IE55872B1 - Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives - Google Patents

Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives

Info

Publication number: IE55872B1
Authority: IE; Ireland
Prior art keywords: linear; branched; derivative; group; substituted
Prior art date: 1982-08-20

Application number

IE1933/83A

Other languages

English (en)

Other versions

IE831933L (en

Original Assignee

Continental Pharma

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.)

1982-08-20

Filing date

1983-08-18

Publication date

1991-02-14

1983-08-18 Application filed by Continental Pharma filed Critical Continental Pharma

1984-02-20 Publication of IE831933L publication Critical patent/IE831933L/xx

1991-02-14 Publication of IE55872B1 publication Critical patent/IE55872B1/en

Links

239000000203 mixture Substances 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
239000000460 chlorine Substances 0.000 claims abstract description 17
229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 15
125000004429 atom Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 12
125000003277 amino group Chemical group 0.000 claims abstract description 11
229910052794 bromium Inorganic materials 0.000 claims abstract description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
239000011737 fluorine Substances 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000000921 anthelmintic agent Substances 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 5
125000003545 alkoxy group Chemical group 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
-1 alkyl radical Chemical class 0.000 claims description 38
238000000034 method Methods 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 25
230000008569 process Effects 0.000 claims description 23
230000015572 biosynthetic process Effects 0.000 claims description 21
238000003786 synthesis reaction Methods 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
239000000243 solution Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
150000001408 amides Chemical class 0.000 claims description 14
230000009467 reduction Effects 0.000 claims description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000000376 reactant Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
230000009471 action Effects 0.000 claims description 7
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 7
239000000725 suspension Substances 0.000 claims description 7
238000005917 acylation reaction Methods 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 6
230000010933 acylation Effects 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
150000003951 lactams Chemical class 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 4
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
238000009472 formulation Methods 0.000 claims description 4
125000002560 nitrile group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
239000003826 tablet Substances 0.000 claims description 4
YZOPDRPLQHHSPV-UHFFFAOYSA-N N'-pentan-2-ylbutanehydrazide Chemical compound C(CCC)(=O)NNC(CCC)C YZOPDRPLQHHSPV-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
230000002526 effect on cardiovascular system Effects 0.000 claims description 3
239000000499 gel Substances 0.000 claims description 3
229920000159 gelatin Polymers 0.000 claims description 3
235000019322 gelatine Nutrition 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
150000002466 imines Chemical class 0.000 claims description 3
239000006187 pill Substances 0.000 claims description 3
230000003236 psychic effect Effects 0.000 claims description 3
239000006188 syrup Substances 0.000 claims description 3
235000020357 syrup Nutrition 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000000320 amidine group Chemical group 0.000 claims description 2
150000008064 anhydrides Chemical group 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical group Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000007937 lozenge Substances 0.000 claims description 2
230000000926 neurological effect Effects 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000008223 sterile water Substances 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims 6
238000006482 condensation reaction Methods 0.000 claims 2
ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
239000001828 Gelatine Substances 0.000 claims 1
YKHKOLKAMSBEFE-UHFFFAOYSA-N N'-pentylpentanehydrazide Chemical compound C(CCCC)(=O)NNCCCCC YKHKOLKAMSBEFE-UHFFFAOYSA-N 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
229940124326 anaesthetic agent Drugs 0.000 claims 1
230000003444 anaesthetic effect Effects 0.000 claims 1
229940124339 anthelmintic agent Drugs 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000002843 carboxylic acid group Chemical group 0.000 claims 1
230000007812 deficiency Effects 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000002552 dosage form Substances 0.000 claims 1
239000003193 general anesthetic agent Substances 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
239000012038 nucleophile Substances 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
229910021653 sulphate ion Inorganic materials 0.000 claims 1
208000012661 Dyskinesia Diseases 0.000 abstract description 3
206010020772 Hypertension Diseases 0.000 abstract description 3
208000001953 Hypotension Diseases 0.000 abstract description 3
208000018737 Parkinson disease Diseases 0.000 abstract description 3
239000000730 antalgic agent Substances 0.000 abstract description 3
230000000507 anthelmentic effect Effects 0.000 abstract description 3
206010015037 epilepsy Diseases 0.000 abstract description 3
230000036543 hypotension Effects 0.000 abstract description 3
208000005392 Spasm Diseases 0.000 abstract description 2
230000007547 defect Effects 0.000 abstract description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
239000000047 product Substances 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
