NO885711L - Hydrerte 1-benzooksacykloalkylpyridinkarboksylsyreforbindelser. - Google Patents

Hydrerte 1-benzooksacykloalkylpyridinkarboksylsyreforbindelser.

Info

Publication number: NO885711L
Authority: NO; Norway
Prior art keywords: stands; formula; salt; compound; alkyl
Prior art date: 1987-12-23

Application number

NO88885711A

Other languages

English (en)

Norwegian (no)

Other versions

NO885711D0 (no

Inventor

Wolfgang Froestl

Original Assignee

Ciba Geigy Ag

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

1988-12-22

Publication date

1989-06-26

1988-12-22 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1988-12-22 Publication of NO885711D0 publication Critical patent/NO885711D0/no

1989-06-26 Publication of NO885711L publication Critical patent/NO885711L/no

Links

-1 CARBOXYLIC ACID COMPOUNDS Chemical class 0.000 title claims abstract description 135
150000001875 compounds Chemical class 0.000 claims abstract description 157
150000003839 salts Chemical class 0.000 claims abstract description 122
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 87
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 66
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
238000000034 method Methods 0.000 claims abstract description 58
239000001257 hydrogen Substances 0.000 claims abstract description 57
239000002253 acid Substances 0.000 claims abstract description 42
125000000217 alkyl group Chemical group 0.000 claims abstract description 35
229910052736 halogen Inorganic materials 0.000 claims abstract description 33
150000002367 halogens Chemical class 0.000 claims abstract description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
238000002360 preparation method Methods 0.000 claims abstract description 29
150000002431 hydrogen Chemical class 0.000 claims abstract description 26
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
230000008569 process Effects 0.000 claims abstract description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 18
125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
125000003277 amino group Chemical group 0.000 claims abstract description 11
125000002947 alkylene group Chemical group 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 39
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 22
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
239000005977 Ethylene Substances 0.000 claims description 8
125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 7
241000534944 Thia Species 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
125000001118 alkylidene group Chemical group 0.000 claims description 4
JKYGXBNSPQKSQL-UHFFFAOYSA-N methyl 3-[2-(6-fluoro-2,2-dimethyl-3,4-dihydrochromen-3-yl)ethylamino]propanoate Chemical compound FC1=CC=C2OC(C)(C)C(CCNCCC(=O)OC)CC2=C1 JKYGXBNSPQKSQL-UHFFFAOYSA-N 0.000 claims description 2
125000003431 oxalo group Chemical group 0.000 claims description 2
IIMAGUHGXLWHRE-UHFFFAOYSA-N methyl 1-[2-(2,2-dimethyl-3,4-dihydrochromen-3-yl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1CCC1C(C)(C)OC2=CC=CC=C2C1 IIMAGUHGXLWHRE-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
229910052799 carbon Inorganic materials 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 2
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
235000002639 sodium chloride Nutrition 0.000 description 93
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
239000000243 solution Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
239000013543 active substance Substances 0.000 description 21
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 18
235000019198 oils Nutrition 0.000 description 18
239000007858 starting material Substances 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
238000011282 treatment Methods 0.000 description 16
150000007513 acids Chemical class 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
229910052500 inorganic mineral Inorganic materials 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
235000010755 mineral Nutrition 0.000 description 13
239000011707 mineral Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 12
235000011121 sodium hydroxide Nutrition 0.000 description 12
239000000725 suspension Substances 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
238000001816 cooling Methods 0.000 description 11
239000000825 pharmaceutical preparation Substances 0.000 description 11
229910052740 iodine Inorganic materials 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
238000003797 solvolysis reaction Methods 0.000 description 9
239000003826 tablet Substances 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 8
238000003756 stirring Methods 0.000 description 8
229920002472 Starch Polymers 0.000 description 7
125000004849 alkoxymethyl group Chemical group 0.000 description 7
150000003973 alkyl amines Chemical class 0.000 description 7
239000002775 capsule Substances 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
150000007522 mineralic acids Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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 6
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
125000005115 alkyl carbamoyl group Chemical group 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
239000012071 phase Substances 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000009467 reduction Effects 0.000 description 6
239000000454 talc Substances 0.000 description 6
