NO841878L - Fremgangsmaate for fremstilling av terapeutisk aktive difenylazometinforbindelser - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive difenylazometinforbindelserInfo
- Publication number
- NO841878L NO841878L NO841878A NO841878A NO841878L NO 841878 L NO841878 L NO 841878L NO 841878 A NO841878 A NO 841878A NO 841878 A NO841878 A NO 841878A NO 841878 L NO841878 L NO 841878L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl radical
- radical
- alkoxy
- alkyl
- chain
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 13
- 230000001225 therapeutic effect Effects 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 13
- -1 alkali metal salt Chemical class 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012965 benzophenone Substances 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 15
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract description 5
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
- 239000002904 solvent Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- LNAURVNIKFHZNB-UHFFFAOYSA-N (5-chloro-2-hydroxy-3-methylphenyl)-(4-chlorophenyl)methanone Chemical compound CC1=CC(Cl)=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O LNAURVNIKFHZNB-UHFFFAOYSA-N 0.000 description 1
- CXUUBNDXKNQKJP-UHFFFAOYSA-N (5-chloro-2-hydroxy-3-propylphenyl)-(4-chlorophenyl)methanone Chemical compound CCCC1=CC(Cl)=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O CXUUBNDXKNQKJP-UHFFFAOYSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 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 description 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- 101100043441 Mus musculus Srsf12 gene Proteins 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000003374 anti-dyskinetic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- MAFQLJCYFMKEJJ-UHFFFAOYSA-N ethyl 4-aminobutanoate Chemical compound CCOC(=O)CCCN MAFQLJCYFMKEJJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012712 vegetable carbon Nutrition 0.000 description 1
- 239000004108 vegetable carbon Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8307863A FR2545822B1 (fr) | 1983-05-11 | 1983-05-11 | Diphenylazomethines portant une chaine esterifiee, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841878L true NO841878L (no) | 1984-11-12 |
Family
ID=9288787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841878A NO841878L (no) | 1983-05-11 | 1984-05-10 | Fremgangsmaate for fremstilling av terapeutisk aktive difenylazometinforbindelser |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0125975B1 (el) |
| JP (1) | JPS59212458A (el) |
| AT (1) | ATE18760T1 (el) |
| AU (1) | AU2788584A (el) |
| DE (1) | DE3460059D1 (el) |
| DK (1) | DK232084A (el) |
| ES (1) | ES8502678A1 (el) |
| FI (1) | FI841882A7 (el) |
| FR (1) | FR2545822B1 (el) |
| GR (1) | GR82093B (el) |
| HU (1) | HU191652B (el) |
| IL (1) | IL71796A0 (el) |
| NO (1) | NO841878L (el) |
| NZ (1) | NZ208118A (el) |
| PT (1) | PT78575A (el) |
| ZA (1) | ZA843545B (el) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8212083B2 (en) * | 2006-04-27 | 2012-07-03 | Intezyne Technologies, Inc. | Heterobifunctional poly(ethylene glycol) containing acid-labile amino protecting groups and uses thereof |
| CA3200428A1 (en) * | 2021-05-26 | 2022-12-01 | Sean N. Natoli | Pro-benefit agent compounds with carbon/nitrogen bonds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2319338A1 (fr) * | 1975-08-01 | 1977-02-25 | Synthelabo | Nouveaux derives de a- phenyl benzylideniques des acides amines, leur preparation et les medicaments qui en contiennent |
-
1983
- 1983-05-11 FR FR8307863A patent/FR2545822B1/fr not_active Expired
-
1984
- 1984-05-02 AT AT84400889T patent/ATE18760T1/de not_active IP Right Cessation
- 1984-05-02 DE DE8484400889T patent/DE3460059D1/de not_active Expired
- 1984-05-02 EP EP84400889A patent/EP0125975B1/fr not_active Expired
- 1984-05-10 ES ES532363A patent/ES8502678A1/es not_active Expired
- 1984-05-10 PT PT78575A patent/PT78575A/pt unknown
