NO772267L - Fremgangsm}te til fremstilling av nye glycinamider - Google Patents

Fremgangsm}te til fremstilling av nye glycinamider

Info

Publication number: NO772267L
Authority: NO; Norway
Prior art keywords: stated; denotes; acetamide; dimethylhexyl; acid
Prior art date: 1976-06-28

Application number

NO772267A

Other languages

English (en)

Norwegian (no)

Inventor

Frederick Charles Copp

David Collard

Clive Vincent Denyer

Original Assignee

Wellcome Found

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.)

1976-06-28

Filing date

1977-06-27

Publication date

1977-12-29

1976-06-28 Priority claimed from GB26794/76A external-priority patent/GB1587065A/en

1977-06-27 Application filed by Wellcome Found filed Critical Wellcome Found

1977-12-29 Publication of NO772267L publication Critical patent/NO772267L/no

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
WEPNJTDVIIKRIK-UHFFFAOYSA-N 2-methylhept-2-ene Chemical compound CCCCC=C(C)C WEPNJTDVIIKRIK-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
239000011230 binding agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
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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239000000825 pharmaceutical preparation Substances 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
WUUVVCIJRXNQCJ-UHFFFAOYSA-N 1-cyclopentyl-2-methylpropan-2-ol Chemical compound CC(C)(O)CC1CCCC1 WUUVVCIJRXNQCJ-UHFFFAOYSA-N 0.000 description 2
ZUJAYOZGZBEPDY-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-heptan-2-ylacetamide Chemical compound C1=CC=C2C(=O)N(CC(=O)NC(C)CCCCC)C(=O)C2=C1 ZUJAYOZGZBEPDY-UHFFFAOYSA-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
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
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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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)

NO772267A 1976-06-28 1977-06-27 Fremgangsm}te til fremstilling av nye glycinamider NO772267L (no)

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 (pl)
JP (1)	JPS532418A (pl)
AR (1)	AR223133A1 (pl)
AU (1)	AU517624B2 (pl)
CA (1)	CA1081712A (pl)
CH (1)	CH636594A5 (pl)
DE (1)	DE2728872A1 (pl)
DK (1)	DK285377A (pl)
ES (1)	ES460118A1 (pl)
FI (1)	FI771987A7 (pl)
FR (1)	FR2356629A1 (pl)
GR (1)	GR64492B (pl)
HU (1)	HU181026B (pl)
IE (1)	IE45735B1 (pl)
IL (1)	IL52392A (pl)
IT (1)	IT1079720B (pl)
LU (1)	LU77632A1 (pl)
MC (1)	MC1145A1 (pl)
NL (1)	NL7707094A (pl)
NO (1)	NO772267L (pl)
NZ (1)	NZ184490A (pl)
PH (1)	PH14368A (pl)
PL (1)	PL199191A1 (pl)
PT (1)	PT66727B (pl)
SE (1)	SE7707367L (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (pl)	1969-08-14	1971-02-25

