NO772267L - Fremgangsm}te til fremstilling av nye glycinamider - Google Patents
Fremgangsm}te til fremstilling av nye glycinamiderInfo
- Publication number
- NO772267L NO772267L NO772267A NO772267A NO772267L NO 772267 L NO772267 L NO 772267L NO 772267 A NO772267 A NO 772267A NO 772267 A NO772267 A NO 772267A NO 772267 L NO772267 L NO 772267L
- Authority
- NO
- Norway
- Prior art keywords
- stated
- denotes
- acetamide
- dimethylhexyl
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 carbonium ion Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 239000002798 polar solvent Substances 0.000 claims description 12
- ACBMYYVZWKYLIP-UHFFFAOYSA-N 2-methylheptan-2-ol Chemical compound CCCCCC(C)(C)O ACBMYYVZWKYLIP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- XWAROIJJLKQMGK-UHFFFAOYSA-N 2-(benzylamino)-n-(2-methylheptan-2-yl)acetamide Chemical compound CCCCCC(C)(C)NC(=O)CNCC1=CC=CC=C1 XWAROIJJLKQMGK-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000005588 protonation Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- YRLUDSXDJLUNSX-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(2-methylheptan-2-ylamino)-2-oxoethyl]acetamide Chemical compound CCCCCC(C)(C)NC(=O)CNC(=O)C(F)(F)F YRLUDSXDJLUNSX-UHFFFAOYSA-N 0.000 claims description 3
- WQEZHGZZKGDGLP-UHFFFAOYSA-N 2-azido-n-(2-methylheptan-2-yl)acetamide Chemical compound CCCCCC(C)(C)NC(=O)CN=[N+]=[N-] WQEZHGZZKGDGLP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- HLKDXAJJHKXAIY-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-(2-methylheptan-2-yl)acetamide Chemical compound C1=CC=C2C(=O)N(CC(=O)NC(C)(C)CCCCC)C(=O)C2=C1 HLKDXAJJHKXAIY-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 3
- 238000011065 in-situ storage Methods 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000008361 aminoacetonitriles Chemical class 0.000 claims 1
- 125000005239 aroylamino group Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
- 239000000243 solution Substances 0.000 description 62
- 239000000203 mixture Substances 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- XSXYHGVTOLLCAU-UHFFFAOYSA-N 2-amino-n-(2-methylheptan-2-yl)acetamide Chemical compound CCCCCC(C)(C)NC(=O)CN XSXYHGVTOLLCAU-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000012230 colorless oil Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 11
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 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 9
- KJTIDLYAIIARFO-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetonitrile Chemical compound C1=CC=C2C(=O)N(CC#N)C(=O)C2=C1 KJTIDLYAIIARFO-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VDCJKMQSIDZPMC-UHFFFAOYSA-N 2-chloro-n-(2-methylheptan-2-yl)acetamide Chemical compound CCCCCC(C)(C)NC(=O)CCl VDCJKMQSIDZPMC-UHFFFAOYSA-N 0.000 description 7
- 208000020401 Depressive disease Diseases 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000001384 succinic acid Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000001589 carboacyl group Chemical group 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- YMWSLKSZSJOWOK-UHFFFAOYSA-N 2-amino-n-(2-methylheptan-2-yl)acetamide;butanedioic acid Chemical compound OC(=O)CCC(O)=O.CCCCCC(C)(C)NC(=O)CN YMWSLKSZSJOWOK-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XZRPLKUIHFAAFJ-UHFFFAOYSA-N 2-amino-n-heptan-2-ylacetamide Chemical compound CCCCCC(C)NC(=O)CN XZRPLKUIHFAAFJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- GTGIXCPOLMWQTC-UHFFFAOYSA-N cyanomethylazanium;hydrogen sulfate Chemical compound NCC#N.OS(O)(=O)=O GTGIXCPOLMWQTC-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000004615 ingredient 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
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 4
- XHEMBTKBRBWDAJ-WLHGVMLRSA-N 2-amino-n-(2-methylheptan-2-yl)acetamide;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.CCCCCC(C)(C)NC(=O)CN XHEMBTKBRBWDAJ-WLHGVMLRSA-N 0.000 description 3
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 3
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- 125000001118 alkylidene group Chemical group 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 208000024714 major depressive disease Diseases 0.000 description 3
- HHENWUYAOCBSAE-UHFFFAOYSA-N n-(cyanomethyl)formamide Chemical compound O=CNCC#N HHENWUYAOCBSAE-UHFFFAOYSA-N 0.000 description 3
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
