NO790084L - Fremgangsmaate ved fremstilling av substituerte 1,5-cyclohexadien-carboxylsyrederivater - Google Patents
Fremgangsmaate ved fremstilling av substituerte 1,5-cyclohexadien-carboxylsyrederivaterInfo
- Publication number
- NO790084L NO790084L NO790084A NO790084A NO790084L NO 790084 L NO790084 L NO 790084L NO 790084 A NO790084 A NO 790084A NO 790084 A NO790084 A NO 790084A NO 790084 L NO790084 L NO 790084L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- chain
- straight
- carbon atoms
- hours
- Prior art date
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
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- 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
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- 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
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- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000013037 reversible inhibitor Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 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)
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 (sv) |
| JP (1) | JPS54100349A (sv) |
| AU (1) | AU4273078A (sv) |
| BE (1) | BE873412A (sv) |
| DE (1) | DE2855878A1 (sv) |
| DK (1) | DK12179A (sv) |
| ES (1) | ES476713A1 (sv) |
| FR (1) | FR2414494A1 (sv) |
| GB (1) | GB2012266B (sv) |
| IL (1) | IL56256A0 (sv) |
| IT (1) | IT1113738B (sv) |
| NL (1) | NL7900221A (sv) |
| NO (1) | NO790084L (sv) |
| NZ (1) | NZ189212A (sv) |
| PT (1) | PT69018A (sv) |
| SE (1) | SE7813351L (sv) |
| ZA (1) | ZA786945B (sv) |
Families Citing this family (4)
| 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 |
| US8964278B2 (en) | 2010-08-09 | 2015-02-24 | Gentex Corporation | Electro-optic system configured to reduce a perceived color change |
| US8228590B2 (en) | 2010-08-09 | 2012-07-24 | Gentex Corporation | Electro-optic system configured to reduce a perceived color change |
Family Cites Families (2)
| 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/sv 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 GB GB791000A patent/GB2012266B/en not_active Expired
- 1979-01-11 BE BE192840A patent/BE873412A/xx unknown
- 1979-01-11 FR FR7900647A patent/FR2414494A1/fr not_active Withdrawn
- 1979-01-11 NL NL7900221A patent/NL7900221A/xx not_active Application Discontinuation
- 1979-01-11 DK DK12179A patent/DK12179A/da not_active Application Discontinuation
- 1979-01-11 IT IT47594/79A patent/IT1113738B/it active
- 1979-01-11 NO NO790084A patent/NO790084L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7900221A (nl) | 1979-07-16 |
| BE873412A (fr) | 1979-05-02 |
| IT1113738B (it) | 1986-01-20 |
| GB2012266A (en) | 1979-07-25 |
| DK12179A (da) | 1979-07-13 |
| IT7947594A0 (it) | 1979-01-11 |
| FR2414494A1 (fr) | 1979-08-10 |
| SE7813351L (sv) | 1979-07-13 |
| NZ189212A (en) | 1980-11-14 |
| IL56256A0 (en) | 1979-03-12 |
| PT69018A (en) | 1979-02-01 |
| ES476713A1 (es) | 1980-01-01 |
| ZA786945B (en) | 1979-12-27 |
| JPS54100349A (en) | 1979-08-08 |
| DE2855878A1 (de) | 1979-07-19 |
| GB2012266B (en) | 1982-04-28 |
| AU4273078A (en) | 1979-07-19 |
| US4187316A (en) | 1980-02-05 |
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