DD283389A5 - Verfahren zur herstellung neuer hydrierter 1-benzooxacycloalkylpyridincarbonsaeureverbindungen - Google Patents

Verfahren zur herstellung neuer hydrierter 1-benzooxacycloalkylpyridincarbonsaeureverbindungen Download PDF

Info

Publication number: DD283389A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; salt; compound; hydrogen; hydroxy
Prior art date: 1987-12-23

Application number

DD88323598A

Other languages

German (de)

English (en)

Inventor

Wolfgang Froestl

Original Assignee

��`��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-12-23

Filing date

1988-12-21

Publication date

1990-10-10

1988-12-21 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1990-10-10 Publication of DD283389A5 publication Critical patent/DD283389A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 127
239000002253 acid Substances 0.000 title claims abstract description 33
238000004519 manufacturing process Methods 0.000 title claims abstract description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title description 3
229910052799 carbon Inorganic materials 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 101
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 64
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 59
239000001257 hydrogen Substances 0.000 claims abstract description 48
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
238000000034 method Methods 0.000 claims abstract description 46
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 35
125000000217 alkyl group Chemical group 0.000 claims abstract description 34
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
238000002360 preparation method Methods 0.000 claims abstract description 28
125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
150000002431 hydrogen Chemical class 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 22
150000002367 halogens Chemical class 0.000 claims abstract description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
125000003277 amino group Chemical group 0.000 claims abstract description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 11
125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
125000001118 alkylidene group Chemical group 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
-1 hydroxy, protected amino Chemical group 0.000 claims description 117
239000000203 mixture Substances 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
150000001450 anions Chemical class 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
239000005977 Ethylene Substances 0.000 claims description 5
241000534944 Thia Species 0.000 claims description 5
125000005042 acyloxymethyl group Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
QMDFHZOGAYONLN-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-3-carboxylic acid Chemical compound OC(=O)C1CNC=CC1 QMDFHZOGAYONLN-UHFFFAOYSA-N 0.000 claims 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 22
230000001777 nootropic effect Effects 0.000 abstract description 8
239000008177 pharmaceutical agent Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
150000003254 radicals Chemical class 0.000 description 25
239000000243 solution Substances 0.000 description 25
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000002585 base Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000007858 starting material Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000011282 treatment Methods 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
150000003973 alkyl amines Chemical class 0.000 description 13
229910021529 ammonia Inorganic materials 0.000 description 11
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
229910052500 inorganic mineral Inorganic materials 0.000 description 10
239000011707 mineral Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000003797 solvolysis reaction Methods 0.000 description 9
239000003826 tablet Substances 0.000 description 9
239000000454 talc Substances 0.000 description 9
229910052623 talc Inorganic materials 0.000 description 9
235000012222 talc Nutrition 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
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 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229920002472 Starch Polymers 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
239000002775 capsule Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
150000004820 halides Chemical class 0.000 description 8
239000008101 lactose Substances 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
239000000825 pharmaceutical preparation Substances 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
238000001816 cooling Methods 0.000 description 7
229920000159 gelatin Polymers 0.000 description 7
235000019322 gelatine Nutrition 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
108010010803 Gelatin Proteins 0.000 description 5
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 5
241001465754 Metazoa Species 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
230000002490 cerebral effect Effects 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
229940014259 gelatin Drugs 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000008107 starch Substances 0.000 description 5
208000026139 Memory disease Diseases 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
125000004849 alkoxymethyl group Chemical group 0.000 description 4
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000000576 coating method Methods 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
239000012024 dehydrating agents‎ Substances 0.000 description 4
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
239000008298 dragée Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
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150000007522 mineralic acids Chemical class 0.000 description 4
239000002664 nootropic agent Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
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239000012071 phase 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
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
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LKFPDMHNTMAFGQ-UHFFFAOYSA-N 2-(2,2-dimethyl-3,4-dihydrochromen-3-yl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1C(C)(C)OC2=CC=CC=C2C1 LKFPDMHNTMAFGQ-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
UYAUSAWYPNTYON-UHFFFAOYSA-N methyl 3-[2-(2,2-dimethyl-3,4-dihydrochromen-3-yl)ethyl-(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound C1=CC=C2OC(C)(C)C(CCN(CCC(=O)OC)CCC(=O)OC)CC2=C1 UYAUSAWYPNTYON-UHFFFAOYSA-N 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
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239000001267 polyvinylpyrrolidone Substances 0.000 description 3
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239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
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239000003381 stabilizer Substances 0.000 description 3
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208000024891 symptom Diseases 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 3
125000004953 trihalomethyl group Chemical group 0.000 description 3
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
BRPWFEMSWSQEEN-UHFFFAOYSA-N 2-(2,2-dimethyl-3,4-dihydrochromen-3-yl)ethanamine Chemical compound C1=CC=C2CC(CCN)C(C)(C)OC2=C1 BRPWFEMSWSQEEN-UHFFFAOYSA-N 0.000 description 2
ZSTGWQNDRHYKEP-UHFFFAOYSA-N 2-(2,2-dimethyl-3,4-dihydrochromen-3-yl)ethanol Chemical compound C1=CC=C2CC(CCO)C(C)(C)OC2=C1 ZSTGWQNDRHYKEP-UHFFFAOYSA-N 0.000 description 2
HAVSXSICHYKROB-UHFFFAOYSA-N 3-(2-azidoethyl)-2,2-dimethyl-3,4-dihydrochromene Chemical compound C1=CC=C2CC(CCN=[N+]=[N-])C(C)(C)OC2=C1 HAVSXSICHYKROB-UHFFFAOYSA-N 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
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244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
108700039855 mouse a Proteins 0.000 description 1
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical group CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical class [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Psychiatry (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hospice & Palliative Care (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD88323598A 1987-12-23 1988-12-21 Verfahren zur herstellung neuer hydrierter 1-benzooxacycloalkylpyridincarbonsaeureverbindungen DD283389A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH500887		1987-12-23

