CA2410673C - Indolinospiropyran compounds and methods for their manufacture - Google Patents
Indolinospiropyran compounds and methods for their manufacture Download PDFInfo
- Publication number
- CA2410673C CA2410673C CA002410673A CA2410673A CA2410673C CA 2410673 C CA2410673 C CA 2410673C CA 002410673 A CA002410673 A CA 002410673A CA 2410673 A CA2410673 A CA 2410673A CA 2410673 C CA2410673 C CA 2410673C
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- Prior art keywords
- alkyl
- phenyl
- ring
- compound
- resin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000011347 resin Substances 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 239000011324 bead Substances 0.000 claims description 21
- -1 ethoxycarbonyl ethyl Chemical group 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 238000011068 loading method Methods 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 9
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 9
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- 239000003875 Wang resin Substances 0.000 claims description 6
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- MKDCJAPHKZPKOU-UHFFFAOYSA-N 1-nitro-2,3-dihydroindole Chemical class C1=CC=C2N([N+](=O)[O-])CCC2=C1 MKDCJAPHKZPKOU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000006682 monohaloalkyl group Chemical group 0.000 claims description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 3
- WLFGGJFWKXTOGJ-UHFFFAOYSA-N 2,3-dihydroindol-1-amine Chemical compound C1=CC=C2N(N)CCC2=C1 WLFGGJFWKXTOGJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- 229920005990 polystyrene resin Polymers 0.000 claims description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
- VUCNQOPCYRJCGQ-UHFFFAOYSA-N 2-[4-(hydroxymethyl)phenoxy]acetic acid Chemical compound OCC1=CC=C(OCC(O)=O)C=C1 VUCNQOPCYRJCGQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- TZCWNVIKUJQJAI-UHFFFAOYSA-N diphenylmethanamine;2-(4-hydroxy-3-methoxyphenoxy)butanoic acid Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1.CCC(C(O)=O)OC1=CC=C(O)C(OC)=C1 TZCWNVIKUJQJAI-UHFFFAOYSA-N 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims 2
- 239000001384 succinic acid Substances 0.000 claims 2
- ZZZNWUXJAHWCGF-UHFFFAOYSA-N 2-[4-(hydroxymethyl)-3-methoxyphenoxy]butanoic acid;n-methyl-1,1-diphenylmethanamine Chemical compound C=1C=CC=CC=1C(NC)C1=CC=CC=C1.CCC(C(O)=O)OC1=CC=C(CO)C(OC)=C1 ZZZNWUXJAHWCGF-UHFFFAOYSA-N 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract description 12
- 229960002317 succinimide Drugs 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000007142 ring opening reaction Methods 0.000 abstract description 3
- 125000001041 indolyl group Chemical group 0.000 abstract description 2
- 239000007790 solid phase Substances 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KGKIIOQCBMYRNC-UHFFFAOYSA-N 1,3,3-trimethyl-2h-indol-5-amine Chemical compound NC1=CC=C2N(C)CC(C)(C)C2=C1 KGKIIOQCBMYRNC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DEZBRITWRIGOMA-UHFFFAOYSA-N 1,3,3-trimethyl-5-nitro-2h-indole Chemical compound [O-][N+](=O)C1=CC=C2N(C)CC(C)(C)C2=C1 DEZBRITWRIGOMA-UHFFFAOYSA-N 0.000 description 3
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 description 3
- JHWWTMNOCGPEFE-UHFFFAOYSA-N 1-(1',3',3',6-tetramethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(C)=CC=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O JHWWTMNOCGPEFE-UHFFFAOYSA-N 0.000 description 2
- NMOPJBZQVOVISM-UHFFFAOYSA-N 1-(1',3',3'-trimethylspiro[chromene-2,2'-indole]-5-yl)pyrrolidine-2,5-dione Chemical compound CN1C2=CC=CC=C2C(C)(C)C1(C=CC1=2)OC1=CC=CC=2N1C(=O)CCC1=O NMOPJBZQVOVISM-UHFFFAOYSA-N 0.000 description 2
