MXPA01000945A - Compuestos nuevos de piperidin-4-sulfonamida, un proceso para su preparacion y composiciones farmaceuticas que los contienen. - Google Patents
Compuestos nuevos de piperidin-4-sulfonamida, un proceso para su preparacion y composiciones farmaceuticas que los contienen.Info
- Publication number
- MXPA01000945A MXPA01000945A MXPA01000945A MXPA01000945A MXPA01000945A MX PA01000945 A MXPA01000945 A MX PA01000945A MX PA01000945 A MXPA01000945 A MX PA01000945A MX PA01000945 A MXPA01000945 A MX PA01000945A MX PA01000945 A MXPA01000945 A MX PA01000945A
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- compounds
- group
- carbon atoms
- linear
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 164
- 238000000034 method Methods 0.000 title claims description 126
- 230000008569 process Effects 0.000 title claims description 115
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 262
- -1 cyano, nitro, amino Chemical group 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 206010048554 Endothelial dysfunction Diseases 0.000 claims abstract description 15
- 230000008694 endothelial dysfunction Effects 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 150000004677 hydrates Chemical class 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 230000001575 pathological effect Effects 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 37
- 230000002829 reductive effect Effects 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 230000002792 vascular Effects 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 206010034576 Peripheral ischaemia Diseases 0.000 claims description 4
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
- 230000000747 cardiac effect Effects 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000007796 conventional method Methods 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 4
- 230000002107 myocardial effect Effects 0.000 claims description 4
- 208000031225 myocardial ischemia Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 230000003143 atherosclerotic effect Effects 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000003902 lesion Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 2
- IJPQYBRPCAKAOE-UHFFFAOYSA-N 5-methyl-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound CC1=C(C=2C(=NON=2)C=C1)S(=O)(=O)N IJPQYBRPCAKAOE-UHFFFAOYSA-N 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- ZNCQTGJPCLMLRL-UHFFFAOYSA-N n-[1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-yl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(NC3CCN(CCC=4C5=CC=CC=C5OC=4)CC3)=O)=CC=CC2=C1 ZNCQTGJPCLMLRL-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229940126601 medicinal product Drugs 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 236
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 125
- 238000002844 melting Methods 0.000 description 105
- 230000008018 melting Effects 0.000 description 105
- 239000000243 solution Substances 0.000 description 85
- 239000000758 substrate Substances 0.000 description 75
- 238000004452 microanalysis Methods 0.000 description 70
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 58
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 239000011541 reaction mixture Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000003153 chemical reaction reagent Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 238000004587 chromatography analysis Methods 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- WHIDHHUCCTYJKA-UHFFFAOYSA-N isoquinoline-5-sulfonyl chloride Chemical compound N1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 WHIDHHUCCTYJKA-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 8
- 229960004373 acetylcholine Drugs 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000003511 endothelial effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- AVRJTNMCEZERCF-UHFFFAOYSA-N 1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CCC1=COC2=CC=CC=C12 AVRJTNMCEZERCF-UHFFFAOYSA-N 0.000 description 3
- ICDKAYJHRKZCJI-UHFFFAOYSA-N 3-(2-bromoethyl)-5-fluoro-1-benzofuran Chemical compound FC1=CC=C2OC=C(CCBr)C2=C1 ICDKAYJHRKZCJI-UHFFFAOYSA-N 0.000 description 3
