NO790084L - Fremgangsmaate ved fremstilling av substituerte 1,5-cyclohexadien-carboxylsyrederivater - Google Patents

Fremgangsmaate ved fremstilling av substituerte 1,5-cyclohexadien-carboxylsyrederivater

Info

Publication number: NO790084L
Authority: NO; Norway
Prior art keywords: acid; chain; straight; carbon atoms; hours
Prior art date: 1978-01-12

Application number

NO790084A

Other languages

English (en)

Norwegian (no)

Inventor

Brian Walter Metcalf

Michel Jung

Original Assignee

Merrell Toraude & Co

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.)

1978-01-12

Filing date

1979-01-11

Publication date

1979-07-13

1979-01-11 Application filed by Merrell Toraude & Co filed Critical Merrell Toraude & Co

1979-07-13 Publication of NO790084L publication Critical patent/NO790084L/no

Links

238000000034 method Methods 0.000 title claims description 8
QXHJRNVPNQKMLR-UHFFFAOYSA-N cyclohexa-1,5-diene-1-carboxylic acid Chemical class OC(=O)C1=CCCC=C1 QXHJRNVPNQKMLR-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
-1 benzyloxy, p-methoxybenzyloxy, 2,4-dimethoxybenzyloxy, trimethylsilyloxy Chemical group 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 29
239000002585 base Substances 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 29
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
230000007062 hydrolysis Effects 0.000 claims description 11
238000006460 hydrolysis reaction Methods 0.000 claims description 11
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
150000008065 acid anhydrides Chemical class 0.000 claims description 7
238000003756 stirring Methods 0.000 claims description 7
DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
SITZRXZBFQSDJO-UHFFFAOYSA-N cyclohexa-2,5-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CCC=C1 SITZRXZBFQSDJO-UHFFFAOYSA-N 0.000 claims description 6
150000004820 halides Chemical class 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
HCECZXZHXZYFFI-UHFFFAOYSA-N 3-aminocyclohexa-1,5-diene-1-carboxylic acid Chemical group NC1CC=CC(C(O)=O)=C1 HCECZXZHXZYFFI-UHFFFAOYSA-N 0.000 claims description 5
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 5
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 claims description 4
QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 0.000 claims description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
AGCDYGDGMDHPRP-UHFFFAOYSA-N 3-amino-6-bromocyclohexa-1,5-diene-1-carboxylic acid Chemical group NC1CC=C(Br)C(C(O)=O)=C1 AGCDYGDGMDHPRP-UHFFFAOYSA-N 0.000 claims description 3
XZBGCXZFNJKQNT-UHFFFAOYSA-N 3-aminocyclohexa-1,5-diene-1-carboxylic acid;2,2,2-trifluoroacetic acid Chemical group OC(=O)C(F)(F)F.NC1CC=CC(C(O)=O)=C1 XZBGCXZFNJKQNT-UHFFFAOYSA-N 0.000 claims description 3
238000010306 acid treatment Methods 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
239000007789 gas Substances 0.000 claims description 3
239000003456 ion exchange resin Substances 0.000 claims description 3
229920003303 ion-exchange polymer Polymers 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
235000019445 benzyl alcohol Nutrition 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
229960003692 gamma aminobutyric acid Drugs 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
102000003929 Transaminases Human genes 0.000 description 12
108090000340 Transaminases Proteins 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 7
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
KFNRJXCQEJIBER-ZCFIWIBFSA-N (S)-gabaculine Chemical compound N[C@H]1CC(C(O)=O)=CC=C1 KFNRJXCQEJIBER-ZCFIWIBFSA-N 0.000 description 5
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
229910021538 borax Inorganic materials 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
239000012973 diazabicyclooctane Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
PXHNRTFHJIQSST-UHFFFAOYSA-N methyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexa-1,5-diene-1-carboxylate Chemical compound COC(=O)C1=CC(NC(=O)OC(C)(C)C)CC=C1 PXHNRTFHJIQSST-UHFFFAOYSA-N 0.000 description 5
235000010339 sodium tetraborate Nutrition 0.000 description 5
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 5
DSKRINFJNYJGQK-UHFFFAOYSA-N 3-acetamidocyclohexa-1,5-diene-1-carboxylic acid Chemical compound CC(=O)NC1CC=CC(C(O)=O)=C1 DSKRINFJNYJGQK-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
KFNRJXCQEJIBER-UHFFFAOYSA-N 5-aminocyclohexa-1,3-diene-1-carboxylic acid Chemical compound NC1CC(C(O)=O)=CC=C1 KFNRJXCQEJIBER-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
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206010015037 epilepsy Diseases 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
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 3
208000027089 Parkinsonian disease Diseases 0.000 description 3
206010034010 Parkinsonism Diseases 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
229920002472 Starch Polymers 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
239000007943 implant Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
230000002427 irreversible effect Effects 0.000 description 3
DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
KEWCNQBRHIZMSB-UHFFFAOYSA-N methyl 6-bromo-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexa-1,5-diene-1-carboxylate Chemical compound COC(=O)C1=CC(NC(=O)OC(C)(C)C)CC=C1Br KEWCNQBRHIZMSB-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
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230000002829 reductive effect Effects 0.000 description 3
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239000003826 tablet Substances 0.000 description 3
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FCVBDFPSAINHRK-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexa-1,5-diene-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1CC=CC(C(O)=O)=C1 FCVBDFPSAINHRK-UHFFFAOYSA-N 0.000 description 2
CAUGSIDBLRGQMI-IHEARLNSSA-N 3-[[(2s)-2-aminopropanoyl]amino]cyclohexa-1,5-diene-1-carboxylic acid;hydrochloride Chemical compound Cl.C[C@H](N)C(=O)NC1CC=CC(C(O)=O)=C1 CAUGSIDBLRGQMI-IHEARLNSSA-N 0.000 description 2
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MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/30—Dithiocarbamic acids; Derivatives thereof having sulfur atoms of dithiocarbamic groups bound to other sulfur atoms
- C07C333/32—Thiuramsulfides; Thiurampolysulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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)