- IKQNESDPQJDBLL-UHFFFAOYSA-N 1-(6,8-dibromo-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(Br)=CC(Br)=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O IKQNESDPQJDBLL-UHFFFAOYSA-N 0.000 description 2
- MJGXHARXVGZLEU-UHFFFAOYSA-N 1-(6,8-dichloro-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(Cl)=CC(Cl)=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O MJGXHARXVGZLEU-UHFFFAOYSA-N 0.000 description 2
- BHDQSBFEQZHSJP-UHFFFAOYSA-N 1-(6,8-ditert-butyl-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=C(C(=CC(=C4)C(C)(C)C)C(C)(C)C)O3)N(C)C2=CC=C1N1C(=O)CCC1=O BHDQSBFEQZHSJP-UHFFFAOYSA-N 0.000 description 2
- KLHSXCOKFVJGAQ-UHFFFAOYSA-N 1-(6-chloro-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(Cl)=CC=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O KLHSXCOKFVJGAQ-UHFFFAOYSA-N 0.000 description 2
- NUBATWMEPIWPFJ-UHFFFAOYSA-N 1-(6-methoxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=CC2=CC(OC)=CC=C2OC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O NUBATWMEPIWPFJ-UHFFFAOYSA-N 0.000 description 2
- PAYBOMGQAHOBOT-UHFFFAOYSA-N 1-(7-methoxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound O1C2=CC(OC)=CC=C2C=CC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O PAYBOMGQAHOBOT-UHFFFAOYSA-N 0.000 description 2
- RNLTYQNNXCFRFH-UHFFFAOYSA-N 1-(8-ethoxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound O1C=2C(OCC)=CC=CC=2C=CC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O RNLTYQNNXCFRFH-UHFFFAOYSA-N 0.000 description 2
- FMYOJFJZBQLOLD-UHFFFAOYSA-N 1-(8-hydroxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC=CC(O)=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O FMYOJFJZBQLOLD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- OTHZLEGWKSXSIF-UHFFFAOYSA-N 4-amino-4-oxo-3-(1,3,3-trimethyl-2h-indol-5-yl)butanoic acid Chemical compound OC(=O)CC(C(N)=O)C1=CC=C2N(C)CC(C)(C)C2=C1 OTHZLEGWKSXSIF-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 150000002476 indolines Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- CZTCZDFGLUDUQP-UHFFFAOYSA-N 1',3',3'-trimethylspiro[chromene-2,2'-indole] Chemical compound O1C2=CC=CC=C2C=CC21C(C)(C)C1=CC=CC=C1N2C CZTCZDFGLUDUQP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ANWRNVSTLHOZBK-UHFFFAOYSA-N 1-(1',3',3',8-tetramethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC=CC(C)=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O ANWRNVSTLHOZBK-UHFFFAOYSA-N 0.000 description 1
- YXBHNJLIMRZQOW-UHFFFAOYSA-N 1-(1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(=CC=C4O3)[N+]([O-])=O)N(C)C2=CC=C1N1C(=O)CCC1=O YXBHNJLIMRZQOW-UHFFFAOYSA-N 0.000 description 1
- WFLSZXOOYPLBPL-UHFFFAOYSA-N 1-(5,7-dimethoxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound O1C2=CC(OC)=CC(OC)=C2C=CC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O WFLSZXOOYPLBPL-UHFFFAOYSA-N 0.000 description 1
- GBDCVUQWYMLOPD-UHFFFAOYSA-N 1-(6,8-diiodo-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(I)=CC(I)=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O GBDCVUQWYMLOPD-UHFFFAOYSA-N 0.000 description 1
- YHEVDTJUJUPPLL-UHFFFAOYSA-N 1-(6-bromo-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(Br)=CC=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O YHEVDTJUJUPPLL-UHFFFAOYSA-N 0.000 description 1
- RMUPQYCVPHBOLW-UHFFFAOYSA-N 1-(6-bromo-8-methoxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound O1C=2C(OC)=CC(Br)=CC=2C=CC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O RMUPQYCVPHBOLW-UHFFFAOYSA-N 0.000 description 1
