IL35047A - In -rile and the troiryl-2-amino-alkoxy citrons and their preparation - Google Patents
In -rile and the troiryl-2-amino-alkoxy citrons and their preparationInfo
- Publication number
- IL35047A IL35047A IL35047A IL3504770A IL35047A IL 35047 A IL35047 A IL 35047A IL 35047 A IL35047 A IL 35047A IL 3504770 A IL3504770 A IL 3504770A IL 35047 A IL35047 A IL 35047A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- group
- reaction
- styryl
- acid addition
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 51
- -1 2-quinolyl Chemical group 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 24
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 6
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 5
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000747 amidyl group Chemical group [H][N-]* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 239000007806 chemical reaction intermediate Substances 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- DWOAVPRICOHERA-UHFFFAOYSA-N 4-[2-[2-(2-pyridin-2-ylethenyl)phenoxy]ethyl]morpholine Chemical compound C=1C=CC=C(C=CC=2N=CC=CC=2)C=1OCCN1CCOCC1 DWOAVPRICOHERA-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HCUBLNPEQJJSCC-UHFFFAOYSA-N n,n-dimethyl-2-[2-(2-phenylethenyl)phenoxy]ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C=CC1=CC=CC=C1 HCUBLNPEQJJSCC-UHFFFAOYSA-N 0.000 claims 1
- WMAMGISKTNPWOO-UHFFFAOYSA-N n,n-dimethyl-2-[2-(2-pyrazin-2-ylethenyl)phenoxy]ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C=CC1=CN=CC=N1 WMAMGISKTNPWOO-UHFFFAOYSA-N 0.000 claims 1
- ODCVBQULEFUXOS-UHFFFAOYSA-N n,n-dimethyl-2-[2-(2-quinolin-2-ylethenyl)phenoxy]ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C=CC1=CC=C(C=CC=C2)C2=N1 ODCVBQULEFUXOS-UHFFFAOYSA-N 0.000 claims 1
- AEQMNJCMKYAQDN-UHFFFAOYSA-N n,n-dimethyl-2-[2-[2-(6-methylpyridin-2-yl)ethenyl]phenoxy]ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C=CC1=CC=CC(C)=N1 AEQMNJCMKYAQDN-UHFFFAOYSA-N 0.000 claims 1
- YGDZSZYJGIFRFL-UHFFFAOYSA-N n-methyl-2-[2-(2-pyridin-2-ylethenyl)phenoxy]ethanamine Chemical compound CNCCOC1=CC=CC=C1C=CC1=CC=CC=N1 YGDZSZYJGIFRFL-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000003826 tablet Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 125000005504 styryl group Chemical group 0.000 description 15
- 239000000829 suppository Substances 0.000 description 13
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229940093499 ethyl acetate Drugs 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- AUQITUJCWBROPQ-UHFFFAOYSA-N 2-[2-[2-(2-chloroethoxy)phenyl]ethenyl]pyridine Chemical compound ClCCOC1=CC=CC=C1C=CC1=CC=CC=N1 AUQITUJCWBROPQ-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- WJYNWFSNRMEPMF-UHFFFAOYSA-N 2-[2-(diethoxyphosphorylmethyl)phenoxy]-N,N-dimethylethanamine Chemical compound CN(CCOC1=C(CP(OCC)(OCC)=O)C=CC=C1)C WJYNWFSNRMEPMF-UHFFFAOYSA-N 0.000 description 7