Publications (1)

Publication Number	Publication Date
DD283389A5 true DD283389A5 (de)	1990-10-10

Family

ID=4286355

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88323598A DD283389A5 (de)	1987-12-23	1988-12-21	Verfahren zur herstellung neuer hydrierter 1-benzooxacycloalkylpyridincarbonsaeureverbindungen

Country Status (11)

Country	Link
EP (1)	EP0322361A3 (da)
JP (1)	JPH01203379A (da)
KR (1)	KR890009915A (da)
AU (1)	AU2730888A (da)
DD (1)	DD283389A5 (da)
DK (1)	DK718488A (da)
FI (1)	FI885903A7 (da)
IL (1)	IL88727A0 (da)
NO (1)	NO885711L (da)
PT (1)	PT89291A (da)
ZA (1)	ZA889580B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3726261A1 (de) *	1986-12-23	1988-07-07	Merck Patent Gmbh	Chromanderivate
FR2642069B1 (fr) *	1989-01-20	1991-04-12	Rhone Poulenc Sante	Nouveaux derives du benzopyranne, leur preparation et les compositions pharmaceutiques qui les contiennent
WO1991017156A1 (en) *	1990-05-10	1991-11-14	Pfizer Inc	Neuroprotective indolone and related derivatives
US5436255A (en) *	1992-07-23	1995-07-25	Pfizer Inc.	Method of treating diseases susceptable to treatment by blocking NMDA-receptors
DK0666854T3 (da) *	1992-10-30	1997-04-28	Pfizer	Neurobeskyttende 3,4-dihydro-2(1H)-quinolon forbindelser
US5498610A (en) *	1992-11-06	1996-03-12	Pfizer Inc.	Neuroprotective indolone and related derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE63744T1 (de) *	1985-09-03	1991-06-15	Ciba Geigy Ag	3-amino-dihydro-(1>-benzopyrane und benzothiopyrane.
DE3771280D1 (de) *	1986-06-26	1991-08-14	Ciba Geigy Ag	Hydrierte 1-benzooxacycloalkyl-pyridincarbonsaeureverbindungen.