- OFKXVWGLGPDGFZ-UHFFFAOYSA-N 1-(6-fluoro-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(F)=CC=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O OFKXVWGLGPDGFZ-UHFFFAOYSA-N 0.000 description 1
- JESNVFSYJIBSLT-UHFFFAOYSA-N 1-(6-tert-butyl-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(=CC=C4O3)C(C)(C)C)N(C)C2=CC=C1N1C(=O)CCC1=O JESNVFSYJIBSLT-UHFFFAOYSA-N 0.000 description 1
- OVUWBSNHTNDHHW-UHFFFAOYSA-N 1-(8-tert-butyl-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=C(C(=CC=C4)C(C)(C)C)O3)N(C)C2=CC=C1N1C(=O)CCC1=O OVUWBSNHTNDHHW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WPBZYXTYIATCHM-UHFFFAOYSA-N 2,3,4-trimethyl-2,3-dihydro-1h-indole Chemical compound C1=CC(C)=C2C(C)C(C)NC2=C1 WPBZYXTYIATCHM-UHFFFAOYSA-N 0.000 description 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- MYWSBJKVOUZCIA-UHFFFAOYSA-N 2-hydroxy-3,5-diiodobenzaldehyde Chemical compound OC1=C(I)C=C(I)C=C1C=O MYWSBJKVOUZCIA-UHFFFAOYSA-N 0.000 description 1
- FQRQWPNYJOFDLO-UHFFFAOYSA-N 2-hydroxy-4,6-dimethoxybenzaldehyde Chemical compound COC1=CC(O)=C(C=O)C(OC)=C1 FQRQWPNYJOFDLO-UHFFFAOYSA-N 0.000 description 1
- ZBOUXALQDLLARY-UHFFFAOYSA-N 2-hydroxy-5-methylbenzene-1,3-dicarbaldehyde Chemical compound CC1=CC(C=O)=C(O)C(C=O)=C1 ZBOUXALQDLLARY-UHFFFAOYSA-N 0.000 description 1
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 1
- RRIQVLZDOZPJTH-UHFFFAOYSA-N 3,5-di-tert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=C(O)C(C(C)(C)C)=C1 RRIQVLZDOZPJTH-UHFFFAOYSA-N 0.000 description 1
- JHZOXYGFQMROFJ-UHFFFAOYSA-N 3,5-dibromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(Br)C=C1C=O JHZOXYGFQMROFJ-UHFFFAOYSA-N 0.000 description 1
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- OFQBYHLLIJGMNP-UHFFFAOYSA-N 3-ethoxy-2-hydroxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1O OFQBYHLLIJGMNP-UHFFFAOYSA-N 0.000 description 1
- ROILLNJICXGZQQ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC=CC(C=O)=C1O ROILLNJICXGZQQ-UHFFFAOYSA-N 0.000 description 1
- UWAUQFYLBRSXNQ-UHFFFAOYSA-N 5'-(2,5-dioxopyrrolidin-1-yl)-1',3',3',6-tetramethylspiro[chromene-2,2'-indole]-8-carbaldehyde Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(C)=CC(C=O)=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O UWAUQFYLBRSXNQ-UHFFFAOYSA-N 0.000 description 1
- MMFKBTPDEVLIOR-UHFFFAOYSA-N 5-bromo-2-hydroxy-3-methoxybenzaldehyde Chemical compound COC1=CC(Br)=CC(C=O)=C1O MMFKBTPDEVLIOR-UHFFFAOYSA-N 0.000 description 1
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 1
- FDUBQNUDZOGOFE-UHFFFAOYSA-N 5-fluoro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(F)C=C1C=O FDUBQNUDZOGOFE-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- RNGQTPOUTNKYLA-UHFFFAOYSA-N oxolane-2,5-dione Chemical compound O=C1CCC(=O)O1.O=C1CCC(=O)O1 RNGQTPOUTNKYLA-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Eyeglasses (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/585,108 US6521753B1 (en) | 2000-05-31 | 2000-05-31 | Indolinospiropyran compounds and methods for their manufacture |
| US09/585,108 | 2000-05-31 | ||
| PCT/US2001/017018 WO2001092265A2 (en) | 2000-05-31 | 2001-05-24 | Indolinospiropyran compounds and methods for their manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2410673A1 CA2410673A1 (en) | 2001-12-06 |
| CA2410673C true CA2410673C (en) | 2007-11-13 |
Family
ID=24340075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002410673A Expired - Fee Related CA2410673C (en) | 2000-05-31 | 2001-05-24 | Indolinospiropyran compounds and methods for their manufacture |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US6521753B1 (enExample) |
| EP (1) | EP1299391B1 (enExample) |
| JP (1) | JP4885403B2 (enExample) |