229910052623 talc Inorganic materials 0.000 description 6
235000012222 talc Nutrition 0.000 description 6
125000004953 trihalomethyl group Chemical group 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
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 5
125000004423 acyloxy group Chemical group 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
229940014259 gelatin Drugs 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
230000001777 nootropic effect Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000008107 starch Substances 0.000 description 5
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
125000001931 aliphatic group Chemical group 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
230000002490 cerebral effect Effects 0.000 description 4
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
239000012024 dehydrating agents‎ Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000155 melt Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002664 nootropic agent Substances 0.000 description 4
XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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
239000011701 zinc Substances 0.000 description 4
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 3
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
GXQBWNJLRLCGFM-UHFFFAOYSA-N 2-(6-fluoro-2,2-dimethyl-3,4-dihydrochromen-3-yl)ethanamine Chemical compound C1=C(F)C=C2CC(CCN)C(C)(C)OC2=C1 GXQBWNJLRLCGFM-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
208000026139 Memory disease Diseases 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
150000008107 benzenesulfonic acids Chemical class 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
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
239000008055 phosphate buffer solution Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 3
DFYAZQSHPYCKOC-UHFFFAOYSA-N 2-(6-fluoro-2,2-dimethyl-3,4-dihydrochromen-3-yl)ethanol Chemical compound C1=C(F)C=C2CC(CCO)C(C)(C)OC2=C1 DFYAZQSHPYCKOC-UHFFFAOYSA-N 0.000 description 2
VAUSACOLHISCFT-UHFFFAOYSA-N 2-(6-fluoro-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=C(F)C=C2C1 VAUSACOLHISCFT-UHFFFAOYSA-N 0.000 description 2
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 2
RDWRORDBKMZOLE-UHFFFAOYSA-N 6-fluoro-2,2-dimethyl-4h-chromen-3-one Chemical compound C1=C(F)C=C2CC(=O)C(C)(C)OC2=C1 RDWRORDBKMZOLE-UHFFFAOYSA-N 0.000 description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
UTXVCHVLDOLVPC-UHFFFAOYSA-N ethyl 3-methylbut-2-enoate Chemical compound CCOC(=O)C=C(C)C UTXVCHVLDOLVPC-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000004678 hydrides 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
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229940006461 iodide ion Drugs 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000004658 ketimines Chemical class 0.000 description 1
OCPSGEDKHQWXKW-UHFFFAOYSA-N lithium tritylazanide Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)[NH-].[Li+] OCPSGEDKHQWXKW-UHFFFAOYSA-N 0.000 description 1
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000006883 memory enhancing effect Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
DOXOETUWVNVADB-UHFFFAOYSA-N methyl 1,2,3,6-tetrahydropyridine-5-carboxylate;hydrobromide Chemical compound Br.COC(=O)C1=CCCNC1 DOXOETUWVNVADB-UHFFFAOYSA-N 0.000 description 1
XWOLCUJQBQDEQU-UHFFFAOYSA-N methyl 1-[2-(2,2-dimethyl-3,4-dihydrochromen-3-yl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate;hydrochloride Chemical compound Cl.C1C(C(=O)OC)=CCCN1CCC1C(C)(C)OC2=CC=CC=C2C1 XWOLCUJQBQDEQU-UHFFFAOYSA-N 0.000 description 1
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 1
OQCQRKFKZURTGM-UHFFFAOYSA-N methyl 3-[2-(6-fluoro-2,2-dimethyl-3,4-dihydrochromen-3-yl)ethylamino]propanoate;hydrochloride Chemical compound Cl.FC1=CC=C2OC(C)(C)C(CCNCCC(=O)OC)CC2=C1 OQCQRKFKZURTGM-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
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
125000005489 p-toluenesulfonic acid group Chemical class 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
239000008177 pharmaceutical agent Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 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
239000012286 potassium permanganate Substances 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
230000000069 prophylactic effect Effects 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
238000006798 ring closing metathesis reaction Methods 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
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 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
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
241000894007 species Species 0.000 description 1
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical class [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
230000019635 sulfation Effects 0.000 description 1
238000005670 sulfation reaction Methods 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
230000007704 transition Effects 0.000 description 1
229910052723 transition metal Inorganic materials 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
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000007966 viscous suspension Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229940100445 wheat starch Drugs 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)