1988
- 1988-12-14 EP EP88810860A patent/EP0322361A3/de not_active Withdrawn
- 1988-12-19 IL IL88727A patent/IL88727A0/xx unknown
- 1988-12-20 AU AU27308/88A patent/AU2730888A/en not_active Abandoned
- 1988-12-21 DD DD88323598A patent/DD283389A5/de not_active IP Right Cessation
- 1988-12-21 PT PT89291A patent/PT89291A/pt not_active Application Discontinuation
- 1988-12-21 FI FI885903A patent/FI885903A7/fi not_active Application Discontinuation
- 1988-12-22 KR KR1019880017206A patent/KR890009915A/ko not_active Withdrawn
- 1988-12-22 DK DK718488A patent/DK718488A/da not_active Application Discontinuation
- 1988-12-22 ZA ZA889580A patent/ZA889580B/xx unknown
- 1988-12-22 JP JP63322224A patent/JPH01203379A/ja active Pending
- 1988-12-22 NO NO88885711A patent/NO885711L/no unknown

Also Published As

Publication number	Publication date
KR890009915A (ko)	1989-08-04
EP0322361A3 (de)	1990-01-24
NO885711D0 (no)	1988-12-22
PT89291A (pt)	1989-12-29
FI885903A7 (fi)	1989-06-24
NO885711L (no)	1989-06-26
JPH01203379A (ja)	1989-08-16
ZA889580B (en)	1989-08-30
EP0322361A2 (de)	1989-06-28
DK718488D0 (da)	1988-12-22
AU2730888A (en)	1989-06-29
DK718488A (da)	1989-06-24
IL88727A0 (en)	1989-07-31

Legal Events

Date	Code	Title	Description
1995-06-22	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
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DE69716062T2 (de)	2003-06-18	Benzofuran-derivate und deren verwendung
DE2758937A1 (de)	1978-08-17	Verfahren zur herstellung von, gegebenenfalls an ihrer hydroxygruppe durch eine trialkylsilylgruppe geschuetzten, 4-hydroxypyrrolidin-2-on-1- ylalkylcarbonsaeureestern sowie n-aethyl- 2-(4'-hydroxypyrrolidin-2'-on-1'-yl) -acetamid und dieses enthaltende arzneimittel
DE2110445A1 (de)	1971-11-04	1-Benzyl-tetrahydro-2-(1H)pyrimidone
EP0136658A2 (de)	1985-04-10	1-Benzyl-aminoalkyl-pyrrolidinone und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel
EP0252005B1 (de)	1991-07-10	Hydrierte 1-Benzooxacycloalkyl-pyridincarbonsäureverbindungen
DE60006054T2 (de)	2004-07-22	Herstellungsverfahren für Pyridinderivate
DE3149010A1 (de)	1983-07-07	(+)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3- diazacyclopent-2-en, dessen herstellung und seine verwendung in pharamazeutischen praeparaten
EP0250361B1 (de)	1993-12-08	Disubstituierte Piperazine
DD283389A5 (de)	1990-10-10	Verfahren zur herstellung neuer hydrierter 1-benzooxacycloalkylpyridincarbonsaeureverbindungen
EP0192255B1 (de)	1990-08-08	Bi-2H-pyrroli(di)ndione
DE4316117C2 (de)	2002-06-27	Cycloheptimidazol-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende, therapeutische Mittel
EP0266308B1 (de)	1991-07-24	Indolo-pyrazino-benzodiazepin-Derivate
EP0389425B1 (de)	1995-04-26	Neue Benzothiopyranylamine
EP0213080B1 (de)	1992-05-20	Hydropyridin-Derivate
EP0128120A2 (de)	1984-12-12	Trisubstituierte Oxazolidinone
EP0229011A1 (de)	1987-07-15	Trisubstituierte Triazole
EP0248414A2 (de)	1987-12-09	Aralkylimidazolderivate
DE2653251A1 (de)	1977-06-08	Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendung
EP0252876A1 (de)	1988-01-13	Hydrierte 1-Phenoxyalkylpyridin-3-carbonsäureverbindungen
EP0187619A2 (de)	1986-07-16	1,3-disubstituierte Tetrahydropyridine
AT375079B (de)	1984-06-25	Verfahren zur herstellung von neuen trans-2,3,4,4a ,5,9b-hexahydro-1h-pyrido(4,3-b)indolen und ihren pharmazeutisch annehmbaren salzen
EP0239533B1 (de)	1992-09-16	Pyridin-Derivate
DD259189A5 (de)	1988-08-17	Verfahren zur herstellung neuer hydropyridin-derivate
EP0395580A2 (de)	1990-10-31	Verfahren zur Herstellung polycyclischer Verbindungen