| KR (1) | KR100760963B1 (enExample) |
| CN (1) | CN100475818C (enExample) |
| AT (1) | ATE286056T1 (enExample) |
| AU (2) | AU2001266612B2 (enExample) |
| BR (1) | BR0111398A (enExample) |
| CA (1) | CA2410673C (enExample) |
| DE (1) | DE60108126T2 (enExample) |
| ES (1) | ES2236248T3 (enExample) |
| IL (1) | IL153084A0 (enExample) |
| MX (1) | MXPA02011928A (enExample) |
| MY (2) | MY118670A (enExample) |
| RU (1) | RU2293738C2 (enExample) |
| TW (1) | TWI300412B (enExample) |
| WO (1) | WO2001092265A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6521753B1 (en) | 2000-05-31 | 2003-02-18 | Johnson & Johnson Vision Care, Inc. | Indolinospiropyran compounds and methods for their manufacture |
| TWI263640B (en) * | 2001-12-19 | 2006-10-11 | Bristol Myers Squibb Co | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| US20040259975A1 (en) * | 2003-06-18 | 2004-12-23 | Robillard Jean J. | System and method for forming photobleachable ink compositions |
| CN100408590C (zh) * | 2003-08-12 | 2008-08-06 | 上海迪赛诺医药科技开发有限公司 | 螺吡喃和螺噁嗪类光致变色化合物修饰核苷的方法 |
| US7425406B2 (en) | 2004-07-27 | 2008-09-16 | Fujifilm Corporation | Lithographic printing plate precursor and lithographic printing method |
| RU2358977C1 (ru) * | 2008-04-02 | 2009-06-20 | Московская государственная академия тонкой химической технологии им. М.В. Ломоносова Государственное образовательное учреждение высшего профессионального образования | 5-формил-замещенные индолиновые спиробензопираны и способ их получения |
| CN102812402B (zh) | 2010-03-19 | 2015-08-05 | 富士胶片株式会社 | 着色感光性组合物、平版印刷版原版和制版方法 |
| CN103288841B (zh) * | 2013-05-28 | 2015-03-04 | 中国科学技术大学 | 一种螺吡喃取代二乙炔及其制备方法和应用 |
| RU2569898C1 (ru) * | 2014-12-16 | 2015-12-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | Способ получения этил 2-амино-2',5-диоксо-5'-фенил-3-циано-1',2'-дигидро-5h-спиро{индено[1,2-b]пиран-4,3'-пиррол}-4'-карбоксилатов |
| RU2694904C1 (ru) * | 2019-02-20 | 2019-07-18 | Федеральное Государственное Бюджетное Учреждение Науки Институт Биохимической Физики Им. Н.М. Эмануэля Российской Академии Наук (Ибхф Ран) | Фотохромные производные 5'-гидроксиметил-6-нитро-1',3',3'-триметилспиро[2Н-1-бензопиран-2,2'-индолина] |
| US11253816B2 (en) | 2019-05-10 | 2022-02-22 | Saudi Arabian Oil Company | Direct oxidation of hydrogen sulfide in a hydroprocessing recycle gas stream with hydrogen purification |
| CN113046093B (zh) * | 2021-03-24 | 2022-06-07 | 北京大学 | 基于螺吡喃衍生物分子开关的可图案化液晶薄膜及其制备方法和应用 |
| CN113024571B (zh) * | 2021-03-24 | 2022-01-11 | 北京大学 | 具有颜色、荧光和液晶性三重开关效果的螺吡喃衍生物及其制备方法和应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4215010A (en) | 1978-09-08 | 1980-07-29 | American Optical Corporation | Photochromic compounds |
| US4342668A (en) | 1978-09-08 | 1982-08-03 | American Optical Corporation | Photochromic compounds |
| JPS59202270A (ja) * | 1983-04-28 | 1984-11-16 | Seiko Epson Corp | フオトクロミツクコ−テイング用組成物 |
| US4556605A (en) | 1982-09-09 | 1985-12-03 | Kabushiki Kaisha Suwa Seikosha | Photochromic coating composition and photochromic synthetic resin ophthalmic lens |
| SU1127271A1 (ru) * | 1983-08-05 | 1995-10-10 | Институт Тонкой Органической Химии Им.А.Л.Мнджояна | Гидрохлорид 6,7- диметокси- 4,4 -спиротетрагидропиран-n- (3-фенил-2-пропенил) -1,2,3, 4-тетрагидроизохинолина, обладающий центральным м-холинолитическим действием |
| US4637698A (en) | 1983-11-04 | 1987-01-20 | Ppg Industries, Inc. | Photochromic compound and articles containing the same |
| JPS61228402A (ja) * | 1985-03-29 | 1986-10-11 | ピーピージー インダストリーズ インコーポレーテツド | ホトクロミツクプラスチツク物品およびその製造法 |
| AU554441B2 (en) * | 1985-03-29 | 1986-08-21 | Ppg Industries Ohio, Inc. | Photochromic plastic lenses |