230000000694 effects Effects 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
238000010992 reflux Methods 0.000 description 9
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000013256 coordination polymer Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 6
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 5
229960000583 acetic acid Drugs 0.000 description 5
AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 5
IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 5
150000007975 iminium salts Chemical class 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
206010010904 Convulsion Diseases 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
230000036461 convulsion Effects 0.000 description 4
238000010586 diagram Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000006870 function Effects 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
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
235000019759 Maize starch Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
238000012360 testing method Methods 0.000 description 3
230000009466 transformation Effects 0.000 description 3
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
CEMZQHFVTGKVFJ-UHFFFAOYSA-N 2-(pentylamino)butanamide Chemical compound CCCCCNC(CC)C(N)=O CEMZQHFVTGKVFJ-UHFFFAOYSA-N 0.000 description 2
JSAWFGSXRPCFSW-UHFFFAOYSA-N 5-chloropentanenitrile Chemical compound ClCCCCC#N JSAWFGSXRPCFSW-UHFFFAOYSA-N 0.000 description 2
VTBDHJGJHHHNTL-UHFFFAOYSA-N 6-(decylamino)hexanamide Chemical compound CCCCCCCCCCNCCCCCC(N)=O VTBDHJGJHHHNTL-UHFFFAOYSA-N 0.000 description 2
229910002012 Aerosil® Inorganic materials 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
229920000715 Mucilage Polymers 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
206010043994 Tonic convulsion Diseases 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000006399 behavior Effects 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000004820 halides Chemical group 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
NNFAFRAQHBRBCQ-UHFFFAOYSA-N 1-pentylpyrrolidin-2-one Chemical compound CCCCCN1CCCC1=O NNFAFRAQHBRBCQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
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 1
CKYHMCLCGUPTHW-UHFFFAOYSA-N 4-(hexylamino)butanamide Chemical compound CCCCCCNCCCC(N)=O CKYHMCLCGUPTHW-UHFFFAOYSA-N 0.000 description 1
QIUYKRAZSMRJDE-UHFFFAOYSA-N 4-(pentylamino)butanenitrile Chemical compound CCCCCNCCCC#N QIUYKRAZSMRJDE-UHFFFAOYSA-N 0.000 description 1
MVEPJLNIXKEKMI-UHFFFAOYSA-N 4-aminobutanamide;hydrochloride Chemical compound Cl.NCCCC(N)=O MVEPJLNIXKEKMI-UHFFFAOYSA-N 0.000 description 1
XYOXIERJKILWCG-UHFFFAOYSA-N 4-chlorobutanamide Chemical compound NC(=O)CCCCl XYOXIERJKILWCG-UHFFFAOYSA-N 0.000 description 1
ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 1
CDPKJZJVTHSESZ-UHFFFAOYSA-N 4-chlorophenylacetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1 CDPKJZJVTHSESZ-UHFFFAOYSA-N 0.000 description 1
WLPJSABQGGPQKK-UHFFFAOYSA-N 6-(pentylamino)hexanamide Chemical compound CCCCCNCCCCCC(N)=O WLPJSABQGGPQKK-UHFFFAOYSA-N 0.000 description 1
WEKYCORDQQDIEM-UHFFFAOYSA-N 6-aminohexanamide Chemical compound NCCCCCC(N)=O.NCCCCCC(N)=O WEKYCORDQQDIEM-UHFFFAOYSA-N 0.000 description 1
DHSSDEDRBUKTQY-UHFFFAOYSA-N 6-prop-2-enyl-4,5,7,8-tetrahydrothiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC=C)CCC2=C1N=C(N)S2 DHSSDEDRBUKTQY-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
206010000117 Abnormal behaviour Diseases 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101150047706 CASP6 gene Proteins 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
NKRISRRBUNTLRI-UHFFFAOYSA-N Cl.C(CCCCC)NCCCC(=O)N Chemical compound Cl.C(CCCCC)NCCCC(=O)N NKRISRRBUNTLRI-UHFFFAOYSA-N 0.000 description 1
JJELSSMQXNELQX-UHFFFAOYSA-N Cl.C(CCCCCCCCCCC)NCCCCC#N Chemical compound Cl.C(CCCCCCCCCCC)NCCCCC#N JJELSSMQXNELQX-UHFFFAOYSA-N 0.000 description 1
241001440269 Cutina Species 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 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
206010061217 Infestation Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000006679 Mentha X verticillata Nutrition 0.000 description 1
235000002899 Mentha suaveolens Nutrition 0.000 description 1
235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
ORDBIAQJBSMRBL-UHFFFAOYSA-N N'-decan-5-ylhexanehydrazide Chemical compound C(CCCCC)(=O)NNC(CCCCC)CCCC ORDBIAQJBSMRBL-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
241001126259 Nippostrongylus brasiliensis Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000091 aluminium hydride Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
DNKYMRIVXIQCFO-UHFFFAOYSA-N benzene pentane Chemical compound CCCCC.CCCCC.C1=CC=CC=C1 DNKYMRIVXIQCFO-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
238000010876 biochemical test Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
229960001631 carbomer Drugs 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000001638 cerebellum Anatomy 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
229960002200 flunitrazepam Drugs 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
QLBLDBLRERSWBA-UHFFFAOYSA-N hexanamide Chemical compound [CH2]CCCCC(N)=O QLBLDBLRERSWBA-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
244000045947 parasite Species 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 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
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000004321 preservation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229940041666 rectal gel Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
238000010099 solid forming Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IE1933/83A 1982-08-20 1983-08-18 Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives IE55872B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU84343		1982-08-20