- 1984-05-10 FI FI841882A patent/FI841882A7/fi not_active Application Discontinuation
- 1984-05-10 GR GR74674A patent/GR82093B/el unknown
- 1984-05-10 DK DK232084A patent/DK232084A/da not_active Application Discontinuation
- 1984-05-10 ZA ZA843545A patent/ZA843545B/xx unknown
- 1984-05-10 JP JP59094420A patent/JPS59212458A/ja active Pending
- 1984-05-10 NZ NZ208118A patent/NZ208118A/en unknown
- 1984-05-10 IL IL71796A patent/IL71796A0/xx unknown
- 1984-05-10 HU HU841829A patent/HU191652B/hu unknown
- 1984-05-10 NO NO841878A patent/NO841878L/no unknown
- 1984-05-10 AU AU27885/84A patent/AU2788584A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DK232084D0 (da) | 1984-05-10 |
| IL71796A0 (en) | 1984-09-30 |
| DE3460059D1 (en) | 1986-04-30 |
| FI841882A0 (fi) | 1984-05-10 |
| AU2788584A (en) | 1984-11-15 |
| GR82093B (el) | 1984-12-13 |
| ATE18760T1 (de) | 1986-04-15 |
| PT78575A (fr) | 1984-06-01 |
| FR2545822B1 (fr) | 1985-07-05 |
| FR2545822A1 (fr) | 1984-11-16 |
| ZA843545B (en) | 1984-12-24 |
| ES532363A0 (es) | 1985-01-16 |
| DK232084A (da) | 1984-11-12 |
| FI841882A7 (fi) | 1984-11-12 |
| ES8502678A1 (es) | 1985-01-16 |
| EP0125975A1 (fr) | 1984-11-21 |
| HU191652B (en) | 1987-03-30 |
| HUT34436A (en) | 1985-03-28 |
| EP0125975B1 (fr) | 1986-03-26 |
| NZ208118A (en) | 1987-01-23 |
| JPS59212458A (ja) | 1984-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0084164B1 (de) | Neue Derivate bicyclischer Aminosäuren, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung sowie neue bicyclische Aminosäuren als Zwischenstufen und Verfahren zu deren Herstellung | |
| DE602004011767T2 (de) | Cyclohexylsulfone als gamma-sekretase-inhibitoren | |
| US6492522B1 (en) | Process and intermediates for production of donepezil and related compounds | |
| EP1383770B1 (de) | Verfahren zur herstellung von 4,6-diaminopyrimido 5,4-d]pyrimidinen | |
| DD283998A5 (de) | Verfahren zur herstellung von prolinderivaten und verwandten verbindungen | |
| US5300639A (en) | Thiazolo [5,4-b]azepine compounds | |
| ES2651245T3 (es) | Nuevo procedimiento para la preparación de 4,4'-(1-metil-1,2- etanodiilo)-bis-(2,6-piperazinadiona) | |
| EP0270982B1 (de) | Derivate bicyclischer Aminocarbonsäuren, Verfahren und Zwischenprodukte zu deren Herstellung sowie deren Verwendung | |
| DE19613549A1 (de) | Verfahren zur Herstellung von enantiomerenreinen Cycloalkano-indol- und azaindol-carbonsäuren und deren aktivierte Derivate | |
| NO841878L (no) | Fremgangsmaate for fremstilling av terapeutisk aktive difenylazometinforbindelser | |
| EP0252353B1 (de) | 4-Benzyloxy-3-pyrrolin-2-on-1-yl-acetamid, dessen Herstellung und Verwendung | |
| EP0496369B1 (de) | Verfahren zur Herstellung der racemischen und optisch aktiven 1,2,3,4-Tetrahydroisochinolin-3-carbonsäure sowie deren Vorprodukte | |
| US4709044A (en) | Biotin intermediates | |
| SU1618273A3 (ru) | Гербицидное средство | |
| WO1994026743A1 (de) | Verbessertes verfahren zur herstellung von xanthinderivaten, insbesondere von 1,3-dipropyl-8-(3-oxocyclopentyl)-xanthin | |
| EP0297620B1 (de) | Verfahren zur Herstellung bicyclischer Aminocarbonsäuren, Zwischenprodukte dieses Verfahrens und deren Verwendung | |
| US4782165A (en) | Process for biotin intermediates | |
| DE602005002738T2 (de) | Syntheseverfahren und benzoxathiepinzwischenprodukte | |
| EP0088252B1 (de) | Verfahren zur Herstellung von 1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolacetoxyessigsäure | |
| DE69301662T2 (de) | Optisch aktives hydrochinin (amino-3-phenyl)-1-ethansulfonat, deren herstellung und verwendung | |
| DE69333903T2 (de) | Optisch aktive 1-Phenylpyrrolidonderivate | |
| SU665803A3 (ru) | Способ получени имидов карбоновых кислот, их право-или левовращающих изомеров или их солей | |
| KR100523321B1 (ko) | 4-히드록시-2-피롤리디논의 제조방법 | |
| AT336602B (de) | Verfahren zur herstellung eines optisch aktiven thiolactons | |
| EP0154886A2 (de) | Carboxyalkyldipeptidderivate, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung |