SK12442002A3 - Farmaceutické kompozície obsahujúce deriváty 3-aminoazetidínu, tieto deriváty a ich príprava - Google Patents

Farmaceutické kompozície obsahujúce deriváty 3-aminoazetidínu, tieto deriváty a ich príprava Download PDF

Info

Publication number: SK12442002A3
Authority: SK; Slovakia
Prior art keywords: group; alkyl; alk; alkoxy; substituted
Prior art date: 2000-03-03

Application number

SK1244-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Daniel Achard

Herv Bouchard

Jean Bouquerel

Bruno Filoche

Serge Grisoni

Augustin Hittinger

Michael Myers

Original Assignee

Aventis Pharma S. A.

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.)

2000-03-03

Filing date

2001-03-01

Publication date

2003-02-04

2001-03-01 Application filed by Aventis Pharma S. A. filed Critical Aventis Pharma S. A.

2003-02-04 Publication of SK12442002A3 publication Critical patent/SK12442002A3/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
FDPKMJDUXJFKOI-UHFFFAOYSA-N azetidin-3-amine Chemical class NC1CNC1 FDPKMJDUXJFKOI-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 60
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 56
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 37
239000004480 active ingredient Substances 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims description 132
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
125000001424 substituent group Chemical group 0.000 claims description 72
229910052757 nitrogen Inorganic materials 0.000 claims description 71
125000003545 alkoxy group Chemical group 0.000 claims description 65
125000000623 heterocyclic group Chemical group 0.000 claims description 60
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 59
238000000034 method Methods 0.000 claims description 56
229910052736 halogen Inorganic materials 0.000 claims description 51
-1 -CO-alk Chemical group 0.000 claims description 47
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
125000005843 halogen group Chemical group 0.000 claims description 42
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 38
229920006395 saturated elastomer Polymers 0.000 claims description 37
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 36
125000002619 bicyclic group Chemical group 0.000 claims description 36
125000005842 heteroatom Chemical group 0.000 claims description 36
125000002950 monocyclic group Chemical group 0.000 claims description 36
229910052717 sulfur Inorganic materials 0.000 claims description 36
229910052760 oxygen Inorganic materials 0.000 claims description 35
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
125000004043 oxo group Chemical group O=* 0.000 claims description 33
239000001301 oxygen Substances 0.000 claims description 33
239000011593 sulfur Chemical group 0.000 claims description 33
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 18
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 18
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 18
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 18
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
229920002554 vinyl polymer Polymers 0.000 claims description 17
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 10
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 9
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 9
125000000815 N-oxide group Chemical group 0.000 claims description 9
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 9
125000003884 phenylalkyl group Chemical group 0.000 claims description 9
125000000335 thiazolyl group Chemical group 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
229930192474 thiophene Natural products 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 6
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
230000003287 optical effect Effects 0.000 claims description 6
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 6
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims description 5
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000005493 quinolyl group Chemical group 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
150000003852 triazoles Chemical class 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
125000005956 isoquinolyl group Chemical group 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
239000000203 mixture Substances 0.000 description 41
239000000243 solution Substances 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 22
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
239000004922 lacquer Substances 0.000 description 15
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 description 14
KZBHZRNNTACIDG-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]azetidin-3-amine Chemical compound C1C(N)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 KZBHZRNNTACIDG-UHFFFAOYSA-N 0.000 description 13
239000000843 powder Substances 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
238000009835 boiling Methods 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
239000003814 drug Substances 0.000 description 10
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 9
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 9
238000003818 flash chromatography Methods 0.000 description 9
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000012153 distilled water Substances 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000006071 cream Substances 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
FWVOLXNAXIIUAJ-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]azetidine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CCC1 FWVOLXNAXIIUAJ-UHFFFAOYSA-N 0.000 description 4
IIQKIICAOXAXEJ-UHFFFAOYSA-N 3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=CC(S(Cl)(=O)=O)=C1 IIQKIICAOXAXEJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
GFZSTPUFGXDDNJ-UHFFFAOYSA-N n-(1-benzhydrylazetidin-3-yl)-3,5-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC2CN(C2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GFZSTPUFGXDDNJ-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
SFXIMUPKAOTJSI-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]azetidin-3-ol Chemical compound C1C(O)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 SFXIMUPKAOTJSI-UHFFFAOYSA-N 0.000 description 3
IEYPLPQQZFREGI-UHFFFAOYSA-N 3-[bromo-(4-chlorophenyl)methyl]pyridine Chemical compound C1=CC(Cl)=CC=C1C(Br)C1=CC=CN=C1 IEYPLPQQZFREGI-UHFFFAOYSA-N 0.000 description 3
208000024827 Alzheimer disease Diseases 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
206010049771 Shock haemorrhagic Diseases 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
230000003533 narcotic effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000002265 prevention Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
230000009466 transformation Effects 0.000 description 3
238000000844 transformation Methods 0.000 description 3
125000005270 trialkylamine group Chemical group 0.000 description 3
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Classifications

