CC=1)C(=O)N1CC=C(CC1)C(F)(F)F)CCC1=CC=CN=C1N OKLDJMFDMNRAKK-QFIPXVFZSA-N 0.000 description 1
XXDPTWMPMQAACN-SANMLTNESA-N n-[2-[[(2s)-5-(6-amino-4-ethylpyridin-3-yl)-1-[4-(difluoromethylidene)piperidin-1-yl]-1-oxopentan-2-yl]sulfamoyl]-6-cyclopentylphenyl]acetamide Chemical compound CCC1=CC(N)=NC=C1CCC[C@@H](C(=O)N1CCC(CC1)=C(F)F)NS(=O)(=O)C1=CC=CC(C2CCCC2)=C1NC(C)=O XXDPTWMPMQAACN-SANMLTNESA-N 0.000 description 1
ZEDZNWSUWNMVRC-UQIIZPHYSA-N n-[3-[[(2s)-5-(6-aminopyridin-3-yl)-1-(4-methylpiperidin-1-yl)-1-oxopentan-2-yl]sulfamoyl]-5-phenylpyridin-4-yl]propanamide;hydrochloride Chemical compound Cl.C([C@H](NS(=O)(=O)C1=CN=CC(=C1NC(=O)CC)C=1C=CC=CC=1)C(=O)N1CCC(C)CC1)CCC1=CC=C(N)N=C1 ZEDZNWSUWNMVRC-UQIIZPHYSA-N 0.000 description 1
230000014508 negative regulation of coagulation Effects 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical class OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
229940071182 stannate Drugs 0.000 description 1
125000005402 stannate group Chemical group 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical compound S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
CBWXHXSPGJQJCO-SFHVURJKSA-N tert-butyl N-[(2S)-5-(5-aminopyridin-2-yl)-1-(4-methylpiperidin-1-yl)-1-oxopentan-2-yl]carbamate Chemical compound C1CC(C)CCN1C(=O)[C@@H](NC(=O)OC(C)(C)C)CCCC1=CC=C(N)C=N1 CBWXHXSPGJQJCO-SFHVURJKSA-N 0.000 description 1
FSKKVXFHYATPAG-UHFFFAOYSA-N tert-butyl n-(3,5-dibromopyridin-4-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=C(Br)C=NC=C1Br FSKKVXFHYATPAG-UHFFFAOYSA-N 0.000 description 1
DRZYCRFOGWMEES-UHFFFAOYSA-N tert-butyl n-pyridin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=NC=C1 DRZYCRFOGWMEES-UHFFFAOYSA-N 0.000 description 1
229960003766 thrombin (human) Drugs 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229940038773 trisodium citrate Drugs 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000002676 xenobiotic agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- 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
- 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
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Hydrogenated Pyridines (AREA)

SK1351-2002A 2000-03-23 2001-03-22 Sulfónamidy, spôsob ich výroby, medziprodukty, liečivo a farmaceutická kompozícia s ich obsahom SK286687B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0003724A FR2806722B1 (fr)	2000-03-23	2000-03-23	Derives de n-(heterocyclylbutyl) benzene-ou pyridine sulfonamide, leur preparation et leur application en therapeutique
PCT/FR2001/000861 WO2001070736A1 (fr)	2000-03-23	2001-03-22	N-(heterocyclyl)benzene-ou pyridine sulfonamides comme agents antithrombotiques et anticoagulantes

Publications (2)

Publication Number	Publication Date
SK13512002A3 SK13512002A3 (sk)	2003-03-04
SK286687B6 true SK286687B6 (sk)	2009-03-05

Family

ID=8848428

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1351-2002A SK286687B6 (sk)	2000-03-23	2001-03-22	Sulfónamidy, spôsob ich výroby, medziprodukty, liečivo a farmaceutická kompozícia s ich obsahom

Country Status (35)

