SE444933B - Lekemedel for behandling av sjukdomar i centrala nervsystemet, vilka innehaller vissa cyklohexylkarboxylsyraderivat som aktiv bestandsdel - Google Patents

Lekemedel for behandling av sjukdomar i centrala nervsystemet, vilka innehaller vissa cyklohexylkarboxylsyraderivat som aktiv bestandsdel

Info

Publication number: SE444933B
Authority: SE; Sweden
Prior art keywords: acid; cyclohexyl; group; mixture; yield
Prior art date: 1978-04-27

Application number

SE7903687A

Other languages

English (en)

Swedish (sv)

Other versions

SE7903687L (sv

Inventor

C Pigerol

J-C Vernieres

P Eymard

J Simiand

M Broll

J-Y Lacolle

Original Assignee

Sanofi Sa

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.)

1978-04-27

Filing date

1979-04-26

Publication date

1986-05-20

1979-04-26 Application filed by Sanofi Sa filed Critical Sanofi Sa

1979-10-28 Publication of SE7903687L publication Critical patent/SE7903687L/xx

1986-05-20 Publication of SE444933B publication Critical patent/SE444933B/sv

Links

-1 CYCLOHEXYL CARBOXYL Chemical class 0.000 title claims description 48
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 5
239000004480 active ingredient Substances 0.000 title claims description 4
210000003169 central nervous system Anatomy 0.000 title claims description 4
239000002253 acid Substances 0.000 title description 63
201000010099 disease Diseases 0.000 title 2
150000001875 compounds Chemical class 0.000 claims description 49
239000011734 sodium Substances 0.000 claims description 15
229910052708 sodium Inorganic materials 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229920002554 vinyl polymer Chemical group 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
150000001340 alkali metals Chemical group 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims 1
125000004849 alkoxymethyl group Chemical group 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
125000005997 bromomethyl group Chemical group 0.000 claims 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 47
239000000203 mixture Substances 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
238000000034 method Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
150000007513 acids Chemical class 0.000 description 21
238000002360 preparation method Methods 0.000 description 19
150000003254 radicals Chemical class 0.000 description 18
239000007788 liquid Substances 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000013078 crystal Substances 0.000 description 16
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
239000000047 product Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
239000002585 base Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
241001465754 Metazoa Species 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
241000699670 Mus sp. Species 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
150000002367 halogens Chemical class 0.000 description 8
238000010992 reflux Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000005457 ice water Substances 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000035939 shock Effects 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
150000002576 ketones Chemical group 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
GIYMIIVDJHJFDG-UHFFFAOYSA-N 1-(propan-2-yloxymethyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)OCC1(C(O)=O)CCCCC1 GIYMIIVDJHJFDG-UHFFFAOYSA-N 0.000 description 4
229910014033 C-OH Inorganic materials 0.000 description 4
229910014570 C—OH Inorganic materials 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
150000002642 lithium compounds Chemical class 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
KIBHWMRCNKMKQJ-UHFFFAOYSA-N 1-benzylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1CC1(C(=O)O)CCCCC1 KIBHWMRCNKMKQJ-UHFFFAOYSA-N 0.000 description 3
SQZCJGGPRDQHHQ-UHFFFAOYSA-N 1-ethenylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C=C)CCCCC1 SQZCJGGPRDQHHQ-UHFFFAOYSA-N 0.000 description 3
125000006017 1-propenyl group Chemical group 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000009435 amidation Effects 0.000 description 3
238000007112 amidation reaction Methods 0.000 description 3
230000001773 anti-convulsant effect Effects 0.000 description 3
239000001961 anticonvulsive agent Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000006870 function Effects 0.000 description 3
125000002768 hydroxyalkyl group Chemical group 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
PNYKNBFZBIRUNG-UHFFFAOYSA-N 1-(2-methylpropyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CC1(C(O)=O)CCCCC1 PNYKNBFZBIRUNG-UHFFFAOYSA-N 0.000 description 2
ZOJNANYILVFQBD-UHFFFAOYSA-N 1-ethylcyclohexane-1-carboxamide Chemical compound CCC1(C(N)=O)CCCCC1 ZOJNANYILVFQBD-UHFFFAOYSA-N 0.000 description 2
QRRSHRVKVLSFQS-UHFFFAOYSA-N 1-ethylcyclohexane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCCCC1 QRRSHRVKVLSFQS-UHFFFAOYSA-N 0.000 description 2
ZPMWTYRADOECFN-UHFFFAOYSA-N 1-ethynylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C#C)CCCCC1 ZPMWTYRADOECFN-UHFFFAOYSA-N 0.000 description 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 2
NPRFVBVVQXZPOO-UHFFFAOYSA-N 1-tert-butylcyclohexane-1-carboxylic acid Chemical compound CC(C)(C)C1(C(O)=O)CCCCC1 NPRFVBVVQXZPOO-UHFFFAOYSA-N 0.000 description 2
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
102000008214 Glutamate decarboxylase Human genes 0.000 description 2
108091022930 Glutamate decarboxylase Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
244000166550 Strophanthus gratus Species 0.000 description 2
RNNABCNZZQTIJP-UHFFFAOYSA-N [1-(bromomethyl)cyclohexyl]methyl acetate Chemical compound CC(=O)OCC1(CBr)CCCCC1 RNNABCNZZQTIJP-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000005354 acylalkyl group Chemical group 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
230000000496 anti-anoxic effect Effects 0.000 description 2
229960003965 antiepileptics Drugs 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000000262 haloalkenyl group Chemical group 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
150000001261 hydroxy acids Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
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Classifications