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SK1244-2002A 2000-03-03 2001-03-01 Farmaceutické kompozície obsahujúce deriváty 3-aminoazetidínu, tieto deriváty a ich príprava SK12442002A3 (sk)

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FR0002777A FR2805810B1 (fr)	2000-03-03	2000-03-03	Compositions pharmaceutiques contenant des derives de 3- amino-azetidine, les nouveaux derives et leur preparation
PCT/FR2001/000601 WO2001064633A1 (fr)	2000-03-03	2001-03-01	Compositions pharmaceutiques contenant des derives de 3-amino-azetidine, les nouveaux derives et leur preparation

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FR2649100B1 (fr) *	1989-06-29	1994-03-04	Laboratorios Dr Esteve Sa	Nouvelles azetidines, leur preparation et leur application comme intermediaires pour la preparation de composes avec activite antimicrobienne
JPH05201971A (ja) *	1992-01-28	1993-08-10	Hokuriku Seiyaku Co Ltd	環状アミン含有ベンゼンスルホンアミド誘導体
WO1997001556A1 (en) *	1995-06-29	1997-01-16	Novo Nordisk A/S	Novel substituted azacyclic or azabicyclic compounds
GB9714129D0 (en) *	1997-07-04	1997-09-10	Pfizer Ltd	Azetidines

2000
- 2000-03-03 FR FR0002777A patent/FR2805810B1/fr not_active Expired - Fee Related
2001
- 2001-01-03 UA UA2002097700A patent/UA72319C2/uk unknown
- 2001-02-23 TW TW090104188A patent/TWI294420B/zh not_active IP Right Cessation
- 2001-03-01 IL IL15120901A patent/IL151209A0/xx unknown
- 2001-03-01 DK DK01909938.1T patent/DK1263721T3/da active
- 2001-03-01 CN CNB018060269A patent/CN1187325C/zh not_active Expired - Fee Related
- 2001-03-01 BR BR0108894-7A patent/BR0108894A/pt not_active Application Discontinuation
- 2001-03-01 SK SK1244-2002A patent/SK12442002A3/sk unknown
- 2001-03-01 EP EP01909938A patent/EP1263721B1/fr not_active Expired - Lifetime
- 2001-03-01 PT PT01909938T patent/PT1263721E/pt unknown
- 2001-03-01 OA OA1200200269A patent/OA12221A/fr unknown
- 2001-03-01 AU AU2001237526A patent/AU2001237526B2/en not_active Ceased
- 2001-03-01 SI SI200130980T patent/SI1263721T1/sl unknown
- 2001-03-01 PL PL01365007A patent/PL365007A1/pl not_active IP Right Cessation
- 2001-03-01 JP JP2001563476A patent/JP2003525269A/ja not_active Ceased
- 2001-03-01 DE DE60142890T patent/DE60142890D1/de not_active Expired - Lifetime
- 2001-03-01 NZ NZ521076A patent/NZ521076A/en unknown
- 2001-03-01 HR HR20020710A patent/HRP20020710A2/hr not_active Application Discontinuation
- 2001-03-01 AU AU3752601A patent/AU3752601A/xx active Pending
- 2001-03-01 ES ES01909938T patent/ES2351183T3/es not_active Expired - Lifetime
- 2001-03-01 KR KR1020027011516A patent/KR100813740B1/ko not_active Expired - Fee Related
- 2001-03-01 MX MXPA02008346A patent/MXPA02008346A/es active IP Right Grant
- 2001-03-01 HU HU0300350A patent/HUP0300350A2/hu unknown
- 2001-03-01 EE EEP200200486A patent/EE05081B1/xx not_active IP Right Cessation
- 2001-03-01 WO PCT/FR2001/000601 patent/WO2001064633A1/fr not_active Ceased
- 2001-03-01 CA CA002400138A patent/CA2400138A1/fr not_active Abandoned
- 2001-03-01 EA EA200200942A patent/EA004649B1/ru not_active IP Right Cessation
- 2001-03-01 AT AT01909938T patent/ATE478840T1/de active
- 2001-03-01 YU YU65902A patent/YU65902A/sh unknown
- 2001-03-02 AR ARP010101025A patent/AR034405A1/es unknown
- 2001-09-07 DZ DZ013311A patent/DZ3311A1/fr active
2002
- 2002-08-12 IL IL151209A patent/IL151209A/en not_active IP Right Cessation
- 2002-08-28 ZA ZA200206916A patent/ZA200206916B/en unknown
- 2002-08-28 MA MA26793A patent/MA26879A1/fr unknown
- 2002-09-02 NO NO20024176A patent/NO324523B1/no not_active IP Right Cessation
- 2002-09-03 BG BG107057A patent/BG107057A/bg unknown
2010
- 2010-10-29 CY CY20101100983T patent/CY1111075T1/el unknown