Country	Link
US (1)	US6680329B2 (bg)
EP (1)	EP1268469B1 (bg)
JP (1)	JP2003528098A (bg)
KR (1)	KR100791693B1 (bg)
CN (1)	CN1183128C (bg)
AR (1)	AR029900A1 (bg)
AT (1)	ATE269325T1 (bg)
AU (2)	AU4661701A (bg)
BG (1)	BG65863B1 (bg)
BR (1)	BR0109385A (bg)
CA (1)	CA2401637C (bg)
DE (1)	DE60103868T2 (bg)
DK (1)	DK1268469T3 (bg)
EA (1)	EA004986B1 (bg)
EE (1)	EE05084B1 (bg)
ES (1)	ES2222358T3 (bg)
FR (1)	FR2806722B1 (bg)
HK (1)	HK1051537A1 (bg)
HR (1)	HRP20020762B1 (bg)
HU (1)	HUP0300695A2 (bg)
IL (2)	IL151619A0 (bg)
IS (1)	IS2304B (bg)
ME (1)	MEP17408A (bg)
MX (1)	MXPA02009276A (bg)
NO (1)	NO324835B1 (bg)
PL (1)	PL204660B1 (bg)
PT (1)	PT1268469E (bg)
RS (1)	RS50370B (bg)
SI (1)	SI1268469T1 (bg)
SK (1)	SK286687B6 (bg)
TR (1)	TR200402343T4 (bg)
TW (1)	TWI290141B (bg)
UA (1)	UA71667C2 (bg)
WO (1)	WO2001070736A1 (bg)
ZA (1)	ZA200206996B (bg)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8729107B2 (en) *	2002-12-06	2014-05-20	Purdue Research Foundation	Pyridines for treating injured mammalian nerve tissue
CA2508165C (en) *	2002-12-06	2014-05-06	Purdue Research Foundation	Pyridines for treating injured mammalian nerve tissue
EP1739077A4 (en) *	2004-04-19	2008-04-16	Daiso Co Ltd	PROCESS FOR THE PRODUCTION OF NON-NATURAL AMINO ACIDS AND INTERMEDIATES THEREFOR
US7750162B2 (en)	2004-04-19	2010-07-06	Daiso Co., Ltd.	Process for preparation of nonnatural amino acid and intermediate thereof
GB0507577D0 (en)	2005-04-14	2005-05-18	Novartis Ag	Organic compounds
EP2276731A1 (en) *	2008-04-09	2011-01-26	Boehringer Ingelheim International GmbH	2-sulfonylamino-4-heteroaryl butyramide antagonists of ccr10
CA2725140A1 (en) *	2008-05-22	2009-11-26	Boehringer Ingelheim International Gmbh	Alpha-substituted n-sulfonyl gylcine amides antagonists of ccr10, compositions containing the same and methods for using them
MX345259B (es) *	2010-01-28	2017-01-23	The Medicines Company (Leipzig) Gmbh	Inhibidores de serina proteasas similares a tripsina, y su preparación y uso.
FR2981071B1 (fr) *	2011-10-10	2014-02-07	Centre Nat Rech Scient	Synthese versatile et stereospecifique d'acides amines gamma,delta-insatures par la reaction de wittig

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2727410B1 (fr) *	1994-11-25	1996-12-20	Synthelabo	Chlorures de sulfonyles, leur preparation et leur utilisation comme intermediaires de synthese
FR2728570B1 (fr) *	1994-12-23	1997-04-11	Synthelabo	Derives de 1-oxo-2-(phenylsulfonylamino)pentylpiperidine, leur preparation et leur application en therapeutique
FR2756285B1 (fr) *	1996-11-22	1998-12-18	Synthelabo	Derives de n-(imidazolylbutyle)benzenesulfonamide, leur preparation et leur application en therapeutique
FR2756220B1 (fr) *	1996-11-27	1998-12-24	Lorraine Laminage	Roue pour vehicule terrestre a moteur
FR2771094B1 (fr) *	1997-11-19	2000-02-04	Synthelabo	Derives de piperidine-2-carboxylate, leur preparation et leur application en therapeutique