- TWMYSXRSVLFCGX-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]benzaldehyde Chemical compound CN(C)CCOC1=CC=CC=C1C=O TWMYSXRSVLFCGX-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- RCAVMXODXXMCER-UHFFFAOYSA-N n,n-dimethyl-2-[2-(2-pyridin-2-ylethenyl)phenoxy]ethanamine;hydrochloride Chemical compound Cl.CN(C)CCOC1=CC=CC=C1C=CC1=CC=CC=N1 RCAVMXODXXMCER-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 150000003008 phosphonic acid esters Chemical class 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 229910002012 Aerosil® Inorganic materials 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DTNXIWBODCJJEU-UHFFFAOYSA-N [2-(2-pyridin-2-ylethenyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C=CC1=CC=CC=N1 DTNXIWBODCJJEU-UHFFFAOYSA-N 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- LLCYXGBLEDYIDN-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-1-phenylethanone Chemical compound CN(C)CCOCC(=O)C1=CC=CC=C1 LLCYXGBLEDYIDN-UHFFFAOYSA-N 0.000 description 3
- BDQWNFGSQOXARB-UHFFFAOYSA-N 2-[3-(dimethylamino)propoxy]-1-phenylethanone Chemical compound CN(C)CCCOCC(=O)C1=CC=CC=C1 BDQWNFGSQOXARB-UHFFFAOYSA-N 0.000 description 3
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 3
- NIFAUKBQIAURIM-UHFFFAOYSA-N 4-(chloromethyl)-3,5-dimethyl-1,2-oxazole Chemical compound CC1=NOC(C)=C1CCl NIFAUKBQIAURIM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- UZEUGNPDHSAXJI-UHFFFAOYSA-N N,N-dimethyl-2-[2-[2-(1-methylbenzimidazol-2-yl)ethenyl]phenoxy]ethanamine dihydrochloride Chemical compound Cl.Cl.CN(C)CCOC1=CC=CC=C1C=CC1=NC2=CC=CC=C2N1C UZEUGNPDHSAXJI-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NQUAUTVQZJQLIZ-UHFFFAOYSA-N n,n-dimethyl-2-[2-(2-phenylethenyl)phenoxy]ethanamine;hydrochloride Chemical compound Cl.CN(C)CCOC1=CC=CC=C1C=CC1=CC=CC=C1 NQUAUTVQZJQLIZ-UHFFFAOYSA-N 0.000 description 3
- ZMHZFJLJDOTWDW-UHFFFAOYSA-N n,n-dimethyl-2-[2-(2-pyridin-2-ylethenyl)phenoxy]ethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C=CC1=CC=CC=N1 ZMHZFJLJDOTWDW-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- DSHCOEWHRLVOTF-UHFFFAOYSA-N 2-[3-(dimethylamino)propoxy]benzaldehyde Chemical compound CN(C)CCCOC1=CC=CC=C1C=O DSHCOEWHRLVOTF-UHFFFAOYSA-N 0.000 description 2
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- ZWBJJNWJUXXFNP-UHFFFAOYSA-N 5-(chloromethyl)-3-methyl-1,2-oxazole Chemical compound CC=1C=C(CCl)ON=1 ZWBJJNWJUXXFNP-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
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- 239000012442 inert solvent Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
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- 150000003440 styrenes Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- NXNDEWNGCMCWMA-UHFFFAOYSA-N 2-(2-quinolin-2-ylethenyl)phenol Chemical compound OC1=CC=CC=C1C=CC1=CC=C(C=CC=C2)C2=N1 NXNDEWNGCMCWMA-UHFFFAOYSA-N 0.000 description 1
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- SLNFFKAUEGIFPB-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]benzaldehyde Chemical compound CCN(CC)CCOC1=CC=CC=C1C=O SLNFFKAUEGIFPB-UHFFFAOYSA-N 0.000 description 1
- SFLLGCQYLKKZQS-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OCCN(C)C)=C1 SFLLGCQYLKKZQS-UHFFFAOYSA-N 0.000 description 1
- FWWANUZXQIGOOI-UHFFFAOYSA-N 2-[2-[2-(2-chloroethoxy)phenyl]ethenyl]quinoline Chemical compound ClCCOC1=CC=CC=C1C=CC1=CC=C(C=CC=C2)C2=N1 FWWANUZXQIGOOI-UHFFFAOYSA-N 0.000 description 1
- KPRPFTOLWQQUAV-OCVAFRRMSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCOCC1 KPRPFTOLWQQUAV-OCVAFRRMSA-N 0.000 description 1
- GYXWNSDLDXGMGU-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine Chemical compound CC(Cl)CN(C)C GYXWNSDLDXGMGU-UHFFFAOYSA-N 0.000 description 1
- CIIGWOXXOUVEAD-UHFFFAOYSA-N 2-chloroethyl benzenesulfonate Chemical compound ClCCOS(=O)(=O)C1=CC=CC=C1 CIIGWOXXOUVEAD-UHFFFAOYSA-N 0.000 description 1