Also Published As

Publication number	Publication date
PT1263721E (pt)	2010-10-28
FR2805810A1 (fr)	2001-09-07
MXPA02008346A (es)	2002-12-13
CY1111075T1 (el)	2015-06-11
EE200200486A (et)	2004-02-16
DK1263721T3 (da)	2011-01-03
BG107057A (bg)	2003-07-31
JP2003525269A (ja)	2003-08-26
NZ521076A (en)	2004-08-27
YU65902A (sh)	2005-09-19
UA72319C2 (en)	2005-02-15
KR100813740B1 (ko)	2008-03-13
NO20024176D0 (no)	2002-09-02
CN1187325C (zh)	2005-02-02
AU2001237526B2 (en)	2006-01-05
DZ3311A1 (fr)	2001-09-07
EP1263721A1 (fr)	2002-12-11
ZA200206916B (en)	2003-07-17
NO324523B1 (no)	2007-11-12
EE05081B1 (et)	2008-10-15
EP1263721B1 (fr)	2010-08-25
NO20024176L (no)	2002-10-29
ES2351183T3 (es)	2011-02-01
BR0108894A (pt)	2003-04-29
DE60142890D1 (de)	2010-10-07
EA004649B1 (ru)	2004-06-24
HRP20020710A2 (en)	2005-06-30
IL151209A0 (en)	2003-04-10
TWI294420B (en)	2008-03-11
SI1263721T1 (sl)	2011-01-31
KR20030013375A (ko)	2003-02-14
HUP0300350A2 (hu)	2003-06-28
CN1411440A (zh)	2003-04-16
AR034405A1 (es)	2004-02-25
FR2805810B1 (fr)	2002-04-26
AU3752601A (en)	2001-09-12
EA200200942A1 (ru)	2003-02-27
IL151209A (en)	2010-05-17
PL365007A1 (pl)	2004-12-27
ATE478840T1 (de)	2010-09-15
MA26879A1 (fr)	2004-12-20
CA2400138A1 (fr)	2001-09-07
WO2001064633A1 (fr)	2001-09-07
OA12221A (fr)	2006-05-10

Legal Events

Date	Code	Title	Description
2010-11-08	FB9A	Suspension of patent application procedure

Publication	Publication Date	Title
SK12442002A3 (sk)	2003-02-04	Farmaceutické kompozície obsahujúce deriváty 3-aminoazetidínu, tieto deriváty a ich príprava
US6566356B2 (en)	2003-05-20	Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation
US6355631B1 (en)	2002-03-12	Pharmaceutical compositions containing azetidine derivatives, novel azetidine derivatives and their preparation
KR100819572B1 (ko)	2008-04-04	아제티딘 유도체를 함유하는 약학 조성물, 신규한아제티딘 유도체 및 이들의 제조방법
KR20020075935A (ko)	2002-10-07	아제티딘 유도체, 이의 제조방법 및 이를 함유하는 약학조성물