2000
- 2000-03-23 FR FR0003724A patent/FR2806722B1/fr not_active Expired - Fee Related
2001
- 2001-03-22 EP EP01919537A patent/EP1268469B1/fr not_active Expired - Lifetime
- 2001-03-22 CN CNB018084974A patent/CN1183128C/zh not_active Expired - Fee Related
- 2001-03-22 AT AT01919537T patent/ATE269325T1/de active
- 2001-03-22 AU AU4661701A patent/AU4661701A/xx active Pending
- 2001-03-22 EE EEP200200540A patent/EE05084B1/xx not_active IP Right Cessation
- 2001-03-22 RS YUP-670/02A patent/RS50370B/sr unknown
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- 2001-03-22 CA CA002401637A patent/CA2401637C/en not_active Expired - Fee Related
- 2001-03-22 TW TW090106733A patent/TWI290141B/zh active
- 2001-03-22 JP JP2001568937A patent/JP2003528098A/ja not_active Ceased
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- 2001-03-22 WO PCT/FR2001/000861 patent/WO2001070736A1/fr active IP Right Grant
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- 2001-03-22 DK DK01919537T patent/DK1268469T3/da active
- 2001-03-22 HU HU0300695A patent/HUP0300695A2/hu unknown
2002
- 2002-08-30 ZA ZA200206996A patent/ZA200206996B/en unknown
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Also Published As

Publication number	Publication date
FR2806722B1 (fr)	2002-05-17
AR029900A1 (es)	2003-07-23
JP2003528098A (ja)	2003-09-24
PL204660B1 (pl)	2010-01-29
CN1426407A (zh)	2003-06-25
EE200200540A (et)	2004-04-15
BG65863B1 (bg)	2010-03-31
IS2304B (is)	2007-10-15
SK13512002A3 (sk)	2003-03-04
YU67002A (sh)	2005-07-19
DK1268469T3 (da)	2004-10-11
EP1268469B1 (fr)	2004-06-16
US6680329B2 (en)	2004-01-20
DE60103868D1 (de)	2004-07-22
DE60103868T2 (de)	2005-06-09
MXPA02009276A (es)	2003-05-23
FR2806722A1 (fr)	2001-09-28
EA200200838A1 (ru)	2003-04-24
EE05084B1 (et)	2008-10-15
ATE269325T1 (de)	2004-07-15
AU4661701A (en)	2001-10-03
CN1183128C (zh)	2005-01-05
CA2401637C (en)	2009-11-10
ES2222358T3 (es)	2005-02-01
EP1268469A1 (fr)	2003-01-02
SI1268469T1 (en)	2004-10-31
NO20024496D0 (no)	2002-09-19
TWI290141B (en)	2007-11-21
KR20020081476A (ko)	2002-10-26
BG107130A (bg)	2003-06-30
CA2401637A1 (en)	2001-09-27
MEP17408A (en)	2010-06-10
BR0109385A (pt)	2003-06-03
HRP20020762B1 (en)	2005-02-28
RS50370B (sr)	2009-11-10
HK1051537A1 (en)	2003-08-08
IL151619A (en)	2009-05-04
WO2001070736A1 (fr)	2001-09-27
AU2001246617B2 (en)	2006-03-02
PL364988A1 (en)	2004-12-27
IS6535A (is)	2002-08-30
TR200402343T4 (tr)	2004-12-21
NO20024496L (no)	2002-11-22
US20030207920A1 (en)	2003-11-06
EA004986B1 (ru)	2004-10-28
HRP20020762A2 (en)	2003-12-31
NO324835B1 (no)	2007-12-17
ZA200206996B (en)	2003-09-01
HUP0300695A2 (hu)	2003-07-28
KR100791693B1 (ko)	2008-01-03
PT1268469E (pt)	2004-10-29
IL151619A0 (en)	2003-04-10
UA71667C2 (uk)	2004-12-15

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2012-12-03	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20120322