| GB8611837D0 (en) | 1986-05-15 | 1986-06-25 | Plessey Co Plc | Photochromic spiropyran compounds |
| US4816584A (en) | 1986-11-12 | 1989-03-28 | Ppg Industries, Inc. | Photochromic spiro(indoline)benzoxazines |
| US4931221A (en) | 1988-12-30 | 1990-06-05 | Ppg Industries, Inc. | Photochromic spiropyran compounds |
| US5066818A (en) * | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| US5246989A (en) | 1990-03-29 | 1993-09-21 | Tokuyama Soda Kabishiki Kaisha | Photochromic compound, composition and use thereof |
| GB9306587D0 (en) | 1993-03-30 | 1993-05-26 | Pilkington Plc | Photochromic compounds |
| US5645768A (en) | 1993-06-28 | 1997-07-08 | Optische Werke G. Rodenstock | Photochromic compounds |
| JP2975519B2 (ja) * | 1993-12-10 | 1999-11-10 | 大日精化工業株式会社 | 新規フォトクロミック化合物 |
| US6521753B1 (en) | 2000-05-31 | 2003-02-18 | Johnson & Johnson Vision Care, Inc. | Indolinospiropyran compounds and methods for their manufacture |
-
2000
- 2000-05-31 US US09/585,108 patent/US6521753B1/en not_active Expired - Fee Related
-
2001
- 2001-05-24 IL IL15308401A patent/IL153084A0/xx not_active IP Right Cessation
- 2001-05-24 MX MXPA02011928A patent/MXPA02011928A/es not_active Application Discontinuation
- 2001-05-24 AT AT01944175T patent/ATE286056T1/de not_active IP Right Cessation
- 2001-05-24 JP JP2002500878A patent/JP4885403B2/ja not_active Expired - Fee Related
- 2001-05-24 ES ES01944175T patent/ES2236248T3/es not_active Expired - Lifetime
- 2001-05-24 CN CNB01813470XA patent/CN100475818C/zh not_active Expired - Fee Related
- 2001-05-24 BR BR0111398-4A patent/BR0111398A/pt not_active IP Right Cessation
- 2001-05-24 CA CA002410673A patent/CA2410673C/en not_active Expired - Fee Related
- 2001-05-24 EP EP01944175A patent/EP1299391B1/en not_active Expired - Lifetime
- 2001-05-24 AU AU2001266612A patent/AU2001266612B2/en not_active Ceased
- 2001-05-24 WO PCT/US2001/017018 patent/WO2001092265A2/en not_active Ceased
- 2001-05-24 DE DE60108126T patent/DE60108126T2/de not_active Expired - Fee Related
- 2001-05-24 KR KR1020027016312A patent/KR100760963B1/ko not_active Expired - Fee Related
- 2001-05-24 RU RU2002132259/04A patent/RU2293738C2/ru not_active IP Right Cessation
- 2001-05-24 AU AU6661201A patent/AU6661201A/xx active Pending
- 2001-05-29 MY MYPI20012551A patent/MY118670A/en unknown
- 2001-05-29 MY MYPI20040648A patent/MY135395A/en unknown
- 2001-05-31 TW TW090113116A patent/TWI300412B/zh not_active IP Right Cessation
-
2002
- 2002-01-28 US US10/058,994 patent/US6803471B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4885403B2 (ja) | 2012-02-29 |
| IL153084A0 (en) | 2003-06-24 |
| ES2236248T3 (es) | 2005-07-16 |
| US6803471B2 (en) | 2004-10-12 |
| CN1444586A (zh) | 2003-09-24 |
| AU2001266612B2 (en) | 2005-09-15 |
| DE60108126D1 (de) | 2005-02-03 |
| EP1299391B1 (en) | 2004-12-29 |
| DE60108126T2 (de) | 2006-03-02 |
| CA2410673A1 (en) | 2001-12-06 |
| TWI300412B (en) | 2008-09-01 |
| HK1051685A1 (en) | 2003-08-15 |
| US20020087010A1 (en) | 2002-07-04 |
| BR0111398A (pt) | 2004-01-13 |
| KR100760963B1 (ko) | 2007-10-04 |
| RU2002132259A (ru) | 2004-04-10 |
| US6521753B1 (en) | 2003-02-18 |
| JP2003535095A (ja) | 2003-11-25 |
| RU2293738C2 (ru) | 2007-02-20 |
| MY118670A (en) | 2004-12-31 |
| KR20030007800A (ko) | 2003-01-23 |
| EP1299391A2 (en) | 2003-04-09 |
| AU6661201A (en) | 2001-12-11 |
| MY135395A (en) | 2008-04-30 |
| CN100475818C (zh) | 2009-04-08 |
| MXPA02011928A (es) | 2004-09-06 |
| ATE286056T1 (de) | 2005-01-15 |
| WO2001092265A3 (en) | 2002-03-28 |
| WO2001092265A2 (en) | 2001-12-06 |
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