Publications (2)

Publication Number	Publication Date
IE831933L IE831933L (en)	1984-02-20
IE55872B1 true IE55872B1 (en)	1991-02-14

Family

ID=19729937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1933/83A IE55872B1 (en)	1982-08-20	1983-08-18	Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives

Country Status (24)

Country	Link
JP (1)	JPS5962555A (el)
KR (1)	KR870000980B1 (el)
AU (2)	AU1814083A (el)
BE (1)	BE897566A (el)
CA (1)	CA1256899A (el)
CH (1)	CH659466A5 (el)
DE (2)	DE3329628A1 (el)
DK (1)	DK373383A (el)
ES (2)	ES8602608A1 (el)
FI (1)	FI832935A (el)
FR (1)	FR2531950B1 (el)
GB (1)	GB2126224B (el)
GR (1)	GR77444B (el)
IE (1)	IE55872B1 (el)
IL (1)	IL69543A (el)
IT (1)	IT1169767B (el)
MA (1)	MA19882A1 (el)
MX (1)	MX156348A (el)
NL (1)	NL8302916A (el)
NO (1)	NO163770C (el)
OA (1)	OA07525A (el)
PT (1)	PT77226B (el)
SE (1)	SE8304513L (el)
ZA (1)	ZA836130B (el)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE133795T1 (de) *	1983-08-01	1985-09-12	The Mclean Hospital Corp., Belmont, Mass.	Gaba-ester und gaba-analoge ester.
DE3445816C1 (de)	1984-12-15	1986-06-12	Behringwerke Ag, 3550 Marburg	Flaechenfoermiges diagnostisches Mittel
GB8813185D0 (en) *	1988-06-03	1988-07-06	Wyeth John & Brother Ltd	New method & amines used therein
CA2028782C (en) *	1989-11-07	2003-10-14	Christian T. Goralski	Process for the production of vinyl-gaba
US5585358A (en) *	1993-07-06	1996-12-17	Yissum Research Development Corporation Of The Hebrew University Of Jerusalem	Derivatives of valproic acid amides and 2-valproenoic acid amides, method of making and use thereof as anticonvulsant agents
KR100491282B1 (ko)	1996-07-24	2005-05-24	워너-램버트 캄파니 엘엘씨	통증 치료용 이소부틸가바 및 그의 유도체
FR2753967B1 (fr) *	1996-09-27	1998-11-27	Sod Conseils Rech Applic	Nouveaux derives de la phenoxyethylamine, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
UA59384C2 (uk)	1996-12-20	2003-09-15	Пфайзер, Інк.	Похідні сульфонамідів та амідів як агоністи простагландину, фармацевтична композиція та способи лікування на їх основі
UA67754C2 (uk)	1997-10-10	2004-07-15	Пфайзер, Інк.	Агоністи простагландину, фармацевтична композиція на їх основі (варіанти), спосіб нарощення та збереження кісткової маси у хребетних та спосіб лікування (варіанти)
HUP0600526A2 (en)	2000-07-21	2006-11-28	Teva Pharma	Use of derivatives of valproic acid and 2-valproenic acid amides for the treatment of mania in bipolar disorder
