RU2293738C2 - Способ получения производного индолиноспиропирана - Google Patents
Способ получения производного индолиноспиропирана Download PDFInfo
- Publication number
- RU2293738C2 RU2293738C2 RU2002132259/04A RU2002132259A RU2293738C2 RU 2293738 C2 RU2293738 C2 RU 2293738C2 RU 2002132259/04 A RU2002132259/04 A RU 2002132259/04A RU 2002132259 A RU2002132259 A RU 2002132259A RU 2293738 C2 RU2293738 C2 RU 2293738C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- indoline
- resin
- formula
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 239000011347 resin Substances 0.000 claims abstract description 35
- -1 trifluoromethyl formyl Chemical group 0.000 claims abstract description 20
- 239000012298 atmosphere Substances 0.000 claims abstract description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 229920000642 polymer Polymers 0.000 claims description 25
- 239000008187 granular material Substances 0.000 claims description 24
- 239000000725 suspension Substances 0.000 claims description 16
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 10
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- WLFGGJFWKXTOGJ-UHFFFAOYSA-N 2,3-dihydroindol-1-amine Chemical compound C1=CC=C2N(N)CCC2=C1 WLFGGJFWKXTOGJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 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
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 229920005990 polystyrene resin Polymers 0.000 claims description 4
- 239000001384 succinic acid Substances 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
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-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
- UKXKGTGQIITIAB-UHFFFAOYSA-N spiro[1,3-dihydroindole-2,2'-pyran] Chemical compound C1C2=CC=CC=C2NC11OC=CC=C1 UKXKGTGQIITIAB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000004900 laundering Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 12
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- 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
- 239000000047 product Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000007787 solid Substances 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 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 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- HBKLIWVBQOAZLB-UHFFFAOYSA-N 1-(6-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(O)=CC=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O HBKLIWVBQOAZLB-UHFFFAOYSA-N 0.000 description 2
- 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 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
- XTWNLVIKPDMDRI-UHFFFAOYSA-N 1-(8-methoxy-1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound O1C=2C(OC)=CC([N+]([O-])=O)=CC=2C=CC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O XTWNLVIKPDMDRI-UHFFFAOYSA-N 0.000 description 2
- KFYMBZXPLGNXNN-UHFFFAOYSA-N 1-(8-methoxy-1',3',3'-trimethylspiro[chromene-2,2'-indole]-5'-yl)pyrrolidine-2,5-dione Chemical compound O1C=2C(OC)=CC=CC=2C=CC1(C(C1=C2)(C)C)N(C)C1=CC=C2N1C(=O)CCC1=O KFYMBZXPLGNXNN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RETCQDMPXNHTGC-UHFFFAOYSA-N 1-[1',3',3'-trimethyl-6-(trifluoromethoxy)spiro[chromene-2,2'-indole]-5'-yl]pyrrolidine-2,5-dione Chemical compound C1=C2C(C)(C)C3(C=CC4=CC(OC(F)(F)F)=CC=C4O3)N(C)C2=CC=C1N1C(=O)CCC1=O RETCQDMPXNHTGC-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
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 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 2
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 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
- 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
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- VUCNQOPCYRJCGQ-UHFFFAOYSA-N 2-[4-(hydroxymethyl)phenoxy]acetic acid Chemical compound OCC1=CC=C(OCC(O)=O)C=C1 VUCNQOPCYRJCGQ-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
- WQUZBERVMUEJTD-UHFFFAOYSA-N 2-hydroxy-5-(trifluoromethoxy)benzaldehyde Chemical compound OC1=CC=C(OC(F)(F)F)C=C1C=O WQUZBERVMUEJTD-UHFFFAOYSA-N 0.000 description 1
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-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
- IPPQNXSAJZOTJZ-UHFFFAOYSA-N 3-methylsalicylaldehyde Chemical compound CC1=CC=CC(C=O)=C1O IPPQNXSAJZOTJZ-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
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical class C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-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
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-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
- ZVCQQLGWGRTXGC-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC=C(O)C(C=O)=C1 ZVCQQLGWGRTXGC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 CC1(*)c(cc(*CCC(OCC2CCCC2)=O)cc2)c2N(*)C1=C Chemical compound CC1(*)c(cc(*CCC(OCC2CCCC2)=O)cc2)c2N(*)C1=C 0.000 description 1