NO88885711A 1987-12-23 1988-12-22 Hydrerte 1-benzooksacykloalkylpyridinkarboksylsyreforbindelser. NO885711L (no)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
NO885711D0 NO885711D0 (no)	1988-12-22
NO885711L true NO885711L (no)	1989-06-26

Family

ID=4286355

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO88885711A NO885711L (no)	1987-12-23	1988-12-22	Hydrerte 1-benzooksacykloalkylpyridinkarboksylsyreforbindelser.

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
DD283389A5 (de)	1990-10-10
FI885903A7 (fi)	1989-06-24
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

Publication	Publication Date	Title
CZ280053B6 (cs)	1995-10-18	3-Substituovaný pyrrolidinový derivát, způsob jeho přípravy, meziprodukty tohoto způsobu, farmaceutický prostředek obsahující tento derivát
NO162818B (no)	1989-11-13	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 1,4-dihyropyridiner.
NO177140B (no)	1995-04-18	Analogifremgangsmåte for fremstilling av substituert pyridyl-dihydroksy-heptensyre og salter derav samt mellomprodukt til bruk i fremgangsmåten
NZ219241A (en)	1990-01-29	Pyridine derivatives and pharmaceutical compositions
AU617988B2 (en)	1991-12-12	Hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds
NO885711L (no)	1989-06-26	Hydrerte 1-benzooksacykloalkylpyridinkarboksylsyreforbindelser.
HU202508B (en)	1991-03-28	Process for producing new 1,4-disubstituted piperazine derivatives and pharmaceutical compositions containing them as active components
US3192230A (en)	1965-06-29	Process for producing 1, 3, 3-trisubstituted-4-(beta-haloethyl)-2-pyrrolidinone
EP0389425B1 (de)	1995-04-26	Neue Benzothiopyranylamine
CS221269B2 (en)	1983-04-29	Method of preparation of new 1,5-disubstituted 2-pyrrolidone compounds
US5112855A (en)	1992-05-12	Hydrogenated 1-benzooxacycloalkylpyridinecarboxylic acid compounds and compositions
FI85693B (fi)	1992-02-14	Foerfarande foer framstaellning av nya hydropyridinderivat.
US4179460A (en)	1979-12-18	Derivatives of R,S-[X2-(2-hydroxyethylamino)-1-phenyl]-ethylamine, and process
NO178496B (no)	1996-01-02	Kinolin-2-yl-metoksybenzylhydroksyurea
DK168741B1 (da)	1994-05-30	Phenyleddikesyrederivater, lægemiddel indeholdende et sådant derivat, anvendelse af et sådant derivat til fremstilling af et lægemiddel, fremgangsmåde til fremstilling af lægemidlet samt analogifremgangsmåde til fremstilling af phenyleddikesyrederivaterne
NO881899L (no)	1988-11-03	Nye 2-aminoalkyl-4-benzyl-1-(2h)-ftalazino-derivater.
US4078073A (en)	1978-03-07	N-tricyclic derivatives of azetidine
JPH11209344A (ja)	1999-08-03	含窒素複素環化合物
AU745808B2 (en)	2002-04-11	New benzocyclobutane compounds, a process for their preparation and pharmaceutical compositions containing them
NO874724L (no)	1989-05-16	Fremgangsmaate for fremstilling av hydrerte 1-fenoksyalkylpyridin-3-karboksylsyreforbindelser.
JPS638373A (ja)	1988-01-14	水素化１−フェノキシアルキルピリジン−３−カルボン酸化合物
NO760216L (da)	1976-07-27
NO860007L (no)	1986-07-04	Fremgangsmaate til fremstilling av nye trisubstituerte azacykloalkaner, resp. azacykloalkener.
NZ222517A (en)	1991-04-26	1-benzooxacycloalkylpyridine carboxylic acid derivatives, intermediates, and pharmaceutical compositions
NO842221L (no)	1984-12-03	Fremgangsmaate til fremstilling av trisubstituerte oksazolidinoner