ATE397584T1 (de) *	2000-11-21	2008-06-15	Ucb Pharma Sa	N-alkylierte gaba verbindungen, verfahren zu deren herstellung und deren verwendung als arzneimittel
EP1675822A2 (en) *	2003-10-16	2006-07-05	Cara Therapeutics, Inc.	Amide or thioamide derivatives and their use in the treatment of pain
FR3018076B1 (fr) *	2014-03-03	2016-02-19	Arkema France	Procede de preparation de derives de l'acide 11-aminoundecanoique et de l'acide 12-aminododecanoique
WO2020031201A1 (en) *	2018-08-04	2020-02-13	Msn Laboratories Private Limited, R&D Center	Improved process for the preparation of 6-aminohexanoic acid
CN109593044B (zh) *	2018-12-06	2021-05-14	盐城工学院	一种烷基脂肪酸胺及其制备方法
CN115636761B (zh) *	2021-07-20	2024-07-05	中国石油天然气股份有限公司	一种油溶性表面活性剂、驱油剂及其应用

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE636245A (el) *
GB586645A (en) *	1944-07-19	1947-03-26	Burroughs Wellcome Co	Improvements relating to the synthesis of amino acid derivatives and salts thereof
GB775364A (en) *	1954-05-05	1957-05-22	Unilever Ltd	Improvements in soap compositions
US2851345A (en) *	1955-02-02	1958-09-09	Armour & Co	Fuel oil compositions
DE1189556B (de) *	1962-05-29	1965-03-25	Sandoz Ag	Verfahren zur Herstellung von 3-Diaethylaminobuttersaeure-N-methylanilid
BE647556A (el) *	1964-05-06	1964-08-31
IE33790B1 (en) *	1968-06-04	1974-10-30	Beecham Group Ltd	Derivatives of n-acylaminoacid amides
US3954778A (en) *	1970-03-03	1976-05-04	Zambon S.P.A.	Aminoacetyl derivatives of 2,3-diphenyl cyclopropyl amine
GB1369250A (en) *	1970-08-07	1974-10-02	Pfizer	Amines the preparation thereof and their use in pharmacejtical compositions
DE2234399A1 (de) *	1972-07-17	1974-01-31	Thomae Gmbh Dr K	Hautschutzmittel
US3947579A (en) *	1974-06-03	1976-03-30	Nelson Research & Development Company	Method and composition for potentiating neuroleptic drugs
GB1538207A (en) *	1975-12-09	1979-01-10	Mitsubishi Chem Ind	N2-arylsulphonyl-l-argininamides and the pharmaceutically acceptable salts thereof
LU78804A1 (de) *	1977-12-30	1979-07-20	Byk Gulden Lomberg Chem Fab	N-substituierte w-aminoalkanoyl-w-aminoalkansaeuren,ihre verwendung und verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
LU78805A1 (de) *	1977-12-30	1979-07-20	Byk Gulden Lomberg Chem Fab	Acylhydrocarbylaminoalkansaeuren,ihre herstellung und verwendung sowie sie enthaltende arzneimittel
DE3010599A1 (de) *	1979-03-22	1980-10-09	Continental Pharma	Derivate von glycinamid, deren herstellung und verwendung