- ZYFBUDZAWCAOEH-NQBHXWOUSA-N CC[C@@H](C)[C@@H](N)[IH][C@H](C)C(CC)=C(C)C Chemical compound CC[C@@H](C)[C@@H](N)[IH][C@H](C)C(CC)=C(C)C ZYFBUDZAWCAOEH-NQBHXWOUSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 240000001414 Eucalyptus viminalis Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- 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 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 150000002894 organic compounds Chemical class 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/585,108 | 2000-05-31 | ||
| US09/585,108 US6521753B1 (en) | 2000-05-31 | 2000-05-31 | Indolinospiropyran compounds and methods for their manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002132259A RU2002132259A (ru) | 2004-04-10 |
| RU2293738C2 true RU2293738C2 (ru) | 2007-02-20 |
Family
ID=24340075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002132259/04A RU2293738C2 (ru) | 2000-05-31 | 2001-05-24 | Способ получения производного индолиноспиропирана |
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) | AU6661201A (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) | MY135395A (enExample) |
| RU (1) | RU2293738C2 (enExample) |
| TW (1) | TWI300412B (enExample) |
| WO (1) | WO2001092265A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
Families Citing this family (11)
| 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 |
| BR112012023662A2 (pt) | 2010-03-19 | 2016-08-16 | Fujifilm Corp | composição fotossensível à coloração, precursor de chapa de impressão litográfica e método de fabricação de chapa |
| 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 |
| 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 |
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| US4556605A (en) * | 1982-09-09 | 1985-12-03 | Kabushiki Kaisha Suwa Seikosha | Photochromic coating composition and photochromic synthetic resin ophthalmic lens |
| US5066818A (en) * | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
| WO1994022850A1 (en) * | 1993-03-30 | 1994-10-13 | Pilkington Plc | Photochromic naphthopyran compounds |
| 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 |
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| 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 |
| 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 |
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| AU638815B2 (en) | 1990-03-29 | 1993-07-08 | Tokuyama Soda Kabushiki Kaisha | Photochromic compound, composition and use thereof |
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| 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 ES ES01944175T patent/ES2236248T3/es not_active Expired - Lifetime
- 2001-05-24 AU AU6661201A patent/AU6661201A/xx active Pending
- 2001-05-24 WO PCT/US2001/017018 patent/WO2001092265A2/en not_active Ceased
- 2001-05-24 CA CA002410673A patent/CA2410673C/en not_active Expired - Fee Related
- 2001-05-24 AU AU2001266612A patent/AU2001266612B2/en not_active Ceased
- 2001-05-24 KR KR1020027016312A patent/KR100760963B1/ko not_active Expired - Fee Related
- 2001-05-24 AT AT01944175T patent/ATE286056T1/de not_active IP Right Cessation
- 2001-05-24 EP EP01944175A patent/EP1299391B1/en not_active Expired - Lifetime
- 2001-05-24 IL IL15308401A patent/IL153084A0/xx not_active IP Right Cessation
- 2001-05-24 BR BR0111398-4A patent/BR0111398A/pt not_active IP Right Cessation
- 2001-05-24 RU RU2002132259/04A patent/RU2293738C2/ru not_active IP Right Cessation
- 2001-05-24 MX MXPA02011928A patent/MXPA02011928A/es not_active Application Discontinuation
- 2001-05-24 DE DE60108126T patent/DE60108126T2/de not_active Expired - Fee Related
- 2001-05-24 CN CNB01813470XA patent/CN100475818C/zh not_active Expired - Fee Related
- 2001-05-24 JP JP2002500878A patent/JP4885403B2/ja not_active Expired - Fee Related
- 2001-05-29 MY MYPI20040648A patent/MY135395A/en unknown
- 2001-05-29 MY MYPI20012551A patent/MY118670A/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
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|---|---|---|---|---|
| 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 |
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| WO1994022850A1 (en) * | 1993-03-30 | 1994-10-13 | Pilkington Plc | Photochromic naphthopyran compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1051685A1 (en) | 2003-08-15 |
| TWI300412B (en) | 2008-09-01 |
| DE60108126T2 (de) | 2006-03-02 |
| KR100760963B1 (ko) | 2007-10-04 |
| MY135395A (en) | 2008-04-30 |
| WO2001092265A3 (en) | 2002-03-28 |
| WO2001092265A2 (en) | 2001-12-06 |
| CA2410673C (en) | 2007-11-13 |
| US20020087010A1 (en) | 2002-07-04 |
| US6521753B1 (en) | 2003-02-18 |
| MXPA02011928A (es) | 2004-09-06 |
| EP1299391B1 (en) | 2004-12-29 |
| ATE286056T1 (de) | 2005-01-15 |
| RU2002132259A (ru) | 2004-04-10 |
| JP2003535095A (ja) | 2003-11-25 |
| CN1444586A (zh) | 2003-09-24 |
| CN100475818C (zh) | 2009-04-08 |
| MY118670A (en) | 2004-12-31 |
| CA2410673A1 (en) | 2001-12-06 |
| JP4885403B2 (ja) | 2012-02-29 |
| ES2236248T3 (es) | 2005-07-16 |
| AU6661201A (en) | 2001-12-11 |
| AU2001266612B2 (en) | 2005-09-15 |
| KR20030007800A (ko) | 2003-01-23 |
| BR0111398A (pt) | 2004-01-13 |
| DE60108126D1 (de) | 2005-02-03 |
| IL153084A0 (en) | 2003-06-24 |
| EP1299391A2 (en) | 2003-04-09 |
| US6803471B2 (en) | 2004-10-12 |
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