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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/15—Saturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/35—Unsaturated compounds having unsaturation outside the rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/02—Saturated compounds containing hydroxy or O-metal groups
- C07C62/04—Saturated compounds containing hydroxy or O-metal groups with a six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/08—Saturated compounds containing ether groups, groups, groups, or groups
- C07C62/10—Saturated compounds containing ether groups, groups, groups, or groups with a six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/18—Saturated compounds containing keto groups
- C07C62/20—Saturated compounds containing keto groups with a saturated six-membered ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SE7903687A 1978-04-27 1979-04-26 Lekemedel for behandling av sjukdomar i centrala nervsystemet, vilka innehaller vissa cyklohexylkarboxylsyraderivat som aktiv bestandsdel SE444933B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1676278		1978-04-27

Publications (2)

Publication Number	Publication Date
SE7903687L SE7903687L (sv)	1979-10-28
SE444933B true SE444933B (sv)	1986-05-20

Family

ID=10083194

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SE7903687A SE444933B (sv)	1978-04-27	1979-04-26	Lekemedel for behandling av sjukdomar i centrala nervsystemet, vilka innehaller vissa cyklohexylkarboxylsyraderivat som aktiv bestandsdel
SE8304410A SE8304410L (sv)	1978-04-27	1983-08-15	Cyklohexylkarboxylsyraderivat och sett for deras framstellning

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SE8304410A SE8304410L (sv)	1978-04-27	1983-08-15	Cyklohexylkarboxylsyraderivat och sett for deras framstellning

Country Status (15)

Country	Link
US (1)	US4283420A (fr)
JP (1)	JPS6054285B2 (fr)
BE (1)	BE875882A (fr)
CA (1)	CA1150150A (fr)
CH (1)	CH641756A5 (fr)
DE (1)	DE2916588A1 (fr)
DK (1)	DK168079A (fr)
ES (1)	ES480041A1 (fr)
FR (1)	FR2432015A1 (fr)
GB (2)	GB2081714B (fr)
IT (1)	IT1202916B (fr)
NL (1)	NL7903352A (fr)
OA (1)	OA06248A (fr)
SE (2)	SE444933B (fr)
YU (1)	YU102579A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4530935A (en) *	1979-02-02	1985-07-23	The United States Of America As Represented By The Secretary Of Agriculture	Insect repellents
US4675342A (en) *	1979-02-02	1987-06-23	The United States Of America As Represented By The Secretary Of Agriculture	Cockroach repellents
US5068414A (en) *	1990-01-26	1991-11-26	Celgene Corporation	Hydroxyterephthalic acid
US5086054A (en) *	1990-07-31	1992-02-04	Sri International	Novel arylcycloalkanepolyalkylamines
EP1935867A1 (fr) *	2006-12-20	2008-06-25	F. Hoffmann-La Roche Ag	Procédé de préparation de l'acide 1-(2-éthyl-butyl)-cyclohexanecarboxylique
ES2460900T3 (es) *	2008-04-04	2014-05-14	F. Hoffmann-La Roche Ag	Nuevo procedimiento para la preparación de derivados de ácido ciclohexanocarboxílico mediante el correspondiente derivado ciclohexanocarboxamida
BRPI0909813B1 (pt) *	2008-04-04	2018-01-02	F. Hoffmann-La Roche Ag	"processos para preparação de derivados de ácido ciclo-hexanocarboxílico, e intermediário"
CN102015629A (zh) *	2008-05-08	2011-04-13	弗·哈夫曼-拉罗切有限公司	1-(2-乙基丁基)环己腈的合成方法
GB201416017D0 (en) *	2014-09-10	2014-10-22	New Royal Holloway & Bedford	An Anticonvulsant Compound