1983
- 1983-08-16 DK DK373383A patent/DK373383A/da not_active Application Discontinuation
- 1983-08-16 FI FI832935A patent/FI832935A/fi not_active Application Discontinuation
- 1983-08-17 DE DE19833329628 patent/DE3329628A1/de active Granted
- 1983-08-17 DE DE3347867A patent/DE3347867C2/de not_active Expired
- 1983-08-17 CA CA000434769A patent/CA1256899A/en not_active Expired
- 1983-08-18 NO NO832965A patent/NO163770C/no unknown
- 1983-08-18 IE IE1933/83A patent/IE55872B1/en unknown
- 1983-08-18 GB GB08322245A patent/GB2126224B/en not_active Expired
- 1983-08-18 GR GR72245A patent/GR77444B/el unknown
- 1983-08-19 NL NL8302916A patent/NL8302916A/nl not_active Application Discontinuation
- 1983-08-19 SE SE8304513A patent/SE8304513L/xx not_active Application Discontinuation
- 1983-08-19 AU AU18140/83A patent/AU1814083A/en not_active Abandoned
- 1983-08-19 BE BE0/211380A patent/BE897566A/fr not_active IP Right Cessation
- 1983-08-19 ES ES525031A patent/ES8602608A1/es not_active Expired
- 1983-08-19 MX MX198462A patent/MX156348A/es unknown
- 1983-08-19 PT PT77226A patent/PT77226B/pt not_active IP Right Cessation
- 1983-08-19 FR FR8313490A patent/FR2531950B1/fr not_active Expired
- 1983-08-19 OA OA58092A patent/OA07525A/xx unknown
- 1983-08-19 CH CH4544/83A patent/CH659466A5/fr not_active IP Right Cessation
- 1983-08-19 IT IT22591/83A patent/IT1169767B/it active
- 1983-08-19 ZA ZA836130A patent/ZA836130B/xx unknown
- 1983-08-20 MA MA20104A patent/MA19882A1/fr unknown
- 1983-08-20 KR KR1019830003898A patent/KR870000980B1/ko not_active IP Right Cessation
- 1983-08-20 JP JP58150964A patent/JPS5962555A/ja active Granted
- 1983-08-22 IL IL69543A patent/IL69543A/xx unknown
1985
- 1985-09-02 ES ES546625A patent/ES8800658A1/es not_active Expired
1988
- 1988-04-18 AU AU14727/88A patent/AU1472788A/en not_active Abandoned