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- FICAQKBMCKEFDI-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole Chemical compound CC=1C=C(C)ON=1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- ANRMBFFXQKJEIS-UHFFFAOYSA-N 5-(bromomethyl)-3-phenyl-1,2-oxazole Chemical compound O1C(CBr)=CC(C=2C=CC=CC=2)=N1 ANRMBFFXQKJEIS-UHFFFAOYSA-N 0.000 description 1
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- 244000105624 Arachis hypogaea Species 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- UNABPRGGCSJBPG-UHFFFAOYSA-N [2-[2-(dimethylamino)ethoxy]phenyl]methanol Chemical compound CN(C)CCOC1=CC=CC=C1CO UNABPRGGCSJBPG-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- PFCUZDIEKKTHCH-UHFFFAOYSA-N acetonitrile oxide Chemical compound CC#N=O PFCUZDIEKKTHCH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000001152 anti-nicotinic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JSGUAGLVBYBGOV-UHFFFAOYSA-N benzene chlorobenzene toluene Chemical compound ClC1=CC=CC=C1.C1(=CC=CC=C1)C.C1=CC=CC=C1 JSGUAGLVBYBGOV-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- KQHLPMCNDYYZMB-UHFFFAOYSA-N chloromethylbenzene;hydrochloride Chemical compound Cl.ClCC1=CC=CC=C1 KQHLPMCNDYYZMB-UHFFFAOYSA-N 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- AIPRAPZUGUTQKX-UHFFFAOYSA-N diethoxyphosphorylmethylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1 AIPRAPZUGUTQKX-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- YYHIRPUVYUUCTJ-UHFFFAOYSA-N methyl 2-[2-(dimethylamino)ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCN(C)C YYHIRPUVYUUCTJ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- BLIJXOOIHRSQRB-PXYINDEMSA-N n-[(2s)-1-[3-(3-chloro-4-cyanophenyl)pyrazol-1-yl]propan-2-yl]-5-(1-hydroxyethyl)-1h-pyrazole-3-carboxamide Chemical compound C([C@H](C)NC(=O)C=1NN=C(C=1)C(C)O)N(N=1)C=CC=1C1=CC=C(C#N)C(Cl)=C1 BLIJXOOIHRSQRB-PXYINDEMSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- BYMVZHORNHZYPQ-UHFFFAOYSA-N sodium;diethyl phosphite Chemical compound [Na+].CCOP([O-])OCC BYMVZHORNHZYPQ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- FHADSKGDQLZUIT-UHFFFAOYSA-N stilbene hydrochloride Chemical compound Cl.C1(=CC=CC=C1)C=CC1=CC=CC=C1 FHADSKGDQLZUIT-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
- C07C39/20—Hydroxy-styrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Illuminated Signs And Luminous Advertising (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1939809A DE1939809B2 (de) | 1969-08-05 | 1969-08-05 | ß-Aryl-2-aminoalkoxy-styrole und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL35047A0 IL35047A0 (en) | 1970-10-30 |
| IL35047A true IL35047A (en) | 1973-05-31 |
Family
ID=5741970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL35047A IL35047A (en) | 1969-08-05 | 1970-08-04 | In -rile and the troiryl-2-amino-alkoxy citrons and their preparation |
Country Status (25)
| Country | Link |
|---|---|
| JP (6) | JPS4941433B1 (no) |
| KR (1) | KR780000113B1 (no) |
| AT (5) | AT301565B (no) |
| BE (1) | BE754405A (no) |
| BG (6) | BG18600A3 (no) |
| CH (6) | CH548982A (no) |
| CS (6) | CS170537B2 (no) |
| DE (1) | DE1939809B2 (no) |
| DK (1) | DK139717B (no) |
| ES (6) | ES382428A1 (no) |
| FI (1) | FI54912C (no) |
| FR (1) | FR2068463B1 (no) |
| GB (1) | GB1307436A (no) |
| HU (1) | HU163185B (no) |
| IE (1) | IE34634B1 (no) |