- QDWTXRWOKORYQH-UHFFFAOYSA-N 3-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Br)=C1 QDWTXRWOKORYQH-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 3
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 description 2
- JOCHPWBPQAYQRP-UHFFFAOYSA-N 1-(4-aminopiperidin-1-yl)-3-(1-benzofuran-3-yl)propan-2-ol Chemical compound C1CC(N)CCN1CC(O)CC1=COC2=CC=CC=C12 JOCHPWBPQAYQRP-UHFFFAOYSA-N 0.000 description 2
- IUCXDOCSJMXEOM-UHFFFAOYSA-N 1-[1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-yl]isoquinoline-5-sulfonamide Chemical compound O1C=C(C2=C1C=CC=C2)CCN1CCC(CC1)C1=NC=CC=2C(=CC=CC1=2)S(=O)(=O)N IUCXDOCSJMXEOM-UHFFFAOYSA-N 0.000 description 2
- KZXXXLQIEMTQCZ-UHFFFAOYSA-N 1-[1-[2-(6-methoxy-1-benzofuran-3-yl)ethyl]piperidin-4-yl]isoquinoline-5-sulfonamide Chemical compound COC1=CC2=C(C(=CO2)CCN2CCC(CC2)C2=NC=CC=3C(=CC=CC2=3)S(=O)(=O)N)C=C1 KZXXXLQIEMTQCZ-UHFFFAOYSA-N 0.000 description 2
- GWPTXNUDBQIEBP-UHFFFAOYSA-N 1-[2-(1-benzofuran-3-yl)ethyl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1CCC1=COC2=CC=CC=C12 GWPTXNUDBQIEBP-UHFFFAOYSA-N 0.000 description 2
- NWERFMHAOKXNKY-UHFFFAOYSA-N 1-[3-(1-benzofuran-2-yl)propyl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1CCCC1=CC2=CC=CC=C2O1 NWERFMHAOKXNKY-UHFFFAOYSA-N 0.000 description 2
- SIYWVPMYOGMRDW-UHFFFAOYSA-N 2,1,3-benzoxadiazole-4-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC2=NON=C12 SIYWVPMYOGMRDW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- IYGHOECMOXJEJB-UHFFFAOYSA-N 3-(2-bromoethyl)-5-methoxy-1-benzofuran Chemical compound COC1=CC=C2OC=C(CCBr)C2=C1 IYGHOECMOXJEJB-UHFFFAOYSA-N 0.000 description 2
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- 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
-
- 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
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0001171A FR2804429B1 (fr) | 2000-01-31 | 2000-01-31 | Nouveaux derives de 4-sulfonamides piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA01000945A true MXPA01000945A (es) | 2002-06-04 |
Family
ID=8846469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA01000945A MXPA01000945A (es) | 2000-01-31 | 2001-01-26 | Compuestos nuevos de piperidin-4-sulfonamida, un proceso para su preparacion y composiciones farmaceuticas que los contienen. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6323217B2 (enExample) |
| EP (1) | EP1122254B1 (enExample) |
| JP (1) | JP3513493B2 (enExample) |
| KR (1) | KR100463369B1 (enExample) |
| CN (1) | CN1298705C (enExample) |
| AR (1) | AR027335A1 (enExample) |
| AT (1) | ATE294175T1 (enExample) |
| AU (1) | AU774808B2 (enExample) |
| BR (1) | BR0100234A (enExample) |
| CA (1) | CA2332513C (enExample) |
| DE (1) | DE60110278T2 (enExample) |
| DK (1) | DK1122254T3 (enExample) |
| EA (1) | EA003096B1 (enExample) |
| ES (1) | ES2241757T3 (enExample) |
| FR (1) | FR2804429B1 (enExample) |
| HK (1) | HK1039117B (enExample) |
| HU (1) | HUP0100489A3 (enExample) |
| MX (1) | MXPA01000945A (enExample) |
| NO (1) | NO320387B1 (enExample) |
| NZ (1) | NZ509636A (enExample) |
| PL (1) | PL345528A1 (enExample) |
| PT (1) | PT1122254E (enExample) |
| SI (1) | SI1122254T1 (enExample) |
| ZA (1) | ZA200100864B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ521978A (en) * | 2000-04-28 | 2004-10-29 | Acadia Pharm Inc | Compounds that affect cholinergic receptors and are particularly muscarinic agonists |
| EP1535912A1 (en) * | 2000-04-28 | 2005-06-01 | Arcadia Pharmaceuticals Inc. | Muscarinic agonists |
| AR040336A1 (es) * | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de piperidina, uso del mismo para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para preparar dicho compuesto |
| AU2003284402A1 (en) * | 2002-11-15 | 2004-06-15 | Yamanouchi Pharmaceutical Co., Ltd. | Antagonist to melanin-concentrating hormone receptor |
| JP2008507492A (ja) * | 2004-07-23 | 2008-03-13 | バイエル・クロツプサイエンス・エス・アー | 殺菌剤としてのｎ−［２−（４−ピリジニル）エチル］ベンズアミド誘導体 |
