DD299430A5 - Neue 1-oxa-2-oxo-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung - Google Patents

Neue 1-oxa-2-oxo-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung Download PDF

Info

Publication number: DD299430A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; oxo; oxa; methylene; spiro
Prior art date: 1989-08-10

Application number

DD90343362A

Other languages

German (de)

English (en)

Inventor

Edit Toth

Jozsef Toerley

Bela Hegedues

Laszlo Szporny

Bela Kiss

Eva Palosi

Dora Groo

Istvan Laszlovszky

Erzsebet Lapis

Ferenc Auth

Laszlo Gaal

Original Assignee

��@��@��@��@��Kk��

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.)

1989-08-10

Filing date

1990-08-09

Publication date

1992-04-16

1990-08-09 Application filed by ��@��@��@��@��Kk�� filed Critical ��@��@��@��@��Kk��

1992-04-16 Publication of DD299430A5 publication Critical patent/DD299430A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 34
SEUNTAIZLCAWDW-UHFFFAOYSA-N 1-oxa-8-azaspiro[4.5]decan-2-one Chemical class O1C(=O)CCC11CCNCC1 SEUNTAIZLCAWDW-UHFFFAOYSA-N 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 110
150000003839 salts Chemical group 0.000 claims abstract description 27
239000002253 acid Substances 0.000 claims abstract description 25
238000002360 preparation method Methods 0.000 claims abstract description 22
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 8
125000001424 substituent group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 7
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims abstract description 3
125000004953 trihalomethyl group Chemical group 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 52
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
239000011541 reaction mixture Substances 0.000 claims description 48
-1 [(4-methylpiperazin-1-yl) carbonyl] - Chemical class 0.000 claims description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
239000002585 base Substances 0.000 claims description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
239000012948 isocyanate Substances 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
150000002513 isocyanates Chemical class 0.000 claims description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
CYCSGNGCLXFNFZ-UHFFFAOYSA-N (4-ethynylpiperidin-4-yl) carbamate Chemical class NC(=O)OC1(C#C)CCNCC1 CYCSGNGCLXFNFZ-UHFFFAOYSA-N 0.000 claims description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
DTNXRKYDRUCILN-UHFFFAOYSA-N (4-acetylpiperidin-4-yl) carbamate Chemical class NC(=O)OC1(C(=O)C)CCNCC1 DTNXRKYDRUCILN-UHFFFAOYSA-N 0.000 claims description 8
229960000583 acetic acid Drugs 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
238000007363 ring formation reaction Methods 0.000 claims description 8
GVZFMFFUAZKMOB-UHFFFAOYSA-N 4-ethynylpiperidin-4-ol Chemical class C#CC1(O)CCNCC1 GVZFMFFUAZKMOB-UHFFFAOYSA-N 0.000 claims description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
229910000039 hydrogen halide Inorganic materials 0.000 claims description 6
239000012433 hydrogen halide Substances 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
VWADBHVASFOEHX-UHFFFAOYSA-N 1-(4-hydroxypiperidin-4-yl)ethanone Chemical class CC(=O)C1(O)CCNCC1 VWADBHVASFOEHX-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
230000003266 anti-allergic effect Effects 0.000 claims description 3
230000002082 anti-convulsion Effects 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
NDLFHDGJNUXKRA-UHFFFAOYSA-N 3-methyl-4-methylidene-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(C)C(=O)OC11CCNCC1 NDLFHDGJNUXKRA-UHFFFAOYSA-N 0.000 claims description 2
JIQHHWDRYBKJQM-UHFFFAOYSA-N 8-benzyl-4-methylidene-1,3-dioxa-8-azaspiro[4.5]decan-2-one Chemical compound C=C1OC(=O)OC11CCN(CC=2C=CC=CC=2)CC1 JIQHHWDRYBKJQM-UHFFFAOYSA-N 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000012362 glacial acetic acid Substances 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
210000000653 nervous system Anatomy 0.000 claims 2
UPXUBCQBJWDOCP-UHFFFAOYSA-N 3-decyl-4-hydroxy-4-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(CCCCCCCCCC)C(=O)OC11CCNCC1 UPXUBCQBJWDOCP-UHFFFAOYSA-N 0.000 claims 1
XKTKXGWJROBOEL-UHFFFAOYSA-N 3-heptyl-4-hydroxy-4-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(CCCCCCC)C(=O)OC11CCNCC1 XKTKXGWJROBOEL-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000000945 filler Substances 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
230000003204 osmotic effect Effects 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000003381 stabilizer Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 4
CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical class C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
238000002844 melting Methods 0.000 description 91
230000008018 melting Effects 0.000 description 91
239000000243 solution Substances 0.000 description 71
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 32
238000000921 elemental analysis Methods 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 27
230000002829 reductive effect Effects 0.000 description 26
239000002904 solvent Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
238000003756 stirring Methods 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000003054 catalyst Substances 0.000 description 15
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
239000007858 starting material Substances 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
230000007935 neutral effect Effects 0.000 description 12
239000008096 xylene Substances 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
239000012043 crude product Substances 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000012300 argon atmosphere Substances 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-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
210000000988 bone and bone Anatomy 0.000 description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000012071 phase Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000000725 suspension Substances 0.000 description 6
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
238000005352 clarification Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000002609 medium Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000008101 lactose Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000003921 oil Substances 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
239000012265 solid product Substances 0.000 description 4
239000000829 suppository Substances 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
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000008298 dragée Substances 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
150000003242 quaternary ammonium salts Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000005406 washing Methods 0.000 description 3
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230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
KRCMKUNIILUXPF-UHFFFAOYSA-N methyl 4-hydroxybenzoate;sodium Chemical compound [Na].COC(=O)C1=CC=C(O)C=C1 KRCMKUNIILUXPF-UHFFFAOYSA-N 0.000 description 1
JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
WRHKUEIRCPSNDZ-UHFFFAOYSA-N n-(2-chloropyridine-3-carbonyl)-3-cyclohexyl-4-methylidene-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC(=O)N1CCC2(C(N(C3CCCCC3)C(=O)O2)=C)CC1 WRHKUEIRCPSNDZ-UHFFFAOYSA-N 0.000 description 1
ZWJXOYAIZNZLKE-UHFFFAOYSA-N n-ethyl-4-methylidene-2-oxo-3-phenyl-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxamide Chemical compound C1CN(C(=O)NCC)CCC21C(=C)N(C=1C=CC=CC=1)C(=O)O2 ZWJXOYAIZNZLKE-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000008194 pharmaceutical composition Chemical group 0.000 description 1
WKMXSWXNYKBCFQ-UHFFFAOYSA-N phenyl 3-(4-chlorophenyl)-4-methylidene-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylate Chemical compound C1=CC(Cl)=CC=C1N1C(=C)C2(CCN(CC2)C(=O)OC=2C=CC=CC=2)OC1=O WKMXSWXNYKBCFQ-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000003825 pressing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