| IL (1) | IL35047A (no) |
| NL (1) | NL7011590A (no) |
| NO (1) | NO135243C (no) |
| PH (1) | PH9520A (no) |
| PL (2) | PL78370B1 (no) |
| RO (5) | RO57793A (no) |
| SE (1) | SE382211B (no) |
| SU (4) | SU432712A3 (no) |
| YU (2) | YU198170A (no) |
| ZA (1) | ZA705411B (no) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50139537A (no) * | 1974-04-25 | 1975-11-07 | ||
| US4220603A (en) * | 1977-10-07 | 1980-09-02 | Mitsubishi Chemical Industries, Limited | Pharmaceutically active (omega-aminoalkoxy)bibenzyls |
| JPS6045632B2 (ja) * | 1978-03-09 | 1985-10-11 | 三菱化学株式会社 | ω−アミノアルコキシスチルベン類及びその酸付加塩 |
| DE2818765A1 (de) | 1978-04-28 | 1979-11-08 | Basf Ag | Aminoderivate des 2-methyl-5-(2-hydroxystyrol)-1,3,4-thiadiazols |
| DE2818998A1 (de) * | 1978-04-29 | 1979-11-15 | Basf Ag | 3-alkyl-5-(2-hydroxy-styryl)-isoxazole und verfahren zu ihrer herstellung |
| DE2818999A1 (de) * | 1978-04-29 | 1979-11-15 | Basf Ag | Aminoderivate von 3-alkyl-5-(2- hydroxystyryl)-isoxazolen |
| JPS5629548A (en) * | 1979-08-16 | 1981-03-24 | Mitsubishi Chem Ind Ltd | Omega-aminoalkoxystilbenes and their acid addition salts |
| DE2943406A1 (de) | 1979-10-26 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Aminoderivate des 2-methyl-5-(2-hydroxystyryl)-1,3,4-thiadiazols |
| DE2943405A1 (de) * | 1979-10-26 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Neue aminoderivate des 5-(2-hydroxystyryl)-isoxazols |
| DE3006809A1 (de) * | 1980-02-23 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | 2-((3-amino-2-hydroxy-propoxy)-styryl)-isoxazole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| JPS5874379U (ja) * | 1981-11-16 | 1983-05-19 | 富士通株式会社 | 電子装置 |
| NO174506B (no) * | 1984-10-30 | 1994-02-07 | Usv Pharma Corp | Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser |
| MX2013014588A (es) | 2011-06-10 | 2014-01-24 | Procter & Gamble | Estructura absorbente para articulos absorbentes. |
| CN105816277A (zh) | 2011-06-10 | 2016-08-03 | 宝洁公司 | 一次性尿布 |
| RU2013156991A (ru) | 2011-06-10 | 2015-07-20 | Дзе Проктер Энд Гэмбл Компани | Абсорбирующая сердцевина для одноразовых абсорбирующих изделий |
| EP2740449B1 (en) | 2012-12-10 | 2019-01-23 | The Procter & Gamble Company | Absorbent article with high absorbent material content |
| ES2655690T3 (es) | 2013-06-14 | 2018-02-21 | The Procter & Gamble Company | Artículo absorbente y canales de formación de núcleo absorbente cuando están húmedos |
| US9987176B2 (en) | 2013-08-27 | 2018-06-05 | The Procter & Gamble Company | Absorbent articles with channels |
| EP3351225B1 (en) | 2013-09-19 | 2021-12-29 | The Procter & Gamble Company | Absorbent cores having material free areas |
| PL2886092T3 (pl) | 2013-12-19 | 2017-03-31 | The Procter And Gamble Company | Wkłady chłonne z obszarami tworzącymi kanały i zgrzewami osłony c |
-
0
- BE BE754405D patent/BE754405A/xx unknown
-
1969
- 1969-08-05 DE DE1939809A patent/DE1939809B2/de active Granted
-
1970
- 1970-07-21 FI FI2035/70A patent/FI54912C/fi active
- 1970-07-22 RO RO65938A patent/RO57793A/ro unknown
- 1970-07-22 RO RO65491A patent/RO58861A2/ro unknown
- 1970-07-22 BG BG017594A patent/BG18600A3/xx unknown
- 1970-07-22 BG BG015253A patent/BG18599A3/xx unknown
- 1970-07-22 BG BG017596A patent/BG17950A3/xx unknown
- 1970-07-22 RO RO65939A patent/RO57794A/ro unknown
- 1970-07-22 BG BG017595A patent/BG20095A3/xx unknown