Also Published As

Publication number	Publication date
NO163770C (no)	1990-07-18
IT8322591A1 (it)	1985-02-19
ES546625A0 (es)	1987-11-16
BE897566A (fr)	1983-12-16
FR2531950A1 (fr)	1984-02-24
SE8304513D0 (sv)	1983-08-19
FI832935A (fi)	1984-02-21
GR77444B (el)	1984-09-14
DE3347867C2 (el)	1989-04-27
GB2126224A (en)	1984-03-21
IL69543A (en)	1987-01-30
SE8304513L (sv)	1984-02-21
ES525031A0 (es)	1985-12-16
MX156348A (es)	1988-08-09
GB2126224B (en)	1986-05-21
AU1814083A (en)	1984-02-23
DK373383A (da)	1984-02-21
IT1169767B (it)	1987-06-03
JPH0322869B2 (el)	1991-03-27
NL8302916A (nl)	1984-03-16
KR870000980B1 (ko)	1987-05-16
CA1256899A (en)	1989-07-04
CH659466A5 (fr)	1987-01-30
PT77226B (fr)	1986-02-04
NO163770B (no)	1990-04-09
DE3329628C2 (el)	1988-03-17
DK373383D0 (da)	1983-08-16
KR840006195A (ko)	1984-11-22
IT8322591A0 (it)	1983-08-19
GB8322245D0 (en)	1983-09-21
FI832935A0 (fi)	1983-08-16
ES8800658A1 (es)	1987-11-16
IE831933L (en)	1984-02-20
DE3347867A1 (el)	1985-04-18
NO832965L (no)	1984-02-21
DE3329628A1 (de)	1984-03-22
OA07525A (fr)	1985-03-31
JPS5962555A (ja)	1984-04-10
IL69543A0 (en)	1983-11-30
FR2531950B1 (fr)	1988-04-01
ZA836130B (en)	1984-04-25
PT77226A (fr)	1983-09-01
AU1472788A (en)	1988-10-27
ES8602608A1 (es)	1985-12-16
MA19882A1 (fr)	1984-04-01

Publication	Publication Date	Title
RU2544856C2 (ru)	2015-03-20	НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ
RU2102387C1 (ru)	1998-01-20	Производные n-ацил-2,3-бензодиазепина, или их стереоизомеры, или кислые соли присоединения, обладающие биологической активностью, связанной с воздействием на центральную нервную систему, и фармакологически активная композиция на их основе
KR890003424B1 (ko)	1989-09-20	비사이클릭 아미노산 유도체의 제조방법
IE55872B1 (en)	1991-02-14	Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
CA1237138A (en)	1988-05-24	(R)-.alpha.-ETHYL-2-OXO-L-PYRROLIDINEACETAMIDE
CS240954B2 (en)	1986-03-13	Preparation method of 1,2-dihydropyridines
GB2086393A (en)	1982-05-12	Bicyclic compounds
HU182801B (en)	1984-03-28	Process for preparing n-substituted aziridine-2-carboxylic acid derivatives
KR0169107B1 (ko)	1999-01-15	흥분성 아미노산 길항제
US5679677A (en)	1997-10-21	Heterocyclic carbamates, process for their preparation and medicaments
AU569537B2 (en)	1988-02-04	Novel 1-piperazinecarboxamide derivatives
GB2061274A (en)	1981-05-13	3-benzoyl-2-nitrophenylacetic acids metal salts amides and esters
JPH0610192B2 (ja)	1994-02-09	ビ―２ｈ―ピロール―ジオン化合物
DE2747369C2 (el)	1987-11-12
JPS59141559A (ja)	1984-08-14	ラクタムペプチド及びその製造方法並びに該ペプチドを含有する医薬
SU890976A3 (ru)	1981-12-15	Способ получени производных тетрагидро-1,3,5-триазин-2,6-дионов или их солей
FI66601C (fi)	1984-11-12	Foerfarande foer framstaellning av terapeutiskt aktiva 1,3-disubstituerade urinaemnen eller 2-tiourinaemnen
CA1338121C (en)	1996-03-05	Anticonvulsant and neuroprotective 2-aminoacetamide derivatives
EP0651743B1 (en)	1997-12-17	Indolinyl n-hydroxyurea and n-hydroxamic acid derivatives as lipoxygenase inhibitors
FR2470770A1 (fr)	1981-06-12	Nouveaux ethers de b-imidazolylethyle de quinoleine-2 ou 4-methanols, utiles notamment comme antimicrobiens, et leur procede de preparation
CH628885A5 (en)	1982-03-31	Piperidine derivative
US4612317A (en)	1986-09-16	Tetrahydro-β-carboline dithioic acid derivatives and treatment of liver diseases
GB2113682A (en)	1983-08-10	3,3 dialkyl or 3,3 alkene indolines
US5071849A (en)	1991-12-10	Dihydropyrimidothiazine derivatives