| ATE527258T1 (de) * | 2004-07-28 | 2011-10-15 | Takeda Pharmaceutical | Pyrroloä2,3-cüpyridinverbindung, verfahren zu deren herstellung und anwendung |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| ES2362617T3 (es) * | 2005-02-25 | 2011-07-08 | Kowa Company, Ltd. | Proceso para la producción de haluro de 4-fluoroisoquinolin-5-sulfonilo o una de sus sales. |
| WO2007110449A1 (en) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| TW200812963A (en) | 2006-04-13 | 2008-03-16 | Euro Celtique Sa | Benzenesulfonamide compounds and the use thereof |
| US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| CL2007003223A1 (es) * | 2006-11-10 | 2008-01-11 | Wyeth Corp | Compuestos derivados de piperidinil 4-arilsulfonamidas n-sustituidas, que actuan como moduladores de la proteina sfrp-1; proceso para preparar los compuestos; co mposicion farmaceutica que comprende a dichos copmpuestos y uso de los compuestos para preparar medicamentos para el tratamiento de enfermedades. |
| WO2008124118A1 (en) * | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| AR080375A1 (es) | 2010-03-05 | 2012-04-04 | Sanofi Aventis | Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 7-sulfonamida |
| PL395470A1 (pl) | 2011-06-29 | 2013-01-07 | Adamed Spólka Z Ograniczona Odpowiedzialnoscia | Sulfonamidowe pochodne amin alicyklicznych do leczenia chorób osrodkowego ukladu nerwowego |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956382A (en) * | 1987-02-07 | 1990-09-11 | Pfizer Inc. | Sulfonamide anti-arrhythmic agents |
| US4857301A (en) * | 1987-09-25 | 1989-08-15 | Schering Corporation | Sulfonamide compounds, compositions and method of use |
| FR2679906B1 (fr) * | 1991-07-31 | 1995-01-20 | Adir | Nouvelles (isoquinolein-5 yl) sulfonamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DK148392D0 (da) * | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
| AU6971794A (en) * | 1993-05-26 | 1994-12-20 | Smithkline Beecham Laboratoires Pharmaceutiques | Novel compounds |
| FR2716679B1 (fr) * | 1994-02-25 | 1996-04-05 | Adir | Nouvelles sulfonamides substituées, leur procédé de préparation et les compositions pharmaceutiques les renfermant. |
| HN1997000027A (es) * | 1996-12-06 | 1997-06-05 | Pfizer Prod Inc | Derivados de 6-fenil piridil - 2 amina |
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2000
- 2000-01-31 FR FR0001171A patent/FR2804429B1/fr not_active Expired - Fee Related
-
2001
- 2001-01-23 CN CNB011123346A patent/CN1298705C/zh not_active Expired - Fee Related
- 2001-01-26 MX MXPA01000945A patent/MXPA01000945A/es unknown
- 2001-01-30 US US09/772,569 patent/US6323217B2/en not_active Expired - Fee Related
- 2001-01-30 EP EP01400225A patent/EP1122254B1/fr not_active Expired - Lifetime
- 2001-01-30 NO NO20010522A patent/NO320387B1/no unknown
- 2001-01-30 CA CA002332513A patent/CA2332513C/fr not_active Expired - Fee Related
- 2001-01-30 HU HU0100489A patent/HUP0100489A3/hu unknown
- 2001-01-30 ES ES01400225T patent/ES2241757T3/es not_active Expired - Lifetime
- 2001-01-30 DK DK01400225T patent/DK1122254T3/da active
- 2001-01-30 NZ NZ509636A patent/NZ509636A/en unknown
- 2001-01-30 EA EA200100090A patent/EA003096B1/ru unknown
- 2001-01-30 AT AT01400225T patent/ATE294175T1/de not_active IP Right Cessation
- 2001-01-30 PT PT01400225T patent/PT1122254E/pt unknown
- 2001-01-30 SI SI200130342T patent/SI1122254T1/xx unknown
- 2001-01-30 DE DE60110278T patent/DE60110278T2/de not_active Expired - Fee Related
- 2001-01-31 AR ARP010100429A patent/AR027335A1/es not_active Application Discontinuation
- 2001-01-31 JP JP2001022954A patent/JP3513493B2/ja not_active Expired - Fee Related
- 2001-01-31 PL PL01345528A patent/PL345528A1/xx unknown
- 2001-01-31 ZA ZA200100864A patent/ZA200100864B/xx unknown
- 2001-01-31 KR KR10-2001-0004591A patent/KR100463369B1/ko not_active Expired - Fee Related
- 2001-01-31 BR BR0100234-1A patent/BR0100234A/pt not_active IP Right Cessation
- 2001-01-31 AU AU16747/01A patent/AU774808B2/en not_active Ceased
-
2002
- 2002-01-16 HK HK02100331.6A patent/HK1039117B/zh not_active IP Right Cessation
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