- 1970-07-22 BG BG017598A patent/BG17952A3/xx unknown
- 1970-07-22 RO RO64019A patent/RO57548A/ro unknown
- 1970-07-22 RO RO65937A patent/RO58837A/ro unknown
- 1970-07-22 BG BG017597A patent/BG17951A3/xx unknown
- 1970-07-28 SU SU1701181A patent/SU432712A3/ru active
- 1970-07-28 SU SU1700804A patent/SU439965A3/ru active
- 1970-07-28 SU SU1701190A patent/SU450398A3/ru active
- 1970-07-28 SU SU1701179A patent/SU428597A3/ru active
- 1970-07-30 KR KR7001068A patent/KR780000113B1/ko active
- 1970-07-31 CS CS3513*[A patent/CS170537B2/cs unknown
- 1970-07-31 CS CS5391A patent/CS170533B2/cs unknown
- 1970-07-31 CS CS3511*[A patent/CS170535B2/cs unknown
- 1970-07-31 CS CS3510*[A patent/CS170534B2/cs unknown
- 1970-07-31 CS CS3514*[A patent/CS170538B2/cs unknown
- 1970-07-31 CS CS3512*[A patent/CS170536B2/cs unknown
- 1970-08-03 JP JP45067958A patent/JPS4941433B1/ja active Pending
- 1970-08-03 HU HUTO819A patent/HU163185B/hu unknown
- 1970-08-04 ES ES382428A patent/ES382428A1/es not_active Expired
- 1970-08-04 CH CH148173A patent/CH548982A/xx not_active IP Right Cessation
- 1970-08-04 ES ES382429A patent/ES382429A1/es not_active Expired
- 1970-08-04 CH CH148273A patent/CH548983A/xx not_active IP Right Cessation
- 1970-08-04 YU YU01981/70A patent/YU198170A/xx unknown
- 1970-08-04 DK DK401270AA patent/DK139717B/da unknown
- 1970-08-04 GB GB3766370A patent/GB1307436A/en not_active Expired
- 1970-08-04 CH CH147873A patent/CH548981A/xx not_active IP Right Cessation
- 1970-08-04 CH CH148073A patent/CH548368A/xx not_active IP Right Cessation
- 1970-08-04 PH PH11713*UA patent/PH9520A/en unknown
- 1970-08-04 PL PL1970142516A patent/PL78370B1/pl unknown
- 1970-08-04 ES ES382427A patent/ES382427A1/es not_active Expired
- 1970-08-04 IL IL35047A patent/IL35047A/en unknown
- 1970-08-04 IE IE998/70A patent/IE34634B1/xx unknown
- 1970-08-04 ES ES382430A patent/ES382430A1/es not_active Expired
- 1970-08-04 CH CH147973A patent/CH548367A/fr not_active IP Right Cessation
- 1970-08-04 PL PL1970175377A patent/PL93130B1/pl unknown
- 1970-08-04 NO NO3005/70A patent/NO135243C/no unknown
- 1970-08-04 CH CH1172670A patent/CH548366A/xx not_active IP Right Cessation
- 1970-08-04 ES ES382425A patent/ES382425A1/es not_active Expired
- 1970-08-04 ES ES382426A patent/ES382426A1/es not_active Expired
- 1970-08-05 FR FR7028941A patent/FR2068463B1/fr not_active Expired
- 1970-08-05 AT AT713970A patent/AT301565B/de not_active IP Right Cessation
- 1970-08-05 ZA ZA705411A patent/ZA705411B/xx unknown
- 1970-08-05 SE SE7010773A patent/SE382211B/xx unknown
- 1970-08-05 AT AT943371A patent/AT302346B/de not_active IP Right Cessation
- 1970-08-05 AT AT943271A patent/AT303055B/de not_active IP Right Cessation
- 1970-08-05 NL NL7011590A patent/NL7011590A/xx not_active Application Discontinuation
- 1970-08-05 AT AT943171A patent/AT302345B/de not_active IP Right Cessation
- 1970-08-05 AT AT943071A patent/AT302344B/de not_active IP Right Cessation
-
1973
- 1973-11-29 JP JP48133940A patent/JPS5113149B1/ja active Pending
- 1973-11-29 JP JP48133939A patent/JPS5113148B1/ja active Pending
- 1973-11-29 JP JP48133937A patent/JPS5113146B1/ja active Pending
- 1973-11-29 JP JP48133941A patent/JPS5113150B1/ja active Pending
- 1973-11-29 JP JP48133938A patent/JPS5113147B1/ja active Pending
-
1978
- 1978-02-17 YU YU00374/78A patent/YU37478A/xx unknown
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