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL62140C (fr) *	1942-12-16
US2474796A (en) *	1946-01-31	1949-06-28	Wm S Merrell Co	Alkylaminoalkyl esters of alicyclyl-alicyclic carboxylic acids
US2757177A (en) *	1952-02-12	1956-07-31	Olin Mathieson	Basic derivatives of substituted cycloalkanecarboxylic acids and methods of preparing same
US2688025A (en) *	1952-02-12	1954-08-31	Olin Mathieson	Basic derivatives of substituted cycloalkanecarboxylic acids and methods of preparing same
DE1048575B (de) *	1957-04-27	1959-01-15	Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brüning, Frankfurt/M	Verfahren zur Herstellung von Cyclohexencarbonsäureamiden
FR1231163A (fr) *	1959-04-08	1960-09-27	Kodak Pathe	Nouveaux polyesters de grande masse moléculaire, procédé et intermédiaires pour leur fabrication et leurs applications industrielles
DE1301811B (de) *	1964-05-22	1969-08-28	E.I. Du Pont De Nemours And Company, Wilmington, Del. (V.St.A.)	Verfahren zur Herstellung von 4-Alkyl-1,4-dimethylcyclohexylaminen bzw. -cyclohexylmethylaminen bzw. von deren Salzen
BE735385A (fr) *	1968-07-04	1969-12-01
FR2059975A1 (en) *	1969-08-13	1971-06-11	Synthelabo	1-substd cyclohexane carboxylic acid hydrazides
US3841024A (en) *	1972-03-24	1974-10-15	Chiap Hua Comalco Ltd	Sliding window
GB1411786A (en) *	1972-04-18	1975-10-29	Wilkinson Sword Ltd	Substituted cyclohexanamides their preparation and use as cold receptor stimulants
IT1006572B (it) *	1972-04-18	1976-10-20	Wilkinson Sword Ltd	Composizioni ingeribili locali e altre aventi un effetto fisiologi co raffreddante sulla pelle e sul le membrane mucose del corpo