NO790084A 1978-01-12 1979-01-11 Fremgangsmaate ved fremstilling av substituerte 1,5-cyclohexadien-carboxylsyrederivater NO790084L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/868,860 US4187316A (en)	1978-01-12	1978-01-12	Substituted 1,5-cyclohexadiene carboxylic acid derivatives

Publications (1)

Publication Number	Publication Date
NO790084L true NO790084L (no)	1979-07-13

Family

ID=25352458

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO790084A NO790084L (no)	1978-01-12	1979-01-11	Fremgangsmaate ved fremstilling av substituerte 1,5-cyclohexadien-carboxylsyrederivater

Country Status (17)

Country	Link
US (1)	US4187316A (fr)
JP (1)	JPS54100349A (fr)
AU (1)	AU4273078A (fr)
BE (1)	BE873412A (fr)
DE (1)	DE2855878A1 (fr)
DK (1)	DK12179A (fr)
ES (1)	ES476713A1 (fr)
FR (1)	FR2414494A1 (fr)
GB (1)	GB2012266B (fr)
IL (1)	IL56256A0 (fr)
IT (1)	IT1113738B (fr)
NL (1)	NL7900221A (fr)
NO (1)	NO790084L (fr)
NZ (1)	NZ189212A (fr)
PT (1)	PT69018A (fr)
SE (1)	SE7813351L (fr)
ZA (1)	ZA786945B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4407671A (en) *	1982-12-06	1983-10-04	Shell Oil Company	Use of 3-aminocyclohexadienecarboxylic acids for controlling the growth of unwanted plants
DE4430090A1 (de) *	1994-08-25	1996-02-29	Bayer Ag	Cyclohexadienderivate
US8228590B2 (en)	2010-08-09	2012-07-24	Gentex Corporation	Electro-optic system configured to reduce a perceived color change
US8964278B2 (en)	2010-08-09	2015-02-24	Gentex Corporation	Electro-optic system configured to reduce a perceived color change

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3960927A (en) *	1975-03-18	1976-06-01	Richardson-Merrell Inc.	Olefinic derivatives of amino acids
US3959356A (en) *	1975-03-18	1976-05-25	Richardson-Merrell Inc.	Acetylene derivatives of amino acids