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- PGOGSWXAPKFSRF-UHFFFAOYSA-N 2-amino-n-(2-methyloctan-2-yl)acetamide Chemical compound CCCCCCC(C)(C)NC(=O)CN PGOGSWXAPKFSRF-UHFFFAOYSA-N 0.000 description 2
- XGDOCEUIQYYJDC-UHFFFAOYSA-N 2-methylheptan-2-amine Chemical compound CCCCCC(C)(C)N XGDOCEUIQYYJDC-UHFFFAOYSA-N 0.000 description 2
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- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26794/76A GB1587065A (en) | 1976-06-28 | 1976-06-28 | Amides |
| GB2220477 | 1977-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO772267L true NO772267L (no) | 1977-12-29 |
Family
ID=26255791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO772267A NO772267L (no) | 1976-06-28 | 1977-06-27 | Fremgangsm}te til fremstilling av nye glycinamider |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4277498A (de) |
| JP (1) | JPS532418A (de) |
| AR (1) | AR223133A1 (de) |
| AU (1) | AU517624B2 (de) |
| CA (1) | CA1081712A (de) |
| CH (1) | CH636594A5 (de) |
| DE (1) | DE2728872A1 (de) |
| DK (1) | DK285377A (de) |
| ES (1) | ES460118A1 (de) |
| FI (1) | FI771987A (de) |
| FR (1) | FR2356629A1 (de) |
| GR (1) | GR64492B (de) |
| HU (1) | HU181026B (de) |
| IE (1) | IE45735B1 (de) |
| IL (1) | IL52392A (de) |
| IT (1) | IT1079720B (de) |
| LU (1) | LU77632A1 (de) |
| MC (1) | MC1145A1 (de) |
| NL (1) | NL7707094A (de) |
| NO (1) | NO772267L (de) |
| NZ (1) | NZ184490A (de) |
| PH (1) | PH14368A (de) |
| PL (1) | PL199191A1 (de) |
| PT (1) | PT66727B (de) |
| SE (1) | SE7707367L (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8517854D0 (en) * | 1985-07-15 | 1985-08-21 | Roussell Lab Ltd | Chemical compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1129950B (de) * | 1960-06-11 | 1962-05-24 | Knoll Ag | Verfahren zur Herstellung von antimikrobiell wirksamen Derivaten des Glycinamids |
| DE2034625A1 (de) | 1969-08-14 | 1971-02-25 |
-
1977
- 1977-06-27 NL NL7707094A patent/NL7707094A/xx not_active Application Discontinuation
- 1977-06-27 DK DK285377A patent/DK285377A/da unknown
- 1977-06-27 FI FI771987A patent/FI771987A/fi not_active Application Discontinuation
- 1977-06-27 CA CA281,478A patent/CA1081712A/en not_active Expired
- 1977-06-27 LU LU77632A patent/LU77632A1/xx unknown
- 1977-06-27 MC MC771248A patent/MC1145A1/xx unknown
- 1977-06-27 NZ NZ184490A patent/NZ184490A/xx unknown
- 1977-06-27 PT PT66727A patent/PT66727B/pt unknown
- 1977-06-27 IL IL52392A patent/IL52392A/xx unknown
- 1977-06-27 ES ES460118A patent/ES460118A1/es not_active Expired
- 1977-06-27 NO NO772267A patent/NO772267L/no unknown
- 1977-06-27 JP JP7562877A patent/JPS532418A/ja active Pending
- 1977-06-27 AU AU26507/77A patent/AU517624B2/en not_active Expired
- 1977-06-27 PH PH19922A patent/PH14368A/en unknown
- 1977-06-27 AR AR268197A patent/AR223133A1/es active
- 1977-06-27 GR GR53815A patent/GR64492B/el unknown
- 1977-06-27 PL PL19919177A patent/PL199191A1/xx not_active IP Right Cessation
- 1977-06-27 DE DE19772728872 patent/DE2728872A1/de not_active Withdrawn
- 1977-06-27 IT IT49994/77A patent/IT1079720B/it active
- 1977-06-27 FR FR7719638A patent/FR2356629A1/fr not_active Withdrawn
- 1977-06-27 SE SE7707367A patent/SE7707367L/xx not_active Application Discontinuation
- 1977-06-27 IE IE1303/77A patent/IE45735B1/en unknown
- 1977-06-27 HU HU77WE562A patent/HU181026B/hu unknown
- 1977-06-27 CH CH787177A patent/CH636594A5/de not_active IP Right Cessation
-
1979
- 1979-07-23 US US06/059,955 patent/US4277498A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MC1145A1 (fr) | 1978-01-30 |
| LU77632A1 (de) | 1978-02-02 |
| AU517624B2 (en) | 1981-08-13 |
| ES460118A1 (es) | 1978-05-01 |
| IL52392A (en) | 1981-10-30 |
| FR2356629A1 (fr) | 1978-01-27 |
| FI771987A (de) | 1977-12-29 |
| IE45735B1 (en) | 1982-11-17 |
| NL7707094A (nl) | 1977-12-30 |
| SE7707367L (sv) | 1977-12-29 |
| IE45735L (en) | 1977-12-28 |
| CA1081712A (en) | 1980-07-15 |
| HU181026B (en) | 1983-05-30 |
| PH14368A (en) | 1981-06-17 |
| GR64492B (en) | 1980-03-31 |
| NZ184490A (en) | 1980-10-08 |
| DK285377A (da) | 1977-12-29 |
| IT1079720B (it) | 1985-05-13 |
| AU2650777A (en) | 1979-01-04 |
| PT66727B (en) | 1979-05-14 |
| CH636594A5 (de) | 1983-06-15 |
| DE2728872A1 (de) | 1978-01-05 |
| IL52392A0 (en) | 1977-08-31 |
| JPS532418A (en) | 1978-01-11 |
| US4277498A (en) | 1981-07-07 |
| PL199191A1 (pl) | 1978-02-13 |
| AR223133A1 (es) | 1981-07-31 |
| PT66727A (en) | 1977-07-01 |
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