DD90343362A 1989-08-10 1990-08-09 Neue 1-oxa-2-oxo-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung DD299430A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU894092A HU204054B (en)	1989-08-10	1989-08-10	Process for producing new 1-oxa-2-oxo-8-azaspiro(4,5)decane derivatives and pharmaceutical compositions comprising same

Publications (1)

Publication Number	Publication Date
DD299430A5 true DD299430A5 (de)	1992-04-16

Family

ID=10966859

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343362A DD299430A5 (de)	1989-08-10	1990-08-09	Neue 1-oxa-2-oxo-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung

Country Status (22)

Country	Link
US (1)	US5157038A (fr)
EP (1)	EP0412820B1 (fr)
JP (1)	JPH0377886A (fr)
KR (1)	KR940002828B1 (fr)
CN (2)	CN1029403C (fr)
AT (1)	ATE102204T1 (fr)
AU (1)	AU621239B2 (fr)
DD (1)	DD299430A5 (fr)
DE (1)	DE69006973T2 (fr)
DK (1)	DK0412820T3 (fr)
ES (1)	ES2062386T3 (fr)
FI (1)	FI903973A7 (fr)
HU (1)	HU204054B (fr)
IE (1)	IE62297B1 (fr)
IL (1)	IL95322A (fr)
IS (1)	IS1578B (fr)
MY (1)	MY107125A (fr)
NO (1)	NO903510L (fr)
NZ (1)	NZ234844A (fr)
PL (2)	PL164653B1 (fr)
YU (1)	YU47749B (fr)
ZA (1)	ZA906298B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5756743A (en)	1996-04-10	1998-05-26	Hoechst Marion Roussel Inc.	Spiro cyclopent b!indole-piperidines!
RU2006132465A (ru) *	2004-02-10	2008-03-20	Ф.Хоффманн-Ля Рош Аг (Ch)	Модуляторы хемокинового рецептора ccr5
PE20081735A1 (es) *	2007-02-01	2009-01-18	Glaxo Group Ltd	Derivados de 1-oxa-3[4,5]decan-2-ona en el tratamiento de trastornos alimenticios
JP2010517966A (ja) *	2007-02-01	2010-05-27	グラクソグループリミテッド	摂食障害の処置のための１−オキサ−３−アザスピロ（４．５）デカン−２−オンおよび１−オキサ−３，８−ジアザスピロ（４．５）デカン−２−オン誘導体
JP6503008B2 (ja) *	2017-05-30	2019-04-17	高級アルコール工業株式会社	透明油性固形化粧料

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL127065C (fr) *	1964-04-22
US3594306A (en) *	1967-04-03	1971-07-20	Great Canadian Oil Sands	Separation cell and scavenger cell froths treatment
FR96352E (fr) *	1967-12-29	1972-06-16	Science Union & Cie	Nouveaux dérives du spiro (4,5) decane et leur procédé de préparation.
FR2036557A5 (fr) *	1969-03-25	1970-12-24	Logeais Laboratoires
GB1301254A (fr) *	1971-07-08	1972-12-29
US3856797A (en) *	1972-12-29	1974-12-24	Yoshitomi Pharmaceutical	8-aminoalkyl-3-oxo-1-thia-4,8-diazaspiro(4.5)decanes and analogs thereof
US4244961A (en) *	1978-10-26	1981-01-13	Syntex (U.S.A.) Inc.	1-Oxa-3,8-diazaspiro[4.5]decan-2-ones antihypertensive agents
FR2615515B1 (fr) *	1987-05-22	1989-06-30	Adir	Nouveaux derives du spiro 4, 5 decane, leur procede de preparation et les compositions pharmaceutiques les renfermant
HU204529B (en) *	1989-08-10	1992-01-28	Richter Gedeon Vegyeszet	Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them

1989
- 1989-08-10 HU HU894092A patent/HU204054B/hu not_active IP Right Cessation
1990
- 1990-08-08 KR KR1019900012167A patent/KR940002828B1/ko not_active Expired - Fee Related
- 1990-08-09 JP JP2209360A patent/JPH0377886A/ja active Pending
- 1990-08-09 MY MYPI90001339A patent/MY107125A/en unknown
- 1990-08-09 DK DK90308778.1T patent/DK0412820T3/da active
- 1990-08-09 DD DD90343362A patent/DD299430A5/de not_active IP Right Cessation
- 1990-08-09 IL IL9532290A patent/IL95322A/en not_active IP Right Cessation
- 1990-08-09 NO NO90903510A patent/NO903510L/no unknown
- 1990-08-09 EP EP90308778A patent/EP0412820B1/fr not_active Expired - Lifetime
- 1990-08-09 NZ NZ234844A patent/NZ234844A/en unknown
- 1990-08-09 ZA ZA906298A patent/ZA906298B/xx unknown
- 1990-08-09 ES ES90308778T patent/ES2062386T3/es not_active Expired - Lifetime
- 1990-08-09 IS IS3613A patent/IS1578B/is unknown
- 1990-08-09 DE DE69006973T patent/DE69006973T2/de not_active Expired - Fee Related
- 1990-08-09 YU YU153990A patent/YU47749B/sh unknown
- 1990-08-09 AU AU60805/90A patent/AU621239B2/en not_active Ceased
- 1990-08-09 IE IE288390A patent/IE62297B1/en not_active IP Right Cessation
- 1990-08-09 AT AT90308778T patent/ATE102204T1/de not_active IP Right Cessation
- 1990-08-10 CN CN90106982A patent/CN1029403C/zh not_active Expired - Fee Related
- 1990-08-10 PL PL90286441A patent/PL164653B1/pl unknown
- 1990-08-10 CN CN90106920A patent/CN1028531C/zh not_active Expired - Fee Related
- 1990-08-10 FI FI903973A patent/FI903973A7/fi not_active Application Discontinuation
- 1990-08-10 US US07/566,274 patent/US5157038A/en not_active Expired - Fee Related
- 1990-08-10 PL PL90300608A patent/PL164654B1/pl unknown

Also Published As

Publication number	Publication date
YU153990A (sh)	1992-12-21
PL164654B1 (pl)	1994-08-31
KR940002828B1 (ko)	1994-04-04
US5157038A (en)	1992-10-20
PL286441A1 (en)	1991-07-15
ATE102204T1 (de)	1994-03-15
IL95322A0 (en)	1991-06-30
IE62297B1 (en)	1995-01-25
IE902883A1 (en)	1991-02-27
IS3613A7 (is)	1991-02-11
CN1029403C (zh)	1995-08-02
ZA906298B (en)	1991-06-26
KR910004629A (ko)	1991-03-29
CN1049348A (zh)	1991-02-20
AU621239B2 (en)	1992-03-05
HUT55783A (en)	1991-06-28
CN1028531C (zh)	1995-05-24
AU6080590A (en)	1991-02-14
JPH0377886A (ja)	1991-04-03
DK0412820T3 (da)	1994-03-28
FI903973A7 (fi)	1991-02-11
NO903510D0 (no)	1990-08-09
DE69006973D1 (de)	1994-04-07
NO903510L (no)	1991-02-11
HU204054B (en)	1991-11-28
EP0412820B1 (fr)	1994-03-02
CN1049347A (zh)	1991-02-20
YU47749B (sh)	1996-01-08
EP0412820A3 (en)	1991-11-27
ES2062386T3 (es)	1994-12-16
PL164653B1 (en)	1994-08-31
IS1578B (is)	1995-06-08
NZ234844A (en)	1992-03-26
EP0412820A2 (fr)	1991-02-13
DE69006973T2 (de)	1994-06-16
IL95322A (en)	1994-01-25
FI903973A0 (fi)	1990-08-10
MY107125A (en)	1995-09-30

Legal Events

Date	Code	Title	Description
1998-08-27	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69929235T2 (de)	2006-08-24	Spiro-indole als y5-rezeptor antagonisten
DE69615214T2 (de)	2002-06-27	Substituierte heteroaromatische derivate
DE60302336T2 (de)	2006-08-03	Neue pyridin- und quinolin-derivate
US5032598A (en)	1991-07-16	Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents
EP0738722B1 (fr)	2003-06-25	Dérivés d'acides 5-amino-benzofuran-2-carboxyliques
EP0418716B1 (fr)	1994-04-06	Esters aminoalcohol d'acide thienylcarboxyliques leurs produits quaternaires, leur préparation et l'utilisation de ces composés
DE29724281U1 (de)	2000-08-10	4-Phenylpiperidin-Verbindungen
DE2658544A1 (de)	1978-04-13	Carbostyrilderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
GB1581500A (en)	1980-12-17	Pyridobenzodiazepines
DE69007905T2 (de)	1994-07-21	1-Oxa-2-oxo-8-azaspiro[4,5]decan-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen daraus.
EP1025100B1 (fr)	2002-01-23	Derives de tetrahydropyridopyrimidinone substitues en position 3, leur production et leur utilisation
DD149069A5 (de)	1981-06-24	Verfahren zur herstellung neuer piperidinopropylerivate
DD299430A5 (de)	1992-04-16	Neue 1-oxa-2-oxo-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung
DE2804519C2 (fr)	1990-06-13
DE3226921C2 (de)	1994-03-10	Neue 3,7-Diazabicyclo[3.3.1]nonan Verbindungen und Verfahren zu ihrer Herstellung
DD299425A5 (de)	1992-04-16	Neue 4,4-disubstituierte piperidin-derivate und verfahren zu ihrer herstellung
EP1194426B1 (fr)	2004-08-18	Derives de benzofuran
DD283141A5 (de)	1990-10-03	Verfahren zur herstellung kondensierter diazepinone
WO1990001025A1 (fr)	1990-02-08	Composes quaternaires d'enamine, procedes de fabrication et leur emploi comme decontracturants musculaires
DD213921A5 (de)	1984-09-26	Verfahren zur herstellung von substituierten nicotinamid 1-oxyd n- und seinen salzen
DD257430A5 (de)	1988-06-15	Verfahren zur herstellung von pyrrolo(1,2-a)(4,1)benzoxarepinen
EP2190831B1 (fr)	2015-02-25	Procédé de production de 1,3-dioxolane-2-ones et d'esters d'acide carboxylique par transacylation dans des conditions réactionnelles basiques
DE2520131C3 (de)	1981-07-30	1,1,-Disubstituierte Octahydro-indolo[2,3-a]chinolizine und verfahren zu deren Herstellung
DE69804853T2 (de)	2002-11-14	Verfahren zur herstellung von mequitazin und zwischenprodukt der synthese
CH654833A5 (de)	1986-03-14	4-aryl-2-methyl-1,2,3,4-tetrahydro-isochinolin-derivate.