1977
- 1977-06-27 NO NO772267A patent/NO772267L/no unknown
- 1977-06-27 GR GR53815A patent/GR64492B/el unknown
- 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 JP JP7562877A patent/JPS532418A/ja active Pending
- 1977-06-27 CA CA281,478A patent/CA1081712A/en not_active Expired
- 1977-06-27 FR FR7719638A patent/FR2356629A1/fr not_active Withdrawn
- 1977-06-27 NL NL7707094A patent/NL7707094A/xx not_active Application Discontinuation
- 1977-06-27 AU AU26507/77A patent/AU517624B2/en not_active Expired
- 1977-06-27 IL IL52392A patent/IL52392A/xx unknown
- 1977-06-27 LU LU77632A patent/LU77632A1/xx unknown
- 1977-06-27 DK DK285377A patent/DK285377A/da unknown
- 1977-06-27 PT PT66727A patent/PT66727B/pt unknown
- 1977-06-27 FI FI771987A patent/FI771987A7/fi not_active Application Discontinuation
- 1977-06-27 MC MC771248A patent/MC1145A1/fr unknown
- 1977-06-27 ES ES460118A patent/ES460118A1/es not_active Expired
- 1977-06-27 NZ NZ184490A patent/NZ184490A/xx unknown
- 1977-06-27 HU HU77WE562A patent/HU181026B/hu unknown
- 1977-06-27 PL PL19919177A patent/PL199191A1/pl not_active IP Right Cessation
- 1977-06-27 PH PH19922A patent/PH14368A/en unknown
- 1977-06-27 IT IT49994/77A patent/IT1079720B/it active
- 1977-06-27 CH CH787177A patent/CH636594A5/de not_active IP Right Cessation
- 1977-06-27 AR AR268197A patent/AR223133A1/es active
- 1977-06-27 DE DE19772728872 patent/DE2728872A1/de not_active Withdrawn
1979
- 1979-07-23 US US06/059,955 patent/US4277498A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS532418A (en)	1978-01-11
AR223133A1 (es)	1981-07-31
DE2728872A1 (de)	1978-01-05
FI771987A7 (pl)	1977-12-29
IL52392A0 (en)	1977-08-31
NL7707094A (nl)	1977-12-30
PH14368A (en)	1981-06-17
IE45735L (en)	1977-12-28
PT66727B (en)	1979-05-14
AU2650777A (en)	1979-01-04
CH636594A5 (de)	1983-06-15
PT66727A (en)	1977-07-01
LU77632A1 (pl)	1978-02-02
HU181026B (en)	1983-05-30
PL199191A1 (pl)	1978-02-13
GR64492B (en)	1980-03-31
NZ184490A (en)	1980-10-08
ES460118A1 (es)	1978-05-01
CA1081712A (en)	1980-07-15
DK285377A (da)	1977-12-29
AU517624B2 (en)	1981-08-13
FR2356629A1 (fr)	1978-01-27
IE45735B1 (en)	1982-11-17
IL52392A (en)	1981-10-30
US4277498A (en)	1981-07-07
SE7707367L (sv)	1977-12-29
MC1145A1 (fr)	1978-01-30
IT1079720B (it)	1985-05-13

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US20120015943A1 (en)	2012-01-19	Substituted hydroxamic acids and uses thereof
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ITMI990866A1 (it)	2000-10-23	Nuovo composto
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US7560473B2 (en)	2009-07-14	Amine derivative with potassium channel regulatory function, its preparation and use
US7468365B2 (en)	2008-12-23	Lactam compound
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JPH0443917B2 (pl)	1992-07-20
DK169538B1 (da)	1994-11-28	Aminoalkoholer og syreadditionssalte deraf, fremgangsmåde til deres fremstilling og lægemidler med indhold af sådanne
JPH09506885A (ja)	1997-07-08	５ｈｔ▲下１ｄ▼（抗うつ作用）活性を有するインドール、インドリンおよびキノリン誘導体
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SK115197A3 (en)	1998-02-04	4-aminotetrahydrobenzisoxazole or -isothiazole compounds, pharmaceutical composition containing the same and their use
JPWO2014034626A1 (ja)	2016-08-08	Ｎ−［２−（｛２−［（２Ｓ）−２−シアノピロリジン−１−イル］−２−オキソエチル｝アミノ）−２−メチルプロピル］−２−メチルピラゾロ［１，５−ａ］ピリミジン−６−カルボキサミドの結晶
EP0092328B1 (en)	1987-05-20	Imidazoline derivatives
EP0402232A1 (fr)	1990-12-12	Dérivés de pyridobenzoindole, leur préparation et les compositions qui les contiennent
JP4773335B2 (ja)	2011-09-14	オキシトシンアンタゴニストとしてのピロリジン誘導体
KR880001863B1 (ko)	1988-09-23	사이클로헵텐 유도체의 제조방법
US4277498A (en)	1981-07-07	Amides
SK311392A3 (en)	1995-10-11	Use of substituted pyrolidines as medicines, effective matters and method of their preparation
NO145074B (no)	1981-09-28	Analogifremgangsmaate for fremstilling av terapeutisk aktive dibenzazepinderivater
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