1978
- 1978-01-12 US US05/868,860 patent/US4187316A/en not_active Expired - Lifetime
- 1978-12-12 ZA ZA00786945A patent/ZA786945B/xx unknown
- 1978-12-18 NZ NZ189212A patent/NZ189212A/xx unknown
- 1978-12-19 IL IL56256A patent/IL56256A0/xx unknown
- 1978-12-20 AU AU42730/78A patent/AU4273078A/en active Pending
- 1978-12-23 DE DE19782855878 patent/DE2855878A1/de not_active Withdrawn
- 1978-12-28 SE SE7813351A patent/SE7813351L/xx unknown
1979
- 1979-01-02 PT PT69018A patent/PT69018A/pt unknown
- 1979-01-08 JP JP34079A patent/JPS54100349A/ja active Pending
- 1979-01-10 ES ES476713A patent/ES476713A1/es not_active Expired
- 1979-01-11 IT IT47594/79A patent/IT1113738B/it active
- 1979-01-11 GB GB791000A patent/GB2012266B/en not_active Expired
- 1979-01-11 NL NL7900221A patent/NL7900221A/xx not_active Application Discontinuation
- 1979-01-11 NO NO790084A patent/NO790084L/no unknown
- 1979-01-11 BE BE192840A patent/BE873412A/fr unknown
- 1979-01-11 FR FR7900647A patent/FR2414494A1/fr not_active Withdrawn
- 1979-01-11 DK DK12179A patent/DK12179A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
IT1113738B (it)	1986-01-20
BE873412A (fr)	1979-05-02
AU4273078A (en)	1979-07-19
IT7947594A0 (it)	1979-01-11
SE7813351L (sv)	1979-07-13
GB2012266B (en)	1982-04-28
GB2012266A (en)	1979-07-25
PT69018A (en)	1979-02-01
NZ189212A (en)	1980-11-14
NL7900221A (nl)	1979-07-16
JPS54100349A (en)	1979-08-08
ES476713A1 (es)	1980-01-01
US4187316A (en)	1980-02-05
DK12179A (da)	1979-07-13
FR2414494A1 (fr)	1979-08-10
DE2855878A1 (de)	1979-07-19
ZA786945B (en)	1979-12-27
IL56256A0 (en)	1979-03-12

Publication	Publication Date	Title
SU1416057A3 (ru)	1988-08-07	Способ получени пиридиловых соединений или их кислотно-аддитивных солей,или сложных эфиров,или амидов
JP5819954B2 (ja)	2015-11-24	抗炎症剤、免疫調節剤及び抗増殖剤としての化合物の新規カルシウム塩
EP0110781B1 (fr)	1987-04-01	(Amino-2 éthyl)-6 benzoxazolinones substituées, leur préparation et une composition pharmaceutique les contenant
NZ212856A (en)	1988-05-30	Glutarimide derivatives and pharmaceutical compositions
EP0139464B1 (fr)	1988-10-19	Dérivés de benzothiophène comme agents bronchodilateurs
EP0136274B1 (fr)	1989-11-08	Dérivés de 1-pipérazinecarboxamide, procédé de leur préparation et leur utilisation dans des compositions pharmaceutiques
EP0024965B1 (fr)	1983-04-27	Dérivés fluorés de méthyl-bêta-alanine, leur préparation et compositions pharmaceutiques les contenant
WO1987002584A1 (fr)	1987-05-07	Anti-convulsifs a l'acetamide et a la benzamide de cis-n-(2-aminocycloaliphatique)benzene
US4634699A (en)	1987-01-06	Branched chain phenothiazine
US5792797A (en)	1998-08-11	Pharmaceutical compounds
US4187316A (en)	1980-02-05	Substituted 1,5-cyclohexadiene carboxylic acid derivatives
NO790083L (no)	1979-07-13	Fremgangsmaate ved fremstilling av substituerte 1,4-cyclohexadien-carboxylsyrederivater
KR100382998B1 (ko)	2003-08-27	6-메톡시-1h-벤조트리아졸-5-카르복사미드유도체,그제조방법및그것을함유하는의약조성물
KR910003711B1 (ko)	1991-06-08	2-(n-피롤리디노)-3-이소부톡시-n-치환된 페닐-n-벤질-프로필아민의 제조방법
CS209864B2 (en)	1981-12-31	Method of making the substituted amids of the cinnamic acid
JPS6112900B2 (fr)	1986-04-10
JPS648613B2 (fr)	1989-02-14
GB1565021A (en)	1980-04-16	Pharmaceutical compositions containing alkylamine deratives
FR2540493A1 (fr)	1984-08-10	Oxime ethers basiques et compositions pharmaceutiques les contenant
AU628689B2 (en)	1992-09-17	New substituted benzothiazolinones, process for preparing these and pharmaceutical compositions containing them
US3539575A (en)	1970-11-10	Novel benzocyclobutene derivatives
US3470300A (en)	1969-09-30	Compositions and methods for relaxing skeletal muscles with o-substituted benzocyclobutenyl ketone oximes
KR800000262B1 (ko)	1980-04-09	3-아미노-2-하이드록시프로판의 디치환 페놀 에텔 유도체의 제조방법
US3366660A (en)	1968-01-30	Dibenzo cycloheptene thioiminoesters
FR2581996A1 (fr)	1986-11-21	Nouveaux derives 6-substitues de 6h-dibenzo(b, d)thiopyranne utiles notamment immunomodulateurs et antiviraux et leur preparation