1979
- 1979-04-17 CH CH360679A patent/CH641756A5/fr not_active IP Right Cessation
- 1979-04-18 US US06/031,165 patent/US4283420A/en not_active Expired - Lifetime
- 1979-04-24 DE DE19792916588 patent/DE2916588A1/de not_active Withdrawn
- 1979-04-24 DK DK168079A patent/DK168079A/da active IP Right Grant
- 1979-04-24 FR FR7910384A patent/FR2432015A1/fr active Granted
- 1979-04-26 BE BE0/194860A patent/BE875882A/fr not_active IP Right Cessation
- 1979-04-26 SE SE7903687A patent/SE444933B/sv not_active IP Right Cessation
- 1979-04-26 GB GB8123729A patent/GB2081714B/en not_active Expired
- 1979-04-26 GB GB7914511A patent/GB2023002B/en not_active Expired
- 1979-04-26 CA CA000326456A patent/CA1150150A/fr not_active Expired
- 1979-04-27 JP JP54053305A patent/JPS6054285B2/ja not_active Expired
- 1979-04-27 ES ES480041A patent/ES480041A1/es not_active Expired
- 1979-04-27 OA OA56799A patent/OA06248A/fr unknown
- 1979-04-27 IT IT22191/79A patent/IT1202916B/it active
- 1979-04-27 YU YU01025/79A patent/YU102579A/xx unknown
- 1979-04-27 NL NL7903352A patent/NL7903352A/xx not_active Application Discontinuation
1983
- 1983-08-15 SE SE8304410A patent/SE8304410L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
NL7903352A (nl)	1979-10-30
BE875882A (fr)	1979-08-16
CH641756A5 (fr)	1984-03-15
YU102579A (en)	1983-12-31
DE2916588A1 (de)	1979-11-08
DK168079A (da)	1979-10-28
OA06248A (fr)	1981-06-30
GB2081714A (en)	1982-02-24
IT7922191A0 (it)	1979-04-27
GB2023002A (en)	1979-12-28
FR2432015B1 (fr)	1984-11-16
JPS554365A (en)	1980-01-12
GB2023002B (en)	1982-11-24
ES480041A1 (es)	1980-07-16
CA1150150A (fr)	1983-07-19
SE8304410D0 (sv)	1983-08-15
US4283420A (en)	1981-08-11
IT1202916B (it)	1989-02-15
SE8304410L (sv)	1983-08-15
SE7903687L (sv)	1979-10-28
GB2081714B (en)	1983-03-23
JPS6054285B2 (ja)	1985-11-29
FR2432015A1 (fr)	1980-02-22

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EP0257882B1 (fr)	1991-07-24	N-Phénylamides d'acides buténoiques à propriétés pharmaceutiques
DE3826439A1 (de)	1989-02-16	Sulfonamidothienylcarbonsaeureverbindungen
US2338220A (en)	1944-01-04	Process of making oxazolidinediones
DE69211994T2 (de)	1997-02-20	Lignan-analoge, ihre herstellung und hypolipidemische arzneimittel
EP0220573B1 (fr)	1991-12-11	Composés hétérocycliques
US3981868A (en)	1976-09-21	Derivatives of 9-oxo-13-trans-prostenoic acid amides
US4283420A (en)	1981-08-11	Pharmaceutically active cyclohexyl compounds and their preparation
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US3257420A (en)	1966-06-21	Carboxylic acids alpha-substituted by at least one cyclic radical
DE1620733A1 (de)	1970-09-03	Azetidinothiazolidinmethancarbonsaeureestern
Erhardt	1979	Curtius conversion of acids to amines under neutral conditions via an anthrylmethyl carbamate
US5135941A (en)	1992-08-04	LTB4 synthesis inhibitors
US3931286A (en)	1976-01-06	Novel benzoylphenylacetic acid derivatives
Baker et al.	1947	BIOTIN. IV. A SECOND SYNTHESIS OF 2-(δ-CARBOXYBUTYL)-THIOPHANE-3, 4-DICARBOXYLIC ACID
Blicke et al.	1952	Antispasmodics. IX. β-Diethylaminoethyl Esters of Substituted α-Aryl-β-hydroxypropionic Acids
DE2251556C3 (de)	1979-02-08	Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
US4520028A (en)	1985-05-28	α-Aminobutyric acid transaminase inhibitors
US4169953A (en)	1979-10-02	Tricyclo[4.3.1.12,5 ]undecane-1-carboxylic acid and derivatives thereof and a process for producing the same
CH619955A5 (fr)	1980-10-31
NZ208607A (en)	1986-08-08	Bicyclo(3.2.1)octane-3-carboxylic acid derivatives and therapeutic compositions
US5179123A (en)	1993-01-12	LTB4 synthesis inhibitors
Hanson et al.	1997	An expedient synthesis of (±)‐2‐amino‐3‐(3‐hydroxy‐5‐methylisoxazol‐4‐yl) propionic acid hydrobromide via a 3‐bromoisoxazole intermediate
Dvoretzky et al.	1953	The synthesis of esters of 2, 6-dimethyl-4-aminobenzoic acid
US2821540A (en)	1958-01-28	Preparation of hindered 4-acylamido-benzoates
EP0051247B1 (fr)	1985-01-09	Dérivés 4-thia- et 4-sulfinyl-PGI1, leur procédé de préparation et leurs compositions pharmaceutiques